Imidazo [1, 2-a] pyridine derivatives

Abstract

The present invention relates to: compounds of formula (I) wherein the substituents are as defined in claim 1; processes and methods for preparing a compound of formula (I); an agrochemical composition comprising a compound 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 materials by phytopathogenic microorganisms, in particular fungi.

Description

[0001] The present application relates to microbicidal imidazo[l,2-a]pyridine derivatives, e.g. as active ingredients, which have a microbicidal activity, in particular a fungicidal activity, more particularly an activity against Oomycetes. The present application also relates to the preparation of these imidazo[l,2-a]pyridine derivatives, to intermediates useful in the preparation of these imidazo[l,2-a]pyridine derivatives, to the preparation of these intermediates, to agrochemical compositions comprising at least one of these imidazo[l,2-a]pyridine derivatives, to the preparation of these compositions and to the use of these imidazo[l,2-a]pyridine derivatives or compositions in agriculture or horticulture for combating, controlling or preventing infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, in particular fungi, more particularly Oomycetes.

[0002] It has now surprisingly been found that certain new imidazo[l,2-a]pyridine derivatives have advantageous fungicidal properties, in particular against Oomycetes.

[0003] Thus, in a first aspect, the present application provides a compound of formula (I)

[0004]

[0005] wherein Z is O or S, and preferably Z is O;

[0006] A 1 is CH or N, and preferably is N;

[0007] R 1a , R 1b and R 1c are independently selected from hydrogen, hydroxyl, 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, C 2-4 alkenyl, and -NHC(O)C 1-6 alkyl;

[0008] A 2 is independently CR 2 or N, with the proviso that not more than four A 2 are N, preferably not more than three A 2 are N, preferably not more than two A2 If it is N, then no more than one A is preferred. 2 It is N, and more preferably five A's. 2 It is CR 2 ;

[0009] R 2 Independently selected from hydrogen, hydroxyl, halogen, CN, C 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 group, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl thioalkyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 Alkyl carbonyl, amino, C 1-6 Alkylamino, diC 1-6 -alkylamino, and C 3-6 cycloalkylamino, wherein the C 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 group, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl thioalkyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 alkyl carbonyl, C 1-6 alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 Alkyl carbonyl, amino, C 1-6 Alkylamino, diC 1-6 -alkylamino, and C3-6 each of the cycloalkyl groups is optionally substituted with one to three substituents independently selected from the group consisting of halogen, hydroxy, and CN;

[0010] R 4 selected from the group consisting of 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, wherein the 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, and diC 1-6 alkylaminocarbonyl-C 1-6 each of the alkyl groups is optionally substituted with one to three substituents independently selected from the group consisting of halogen and CN; and

[0011] R 5 selected from the group consisting of C 1-6 alkyl, C 1-6 alkoxy, C 3-6 cycloalkyl, C3-6 cycloalkyl-C 1-6 alkyl, C 1-6 alkoxy C 1-6 alkyl, C 1-6 alkylamino, di-C 1-6 alkylamino, C 1-6 alkoxyamino, and C 1-6 alkyl C 1-6 alkoxyamino, wherein each of the 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, di-C 1-6 alkylamino, C 1-6 alkoxyamino, and C 1-6 alkyl C 1-6 alkoxyamino, each of which is optionally substituted with one to three substituents independently selected from the group consisting of halogen and CN;

[0012] or salts or N-oxides thereof.

[0013] In a second aspect, the present application provides an agrochemical composition comprising a compound of formula (I), and more particularly an agrochemical composition comprising a fungicidally effective amount of a compound of formula (I). The composition can further comprise at least one compound selected from the group consisting of further active ingredients, suitable formulation inerts, carriers, adjuvants, and any mixture thereof.

[0014] The compounds of formula (I) can be used for controlling phytopathogenic microorganisms. Thus, for controlling phytopathogens, the compounds of formula (I) according to the application, or the compositions comprising the compounds of formula (I) can be applied to the phytopathogens, to the locus of the phytopathogens, in particular to the plants susceptible to infection by the phytopathogens, or to the plant propagation material.

