Imidazo[1,2-a]pyridine derivatives

Abstract

The present invention relates to a compound represented by formula (I) [Formula 1] TIFF2024539634000184.tif72156, wherein the substituents are as defined in claim 1. The present invention relates to compounds of formula (I), processes and methods for preparing compounds of formula (I), agrochemical compositions comprising compounds of formula (I) as defined in claim 1, the preparation of these compositions and the use of these compounds or compositions in agriculture or horticulture for combating, preventing or controlling infestation of plants, harvested food crops, seeds or non-living material by phytopathogenic microorganisms, in particular fungi.

Description

[Technical Field]

[0001] The present invention relates to microbicidal imidazo[1,2-a]pyridine derivatives, for example as active ingredients, that have microbicidal activity, particularly bactericidal and fungicidal activity, more particularly activity against oomycetes. The present invention also relates to the preparation of these imidazo[1,2-a]pyridine derivatives, intermediates useful for the preparation of these imidazo[1,2-a]pyridine derivatives, the preparation of these intermediates, pesticide compositions comprising at least one imidazo[1,2-a]pyridine derivative, the preparation of these compositions, and the use of the imidazo[1,2-a]pyridine derivatives or compositions in agriculture or horticulture to combat, control, or prevent infestation of plants, harvested food crops, seeds, or non-living materials by phytopathogenic microorganisms, particularly fungi, more particularly oomycetes. [Background technology]

[0002] It has now surprisingly been found that certain novel imidazo[1,2-a]pyridine derivatives have advantageous bactericidal and fungicidal properties, particularly against oomycetes. Summary of the Invention [Means for solving the problem]

[0003] Thus, in a first aspect, the present invention provides, in embodiment 1, a compound of formula (I) [ka] (In the formula, Z is O or S, preferably Z is O; R 1 is C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenyl, C 2-6 Alkynyl, C 1-6 Alkoxy, C 1-6Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl, DiC 1-6 Alkylaminocarbonyl-C 1-6 alkyl and CN; 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenyl, C 2-6 Alkynyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl and diC 1-6 Alkylaminocarbonyl-C 1-6 Each of the alkyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxy, and CN; R 2a , R 2b and R 2c is H, hydroxy, halogen, CN, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkylsulfanyl, C1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 independently selected from alkyl; J is for CR 4 or N; G is CR 5 or N; If J is N, then G is CR 5 and when G is N, J is CR 4 and; R 3 , R 4 and R 5 is H, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, halogen, CN, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 independently selected from alkylcarbonyl and hydroxy; 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkylsulfanyl, C1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen and CN; A is CH or N; and R 6 is C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, DiC 1-6 Alkylamino, C 1-6 Alkoxyamino and C 1-6 Alkyl C 1-6 alkoxyamino, each of said groups being optionally substituted with 1 to 3 substituents independently selected from halogen and CN. or a salt or N-oxide thereof.

[0004] In preferred embodiment 1, where Z is O, the present invention provides a compound of formula (I) [ka] (In the formula, R 1 is C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl, C 1-4 alkoxy and CN; 1-4 Alkyl, C 1-4 Alkoxy-C1-4 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl and C 1-4 Each of the alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogen and CN; R 2a , R 2b and R 2c H, halogen, CN, C 1-4 Alkyl and C 1-4 independently selected from alkoxy; J is for CR 4 or N; G is CR 5 or N; If J is N, then G is CR 5 and when G is N, J is CR 4 and; R 3 , R 4 and R 5 is H, C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 independently selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen; A is CH or N; and R 6 is C 1-4 Alkyl, C 1-4 Alkoxy, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 alkyl, each of said groups being optionally substituted with 1 to 3 substituents independently selected from halogen or a salt or N-oxide thereof.

[0005] In preferred embodiment 1, where Z is S, the present invention provides a compound of formula (I) [ka] (In the formula, R 1 is C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl, C 1-4 alkoxy and CN; 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl and C 1-4 Each of the alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogen and CN; R 2a , R 2b and R 2c H, halogen, CN, C 1-4 Alkyl and C 1-4independently selected from alkoxy; J is for CR 4 or N; G is CR 5 or N; If J is N, then G is CR 5 and when G is N, J is CR 4 and; R 3 , R 4 and R 5 is H, C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 independently selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen; A is CH or N; and R 6 is C 1-4 Alkyl, C 1-4 Alkoxy, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 alkyl, each of said groups being optionally substituted with 1 to 3 substituents independently selected from halogen or a salt or N-oxide thereof.

[0006] In a second aspect, the present invention provides an agricultural chemical composition comprising a compound of formula (I), more specifically, an agricultural chemical composition comprising a fungicidal effective amount of a compound of formula (I), which may further comprise at least one compound selected from additional active ingredients, suitable inactive ingredients, carriers, adjuvants, and any mixture thereof.

[0007] The compounds of formula (I) can be used to control plant pathogenic microorganisms. Thus, to control plant pathogens, the compounds of formula (I) according to the present invention or compositions containing the compounds of formula (I) can be applied directly to the plant pathogens or to the habitat of the plant pathogens (especially plants susceptible to damage by plant pathogens) or to plant propagation material.

[0008] Thus, in a third aspect, the present invention provides the use of a compound of formula (I) or a composition comprising a compound of formula (I) as described herein for combating, preventing or controlling plant pathogens.

[0009] In a fourth aspect, the present invention provides a method for combating, preventing or controlling a plant pathogen, the method comprising the step of applying a compound of formula (I) or a composition comprising a compound of formula (I) as described herein to said plant pathogen or the habitat of said plant pathogen (particularly to plants susceptible to damage by plant pathogens) or to plant propagation material.

[0010] The compounds of formula (I) are particularly effective in combating, preventing or controlling plant pathogenic fungi, in particular oomycetes. Thus, in a fifth aspect, the present invention provides the use of a compound of formula (I) or a composition comprising a compound of formula (I) as described herein for controlling plant pathogenic fungi, in particular oomycetes.

[0011] In a sixth aspect, the present invention provides a method for combating, preventing or controlling phytopathogenic fungi, the method comprising applying to said phytopathogenic fungi or the habitat of said phytopathogenic fungi (in particular plants susceptible to attack by phytopathogenic fungi, especially oomycetes) or plant propagation material a compound of formula (I) as described herein or a composition comprising a compound of formula (I).

[0012] In a seventh aspect, the present invention provides compounds of formula (XV), formula (XVI), formula (XXI), formula (XXII), formula (II) and formula (XVII), each as described herein.

[0013] Where a group is indicated as substituted (eg, alkyl), this includes those groups that are part of other groups (eg, alkyl in alkylthio). DETAILED DESCRIPTION OF THE INVENTION

[0014] Definition: - the term "halogen" refers to fluorine (fluoro or F), chlorine (chloro or Cl), bromine (bromo or Br) or iodine (iodo or I), preferably fluorine, chlorine or bromine.

[0015] - the term "alkyl" as used herein alone or as part of a chemical group denotes a straight or branched chain hydrocarbon, preferably having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylpropyl, 1,3-dimethylbutyl, 1,4-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl and 2-ethylbutyl. Alkyl groups having 1 to 4 carbon atoms are preferred, for example methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl or t-butyl.

[0016] - the term "alkenyl" alone or as part of a chemical group denotes a straight or branched hydrocarbon, preferably having 2 to 6 carbon atoms and at least one double bond, such as vinyl, 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl- 2-pentenyl, 4-methyl-2-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl It represents methyl-2-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, and 1-ethyl-2-methyl-2-propenyl. Alkenyl groups having 2 to 4 carbon atoms are preferred, such as 2-propenyl, 2-butenyl, or 1-methyl-2-propenyl.

[0017] - the term "alkynyl" alone or as part of a chemical group denotes a straight or branched hydrocarbon, preferably having 2 to 6 carbon atoms and at least one triple bond, such as 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl , 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, and 2,5-hexazinyl. Alkynyl having 2 to 4 carbon atoms is preferred, such as ethynyl, 2-propynyl, or 2-butynyl-2-propenyl.

[0018] The term "cycloalkyl" alone or as part of a chemical group denotes a saturated or partially unsaturated monocyclic, bicyclic or tricyclic hydrocarbon, preferably having 3 to 10 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl or adamantyl. Cycloalkyls having 3, 4, 5, 6 or 7 carbon atoms are preferred, such as cyclopropyl or cyclobutyl.

[0019] - Hydroxyl or hydroxy refers to the -OH group.

[0020] 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.

[0021] N-oxides are oxidized forms of tertiary amines or nitrogen-containing aromatic heterocyclic compounds, as described, for example, in the book "Heterocyclic N-oxides", A. Albini and S. Pietra, CRC Press, Boca Raton 1991.

[0022] As a second embodiment, A is N; and R 6 C 1-4 Alkyl and C 1-4 alkoxy, each of said groups optionally substituted with 1 to 3 substituents independently selected from halogen.

[0023] As a third embodiment, A is N; and R 6 Compounds according to embodiment 1 or 2 are provided, wherein is selected from methyl, ethyl, and methoxy.

[0024] As a fourth embodiment, A is N; and R 6 Compounds according to any one of embodiments 1-3 are provided, wherein is methoxy.

[0025] As a fifth embodiment, A is CH; and R 6 C 1-4 Alkyl and C 1-4 alkoxy, each of said groups optionally substituted with 1 to 3 substituents independently selected from halogen.

[0026] As a sixth embodiment, A is CH; and R 6 Compounds according to any one of embodiments 1 to 5 are provided, wherein is selected from methyl, ethyl, and methoxy.

[0027] As a seventh embodiment, A is CH; and R 6 Compounds according to any one of embodiments 1, 5 or 6 are provided, wherein is methoxy.

[0028] As an eighth embodiment, R 1 C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 Alkyl and C 2-4 alkynyl, each of said groups optionally substituted with 1 to 3 substituents independently selected from halogen and CN.

[0029] As a ninth embodiment, R 1 is selected from methyl, ethyl, propyl, —CH2CH2—O—CH3, cyclopropyl, —CH2-cyclopropyl, —CH2—CF3, —CH2—C≡CH, CH2CH2CN, and —CH2—CN.

[0030] As a tenth embodiment, J is CR 4 and G is CR 5 and R 3 , R 4 and R 5 H, C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 independently selected from alkyl and hydroxy;1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Compounds according to any one of embodiments 1-9 are provided, wherein each alkyl group is optionally substituted with 1 to 3 substituents independently selected from halogen.

[0031] As an eleventh embodiment, J is CR 4 and G is CR 5 and R 3 , R 4 and R 5 H, C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 independently selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkynyl C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Compounds according to any one of embodiments 1 to 10 are provided, wherein each alkyl group is optionally substituted with 1 to 3 substituents independently selected from halogen.

[0032] As a twelfth embodiment, J is CR 4 and G is CR 5 and; R 3 and R 5 is H; and R 4 C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Compounds according to any one of embodiments 1 to 10 are provided, wherein each alkyl group is optionally substituted with 1 to 3 substituents independently selected from halogen.

[0033] As a thirteenth embodiment, J is CR 4 and G is CR 5 and; R 3 and R 5 is H; and R 4 C 1-4 Alkyl, C 1-4 selected from alkoxy, halogen, CN and hydroxy; 1-4 Alkyl and C 1-4Compounds according to embodiment 12 are provided, wherein each alkoxy group is optionally substituted with 1 to 3 substituents independently selected from halogen.

[0034] As a fourteenth embodiment, J is CR 4 and G is CR 5 and; R 3 and R 5 is H; and R 4 Compounds according to embodiment 12 are provided wherein is selected from methyl, methoxy, chloro, fluoro, bromo, CN, and hydroxy.

[0035] As a fifteenth embodiment, J is CR 4 and G is CR 5 and; R 3 is H; and R 4 and R 5 C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 independently selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3Compounds according to any one of embodiments 1 to 10 are provided, wherein each alkyl group is optionally substituted with 1 to 3 substituents independently selected from halogen.

[0036] As a sixteenth embodiment, J is CR 4 and G is CR 5 and; R 3 is H; and R 4 and R 5 C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 independently selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Compounds according to embodiment 15 are provided, wherein each alkyl group is optionally substituted with 1 to 3 substituents independently selected from halogen.

[0037] As a seventeenth embodiment, J is CR 4 and G is CR 5 and; R 3 is H; R 4 C 1-4 Alkyl, C 1-4 selected from alkoxy, halogen, CN and hydroxy; 1-4Alkyl and C 1-4 each of the alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogen; and R 5 C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Compounds according to embodiment 15 are provided, wherein each alkyl group is optionally substituted with 1 to 3 substituents independently selected from halogen.

[0038] As an eighteenth embodiment, J is CR 4 and G is CR 5 and; R 3 is H; R 4 is selected from methyl, methoxy, chloro, fluoro, bromo, CN, and hydroxy; and R 5 is selected from methyl, —O—CH—CH—O—CH, —CH—CH—O—CH, —O—CH, —CH—CFH, fluoro, chloro, bromo, iodo, cyclopropyl, —C≡CH, CN, —CF, isopropyl, and —O—CFH.

[0039] As a nineteenth embodiment, J is CR 4 and G is CR 5 and; R 3 and R 4 is H; and R 5 C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Compounds according to any one of embodiments 1 to 10 are provided, wherein each alkyl group is optionally substituted with 1 to 3 substituents independently selected from halogen.

[0040] As embodiment 20, J is CR 4 and G is CR 5 and; R 3 and R 4 is H; and R 5 C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Compounds according to embodiment 19 are provided, wherein each alkyl group is optionally substituted with 1 to 3 substituents independently selected from halogen.

[0041] As embodiment 21, J is CR 4 and G is CR 5 and; R 3 and R 4 is H; and R 5 is selected from methyl, —O—CH—CH—O—CH, —CH—CH—O—CH, —O—CH, —CH—CF—H, fluoro, chloro, bromo, iodo, cyclopropyl, —C≡CH, CN, —CF, isopropyl, and —O—CF—H.

[0042] As embodiment 22, J is CR 4 and G is CR 5 and; R 4 C 1-4 Alkyl, C 1-4 selected from alkoxy, halogen, CN, and hydroxy, wherein the alkyl group is unsubstituted or optionally substituted with 1 to 3 substituents independently selected from halogen; and R 3 and R 5 C 1-4 Alkyl, C1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 independently selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Compounds according to any one of embodiments 1 to 10 are provided, wherein each alkyl group is optionally substituted with 1 to 3 substituents independently selected from halogen.

[0043] As embodiment 23, J is CR 4 and G is CR 5 and; R 4 is selected from methyl, methoxy, chloro, fluoro, bromo, CN, and hydroxy; and R 3 and R 5 is independently selected from methyl, —O—CH—CH—O—CH, —CH—CHO—CH, —O—CH, —CH—CFH, fluoro, chloro, bromo, iodo, cyclopropyl, —C≡CH, CN, —CF, isopropyl, and —O—CFH.

[0044] As a 24th embodiment, J is CR 4 and G is CR 5 and R 3 , R 4 and R 5A compound according to any one of embodiments 1 to 10, wherein is H.

[0045] As a 25th embodiment, J is CR 4 and G is CR 5 and; R 3 and R 5 is H; and R 4 Compounds according to any one of embodiments 1 to 10 are provided, wherein is chloro or fluoro.

[0046] As a 26th embodiment, J is CR 4 and G is CR 5 and; R 3 is H; R 4 is fluoro; and R 5 Compounds according to any one of embodiments 1 to 10 are provided, wherein is methyl.

[0047] As a 27th embodiment, J is CR 4 and G is CR 5 and; R 3 is H; R 4 is fluoro; and R 5 A compound according to any one of embodiments 1 to 10 is provided, wherein is —O—CH 2 —CH 2 —O—CH 3 .

[0048] As embodiment 28, J is CR 4 and G is CR 5 and; R 3 is H; R 4 is chloro, fluoro, bromo or iodo; and R 5A compound according to any one of embodiments 1 to 10 is provided, wherein is —O—CH 3 .

[0049] As embodiment 29, J is CR 4 and G is CR 5 and; R 3 is H; R 4 is H; and R 5 is —CH 2 —CF 2 H.

[0050] As embodiment 30, J is CR 4 and G is CR 5 and; R 3 is H; R 4 is H; and R 5 Compounds according to any one of embodiments 1 to 10 are provided, wherein is chloro, fluoro, bromo, or iodo.

[0051] As embodiment 31, J is CR 4 and G is N; and R 3 and R 4 H, C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 independently selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Compounds according to any one of embodiments 1-9 are provided, wherein each alkyl group is optionally substituted with 1 to 3 substituents independently selected from halogen.

[0052] As embodiment 32, J is CR 4 and G is N; R 3 is H; and R 4 C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Compounds according to embodiment 31 are provided, wherein each alkyl group is optionally substituted with 1 to 3 substituents independently selected from halogen.

[0053] As embodiment 33, J is CR 4 and G is N; and R 3 C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen; R 4 is H.

[0054] As embodiment 34, J is CR 4 and G is N; and R 3 and R 4 H, C 1-4 Alkyl, C 1-4 Alkoxy, halogen, CN and C 2-4 alkynyl, C 1-4 Alkyl, C 1-4 Alkoxy and C 2-4 Compounds according to embodiment 31 are provided, wherein each alkynyl group is optionally substituted with 1 to 3 substituents independently selected from halogen.

[0055] As embodiment 35, J is CR 4and G is N; and R 3 and R 4 35. Compounds according to embodiment 34 are provided, wherein is independently selected from H, methyl, —OCH 3 , —CF 3 , —OCF 2 H, halogen, —C≡CH, and CN.

[0056] As embodiment 36, J is CR 4 and G is N; and R 3 and R 4 Compounds according to embodiment 34, wherein is H, are provided.

[0057] As embodiment 37, J is N and G is CR 5 and R 3 and R 5 H, C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 independently selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Compounds according to any one of embodiments 1-9 are provided, wherein each alkyl group is optionally substituted with 1 to 3 substituents independently selected from halogen.

[0058] As embodiment 38, J is N and G is CR 5 and; R 3 is H; and R 5 C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 independently selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Compounds according to embodiment 37 are provided, wherein each alkyl group is optionally substituted with 1 to 3 substituents independently selected from halogen.

[0059] As embodiment 39, J is N and G is CR 5 and; R 3 C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen; and R 5 Compounds according to embodiment 37, wherein is H, are provided.

[0060] As embodiment 40, J is N and G is CR 5 and R 3 and R 5 H, C 1-4 Alkyl, C 1-4 Alkoxy, halogen, CN and C 2-4 alkynyl, C 1-4 Alkyl, C 1-4 Alkoxy and C 2-4 Compounds according to embodiment 37 are provided, wherein each alkynyl group is optionally substituted with 1 to 3 substituents independently selected from halogen.

[0061] As embodiment 41, J is N and G is CR 5 and R 3 and R 5 38. Compounds according to embodiment 37 are provided, wherein is independently selected from H, methyl, —OCH 3 , —CF 3 , —OCF 2 H, halogen, —C≡CH, and CN.

[0062] As embodiment 42, J is N and G is CR 5 and R3 and R 5 Compounds according to embodiment 37, wherein is H, are provided.

[0063] As a preferred embodiment 10, A is N; R 3 is H; J is CR 4 and G is CR 5 and; R 4 C 1-4 Alkyl, C 1-4 selected from alkoxy, halogen, CN and hydroxy; 1-4 Alkyl and C 1-4 Each alkoxy group may be optionally substituted with 1 to 3 substituents independently selected from halogen; R 5 H, C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen; R 6 C 1-4 Alkyl and C 1-4alkoxy, each of said groups optionally substituted with 1 to 3 substituents independently selected from halogen.

[0064] In a preferred embodiment 10, wherein Z is O, A is N; R 3 is H; J is CR 4 and G is CR 5 and; R 4 is halogen or CN; R 5 C 1-4 Alkoxy, C 1-4 each of the alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogen; and R 6 C 1-4 Alkyl and C 1-4 alkoxy, each of said groups optionally substituted with 1 to 3 substituents independently selected from halogen.

[0065] In a more preferred embodiment 10, where Z is S, A is N; R 3 and R 5 is H; J is CR 4 and G is CR 5 and; R 4 is halogen or CN; and R 6 C 1-4 Alkyl and C 1-4 alkoxy, each of said groups optionally substituted with 1 to 3 substituents independently selected from halogen.

[0066] In a preferred embodiment according to any one of embodiments 2 to 42, Z is O.

[0067] In embodiment 43, the compound is - 3-(4-acetamidophenyl)-N-(4-chlorophenyl)-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide, - methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - 3-(6-acetamido-3-pyridyl)-N-(4-chlorophenyl)-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide, - methyl N-[5-[6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[4-[6-[(4-hydroxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-cyanophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[[3-(difluoromethoxy)phenyl]-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(3-ethylphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[methyl-(2-methyl-4-pyridyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(3,4-dimethylphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-isopropylphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[5-[6-[(4-cyanophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[4-[6-[methyl(p-tolyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-chloro-3-fluoro-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-7-methyl-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-5-methyl-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[5-chloro-6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[8-chloro-6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[7-chloro-6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[methyl(4-pyridyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[5-[6-[(4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[4-[6-[(2-methoxy-4-pyridyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-chlorophenyl)-cyclopropyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-chlorophenyl)-(cyclopropylmethyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-chlorophenyl)-(2,2,2-trifluoroethyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-chlorophenyl)-propyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-chlorophenyl)-(cyanomethyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-chlorophenyl)-ethyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-chlorophenyl)-prop-2-ynyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[7-bromo-6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[8-bromo-6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-8-fluoro-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-8-methoxy-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-5-cyano-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-7-methoxy-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-8-cyano-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-7-cyano-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-7-fluoro-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, - methyl N-[5-[6-[(3-ethynylphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(3-cyanophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(4-chloro-3-methyl-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(3,5-dimethylphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(4-fluoro-3-methyl-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[methyl-[3-(trifluoromethyl)phenyl]carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(3,4-difluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(4-cyano-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(3-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(4-cyano-3-methyl-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[methyl(m-tolyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(5-methoxy-3-pyridyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[methyl-(5-methyl-3-pyridyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[[3-(difluoromethyl)phenyl]-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(3,5-dimethoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(3-methoxy-5-methyl-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(6-fluoro-3-pyridyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[methyl(phenyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(3-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[methyl(p-tolyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(3,4-dimethylphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[[4-(difluoromethoxy)phenyl]-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(6-methoxy-3-pyridyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(4-bromophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(3-bromophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(2-methoxy-4-pyridyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(2-fluoro-4-pyridyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(3-cyclopropylphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(3-iodophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[[3-(2,2-difluoroethyl)phenyl]-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(4-chloro-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[(4-fluorophenyl)-(2-methoxyethyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, - methyl N-[5-[6-[[4-fluoro-3-(2-methoxyethoxy)phenyl]-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, N-(4-fluoro-3-methyl-phenyl)-N-methyl-3-[6-(propanoylamino)-3-pyridyl]imidazo[1,2-a]pyridine-6-carboxamide, and - Methyl N-[5-[6-[(4-fluorophenyl)-methyl-carbamothioyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate A compound according to any one of embodiments 1 to 42 is provided, wherein the compound is selected from:

[0068] The compounds in the following Tables 1.1 to 1.36 are illustrative of compounds of the present invention.

[0069] Table 1.1 shows the formula (I) [ka] (In the formula, Z is O; R 2a is H and R 2b is H and R 2c is H and R 6 is methyl; and R 1 , R 3 , J, G and A are as defined in Table Z.1 below) The present invention provides a compound of the formula:

[0070] (Continued from Table 1.1) Tables 1.2 to 1.36 show the R 2a , R 2b , R 2c and R 6 discloses each compound of formula (I) specifically defined in Tables 1.2 to 1.36, for which R 1 , R 3 Reference is made to Table Z.1 where J, G and A are specifically defined.

[0071]

Table 1-1

Table 1-2

Table 1-3

Table 1-4

Table 1-5

Table 1-6

Table 1-7

Table 1-8

Table 1-9

Table 1-10

Table 1-11

Table 1-12

Table 1-13

Table 1-14

Table 1-15

Table 1-16

Table 1-17

[0072] Table 1.2: This table shows the R 2a is H and R 2b is H and R 2c is H and R 6 is methoxy and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0073] Table 1.3: This table shows the R 2a is methyl and R 2b is H and R 2c is H and R 6 is methyl and R1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0074] Table 1.4: This table shows the R 2a is methyl and R 2b is H and R 2c is H and R 6 is methoxy and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0075] Table 1.5: This table shows the R 2a is fluoro and R 2b is H and R 2c is H and R 6 is methyl and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0076] Table 1.6: This table shows the R 2a is fluoro and R 2b is H and R 2c is H and R 6 is methoxy and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0077] Table 1.7: This table shows the R 2a is chloro and R 2b is H and R 2c is H and R 6 is methyl and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0078] Table 1.8: This table shows the R 2a is chloro and R 2b is H and R2c is H and R 6 is methoxy and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0079] Table 1.9: This table shows the R 2a is bromo and R 2b is H and R 2c is H and R 6 is methyl and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0080] Table 1.10: This table shows the R 2a is bromo and R 2b is H and R 2c is H and R 6 is methoxy and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0081] Table 1.11: This table shows the R 2a is cyano and R 2b is H and R 2c is H and R 6 is methyl and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0082] Table 1.12: This table shows the R 2a is cyano and R 2b is H and R 2c is H and R 6 is methoxy and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0083] Table 1.13: This table shows the R 2a is methoxy and R 2b is H and R 2c is H and R 6 is methyl and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0084] Table 1.14: This table shows the R 2a is methoxy and R 2b is H and R 2c is H and R 6 is methoxy and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0085] Table 1.15: This table shows the R 2a is H and R 2b is methyl and R 2c is H and R 6 is methyl and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0086] Table 1.16: This table shows the R 2a is H and R 2b is methyl and R 2c is H and R 6 is methoxy and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0087] Table 1.17: This table shows the R 2a is H and R 2b is methoxy and R 2c is H and R 6 is methyl and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0088] Table 1.18: This table shows the R 2a is H and R 2b is methoxy and R 2c is H and R 6 is methoxy and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0089] Table 1.19: This table shows the R 2a is H and R 2b is fluoro and R 2c is H and R 6 is methyl and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0090] Table 1.20: This table shows the R 2a is H and R 2b is fluoro and R 2c is H and R 6 is methoxy and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0091] Table 1.21: This table shows the R 2a is H and R 2b is chloro and R 2c is H and R 6 is methyl and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0092] Table 1.22: This table shows the R 2a is H and R 2b is chloro and R 2c is H and R6 is methoxy and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0093] Table 1.23: This table shows the R 2a is H and R 2b is bromo and R 2c is H and R 6 is methyl and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0094] Table 1.24: This table shows the R 2a is H and R 2b is bromo and R 2c is H and R 6 is methoxy and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0095] Table 1.25: This table shows the R 2a is H and R 2b is cyano and R 2c is H and R 6 is methyl and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0096] Table 1.26: This table shows the R 2a is H and R 2b is cyano and R 2c is H and R 6 is methoxy and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0097] Table 1.27: This table shows the R 2ais H and R 2b is H and R 2c is methyl and R 6 is methyl and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0098] Table 1.28: This table shows the R 2a is H and R 2b is H and R 2c is methyl and R 6 is methoxy and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0099] Table 1.29: This table shows the R 2a is H and R 2b is H and R 2c is fluoro and R 6 is methyl and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0100] Table 1.30: This table shows the R 2a is H and R 2b is H and R 2c is fluoro and R 6 is methoxy and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0101] Table 1.31: This table shows the R 2a is H and R 2b is H and R 2c is chloro and R 6 is methyl and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0102] Table 1.32: This table shows the R 2a is H and R 2b is H and R 2c is chloro and R 6 is methoxy and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0103] Table 1.33: This table shows the R 2a is H and R 2b is H and R 2c is bromo and R 6 is methyl and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0104] Table 1.34: This table shows the R 2a is H and R 2b is H and R 2c is bromo and R 6 is methoxy and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0105] Table 1.35: This table shows the R 2a is H and R 2b is H and R 2c is cyano and R 6 is methyl and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0106] Table 1.36: This table shows the R 2a is H and R 2b is H and R 2c is cyano and R 6 is methoxy and R 1 , R 3

[0013] Disclosed are certain compounds of formula (I) wherein the values ​​of J, G, and A are as defined in Table Z.1.

[0107] The compounds of the present invention may have numerous benefits, including, inter alia, advantageous levels of biological activity for the protection of plants against diseases caused by fungi or excellent properties for use as agrochemical active ingredients (e.g., high biological activity, advantageous spectrum of activity, high safety profile, improved physicochemical properties, or high biodegradability). The compounds of the present invention have particularly advantageous levels of biological activity for the protection of plants against oomycetes such as Phytophthora, Plasmopara, and Pythium.

[0108] The compounds of the present invention can be prepared as shown in the following schemes, in which, unless otherwise specified, the definition of each variable is as defined above for the compounds of formula (I) defined in embodiment 1.

[0109] Compounds of formula (I) where Z is O can be prepared as shown in Schemes 1 to 14 below, in which, unless otherwise specified, the definitions of each variable are as defined herein.

[0110] Compounds of formula (I) can be prepared by reacting a compound of formula (II) wherein X is chloro (Cl), bromo (Br) or iodo (I) with R in the presence of a base such as CsCO, KCO or NaOtBu and in the presence of a suitable palladium catalyst such as tetrakistriphenylphosphine palladium, palladium chloride, [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II), palladium acetate or bis(diphenylphosphine)palladium(II) chloride in a suitable solvent such as dimethylformamide, dioxane, tetrahydrofuran, ethanol or water. 7 are each independently hydrogen, C1-C6 alkyl, or two R 7can be prepared by Suzuki cross-coupling with compounds of formula (III), which can be taken together to form a C3-C8 cycloalkyl. This transformation is shown in Scheme 1. [ka] Scheme 1

[0111] Compounds of formula (II) where X is Cl, Br, or I can be prepared by reacting compounds of formula (IV) where X is Cl, Br, or I with compounds of formula (V) and a coupling agent such as N,N'-dicyclohexylcarbodiimide, bis(2-oxo-3-oxazolidinyl)phosphinic chloride, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, propylphosphonic anhydride, or cyanuric chloride, and optionally a base such as triethylamine, ethyldiisopropylamine, or N-methylmorpholine, in a suitable solvent such as ethyl acetate, dimethylformamide, tetrahydrofuran, or dichloromethane. This transformation is shown in Scheme 2. [ka] Scheme 2

[0112] Compounds of formula (IV) where X is Cl, Br or I are commercially available or where X is Cl, Br or I and R 8 Compounds of formula (VI), where is C1-C6 alkyl, can be prepared by saponification using a base such as NaOH or LiOH in a suitable solvent such as methanol, ethanol or water at temperatures between RT and reflux. This transformation is shown in Scheme 3. [ka] Scheme 3

[0113] Alternatively, compounds of formula (II) where X is Cl, Br or I can be reacted with compounds of formula (II) where X is Cl, Br or I and R 8 The compound of formula (VI), in which R is C1-C6 alkyl, can be directly prepared by reacting the compound of formula (V). These transformations have been described in the literature (see, for example, Weinreb, S. et al. Tetrahedron Lett. 1977, 48, 4171; Woodward, S. et al. in Tetrahedron Letters 2006, 47, 5767; Woodward, S. et al. in Org. Process Res. Dev. 2015, 19, 831). This transformation is shown in Scheme 4. [ka] Scheme 4

[0114] X is Cl, Br or I, and R 8 Compounds of formula (VI) where R is C1-C6 alkyl are commercially available or can be prepared by dissolving R in a suitable solvent such as dichloromethane, chloroform, tetrahydrofuran or acetonitrile. 8 can be prepared by reacting a compound of formula (VII), where is C1-C6 alkyl, with a halogenating agent such as N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, or bromine. This transformation is shown in Scheme 5. [ka] Scheme 5

[0115] R 8 Compounds of formula (VII) where X is C1-C6 alkyl are commercially available or can be prepared by reacting compounds of formula (VIII) where X is Cl, Br or I with carbon monoxide and an alcohol R in the presence of a catalyst such as PdCl2dppf and optionally a base such as triethylamine. 8 OH(R8 can be prepared by reaction with a C1-C6 alkyl. This transformation is shown in Scheme 6. [ka] Scheme 6

[0116] Compounds of formula (VIII) are commercially available or can be prepared by reacting compounds of formula (IX) where X is Cl, Br or I with compounds of formula (X) where X is Cl, Br or I or compounds of formula (X) where X is Cl, Br or I and R 9 are independently C1-C6 alkyl, or two R 9 can be prepared by reacting R with its corresponding acetal of formula (XI), which can be taken together to form a C3-C8 cycloalkyl. Optionally, the results of the reaction can be improved by using a base such as sodium bicarbonate or potassium carbonate, or an acid such as p-toluenesulfonic acid or hydrogen bromide. Furthermore, this transformation can be carried out by reacting R 8 From the compound of formula (XII) where R is C1-C6 alkyl, 8 Compounds of formula (VII), where is C1-C6 alkyl, can be prepared and used to prepare compounds of formula (XIII) from compounds of formula (XIV). These transformations are shown in Scheme 7. [ka] Scheme 7

[0117] Compounds of formula (IX) where X is Cl, Br or I, R 8 The compounds of formula (XII) and (XIV) in which is C1-C6 alkyl can be prepared by known methods or are commercially available.

[0118] Alternatively, compounds of formula (I) can be prepared by reacting compounds of formula (XV) with compounds of formula (V) and a coupling agent such as N,N'-dicyclohexylcarbodiimide, bis(2-oxo-3-oxazolidinyl)phosphinic chloride, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, propylphosphonic anhydride, or cyanuric chloride, and optionally a base such as triethylamine, ethyldiisopropylamine, or N-methylmorpholine, in a suitable solvent such as ethyl acetate, dimethylformamide, tetrahydrofuran, or dichloromethane. This transformation is shown in Scheme 8. [ka] Scheme 8

[0119] The compound of formula (XV) is R 8 Compounds of formula (XVI), where is C1-C6 alkyl, can be prepared by saponification using a base such as NaOH or LiOH in a suitable solvent such as methanol, ethanol or water at temperatures between RT and reflux. This transformation is shown in Scheme 9. [ka] Scheme 9

[0120] R 8 Compounds of formula (XVI), wherein X is Cl, Br or I and R is C1-C6 alkyl can be prepared by reacting compounds of formula (XVI) wherein X is Cl, Br or I and R is C1-C6 alkyl in the presence of a base such as Cs2CO3, K2CO3 or NaOtBu and in the presence of a suitable palladium catalyst such as tetrakistriphenylphosphinepalladium, palladium chloride, [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II), palladium acetate or bis(diphenylphosphine)palladium(II) chloride in a suitable solvent such as dimethylformamide, dioxane, tetrahydrofuran, ethanol or water. 8 is a C1-C6 alkyl group; and 7are each independently hydrogen, C1-C6 alkyl, or two R 7 can be prepared by Suzuki cross-coupling of a compound of formula (III) with a compound of formula (III), which can combine to form a C3-C8 cycloalkyl. Furthermore, this transformation can be utilized to prepare a compound of formula (XV) from a compound of formula (IV). These transformations are shown in Scheme 10. [ka] Scheme 10

[0121] Alternatively, compounds of formula (II) where X is Cl, Br or I can be prepared by reacting compounds of formula (XVII) with a halogenating agent such as N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide or bromine in a suitable solvent such as dichloromethane, chloroform, tetrahydrofuran or acetonitrile. This transformation is shown in Scheme 11. [ka] Scheme 11

[0122] Compounds of formula (XVII) can be prepared by reacting compounds of formula (XIII) with compounds of formula (V) and a coupling agent such as N,N'-dicyclohexylcarbodiimide, bis(2-oxo-3-oxazolidinyl)phosphinic chloride, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, propylphosphonic anhydride or cyanuric chloride, and optionally a base such as triethylamine, ethyldiisopropylamine or N-methylmorpholine in a suitable solvent such as ethyl acetate, dimethylformamide, tetrahydrofuran or dichloromethane. This transformation is shown in Scheme 12. [ka] Scheme 12

[0123] Alternatively, compounds of formula (II) can be prepared by reacting compounds of formula (XVIII) with compounds of formula (XIX) (where Y is Cl, Br, I, OSOCF, OSOCHCH, or OSOCH) in the presence of a base such as CsCO, KCO, or NaOtBu. This transformation is shown in Scheme 13. [ka] Scheme 13

[0124] Compounds of formula (XVIII), where X is Cl, Br, or I, can be prepared by reacting compounds of formula (IV), where X is Cl, Br, or I, with compounds of formula (XX) and a coupling agent such as N,N'-dicyclohexylcarbodiimide, bis(2-oxo-3-oxazolidinyl)phosphinic chloride, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, propylphosphonic anhydride, or cyanuric chloride, and optionally a base such as triethylamine, ethyldiisopropylamine, or N-methylmorpholine, in a suitable solvent such as ethyl acetate, dimethylformamide, tetrahydrofuran, or dichloromethane. This transformation is shown in Scheme 14. [ka] Scheme 14

[0125] Alternatively, compounds of formula (I) can be prepared by reacting a compound of formula (XXI) with a compound of formula (XXII) (wherein Y is OH) and a coupling agent such as N,N'-dicyclohexylcarbodiimide, bis(2-oxo-3-oxazolidinyl)phosphinic chloride, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, propylphosphonic anhydride or cyanuric chloride and optionally a base such as triethylamine, ethyldiisopropylamine or N-methylmorpholine in a suitable solvent such as ethyl acetate, dimethylformamide, tetrahydrofuran or dichloromethane. This transformation can also be carried out by reacting a compound of formula (XXI) with a compound of formula (XXII) (wherein Y is Cl) and optionally a base such as triethylamine, ethyldiisopropylamine or pyridine in a suitable solvent such as ethyl acetate, pyridine or tetrahydrofuran. This transformation is shown in Scheme 15. [ka] Scheme 15

[0126] Compounds of formula (XXI) can be prepared by reacting a compound of formula (II) wherein X is Cl, Br or I with R 7 are each independently hydrogen, C1-C6 alkyl, or two R 7 can be prepared by Suzuki cross-coupling with compounds of formula (XXIII), which can be taken together to form a C3-C8 cycloalkyl. This transformation is shown in Scheme 16. [ka] Scheme 16

[0127] Compounds of formula (V) and compounds of formula (XX) can be prepared by known methods or are commercially available.

[0128] R 7 are each independently hydrogen, C1-C6 alkyl, or two R 7 Compounds of formula (III) in which may be taken together to form a C3-C8 cycloalkyl may be prepared by known methods or are commercially available.

[0129] It is understood that one skilled in the art will recognize that the above amide coupling reaction between an acid, an amine, and a coupling agent can also be carried out using the corresponding acid chloride and an amine. The conversion of an acid to its corresponding acid chloride is well known to those skilled in the art.

[0130] Compounds of formula (Ib) can be prepared by reacting compounds of formula (I) where Z is O with phosphorus pentasulfide or Lawesson's reagent (CAS: 19172-47-5) in a suitable solvent such as toluene, xylene or dichloromethane. This transformation is shown in Scheme 17. [ka] Scheme 17

[0131] Alternatively, compounds of formula (Ib) wherein Z is S can be prepared by reacting a compound of formula (XXIV) with a compound of formula (XXII) (wherein Y is OH) and a coupling agent such as N,N'-dicyclohexylcarbodiimide, bis(2-oxo-3-oxazolidinyl)phosphinic chloride, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, propylphosphonic anhydride or cyanuric chloride and optionally a base such as triethylamine, ethyldiisopropylamine or N-methylmorpholine in a suitable solvent such as ethyl acetate, dimethylformamide, tetrahydrofuran or dichloromethane. This transformation can also be carried out by reacting a compound of formula (XXI) with a compound of formula (XXII) (wherein Y is Cl) and optionally a base such as triethylamine, ethyldiisopropylamine or pyridine in a suitable solvent such as ethyl acetate, pyridine or tetrahydrofuran. This transformation is shown in Scheme 18. [ka] Scheme 18

[0132] Compounds of formula (XXIV) can be prepared by reacting compounds of formula (XXI) with phosphorus pentasulfide or Lawesson's reagent (CAS: 19172-47-5) in a suitable solvent such as toluene, xylene or dichloromethane. This transformation is shown in Scheme 19. [ka] Scheme 19

[0133] When the term "a compound according to the invention" is used, this refers to a compound according to any one of embodiments 1 to 43 as defined above.

[0134] Alternatively, compounds according to any one of embodiments 1 to 43 can be obtained by transformation using standard synthetic techniques known to those skilled in the art, including, but not limited to, oxidation reactions, reduction reactions, hydrolysis reactions, coupling reactions, aromatic nucleophilic or electrophilic substitution reactions, nucleophilic substitution reactions, nucleophilic addition reactions, olefination reactions, oxime formation reactions, alkylation reactions, and halogenation reactions.

[0135] A compound according to any one of the embodiments 1 to 43 can be converted into another compound according to any one of the embodiments 1 to 43 in a manner known per se by replacing one or more substituents of the starting compound according to any one of the embodiments 1 to 43 with (one or more) other substituents according to the invention in a conventional manner.

[0136] Depending on the reaction conditions and the choice of starting materials appropriate in each case, it is possible, for example, to replace only one substituent with another substituent according to the invention in one reaction step, or to replace several substituents with another substituent according to the invention in the same reaction step.

[0137] Salts of the compounds according to any one of embodiments 1 to 43 can be prepared in a manner known per se. Thus, for example, acid addition salts of the compounds according to any one of embodiments 1 to 43 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.

[0138] The salts of the compounds according to any one of embodiments 1 to 43 may be converted into the free compounds in a conventional manner, for example by treating the acid addition salts with a suitable basic compound or a suitable ion exchange reagent, and the salts with bases with a suitable acid or a suitable ion exchange reagent.

[0139] A salt of a compound according to any one of the embodiments 1 to 43 can be converted into another salt, that is an acid addition salt, of a compound according to any one of the embodiments 1 to 43, in a manner known per se, by treating the salt of an inorganic acid, e.g. the hydrochloride, with a suitable metal salt of the acid, e.g. silver acetate, such as the sodium, barium or silver salt of the acid, in a suitable solvent in which the inorganic salt formed, e.g. silver chloride, is insoluble and therefore precipitates from the reaction mixture.

[0140] Depending on the procedure or reaction conditions, compounds according to any one of embodiments 1 to 43 that have the property of forming salts can be obtained in free form or in salt form.

[0141] The compounds according to any one of embodiments 1 to 43, in each case in free or salt form, and, where appropriate, their tautomers, can exist in the form of one of the possible stereoisomers or as mixtures thereof, e.g., in the form of pure stereoisomers, such as enantiomers and / or diastereomers, or as stereoisomeric mixtures, e.g., racemates, diastereomeric mixtures or racemic mixtures, depending, for example, on the number, the absolute and relative configuration of asymmetric carbon atoms occurring in the molecule and / or on the configuration of non-aromatic double bonds occurring in the molecule. The invention relates not only to pure stereoisomers, but also to all possible stereoisomeric mixtures, and is to be understood in this sense in each case hereinbefore and hereinafter, even if stereochemical details are not specifically mentioned in each case.

[0142] Diastereomeric or racemic mixtures of compounds according to any one of embodiments 1 to 43, in free or salt form, which may be obtained depending on the starting materials and procedures selected, can be separated into the pure diastereomers or racemates by known methods on the basis of the physicochemical differences of the components, for example, by fractional crystallization, distillation, and / or chromatography.

[0143] Enantiomeric mixtures, such as racemates, obtainable in a similar manner can be resolved into their optical antipodes by known methods, for example recrystallization from optically active solvents, chromatography on chiral adsorbents, for example high-performance liquid chromatography (HPLC) on acetylcellulose, cleavage with specific immobilized enzymes using suitable microorganisms, formation of inclusion compounds, the use of chiral crown ethers, for example, which complex with only one enantiomer, or conversion into diastereomeric salts, for example by reacting the basic final product racemate with an optically active acid, for example a carboxylic acid such as camphor, tartaric acid or malic acid, or a sulfonic acid, for example camphorsulfonic acid, and separating the diastereomeric mixtures thus obtainable, for example, by fractional crystallization on account of their different solubilities, to give diastereomers from which the desired enantiomer can be liberated by the action of a suitable reagent, for example a basic reagent.

[0144] Pure diastereomers or enantiomers can be obtained according to the present invention not only by separating the appropriate stereoisomeric mixtures but also by generally known methods of diastereoselective or enantioselective synthesis, e.g. by carrying out the process according to the invention using starting materials of the appropriate stereochemistry.

[0145] The N-oxides can be prepared by reacting a compound according to any one of embodiments 1 to 5 with a suitable oxidizing agent, such as the HO / urea adduct, in the presence of an acid anhydride, such as trifluoroacetic anhydride. Such oxidations are known in the literature, for example from J. Med. Chem., 32(12), 2561-73, 1989 or WO 00 / 15615.

[0146] If the individual components have different biological activities, it is advantageous to isolate or synthesize in each case the more biologically effective stereoisomer, e.g. an enantiomer or diastereomer, or a stereoisomeric mixture, e.g. an enantiomeric or diastereomeric mixture.

[0147] The compounds according to any one of embodiments 1 to 5 and, where appropriate, their tautomers, in each case in free or salt form, can also, where appropriate, be obtained in the form of hydrates and / or contain other solvents, for example solvents that may have been used for the crystallization of the compounds present in solid form.

[0148] The following examples illustrate, but do not limit, the present invention.

[0149] The present invention also provides intermediates useful for preparing compounds according to any one of embodiments 1-43.

[0150] The following intermediates are novel and as such form additional aspects of the invention.

[0151] Formula (XV) [ka] (In the formula, A is CH or N; R 6 is C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, DiC 1-6 Alkylamino, C 1-6 Alkoxyamino and C 1-6 Alkyl C 1-6 alkoxyamino, each of said groups being optionally substituted with 1 to 3 substituents independently selected from halogen and CN, preferably R 6 is C 1-4 Alkyl, C 1-4 Alkoxy, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3alkyl, each of said groups being optionally substituted with 1 to 3 substituents independently selected from halogen; and R 2a , R 2b and R 2c is H, hydroxy, halogen, CN, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 alkyl, preferably R 2a , R 2b and R 2c H, halogen, CN, C 1-4 Alkyl and C 1-4 alkoxy) Compound.

[0152] A, R 2a , R 2b , R 2c and R 6 The preferences for are the same as the preferences given for the corresponding substituents of the compounds of formula (I).

[0153] Formula (XVI) [ka] (In the formula, A is CH or N; R 6 is C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6Alkylamino, DiC 1-6 Alkylamino, C 1-6 Alkoxyamino and C 1-6 Alkyl C 1-6 alkoxyamino, each of said groups being optionally substituted with 1 to 3 substituents independently selected from halogen and CN; preferably, R 6 is C 1-4 Alkyl, C 1-4 Alkoxy, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 alkyl, each of said groups being optionally substituted with 1 to 3 substituents independently selected from halogen; R 8 is C1-C6 alkyl, preferably R 8 is selected from methyl and ethyl; and R 2a , R 2b and R 2c is H, hydroxy, halogen, CN, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 alkyl, preferably R 2a , R 2b and R 2c H, halogen, CN, C 1-4 Alkyl and C 1-4 alkoxy) Compound.

[0154] A, R 2a , R 2b , R 2c and R 6The preferences for are the same as the preferences given for the corresponding substituents of the compounds of formula (I).

[0155] Formula (XXI) [ka] (In the formula, A is CH or N; and R 2a , R 2b and R 2c is H, hydroxy, halogen, CN, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 alkyl, preferably R 2a , R 2b and R 2c H, halogen, CN, C 1-4 Alkyl and C 1-4 alkoxy) Compound.

[0156] R 2a , R 2b and R 2c The preferences for are the same as the preferences given for the corresponding substituents of the compounds of formula (I).

[0157] Formula (XXII) [ka] (In the formula, A is CH or N; R 8 is C1-C6 alkyl, preferably R 8is selected from methyl and ethyl; and R 2a , R 2b and R 2c is H, hydroxy, halogen, CN, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 alkyl, preferably R 2a , R 2b and R 2c H, halogen, CN, C 1-4 Alkyl and C 1-4 alkoxy) Compound.

[0158] R 2a , R 2b and R 2c The preferences for are the same as the preferences given for the corresponding substituents of the compounds of formula (I).

[0159] Formula (II) [ka] (In the formula, R 1 is C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl, C 1-4 alkoxy and CN; 1-4 Alkyl, C 1-4 Alkoxy-C1-4 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl and C 1-4 Each of the alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogen and CN; R 2a , R 2b and R 2c is H, hydroxy, halogen, CN, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 alkyl, preferably R 2a , R 2b and R 2c H, halogen, CN, C 1-4 Alkyl and C 1-4 independently selected from alkoxy; J is for CR 4 or N; G is CR 5 or N; If J is N, then G is CR 5 and when G is N, J is CR 4 and; R 3 , R 4 and R 5 is H, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, halogen, CN, C 2-6 Alkenyl, C2-6 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 independently selected from alkylcarbonyl and hydroxy; 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen and CN, preferably R 3 , R 4 and R 5 is H, C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3independently selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen; and X is Cl, Br or I, more preferably X is Cl or I. Compound.

[0160] In certain embodiments, R 3 and R 5 is H, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, halogen, CN, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 independently selected from alkylcarbonyl and hydroxy; 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6Alkenyl, C 2-6 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen and CN, preferably R 3 and R 5 is H, C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 independently selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen; and R 4 is H, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6Alkoxy-C 1-6 Alkoxy, halogen, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 selected from alkylcarbonyl and hydroxy; 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen and CN, preferably R 4 is H, C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6Cycloalkyl-C 1-3 selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen.

[0161] R 1 , R 2a , R 2b , R 2c , R 3 , J., G., R. 3 , R 4 and R 5 The preferences for are the same as the preferences given for the corresponding substituents of the compounds of formula (I).

[0162] In a more preferred embodiment according to the compounds of formula (II), R 4 is H, C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 independently selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Each of the alkyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen; and / or X is Cl or I.

[0163] Formula (XVII) [ka] (In the formula, R 1 is C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl, C 1-4 alkoxy and CN; 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl and C 1-4 Each of the alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogen and CN; R 2a , R 2b and R 2c is H, hydroxy, halogen, CN, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6Alkoxy, amino and NHC(O)C 1-6 alkyl, preferably R 2a , R 2b and R 2c H, halogen, CN, C 1-4 Alkyl and C 1-4 independently selected from alkoxy; J is for CR 4 or N; G is CR 5 or N; If J is N, then G is CR 5 and when G is N, J is CR 4 and R 3 , R 4 and R 5 is H, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, halogen, CN, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 independently selected from alkylcarbonyl and hydroxy; 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-6 Cycloalkyl, C 3-6Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen and CN, preferably R 3 , R 4 and R 5 is H, C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 independently selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen. Compound.

[0164] R 1 , R 2a , R 2b , R 2c , R 3 , J., G., R. 3 , R 4 and R5 The preferences for are the same as the preferences given for the corresponding substituents of the compounds of formula (I).

[0165] In a more preferred embodiment according to the compounds of formula (XVII), R 3 , R 4 and R 5 At least one of the is not H, more specifically, -R 3 and R 4 is C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 independently selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen; and -R 5 is H, C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C1-3 selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen.

[0166] In another more preferred embodiment according to the compound of formula (XVII), -R 3 is H, C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, F, Br, I, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen; and -R 4 and R 5 is H, C 1-4 Alkyl, C 1-4 Alkoxy, C1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 independently selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen. 3 and R 4 is more specifically not Cl.

[0167] In another more preferred embodiment according to the compound of formula (XVII), -R 3 is C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, F, Br, I, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen; and -R 4 and R 5 is H, C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 independently selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen. 3 and R 5 is more specifically not Cl.

[0168] The compounds of formula (I) as defined in any one of embodiments 1 to 43 can be used in the agricultural sector and related fields of use, for example, as active ingredients for controlling plant pests or non-living materials, or for controlling spoilage microorganisms or organisms potentially harmful to humans. The novel compounds are distinguished by their excellent activity at low application rates, their good tolerance by plants, and their environmental safety. They possess highly useful curative, preventive, and systemic properties and can be used to protect many cultivated plants. The compounds of formula (I) as defined in any one of embodiments 1 to 43 can be used to inhibit or eliminate pests occurring on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of different crops of useful plants, while simultaneously protecting these parts of later-developing plants from, for example, phytopathogenic microorganisms.

[0169] The compounds of formula (I) defined in any one of embodiments 1 to 43 may also be used as fungicides. The term "fungicide" as used herein means a compound that controls, modifies or prevents the growth of fungi. The term "fungicidally effective amount" means the amount of such a compound or combination of such compounds that is capable of producing an effect on fungal growth. A controlling or modifying effect includes any deviation from natural development such as killing, retardation, etc., and prevention includes the formation of a barrier or other defense in the plant to prevent infection by the fungus.

[0170] The compounds of formula (I) as defined in any one of embodiments 1 to 43 can also be used as dressings to treat plant propagation material, e.g., seeds such as fruits, tubers, or grains, or plant cuttings (e.g., rice), for protection against fungal infections and phytopathogenic fungi occurring in the soil. The propagation material can be treated with a composition comprising a compound of formula (I) as defined in any one of embodiments 1 to 43 before planting. For example, seeds can be dressed before being sown. The compounds of formula (I) as defined in any one of embodiments 1 to 43 can also be applied to grains (coatings) by impregnating the seeds in a liquid formulation or coating the seeds with a solid formulation. The composition can also be applied to the planting site when the propagation material is planted, e.g., in the sowing furrow during sowing. The present invention also relates to methods for treating such plant propagation material and to the plant propagation material thus treated.

[0171] Furthermore, the compounds of formula (I) as defined in any one of embodiments 1 to 43 may be used for controlling fungi, for example in the protection of industrial materials, including wood and wood-based industrial products, food storage, hygiene and other related fields.

[0172] In addition, the present invention may be used to protect non-living materials such as timber, wallboard and paint from fungal attack.

[0173] The compounds of formula (I) as defined in any one of embodiments 1 to 43 and fungicidal compositions containing them may be used to control plant diseases caused by a wide range of fungal plant pathogens, and are effective in controlling a wide range of plant diseases, including foliar pathogens of ornamental crops, turf, vegetables, field crops, cereals and fruit crops.

[0174] The fungi and fungal vectors as well as phytopathogenic bacteria and viruses associated with these diseases that can be controlled 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, Blumeria graminis, Bremia lactucae Botryosphaeria spp. including B. lactucae, B. dothidea, and B. obtusa, Botrytis spp. including B. cinerea, C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, and C. tropicalis, Candida spp., Cephaloascus fragrans, and 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., Erysiphe spp., including Epidermophyton spp., Erwinia amylovora, and E. cichoracearum; Fusarium spp., including Eutypa lata, F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, and F. solani, Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, and Glomerella cinquefolia. cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Helminthosporium spp., Hemileia spp., Histoplasma spp. including H. capsulatum, Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochium nivale, Microsporum spp. spp.), Monilinia spp., Mucor spp., Mycosphaerella spp., including M. graminicola and M. pomi.), Oncobasidium theobromaeon, Ophiostoma piceae, Paracoccidioides spp., Penicillium spp. including P. digitatum, P. italicum, Petriellidium spp., Peronosclerospora spp. including P. maydis, P. philippinensis and P. sorghi, Peronosclerospora spp., Peronospora spp., Phaeosphaeria nodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp., Phoma spp., Phomopsis viticola, Phytophthora spp. including P. infestans, Plasmopara spp. including P. halstedii and P. viticola, Pleospora spp., Podosphaera spp. including P. leucotricha, Polymyxa graminis graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp., Pseudoperonospora spp. including P. cubensis and P. humuli.), Puccinia spp. including Pseudopeziza 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 pusillus, Rhizopus arrhizus, Rhynchosporium spp., Scedosporium spp. including S. apiospermum and S. prolificans, Schizothyrium pomi, Sclerotinia spp., Sclerotium spp., Septoria spp. including S. nodorum, S. tritici, Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp., Stagonospora nodorum, Stempphylium spp., Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola 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.

[0175] In particular, the compounds of formula (I) as defined in any one of embodiments 1 to 43 and fungicidal compositions containing them can be used to control plant diseases caused by a wide range of fungal plant pathogens in the classes Basidiomycete, Ascomycete, Oomycete and / or Deuteromycete, Blasocladiomycete, Chrytidiomycete, Glomeromycete and / or Mucoromycete. More specifically, the compounds of formula (I) as defined in any one of embodiments 1 to 43 can be used to control oomycetes.

[0176] These pathogens may include: The class Oomycete includes: Phytophthora diseases such as those caused by Phytophthora capsici, Phytophthora infestans, Phytophthora sojae, Phytophthora fragariae, Phytophthora nicotianae, Phytophthora cinnamomi, Phytophthora citricola, Phytophthora citrophthora and Phytophthora erythroseptica; Pythium aphanidermatum, Pythium arrhenoides Pythium diseases such as those caused by P. arrhenomanes, Pythium graminicola, Pythium irregulare, Pythium sylvaticum and Pythium ultimum; Peronospora destructor, Peronospora parasitica, Plasmopara viticola, Plasmopara halstedii, Pseudoperonospora cubensis, Albugo candida, Sclerophthora macrospora and Bremia lactucae Diseases caused by Peronosporales such as lactucae;and others such as Aphanomyces cochlioides, Labyrinthula zosterae, Peronosclerospora sorghi and Sclerospora graminicola;

[0177] Ascomycetes, such as Stemphylium solani, Stagonospora tainanensis, Spilocaea oleaginea, Setosphaeria turcica, Pyrenochaeta lycoperisici, Pleospora herbarum, Phoma destructiva, Phaeosphaeria herpotrichoides, Phaeocryptocus gaeumannii, Ophiosphaerella graminicola, Ophiobolus graminis, graminis, Leptosphaeria maculans, Hendersonia creberrima, Helminthosporium triticirepentis, Setosphaeria turcica, Drechslera glycines, Didymella bryoniae, Cycloconium oleagineum, Corynespora cassiicola, Cochliobolus sativus, Bipolaris cactivora, Venturia inaequalis, Pyrenophora teres), wheat yellow spot fungus (Pyrenophora tritici-repentis), Alternaria alternata, Alternaria brassicicolaPleosporales, such as Septoria brassicicola, Alternaria solani, and Alternaria tomatophila; Capnodiales, such as Septoria tritici, Septoria nodorum, Septoria glycines, Cercospora arachidicola, Cercospora sojina, Cercospora zeae-maydis, Cercosporella capsellae, and Cercosporella herpotrichoides; Cladosporium carpophyllum, carpophilum, Cladosporium effusum, Passalora fulva, Cladosporium oxysporum, Dothistroma septosporum, Isariopsis clavispora, Mycosphaerella fijiensis, Mycosphaerella graminicola, Mycovellosiella koepkeii, Phaeoisariopsis bataticola, Pseudocercospora vitis, Pseudocercosporella herpotrichoides herpotrichoides, Ramularia beticola, Ramularia collo-cygni, Gaeumannomyces graminisMagnaporthales such as Magnaporthe grisea, Pyricularia oryzae, Anisogramma anomala, Apiognomonia errabunda, Cytospora platani, Diaporthe phaseolorum, Discula destructiva, Gnomonia fructicola, Greeneria uvicola, Melanconium juglandinum, Phomopsis viticola, Sirococcus clavigignenti-Juglandacearum, and others. Diaporthales, such as Tubakia dryina, Dicarpella spp., and Valsa ceratosperma; as well as Actinothyrium graminis, Ascochyta pisi, Aspergillus flavus, Aspergillus fumigatus, Aspergillus nidulans, Asperisporium caricae, Blumeriella jaapii, Candida spp., and Capnodium ramosum. ramosum, Cephaloascus spp., Cephalosporium gramineum, Ceratocystis paradoxaparadoxa, Chaetomium spp., Hymenoscyphus pseudoalbidus, Coccidioides spp., Cylindrosporium padi, Diplocarpon malae, Drepanopeziza campestris, Elsinoe ampelina, Epicoccum nigrum, Epidermophyton spp., Eutypa lata, Geotrichum candidum, Gibellina cerealis cerealis), Gloeocercospora sorghi, Gloeodes pomigena, Gloeosporium perennans blotch, spot, blast or blight and / or rot diseases such as those caused by others such as Gloeotinia temulenta, Griphospaeria corticola, Kabatiella lini, Leptographium microsporum, Leptosphaerulinia crassiasca, Lophodermium seditiosum, Marssonina graminicola, Microdochium nivale, Monilinia fructicola, Monographella albescens, Monosporascus canonvales, cannonballus, Naemacyclus spp., Ophiostomanovo-ulmi, Paracoccidioides brasiliensis, Penicillium expansum, Pestalotia rhododendri, Petriellidium spp., Pezicula spp., Phialophora gregata, Phyllachora pomigena, Phymatotrichum omnivora, Physalospora abdita, Plectosporium tabacinum tabacinum, Polyscytalum pustulans, Pseudopeziza medicaginis, Pyrenopeziza brassicaebrassicae, Ramulispora sorghi, Rhabdocline pseudotsugae, Rhynchosporium secalis, Sacrocladium oryzae, Scedosporium spp., Schizothyrium pomi, Sclerotinia sclerotiorum, Sclerotinia minor; Sclerotium spp., Typhula ishikariensis, Seimatosporium mariae, Lepteutypa cupressi, Septocyta ruborum, Sphaceloma perseae, Sporonema phacidioides, Stigmina palmivora, Tapesia yallundae, Taphrina bullata, Thielviopsis basicola, Trichoseptoria fructigena, Zygophiala jamaicensis; e.g. Blumeria graminis, Erysiphe polygoni, Uncinula necator, Sphaerotheca fuligena), apple powdery mildew (Podosphaera leucotricha), Podospaera macularis, Golovinomyces cichoracearum, Leveillula tauricaPowdery mildew diseases, such as those caused by Erysiphales, such as Microsphaera diffusa, Oidiopsis gossypii, Phyllactinia guttata and Oidium arachidis; powdery mildew diseases, such as those caused by Dothiorella aromatica, Diplodia seriata, Guignardia bidwellii, Botrytis cinerea, Botryotinia allii, Botryotinia fabae, Fusicoccum amygdali, fungi, such as those caused by the Botryosphaeriales, such as A. amygdali, Lasiodiplodia theobromae, Macrophoma theicola, Macrophomina phaseolina, Phyllosticta cucurbitacearum; for example Colletotrichum gloeosporioides, Colletotrichum lagenarium, Colletotrichum gossypii, Glomerella cingulata and Colletotrichum graminicola; anthracnose, such as those caused by Glommerelales, such as Acremonium strictum, Claviceps purpurea, Fusarium culmorum,culmorum, Fusarium graminearum, Fusarium virguliforme, Fusarium oxysporum, Fusarium subglutinans, Fusarium oxysporum f.sp.cubense, Gerlachia nivale, Gibberella fujikuroi, Gibberella zeae, Gliocladium spp., Myrothecium verrucaria, Nectria ramulariae, Trichoderma viride Wilt or blight diseases such as those caused by Hypocreales such as Trichothecium viride, Trichothecium roseum and Verticillium theobromae.