[0015] Thus, in a third aspect, the present application 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 phytopathogens.

[0016] In a fourth aspect, the present application provides a method of combating, preventing or controlling phytopathogens, which comprises applying a compound of formula (I), or a composition comprising a compound of formula (I), as described herein to the phytopathogens, to the locus of the phytopathogens, in particular to the plants susceptible to infection by the phytopathogens, or to the plant propagation material.

[0017] The compounds of formula (I) are particularly effective against, preventing or controlling phytopathogenic fungi, in particular Oomycetes. Thus, in a fifth aspect, the present application provides the use of a compound of formula (I), or a composition comprising a compound of formula (I), as described herein, for controlling phytopathogenic fungi, in particular Oomycetes.

[0018] In a sixth aspect, the present application provides a method of combating, preventing or controlling a phytopathogenic disease, such as a phytopathogenic fungus, which comprises applying a compound of formula (I), or a composition comprising a compound of formula (I), as described herein, to said phytopathogenic fungus, or to the locus of said phytopathogenic fungus, in particular to a plant, or to propagation material of a plant, susceptible to attack by a phytopathogenic fungus, in particular Oomycetes.

[0019] Where groups are indicated as being substituted, for example, by alkyl, this includes those groups which are part of other groups, for example the alkyl group in alkylthio.

[0020] Definitions:

[0021] - the term "halogen" or "halo" means fluorine (fluoro or F), chlorine (chloro or CI), bromine (bromo or Br), or iodine (iodo or I), preferably fluorine, chlorine or bromine.

[0022] - the term "amino" means a -NH2 group.

[0023] - the term "alkyl" as used herein (alone or in combination with other terms), represents a straight-chain or branched-chain hydrocarbon, preferably having 1 to 6 carbon atoms, for example methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-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, i-propyl, n-butyl, i-butyl, s-butyl or t-butyl.

[0024] - the term "alkenyl" (alone or in combination with another term(s)) represents a straight-chain or branched-chain hydrocarbon, preferably having from 2 to 6 carbon atoms and at least one double bond, for example ethenyl, 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-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 from 2 to 4 carbon atoms are preferred, for example 2-propenyl, 2-butenyl or 1 -methyl-2-propenyl.

[0025] - the term "alkynyl" (alone or in combination with another term) represents a straight or branched chain hydrocarbon, preferably having from 2 to 6 carbon atoms and at least one triple bond, for example 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-hexadiynyl. Alkynyl groups having 2 to 4 carbon atoms are preferred, for example ethynyl, 2-propynyl or 2-butynyl-2-propenyl.

[0026] - the term "haloalkyl" refers to an alkyl group as generally defined above substituted by one or more of the same or different halogen atoms, for example fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, or 2,2,2-trifluoroethyl.

[0027] - the term "cyanoalkyl" refers to an alkyl group as generally defined above substituted by one or more cyano groups.

[0028] - the term "cycloalkyl" (alone or in combination with another term) represents a saturated or partially unsaturated monocyclic, bicyclic or tricyclic hydrocarbon, preferably having from 3 to 10 carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl or adamantyl. Cycloalkyl groups having 3, 4, 5, 6 or 7 carbon atoms are preferred, for example cyclopropyl or cyclobutyl.

[0029] - the term "halocycloalkyl" refers to a cycloalkyl ring as defined above substituted by one or more of the same or different halogen atoms.

[0030] - the term "cyanocycloalkyl" refers to a cycloalkyl group as generally defined above substituted by one or more cyano groups.

[0031] - the term "alkoxy" refers to a group of the formula -OR a a ​is alkyl as generally defined above. Examples of alkoxy groups include, but are not limited to, methoxy, ethoxy, propyloxy, isopropoxy, and tert-butoxy. The term "alkoxyalkyl" refers to an alkyl group (as mentioned above) which is substituted with said alkoxy group. Examples are methoxymethyl, methoxyethyl, ethoxymethyl and propoxymethyl.