[0178] Basidiomycete, including smut fungi such as those caused by species of the Ustilaginales, e.g., Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, and Ustilago zeae, e.g., Cerotelium fici, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, and Puccinia graminis. graminis, Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia striiformis f.sp.Hordei, Puccinia striiformis f.sp.rust fungi such as those caused by the Uredinales, such as Cronartium ribicola, Gymnosporangium juniperi-viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor and Uromyces viciae-fabae; and Cryptococcus sp. spp.), Exobasidium vexans, Marasmiellus inoderma, Mycena spp., Sphacelotheca reiliana, Typhula ishikariensis, Urocystis agropyri, Itersonilia perplexans, Corticium invisum, Laetisaria fuciformis, Waitea circinata, Rhizoctonia solani, Thanetephorus cucurmeris, Entyloma Other decays and diseases such as those caused by Bacillus dahliae, Entylomella microspora, Neovossia moliniae and Tilletia caries.

[0179] Blastocladiomycetes, including Physoderma maydis.

[0180] Mucoromycetes, such as Choanephora cucurbitarum; Mucor spp.; and Rhizopus arrhizus. and diseases caused by other species and genera closely related to those listed above.

[0181] In addition to their bactericidal / fungicidal activity, the compounds of formula (I) as defined in any one of embodiments 1 to 43 and compositions containing them may also have activity against bacteria such as Erwinia amylovora, Erwinia caratovora, Xanthomonas campestris, Pseudomonas syringae, Strptomyces scabies and other related species, as well as certain protozoa.

[0182] Within the scope of the present invention, the target crops and / or useful plants to be protected are typically berry plants, such as blackberries, blueberries, cranberries, raspberries and strawberries; cereals, such as barley, maize (corn), millet, oats, rice, rye, sorghum, triticale and wheat; 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; 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, olive and rubber; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumber, garlic, lettuce, squash, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and perennial and annual crops such as vines.

[0183] Useful plants and / or target crops according to the present invention include conventional varieties and genetically enhanced or engineered varieties, such as insect-resistant (e.g., Bt. and VIP varieties), disease-resistant, herbicide-tolerant (e.g., glyphosate- and glufosinate-tolerant corn varieties available commercially under the trade names RoundupReady® and LibertyLink®), and nematode-resistant varieties. By way of example, suitable genetically enhanced or engineered varieties include Stoneville 5599BR cotton and Stoneville 4892BR cotton varieties.

[0184] The terms "useful plants" and / or "target crops" should also be understood to include useful plants that have been rendered tolerant to herbicides such as bromoxynil or to 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 breeding or genetic engineering methods. An example of a crop that has been rendered tolerant to imidazolinones, such as imazamox, by conventional breeding methods (mutagenesis) is Clearfield® summer rapeseed (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®.

[0185] The terms "useful plants" and / or "target crops" should be understood to include those that are naturally occurring or have been engineered to resist harmful insects. This includes plants that have been transformed, for example, using recombinant DNA technology, to have the ability to synthesize one or more selectively acting toxins, such as those known to be derived from toxin-producing bacteria. Examples of toxins that can be expressed include delta-endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins of nematode-symbiotic bacteria, and toxins produced by scorpions, arachnids, wasps, and fungi. One example of a crop modified to express Bacillus thuringiensis toxins is Bt maize KnockOut® (Syngenta Seeds). One example of a crop containing two or more genes encoding insecticide resistance and thus expressing two or more toxins is VipCot® (Syngenta Seeds). Crops or their seed material can also be resistant to multiple pests (so-called overlapping transgenic events when created by genetic modification). For example, a plant can be herbicide-resistant and at the same time capable of expressing an insecticidal protein, such as Herculex I® (Dow AgroSciences, Pioneer Hi-Bred International).

[0186] The terms "useful plants" and / or "target crops" should also be understood to include useful plants that have been transformed using recombinant DNA techniques so as to be able to synthesize antipathogenic substances with selective action, such as, for example, so-called "infection-specific proteins" (PRPs, see, for example, EP-A-0 392 225). Examples of such antipathogenic substances and transformed plants capable of synthesizing such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95 / 33818 and EP-A-0 353 191. Methods for producing such transformed plants are generally known to those skilled in the art and are described, for example, in the above-mentioned publications.

[0187] Toxins that can be expressed by the transformed plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as δ-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 such as Photorhabdus luminescens, Xenorhabdus nematophilus, e.g., Photorhabdus spp. or Xenorhabdus spp. 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.

[0188] 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 understood to also refer to, inter alia, 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, a non-naturally occurring protease recognition sequence is preferably inserted into the toxin, for example, in the case of Cry3A055, a cathepsin-G recognition sequence is inserted into the Cry3A toxin (see WO 03 / 018810).

[0189] Further examples of such toxins or transformed plants capable of synthesizing such toxins are disclosed, for example, in EP 0 374 753, WO 93 / 07278, WO 95 / 34656, EP 0 427 529, EP 451 878 and WO 03 / 052073.

[0190] Processes for the preparation of such transformed 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.

[0191] The toxins contained in the transformed plants confer resistance to harmful insects on the plants, which can be of any insect taxonomic group, but are particularly commonly found in beetles (Coleoptera), two-winged insects (Diptera), and butterflies (Lepidoptera).

[0192] 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®.

[0193] Further examples of such transformed crops are as follows:

[0194] 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) that is resistant to European corn borers (Ostrinia nubilalis and Sesamia nonagrioides) through the transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also achieves tolerance to the herbicide glufosinate-ammonium through the transgenic expression of the enzyme PAT.

[0195] 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) that confers resistance to European corn borers (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.

[0196] 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. Maize conferred insect resistance by transgenic expression of a modified Cry3A toxin. The toxin is Cry3A055 modified by the insertion of a cathepsin-G-proteinase recognition sequence. The preparation of such transformed maize plants is described in WO 03 / 018810.

[0197] 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 coleopteran insects.

[0198] 5. IPC531 Cotton, registration number C / ES / 96 / 02, manufactured by Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium.

[0199] 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 lepidopteran insects and the protein PAT to achieve tolerance to the herbicide glufosinate ammonium.

[0200] 7. NK603 x MON810 corn, registration number C / GB / 02 / M3 / 03, manufactured by Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. This conventional hybrid corn variety is the result of crossing the genetically engineered varieties NK603 and MON810. NK603 x MON810 corn 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.

[0201] As used herein, the term "habitat" means the field in which the plant is growing, or the field in which the seeds of the cultivated plant have been sown, or the field in which the seeds will be sown in soil. It includes the soil, seeds and seedlings, and established vegetation.

[0202] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, seedlings, roots, tubers, stems, stalks, foliage, and fruits.

[0203] The term "plant propagation material" is understood to refer to reproductive parts of plants, such as seeds, that can be used for their propagation, as well as vegetative bodies, such as cuttings or tubers, e.g., potatoes. For example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, and plant parts may be mentioned. Also included are sprouted plants and shoots that will be transplanted after germination or emergence from the soil. These shoots may be protected by a complete or partial treatment by immersion before transplantation. Preferably, "plant propagation material" is understood to refer to seeds.

[0204] The pesticides referred to herein using their common names are known, for example, from "The Pesticide Manual", 19th Ed., British Crop Protection Council 2021.

[0205] The compounds of formula (I) defined in any one of embodiments 1 to 43 can be used in their pure form or, preferably, together with adjuvants conventionally employed in the formulation art. 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, are selected depending on the intended purpose and the current situation. The compositions may also contain further adjuvants, such as stabilizers, antifoaming agents, viscosity modifiers, binders or adhesives, and fertilizers, trace element sources, or other compounds for achieving special effects.

[0206] For example, suitable carriers and / or adjuvants for use in agriculture may be solid or liquid and are substances useful in formulation technology, such as natural or regenerated mineral substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders or fertilizers. Such carriers are described, for example, in WO 97 / 33890.

[0207] Suspension concentrates are aqueous formulations in which fine solid particles of the active compound are suspended. Such formulations contain anti-settling and dispersing agents, and may also contain wetting agents to enhance activity, as well as anti-foaming and crystal growth inhibitors. For use, these concentrates are diluted in water and typically applied by spray to the area to be treated. The amount of active ingredient can range from 0.5% to 95% of the concentrate.

[0208] Wettable powders are in the form of fine particles that disperse readily in water or other liquid carriers. These particles contain the active ingredient held in a solid matrix. Typical solid matrices include Fuller's earth, kaolin clay, silica, and other 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.

[0209] Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquids. They may consist solely of the active compound and a liquid or solid emulsifier, or may contain a liquid carrier such as xylene, high-boiling aromatic naphtha, isophorone, and other nonvolatile organic solvents. In use, these concentrates are dispersed in water or other liquid and typically applied by spraying to the area to be treated. The amount of active ingredient can range from 0.5% to 95% of the concentrate.

[0210] 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, plaster of Paris, 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 typically 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 spreading agents such as dextrin, glue, or synthetic resins.

[0211] Dusts are free-flowing admixtures of the active ingredient and finely divided solids such as talc, clays, powders and other organic and inorganic solids which act as dispersants and carriers.

[0212] Microcapsules are typically small 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 comprises 50 to 95% of the capsule's weight and may contain a solvent in addition to the active compound. Encapsulated granules are generally porous granules with a porous membrane that seals the pore openings of the granule and retains the active species in liquid form within the pores of the granule. 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 natural. Examples of such materials are vermiculite, calcined clay, kaolin, attapulgite clay, sawdust, and granular carbon. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitrile, polyacrylates, polyesters, polyamides, polyureas, polyurethanes, and starch xandates.

[0213] Other useful formulations for agricultural chemical applications include simple solutions of the active ingredient in solvents such as acetone, alkylated naphthalenes, xylene, and other organic solvents, in which complete dissolution at the desired concentration is achieved. Pressurized sprayers can also be used, in which the active ingredient is dispersed in finely divided form as the low-boiling dispersant solvent carrier evaporates.

[0214] Suitable agricultural adjuvants and / or carriers useful in formulating the compositions of the present invention in the formulation types described above are well known to those skilled in the art.

[0215] Liquid carriers that may be used include, for example, water, toluene, xylene, petroleum naphtha oil, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, 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-octylamine, kutade Examples of suitable additives include citric 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 amyl alcohol, tetrahydrofurfuryl alcohol, high molecular weight alcohols such as hexanol, octanol, ethylene glycol, propylene glycol, glycerin, and N-methyl-2-pyrrolidinone. For dilution of concentrates, water is typically the carrier of choice.

[0216] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, Kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut hulls, and lignin.

[0217] A wide range of surfactants are advantageously employed in both the liquid and solid compositions, particularly those designed to be diluted with a carrier before application. These surfactants, when used, typically comprise from 0.1% to 15% by weight of the formulation. They may be anionic, cationic, nonionic, or polymeric in nature and may be used as emulsifying agents, wetting agents, suspending agents, or for other purposes. Typical surfactants include alkyl sulfates such as diethanolammonium lauryl sulfate; alkylaryl sulfonate salts such as calcium dodecylbenzene sulfonate; alkylphenol-alkylene oxide adducts such as nonylphenol-C.sub.18 ethoxylate; alcohol-alkylene oxide adducts such as tridecyl alcohol-C.sub.16 ethoxylate; soaps such as sodium stearate; alkylnaphthalene sulfonates such as sodium dibutylnaphthalene sulfonate; dialkyl esters of sulfosuccinates such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters such as sorbitol oleate; quaternary amines such as lauryltrimethylammonium chloride; polyethylene glycol esters of fatty acids such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and di-alkyl phosphate esters.

[0218] Other adjuvants commonly utilized in agricultural compositions include crystallization inhibitors, viscosity modifiers, suspending agents, spray size regulators, 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, trace elements, emollients, lubricants, and adhesives.

[0219] In addition, other biocidal active ingredients or compositions may be combined with the compositions of the present invention, used in the methods of the present invention, and applied simultaneously or sequentially with the compositions of the present invention. When applied simultaneously, these additional active ingredients may be formulated together with the compositions of the present invention or mixed together, for example, in a spray tank. These additional biocidal active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides, plant growth regulators, and / or biological agents.

[0220] The following mixtures of compounds of formula I with active ingredients are preferred (the abbreviation "TX" means "one compound selected from the compounds defined in Tables 1.1 to 1.36" or "one compound selected from the compounds defined in Table A"): Petroleum (alternative name) (628) + TX; Abamectin + TX, Acequinocyl + TX, Acetamiprid + TX, Acetoprole + TX, Acrinathrin + TX, Acinonapyr + TX, Afidopiropen + TX, Afoxolaner + TX, Alanycarb + TX, Allethrin + TX, α-Cypermethrin + TX, Alphamethrin + TX, Amidoflumet + TX, Aminocarb + TX, Azocyclotine + TX, Bensultap + TX, Benzoximate + TX, Benzpyrimoxane + TX, Beta-Cyfluthrin + TX, β-Cypermethrin + TX, Bifenazepam olate +TX, bifenthrin +TX, binapacryl +TX, bioallethrin +TX, S-bioallethrin +TX, bioresmethrin +TX, bistrifluron +TX, broflunilide +TX, brofluthrinate +TX, bromophos-ethyl +TX, buprofezin +TX, butocarboxim +TX, cadusafos +TX, carbaryl +TX, carbosulfan +TX, cartap +TX, CAS No. 1632218-00-8 +TX, CAS No. 1808115-49-2 +TX, CAS No. 2032403-97-5 +TX, CAS No. 20447 01-44-0+TX, CAS number 2128706-05-6+TX, CAS number 2095470-94-1+TX, CAS number 2377084-09-6+TX, CAS number 1445683-71-5+TX, CAS number 2408220-94-8+TX, CAS number 24 08220-91-5+TX, CAS number 1365070-72-9+TX, CAS number 2171099-09-3+TX, CAS number 2396747-83-2+TX, CAS number 2133042-31-4+TX, CAS number 2133042-44-9+TX, CAS number 1445684-82-1+TX, CAS number 1445684-82-1+TX, CAS number 1922957-45-6+TX, CAS number 1922957-46-7+TX, CAS number 1922957-47-8+TX, CAS number 1922957-48-9+TX, CA S number 2415706-16-8+TX, CAS number 1594624-87-9+TX, CAS number 1594637-65-6+TX, CAS number 1594626-19-3+TX, CAS number 1990457-52-7+TX, CAS number 1990457-55-0+TX,CAS No. 1990457-57-2+TX, CAS No. 1990457-77-6+TX, CAS No. 1990457-66-3+TX, CAS No. 1990457-85-6+TX, CAS No. 2220132-55-6+TX, CAS No. 1255091-74-7+TX, CAS No. RNA (Colorado potato beetle (Leptinotarsa decemlineata)-specific recombinant double-stranded interference (GS2) + TX, CAS No. 2719848-60-7 + TX, CAS No. 1956329-03-5 + TX, chlorantraniliprole + TX, chlordane + TX, chlorfenapyr + TX, chlorprallethrin + TX, chromafenozide + TX, clenpirin + TX, cloetocarb + TX, clothianidin + TX, 2-chlorophenyl N-methylcarbamate (CPMC) + TX, cyanofenphos + TX , cyantraniliprole + TX, cycloniliprole + TX, cyclobutrifluram + TX, cycloprothrin + TX, cycloxapride + TX, cyenopyrafen + TX, cyetopyrafen (or ethopyrafen) + TX, cyflumetofen + TX, cyfluthrin + TX, cyhalodiamide + TX, cyhalothrin + TX, cypermethrin + TX, cyphenothrin + TX, cyprofuranilide + TX, cyromazine + TX, deltamethrin + TX, diafenthiuron + TX, Dialifos + TX, Dibrom + TX, Dichloromezothiaz + TX, Diflobidazin + TX, Diflubenzuron + TX, Dimpropyridaz + TX, Dinactin + TX, Dinocap + TX, Dinotefuran + TX, Dioxabenzophos + TX, Emamectin (or Emamectin benzoate) + TX, Empenthrin + TX, ε-Monfluorotrin + TX, ε-Metofluthrin + TX, Esfenvalerate + TX, Ethion + TX, Ethiprole + TX, Ethofen Enprox + TX, Etoxazole + TX, Fanfar + TX, Fenazaquin + TX, Fenfluthrin + TX, Fenmezodithiaz + TX, Fenitrothion + TX, Fenobucarb + TX, Fenothiocarb + TX, Fenoxycarb + TX, Fenpropathrin + TX, Fenpyroximate + TX, Fensulfothion + TX, Fenthion + TX, Fentin acetate + TX, Fenvalerate + TX, Fipronil + TX, Flometoquin + TX,Flonicamid +TX, Fluacrypyrim +TX, Fluazaindolizine +TX, Fluazuron +TX, Flubendiamide +TX, Flubenzimine +TX, Fluclodiniliprole +TX, Flucythrinate +TX, Flucycloxuron +TX, Flucythrinate +TX, Fluensulfone +TX, Flufenerim +TX, Flufenprox +TX, Flufiprole +TX, Fluhexafon +TX, Flumethrin +TX, Fluopyram +TX, Flupentiofenox +TX, Flupyradifurone +TX, Flupirimine +TX, Fluralaner +TX, Fluvalinate + TX, fluxamethamide + TX, fosthiazate + TX, gamma-cyhalothrin + TX, guadipyr + TX, halofenozide + TX, halfenprox + TX, heptafluthrin + TX, hexythiazox + TX, hydramethylnon + TX, imicyafos + TX, imidacloprid + TX, imiprothrin + TX, indazapiroxamet + TX, indoxacarb + TX, iodomethane + TX, iprodione + TX, isocycloceram + TX, isothioate + TX, ivermectin + TX, kappa-bifenthrin + TX, kappa-teflutri flumethrin + TX, λ-cyhalothrin + TX, lepimectin + TX, lotilaner + TX, lufenuron + TX, metaflumizone + TX, metaldehyde + TX, metam + TX, methomyl + TX, methoxyfenozide + TX, metofluthrin + TX, metolcarb + TX, mexacarbate + TX, milbemectin + TX, momfluorotrin + TX, niclosamide + TX, nicofluprole + TX; nitenpyram + TX, nithiazine + TX, omethoate + TX, oxamyl + TX, oxazosulfil + TX, parathion-ethyl + TX, permethrin + TX, flumethrin Enthrin + TX, phosphocarb + TX, piperonyl butoxide + TX, pirimicarb + TX, pirimiphos-ethyl + TX, pirimiphos-methyl + TX, polyhedrosis virus + TX, prallethrin + TX, profenofos + TX, profluthrin + TX, propargite + TX, propetamphos + TX, propoxur + TX, prothiofos + TX, protrifenbut + TX, piflubumid + TX, pymetrozine + TX, pyraclofos + TX, pyrafluprole + TX, pyridaben + TX, pyridalyl + TX, pyrifluquinazon + TX, pyrimidifen + TX,Pyriminostrobin +TX, pyriprole +TX, pyriproxyfen +TX, resmethrin +TX, sarolaner +TX, selamectin +TX, silafluofen +TX, spinetoram +TX, spinosad +TX, spirobudifen +TX; spirodiclofen +TX, spiromesifen +TX, spiropydione +TX, spirotetramat +TX, spidoxamat +TX, sulfoxaflor +TX, tebufenozide +TX, tebufenpyrad +TX, tebupirimiphos +TX, tefluthrin +TX, temephos +TX, tetrachlorantraniliprole +TX, tetradifon +TX, tetramethrin +TX, tetramethylfluthrin +TX, tetranactin +TX, tetraniliprole +TX, θ-cypermethrin +TX, thiacloprid +TX, thiamethoxam +TX, thiocyclam +TX, thiodicarb +TX, thiof Fanox +TX, Thiometon +TX, Thiosultap +TX, Tigolaner +TX, Thiolantraniliprole +TX; Thioxazaphen +TX, Tolfenpyrad +TX, Toxaphene +TX, Tralomethrin +TX, Transfluthrin +TX, Triazamate +TX, Triazophos +TX, Trichlorfon +TX, Trichloronate +TX, Trichlorfon +TX, Trifluenfuronate +TX, Triflumezopyrim +TX, Cyclopyrazoflurane +TX, Zeta-cypermethrin +TX, Seaweed extract and Melasse-derived fermentation product +TX, Seaweed extract and Melasse-derived fermentation product containing urea +TX, Amino acids +TX, Potassium and molybdenum and EDTA-chelated manganese +TX, Seaweed extract and plant fermentation product +TX, Seaweed extract and plant fermentation product containing plant hormones +TX, Vitamins +TX, EDTA-chelated copper +TX, Zinc + TX, iron + TX, azadirachtin + TX, Bacillus aizawai + TX, Bacillus chitinosporus AQ746 (NRRL accession number B-21618) + TX, Bacillus firmus + TX, Bacillus kurstaki + TX, Bacillus mycoides AQ726 (NRRL accession number B-21664) + TX, Bacillus pumilus (NRRL accession number B-30087) + TX, Bacillus pumilus AQ717 (NRRL accession number B-21662) + TX, Bacillus species sp.) AQ178 (ATCC accession number 53522) + TX, Bacillus sp.) AQ175 (ATCC accession number 55608) + TX, Bacillus sp.) AQ177 (ATCC accession number 55609) + TX, Bacillus subtilis unspecified + TX, Bacillus subtilis AQ153 (ATCC accession number 55614) + TX, Bacillus subtilis AQ30002 (NRRL accession number B-50421) + TX, Bacillus subtilis AQ30004 (NRRL accession number B-50455) + TX, Bacillus subtilis AQ713 (NRRL accession number B-21661) + TX, Bacillus subtilis AQ743 (NRRL accession number B-21665) + TX, Bacillus thuringiensis thuringiensis AQ52 (NRRL accession number B-21619) + TX, Bacillus thuringiensis BD♯32 (NRRL accession number B-21530) + TX, Bacillus thuringiensis subsp. kurstaki BMP123 + TX, Beauveria bassiana + TX, D-limonene + TX, Granulovirus + TX, Harpin + TX, Helicoverpa armigera nuclear polyhedron virus + TX, Helicoverpa zea nuclear polyhedron virus + TX, Heliothis virescens nuclear polyhedron virus + TX, Heliothis punctatus punctigera) nuclear polyhedrovirus + TX, Metarhizium spp.) + TX, Muscodor albus 620 (NRRL Accession No. 30547) + TX, Muscodor roseus A3-5 (NRRL Accession No. 30548) + TX, Neem Wood-Based Products + TX, Paecilomyces fumosoroseus + TX, Paecilomyces lilacinus + TX, Pasteuria nishizawae + TX, Pasteuria penetrans + TX, Pasteuria ramosa + TX, Pasteuria thornei + TX, Pasteuria usgae + TX, P-cymene + TX, Plutella xylostella xylostella granulosis virus + TX, Plutella xylostella nucleopolyhedrovirus + TX, polyhedrosis virus + TX, pyrethrum + TX, QRD420 (terpenoid blend) + TX, QRD452 (terpenoid blend) + TX, QRD460 (terpenoid blend) + TX, Quillaja saponaria + TX, Rhodococcus globerulus AQ719 (NRRL accession number B-21663) + TX, Spodoptera frugiperda nucleopolyhedrovirus + TX, Streptomyces galbus (NRRL accession number 30232) + TX, Streptomyces species an adjuvant selected from the group consisting of Verticillium spp. (NRRL Accession No. B-30145) + TX, terpenoid blend + TX, and Verticillium spp. + TX; an algicide selected from the group consisting of bethoxadin [CCN] + TX, copper dioctanoate (IUPAC name) (170) + TX, copper sulfate (172) + TX, sibutrin [CCN] + TX, dichloron (1052) + TX, dichlorophen (232) + TX, endothal (295) + TX, fentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinoneamide (1379) + TX, simazine (730) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX; an anthelmintic selected from the group of substances consisting of abamectin (1) + TX, crufomate (1011) + TX, cyclobutrifluram + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, epirinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) and thiophanate (1435) + TX; an avian repellent selected from the group consisting of chloralose (127) + TX, endrin (1122) + TX, fenthion (346) + TX, pyridin-4-amine (IUPAC name) (23) and strychnine (745) + TX; 1-Hydroxy-1H-pyridine-2-thione (IUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (IUPAC name) (170) + TX, copper hydroxide (IUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophen (232) + TX, dipyrithione (1105) + TX, doditin (1112) + TX, fenaminosulf (1144) + TX, formaldehyde (404) + TX, hydrargafen (alternative name) [CCN] + TX, kasugama a bactericide selected from the group consisting of isin (483) + TX, kasugamycin hydrochloride hydrate (483) + TX, nickel bis(dimethyldithiocarbamate) (IUPAC name) (1308) + TX, nitrapyrin (580) + TX, octhilinone (590) + TX, oxolinic acid (606) + TX, oxytetracycline (611) + TX, potassium hydroxyquinoline sulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, streptomycin sesquisulfate (744) + TX, tecloftalam (766) + TX, and thiomersal (alternative name) [CCN] + TX; Adoxophyes orana GV (alternate name) (12) + TX, Agrobacterium radiobacter (alternate name) (13) + TX, Amblyseius spp. (alternate name) (19) + TX, Anagrapha falcifera NPV (alternate name) (28) + TX, Anagrus atomus (alternate name) (29) + TX, Aphelinus abdominalis (alternate name) (33) + TX, Aphidius colemani (alternate name) (34) + TX, Aphidoletes aphidimyza (alternate name) (35) + TX, Autographa californica NPV (alternative name) (38) + TX, Bacillus firmus (alternative name) (48) + TX, Bacillus sphaericus Neide (scientific name) (49) + TX, Bacillus thuringiensis Berliner (scientific name) (51) + TX, Bacillus thuringiensis subsp. aizawai (scientific name) (51) + TX, Bacillus thuringiensis subsp. israelensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. japonensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. kurstaki) (scientific name) (51) + TX, Bacillus thuringiensis (Bacillus thuringiensis subsp.tenebrionis (scientific name) (51) + TX, Beauveria bassiana (alternate name) (53) + TX, Beauveria brongniartii (alternate name) (54) + TX, Chrysoperla carnea (Japanese lacewing) (alternate name) (151) + TX, Cryptolaemus montrouzieri (red ladybird) (alternate name) (178) + TX, Cydia pomonella GV (alternate name) (191) + TX, Dacnusa sibirica (leaf-striped cone wasp) (alternate name) (212) + TX, Diglyphus isaea (alternate name) (254) + TX, Encarsia formosa (scientific name) (293) + TX, Eretmocerus eremicus (alternate name) (300) + TX, Helicoverpa zea NPV (alternate name) (431) + TX, Heterorhabditis bacteriophora and H. megidis (alternate name) (433) + TX, Hippodamia convergens (alternate name) (442) + TX, Leptomastix dactylopii (alternate name) (488) + TX, Macrolophus caliginosus (alternate name) (491) + TX, Mamestra brassicae NPV (alternate name) (494) + TX, Metaphycus helvolus (alternate name) (522) + TX, Metarhizium anisopliae var. acridum (scientific name) (523) + TX, Metarhizium anisopliae var. anisopliae (scientific name) (523) + TX, Neodiprion sertifer NPV and N. lecontei NPV (alternate name) (575) + TX, Orius spp.) (Alternate name) (596) + TX, Paecilomyces fumosoroseus (Alternate name) (613) + TX, Phytoseiulus persimilis (Alternate name) (644) + TX, Spodoptera exigua multicapsid nucleopolyhedrovirus (Scientific name) (741) + TX, Steinernema bibionis (Alternate name) (742) + TX, Steinernema carpocapsae (Alternate name) (742) + TX, Steinernema feltiae (Alternate name) (742) + TX, Steinernema A biological agent selected from the group consisting of Steinernema glaseri (alternate name) (742) + TX, Steinernema riobrave (alternate name) (742) + TX, Steinernema riobravis (alternate name) (742) + TX, Steinernema scapterisci (alternate name) (742) + TX, Steinernema spp. (alternate name) (742) + TX, Trichogramma spp. (alternate name) (826) + TX, Typhlodromus occidentalis (alternate name) (844), and Verticillium lecanii (alternate name) (848) + TX. a soil sterilizing agent selected from the group consisting of iodomethane (IUPAC name) (542) and methyl bromide (537) + TX; an antisterilant selected from the group of substances consisting of apholate [CCN] + TX, Visadyl (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzuron (250) + TX, dimatif (alternative name) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methiotepa [CCN] + TX, methyl apholate [CCN] + TX, morzide [CCN] + TX, penfluron (alternative name) [CCN] + TX, tepa [CCN] + TX, thiohempa (alternative name) [CCN] + TX, thiotepa (alternative name) [CCN] + TX, tretamim (alternative name) [CCN] and uredepa (alternative name) [CCN] + TX, (E)-Deca-5-en-1-ol (IUPAC name) (222) + TX with (E)-deca-5-en-1-yl acetate, (E)-tridec-4-en-1-yl acetate (IUPAC name) (829) + TX, (E)-6-methylhept-2-en-4-ol (IUPAC name) (541) + TX, (E,Z)-tetradec-4, 10-dien-1-yl acetate (IUPAC name) (779) + TX, (Z)-dodec-7-en-1-yl acetate (IUPAC name) (285) + TX, (Z)-hexadec-11-enal (IUPAC name) (436) + TX, (Z)-hexadec-11-en-1-yl acetate (IUPAC name) (437) + TX, (Z)-hexadec-11-en-1-yl acetate (IUPAC name) (438) + TX, Sadec-13-en-11-yn-1-yl acetate (IUPAC name) (438) + TX, (Z)-icos-13-en-10-one (IUPAC name) (448) + TX, (Z)-tetradec-7-en-1-al (IUPAC name) (782) + TX, (Z)-tetradec-9-en-1-ol (IUPAC name) (783) + TX, ( Z)-Tetradeca-9-en-1-yl acetate (IUPAC name) (784) + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate (IUPAC name) (283) + TX, (9Z,11E)-tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780) + TX, (9Z,12E)-tetradeca-9,12-Dien-1-yl acetate (IUPAC name) (781) + TX, 14-methyloctadec-1-ene (IUPAC name) (545) + TX, 4-methylnonan-5-one with 4-methylnonan-5-ol (IUPAC name) (544) + TX, α-multistriatin (alternative name) [CCN] + TX, Brevicomin (alternative name) [CCN] + TX, Codrelle (alternative name) [CCN] + TX, Codrelle (alternative name) (167) + TX, Querle (alternative name) (179) + TX, Dis Parva (277) + TX, dodec-8-en-1-yl acetate (IUPAC name) (286) + TX, dodec-9-en-1-yl acetate (IUPAC name) (287) + TX, dodec-8 + TX, 10-dien-1-yl acetate (IUPAC name) (284) + TX, dominicalua (alternative name) [CCN] + TX, ethyl 4-methyloctanoate (IUPAC name) (317) + TX, eugenol (alternative name) [CCN] + TX, frontalin (alternative name) [CCN] + TX , Gossyplure® (alternative name; 1:1 mixture of the (Z,E) and (Z,Z) isomers of hexadeca-7,11-dien-1-yl-acetate) (420) + TX, Grandolure (421) + TX, Grandolure I (alternative name) (421) + TX, Grandolure II (alternative name) (421) + TX, Grandolure III (alternative name) (421) + TX, Grandolure IV (alternative name) (421) + TX, Hexalure [CCN] + TX, Ipsdienol (alternative name) [CCN] + TX, Ipsenol (alternative name) [CCN] + TX, Japonirua (alternative name) (481) + TX, Lineatin (alternative name) [CCN] + TX, Litirua (alternative name) [CCN] + TX, Lupulua (alternative name) [CCN] + TX, Medurua [CCN] + TX, Megatomoic acid (alternative name) [CCN] + TX, Methyleugenol (alternative name) (540) + TX, Muscalua (563) + TX, Octadeca-2,13-dien-1-yl acetate (IUPAC name) (588) + TX, Octadeca-3,an insect pheromone selected from the group consisting of 13-dien-1-yl acetate (IUPAC name) (589) + TX, orfuralua (alternative name) [CCN] + TX, orictalua (alternative name) (317) + TX, ostramon (alternative name) [CCN] + TX, siglua [CCN] + TX, sordidin (alternative name) (736) + TX, sulcatol (alternative name) [CCN] + TX, tetradec-11-en-1-yl acetate (IUPAC name) (785) + TX, trimedlure (839) + TX, trimedlure A (alternative name) (839) + TX, trimedlure B1 (alternative name) (839) + TX, trimedlure B2 (alternative name) (839) + TX, trimedlure C (alternative name) (839) and trunk call (alternative name) [CCN] + TX; an insect repellent selected from the group of substances consisting of 2-(octylthio)-ethanol (IUPAC name) (591) + TX, butopyronoxyl (933) + TX, butoxy(polypropylene glycol) (936) + TX, dibutyl adipate (IUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (IUPAC name) (1048) + TX, diethyltoluamide [CCN] + TX, dimethylcarbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1137) + TX, hexamide [CCN] + TX, methoquinbutyl (1276) + TX, methyl neodecanoamide [CCN] + TX, oxamate [CCN], and picaridin [CCN] + TX; Bis(tributyltin)oxide (IUPAC name) (913) + TX, Bromoacetamide [CCN] + TX, Calcium arsenate [CCN] + TX, Cloetocarb (999) + TX, Copper acetarsenite [CCN] + TX, Copper sulfate (172) + TX, Fentin (347) + TX, Ferric phosphate (IUPAC name) (352) + TX, Metaldehyde (518) + TX, Methiocarb (530) + TX, Nicolasamide (576) + TX, Nicolasamide olamine (576) + TX, Pentachloroform a molluscicide selected from the group consisting of phenol (623) + TX, pentachlorophenoxide sodium salt (623) + TX, thionazine (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913) + TX, triphenmorph (1454) + TX, trimethacarb (840) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX, pyriprole [394730-71-3] + TX, AKD-3088 (compound code) + TX, 1,2-dibromo-3-chloropropane (IUPAC / Chemical Abstracts name) (1045) + TX, 1,2-dichloropropane (IUPAC / Chemical Abstracts name) (1062) + TX, 1,3-dichloropropene with 1,2-dichloropropane (IUPAC name) (1063) + TX, 1,3-dichloropropene (233) + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide (IUPAC / Chemical Abstracts name) (106 ... Abstracts name) (1065) + TX, 3-(4-chlorophenyl)-5-methylrhodanine (IUPAC name) (980) + TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPAC name) (1286) + TX, 6-isopentenylaminopurine (alternative name) (210) + TX, abamectin (1) + TX, acetoprole [CCN] + TX, alanycarb (15) + TX, aldicarb (16) + TX, aldoxicarb (863) + TX, AZ60541 (compound code) + TX, benclotiaz [CCN] + TX, benomyl (62) + TX, butylpyridaben (alternative name) + TX, cadusafos (109) + TX, carbofuran (118) + TX, carbon disulfide (945) + TX, carbosulfan (119) + TX, chloropicrin (141) + TX, chlorpyrifos (145) + TX, cloetocarb ( 999) + TX, cyclobutrifluram + TX, cytokinin (alternative name) (210) + TX, dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamidaphos (1044) + TX, dichlorophenthion (1051) + TX, dicrifos (alternative name) + TX, dimethoate (262) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin Benzoate (291) + TX, Epirinomectin (alternative name) [CCN] + TX, Ethoprophos (312) + TX, Ethylenedibromide (316) + TX, Fenamiphos (326) + TX, Fenpyrad (alternative name) + TX, Fensulfothion (1158) + TX, Fosthiazate (408) + TX, Fostietan (1196) + TX, Lufural (alternative name) [CCN] + TX, GY-81 (development code) (423) + TX,Heterofos [CCN] + TX, Iodomethane (IUPAC name) (542) + TX, Isamidophos (1230) + TX, Isazophos (1231) + TX, Ivermectin (alternative name) [CCN] + TX, Kinetin (alternative name) (210) + TX, Mecarfone (1258) + TX, Metam (519) + TX, Metam potassium (alternative name) (519) + TX, Metam sodium (519) + TX, Methyl bromide (537) + TX, Methyl isothiocyanate (543) + TX, Milbemycin oxime (alternative name) [CCN] + TX, Moxidectin (alternative name [CCN] + TX, Myrothecium verrucaria verrucaria) Composition (alternative name) (565) + TX, NC-184 (compound code) + TX, Oxamyl (602) + TX, Phorate (636) + TX, Phosphamidon (639) + TX, Phosphocarb [CCN] + TX, Cebufos (alternative name) + TX, Selamectin (alternative name) [CCN] + TX, Spinosad (737) + TX, Terbam (alternative name) + TX, Terbufos (773) + TX, Tetrachlorothiophene (IUPAC / Chemical A nematicide selected from the group of substances consisting of (Abstracts name) (1422) + TX, thiafenox (alternative name) + TX, thionazine (1434) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, xylenols [CCN] + TX, YI-5302 (compound code) and zeatin (alternative name) (210) + TX, fluensulfone [318290-98-1] + TX, and fluopyram + TX, a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580) + TX; a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720) + TX; 2-Isovalerylindan-1,3-dione (IUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, α-chlorohydrin [CCN] + TX, aluminum phosphide (640) + TX, anthraquinone (880) + TX, arsenic trioxide (882) + TX, barium carbonate (891) + TX, bisthiosemicarbamate (912) + TX, brodifacoum (89) + TX, bromadiolone (including α-bromadiolone) + TX, brometholone Phosphorus (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorophacinone (140) + TX, cholecalciferol (alternative name) (850) + TX, coumachlor (1004) + TX, coumafuryl (1005) + TX, coumatetralyl (175) + TX, crimidine (1009) + TX, difenacoum (246) + TX, difethialone (249) + TX, diphacinone (273) + TX, ergocalciferol (301) + TX, flocoumafen (35 7) + TX, fluoroacetamide (379) + TX, flupropazine (1183) + TX, flupropazine hydrochloride (1183) + TX, γ-HCH (430) + TX, HCH (430) + TX, hydrogen cyanide (444) + TX, iodomethane (IUPAC name) (542) + TX, lindane (430) + TX, magnesium phosphide (IUPAC name) (640) + TX, methyl bromide (537) + TX, norbormide (1318) + TX, phosacetim (1336) + TX, phosphine ( a rodenticide selected from the group consisting of (IUPAC name) (640) + TX, phosphorus [CCN] + TX, pindone (1341) + TX, potassium arsenite [CCN] + TX, pyrinuron (1371) + TX, sciliroside (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoroacetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCN] + TX, warfarin (851), and zinc phosphide (640) + TX; a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)-ethyl piperonylate (IUPAC name) (934) + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903) + TX, nerolidol with farnesol (alternative name) (324) + TX, MB-599 (development code) (498) + TX, MGK264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piperotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmolin (1394) and sulfoxide (1406) + TX; an animal repellent selected from the group of substances consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine acetate (422) + TX, methiocarb (530) + TX, pyridin-4-amine (IUPAC name) (23) + TX, thiram (804) + TX, trimethacarb (840) + TX, zinc naphthenate [CCN], and ziram (856) + TX; an antiviral agent selected from the group of substances consisting of Imanin (alternative name) [CCN] and Ribavirin (alternative name) [CCN] + TX; a wound protectant selected from the group of substances consisting of mercury(II) oxide (512) + TX, octilinone (590) and thiophanate methyl (802) + TX; 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 2,4-dichlorophenylbenzenesulfonate + TX, 2-fluoro-N-methyl-N-1-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, benzoic acid Benzyl + TX, Bixafen + TX, Brofenvalerate + TX, Bromocyclen + TX, Bromophos + TX, Bromopropylate + TX, Buprofezin + TX, Butocarboxim + TX, Butoxycarboxim + TX, Butylpyridaben + TX, Calcium polysulfide + TX, Camphechlor + TX, Carbanolate + TX, Carbophenothion + TX, Cimiazole + TX, Chinomethionate + TX, Chlorbeside + TX, Chlordimeform + TX, Chlordimeform Hydrochloride + TX, Chlorphenetole + TX, Chlorfenson + TX, Chlor Lofensulfide +TX, Chlorobenzilate +TX, Chlormebform +TX, Chlormethiuron +TX, Chloropropylate +TX, Chlorthiophos +TX, Cinerin I +TX, Cinerin II +TX, Cinerins +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, De Demeton-S+TX, Demeton-S-methyl+TX, Demeton-S-methylsulfone+TX, Dichlofluanid+TX, Dichlorvos+TX, Dicrifos+TX, Dienochlor+TX, Dimefox+TX, Zinex+TX, Zinex-Diclexin+TX, Dinocap-4+TX, Dinocap-6+TX, Dinocton+TX, Dinopenton+TX, Dinosulfone+TX, Dinotervone+TX, Dioxathion+TX, Diphenylsulfone+TX, Disulfiram+TX, DNOC+TX, Dofenapine+TX, Doramectin+TX, Endothion+TX,Eprinomectin +TX, Ethoate Methyl +TX, Etrimphos +TX, Fenazaflor +TX, Fenbutatin Oxide +TX, Fenothiocarb +TX, Fenpyrad +TX, Fenpyroximate +TX, Fenpyrazamine +TX, Fenson +TX, Fentrifanil +TX, Flubenzimine +TX, Flucycloxuron +TX, Fluenethyl +TX, Fluorobenside +TX, FMC1137 +TX, Formetanate +TX, Formetanate Hydrochloride +TX, Formoparanate +TX, γ-HCH +TX, Gliodin +TX, Halfenp Rox + TX, Hexadecylcyclopropanecarboxylate + TX, Isocarbophos + TX, Jasmolin I + TX, Jasmolin II + TX, Jodofenphos + 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 (6-Iodo-3-pyridyl)methoxy)pyridazin-3-one + TX, Nifluridizide + TX, Nikkomycin + TX, Nitrilacarb + TX, Nitrilacarb 1:1 zinc chloride complex + TX, Omethoate + TX, Oxydeprophos + TX, Oxydisulfoton + TX, pp'-DDT + TX, Parathion + TX, Permethrin + TX, Fenkapton + TX, Phosalone + TX, Phosphorane + TX, Phosphamidon + TX, Polychloroterpenes + TX, Polynactin + TX, Proclonol + TX, Promacil + TX, Propox Lu+TX, Protidathion+TX, Protoate+TX, Pyrethrin I+TX, Pyrethrin II+TX, Pyrethrin+TX, Pyridaphenthion+TX, Pirimitate+TX, Quinalphos+TX, Quinthiofos+TX, R-1492+TX, Phosglycine+TX, Rotenone+TX, Schladan+TX, Cebufos+TX, Selamectin+TX, Sofamid+TX, SSI-121+TX, Sulfiram+TX, Sulfuramide+TX, Sulfotep+TX, Sulfur+TX, Diflobidazin+TX, τ-Fulvalinate+TX, TEPP+TX, Thelbam+TX,Tetradifon +TX, Tetrasulf +TX, Thiafenox +TX, Thiocarboxim +TX, Thiofanox +TX, Thiometon +TX, Thioquinox +TX, Thuringiensin +TX, Triamiphos +TX, Triatene +TX, Triazophos +TX, Triazuron +TX, Trifenophos +TX, Trinactin +TX, Vamidothion +TX, Vaniliprole +TX, Bethoxazin +TX, Copper dioctanoate +TX, Copper sulfate +TX, Sibutrin +TX, Dichlorn +TX, Dichlorophen +TX, Endothal +TX, Fentin +TX, Slaked lime +TX, Nabam +TX, Quinoclamine +TX, Quinoneamide +TX, Simazine +TX, Triphenyltin acetate +TX, Triphenyltin hydroxide +TX, Crufomate +TX, Piperazine +TX, Thiophanate +TX, Chloralose +TX, Fenthion +TX, Pyridin-4-amine + TX, strychnine + TX, 1-hydroxy-1H-pyridine-2-thione + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide + TX, 8-hydroxyquinoline sulfate + TX, bronopol + TX, copper hydroxide + TX, cresol + TX, dipyrithione + TX, doditin + TX, fenaminosulf + TX, formaldehyde + 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, Adoxophyes orana GV+TX, Agrobacterium radiobacter+TX, Amblyseius spp.+TX, Anagrapha falcifera NPV+TX, Anagrahus atomus+TX, Aphelinus abdominalis+TX, Aphidius colemani+TX,Aphidoletes aphidimyza + TX, Autographa californica NPV + TX, Bacillus sphaericus Neide + TX, Beauveria brongniartii + TX, Chrysoperla carnea + TX, Cryptolaemus montrouzieri + TX, Codling moth (Cydia pomonella GV) + TX, Dacnusa sibirica + TX, Diglyphus isaea + TX, Encarsia formosa + TX, Eretmocerus eremicus + TX, Heterorhabditis bacteriophora and H. megidis + TX, Hippodamia convergens + TX, Leptomastix dactylopii + TX, Macrolophus caliginosus + TX, Mamestra brassicae NPV + TX, Metaphycus helvolus + TX, Metarhizium anisopliae var. acridum + TX, Metarhizium anisopliae var. anisopliae + TX, Neodiprion sertifer NPV and N. lecontei NPV + TX, Orius spp. + TX, Paecilomyces fumosoroseus + TX, Phytoseiulus persimilis + TX, Steinernema bibionis + TX,Steinernema carpocapsae + TX, Steinernema feltiae + TX, Steinernema glaseri + TX, Steinernema riobrave + TX, Steinernema riobravis + TX, Steinernema scapterisci + TX, Steinernema spp. + TX, Trichogramma spp. + TX, Typhlodromus occidentalis + TX, Verticillium lecanii) + TX, Aphorate + TX, Visadil + TX, Busulfan + TX, Dimatif + TX, Hemel + TX, Hempa + TX, Metepa + TX, Methiotepa + TX, Methyl Aphorate + 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)-icos-13-en-10-one + TX, (Z)-tetradec-7-en-1-al + TX, (Z)-tetradec-9-en-1-ol + TX, (Z)-tetradec-9-en-1-yl acetate + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate + TX, (9Z,11E)-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, α-multistriatin + TX, Brevicomin + TX, Codrelle + TX, Codlemone + TX, Querle + TX, Disparlua + TX, Dodec-8-en-1-yl acetate + TX, Dodec-9-en-1-yl acetate + TX, Dodec-8 + TX, 10-dien-1-yl acetate +TX, Dominicalure +TX, Ethyl 4-methyloctanoate +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, Looplure +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, Olfural + TX, Orictal + TX, Ostramon + TX, Cigla + TX, Soldigin + TX, Sulcatol + TX, Tetradec-11-en-1-yl acetate + TX, Trimedulla + TX, Trimedulla A + TX, Trimedulla B1 + TX, Trimedulla B2 + TX, Trimedulla C + TX, Trunk-Cole + TX, 2-(octylthio)ethanol + TX, Butopyronoxyl + TX, Butoxy(polypropylene glycol) + TX, Dibutyl adipate + TX, Djibutin methyl phthalate + TX, dibutyl succinate + TX, diethyl toluamide + TX, dimethylcarbate + TX, dimethyl phthalate + TX, ethyl hexanediol + TX, hexamide + TX, methoquin-butyl + TX, methyl neodecanoamide + 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 methyl phosphate + TX, 2-(1,3-dithiolan-2-yl)phenyl dimethyl carbamate + TX, 2-(2-butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methyl carbamate + TX, 2-(4-chloro-3,5-xylyloxy)ethanol + TX, 2-chlorovinyl diethyl phosphate + TX, 2-imidazolidone + TX, 2-isovalerylindane -1,3-dione + TX, 2-methyl(prop-2-ynyl)aminophenyl methyl carbamate + TX, 2-thiocyanatoethyl laurate + TX, 3-bromo-1-chloroprop-1-ene + TX, 3-methyl-1-phenylpyrazol-5-yl dimethyl carbamate + TX, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methyl carbamate + TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethyl carbamate + TX, acetone + TX, acrylonitrile + TX, aldrin + TX, allosamidin + TX,Alixicarb + TX, α-ecdysone + TX, aluminum phosphide + TX, aminocarb + TX, anabasine + TX, atidathion + TX, azamethiphos + TX, Bacillus thuringiensis δ-endotoxin + TX, barium hexafluorosilicate + TX, barium polysulfide + TX, bartholin + TX, Bayer 22 / 190 + TX, Bayer 22408 + TX, β-cyfluthrin + TX, β-cypermethrin + TX, bioethanomethrin + TX, biopermethrin + TX, bis(2-chloroethyl) ether + TX, borax + TX, bromfenvinphos + TX, bromo-DDT + TX, bufencarb + TX, butacarb + TX, butathiol Phos + TX, Butonate + TX, Calcium arsenate + TX, Calcium cyanide + TX, Carbon disulfide + TX, Carbon tetrachloride + TX, Cartap hydrochloride + TX, Cevadin + 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, Columbine + TX, Ice Crystallite + TX, CS708 + TX, Cyanofenphos + TX, Cyanophos + TX, Cyclethrin + TX, Sithioate + TX, d-Tetramethrin + TX, DAEP + TX, Dazomet + TX, Decarbofuran + TX, Diamidaphos + TX, Dikapton + TX, Dichlorophenthion + TX, Dicresyl + TX, Dicyclanil + TX, Dieldrin + TX, Diethyl 5-methylpyrazol-3-yl phosphate + TX, Dilol + TX, Dimefluthrin + TX, Dimethane + TX, Dimethrine + 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, etaphos + 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, Hikin Carb + TX, IPSP + 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, Lead Arsenate + TX, Leptophos + TX, Lilimphos + TX, Ritidathion + TX, m-Cumenylmethylcarbamate + TX, Magnesium Phosphide + TX, Magidox + TX, Mecarfone + TX, Menasone + TX, Monocalcium Chloride Silver + TX, mesulfenphos + TX, metam + TX, metam-potassium + TX, metam-sodium + TX, methanesulfonyl fluoride + TX, methocrotophos + TX, methoprene + TX, methotrin + TX, methoxychlor + TX, methyl isothiocyanate + TX, methyl chloroform + TX, methylene chloride + TX, methoxadiazone + TX, Mirex + TX, naphthalophos + TX, naphthalene + TX, NC-170 + TX, nicotine + TX, nicotine sulfate + TX, nithiazine + TX, nornicotine + TX, O-5-Dichloro-4-iodophenyl O-ethyl ethyl phosphonothioate + 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, PH 60-38 + TX, Fenkapton + TX, Fosnichlor + 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, Pyrimidophos + TX, Profluthrin + TX, Promecarb + TX, Prothiofos + TX, Pyrazophos + TX, Pyresmethrin + TX, Cassia + TX, Quinalphos-methyl + TX, Quinothione + TX, Lafoxanide + TX, Resmethrin + TX, Rotenone + TX, Kadethrin + TX, Riania + TX, Ryanodine + TX, Sabadila + TX, Shradan + TX, Cebufos + TX, SI-0009 + TX, Tiapronil + TX, Sodium Arsenite + TX, Sodium Cyanide + TX, Sodium Fluoride + TX, Sodium Hexafluorosilicate + TX, Sodium Pentachlorophenoxide + TX, Sodium Selenate + TX, Sodium Thiocyanate +TX, 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 oxalate +TX, Thionazine +TX, Thiosultap +TX, Thiosultap-sodium +TX, Tralomethrin +TX, Transpermethrin +TX, Triazamate +TX, Trichlormetaphos-3 +TX, Trichloronat +TX, Trimethacarb +TX, Tolprocarb +TX, Triclopiricarb +TX, Triplene +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-isopentenylaminopurine + TX, anicifluprine + TX, benclotiaz + TX, cytokinin + TX, DCIP + TX, furfural + TX, isamidophos + TX, kinetin + TX, Myrothecium verrucaria verrucaria) composition +TX, tetrachlorothiophene +TX, xylenol +TX, zeatin +TX, potassium ethylxanthate +TX, acibenzolar +TX, acibenzolar-S-methyl +TX, giant knotweed (Reynoutria sachalinensis) extract +TX, α-chlorohydrin +TX, anth +TX, barium carbonate +TX, bisthiosemi +TX, prodifacoum +TX, bromadiolone +TX, bromethalin +TX, chlorophacinone +TX, cholecalciferol +TX, coumachlor +TX, coumafuryl +TX, coumatetralyl +TX, crimidine +TX, difenacoum +TX, difethialone +TX, diphacinone +TX, ergocalciferol +TX, flocoumafen +TX, fluoroa Cetamide + TX, flupropazine + TX, flupropazine hydrochloride + TX, norbormide + TX, fosacetim + TX, phosphorus + TX, pindone + TX, pyrinuron + TX, sciliroside + TX, sodium fluoroacetate + TX, thallium sulfate + TX, warfarin + TX, 2-(2-butoxyethoxy)ethyl piperonylate + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone + TX, farnesol and nerolidol + TX, verbutin + TX, MGK 264 + TX, piperonyl butoxide + TX, piprotal + TX, propyl isomer + TX, S421 + TX, sesamex + TX, sesasmolin + TX, sulfoxide + TX, anthraquinone + TX, copper naphthenate + TX,Copper oxychloride + TX, dicyclopentadiene + TX, thiram + TX, zinc naphthenate + TX, ziram + TX, imanin + TX, ribavirin + TX, chlorinconazid + TX, mercury(II) 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, hexafluorophosphate Saconazole + TX, Imazalil + TX, Imibenconazole + TX, Ipconazole + TX, Metconazole + TX, Myclobutanil + TX, Paclobutrazol + TX, Pefurazoate + TX, Penconazole + TX, Prothioconazole + TX, Pyrifenox + TX, Prochloraz + TX, Propiconazole + TX, Pyrosoxazole + 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, Ofrace + TX, Oxadixyl + TX, Carbendazim + TX, Debacarb + TX, Fuberidazole ru+TX, thiabendazole+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, iminoctadine+TX, azoxystrobin+TX, dimoxystrobin+TX, enestrobulin+TX, phenaminestrobin+TX, flufenoxystrobin+TX, fluoxastrobin+TX,Kresoxim-methyl + TX, metominostrobin + TX, trifloxystrobin + TX, oryzastrobin + TX, picoxystrobin + TX, pyraclostrobin + TX, pyrametostrobin + TX, pyroxystrobin + TX, ferbam + TX, mancozeb + TX, maneb + ​​TX, metiram + TX, propineb + ​​TX, zineb + ​​TX, captafol + TX, captan + TX, fluoroimide + TX, folpet + TX, tolylfluanid + TX, Bordeaux mixture + TX, copper oxide + TX, mancopper + TX, Oxine-copper +TX, Nitrothal-isopropyl +TX, Edifenphos +TX, Iprobenfos +TX, Fosdifen +TX, Turcofos-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 +T X, ethaboxam + TX, etridiazole + TX, famoxadone + TX, fenamidone + TX, fenoxanil + TX, ferimzone + TX, fluazinam + TX, flumethylsulfolim + TX, fluopicolide + TX, fluoxythioconazole + TX, flusulfamide + TX, fluxapyroxad + TX, fenhexamid + TX, fosetyl-aluminum + TX, hymexazole + TX, iprovalicarb + TX, cyazofamid + TX, methasulfocarb + TX, metrafenone + TX, pencycuron + TX X, 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, flubeneteram + TX, isopyrazam + TX, sedaxane + TX, benzovindiflupir + TX, pydiflumetofen + TX,3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide + TX, isoflucipram + TX, isotianil + TX, dipimethitrone + TX, 6-ethyl-5,7-dioxo-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 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-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, rububenmixianan + 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, inpirfluxam + TX, tolprocarb + 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-ethyl-N-methyl-formamidine + TX, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonate + TX, but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazole-5- methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate + TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX, 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-trimethylpyrazol-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, florylpicoxamide + TX, fenpicoxamide + TX, methallylpicoxamide + TX, tebufloquine + TX, ipulfenoquine + TX, quinofumelin + TX, isofetamide + TX, ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate + TX (which can be prepared by 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 + TX (which can be prepared by 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 + TX (which can be prepared by the method described in WO 2020 / 097012), methyl N-[[4-[1-(2,6-difluoro-4-isopropyl- phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate + TX (which can be prepared by the methods 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 + TX (which can be prepared by the methods described in WO 2020 / 109391), 6-chloro-N-[2-(2-chloro-4-methyl-phenyl)-2, 2-difluoro-ethyl]-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide + TX (which can be prepared by the methods 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 + TX (which can be prepared by the methods described in WO 2020 / 109391), 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, Fenamacril + TX, 5-Amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, Fluopyram + TX, Flufenoxadiazam + TX, Flutianil + TX, Fluopimomide + TX, Pirapropoin + TX, Picarbtrazox + TX, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethylethyl)pyrazole-4-carboxamide + TX, methyl-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, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidinemethanol + TX, fluoxapiprolin + TX, enoxastrobin + TX, methyl (Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazole-2-yl]phenoxy]prop-2-enoate + TX, methyl (Z)-3-methoxy-2-[2-methyl-5-(4-propyltriazole-2-yl)phenoxy]prop-2-enoate + TX, methyl (Z)-2-[5-(3-