[0032] The term "alkylsulfanyl" refers to a group of formula -SR a wherein R a is alkyl as generally defined above.

[0033] The term "alkylsulfinyl" refers to a group of formula -S(O)R a wherein R a is alkyl as generally defined above.

[0034] The term "alkylsulfonyl" refers to a group of formula -S(O)2R a wherein R a is alkyl as generally defined above.

[0035] The term "alkylcarbonyl" refers to a group of formula R a C(O)- wherein R a is alkyl as generally defined above.

[0036] The term "alkoxycarbonyl" refers to a group of formula R a OC(O)- wherein R a is alkyl as generally defined above.

[0037] The term "alkylamino" refers to a group of formula R a NH- wherein R a is alkyl as generally defined above.

[0038] The term "cycloalkylamino" refers to a group of formula R a NH- wherein R a is cycloalkyl as generally defined above.

[0039] The term "alkoxyamino" refers to a group of formula R a NH- wherein R a is alkoxy as generally defined above.

[0040] The term "alkylaminocarbonyl" refers to a group of formula R a NHC(O)- wherein R a is alkyl as generally defined above.

[0041] Hydroxyl ("hydroxyl" or "hydroxy") represents an -OH group.

[0042] In the context of the present application, the terms "combating", "preventing" or "controlling" and their derivatives mean reducing any undesired influence, for example pathogenic, more particularly phytopathogenic, especially fungal such as Oomycetes, infestation or attack of plants or plant-derived products and pathogenic damage to a level which shows an improvement.

[0043] As used herein, the term "effective amount" means the amount of a compound, salt or N-oxide thereof, which at single or multiple administrations provides the desired effect.

[0044] An effective amount is readily determined by one of skill in the art by using known techniques and by observing results obtained under analogous circumstances. In determining the effective amount, a number of factors are considered, including but not limited to: the type of plant or derived product to be applied; the pathogen to be controlled and its life cycle; the particular compound applied; the type of application; and other relevant circumstances.

[0045] A compound of formula (I) having at least one basic center can form, for example, acid addition salts with strong inorganic acids, such as mineral acids, for example, hydrochloric acid, sulfuric acid, nitric acid, nitrous acid, phosphoric acid or a hydrohalic acid, with strong organic carboxylic acids, such as C 1-4 alkanecarboxylic acids, for example, acetic acid, such as saturated or unsaturated dicarboxylic acids, for example, oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, such as hydroxycarboxylic acids, for example, ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or such as benzoic acids, or organic sulfonic acids, such as C 1-4 alkanesulfonic acids or arylsulfonic acids, for example, methane sulfonic acid or p-toluene sulfonic acid). A compound of formula (I) having at least one acidic group can form salts, for example, with bases, for example, mineral salts, such as alkali metal or alkaline earth metal salts, for example, sodium salts, potassium salts or magnesium salts, or salts with ammonia or organic amines, such as morpholine, piperidine, pyrrolidine, mono-, di- or tri-lower alkylamines, for example, ethylamine, diethylamine, triethylamine or dimethylpropylamine, or mono-, di- or tri-hydroxy lower alkylamines, for example, mono-, di- or tri-ethanolamine.

[0046] In each case, the compound having formula (I) according to the invention is in a free form, an oxidized form (as an N-oxide), a covalently hydrated form, or a salt form (e.g., an agronomically usable or agrochemically acceptable salt form). The N-oxide is an oxidized form of a tertiary amine or an oxidized form of a nitrogen-containing heteroaromatic compound. For example, they are described in the book entitled "Heterocyclic N-oxides" published by A. Albini and S. Pietra in 1991 by CRC Press in Boca Raton. The compound having formula (I) according to the invention also includes hydrates that can be formed during salt formation.

[0047] The compounds of formula (I) according to the present invention also include hydrates that may form during salt formation.