[0033] methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoate + TX, methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoate + TX, methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoate + TX (these compounds are disclosed in WO 2020 / 0791 No. 11), methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate + TX, methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate + TX (these compounds can be prepared by the methods described in WO 2020 / 193387), 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxyphenyl]-4-methyl- ... -3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, trinexapac + TX, cumoxystrobin + TX, zhongshengmycin + TX, copper thiodiazole + TX, zinc thiazole + TX, amethotractin + TX, iprodione + TX, seboxylamine + TX; N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy]benzonitrile + TX, trinexapac + TX, cumoxystrobin + TX, zhongshengmycin + TX, copper thiodiazole + TX, zinc thiazole + TX, amethotractin + TX, iprodione + TX, seboxylamine + 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-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-chloro N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine + TX (these compounds can be prepared by the method described in WO 2015 / 155075); N'-[5-bromo-2-methyl- 6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX (this compound can be prepared 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,N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine + TX (these compounds can be prepared by the method described in WO 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine + TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl 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-3,3,3-trifluoro-1-methyl-propyl]-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-3-carboxamide + TX, 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 by 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 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-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 by 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-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-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX ,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]isoxazolidin-3-one + TX N,N-dimethyl-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 by 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 by 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 by 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 by 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 by the method described in WO 2016 / 156290); (4-phenoxyphen N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzene (N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzene) with TX (this compound can be prepared by the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone with TX (this compound can be prepared by the method described in WO 2011 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzene Carbothioamide + 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 by 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 by 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 by the method described in WO 2014 / 095675); (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl (3-methylisoxazol-5-yl)-[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 (these compounds can be prepared by 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 by the method described in WO 2018 / 065 414); ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate + TX (this compound can be prepared by 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]phenyl]acetamide + TX biologically active substances selected from N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-[N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX (these compounds can be prepared by the methods described in WO 2018 / 202428); Microorganisms including: Acinetobacter lwoffii + TX, Acremonium alternatum + TX, Acremonium cephalosporium + TX, Acremonium diospyri + TX, Acremonium obclavatum + TX, Adoxophyes orana granulovirus (AdoxGV) (Capex®) + TX, Agrobacterium radiobacter strain K84 (Galltrol-A®) + TX, Alternaria alternate + TX, Alternaria cassia + TX, cassia) + TX, Alternaria destruens (Smolder®) + TX, Ampelomyces quisqualis (AQ10®) + TX, Aspergillus flavus AF36 (AF36®) + TX, Aspergillus flavus NRRL21882 (Aflaguard®) + TX, Aspergillus spp.) + TX, Aureobasidium pullulans + TX, Azospirillum + TX, (MicroAZ® + TX, TAZO B®) + TX, Azotobacter + TX, Azotobacter chroocuccum (Azotomeal®) + TX, Azotobacter cyst (Bionatural Blooming Blossoms®) + TX, Bacillus amyloliquefaciens + TX, Bacillus cereus + TX, Bacillus chitinosporus strain CM-1 + TX, Bacillus chitinosporus strain AQ746 + TX, Bacillus licheniformis strain HB-2 (Biostart™ Rhizoboost®) + TX, Bacillus licheniformis strain 3086 (EcoGuard® + TX, Green Releaf®) + TX, Bacillus circulans + TX, Bacillus firmus (BioSafe® + TX, BioNem-WP® + TX, VOTiVO® + TX), Bacillus firmus strain I-1582 + TX, Bacillus macerans + TX, Bacillus marismortui + TX, Bacillus megaterium megaterium) + TX, Bacillus mycoides strain AQ726 + TX, Bacillus papillae (Milky Spore Powder®) + TX, Bacillus pumilus spp.) + TX, Bacillus pumilus strain GB34 (Yield Shield®) + TX, Bacillus pumilus strain AQ717 + TX, Bacillus pumilus strain QST2808 (Sonata® + TX, Ballad Plus®) + TX, Bacillus spahericus (VectoLex®) + TX, Bacillus spp. + TX, Bacillus spp. strain AQ175 + TX, Bacillus spp. strain AQ177 + TX, Bacillus spp. strain AQ178 + TX, Bacillus subtilis Bacillus subtilis strain QST713 (CEASE®+TX, Serenade®+TX, Rhapsody®)+TX, Bacillus subtilis strain QST 714 (JAZZ®)+TX, Bacillus subtilis strain AQ153+TX, Bacillus subtilis strain AQ743+TX, Bacillus subtilis strain QST3002+TX, Bacillus subtilis strain QST3004+TX, Bacillus subtilis var. amyloliquefaciensamyloliquefaciens strain FZB24 (Taegro® + TX, Rhizopro®) + TX, Bacillus thuringiensis Cry 2Ae + TX, Bacillus thuringiensis Cry 1Ab + TX, Bacillus thuringiensis aizawai GC91 (Agree®) + TX, Bacillus thuringiensis israelensis (BMP123® + TX, Aquabac® + TX, VectoBac®) + TX, Bacillus thuringiensis kurstaki Bacillus thuringiensis kurstaki (Javelin® +TX, Deliver® +TX, CryMax® +TX, Bondide® +TX, Scutella WP® +TX, Turilav WP® +TX, Astuto® +TX, Dipel WP® +TX, Biobit® +TX, Foray®) +TX, Bacillus thuringiensis kurstaki BMP123 (Baritone®) +TX, Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF / 3P®) +TX, Bacillus thuringiensis strain BD#32 + TX, Bacillus thuringiensis strain AQ52 + TX, Bacillus thuringiensis var. aizawai (XenTari® + TX, DiPel®) + TX, bacterial spp. (GROWMEND® + TX, GROWSWEET® + TX, Shootup®) + TX, Clavipacter michiganensis bacteriophage (AgriPhage®) + TX, Bakflor® + TX, Beauveria bassiana (Beaugenic® + TX, Brocaril WP®) + TX, Beauveria bassiana GHA (Mycotrol ES® + TX, Mycotrol O® + TX, BotaniGuard®) + TX, Beauveria brongniartii (Engerlingspilz® + TX, Schweizer Beauveria® + TX, Melocont®) + TX, Beauveria spp.) + TX, Botrytis cineria + TX, Bradyrhizobium japonicum (TerraMax®) + TX, Brevibacillus brevis + TX, Bacillus thuringiensis tenebrionis (Novodor®) + TX, BtBooster + TX, Burkholderia cepacia (Deny® + TX, Intercept® + TX, Blue Circle®) + TX, Burkholderia gladii + TX, Burkholderia gladioli + TX, Burkholderia spp. + TX, Canadian thistle fungus (CBH Canadian Bioherbicide®) + TX, Candida butyri + TX, Candida famata + TX, Candida fructus + TX, Candida glabrata + TX, Candida guilliermondii + TX, Candida melibiosica + TX, Candida oleophila strain O + TX, Candida parapsilosis + TX, Candida pelliculosa + TX, Candida pulcherrima + TX, Candida reukaufii + TX, Candida cytoana saitoana) (Bio-Coat® + TX, Biocure®) + TX, Candida sake + TX, Candida spp.) + TX, Candida tenius + TX, Cedecea dravisae + TX, Cellulomonas flavigena + TX, Chaetomium cochliodes (Nova-Cide®) + TX, Chaetomium globosum (Nova-Cide®) + TX, Chromobacterium subtsugae strain PRAA4-1T (Grandevo®) + TX, Cladosporium cladosporioides + TX, Cladosporium oxysporum + TX, Cladosporium chlorocephalum chlorocephalum + TX, Cladosporium spp. + TX, Cladosporium tenuissimum + TX, Clonostachys rosea (EndoFine®) + TX, Colletotrichum acutatum + TX, Coniothyrium minitans (Cotans WG®) + TX, Coniothyrium spp.) + TX, Cryptococcus albidus (YIELDPLUS®) + TX, Cryptococcus humicola + TX, Cryptococcus infirmo-miniatus + TX, Cryptococcus laurentii + TX, Cryptophlebia leucotreta granulovirus (Cryptex®) + TX, Cupriavidus campinensis + TX, Codling moth granulovirus (Cydia pomonella granulovirus) (CYD-X®) + TX, Codling moth granulovirus (Cydia pomonella granulovirus) (Madex® + TX, Madex Plus® + TX, Madex Max / Carpovirusine®) + TX, Cylindrobasidium laeve (Stumpout®) + TX, Cylindrocladium + TX, Debaryomyces hansenii + TX, Drechslera hawaiinensis + TX, Enterobacter cloacae + TX, Enterobacteriaceae + TX, Entomophtora virulenta (Vektor®) + TX, Epicoccum nigrum + TX, Epicoccum purpuraense purpurascens) + TX, Epicoccum spp.) + TX, Filobasidium floriforme + TX, Fusarium acuminatum + TX, Fusarium chlamydosporum + TX, Fusarium oxysporum (Fusaclean® / Biofox C®) + TX, Fusarium proliferatum + TX, Fusarium spp. + TX, Galactomyces geotrichum + TX, Gliocladium catenulatum (Primastop® + TX, Prestop®) + TX, Gliocladium roseum + TX, Gliocladium spp. (SoilGard®) + TX, Gliocladium virens (Soilgard®) + TX, Granulovirus (Granupom®) + TX, Halobacillus halophilus + TX, Halobacillus litoralis + TX, Halobacillus trueperi + TX, Halomonas spp. + TX, Halomonas subglaciescola + TX. Halovibrio variabilis + TX, Hanseniaspora uvarum + TX, Helicoverpa armigera nucleopolyhedrovirus (Helicovex®) + TX, Helicoverpa zea nuclear polyhedrosis virus (Gemstar®) + TX, isoflavone-formononetin (Myconate®) + TX, Kloeckera apiculata + TX, Kloeckera spp.) + TX, Lagenidium giganteum (Laginex®) + TX, Lecanicillium longisporum (Vertiblast®) + TX, Lecanicillium muscarium (Vertikil®) + TX, Lymantria Dispar nucleopolyhedrosis virus (Disparvirus®) + TX, Marinococcus halophilus + TX, Meira geulakonigii + TX, Metarhizium anisopliae (Met52®) + TX, Metarhizium anisopliae (Destruxin®) + TX, WP®) + TX, Metschnikowia fruticola (Shemer®) + TX, Metschnikowia pulcherrima + TX, Microdochium dimerum (Antibot®) + TX, Micromonospora coerulea + TX, Microsphaeropsis ochracea + TX, Muscodor albus 620 (Muscudor®) + TX, Muscodor roseus strain A3-5 + TX, Mycorrhizae spp.) (AMykor® +TX, Root Maximizer®) +TX, Myrothecium verrucaria strain AARC-0255 (DiTera®) +TX, BROS PLUS® +TX, Ophiostoma piliferum strain D97 (Sylvanex®) +TX, Paecilomyces farinosus +TX, Paecilomyces fumosoroseus (PFR-97® +TX, PreFeRal®) +TX, Paecilomyces linacinus (Biostat WP®) +TX, Paecilomyces lilacinus strain 251 (MeloCon WG®) + TX, Paenibacillus polymyxa + TX, Pantoea agglomerans (BlightBan C9-1®) + TX, Pantoea spp. + TX, Pasteuria spp. (Econem®) + TX, Pasteuria nishizawae + TX, Penicillium aurantiogriseum + TX, Penicillium billai (Jumpstart® + TX, TagTeam®) + TX, Penicillium brevicompactum brevicompactum + TX, Penicillium frequentans + TX, Penicillium griseofulvum + TX, Penicillium purpurogenum + TX, Penicillium spp.) + TX, Penicillium viridicatum + TX, Phlebiopsis gigantean (Rotstop®) + TX, Phosphate Soluble Bacteria (Phosphomeal®) + TX, Phytophthora cryptogea + TX, Phytophthora palmivora (Devine®) + TX, Pichia anomala + TX, Pichia guilermondii + TX, Pichia membranaefaciens + TX, Pichia onychis + TX, Pichia stipites + TX, Pseudomonas aeruginosa aeruginosa + TX, Pseudomonas aureofaciens (Spot-Less Biofungicide®) + TX, Pseudomonas cepacia + TX, Pseudomonas chlororaphis (AtEze®) + TX, Pseudomonas corrugate + TX, Pseudomonas fluorescens strain A506 (BlightBan A506®) + TX, Pseudomonas putida + TX, Pseudomonas reactans + TX, Pseudomonas spp.) + TX, Pseudomonas syringae (Bio-Save®) + TX, Pseudomonas viridiflava + TX, Pseudomonas fluorescens (Zequanox®) + TX, Pseudozyma flocculosa strain PF-A22 UL (Sporodex L®) + TX, Puccinia canaliculata + TX, Puccinia thlaspeos (Wood Warrior®) + TX, Pythium paroecandrum + TX, Pythium oligandrum) (Polygandron® + TX, Polyversum®) + TX, Pythium periplocum + TX, Rhanella aquatilis + TX, Rhanella spp. + TX,. Rhizobia (Dormal® + TX, Vault®) + TX, Rhizoctonia + TX, Rhodococcus globerulus strain AQ719 + TX, Rhodosporidium diobovatum + TX, Rhodosporidium toruloides + TX, Rhodotorula spp. + TX, Rhodotorula glutinis + TX, Rhodotorula graminis + TX, Rhodotorula mucilagnosa + TX, Rhodotorula rubra + TX, Saccharomyces cerevisiae cerevisiae + TX, Salinococcus roseus + TX, Sclerotinia minor + TX, Sclerotinia minor (SARRITOR®) + TX, Scytalidium spp. + TX, Scytalidium uredinicola + TX, Spodoptera exigua nuclear polyhedrosis virus (Spod-X® + TX, Spexit®) + TX, Serratia marcescens + TX, Serratia plymuthica + TX, Serratia spp.) + TX, Sordaria fimicola + TX, Spodoptera littoralis nucleopolyhedrovirus (Littovir®) + TX, Sporobolomyces roseus + TX, Stenotrophomonas maltophilia + TX, Streptomyces ahygroscopicus + TX, Streptomyces albaduncus + TX, Streptomyces exfoliates + TX, Streptomyces galbus + TX, Streptomyces griseoplanus griseoplanus + TX, Streptomyces griseoviridis (Mycostop®) + TX, Streptomyces lydicus (Actinovate®) + TX, Streptomyces lydicus WYEC-108 (ActinoGrow®) + TX, Streptomyces violaceus + TX, Tilletiopsis minor + TX, Tilletiopsis spp.) + TX, Trichoderma asperellum (T34 Biocontrol®) + TX, Trichoderma gamsii (Tenet®) + TX, Trichoderma atroviride (Plantmate®) + TX, Trichoderma hamatum TH382 + TX, Trichoderma harzianum rifai (Mycostar®) + TX, Trichoderma harzianum T-22 (Trianum-P® + TX, PlantShield HC® + TX, RootShield® + TX, Trianum-G®) + TX, Trichoderma harzianum harzianum) T-39 (Trichodex®) + TX, Trichoderma inhamatum + TX, Trichoderma koningii + TX, Trichoderma spp.) LC52 (Sentinel®) + TX, Trichoderma lignorum + TX, Trichoderma longibrachiatum + TX, Trichoderma polysporum (Binab T®) + TX, Trichoderma taxi + TX, Trichoderma virens + TX, Trichoderma virens (formerly Gliocladium virens GL-21) (SoilGuard®) + TX, Trichoderma viride + TX, Trichoderma viride strain ICC080 (Remedier®) + TX, Trichosporon pullulans pullulans) + TX, Trichosporon spp. + TX, Trichothecium spp.) + TX, Trichothecium roseum + TX, Typhula phacorrhiza strain 94670 + TX, Typhula phacorrhiza strain 94671 + TX, Ulocladium atrum + TX, Ulocladium oudemansii (Botry-Zen®) + TX, Ustilago maydis + TX, various bacteria and supplemental micronutrients (Natural II®) + TX, various fungi (Millennium Microbes®) + TX, Verticillium chlamydosporium + TX, Verticillium lecanii lecanii (Mycotal® + TX, Vertalec®) + TX, Vip3Aa20 (VIPtera®) + TX, Virgibaclillus marismortui + TX, Xanthomonas campestris pv. Poae (Camperico®) + TX, Xenorhabdus bovienii + TX, Xenorhabdus nematophilus; Plant extracts including: pine oil (Retenol®) +TX, azadirachtin (Plasma Neem Oil® +TX, AzaGuard® +TX, MeemAzal® +TX, Molt-X® +TX, vegetable IGR (Neemazad® +TX, Neemix®) +TX, rapeseed oil (Lilly Miller Vegol®) +TX, American ant-weed (Chenopodium ambrosioides near ambrosioides) (Requiem®) +TX, chrysanthemum (Chrysanthemum) extract (Crisant®) +TX, neem oil extract (Trilogy®) +TX, Labiatae essential oil (Botania®) +TX, clove, rosemary, peppermint, and thyme oil extracts (Garden insect killer®) + TX, glycine betaine (Greenstim®) + TX, garlic + TX, lemongrass oil (GreenMatch®) + TX, neem oil + TX, catnip (Nepeta cataria) (catnip oil) + TX, catnip (Nepeta catarina) + TX, nicotine + TX, oregano oil (MossBuster®) + TX, sesame (Pedaliaceae) oil (Nematon®) + TX, daisy (butterfly) + TX, soapberry (Quillaja saponaria) (NemaQ®) + TX, Japanese knotweed (Reynoutria sachalinensis) (Regalia® + TX, Sakalia®) + TX, rotenone (Eco Roten®) + TX, Rutaceae extract (Soleo®) + TX, soybean oil (Ortho ecosense®) + TX, Tea Tree Oil (TimorexGold®) +TX, thyme oil +TX, AGNIQUE® MMF +TX, BugOil® +TX, rosemary sesame peppermint thyme and cinnamon extract mixture (EF300®) +TX, clove rosemary and peppermint extract mixture (EF400®) +TX, clove peppermint garlic oil and mint mixture (Soil Shot®) +TX, kaolin (Screen®) +TX, brown algae storage glucan (Laminarin®); Pheromones, including: blackheaded fireworm pheromone (3M Sprayable Blackheaded Fireworm Pheromone®) + TX, codling moth pheromone (Paramount dispenser-(CM) / Isomate C-Plus®) + TX, grapeberry moth pheromone (3M MEC-GBM Sprayable Pheromone®) + TX, leafroller pheromone (3M MEC-LR Sprayable Pheromone®) + TX, muskamone (Snip7 Fly Bait® + TX, Starbar Premium Fly Bait®) + TX, oriental fruit moth pheromone (3M oriental fruit moth sprayable pheromone®) + TX, peachtree moth pheromone (3M oriental fruit moth sprayable pheromone®) + TX, peachtree moth pheromone (3M MEC-LR Sprayable Pher ... Borer pheromone (Isomate-P®) + TX, Tomato Pinworm pheromone (3M Sprayable pheromone®) + TX, Entostat powder (extract from palm tree) (Exosex CM®) + TX, (E+TX, Z+TX, Z)-3+TX, 8+TX, 11-tetradecatrienyl acetate + TX, (Z+TX, Z+TX, E)-7+TX, 11+TX, 13-hexadecatrienal + TX, (E+TX, Z)-7+TX, 9-dodecadien-1-yl acetate + TX, 2-methyl-1-butanol + TX, calcium acetate + TX, Scenturion® + TX, Biolure® + TX, Check-Mate® + TX, lavandulyl senecionate; Macrobials containing: Aphelinus abdominalis + TX, Aphidius ervi (Aphelinus-System®) + TX, Acerophagus papaya + TX, Adalia bipunctata (Adalia-System®) + TX, Adalia bipunctata (Adaline®) + TX, Adalia bipunctata (Aphidalia®) + TX, Ageniaspis citricola + TX, Ageniaspis fuscicollis + TX, Amblyseius andersonii andersoni (Anderline® + TX, Andersoni-System®) + TX, Amblyseius californicus (Amblyline® + TX, Spical®) + TX, Amblyseius cucumeris (Thripex® + TX, Bugline cucumeris®) + TX, Amblyseius fallacis (Fallacis®) + TX, Amblyseius swirskii (Bugline swirskii® + TX, Swirskii-Mite®) + TX, Amblyseius womersleyi (WomerMite®) + TX, Amitus hesperidum hesperidum) + TX, Anagrus atomus + TX, Anagyrus fusciventris + TX, Anagyrus kamali + TX, AnagyrusAnagyrus loecki + TX, Anagyrus pseudococci (Citripar®) + TX, Anicetus benefices + TX, Anisopteromalus calandrae + TX, Anthocoris nemoralis (Anthocoris-System®) + TX, Aphelinus abdominalis (Apheline® + TX, Aphiline®) + TX, Aphelinus asychis + TX, Aphidius colemani (Aphipar®) + TX, Aphidius ervi (Ervipar®) + TX, Aphidius gifuensis gifuensis + TX, Aphidius matricariae (Aphipar-M®) + TX, Aphidoletes aphidimyza (Aphidend®) + TX, Aphidoletes aphidimyza (Aphidoline®) + TX, Aphytis lingnanensis + TX, Aphytis melinus + TX, Aprostocetus hagenowii + TX, Atheta coriaria (Staphyline®) + TX, Bombus spp. + TX, Bombus terrestris (Natupol®) + TX, Beehive® + TX, Bombus terrestris (Beeline® + TX, Tripol®) + TX, Cephalonomia stephanoderis + TX, Chilocorus nigritusnigritus + TX, Chrysoperla carnea (Chrysoline®) + TX, Chrysoperla carnea (Chrysopa®) + TX, Chrysoperla rufilabris + TX, Cirrospilus ingenuus + TX, Cirrospilus quadristriatus + TX, Citrostichus phyllocnistoides + TX, Closterocerus chamaeleon + TX, Closterocerus spp. + TX, Coccidoxenoides perminutus (Planopar®) + TX, Coccophagus cowperi + TX, Coccophagus lycimnia + TX, Cotesia flavipes + TX, Cotesia plutellae + TX, Cryptolaemus montrouzieri (Cryptobug® + TX, Cryptoline®) + TX, Cybocephalus nipponicus (Cybocephalus nipponicus) + TX, Dacnusa sibirica (Dacnusa sibirica) + TX, Dacnusa sibirica (Minusa®) + TX, Diglyphus isaea (Diminex®) + TX, Delphastus catalinae (Delphastus®) + TX, Delphastus pusillus + TX, Diachasmimorpha krausii + TX, Diachasmimorpha longicaudatalongicaudata + TX, Diaparsis jucunda + TX, Diaphorencyrtus aligarhensis + TX, Diglyphus isaea + TX, Diglyphus isaea (Miglyphus® + TX, Digline®) + TX, Dacnusa sibirica (DacDigline® + TX, Minex®) + TX, Diversinervus spp. + TX, Encarsia citrina + TX, Encarsia formosa (Encarsia max® + TX, Encarline® + TX, En-Strip® + TX, Eretmocerus eremicus (Enermix®) + TX, Encarsia guadeloupae + TX, Encarsia haitiensis + TX, Episyrphus balteatus (Syrphidend®) + TX, Eretmoceris siphonini + TX, Eretmocerus californicus + TX, Eretmocerus eremicus (Ercal® + TX, Eretline e®) + TX, Eretmocerus eremicus (Bemimix®) + TX, Eretmocerus hayati + TX, Eretmocerus mundus (Bemipar® + TX, Eretline m®) + TX, Eretmocerus siphonini + TX, Exochomus quadripustulatus + TX, Feltiella acarisuga (Spidend®) + TX, Feltiella acarisuga (Feltiline®) + TX, Fopius arisanus + TX, Fopius ceratitivorus + TX, Formononetin (Wirless Beehome®) + TX, Franklinothrips vespiformis (Vespop®) + TX, Galendromus occidentalis + TX, Goniozus legneri + TX, Habrobracon hebetor + TX, Harmonia axyridis (Harmoniaaxyridis (HarmoBeetle®) + TX, Heterorhabditis spp. (Lawn Patrol®) + TX, Heterorhabditis bacteriophora (NemaShield HB® + TX, Nemaseek® + TX, Terranem-Nam® + TX, Terranem® + TX, Larvanem® + TX, B-Green® + TX, NemAttack® + TX, Nematop®) + TX, Heterorhabditis megidis (Nemasys H® + TX, BioNem H® + TX, Exhibitline hm® + TX, Larvanem-M®) + TX, Hippodamia convergens + TX, Hypoaspis aculeifer (Aculeifer-System® + TX, Entomite-A®) + TX, Hypoaspis miles (Hypoline m® + TX, Entomite-M®) + TX, Lbalia leucospoides + TX, Lecanoideus floccissimus + TX, Lemophagus errabundus + TX, Leptomastidea abnormis + TX, Leptomastix dactylopii (Leptopar®) + TX, Leptomastix epona + TX, Lindorus lophanthae + TX, Lipolexis oregmae + TX, Lucilia caesar (Natufly®) + TX, Lysiphlebus testes ceipestestaceipes + TX, Macrolophus caliginosus (Mirical-N® + TX, Macroline c® + TX, Mirical®) + TX, Mesoseiulus longipes + TX, Metaphycus flavus + TX, Metaphycus lounsburyi + TX, Micromus angulatus (Milacewing®) + TX, Microterys flavus + TX, Muscidifurax raptorellus and Spalangia cameroni (Biopar®) + TX, Neodryinus typhlocybae + TX, Neoseiulus californicus + TX, Neoseiulus cucumeris (THRYPEX®) + TX, Neoseiulus fallacis + TX, Nesideocoris tenuis (NesidioBug® + TX, Nesibug®) + TX, Ophyra aenescens (Biofly®) + TX, Orius insidiosus (Thripor-I® + TX, Oriline i®) + TX, Orius laevigatus (Thripor-L® + TX, Oriline l®) + TX, Orius majus class (Orius majusculus (Oriline m®) + TX, Orius strigicollis (Thripor-S®) + TX, Pauesia juniperorum (Pauesia juniperorum) + TX, Pediobiusfoveolatus + TX, Phasmarhabditis hermaphrodita (Nemaslug®) + TX, Phymastichus coffea + TX, Phytoseiulus macropilus + TX, Phytoseiulus persimilis (Spidex® + TX, Phytoline p®) + TX, Podisus maculiventris (Podisus®) + TX, Pseudacteon curvatus + TX, Pseudacteon obtusus + TX, Pseudacteon tricuspis + TX, Pseudaphycus maculipennis + TX, Pseudleptomastix mexicana + TX, Psyllaephagus pilosus + TX, Psyttalia concolor (complex) + TX, Quadrastichus spp. + TX, Rhyzobius lophanthae + TX, Rodolia cardinalis + TX, Rumina decollate + TX, Semielacher petiolatus + TX, Sitobion avenae (Ervibank®) + TX, Steinernema carpocapsae (Nematac C (registered trademark) + TX, Millenium (registered trademark) + TX, BioNem C (registered trademark) + TX, NemAttack (registered trademark) + TX, Nemastar (registered trademark) + TX, Capsanem (registered trademark) + TX, Steinernema feltiaefeltiae (NemaShield® + TX, Nemasys F® + TX, BioNem F® + TX, Steinernema-System® + TX, NemAttack® + TX, Nemaplus® + TX, Exhibitline sf® + TX, Scia-rid® + TX, Entonem®) + TX, Steinernema kraussei (Nemasys L® + TX, BioNem L® + TX, Exhibitline srb®) + TX, Steinernema riobrave (BioVector® + TX, BioVektor®) + TX, Steinernema scapterisci (Nematac S®) + TX, Steinernema species (Steinernema spp.) + TX, Steinernematid spp. (Guardian Nematodes®) + TX, Stethorus punctillum (Stethorus®) + TX, Tamarixia radiate + TX, Tetrastichus setifer + TX, Thripobius semiluteus + TX, Torymus sinensis + TX, Trichogramma brassicae (Tricholine b®) + TX, Trichogramma brassicae (Tricho-Strip®) + TX, Trichogramma evanescens + TX, Trichogramma minutum) + TX, Trichogramma ostriniae + TX, Trichogramma pratoneri (Trichogrammaplatneri + TX, Trichogramma pretiosum + TX, Xanthopimpla stemmator; Other biological products include: abscisic acid +TX, bioSea® +TX, Chondrostereum purpureum (Chontrol Paste®) +TX, Colletotrichum gloeosporioides (Collego®) +TX, copper octanoate (Cueva®) +TX, Delta Trap (Trapline d®) +TX, Erwinia amylovora (Harpin) (ProAct® +TX, Ni-HIBIT Gold CST®) +TX, fatty acids derived from natural by-products of extra virgin olive oil (FLIPPER®) +TX, ferric phosphate (Ferri-phosphate) (Ferramol®) +TX, Funnel Trap (Trapline y®) +TX, Gallex® +TX, Grower's Secret® + TX, Homo-brassonolide + TX, Iron Phosphate (Lilly Miller Worry Free Ferramol Slug & Snail Bait®) + TX, MCP hail trap (Trapline f®) + TX, Microctonus hyperodae + TX, Mycoleptodiscus terrestris (Des-X®) + TX, BioGain® + TX, Aminomite® + TX, Zenox® + TX, pheromone trap (Thripline ams®) + TX, potassium bicarbonate (MilStop®) + TX, potassium salts of fatty acids (Sanova®) + TX, potassium silicate solution (Sil-Matrix®) + TX, potassium iodide + potassium thiocyanate (Enzicur®) + TX, SuffOil-X® + TX, spider venom + TX, Nosema locustae (Semaspore Organic Grasshopper) + TXControl®) + TX, sticky traps (Trapline YF® + TX, Rebell Amarillo®) + TX and traps (Takitrapline y+b®) + TX; (1) an antibacterial agent selected from the group consisting of: (1.1) Bacteria, examples of which are: Bacillus mojavensis strain R3B (accession number NCAIM(P)B001389) from Certis USA LLC (a subsidiary of Mitsui & Co., Ltd.) (WO 2013 / 034938) + TX; Bacillus pumilus, in particular the strain BU F-33 with NRRL accession number 50185 (available as part of BASF's CARTISSA® products, EPA registration number 71840-19) + TX; Bacillus subtilis, in particular the strain QST713 / AQ713 (available as SERENADE OPTI or SERENADE from Bayer CropScience LP, US). ASO, NRRL accession number B21661, U.S. Patent No. 6,060,051) +TX; Bacillus subtilis strain BU1814 (available as VELONDIS® PLUS, VELONDIS® FLEX, and VELONDIS® EXTRA from BASF SE) +TX; Bacillus subtilis var. amyloliquefaciens strain FZB24 having accession number DSM10271 (available as TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5) from Novozymes) +TX; Bacillus subtilis CX-9060 +TX from Certis USA LLC (a subsidiary of Mitsui & Co., Ltd.); Bacillus spp. sp.), in particular strain D747 (available as DOUBLE NICKEL® from Kumiai Chemical Industry Co., Ltd.), accession number FERM BP-8234, U.S. Pat. No. 7,094,592+TX; Paenibacillus sp. having accession number NRRL B-50972 or accession number NRRL B-67129.), strains of which are listed in WO 2016 / 154297 +TX; Paenibacillus polymyxa, in particular strain AC-1 (e.g., TOPSEED® from Green Biotech Company Ltd.) +TX; Pantoea agglomerans, in particular strain E325 (Accession No. NRRL B-21856) (available from Northwest Agri Products as BLOOMTIME BIOLOGICAL™ FD BIOPESTICIDE) +TX; Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena) +TX; and (1.2) Fungi, examples of which are: Aureobasidium pullulans, in particular blastospores of the strain DSM 14940, blastospores of the strain DSM 14941 or a mixture of blastospores of the strains DSM 14940 and DSM 14941 (for example BOTECTOR® and BLOSSOM PROTECT® from bio-ferm, CH) + TX; Pseudozyma aphidis (disclosed in WO 2011 / 151819 by Yissum Research Development Company of the Hebrew University of Jerusalem) + TX; Saccharomyces cerevisiae from Lesaffre et Compagnie, FR cerevisiae), in particular strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938 or CNCM No. 1-3939 (WO 2010 / 086790); (2) A biological bactericide or fungicide selected from the following group: (2.1) Bacteria, examples of which are Agrobacterium radiobacter strain K84 (e.g., GALLTROL-A® from AgBioChem, CA) +TX; Agrobacterium radiobacter strain K1026 (e.g., NOGALL® from BASF SE) +TX; Bacillus subtilis var. amyloliquefaciens strain FZB24 with accession number DSM10271 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5)) +TX; Bacillus amyloliquefaciens, in particular strain D747 (Double Nickel™, accession number FERM BP-8234, U.S. Pat. No. 7,094,592) +TX; Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL accession number B-50768, WO 2014 / 028521) (STARGUS® from Marrone Bio Innovations) +TX; Bacillus amyloliquefaciens strain FZB42, accession number DSM23117 (available as RHIZOVITAL® from ABiTEP, DE) +TX; Bacillus amyloliquefaciens isolate B246 (e.g., from the University of AVOGREEN™ from Pretoria) +TX; Bacillus licheniformis, in particular the strain SB3086 having accession number ATCC 55406, WO 2003 / 000051 (available as ECOGUARD™ Biofungicide and GREEN RELEAF™ from Novozymes) +TX +TX;Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (QUARTZO® (WG) and PRESENCE® (WP) from FMC Corporation) +TX; Bacillus methylotrophicus strain BAC-9912 (from the Chinese Academy of Sciences' Institute of Applied Ecology) +TX; Bacillus mojavensis strain R3B (accession number NCAIM(P)B001389) from Certis USA LLC (a subsidiary of Mitsui & Co., Ltd.) (WO 2013 / 034938) +TX; Bacillus mycoides, isolate, with accession number B-30890 (Certis USA Bacillus pumilus, particularly strain QST2808 (available from Bayer CropScience LP, US as SONATA®, accession number NRRL B-30087, described in U.S. Pat. No. 6,245,551) +TX; Bacillus pumilus, particularly strain GB34 (available from Bayer AG, DE as Yield Shield®) +TX; Bacillus pumilus, particularly strain BU F-33 having NRRL accession number 50185 (available from BASF as part of its CARTISSA products, EPA registration number 71840-19) +TX; Bacillus subtilis subtilis), in particular strain QST713 / AQ713 (available from Bayer CropScience LP, US as SERENADE OPTI or SERENADE ASO, NRRL accession number B21661, described in US Pat. No. 6,060,051)+TX;Bacillus subtilis Y1336 (available from Bion-Tech, Taiwan as BIOBAC® WP, registered in Taiwan as a biological bactericide and fungicide under registration numbers 4764, 5454, 5096, and 5277) +TX; Bacillus subtilis strain MBI600 (available from BASF SE as SUBTILEX), accession number NRRL B-50595, U.S. Pat. No. 5,061,495 +TX; Bacillus subtilis strain GB03 (available from Bayer AG, DE as Kodiak®) +TX; Bacillus subtilis strain BU1814 (available from BASF SE as VELONDIS® PLUS, VELONDIS® FLEX, and VELONDIS® EXTRA) +TX; Certis USA Bacillus subtilis CX-9060 + TX from Mitsui & Co., LLC (a subsidiary of Mitsui & Co., Ltd.); Bacillus subtilis KTSB strain (FOLIACTIVE® from Donaghys) + TX; Bacillus subtilis IAB / BS03 (AVIV® from STK Bio-Ag Technologies, PORTENTO® from Idai Nature) + TX; Bacillus subtilis strain Y1336 (available as BIOBAC® WP from BioNTech, Taiwan, registered in Taiwan as a biological fungicide under registration numbers 4764, 5454, 5096, and 5277) + TX; Paenibacillus epiphyticus from BASF SE epiphyticus (WO 2016 / 020371) + TX; Paenibacillus polymyxa ssp. plantarum (WO 2016 / 020371) + TX from BASF SE;Strains of Paenibacillus sp. having accession number NRRL B-50972 or accession number NRRL B-67129, WO 2016 / 154297 +TX; Pseudomonas chlororaphis strain AFS009, accession number NRRL B-50897, WO 2017 / 019448 (e.g., HOWLER™ and ZIO® from AgBiome Innovations, US) +TX; Pseudomonas chlororaphis, in particular strain MA342 (e.g., CEDOMON®, CERALL® and CEDRESS® from Bioagri and Koppert) +TX; Pseudomonas fluorescens Pseudomonas fluorescens strain A506 (e.g., BLIGHTBAN® A506 by NuFarm) +TX; Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena) +TX; Streptomyces griseoviridis strain K61 (also known as Streptomyces galbus strain K61) (Accession No. DSM7206) (MYCOSTOP® from Verdera, PREFENCE® from BioWorks, see Crop Protection 2006, 25, 468-475) +TX; Streptomyces lydicus strain WYEC108 (Streptomyces lydicus (also known as strain WYCD108US) (ACTINO-IRON® and ACTINOVATE® from Novozymes) +TX; and (2.2) Fungi, examples of which are: Ampelomyces quisqualis, in particular the strain AQ10 (for example AQ10® from IntrachemBio Italia) + TX; Ampelomyces quisqualis strain AQ10 with accession number CNCM1-807 (for example AQ10® from IntrachemBio Italia) + TX; Aspergillus flavus strain NRRL21882 (product known as AFLA-GUARD® from Syngenta / ChemChina) + TX; Aureobasidium pullulans, in particular blastospores of the strain DSM14940 + TX; Aureobasidium pullulans pullulans, in particular blastospores of strain DSM 14941 + TX; Aureobasidium pullulans, in particular a mixture of blastospores of strains DSM 14940 and DSM 14941 (e.g., Botector® by bio-ferm, CH) + TX; Chaetomium cupreum (accession number CABI353812) (e.g., BIOKUPRUM® by AgriLife) + TX; Chaetomium globosum (available as RIVADIOM® by Rivale) + TX; Cladosporium cladosporioides, strain H39, accession number CBS122244, U.S. Patent Application Publication No. 2010 / 0291039 (Stichting Dienst Coniothyrium minitans, in particular the strain CON / M / 91-8 (accession number DSM 9660, e.g. Contans® from Bayer CropScience Biologics GmbH) + TX;Cryptococcus flavescens, strain 3C (NRRL Y-50378), (B2.2.99) + TX; Dactylaria Candida + TX; Dilophosphora alopecuri (available as TWIST FUNGUS®) + TX; Fusarium oxysporum, strain Fo47 (available as FUSACLEAN® by Natural Plant Protection) + TX; Gliocladium catenulatum (synonym: Clonostachys rosea f. catenulate) strain J1446 (e.g., Prestop® by Lallemand) + TX; Gliocladium roseum) (also known as Clonostachys rosea f rosea), particularly strain 321U of Adjuvants Plus, strain ACM941 disclosed in Xue (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root tot complex of field pea, Can Jour Plant Sci 83(3):519-524), or strain IK726 (Jensen DF, et al. Development of a biocontrol agent for plant disease control with special emphasis on the near commercial fungal antagonist Clonostachys rosea strain 'IK726', Australas Plant Pathol. 2007,36:95-101) +TX;Lecanicillium lecanii (formerly known as Verticillium lecanii) conidia of the strain KV01 (e.g., Vertalec® by Koppert / Arysta) + TX; Metschnikowia fructicola, in particular the strain NRRL-30752, (B2.2.3) + TX; Microsphaeropsis ochracea + TX; Muscodor roseus, in particular the strain A3-5 (accession number NRRL 30548) + TX; Penicillium stickii from BASF SE steckii (DSM27859, WO 2015 / 067800) + TX; Penicillium vermiculatum + TX; Phlebiopsis gigantea strain VRA1992 (ROTSTOP® C from Danstar Ferment) + TX; Pichia anomala, strain WRL-076 (NRRL Y-30842), U.S. Pat. No. 7,579,183 + TX; Pseudozyma flocculosa, strain PF-A22 UL (available as SPORODEX® L from Plant Products Co., CA) + TX; Saccharomyces cerevisiae, particularly strain LASO2 (Agro-Levures et from Derives), strain LAS117 cell wall (CEREVISANE® from Lesaffre; ROMEO® from BASF SE), strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938, CNCM No. 1-3939 from Lesaffre et Compagnie, FR (WO 2010 / 086790) + TX; Simplicillium lanosoniveum + TX; Talaromyces flavus, strain V117b + TX; Trichoderma asperelloides JM41R (accession number NRRL B-50759) (TRICHO PLUS® from BASF SE) + TX; Trichoderma asperellum, in particular strain kd (e.g., Andermatt Trichoderma asperellum, in particular the strain SKT-1, accession number FERM P-16510 (e.g., ECO-HOPE® from Kumiai Chemical Industry Co., Ltd.), strain T34 (e.g., T34 Biocontrol from Biocontrol Technologies SL, ES) or strain ICC012 from Isagro + TX; Trichoderma atroviride, in particular the strain SC1 (accession number CBS 122089, WO 2009 / 116106 and U.S. Pat. No. 8,431,120 (Bi-PA)), strain 77B (T77 from Andermatt Biocontrol) or strain LU132 (e.g., Sentinel from Agrimm Technologies Limited) + TX; Trichoderma atroviride, in particular the strain SC1 (accession number CBS 122089, WO 2009 / 116106 and U.S. Pat. No. 8,431,120 (Bi-PA)), strain 77B (T77 from Andermatt Biocontrol) or strain LU132 (e.g., Sentinel from Agrimm Technologies Limited) + TX; atroviride, strain CNCM1-1237 (e.g., Esquive® WP from Agrauxine, FR) + TX; Trichoderma atroviride, strain number V08 / 002387 + TX; Trichoderma atroviride, strain NMI number V08 / 002388 + TX;Trichoderma atroviride, strain NMI number V08 / 002389+TX; Trichoderma atroviride, strain NMI number V08 / 002390+TX; Trichoderma atroviride, strain LC52 (e.g., Tenet by Agrimm Technologies Limited)+TX; Trichoderma atroviride, strain ATCC 20476 (IMI 206040)+TX; Trichoderma atroviride, strain T11 (IMI352941 / CECT20498)+TX; Trichoderma atroviride, strain SKT-1 (FERM P-16510), JP 11-253151 A + TX; Trichoderma atroviride, strain SKT-2 (FERM P-16511), JP 11-253151 A + TX; Trichoderma atroviride, strain SKT-3 (FERM P-17021), JP 11-253151 A + TX; Trichoderma fertile (e.g., BASF's product TrichoPlus) + TX; Trichoderma gamsii (formerly T. viride), strain ICC080 (IMI CC 392151 CABI, e.g., AGROBIOSOL DE MEXICO, SADE Trichoderma gamsii (formerly T. viride), strain ICC080 (IMI CC 392151 CABI) (available as BIODERMA® by AGROBIOSOL DE MEXICO, SADE CV) + TX; Trichoderma harmatum + TX; Trichoderma harmatum with accession number ATCC 28012 + TX;Trichoderma harzianum strain T-22 (e.g. Trianum-P from Andermatt Biocontrol or Koppert) or strain Cepa SimbT5 (from Simbiose Agro) + TX; Trichoderma harzianum + TX; Trichoderma harzianum rifai T39 (e.g. Trichodex® from Makhteshim, US) + TX; Trichoderma harzianum, strain ITEM908 (e.g. Trianum-P from Koppert) + TX; Trichoderma harzianum, strain TH35 (e.g. Root-Pro from Mycontrol) + TX; Trichoderma harzianum, strain DB103 (Dagutat available as T-GRO® 7456 by Biolab) +TX; Trichoderma polysporum, strain IMI206039 (e.g., Binab TF WP by BINAB Bio-Innovation AB, Sweden) +TX; Trichoderma stromaticum, having accession number Ts3550, (e.g., Tricovab by CEPLAC, Brazil) +TX; Trichoderma virens (also known as Gliocladium virens), in particular strain GL-21 (e.g., SoilGard by Certis, US) +TX; Trichoderma virens strain G-41, formerly Gliocladium virens virens) (Accession No. ATCC20906) (e.g., ROOTSHIELD® PLUS WP and TURFSHIELD® PLUS WP)+TX from BioWorks, US;Trichoderma viride, strain TV1 (e.g., Trianum-P according to Koppert) + TX; Trichoderma viride, in particular strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161:125-137) + TX; Trichoderma asperellum strain ICC012 (also known as Trichoderma harzianum ICC012) with accession number CABI CC IMI 392716 and Trichoderma gamsii (formerly T. viride) strain ICC080 (e.g., Isagro USA, a mixture of BIO-TAM™ by Botry-Zen Ltd, New Zealand and BIODERMA® by Agrobiosol de Mexico, SA de CV +TX; Ulocladium oudemansii strain U3 having accession number NM 99 / 06216 (e.g., BOTRY-ZEN® by Botry-Zen Ltd, New Zealand and BOTRYSTOP® by BioWorks, Inc.) +TX; Verticillium albo-atrum (formerly V. dahliae), strain WCS850 having accession number WCS850, deposited at the Central Bureau for Fungi Cultures (e.g., DUTCH TRIG® by Tree Care Innovations) +TX; Verticillium chlamydosporium +TX; (3) A biological control agent having the effect of improving plant growth and / or plant health selected from the following group: (3.1) Bacteria, examples of which are: Azospirillum brasilense (e.g., VIGOR® from KALO, Inc.) + TX; Azospirillum lipoferum (e.g., VERTEX-IF® from TerraMax, Inc.) + TX; Azorhizobium caulinodans, in particular the strain ZB-SK-5 + TX; Azotobacter chroococcum, in particular the strain H23 + TX; Azotobacter vinelandii, in particular the strain ATCC 12837 + TX; Azotobacter vinelandii and Clostridium pasteurianum a mixture with Bacillus pasteurianum (available as INVIGORATE® from Agrinos) + TX; Bacillus amyloliquefaciens pm414 (LOLI-PEPTA® from Biofilm Crop Protection) + TX; Bacillus amyloliquefaciens SB3281 (ATCC #PTA-7542, WO 2017 / 205258) + TX; Bacillus amyloliquefaciens TJ1000 (available as QUIKROOTS® from Novozymes) + TX; Bacillus amyloliquefaciens, in particular the strain IN937a + TX; Bacillus amyloliquefaciens amyloliquefaciens, in particular the strain FZB42 (e.g. RHIZOVITAL® from ABiTEP, DE) + TX; Bacillus amyloliquefaciens BS27 (accession number NRRL B-5015) + TX; Bacillus cereus EE128 (NRRL number B-50917) + TX;Bacillus cereus family EE349 (NRRL No. B-50928) + TX; Bacillus cereus, in particular strain BP01 (ATCC 55675, e.g., MEPICHLOR® from Arysta Lifescience, US) + TX; Bacillus firmus, in particular strain CNMC1-1582 (e.g., VOTIVO® from BASF SE) + TX; Bacillus mycoides BT155 (NRRL No. B-50921) + TX; Bacillus mycoides EE118 (NRRL No. B-50918) + TX; Bacillus mycoides EE141 (NRRL No. B-50916) + TX; Bacillus mycoides BT46-3 (NRRL No. B-50922) + TX; Bacillus pumilus, in particular strain QST2808 (Accession No. NRRL No. B-30087) + TX; Bacillus pumilus, in particular strain GB34 (e.g., YIELD SHIELD® from Bayer Crop Science, DE) + TX; Bacillus siamensis, in particular strain KCTC13613T + TX; Bacillus subtilis, in particular strain QST713 / AQ713 (NRRL Accession No. B-21661, as described in U.S. Pat. No. 6,060,051, Bayer Crop Science, DE) + TX. LP, US as SERENADE® OPTI or SERENADE® ASO) + TX; Bacillus subtilis, particularly strain AQ30002 (accession number NRRL B-50421, described in U.S. Patent Application Publication No. 13 / 330,576) + TX; Bacillus subtilis, particularly strain AQ30004 (as well as NRRL B-50455, described in U.S. Patent Application Publication No. 13 / 330,576) + TX;Bacillus subtilis strain BU1814, (available as TEQUALIS® from BASF SE), Bacillus subtilis rm303 (RHIZOMAX® from Biofilm Crop Protection) +TX; Bacillus thuringiensis BT013A (NRRL No. B-50924) (also known as Bacillus thuringiensis 4Q7) +TX; a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available as QUARTZO® (WG), PRESENCE® (WP) from FMC Corporation) +TX; Bacillus subtilis, particularly strain MBI600 (e.g., BASF SUBTILEX® from BASF SE) + TX; Bacillus tequilensis, in particular the strain NII-0943 + TX; Bradyrhizobium japonicum (e.g. OPTIMIZE® from Novozymes) + TX; Delftia acidovorans, in particular the strain RAY209 (e.g. BIOBOOST® from Brett Young Seeds) + TX; Mesorhizobium cicer (e.g. NODULATOR from BASF SE) + TX; Lactobacillus sp. (e.g. LACTOPLANT® from LactoPAFI) + TX; Rhizobium leguminosarium biovar viceae (e.g. BASF NODULATOR from Sourcon Padena) + TX; Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena) + TX;Pseudomonas aeruginosa, in particular the strain PN1 + TX; Rhizobium leguminosarum, in particular the biovar bv.viceae strain Z25 (accession number CECT 4585) + TX; Paenibacillus polymyxa, in particular the strain AC-1 (e.g., TOPSEED® from Green Biotech Company Ltd.) + TX; Serratia marcescens, in particular the strain SRM (accession number MTCC 8708) + TX; Sinorhizobium meliloti strain NRG-185-1 (NITRAGIN® GOLD from Bayer CropScience) + TX; Bacillus sp. (e.g., Cropaid Ltd.) UK's CROPAID®) +TX; and (3.2) Fungi, examples of which are: Purpureocillium lilacinum (formerly known as Paecilomyces lilacinus), strain 251 (AGAL 89 / 030550, e.g. BioAct from Bayer CropScience Biologics GmbH) +TX; Penicillium bilaii, strain ATCC 22348 (e.g. JumpStart from Acceleron BioAg), Talaromyces flavus, strain V117b +TX; Trichoderma atroviride, strain CNCM1-1237 (e.g. Esquive WP from Agrauxine, FR), Trichoderma viride ... viride), e.g., strain B35 (Pietr et al., 1993, Zesz. Nauk.AR w Szczecinie 161:125-137) + TX; Trichoderma atroviride strain LC52 (also known as Trichoderma atroviride strain LU132, e.g., Sentinel from Agrimm Technologies Limited) + TX; Trichoderma atroviride strain SC1 described in International Patent Application No. PCT / IT2008 / 000196 + TX; Trichoderma asperellum strain kd (e.g., T-Gro from Andermatt Biocontrol) + TX; Trichoderma asperellum strain Eco-T (Plant Health Products, ZA), Trichoderma harzianum strain T-22 (e.g., Andermatt Trianum-P from Biocontrol or Koppert) +TX; Myrothecium verrucaria strain AARC-0255 (e.g., DiTera™ from Valent Biosciences) +TX; Penicillium bilaii strain ATCC ATCC20851 +TX; Pythium oligandrum strain M1 (ATCC38472, e.g., Polyversum from Bioprepraty, CZ) +TX; Trichoderma virens strain GL-21 (e.g., SoilGard™ from Certis, USA) +TX; Verticillium albo-atrum (formerly V. dahliae) strain WCS850 (CBS276).92, e.g. Dutch Trig from Tree Care Innovations) +TX; Trichoderma atroviride, in particular strain number V08 / 002387, strain number NMI number V08 / 002388, strain number NMI number V08 / 002389, strain number NMI number V08 / 002390 +TX; Trichoderma harzianum strain ITEM908, Trichoderma harzianum strain TSTh20 +TX; Trichoderma harzianum strain 1295-22 +TX; Pythium oligandrum strain DV74 +TX; Rhizopogon amylopogon (e.g. Helena Chemical Rhizopogon fulvigleba (e.g., in Helena Chemical Company's Myco-Sol) + TX; Trichoderma virens strain GI-3 + TX; (4) an insecticidal biological control agent selected from the following: (4.1) Bacteria, examples of which are Agrobacterium radiobacter strain K84 (e.g., Galltrol from AgBioChem Inc.) + TX; Bacillus amyloliquefaciens, in particular the strain PTS-4838 (e.g., AVEO from Valent Biosciences, US) + TX; Bacillus firmus, in particular the strain CNMC1-1582 (e.g., VOTIVO® from BASF SE) + TX; Bacillus mycoides, isolate J. (e.g., BmJ from Certis USA LLC (a subsidiary of Mitsui & Co., Ltd.)) + TX; Bacillus sphaericus sphaericus, in particular serotype H5a5b strain 2362 (strain ABTS-1743) (e.g., VECTOLEX® from Valent BioSciences, US) + TX; Bacillus thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372, e.g., XENTARI® from Valent BioSciences) + TX; Bacillus thuringiensis subsp. aizawai, in particular serotype H-7 (e.g., FLORBAC® WG from Valent BioSciences, US) + TX; Bacillus thuringiensis israelensis strain BMP144 (e.g., Becker Microbial AQUABAC® + TX by Products, IL; Bacillus thuringiensis subsp.israelensis (serotype H-14) strain AM65-52 (Accession No. ATCC1276) (e.g., VECTOBAC® from Valent BioSciences, US) +TX; Bacillus thuringiensis subsp. aizawai strain GC-91 +TX; Bacillus thuringiensis var. Colmeri (e.g., TIANBAOBTC from Changzhou Jianghai Chemical Factory) +TX; Bacillus thuringiensis var. japonensis strain Buibui +TX; Bacillus thuringiensis subsp. kurstaki strain BMP123 +TX from Becker Microbial Products, IL; Bacillus thuringiensis subsp. kurstaki strain BMP123 by Bayer CropScience Products, IL, e.g., BARITONE+TX from Bayer CropScience; Bacillus thuringiensis subsp. kurstaki strain HD-1 (e.g., DIPEL® ES from Valent BioSciences, US)+TX; Bacillus thuringiensis var. kurstaki strain EVB-113-19 (e.g., BIOPROTEC® from AEF Global)+TX; Bacillus thuringiensis subsp. kurstaki strain ABTS351+TX; Bacillus thuringiensis subsp. kurstaki) strain PB54+TX; Bacillus thuringiensis subsp. kurstaki (Bacillus thuringiensis subsp.kurstaki strain SA11 (JAVELIN from Certis, US) + TX; Bacillus thuringiensis subsp. kurstaki strain SA12 (THURICIDE from Certis, US) + TX; Bacillus thuringiensis subsp. kurstaki strain EG2348 (LEPINOX from Certis, US) + TX; Bacillus thuringiensis subsp. kurstaki strain EG7841 (CRYMAX from Certis, US) + TX; Bacillus thuringiensis subsp. tenebrionis strain NB176 (SD-5428, e.g., BioFa DE's NOVODOR® FC) + TX; Brevibacillus laterosporus (Ecolibrium Biologicals' LATERAL) + TX; Burkholderia spp.), in particular Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis strain MBI305) (Accession No. NRRL B-50319 +TX; WO 2011 / 106491 and WO 2013 / 032693 +TX; e.g., MBI206 TGAI and ZELTO® from Marrone Bio Innovations) +TX; Chromobacterium subtsugae, in particular strain PRAA4-1T (MBI-203 +TX; e.g., GRANDEVO® from Marrone Bio Innovations) +TX; Lecanicillium muscarium muscarium Ve6 (MYCOTAL from Koppert) + TX; Paenibacillus popilliae (formerly Bacillus popilliae) + TX; e.g., MILKY SPORE POWDER™ and MILKY SPORE GRANULAR™ from St. Gabriel Laboratories + TX; Pasteuria nishizawae strain Pn1 (CLARIVA from Syngenta / ChemChina) + TX; Serratia entomophila (e.g., INVADE® from Wrightson Seeds) + TX; Serratia marcescens, particularly strain SRM (accession number MTCC 8708) + TX; Trichoderma asperellum asperellum (TRICHODERMAX from Novozymes) + TX; Wolbachia pipientis ZAP strain (e.g., ZAP MALES® from MosquitoMate) + TX; and (4.2) Fungi, examples of which are: Beauveria bassiana strain ATCC 74040 (e.g. NATURALIS® from Intrachem Bio Italia) + TX; Beauveria bassiana strain GHA (accession number ATCC 74250, e.g. BOTANIGUARD® ES and MYCONTROL-O® from Laverlam International Corporation) + TX; Beauveria bassiana strain ATP02 (accession number DSM 24665) + TX; Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus) strain Apopka97 PREFERAL from SePRO + TX; Metarhizium anisopliae anisopliae 3213-1 (deposited as NRRL accession number 67074) (WO 2017 / 066094 + TX; Pioneer Hi-Bred International) + TX; Metarhizium robertsii 15013-1 (deposited as NRRL accession number 67073) + TX; Metarhizium robertsii 23013-3 (deposited as NRRL accession number 67075) + TX; Paecilomyces lilacinus strain 251 (MELOCON, Certis, US) + TX; Zoophtora radicans + TX; (5) A virus selected from the group consisting of Adoxophyes orana (smaller apple tortrix) granulosis virus (GV) + TX; Cydia pomonella (codling moth) granulosis virus (GV) + TX; Helicoverpa armigera (helicobacterium armigera) nucleopolyhedrovirus (NPV) + TX; Spodoptera exigua (beet armyworm) mNPV + TX; Spodoptera frugiperda (stalk armyworm) mNPV + TX; Spodoptera littoralis (Egyptian armyworm) NPV + TX; (6) Bacteria and fungi that can be added as an "inoculant" to plants or plant parts or plant tissues and that promote plant growth and plant health due to their specific properties, selected from the following: Agrobacterium spp. + TX; Azorhizobium caulinodans + TX; Azospirillum spp. + TX; Azotobacter spp. + TX; Bradyrhizobium spp. + TX; Burkholderia spp., especially Burkholderia cepacia (formerly known as Pseudomonas cepacia) + TX; Gigaspora spp. spp.) or Gigaspora monosporum + TX; Glomus spp. + TX; Laccaria spp. + TX; Lactobacillus buchneri + TX; Paraglomus spp. + TX; Pisolithus tinctorus + TX; Pseudomonas spp. + TX; Rhizobium spp., especially Rhizobium trifolii + TX; Rhizopogon spp. + TX; Scleroderma spp. + TX; Suillus spp. spp.) + TX;Streptomyces spp.) + TX; (7) Plant extracts and products formed by microorganisms containing proteins and secondary metabolites that can be used as biological control agents, selected from the following: garlic (Allium sativum) (Eco-Spray's NEMGUARD + TX; ADAMA's BRALIC) + TX; Armour-Zen + TX; Artemisia absinthium + TX; azadirachtin (e.g., AZATIN XL from Certis, US) + TX; Biokeeper WP + TX; Brassicaceae extracts, in particular rapeseed powder or mustard powder + TX; Cassia nigricans + TX; Celastrus angulatus + TX; Chenopodium anthelminticum + TX; chitin + TX; Dryopteris filix-mas + TX; Equisetum arvense arvense) + TX; Fortune Aza + TX; Fungastop + TX; Heads Up (Quinoa (Chenopodium quinoa) saponin extract) + TX; PROBLAD (Natural Blad Polypeptide derived from lupine seeds), Certis EU + TX; FRACTURE (Natural Blad Polypeptide derived from lupine seeds), FMC + TX; Calystegia / Pyrethrin + TX; Cassia amara + TX; Quercus + TX; Quillaja extract (BASF's QL AGRI35) + TX; Reynoutria sachalinensis extract (Marrone Bio's REGALLIA / REGALIA MAXX) + TX; Requiem™ Insecticide + TX; Rotenone + TX; Ryania / Ryanodine + TX; Comfrey (Symphytum) officinale) + TX; Tansy (Tanacetum vulgare) + TX; Thymol + TX; Thymol mixed with geraniol (CEDROZ by Eden Research) + TX; Thymol mixed with geraniol and eugenol (MEVALONE by Eden Research) + TX; Triact70 + TX;TriCon + TX; nasturtium (Tropaeulum majus) + TX; tea tree (Melaleuca alternifolia) extract (STK's TIMOREX GOLD) + TX; nettle (Urtica dioica) + TX; veratrine + TX; and mistletoe (Viscum album) + TX; and Safeners such as benoxacor + TX, cloquintocet (including cloquintocet-mexyl) + TX, cyprosulfamide + TX, dichlormid + TX, fenchlorazole (including fenchlorazole-ethyl) + TX, fenclorim + TX, fluxofenim + TX, furilazole + TX, isoxadifen (including isoxadifen-ethyl) + TX, mefenpyr (including mefenpyr-diethyl) + TX, metcamifen + TX, and oxabetrinil + TX.