[0048] In another embodiment, a compound of formula (I) according to the invention is provided, wherein R 1a R 1b and R 1c Independently selected from hydrogen and 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 2-4 alkenyl and C 1-6 Alkyl group.

[0049] In a particular embodiment, R 1a R 1b and R 1c It can be independently selected from hydrogen and C. 2-4 alkenyl and C 1-6 alkyl.

[0050] In another specific embodiment, R 1a and R 1c It can be hydrogen; and R 1b It can be selected from hydrogen, hydroxyl, 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 Alkoxy, amino, C 2-4 alkenyl and NHC(O)C 1-6 Alkyl, and more preferably R 1b It can be selected from hydrogen, C 1-6 Alkyl, C 3-6cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl and C 2-4 Alkenyl group.

[0051] In another embodiment, a compound of formula (I) according to the invention is provided, wherein R 2 Independently selected from hydrogen, hydroxyl, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 alkylaminocarbonyl, and C 1-6 alkyl carbonyl, wherein the C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 alkylaminocarbonyl, and C 1-6 Each of the alkyl carbonyl groups may optionally be substituted by one to three independent substituents selected from the following: halogen, hydroxyl, and CN; preferably R. 2 Independently selected from hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 alkoxy carbonyl and C 1-6 Alkoxy-C 1-6 alkoxy group, wherein the C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 alkoxy carbonyl and C 1-6 Alkoxy-C 1-6 Each of the alkoxy groups may optionally be substituted by one to three independent substituents selected from the following: halogen, hydroxyl, and CN; and more preferably R 2 Independently selected from hydrogen, halogen, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6Alkoxycarbonyl and CN.

[0052] In another embodiment, a compound of formula (I) according to the invention is provided, wherein four A 2 It is CR 4 And an A 2 It is N.

[0053] In another embodiment, a compound having formula (I) according to the invention is provided, wherein

[0054] yes And preferably four A's 2 It is CR 2 .

[0055] In another embodiment, a compound having formula (I) according to the invention is provided, wherein

[0056] yes And preferably four A's 2 It is CR 2 .

[0057] In another embodiment, a compound of formula (I) according to the invention is provided, wherein five A 2 It is CR 2 And preferably yes

[0058] In it yes In a specific embodiment, R 2 It is as defined in this invention; preferably R 2 Independently selected from hydrogen, hydroxyl, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 alkylaminocarbonyl, and C 1-6 alkyl carbonyl, wherein the C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC1-6 alkylcarbonyl, and C 1-6 each of the alkylcarbonyl groups is optionally substituted with one to three substituents independently selected from the group consisting of halogen, hydroxy, and CN; preferably R 2 is independently selected from the group consisting of hydrogen, halogen, CN, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkoxycarbonyl, and C 1-6 alkoxy-C 1-6 alkoxy, wherein the C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkoxycarbonyl, and C 1-6 alkoxy-C 1-6 each of the alkyl groups is optionally substituted with one to three substituents independently selected from the group consisting of halogen, hydroxy, and CN; and more preferably R 2 is independently selected from the group consisting of hydrogen, halogen, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkoxycarbonyl, and CN.

[0059] In another embodiment, there is provided a compound according to the application of Formula (I), wherein R 4 is selected from C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 alkyl, and C 1-6 alkoxy, wherein the C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 alkyl, and C 1-6 each of the alkyl groups is optionally substituted with one to three substituents independently selected from the group consisting of halogen and CN.

[0060] In another embodiment, there is provided a compound according to the application of Formula (I), wherein R 5 is selected from C 1-6 alkyl, C 1-6 alkoxy, C 3-6cycloalkyl, C 3-6 cycloalkyl-C 1-6 alkyl, and C 1-6 alkoxy C 1-6 alkyl, wherein each of said radicals is optionally substituted with one to three substituents independently selected from the group consisting of halogen and CN.

[0061] In particular embodiments, compounds of formula (I) according to the present application are provided, wherein

[0062] Z is O;

[0063] A 1 is CH or N, more preferably N;

[0064] R 1a , R 1b and R 1c are independently selected from the group consisting of hydrogen, hydroxyl, 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 alkoxy, amino, C 2-4 alkenyl, and NHC(O)C 1-6 alkyl, and preferably R 1a , R 1b and R 1c are independently selected from the group consisting of hydrogen, C 2-4 alkenyl, and C 1-6 alkyl;

[0065] five A 2 are CR 2 , wherein R 2 is independently selected from the group consisting of hydrogen, hydroxyl, halogen, CN, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl, and C 1-6 alkoxy-C 1-6 alkoxy, C 1-6 alkoxycarbonyl, C 1-6 alkylaminocarbonyl, diC 1-6 alkylaminocarbonyl, and C 1-6 alkylcarbonyl, wherein the C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkoxy, C 1-6alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 alkylaminocarbonyl, and C 1-6 Each of the alkyl carbonyl groups may optionally be substituted by one to three independent substituents selected from the following: halogen, hydroxyl, and CN; preferably R. 2 Independently selected from hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 alkoxy carbonyl and C 1-6 Alkoxy-C 1-6 alkoxy group, wherein the C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 alkoxy carbonyl and C 1-6 Alkoxy-C 1-6 Each of the alkoxy groups may optionally be substituted by one to three independent substituents selected from the following: halogen, hydroxyl, and CN; and more preferably R 2 Independently selected from hydrogen, halogen, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl groups and CN;

[0066] R 4 Selected from C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 Alkyl and C 1-6 alkoxy group, wherein the C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 Alkyl and C 1-6 Each of the alkoxy groups may optionally be substituted by one to three independent substituents selected from the following: halogens and CN; and

[0067] R 5 Selected from C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 Alkyl and C1-6 alkoxy C 1-6 alkyl, wherein each of said radicals is optionally substituted with one to three substituents independently selected from the group consisting of halogen and CN.

[0068] In preferred embodiments, is R 2 is as defined in the present invention; preferably R 2 is independently selected from the group consisting of hydrogen, hydroxyl, halogen, CN, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl, and C 1-6 alkoxy-C 1-6 alkoxy, C 1-6 alkoxycarbonyl, C 1-6 alkylaminocarbonyl, di-C 1-6 alkylaminocarbonyl, and C 1-6 alkylcarbonyl, wherein the C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkoxy, C 1-6 alkoxycarbonyl, C 1-6 alkylaminocarbonyl, di-C 1-6 alkylaminocarbonyl, and C 1-6 alkylcarbonyl, each of which is optionally substituted with one to three substituents independently selected from the group consisting of halogen, hydroxyl, and CN; preferably R 2 is independently selected from the group consisting of hydrogen, halogen, CN, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkoxycarbonyl, and C 1-6 alkoxy-C 1-6 alkoxy, wherein the C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkoxycarbonyl, and C 1-6 alkoxy-C 1-6 alkoxy, each of which is optionally substituted with one to three substituents independently selected from the group consisting of halogen, hydroxyl, and CN; and more preferably R 2 is independently selected from the group consisting of hydrogen, halogen, C 1-6 alkyl, C 1-6 alkoxy, C1-6 alkoxy-C 1-6 alkyl, C 1-6 alkoxycarbonyl, and CN.

[0069] In another embodiment, the compound according to the application is selected from:

[0070] N-[5-[6-[(4-cyano-3-methoxy-benzoyl)-methyl-amino]-8-methyl- imidazo [ 1,2-a] pyridin-3 -yl] -2-pyridinyl] -carbamic acid methyl ester ;

[0071] N-[5-[6-[(4-cyano-3-methoxy-benzoyl)-methyl-amino]-8-methyl- imidazo [ 1,2-a] pyridin-3 -yl] -2-pyridinyl] -carbamic acid methyl ester ;

[0072] N-[5-[6-[(2-methoxypyridine-4-carbonyl)-methyl-amino]-8-methyl- imidazo [ 1,2-a] pyridin-3 -yl] -2-pyridinyl] -carbamic acid methyl ester ;