[0221] 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.

[0222] The compounds of formula (I) defined in any one of embodiments 1 to 43 are usually used in the form of compositions and can be applied to the crop area or plants to be treated simultaneously or successively with further compounds. These further compounds can be, for example, fertilizers or trace element donors or other preparations that influence plant growth. They can be selective or non-selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides, or mixtures of several of these preparations, optionally containing further carriers, surfactants or application-promoting adjuvants customarily used in the formulation field.

[0223] The compounds of formula (I) as defined in any one of embodiments 1 to 43 can be used in the form of a (fungicidal) composition for the control or protection against phytopathogenic microorganisms, comprising as active ingredient at least one compound of formula (I) as defined in any one of embodiments 1 to 43 or at least one preferred individual compound as defined above in free form or in agrochemically usable salt form, and at least one of the adjuvants described above.

[0224] Accordingly, the present invention provides a composition, preferably a fungicidal composition, comprising at least one compound of formula (I) as defined in any one of embodiments 1 to 43, 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) as defined in any one of embodiments 1 to 43, at least one compound effective for controlling pests, for example an additional fungicidal active ingredient.

[0225] A further aspect of the present invention relates to a method for controlling or preventing infestation of 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, in particular by phytopathogenic or spoilage microorganisms or organisms that are potentially harmful to humans, such as fungal organisms, which method comprises applying a compound of formula (I) as defined in any one of embodiments 1 to 43 or a preferred individual compound as defined above as active ingredient to the plant, to part of the plant or its habitat, to its propagation material or to any part of the non-living material.

[0226] Control or prevention means reducing infestation by plant pathogenic or spoilage microorganisms or organisms that are potentially harmful to humans, such as insects or especially fungal organisms, to a level that demonstrates improvement.

[0227] A preferred method for controlling or preventing infestation of crop plants by phytopathogenic microorganisms, particularly fungal organisms, comprising the application of a compound of formula (I) as defined in any one of embodiments 1 to 43 or an agrochemical composition containing at least one of said compounds, is foliar treatment. The frequency and amount of application will depend on the risk of infestation by the corresponding pathogen or insect. However, the compound of formula (I) as defined in any one of embodiments 1 to 43 can also be introduced into the plant through the roots via the soil (systemic action) by drenching the plant habitat with a liquid formulation or by applying the compound to the soil in solid form, for example, in granular form (soil application). In the case of rice crops, such granules can be applied to flooded rice fields. The compound of formula (I) as defined in any one of embodiments 1 to 43 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.

[0228] Formulations, e.g., compositions containing a compound of formula (I) as defined in any one of embodiments 1 to 43 and, optionally, a solid or liquid adjuvant or monomer encapsulating the compound of formula (I) as defined in any one of embodiments 1 to 43, can be prepared in a known manner, typically by homogeneously mixing and / or grinding the compounds together with extenders, e.g., solvents, solid carriers and, optionally, surface-active compounds (surfactants).

[0229] Another subject of the present invention is a method of applying the composition to control the above-mentioned types of pests, such as spraying, atomizing, dusting, brushing, dressing, spreading, or pouring, which should be selected to suit the intended purpose and use of the composition to control the above-mentioned types of pests in the prevalent situation. Typical concentration rates are 0.1 to 1000 ppm, preferably 0.1 to 500 ppm, of active ingredient. The application rate per hectare is preferably 1 g to 2000 g of active ingredient / hectare, more preferably 10 to 1000 g / ha, and most preferably 10 to 600 g / ha. When used as a seed drench, a convenient dosage is 10 mg to 1 g of active substance per kg of seeds.

[0230] When the combinations of the invention are used for seed treatment, an amount of 0.001 to 50 g of a compound of formula (I) per kg of seed, preferably 0.01 to 10 g per kg of seed, will generally be sufficient.

[0231] Advantageously, the composition comprising a compound of formula (I) as defined in any one of embodiments 1 to 43 according to the present invention is applied prophylactically, meaning before the onset of disease, or therapeutically, meaning after the onset of disease.

[0232] The compositions of the present invention may be in any conventional form, such as, for example, two-part systems, dry seed treatment powders (DS), seed treatment emulsions (ES), seed treatment flowable concentrates (FS), seed treatment solutions (LS), seed treatment water dispersible powders (WS), seed treatment capsule suspensions (CF), seed treatment gels (GF), emulsion concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water dispersible granules (WG), emulsifiable granules (WG), 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 fluids (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 desirable formulation in combination with agriculturally acceptable adjuvants.

[0233] Such compositions can be prepared in a conventional manner, for example, by mixing the active ingredient with appropriate inert ingredients (diluents, solvents, fillers, and optionally other ingredients such as surfactants, biocides, antifreeze agents, spreading agents, thickeners, and compounds providing adjuvant activity). Conventional slow-release formulations can also be employed when long-lasting efficacy is intended. In particular, formulations applied in spray form, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules, can contain surfactants such as wetting and dispersing agents, such as condensates of formaldehyde and naphthalenesulfonates, alkylarylsulfonates, ligninsulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated fatty alcohols, as well as other compounds providing adjuvant effects.

[0234] The seed dressing formulation is applied to seeds in a manner known per se and utilizes the combination and diluent of the present invention in a suitable seed dressing formulation form, such as an aqueous suspension or a dry powder form with good adhesion to the seeds. Such seed dressing formulations are known in the art. The seed dressing formulation may contain a single active ingredient or may contain a combination of active ingredients in encapsulated form, for example, as slow-release capsules or microcapsules.

[0235] Typically, the formulations comprise 0.01 to 90% by weight of an active agent, 0 to 20% of an agriculturally acceptable surfactant, and 10 to 99.99% of solid or liquid inert compounding agents and adjuvants, where the active agent is at least a compound of formula (I) as defined in any one of embodiments 1 to 43, together with components (B) and (C), and optionally other active agents, particularly fungicides or preservatives. Concentrated forms of the compositions generally contain about 2 to 80% by weight, preferably about 5 to 70% by weight, of the active agent. Application forms of the formulations may contain, for example, 0.01 to 20% by weight, preferably 0.01 to 5% by weight, of the active agent. While commercial products will preferably be formulated as concentrates, end users will typically utilize diluted formulations.

[0236] Although it is preferred to formulate commercial products as concentrates, end users will typically dilute the formulations before use. [Example]

[0237] The following examples illustrate the present invention. Certain compounds of the present invention can be distinguished from known compounds by their higher efficacy at low application rates, which can be verified by those skilled in the art using the experimental procedures outlined in the examples.

[0238] Throughout this description, temperatures are given in degrees Celsius (°C) and "mp." means melting point. LC / MS means liquid chromatography mass spectrometry, and a description of the equipment and methods follows.

[0239] The LC / MS equipment and method are as follows: - Method A: Spectra were recorded on a Waters mass spectrometer (SQD, SQDII single quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive or negative ion, capillary: 3.00 kV, cone range: 30 V, extractor: 2.00 V, source temperature: 150 °C, desolvation temperature: 350 °C, cone gas flow: 50 l / h, desolvation gas flow: 650 l / h, mass range: 100-900 Da) and a Waters Acquity UPLC: binary pump, heated column compartment, diode-array detector, and ELSD detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm; Temperature: 60 °C; DAD wavelength range (nm): 210–500; 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. - 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, 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.

[0240] - Method 1 and Method 2: Spectra were recorded using the following method 1 or 2 on one of the instruments described below: - Agilent 1100 series LC / MSD system equipped with DAD / ELSD Alltech2000ES and Agilent LC / MSD VL(G1956B), SL(G1956B) mass spectrometer. - Agilent 1200 series LC / MSD system equipped with DAD / ELSD Alltech3300 and Agilent LC / MSD G6130A, G6120B mass spectrometer. - Agilent Technologies 1260 Infinity LC / MSD system equipped with a DAD / ELSD Alltech3300 and an Agilent LC / MSD G6120B mass spectrometer. - Agilent Technologies 1260 Infinity II LC / MSD system equipped with a DAD / ELSD G7102A 1290 Infinity II and an Agilent LC / MSD G6120B mass spectrometer. - Agilent 1260 series LC / MSD system equipped with DAD / ELSD and Agilent LC / MSD (G6120B) mass spectrometer. - UHPLC Agilent 1290 series LC / MSD system equipped with DAD / ELSD and Agilent LC / MSD (G6125B) mass spectrometer.

[0241] Method 1 Details: - Column: Agilent Poroshell 120 SB-C18 4.6 x 30 mm 2.7 μm - Column temperature: 60℃ - Mobile phase: A-water (0.1% formic acid), B-acetonitrile (0.1% formic acid) - Flow rate: 3ml / 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: 83~600m / z - UV detection: 215nm, 254nm, 280nm

[0242] Method 2 Details: - Column: Agilent Poroshell 120 SB-C18 4.6 x 30 mm 2.7 μm - Temperature: 60℃ - Mobile phase: A-water (0.1% formic acid), B-acetonitrile (0.1% formic acid) - Flow rate: 3ml / min - Gradient: 0.01 min - 1% B, 1.5 min - 100% B, 2.2 min - 100% B - MS ionization mode: Electrospray ionization (ESI) - MS scan range: 83~1000m / z - UV detection: 215nm, 254nm, 280nm

[0243] 1 H NMR spectra were recorded at 400 MHz on a Bruker 400 MHz or Varian Unity 400 spectrometer using CDCl or DMSO-d as solvent and tetramethylsilane as internal standard. Chemical shifts are reported in ppm downfield from the standard (tetramethylsilane = 0.00 ppm), and coupling constants are in Hz.

[0244] Table A below summarizes compounds of formula (I): - LC / MS data, e.g., retention time (RT), [M+H] + and the type of method (Method A, Method B, Method 1 or Method 2), and / or - Melting point (mp).