[0073] N-[5-[6-[(4-cyano-3-methoxy-benzoyl)-methyl-amino]-8-methyl- imidazo [ 1,2-a] pyridin-3 -yl] -2-pyridinyl] -carbamic acid methyl ester ;

[0074] N-[5-[6-[(4-cyano-3-methoxy-benzoyl)-methyl-amino]-8-methyl- imidazo [ 1,2-a] pyridin-3 -yl] -2-pyridinyl] -carbamic acid methyl ester ;

[0075] N-[5-[6-[cyano-methyl-(4-fluorobenzoyl)amino]imidazo[ 1,2-a]pyridin-3-yl]- 2-pyridinyl] -carbamic acid methyl ester ;

[0076] N-[5-[6-[cyano-methyl-(4-fluoro-3-methoxy-benzoyl)amino]imidazo[ 1,2- a]pyridin-3-yl]-2-pyridinyl] -carbamic acid methyl ester ;

[0077] N-[5-[6-[(2-methoxypyridine-4-carbonyl)-methyl-amino]imidazo[ 1,2- a]pyridin-3-yl]-2-pyridinyl] -carbamic acid methyl ester ;

[0078] N-[5-[6-[(4-cyano-3-methoxy-benzoyl)-methyl-amino]-8-methyl- imidazo [ 1,2-a] pyridin-3 -yl] -2-pyridinyl] -carbamic acid methyl ester ;

[0079] N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2- a]pyridin-3-yl]-2-pyridinyl] -carbamic acid methyl ester;

[0080] N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2- a]pyridin-3-yl]-2-pyridinyl] -carbamic acid methyl ester;

[0081] N-[5-[6-[(3,4-difluorobenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridin-3- yl] -2-pyridinyl] -carbamic acid methyl ester;

[0082] N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2- a]pyridin-3-yl]-2-pyridinyl] -carbamic acid methyl ester;

[0083] N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2- a]pyridin-3-yl]-2-pyridinyl] -carbamic acid methyl ester;

[0084] N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2- a]pyridin-3-yl]-2-pyridinyl] -carbamic acid methyl ester;

[0085] N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2- a]pyridin-3-yl]-2-pyridinyl] -carbamic acid methyl ester;

[0086] N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2- a]pyridin-3-yl]-2-pyridinyl] -carbamic acid methyl ester;

[0087] N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2- a]pyridin-3-yl]-2-pyridinyl] -carbamic acid methyl ester;

[0088] N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2- a]pyridin-3-yl]-2-pyridinyl] -carbamic acid methyl ester;

[0089] N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2- a]pyridin-3-yl]-2-pyridinyl] -carbamic acid methyl ester;

[0090] N-[5-[6-[(4-fluoro-3-methyl-benzoyl)-methyl-amino]imidazo[l,2-a]pyridin-3-yl]-2- pyridinyl]carbamic acid methyl ester;

[0091] N-[5-[6-[(3,4-difluorobenzoyl)-methyl-amino]imidazo[l,2-a]pyridin-3-yl]-2- pyridinyl]carbamic acid methyl ester;

[0092] N-[5-[6-[(3-ethoxy-4-fluoro-benzoyl)-methyl-amino]imidazo[l,2-a]pyridin-3-yl]-2- pyridinyl]carbamic acid methyl ester;

[0093] N-[5-[6-[(4-fluorobenzoyl)-(methoxymethyl)amino]imidazo[l,2-a]pyridin-3-yl]-2- pyridinyl]carbamic acid methyl ester;

[0094] N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-(methoxymethyl)amino]imidazo[l,2-a]pyridin-3- yl]-2-pyridinyl]carbamic acid methyl ester;

[0095] N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]imidazo[l,2-a]pyridin-3-yl]-2- pyridinyl]carbamic acid methyl ester;

[0096] N-[4-[6-[(4-chlorobenzoyl)-methyl-amino]imidazo[l,2-a]pyridin-3-yl]phenyl]carbamic acid methyl ester;

[0097] N-[3-[6-(ethylcarbamoylamino)-3-pyridinyl]-8-methyl-imidazo[l,2-a]pyridin-6-yl]-4- fluoro-3-methoxy-N-methyl-benzamide;

[0098] N-[3-[4-(cyclopropanecarbonylamino)phenyl]-8-methyl-imidazo[l,2-a]pyridin-6-yl]-4- fluoro-3-methoxy-N-methyl-benzamide;

[0099] 4-fluoro-3-methoxy-N-[3-[4-[(2-methoxyacetyl)amino]phenyl]-8-methyl-imidazo[l,2- a]pyridin-6-yl]-N-methyl-benzamide;

[0100] N-[4-[6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]-8-methyl-imidazo[l,2-a]pyridin- 3-yl]-phenyl]carbamic acid methyl ester;

[0101] N-[3-(4-acetylamino-phenyl)-8-methyl-imidazo[l,2-a]pyridin-6-yl]-4-fluoro-3-methoxy-N-methyl-benzamide;

[0102] N-[3-(6-acetylamino-3-pyridyl)-8-methyl-imidazo[l,2-a]pyridin-6-yl]-4-fluoro-3-methoxy-N-methyl-benzamide;

[0103] 4-[[3-[6-(methoxycarbonylamino)-3-pyridyl]-8-methyl-imidazo[l,2-a]pyridin-6-yl]- methyl-carbamoyl]-2-methyl-benzoic acid methyl ester;

[0104] 5-Fluoro-2-[[3-[6-(methoxycarbonylamino)-3-pyridyl]-8-methyl-imidazo[l,2-a]pyridin-6-yl]- methyl-carbamoyl]benzoic acid methyl ester;

[0105] 5-[[3-[6-(methoxycarbonylamino)-3-pyridyl]-8-methyl-imidazo[l,2-a]pyridin-6-yl]- methyl-carbamoyl]pyridine-2-carboxylic acid methyl ester;

[0106] N-[5-[6-[(6-methoxypyridine-2-carbonyl)-methyl-amino]-8-methyl-imidazo[l,2-a]pyridin-3-yl]- 2-pyridyl]carbamic acid methyl ester;

[0107] N-[5-[6-[(5-methoxypyridine-2-carbonyl)-methyl-amino]-8-methyl-imidazo[l,2-a]pyridin-3-yl]- 2-pyridyl]carbamic acid methyl ester;

[0108] N-[5-[6-[(2-fluoro-4-methoxy-benzoyl)-methyl-amino]-8-methyl-imidazo[l,2-a]pyridin-3-yl]- 2-pyridyl]carbamic acid methyl ester;

[0109] 2-[[3-[6-(methoxycarbonylamino)-3-pyridyl]-8-methyl-imidazo[l,2-a]pyridin-6-yl]- methyl-carbamoyl]benzoic acid methyl ester;

[0110] N-[5-[6-[(4-chloro-3-methyl-benzoyl)-methyl-amino]-8-methyl-imidazo[l,2-a]pyridin-3-yl]- 2-pyridyl]carbamic acid methyl ester;

[0111] N-[5-[6-[(5-cyano-4-methyl-pyridine-2-carbonyl)-methyl-amino]-8-methyl-imidazo[l,2-a]pyridin- 3-yl]-2-pyridyl]carbamic acid methyl ester;

[0112] N-[5-[6-[(6-fluoro-5-methyl-pyridin-3-carbonyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate;

[0113] N-[5-[6-[(6-methoxypyridin-3-carbonyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate;

[0114] N-[5-[6-[(4-fluorobenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]carbamate;

[0115] N-[5-[8-methyl-6-[methyl-(2-methylthioalkylpyridin-3-carbonyl)amino]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate;

[0116] N-[5-[6-[(4-cyanobenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]carbamate;