[0245] [Table 2-1] [Table 2-2] [Table 2-3] [Table 2-4]

Table 2-5

Table 2-6

Table 2-7

Table 2-8

Table 2-9

Table 2-10

Table 2-11

Table 2-12

Table 2-13

Table 2-14

Table 2-15

Table 2-16

Table 2-17

Table 2-18

Table 2-19

Table 2-20

Table 2-21

Table 2-22

Table 2-23

Table 2-24

Table 2-25

Table 2-26

Table 2-27

Table 2-28

Table 2-29

Table 2-30

Table 2-31

Table 2-32

Table 2-33

Table 2-34

Table 2-35

Table 2-36

Table 2-37

Table 2-38

[0246] Compound 129 was unambiguously characterized by NMR on a Brucker AVANCE III 400 MHz. 1H NMR(DMSO-d6,400MHz)δ:10.48(s,1H),8.40(d,J=2.3Hz,1H),8.34(s,1H),8.02(d,J=8.6Hz,1H),7.79(s,1H),7.74(dd,J=8.7,2.5Hz, 1H),7.50(d,J=9.4Hz,1H),7.39-7.32(m,4H),7.14(d,J=9.3Hz,1H),3.87(q,J=7.1,7.1,2H),3.74(s,3H),1.09(t,J=7.0,7.0Hz,3H).

[0247] Compound 166 was unambiguously characterized by NMR on a Brucker AVANCE III 400 MHz. 1 H NMR(DMSO-d6,400MHz)δ:1.08-1.33(t,3H),2.43-2.48(q,2H),3.35-3.39(s,3H),7.05-7.22(m,3H),7.35-7.41(m,2H) ),7.50(d,J=9.4Hz,1H),7.77-7.82(m,2H),8.26(d,J=8.5Hz,1H),8.35(s,1,H),8.41(d,J=2.0Hz,1H),10.66(s,1H).

[0248] Compound 213 was unambiguously characterized by NMR on a Brucker AVANCE III 400 MHz. 1 H NMR(DMSO-d6,400MHz)δ:10.34(s,1H),8.21(d,1H),7.89(d,1H),7.47-7.58(m,2H),7. 41(s,1H),7.15-7.20(m,1H),6.93-7.0(m,1H),6.56-6.61(m,1H),6.27(s,1H),5.75(br s,2H),3.64(app s,6H),3.25(s,3H).

[0249] Example 1: This example illustrates the preparation of methyl N-[4-[6-[(4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate (compound 11).

[0250] Step 1: Preparation of methyl 3-(4-aminophenyl)imidazo[1,2-a]pyridine-6-carboxylate [ka] Methyl 3-bromoimidazo[1,2-a]pyridine-6-carboxylate (1000 mg, 3.80 mmol, 1.00 equiv.) and (4-aminophenyl)boronic acid hydrochloride (893 mg, 4.94 mmol, 1.30 equiv.) were dissolved in dioxane (57 mL) and water (5.7 mL) to give a yellow solution. Cesium carbonate (3130 mg, 9.51 mmol, 2.50 equiv.) was added, and the mixture was purged with a stream of argon for 5 minutes. CATACXIUM® PdG (146 mg, 0.190 mmol, 0.05 equiv.) was then added, and the reaction mixture was heated at 80° C. overnight. The mixture was cooled, diluted with ethyl acetate, and treated with a saturated solution of NaHCO. The desired material was extracted with ethyl acetate, and the combined organic layers were washed with water, brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel cartridge (ethyl acetate / MeOH) to give methyl 3-(4-aminophenyl)imidazo[1,2-a]pyridine-6-carboxylate as a beige solid. LC / MS (Method A) Retention time = 0.40 min; [M+H] + =268 1 H NMR(400MHz,CDCl3)δ:9.01(dd,J=1.1,1.8Hz,1H),7.75-7.71(m,1H),7.68(s,1H), 7.67-7.64(m,1H),7.38-7.33(m,2H),6.89-6.84(m,2H),3.94(s,3H),3.93-3.88(br s,2H).

[0251] Step 2: Preparation of methyl 3-[4-(methoxycarbonylamino)phenyl]imidazo[1,2-a]pyridine-6-carboxylate [ka] A mixture of methyl 3-(4-aminophenyl)imidazo[1,2-a]pyridine-6-carboxylate (905 mg, 3.22 mmol, 1.00 equiv.) and pyridine (1280 mg, 1.31 mL, 16.1 mmol, 5.00 equiv.) was dissolved in ethyl acetate (36 mL). Methyl chloroformate (614 mg, 0.502 mL, 6.43 mmol, 3.00 equiv.) was added dropwise at 20–25°C, and the mixture was stirred at room temperature for an additional 4 h. The reaction mixture was then treated with a saturated solution of NaHCO3. The precipitate that formed was filtered and washed with water and ethyl acetate to give methyl 3-[4-(methoxycarbonylamino)phenyl]imidazo[1,2-a]pyridine-6-carboxylate as an off-white solid. LC / MS (Method A) retention time = 0.66 min; [M+H] + =326 1 H NMR(400MHz,DMSO-d6)δ:9.92(br s,1H),8.95-8.91(m,1H),7.82(s,1H),7.76-7.71(m,1H),7.71-7.65(m,3H),7.64-7.59(m,2H),3.88(s,3H),3.72(s,3H).

[0252] Step 3: Preparation of 3-[4-(methoxycarbonylamino)phenyl]imidazo[1,2-a]pyridine-6-carboxylic acid [ka] Methyl 3-[4-(methoxycarbonylamino)phenyl]imidazo[1,2-a]pyridine-6-carboxylate (818 mg, 2.34 mmol, 1.00 equiv) was dissolved in 3:1 THF / water (40 mL). Lithium hydroxide (150 mg, 3.51 mmol, 1.50 equiv) was then added, and the mixture was stirred at room temperature for 4 hours. The mixture was then diluted with water (10 mL), and the THF was removed under reduced pressure. The residue was acidified with 2N HCl to a pH of 4. The suspension was filtered, and the resulting solid was washed with water and dried under vacuum to give 3-[4-(methoxycarbonylamino)phenyl]imidazo[1,2-a]pyridine-6-carboxylic acid as an off-white solid. LC / MS (Method A) retention time = 0.32 min; [M+H] + =310 1 H NMR(400MHz,DMSO-d6)δ 13.75-12.89(br s,1H),9.89(br s,1H),8.93(t,J=1.1Hz,1H),7.84(s,1H),7.74-7.67(m,3H),7.64-7.58(m,2H),3.72(s,3H).

[0253] Step 4: Preparation of methyl N-[4-[6-[(4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate [ka] To a solution of 3-[4-(methoxycarbonylamino)phenyl]imidazo[1,2-a]pyridine-6-carboxylic acid (0.042 mmol, 1 equiv.) in dimethylacetamide (0.24 mL) was added a solution of N-methyl-4-fluoroaniline (0.084 mmol, 2 equiv.) in dimethylacetamide (0.40 mL), diisopropylethylamine (0.252 mmol, 6.0 equiv.), and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl) (0.105 mmol, 2.5 equiv.). The vial was sealed and stirred at 70 °C for 16 h. All volatiles were removed under reduced pressure, and the resulting slurry was dissolved in methanol (1 mL), filtered, and concentrated under reduced pressure again. The crude residue was dissolved in dimethylacetamide (900 uL) and transferred to preparative HPLC for purification to give methyl N-[4-[6-[(4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate as an off-white solid). LC / MS (Method A) retention time = 0.71 min; [M+H] + =419 1H NMR(400MHz,DMSO-d6)δ 9.87(br s,1H),8.30(s,1H),7.68(s,1H),7.66(d,J=8.7Hz,2H),7.51(dd,J=0.7,9.4Hz,1H),7 .41-7.34(m,2H),7.27(d,J=8.7Hz,2H),7.22-7.06(m,3H),3.72(s,3H),3.37(s,3H).

[0254] Example 2: This example illustrates the preparation of methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate (compound 19).

[0255] Step 1: Preparation of methyl 8-methylimidazo[1,2-a]pyridine-6-carboxylate [ka] Methyl 8-bromoimidazo[1,2-a]pyridine-6-carboxylate (750 mg, 2.65 mmol, 1 equiv.), methylboronic acid (323 mg, 5.29 mmol, 2 equiv.), potassium carbonate (731 mg, 5.29 mmol, 2 equiv.), and THF (20 mL) were placed in a sealed tube. The reaction mixture was degassed with argon for 2 minutes, and then chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) (104 mg, 0.132 mmol, 0.05 equiv.) was added. The reaction mixture was stirred at 80 °C for 6 hours. After cooling to room temperature, the reaction mixture was filtered through a Celite pad and washed with ethyl acetate. The filtrate was washed with water, then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to give methyl 8-methylimidazo[1,2-a]pyridine-6-carboxylate as an off-white solid. 1H NMR(400MHz,CDCl3)δ:8.81(s,1H),7.70(d,J=1.2Hz,1H),7.66(d,J=1.2Hz,1H),7.54(s,1H),3.95(s,3H),2.65(s,3H).

[0256] Step 2: Preparation of methyl 3-iodo-8-methyl-imidazo[1,2-a]pyridine-6-carboxylate [ka] To a stirred solution of methyl 8-methylimidazo[1,2-a]pyridine-6-carboxylate (530 mg, 2.37 mmol, 1 equiv.) in dimethylformamide (10 mL) at room temperature was added N-iodosuccinimide (1.07 g, 4.74 mmol, 2 equiv.). The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with water, then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to afford methyl 3-iodo-8-methyl-imidazo[1,2-a]pyridine-6-carboxylate as a brown solid. 1 H NMR(400MHz,CDCl3)δ:8.76(s,1H),7.79(s,1H),7.67(s,1H),3.99(s,3H),2.76(s,3H).

[0257] Step 3: Preparation of methyl 3-[4-(methoxycarbonylamino)phenyl]-8-methyl-imidazo[1,2-a]pyridine-6-carboxylate [ka] Methyl 3-iodo-8-methyl-imidazo[1,2-a]pyridine-6-carboxylate (50.0 mg, 0.127 mmol, 1 equivalent), methyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (commercially available, CAS844500-75-0, 77.9 mg, 0.253 mmol, 2 equivalents), potassium carbonate (2 mol / L, 0.127 mL, 0.253 mmol, 2 equivalents), and 1,4-dioxane (5 mL) were placed in a sealed tube. The reaction mixture was degassed with argon for 2 minutes, after which chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) (4.98 mg, 0.00633 mmol, 0.05 equiv.) was added. The reaction mixture was stirred at 80 °C for 6 hours under microwave irradiation. After cooling to room temperature, the reaction mixture was filtered through a Celite pad and further flushed with ethyl acetate. The filtrate was washed with water, then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to give methyl 3-[4-(methoxycarbonylamino)phenyl]-8-methyl-imidazo[1,2-a]pyridine-6-carboxylate as an off-white solid. 1 H NMR(400MHz,DMSO-d6)δ:9.91(s,1H),8.79(s,1H),7.6(s,1H),7.67(d,J=8.5Hz,2H)7.58(d,J=8.5Hz,2H),7.52(br s,1H),3.86(s,3H),3.71(s,3H),2.57(s,3H).

[0258] Step 4: Preparation of 3-[4-(methoxycarbonylamino)phenyl]-8-methyl-imidazo[1,2-a]pyridine-6-carboxylic acid [ka] To a stirred solution of methyl 3-[4-(methoxycarbonylamino)phenyl]-8-methyl-imidazo[1,2-a]pyridine-6-carboxylate (30.0 mg, 0.0796 mmol, 1 equiv.) in a 3:1 mixture of THF:water (5 mL) was added lithium hydroxide monohydrate (6.68 mg, 0.159 mmol, 2 equiv.) at 0 °C. The reaction mixture was stirred at room temperature for 3 h and then concentrated under reduced pressure. The resulting residue was diluted with water and acidified with saturated aqueous NaHSO. The precipitate was filtered and dried under reduced pressure to give 3-[4-(methoxycarbonylamino)phenyl]-8-methyl-imidazo[1,2-a]pyridine-6-carboxylic acid, which was used in the next step without further purification. 1 H NMR(400MHz,DMSO-d6)δ:13.24(br s,1H),9.90(s,1H)8.78(s,1H),7.76(s,1H),7.67(d,J=8.8Hz,2H),7.58(d,J=8.8Hz,2H),7.49-7.53(m,1H),3.70(s,3H),2.56(s,3H).

[0259] Step 5: Preparation of methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate [ka] To a stirred solution of 3-[4-(methoxycarbonylamino)phenyl]-8-methyl-imidazo[1,2-a]pyridine-6-carboxylic acid (90.0 mg, 0.241 mmol, 1 equiv.) in pyridine (4 mL) was added 4-chloro-N-methyl-aniline (40.9 mg, 0.722 mmol, 1.2 equiv.). Then, phosphorus(V) oxychloride (0.0661 mL, 0.722 mmol, 5 equiv.) was added at 0 °C. The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was quenched with ice water and extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous NaHSO4, then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by reverse phase chromatography to give methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate as an amorphous white solid. 1 H NMR(400MHz,CDCl3)δ:7.95(s,1H),7.60(s,1H),7.50(d,J=8.1Hz,2H),7.33(d,J=8.6Hz,2H),7.12(s,1H),7.01-7.10(m,4H),6.81(br s,1H),3.85(s,3H),3.47(s,3H),2.56(s,3H).

[0260] Example 3: This example illustrates the preparation of methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-5-methyl-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate (compound 20).

[0261] Step 1: Preparation of methyl 5-methylimidazo[1,2-a]pyridine-6-carboxylate [ka] Methyl 6-amino-2-methyl-pyridine-3-carboxylate (50.0 mg, 0.295 mmol, 1 equiv.), ethanol (3 mL), and 2-chloroacetaldehyde (231 mg, 1.47 mmol, 5 equiv.) were placed in a sealed tube. The reaction mixture was stirred at 80 °C for 16 h. After cooling to room temperature, the reaction mixture was poured into pre-stirred cold saturated aqueous NaHCO3 and stirred for 10 min. The reaction mixture was then diluted with dichloromethane. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography to afford methyl 5-methylimidazo[1,2-a]pyridine-6-carboxylate as a brown solid. 1 H NMR(400MHz,DMSO-d6)δ:8.49(s,1H),8.30(s,1H),8.17(d,J=9.5Hz,1H),7.90(d,J=9.5Hz,1H),3.93(s,3H),3.03(s,3H).

[0262] Step 2: Preparation of methyl 3-iodo-5-methyl-imidazo[1,2-a]pyridine-6-carboxylate [ka] To a stirred solution of methyl 5-methylimidazo[1,2-a]pyridine-6-carboxylate (50.0 mg, 0.197 mmol, 1 equiv.) in dimethylformamide (0.5 mL) at room temperature was added N-iodosuccinimide (44.4 mg, 0.197 mmol, 1 equiv.). The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with water, then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to afford methyl 3-iodo-5-methyl-imidazo[1,2-a]pyridine-6-carboxylate as an off-white solid. 1 H NMR(400MHz,DMSO-d6)δ:7.73(br s,1H),7.53-7.56(m,2H),3.86(m,3H),3.38(s,3H).

[0263] Step 3: Preparation of methyl 3-[4-(methoxycarbonylamino)phenyl]-5-methyl-imidazo[1,2-a]pyridine-6-carboxylate [ka] A microwave vial was charged with methyl 3-iodo-5-methyl-imidazo[1,2-a]pyridine-6-carboxylate (450 mg, 1.42 mmol, 1 equiv.), methyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (commercially available, CAS 844500-75-0, 592 mg, 2.14 mmol, 1.5 equiv.), cesium carbonate (928 mg, 2.85 mmol, 2 equiv.), 1,4-dioxane (10 mL), and water (2 mL). The reaction mixture was degassed with argon for 5 minutes, after which Pd(dppf)Cl (104 mg, 0.142 mmol, 0.1 equiv.) was added and degassed for an additional 2 minutes. The reaction mixture was heated to 90 °C under microwave irradiation and stirred for 16 hours. After cooling to room temperature, the reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with water and then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to give methyl 3-[4-(methoxycarbonylamino)phenyl]-5-methyl-imidazo[1,2-a]pyridine-6-carboxylate as an off-white solid. 1 H NMR(400MHz,DMSO-d6)δ:9.86(s,1H),7.57-7.60(m,2H),7.56(s,1H),7.54(d ,J=8.5Hz,2H),7.42(d,J=8.5Hz,2H),3.84(s,3H),3.70(s,3H),2.45(s,3H).

[0264] Step 4: Preparation of 3-[4-(methoxycarbonylamino)phenyl]-5-methyl-imidazo[1,2-a]pyridine-6-carboxylic acid [ka] To a stirred solution of methyl 3-[4-(methoxycarbonylamino)phenyl]-5-methyl-imidazo[1,2-a]pyridine-6-carboxylate (10.0 mg, 0.00295 mmol, 1 equiv.) in THF (2 mL) and methanol (0.5 mL) was added a solution of lithium hydroxide monohydrate (2.60 mg, 0.00589 mmol, 2 equiv.) in water (0.5 mL) at room temperature. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was diluted with water and extracted with tert-butyl methyl ether. The aqueous layer was acidified with saturated aqueous NaHSO4, resulting in the formation of a precipitate. The precipitate was dissolved in ethyl acetate, washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give 3-[4-(methoxycarbonylamino)phenyl]-5-methyl-imidazo[1,2-a]pyridine-6-carboxylic acid, which was used in the next step without further purification. 1 H NMR(400MHz,DMSO-d6)δ:13.20(br s,1H),9.86(s,1H),7.62(d,J=7.6Hz,1H),7.51-7.58(m,4H),7.41(d,J=8.5Hz,2H),3.70(s,3H),2.47(s,3H).

[0265] Step 5: Preparation of methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-5-methyl-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate [ka] To a stirred solution of 3-[4-(methoxycarbonylamino)phenyl]-5-methyl-imidazo[1,2-a]pyridine-6-carboxylic acid (110 mg, 0.304 mmol, 1 equiv.) in pyridine (2 mL) was added 4-chloro-N-methyl-aniline (64.6 mg, 0.456 mmol, 1.5 equiv.). Phosphorus(V) oxychloride (0.0836 mL, 0.913 mmol, 5 equiv.) was then added at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for an additional hour. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with water, then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to give methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-5-methyl-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate. 1 H NMR(400MHz,CDCl3)δ:7.46(m,4H),7.15-7.26(m,3H),6.89-7.03(m,4H),6.80(s,1H),3.82(s,3H),3.45(br s,3H),2.10(br s,3H).

[0266] Example 4: This example illustrates the preparation of methyl N-[4-[7-chloro-6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate (compound 23).

[0267] Step 1: Preparation of methyl 2-amino-4-chloro-1,2-dihydropyridine-5-carboxylate [ka] 4-Chloro-5-iodo-pyridin-2-amine (100 mg, 0.393 mmol, 1 equiv.), triethylamine (0.110 mL, 0.786 mmol, 2 equiv.), and methanol (10 mL) were placed in an autoclave. After the reaction mixture was degassed with argon for 5 minutes, 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (16.0 mg, 0.0196 mmol, 0.05 equiv.) was added, which was then degassed for another 5 minutes. The reaction mixture was stirred at 100°C under a CO atmosphere (100 PSI) for 16 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The resulting residue was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with water and then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to give methyl 2-amino-4-chloro-1,2-dihydropyridine-5-carboxylate as an off-white solid. 1 H NMR(400MHz,DMSO-d6)δ:8.49(s,1H),7.06(s,2H),6.52(s,1H),3.76(s,3H).

[0268] Step 2: Preparation of methyl 7-chloroimidazo[1,2-a]pyridine-6-carboxylate [ka] Methyl 2-amino-4-chloro-1,2-dihydropyridine-5-carboxylate (1.20 g, 6.04 mmol, 1 equiv.), ethanol (20 mL), and 2-chloroacetaldehyde (0.474 g, 6.04 mmol, 1 equiv.) were placed in an autoclave. The reaction mixture was stirred at 80 °C for 16 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with water, then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography to afford methyl 7-chloroimidazo[1,2-a]pyridine-6-carboxylate as an off-white solid. 1H NMR(400MHz,DMSO-d6)δ:9.34(d,J=0.8Hz,1H),8.12(dd,J=0.8,1.3Hz,1H),7.87(s,1H),7.73(d,J=1.3Hz,1H),3.88(s,3H).

[0269] Step 3: Preparation of methyl 7-chloro-3-iodoimidazo[1,2-a]pyridine-6-carboxylate [ka] To a stirred solution of methyl 7-chloroimidazo[1,2-a]pyridine-6-carboxylate (900 mg, 3.42 mmol, 1 equiv.) in dimethylformamide (9 mL) at room temperature was added N-iodosuccinimide (1.15 g, 5.13 mmol, 1.5 equiv.). The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with water, then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to afford methyl 7-chloro-3-iodoimidazo[1,2-a]pyridine-6-carboxylate as a brown solid. 1 H NMR(400MHz,CDCl3)δ:8.77(s,1H),7.77(s,1H),7.73(s,1H),4.01(s,3H).

[0270] Step 4: Preparation of methyl 7-chloro-3-[4-(methoxycarbonylamino)phenyl]imidazo[1,2-a]pyridine-6-carboxylate [ka] A microwave vial was charged with methyl 7-chloro-3-iodoimidazo[1,2-a]pyridine-6-carboxylate (800 mg, 2.26 mmol, 1 equiv.), methyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (commercially available, CAS 844500-75-0, 939 mg, 3.39 mmol, 1.5 equiv.), cesium carbonate (1.47 g, 4.52 mmol, 2 equiv.), 1,4-dioxane (15 mL), and water (2 mL). The reaction mixture was degassed with argon for 5 minutes, after which Pd(dppf)Cl (165 mg, 0.226 mmol, 0.1 equiv.) was added and degassed for an additional 2 minutes. The reaction mixture was heated at 90 °C under microwave irradiation and stirred for 16 hours. After cooling to room temperature, the reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with water and then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to give methyl 7-chloro-3-[4-(methoxycarbonylamino)phenyl]imidazo[1,2-a]pyridine-6-carboxylate as an off-white solid. 1 H NMR(400MHz,DMSO-d6)δ:9.91(s,1H),8.91(s,1H),7.93(s,1H),7.83(s,1H),7.67(d,J=8.8Hz,2H),7.61(d,J=8.8Hz,2H),3.85(s,3H),3.71(s,3H).

[0271] Step 5: Preparation of 7-chloro-3-[4-(methoxycarbonylamino)phenyl]imidazo[1,2-a]pyridine-6-carboxylic acid [ka] To a stirred solution of methyl 7-chloro-3-[4-(methoxycarbonylamino)phenyl]imidazo[1,2-a]pyridine-6-carboxylate (550 mg, 1.53 mmol, 1 equiv.) in THF (10 mL) and methanol (10 mL) was added a solution of lithium hydroxide monohydrate (128 mg, 3.06 mmol, 2 equiv.) in water (2 mL) at room temperature. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure. The resulting residue was diluted with water and neutralized with 2 M HCl. A precipitate formed, which was filtered and dried under reduced pressure to give 7-chloro-3-[4-(methoxycarbonylamino)phenyl]imidazo[1,2-a]pyridine-6-carboxylic acid as an off-white solid, which was used in the next step without further purification. 1 H NMR(400MHz,DMSO-d6)δ:13.54(br s,1H),9.90(s,1H),8.90(s,1H),7.89(s,1H),7.82(s,1H),7.66(d,J=8.8Hz,2H),7.61(d,J=8.8Hz,2H),3.70(s,3H).

[0272] Step 6: Preparation of methyl N-[4-[7-chloro-6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate [ka] To a stirred solution of 7-chloro-3-[4-(methoxycarbonylamino)phenyl]imidazo[1,2-a]pyridine-6-carboxylic acid (200 mg, 0.550 mmol, 1 equiv.) in pyridine (5 mL) was added 4-chloro-N-methyl-aniline (93.4 mg, 0.659 mmol, 1.2 equiv.). Then, phosphorus(V) oxychloride (0.252 mL, 2.75 mmol, 5 equiv.) was added at 0° C. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with water, then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to give methyl N-[4-[7-chloro-6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate as an off-white solid. 1 H NMR(400MHz,DMSO-d6)δ:9.90(s,1H),8.60(br s,1H),7.76(br s,1H),7.72(br s,1H),7.65(d, J=8.3Hz,2H),7.30-7.48(m,6H),3.71(s,3H),3.32(s,3H).

[0273] Example 5: This example illustrates the preparation of N-[5-[6-[(4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (Example 25).

[0274] Step 1: Preparation of methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate [ka] 2-Aminopyridine-5-boronic acid pinacol ester (2000 mg, 8.63 mmol, 1.00 equiv) and pyridine (2.79 g, 2.85 mL, 34.5 mmol, 4.00 equiv) were dissolved in ethyl acetate (50 mL) and cooled to 10 °C. Methyl chloroformate (3.30 g, 2.70 mL, 34.5 mmol, 4.00 equiv) was then added dropwise at 10–15 °C. After the addition was complete, the mixture was stirred at room temperature for an additional 2 h. The mixture was then diluted with ethyl acetate, treated with a saturated solution of NaHCO3, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate as a white solid, which was used in the next step without further purification. LC / MS (Method A) retention time = 0.16 min; [M+H] + =279 1 H NMR(400MHz,CDCl3)δ:8.64(dd,J=0.9,1.7Hz,1H),8.10-8.05(m,1H),7.99(dd,J=0.7,8.4Hz,1H),7.28(s,1H),3.83(s,3H),1.37(s,12H)

[0275] Step 2: Preparation of lithium 3-[6-(methoxycarbonylamino)-3-pyridyl]imidazo[1,2-a]pyridine-6-carboxylate [ka] Methyl 3-bromoimidazo[1,2-a]pyridine-6-carboxylate (3000 mg, 11.76 mmol, 1.00 equiv.) and methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (5010 mg, 17.1 mmol, 1.50 equiv.) were dissolved in dioxane (75 mL) and water (7.5 mL). Cesium carbonate (7510 mg, 22.8 mmol, 2.0 equiv.) was added, and the mixture was purged with a stream of argon for 5 minutes. CATACXIUM® Pd G3 (437 mg, 0.570 mmol, 0.05 equiv.) was then added, and the reaction mixture was heated to 85°C for 17 hours. The mixture was cooled to room temperature and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure, and the resulting suspension was filtered. The solid was washed with ethyl acetate and dried under vacuum to give methyl 3-[6-(methoxycarbonylamino)-3-pyridyl]imidazo[1,2-a]pyridine-6-carboxylate as a yellow solid. The crude residue (2140 mg, 6.23 mmol, 1.00 equiv) was dissolved in a 3:1 mixture of THF / water (152 mL), lithium hydroxide (400 mg, 1.50 equiv, 9.35 mmol) was added, and the reaction mixture was stirred at room temperature for 17 hours. The mixture was filtered and washed with THF. The resulting solid was dried under vacuum to give lithium 3-[6-(methoxycarbonylamino)-3-pyridyl]imidazo[1,2-a]pyridine-6-carboxylate as an off-white solid. LC / MS (Method A) Retention time = 0.25 min; [M] - =311 1 H NMR(400MHz,DMSO-d6)δ:10.42(br s,1H),8.75(s,1H),8.52(d,J=1.8Hz,1H),8.14-8.00(m,2H),7.79-7.70(m,2H),7.49(br d,J=0.7Hz,1H),3.72(s,3H).

[0276] Step 3: Preparation of methyl N-[5-[6-[(4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate [ka] To a mixture of lithium 3-[6-(methoxycarbonylamino)-3-pyridyl]imidazo[1,2-a]pyridine-6-carboxylate (1 equiv., 0.042 mmol) in dimethylacetamide (0.24 mL) was added a solution of N-methyl-4-fluoroaniline (2 equiv., 0.084 mmol) in dimethylacetamide (0.40 mL), diisopropylethylamine (6.0 equiv., 0.252 mmol), and a stock solution of bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl) (2.5 equiv., 0.101 mmol). The reaction mixture was stirred at 70 °C for 16 h and then cooled to room temperature. All volatiles were removed under reduced pressure. The resulting residue was dissolved in methanol (1 mL), filtered, and concentrated under reduced pressure. The crude residue was dissolved in dimethylacetamide (900 uL) and purified by HPLC to give methyl N-[5-[6-[(4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate as an off-white solid. LC / MS (Method A) retention time = 0.70 min; [M+H] + =420 1 H NMR(400MHz,CDCl3)δ:8.29-8.19(m,2H),8.15(d,J=8.4Hz,1H),7.93(br s,1H),7.69(s,1H),7.58(dd,J=2.4,8.5Hz,1H),7.49(d,J=9.4Hz,1H),7.16(dd,J=1.8,9.4Hz,1H),7.13-7.02(m,4H),3.89(s,3H),3.49(s,3H).

[0277] Example 6: This example illustrates the preparation of methyl N-[4-[6-[(4-chlorophenyl)-(cyanomethyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate (compound 31).

[0278] Step 1: Preparation of 3-bromo-N-(4-chlorophenyl)imidazo[1,2-a]pyridine-6-carboxamide [ka] A mixture of 3-bromoimidazo[1,2-a]pyridine-6-carboxylic acid (500 mg, 1.0 equiv., 1.97 mmol), 4-chloroaniline (308 mg, 1.2 equiv., 2.36 mmol), and diisopropylethylamine (1290 mg, 5.0 equiv., 9.85 mmol, 1.73 mL) was dissolved in dimethylacetamide (15 mL). After stirring the mixture at room temperature for 5 minutes, propanephosphonic anhydride (50 wt.% in ethyl acetate, 3140 mg, 2.93 mL, 4.93 mmol, 2.5 equiv.) was added. The reaction was heated at 40°C for 2 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, quenched with a saturated solution of NaHCO3, and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography (cyclohexane / ethyl acetate) to give 3-bromo-N-(4-chlorophenyl)imidazo[1,2-a]pyridine-6-carboxamide as a beige solid. LC / MS (Method A) retention time = 0.92 min; [M+H] + =352 1 H NMR(400MHz,DMSO-d6)δ:10.69(s,1H),9.01(s,1H),7.96-7.72(m,4H),7.52-7.37(m,2H).

[0279] Step 2: Preparation of 3-bromo-N-(4-chlorophenyl)-N-(cyanomethyl)imidazo[1,2-a]pyridine-6-carboxamide [ka] To a solution of 3-bromo-N-(4-chlorophenyl)imidazo[1,2-a]pyridine-6-carboxamide (74.0 mg, 1.00 equiv., 0.194 mmol) in methyltetrahydrofuran (3 mL) cooled to 0 °C was added sodium hydride (11.8 mg, 1.50 equiv., 0.291 mmol), and the resulting mixture was warmed to room temperature and stirred for approximately 2 h. The reaction mixture was again cooled to 0 °C, and 2-bromoacetonitrile (48.7 mg, 2.00 equiv., 0.394 mmol, 0.028 mL) was added dropwise at 0-5 °C. The mixture was then stirred at 55 °C for 17 h. The mixture was diluted with ethyl acetate, treated with a saturated solution of NaHCO3, and extracted with ethyl acetate. The combined organic layers were then washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was used directly in the next step. LC / MS (Method A) Retention time = 0.86 min, [M+H] + =391 1 H NMR(400MHz,CDCl3)δ:8.39-8.33(m,1H),7.67-7.60(m,2H),7.42-7.35(m,2H),7.23-7.15(m,2H),7.07-7.01(m,1H),4.76(s,2H).

[0280] Step 3: Preparation of methyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate [ka] A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2.00 g, 1.00 equiv., 8.95 mmol) and pyridine (2.17 g, 3.00 equiv., 26.8 mmol, 2.21 mL) was dissolved in ethyl acetate (100 mL). Methyl chloroformate (1.71 g, 2.00 equiv., 17.9 mmol, 1.40 mL) was then added dropwise at 10 °C, and the mixture was stirred at room temperature for 2 h. The mixture was diluted with ethyl acetate, treated with a saturated solution of NaHCO3, and extracted twice with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography (cyclohexane / ethyl acetate) to give methyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate as a colorless oil. LC / MS (Method A) Retention time = 1.00 min; [M+H] + =278 1 H NMR(400MHz,CDCl3)δ:7.70-7.83(m,2H),7.33-7.47(m,2H),6.57-6.77(m,1H),3.79(s,3H),1.34(s,12H).

[0281] Step 4: Preparation of methyl N-[5-[6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate [ka] A mixture of 3-bromo-N-(4-chlorophenyl)-N-(cyanomethyl)imidazo[1,2-a]pyridine-6-carboxamide (50.0 mg, 1.00 equiv., 0.116 mmol) and methyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (43.8 mg, 1.30 equiv., 0.150 mmol) was dissolved in dioxane (0.8 mL) and water (0.24 mL). Cesium carbonate (76.0 mg, 2.00 equiv., 0.231 mmol) was added, and the reaction mixture was flushed with argon for 5 minutes. CATACXIUM® Pd G3 (4.43 mg, 0.05 equiv., 0.00578 mmol) was then added, and the mixture was microwaved at 95 °C for 45 minutes. The mixture was diluted with ethyl acetate, treated with a saturated solution of NaHCO3, and extracted with ethyl acetate. The combined organic layers were then washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by reverse-phase preparative HPLC (water / acetonitrile) to afford 9 mg of methyl N-[5-[6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate as an off-white solid. LC / MS (Method A) retention time = 0.77 min; [M+H] + =460 1 H NMR(400MHz,CDCl3)δ:8.28-8.34(m,1H),7.63-7.68(m,1H),7.47-7.59(m,3H),7 .38-7.44(m,2H),7.13-7.23(m,5H),6.91-7.00(m,1H),4.72(s,2H),3.87(s,3H).

[0282] Example 7: This example illustrates the preparation of methyl N-[4-[6-[(4-chlorophenyl)-prop-2-ynyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate (compound 33).

[0283] Step 1: Preparation of 3-bromo-N-(4-chlorophenyl)-N-prop-2-ynyl-imidazo[1,2-a]pyridine-6-carboxamide [ka] To 3-bromoimidazo[1,2-a]pyridine-6-carboxylic acid (112 mg, 0.44 mmol, 1.0 equiv.) in methyltetrahydrofuran (4.5 mL) at room temperature were added dimethylformamide (3.3 mg, 0.003 mL, 0.044 mmol, 0.1 equiv.) and oxalyl chloride (68.6 mg, 0.047 mL, 0.53 mmol, 1.20 equiv.). After 3 h, the reaction mixture was evaporated to dryness to give 3-bromoimidazo[1,2-a]pyridine-6-carbonyl chloride as a crude residue. In a separate flask, 4-chloro-N-prop-2-yl-aniline (79.0 mg, 0.44 mmol, 1.0 equiv.) and pyridine (106 mg, 0.11 mL, 1.32 mmol, 3.0 equiv.) were dissolved in methyltetrahydrofuran (4 mL). This mixture was added to the 3-bromoimidazo[1,2-a]pyridine-6-carbonyl chloride prepared above, and the resulting mixture was stirred at 70 °C for 16 h. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate, treated with a saturated solution of NaHCO3, and extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography (cyclohexane / ethyl acetate) to give 3-bromo-N-(4-chlorophenyl)-N-prop-2-ynyl-imidazo[1,2-a]pyridine-6-carboxamide as a yellow resin. LC / MS (Method A) retention time = 0.91 min; [M+H] + =388 1H NMR(400MHz,CDCl3)δ:8.36(dd,J=0.9,1.7Hz,1H),7.64(s,1H),7.38(dd,J=0.9,9.4Hz,1H),7.36-7.3 2(m,2H),7.22-7.17(m,2H),7.08(dd,J=1.7,9.4Hz,1H),4.70(d,J=2.6Hz,2H),2.33(t,J=2.4Hz,1H).

[0284] Step 2: Preparation of methyl N-[4-[6-[(4-chlorophenyl)-prop-2-ynyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate [ka] In a microwave vial, 3-bromo-N-(4-chlorophenyl)-N-prop-2-ynyl-imidazo[1,2-a]pyridine-6-carboxamide (80.0 mg, 0.189 mmol, 1.0 equiv.) and methyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (71.8 mg, 0.246 mmol, 1.3 equiv.) were dissolved in dioxane (2.8 mL) and water (0.8 mL). Cesium carbonate (125.0 mg, 0.379 mmol, 2.0 equiv.) was added, and the reaction mixture was purged with argon. Finally, tetrakis(triphenylphosphine)palladium(0) (11.1 mg, 0.05 equiv., 0.01 mmol) was added, and the reaction mixture was heated at 100 °C for 80 min under microwave irradiation. The mixture was diluted with ethyl acetate, treated with a saturated solution of NaHCO3, and extracted with ethyl acetate. The combined organic layers were then washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography (cyclohexane / ethyl acetate) to give methyl N-[4-[6-[(4-chlorophenyl)-prop-2-ynyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate as a yellow solid. LC / MS (Method A) Retention time = 0.86 min, [M+H] + =391 1 H NMR(400MHz,CDCl3)δ:8.31-8.28(m,1H),7.64(s,1H),7.56(d,J=8.4Hz,2H),7.50(dd,J=0 .7,9.5Hz,1H),7.39-7.33(m,2H),7.23(dd,J=1.8,9.5Hz,1H),7.21-7.13(m,4H),7.09(br s,1H),4.66(d,J=2.6Hz,2H),3.85(s,3H),2.29(t,J=2.4Hz,1H).

[0285] Example 8: This example illustrates the preparation of methyl N-[4-[7-bromo-6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate (compound 34).

[0286] Step 1: Preparation of 4-bromo-5-iodo-pyridin-2-amine [ka] To a stirred solution of 4-bromopyridin-2-amine (500 mg, 2.75 mmol, 1 equiv) in acetonitrile (10 mL) at room temperature was added N-iodosuccinimide (1.23 g, 5.49 mmol, 1.5 equiv). The reaction mixture was stirred at 50° C. for 24 hours. After cooling to room temperature, the reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to afford 4-bromo-5-iodo-pyridin-2-amine as a brown solid. 1 H NMR(400MHz,DMSO-d6)δ:8.19(s,1H),6.87(s,1H),6.37(br s,2H).

[0287] Step 2: Preparation of 7-bromo-6-iodoimidazo[1,2-a]pyridine [ka] 4-Bromo-5-iodo-pyridin-2-amine (10.5 g, 31.6 mmol, 1 equiv.) and 2-chloroacetaldehyde (45%, 22.3 mL, 158 mmol, 5 equiv.) were placed in a sealed tube. The reaction mixture was stirred at 80 °C for 16 h. After cooling to room temperature, the reaction mixture was poured into pre-stirred cold saturated aqueous NaHCO3 and allowed to stir for 5 min. The reaction mixture was then diluted with ethyl acetate. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography to afford 7-bromo-6-iodoimidazo[1,2-a]pyridine as an off-white solid. 1 H NMR(400MHz,CDCl3)δ:8.57(s,1H),8.02(s,1H),7.61(s,1H),7.54(s,1H).

[0288] Step 3: Preparation of methyl 7-bromoimidazo[1,2-a]pyridine-6-carboxylate [ka] 7-Bromo-6-iodoimidazo[1,2-a]pyridine (6.40 g, 17.8 mmol, 1 equiv.), sodium acetate (3.66 g, 44.6 mmol, 2.5 equiv.), 1,4-bis(diphenylphosphino)butane (0.761 g, 1.78 mmol, 0.1 equiv.), and methanol (100 mL) were placed in an autoclave. The reaction mixture was degassed with nitrogen for 5 minutes, and then bis(triphenylphosphine)palladium(II) chloride (0.626 g, 0.892 mmol, 0.05 equiv.) was added. The reaction mixture was stirred at 80 °C under a CO atmosphere (200 PSI) for 16 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The crude residue was purified by flash chromatography to give methyl 7-bromoimidazo[1,2-a]pyridine-6-carboxylate as a brown solid. 1 H NMR(400MHz, CDCl3)δ:8.83(s,1H),7.97(s,1H),7.70-7.72(m,1H),7.65(br s,1H),3.97(s,3H).

[0289] Step 4: Preparation of 7-bromoimidazo[1,2-a]pyridine-6-carboxylic acid [ka] To a stirred solution of methyl 7-bromoimidazo[1,2-a]pyridine-6-carboxylate (3.30 g, 11.6 mmol, 1 equiv.) in a 4:4:2 mixture of THF:methanol:water (40 mL) at room temperature was added lithium hydroxide monohydrate (0.977 g, 23.3 mmol, 2 equiv.). The reaction mixture was stirred at room temperature for 1 hour and then concentrated under reduced pressure. The resulting residue was diluted with water and acidified with saturated aqueous NaHSO. A precipitate formed, which was filtered and dried under reduced pressure to give 7-bromoimidazo[1,2-a]pyridine-6-carboxylic acid as a brown solid, which was used in the next step without further purification. 1 H NMR(400MHz,DMSO-d6)δ:13.21-13.75(br s,1H),9.27(s,1H),8.08(s,1H),7.99(s,1H)7.68(d,J=1.0Hz,1H).

[0290] Step 5: Preparation of 7-bromo-N-(4-chlorophenyl)-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide [ka] To a stirred solution of 7-bromoimidazo[1,2-a]pyridine-6-carboxylic acid (50.0 mg, 0.176 mmol, 1 equiv.) in dimethylformamide (2 mL) was added 4-chloro-N-methyl-aniline (30.0 mg, 0.212 mmol, 1.2 equiv.), triethylamine (0.0737 mL, 0.529 mmol, 3 equiv.), and propanephosphonic anhydride (50 wt.% in ethyl acetate, 0.210 mL, 0.353 mmol, 2 equiv.). The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with ethyl acetate, washed with water and then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to afford 7-bromo-N-(4-chlorophenyl)-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide as an off-white solid. 1 H NMR(400MHz,DMSO-d6)δ:8.56-8.79(m,1H),7.89(br s,2H)7.59(br s,1H)7.25-7.45(m,4H)3.38(br s,3H).

[0291] Step 6: Preparation of 7-bromo-N-(4-chlorophenyl)-3-iodo-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide [ka] To a stirred solution of 7-bromo-N-(4-chlorophenyl)-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide (800 mg, 2.15 mmol, 1 equiv.) in acetonitrile (20 mL) at room temperature was added N-iodosuccinimide (967 mg, 4.30 mmol, 2 equiv.). After stirring the reaction mixture at room temperature for 16 hours, it was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to afford 7-bromo-N-(4-chlorophenyl)-3-iodo-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide as a brown solid. 1H NMR(400MHz,DMSO-d6)δ:8.46(br s,1H),7.92(br s,1H),7.70(br s,1H),7.26-7.47(m,4H),3.40(br s,3H).

[0292] Step 7: Preparation of methyl N-[4-[7-bromo-6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate [ka] A microwave vial was charged with 7-bromo-N-(4-chlorophenyl)-3-iodo-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide (50.0 mg, 0.0917 mmol, 1 equiv.), methyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (commercially available, CAS 844500-75-0, 42.4 mg, 0.138 mmol, 1.5 equiv.), cesium carbonate (59.8 mg, 0.183 mmol, 2 equiv.), 1,4-dioxane (1.5 mL), and water (0.5 mL). The reaction mixture was degassed with argon for 2 minutes, after which cataCXium® A Pd G3 (3.34 mg, 0.00459 mmol, 0.05 equiv) was added. The reaction mixture was then stirred at 90° C. for 1 hour under microwave irradiation. After cooling to room temperature, the reaction mixture was filtered through a Celite pad and washed with ethyl acetate. The filtrate was washed with water, then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to give methyl N-[4-[7-bromo-6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate as an off-white solid. 1H NMR(400MHz,DMSO-d6)δ:9.90(s,1H),8.56(br s,1H)7.92(br s,1H),7.70(br s,1H),7.65(d,J=8.6Hz,2H),7.29-7.55(m,6H),3.71(s,3H),3.36(br s,3H).

[0293] Example 9: This example illustrates the preparation of methyl N-[4-[8-bromo-6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate (compound 35).

[0294] Step 1: Preparation of 8-bromoimidazo[1,2-a]pyridine-6-carboxylic acid [ka] To a stirred solution of methyl 8-bromoimidazo[1,2-a]pyridine-6-carboxylate (2.00 g, 7.84 mmol, 1 equiv.) in THF (10 mL) and methanol (5 mL) was added a solution of lithium hydroxide monohydrate (0.658 g, 15.7 mmol, 2 equiv.) in water (5 mL) at room temperature. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure. The resulting residue was diluted with water and neutralized with 2 M HCl. A precipitate formed, which was filtered and dried under reduced pressure to give 8-bromoimidazo[1,2-a]pyridine-6-carboxylic acid as an off-white solid, which was used in the next step without further purification. 1 H NMR(400MHz,DMSO-d6)δ:9.40(d,J=1.3Hz,1H),8.33(d,J=1.3Hz,1H),8.03(d,J=1.3Hz,1H),7.89(d,J=1.3Hz,1H).

[0295] Step 2: Preparation of 8-bromo-N-(4-chlorophenyl)-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide [ka] To a stirred solution of 8-bromoimidazo[1,2-a]pyridine-6-carboxylic acid (1.40 g, 5.81 mmol, 1 equiv.) in pyridine (20 mL) was added 4-chloro-N-methyl-aniline (0.822 g, 5.81 mmol, 1 equiv.). Phosphorus(V) oxychloride (2.66 mL, 29.0 mmol, 5 equiv.) was then added at 0 °C. The reaction mixture was then warmed to room temperature and stirred for an additional 1 h. The reaction mixture was quenched with saturated aqueous NaHCO3, diluted with water, and extracted twice with ethyl acetate. The combined organic layers were washed with water, then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to afford 8-bromo-N-(4-chlorophenyl)-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide as an off-white solid. 1 H NMR(400MHz,CDCl3)δ:8.29(d,J=1.0Hz,1H),7.77(s,1H),7.61(s,1H),7.30-7.34(m,2H),7.29(d,J=1.2Hz,1H),7.04-7.09(m,2H),3.49(s,3H).

[0296] Step 3: Preparation of 8-bromo-N-(4-chlorophenyl)-3-iodo-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide [ka] To a stirred solution of 8-bromo-N-(4-chlorophenyl)-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide (500 mg, 1.30 mmol, 1 equiv.) in dimethylformamide (3 mL) was added N-iodosuccinimide (440 mg, 1.95 mmol, 1.5 equiv.) at room temperature. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was then diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to afford 8-bromo-N-(4-chlorophenyl)-3-iodo-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide as a brown solid. 1 H NMR(400MHz,DMSO-d6)δ:8.17(d,J=1.2Hz,1H),7.78(s,1H),7.51(d,J=1.2Hz,1H),7.39(s,4H),3.40(s,3H).

[0297] Step 4: Preparation of methyl N-[4-[8-bromo-6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate [ka] A microwave vial was charged with 8-bromo-N-(4-chlorophenyl)-3-iodo-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide (200 mg, 0.408 mmol, 1 equiv.), methyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (commercially available, CAS 844500-75-0, 113 mg, 0.408 mmol, 1 equiv.), cesium carbonate (265 mg, 0.816 mmol, 2 equiv.), 1,4-dioxane (10 mL), and water (2 mL). The reaction mixture was degassed with argon for 5 minutes, after which cataCXium (7.30 mg, 0.0204 mmol, 0.05 equiv) and Pd(OAc) (2.7 mg, 0.012 mmol, 0.03 equiv) were added. The reaction mixture was stirred at 80 °C for 30 minutes under microwave irradiation. After cooling to room temperature, the reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with water and then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to give methyl N-[4-[8-bromo-6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate as an off-white solid. 1 H NMR(400MHz,DMSO-d6)δ:9.91(s,1H),8.19(s,1H),7.74(s,1H),7.63(d,J=8.6Hz,2H),7 .53(d,J=1.2Hz,1H),7.34-7.44(m,4H),7.17(d,J=8.6Hz,2H),3.72(s,3H),3.37(s,3H).

[0298] Example 10: This example illustrates the preparation of methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-7-methoxy-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate (compound 39).

[0299] Step 1: Preparation of 5-iodo-4-methoxy-pyridin-2-amine [ka] To a stirred solution of 4-methoxypyridin-2-amine (1.00 g, 7.65 mmol, 1 equiv.) in dimethylformamide at room temperature was added N-iodosuccinimide (2.58 g, 11.5 mmol, 1.5 equiv.). The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with water, then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to afford 5-iodo-4-methoxy-pyridin-2-amine as an off-white solid. 1 H NMR(400MHz, CDCl3)δ:8.16(s,1H),5.98(s,1H),3.87(s,3H).

[0300] Step 2: Preparation of methyl 6-amino-4-methoxy-pyridine-3-carboxylate [ka] 5-Iodo-4-methoxy-pyridin-2-amine (1.00 g, 4.00 mmol, 1 equiv.), triethylamine (1.11 mL, 8.00 mmol, 2 equiv.), and methanol (20 mL) were placed in an autoclave. The reaction mixture was degassed with argon for 5 minutes. 1,1'-Bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (163 mg, 0.200 mmol, 0.05 equiv.) was then added, and the reaction mixture was degassed for another 5 minutes. The reaction mixture was then stirred at 100°C under CO gas (100 PSI) for 16 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The resulting residue was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with water and then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to give methyl 6-amino-4-methoxy-pyridine-3-carboxylate as an off-white solid. 1H NMR(400MHz,DMSO-d6)δ:8.33(s,1H),7.07(br s,2H),6.12(s,1H),3.81(s,3H),3.71(s,3H).

[0301] Step 3: Preparation of methyl 7-methoxyimidazo[1,2-a]pyridine-6-carboxylate [ka] Methyl 6-amino-4-methoxy-pyridine-3-carboxylate (100 mg, 0.521 mmol, 1 equiv.), water (5 mL), and bromoacetaldehyde dimethyl acetal (0.186 g, 1.04 mmol, 2 equiv.) were placed in a sealed tube. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was poured into pre-stirred cold saturated aqueous NaHCO3 solution and allowed to stir for 10 min. The reaction mixture was then diluted with dichloromethane. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography to afford methyl 7-methoxyimidazo[1,2-a]pyridine-6-carboxylate as a brown solid. 1 H NMR(400MHz,DMSO-d6)δ:9.12(s,1H),7.92-7.95(m,1H),7.61(d,J=1.2Hz, 1H),7.10(s,1H),3.90(s,3H),3.83(s,3H).

[0302] Step 4: Preparation of methyl 3-iodo-7-methoxy-imidazo[1,2-a]pyridine-6-carboxylate [ka] To a stirred solution of methyl 7-methoxyimidazo[1,2-a]pyridine-6-carboxylate (100 mg, 0.364 mmol, 1 equiv.) in dimethylformamide (0.5 mL) at room temperature was added N-iodosuccinimide (123 mg, 0.546 mmol, 1.2 equiv.). The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with water, then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to give methyl 3-iodo-7-methoxy-imidazo[1,2-a]pyridine-6-carboxylate. 1 H NMR(400MHz,DMSO-d6)δ:8.56(s,1H),7.64(s,1H),7.15(s,1H),3.89(s,3H),3.85(s,3H).

[0303] Step 5: Preparation of methyl 7-methoxy-3-[4-(methoxycarbonylamino)phenyl]imidazo[1,2-a]pyridine-6-carboxylic acid [ka] A microwave vial was charged with methyl 3-iodo-7-methoxy-imidazo[1,2-a]pyridine-6-carboxylate (400 mg, 1.14 mmol, 1 equiv.), methyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (commercially available, CAS 844500-75-0, 349 mg, 1.26 mmol, 1.1 equiv.), cesium carbonate (746 mg, 2.29 mmol, 2 equiv.), 1,4-dioxane (3 mL), and water (0.5 mL). The reaction mixture was degassed with argon for 5 minutes, after which cataCXium® A Pd G3 (43.9 mg, 0.0572 mmol, 0.05 equiv.) was added, which was then degassed for an additional 2 minutes. The reaction mixture was stirred at 95° C. for 1 hour under microwave irradiation. After cooling to room temperature, the reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with water and then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to give methyl 7-methoxy-3-[4-(methoxycarbonylamino)phenyl]imidazo[1,2-a]pyridine-6-carboxylate as an off-white solid. 1 H NMR(400MHz,DMSO-d6)δ:9.86(s,1H),8.71(s,1H),7.59-7.62(m,2H),7.61(s ,1H),7.53-7.58(m,2H),7.13(s,1H),3.90(s,3H),3.79(s,3H),3.70(s,3H).

[0304] Step 6: Preparation of 7-methoxy-3-[4-(methoxycarbonylamino)phenyl]imidazo[1,2-a]pyridine-6-carboxylic acid [ka] To a stirred solution of methyl 7-methoxy-3-[4-(methoxycarbonylamino)phenyl]imidazo[1,2-a]pyridine-6-carboxylate (150 mg, 0.401 mmol, 1 equiv.) in THF (10 mL) and methanol (5 mL) was added a solution of lithium hydroxide monohydrate (33.7 mg, 0.802 mmol, 2 equiv.) in water (5 mL) at room temperature. The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure. The resulting residue was diluted with water and neutralized with 2 M HCl. The resulting precipitate was filtered and dried under reduced pressure to give 7-methoxy-3-[4-(methoxycarbonylamino)phenyl]imidazo[1,2-a]pyridine-6-carboxylic acid as an off-white solid, which was used in the next step without further purification. 1 H NMR(400MHz,DMSO-d6)δ:9.86(s,1H),8.71(s,1H),7.61-7.66(m,2H),7.60(s,1H),7.53-7.58(m,2H),7.09(s,1H),3.89(s,3H),3.70(s,3H).

[0305] Step 7: Preparation of methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-7-methoxy-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate [ka] To a stirred solution of 7-methoxy-3-[4-(methoxycarbonylamino)phenyl]imidazo[1,2-a]pyridine-6-carboxylic acid (20.0 mg, 0.059 mmol, 1 equiv.) in pyridine (1 mL) was added 4-chloro-N-methyl-aniline (12.4 mg, 0.0879 mmol, 1.5 equiv.). Phosphorus(V) oxychloride (0.0268 mL, 0.293 mmol, 5 equiv.) was then added at 0° C. The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure. The resulting residue was diluted with water and neutralized with 2 M HCl. A precipitate formed, which was filtered and dried under reduced pressure. The crude residue was purified by flash chromatography to give methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-7-methoxy-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate. 1 H NMR(400MHz,DMSO-d6)δ:9.85(s,1H),8.41(s,1H),7.61-7.65(d,J=8.6Hz,2H),7.40-7.55(m,3H),7.22-7.41(m,3H),6.80-6.87(br s,1H),3.70(s,3H),3.67(br s,3H),3.33(br s,3H).

[0306] Example 11: This example illustrates the preparation of methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-8-cyanoimidazo[1,2-a]pyridin-3-yl]phenyl]carbamate (compound 40).

[0307] Step 1: Preparation of N-(4-chlorophenyl)-8-cyano-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide [ka] 8-Bromo-N-(4-chlorophenyl)-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide (described in Example 9, Step 2, 300 mg, 0.740 mmol, 1 equiv.), Zn(CN) (87.0 mg, 0.740 mmol, 1 equiv.), and dimethylformamide (2 mL) were placed in a sealed tube. The reaction mixture was degassed with nitrogen for 15 minutes, after which Xantphos (41.1 mg, 0.0740 mmol, 0.1 equiv.) and tris(dibenzylideneacetone)dipalladium(0) (67.8 mg, 0.0740 mmol, 0.1 equiv.) were added. The reaction mixture was heated to 140 °C and stirred for 16 hours. After cooling to room temperature, the reaction mixture was poured into ice water and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography to give N-(4-chlorophenyl)-8-cyano-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide. 1 H NMR(400MHz,DMSO-d6)δ:8.99(d,J=1.5Hz,1H),8.13(d,J=1.3Hz,1H),7.73(d,J=1. 5Hz,1H),7.70(d,J=1.3Hz,1H),7.38-7.41(m,2H),7.32-7.36(m,2H),3.40(s,3H).

[0308] Step 2: Preparation of N-(4-chlorophenyl)-8-cyano-3-iodo-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide [ka] To a stirred solution of N-(4-chlorophenyl)-8-cyano-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide (250 mg, 0.603 mmol, 1 equiv.) in dimethylformamide (0.5 mL) at room temperature was added N-iodosuccinimide (136 mg, 0.603 mmol, 1 equiv.). The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to afford N-(4-chlorophenyl)-8-cyano-3-iodo-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide as an off-white solid. 1 H NMR(400MHz,DMSO-d6)δ:8.44(s,1H)7.89(br s,1H),7.88(s,1H),7.40(s,4H),3.41(s,3H).

[0309] Step 3: Preparation of methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-8-cyano-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate [ka] A microwave vial was charged with N-(4-chlorophenyl)-8-cyano-3-iodo-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide (100 mg, 0.218 mmol, 1 equiv.), methyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (commercially available, CAS 844500-75-0, 66.3 mg, 0.239 mmol, 1.1 equiv.), cesium carbonate (142 mg, 0.435 mmol, 2 equiv.), 1,4-dioxane (3 mL), and water (0.5 mL). The reaction mixture was degassed with argon for 5 minutes, and then cataCXium® A Pd G3 (8.34 mg, 0.0109 mmol, 0.05 equiv.) was added. The reaction mixture was stirred at 95 °C for 1 hour under microwave irradiation. After cooling to room temperature, the reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with water and then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography to give methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-8-cyano-imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate as a yellow solid. 1 H NMR(400MHz,DMSO-d6)δ:9.93(s,1H),8.46(s,1H),7.90(d,J=1.3Hz,1H),7.84(s,1H),7 .64(d,J=8.8H...

Claims

1. Formula (I) 【Chemical 1】 wherein Z is O or S; R 1 is C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenyl, C 2-6 Alkynyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl, diC 1-6 Alkylaminocarbonyl-C 1-6 alkyl and CN, 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenyl, C 2-6 Alkynyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl and diC 1-6 Alkylaminocarbonyl-C 1-6 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxy, and CN; R 2a , R 2b and R 2c is H, hydroxy, halogen, CN, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 independently selected from alkyl; J is for CR 4 or N; G is CR 5 or N; If J is N, then G is CR 5 and when G is N, J is CR 4 and R 3 , R 4 and R 5 is H, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, halogen, CN, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 independently selected from alkylcarbonyl and hydroxy; 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen and CN; A is CH or N; and R 6 is C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, DiC 1-6 Alkylamino, C 1-6 Alkoxyamino and C 1-6 Alkyl C 1-6 alkoxyamino, each of said groups being optionally substituted with 1 to 3 substituents independently selected from halogen and CN. or a salt or N-oxide thereof.

2. A is N; and R 6 is C 1-4 Alkyl and C 1-4 2. The compound or salt of claim 1, wherein each of said groups is selected from alkoxy, each of said groups being optionally substituted with 1 to 3 substituents independently selected from halogen.

3. A is CH; and R 6 is C 1-4 Alkyl and C 1-4 2. The compound or salt of claim 1, wherein each of said groups is selected from alkoxy, each of said groups being optionally substituted with 1 to 3 substituents independently selected from halogen.

4. R 6 2. The compound or salt of claim 1, wherein is selected from methyl, ethyl and methoxy.

5. R 1 is C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 Alkyl and C 2-4 alkynyl, each of said groups being optionally substituted with 1 to 3 substituents independently selected from halogen and CN.

6. J is for CR 4 and G is CR 5 and R 3 , R 4 and R 5 is H, C 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, halogen, CN, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 independently selected from alkyl and hydroxy; 1-4 Alkyl, C 1-4 Alkoxy, C 1-4 Alkoxy-C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkoxy, C 2-4 Alkynyl, C 3-6 Cycloalkyl and C 3-6 Cycloalkyl-C 1-3 2. The compound or salt of claim 1, wherein each alkyl group is optionally substituted with 1 to 3 substituents independently selected from halogen.

7. J is for CR 4 and G is N; and R 3 and R 4 is H, C 1-4 Alkyl, C 1-4 Alkoxy, halogen, CN and C 2-4 2. The compound or salt of claim 1, wherein each of said groups is independently selected from alkynyl, each of said groups being optionally substituted with 1 to 3 substituents independently selected from halogen.

8. J is N and G is CR 5 and R 3 and R 5 is H, C 1-4 Alkyl, C 1-4 Alkoxy, halogen, CN and C 2-4 2. The compound or salt of claim 1, wherein each of said groups is independently selected from alkynyl, each of said groups being optionally substituted with 1 to 3 substituents independently selected from halogen.

9. A composition comprising a fungicidally effective amount of a compound according to any one of claims 1 to 8.

10. 10. The composition of claim 9, further comprising at least one compound selected from additional active ingredients, suitable formulation inactive ingredients, carriers, adjuvants, and any mixture thereof.

11. A method for eliminating, preventing or controlling plant pathogenic diseases, the method comprising applying to a plant pathogen, a habitat of a plant pathogen, or a plant or propagation material thereof susceptible to damage by a plant pathogen a fungicidally effective amount of a compound according to any one of claims 1 to 8 or a composition comprising a compound according to any one of claims 1 to 8.

12. Formula (XV) 【Chemistry 2】 wherein A is CH or N; R 6 is C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, DiC 1-6 Alkylamino, C 1-6 Alkoxyamino and C 1-6 Alkyl C 1-6 alkoxyamino, each of said groups being optionally substituted with 1 to 3 substituents independently selected from halogen and CN; and R 2a , R 2b and R 2c is H, hydroxy, halogen, CN, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 alkyl) or a compound of Formula (XVI) 【Chemistry 3】 wherein A is CH or N; R 6 is C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, DiC 1-6 Alkylamino, C 1-6 Alkoxyamino and C 1-6 Alkyl C 1-6 alkoxyamino, each of said groups being optionally substituted with 1 to 3 substituents independently selected from halogen and CN; R 8 is C 1 ~C 6 is alkyl; and R 2a , R 2b and R 2c is H, hydroxy, halogen, CN, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 alkyl) Compound.

13. Formula (XXI) 【Chemistry 4】 wherein A is CH or N; and R 2a , R 2b and R 2c is H, hydroxy, halogen, CN, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 alkyl) or a compound of Formula (XXII) 【Chemistry 5】 wherein A is CH or N; R 8 is C 1 ~C 6 is alkyl; and R 2a , R 2b and R 2c is H, hydroxy, halogen, CN, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 alkyl) Compound.

14. Formula (II) 【Chemistry 6】 (In the formula, R 1 is C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl, C 1-4 alkoxy and CN, 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl and C 1-4 Each of the alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogen and CN; R 2a , R 2b and R 2c is H, hydroxy, halogen, CN, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 independently selected from alkyl; J is for CR 4 or N; G is CR 5 or N; If J is N, then G is CR 5 and when G is N, J is CR 4 and R 3 and R 5 is H, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, halogen, CN, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 independently selected from alkylcarbonyl and hydroxy; 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen and CN; R 4 is H, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, halogen, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 alkylcarbonyl and hydroxy, 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen and CN; and X is Cl, Br or I. Compound.

15. Formula (XVII) 【Chemistry 7】 (In the formula, R 1 is C 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl, C 1-4 alkoxy and CN, 1-4 Alkyl, C 1-4 Alkoxy-C 1-4 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-3 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl and C 1-4 Each of the alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogen and CN; R 2a , R 2b and R 2c is H, hydroxy, halogen, CN, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 independently selected from alkyl; J is for CR 4 or N; G is CR 5 or N; If J is N, then G is CR 5 and when G is N, J is CR 4 and R 3 , R 4 and R 5 is H, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, halogen, CN, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 independently selected from alkylcarbonyl and hydroxy; 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen and CN. Compound.

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