[0117] N-[5-[6-[(3-fluoro-4-methyl-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]carbamate;

[0118] N-[5-[6-[(4-chlorobenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]carbamate;

[0119] N-[5-[6-[(3-chloro-4-cyanobenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]carbamate;

[0120] N-[5-[6-[(6-cyanopyridin-3-carbonyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate;

[0121] N-[5-[6-[(5-cyano-2-methyl-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]carbamate;

[0122] N-[5-[6-[(3-methoxybenzoyl)-methyl-amino]-8-methyl-imidazo[l,2- a]pyridin-3-yl]-2-pyridyl]methy lam ino acetate;

[0123] N-[5-[6-[(2,4-difluorobenzoyl)-methyl-amino]-8-methyl-imidazo[l,2- a]pyridin-3-yl]-2-pyridyl]methy lam ino acetate;

[0124] N-[5-[8-cyano-6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]imidazo[l,2- a]pyridin-3-yl]-2-pyridyl]methy lam ino acetate;

[0125] N-[5-[8-cyclopropyl-6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]imidazo[l,2- a]pyridin-3-yl]-2-pyridyl]methy lam ino acetate;

[0126] N-[5-[8-ethyl-6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]imidazo[l,2- a]pyridin-3-yl]-2-pyridyl]methy lam ino acetate;

[0127] N-[5-[8-but-3-enyl-6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]imidazo[l,2- a]pyridin-3-yl]-2-pyridyl]methy lam ino acetate;

[0128] N-[5-[8-acetamido-6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]imidazo[l,2- a]pyridin-3-yl]-2-pyridyl]methy lam ino acetate;

[0129] N-[5-[8-bromo-6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]imidazo[l,2- a]pyridin-3-yl]-2-pyridyl]methy lam ino acetate;

[0130] N-[5-[6-[2-cyanoethyl-(4-fluorobenzoyl)amino]imidazo[l,2-a]pyridin-3-yl]-2- pyridyl]methy lam ino acetate; and

[0131] N-[5-[6-[2-cyanoethyl-(4-fluoro-3-methoxy-benzoyl)amino]imidazo[l,2- a]pyridin-3-yl]-2-pyridyl]methy lam ino acetate.

[0132] The method according to the application has the advantageous property of protecting plants from pathogenic, such as phytopathogenic, especially fungal, for example oomycetes, attack or infestation, which leads to diseases and damage to the plants; in particular in the case of plants, the present application can control, limit or prevent pathogenic damage to the plants, plant parts, plant propagation material and / or growing plants.

[0133] The compounds in the following Tables 1.1 to 1.144 below show specific compounds of the present application.

[0134] Table 1.1 660 compounds of the formula (Ia) E1.1 to E1.660 are provided

[0135]

[0136] wherein R 1b is H, A 1 is CH, A 2a is N and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0137] Table Z: R 2 , A 2b , R 4 and R 5 are defined as substituents

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169] Table 1.2 660 compounds of formula (Ia) E2.1 to E2.660 are provided, wherein R 1b is H, A 1 is CH, A 2a is CH and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0170] Table 1.3660 compounds of formula (Ia) E3.1 to E3.660 are provided, wherein R 1b is H, A 1 is CH, A 2a is CF and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0171] Table 1.4 660 compounds of formula (Ia) E4.1 to E4.660 are provided, wherein R 1b is H, A 1 is CH, A 2a is CCI and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0172] Table 1.5 660 compounds of formula (Ia) E5.1 to E5.660 are provided, wherein R 1b is H, A 1 is CH, A 2a is CBr and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0173] Table 1.6 660 compounds of formula (Ia) E6.1 to E6.660 are provided, wherein R 1b is H, A 1 is CH, A 2a is CCH3 and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0174] Table 1.7 660 compounds of formula (Ia) E7.1 to E7.660 are provided, wherein R 1b is H, A 1 is CH, A 2a is CCH2CH3 and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0175] Table 1.8660 compounds of formula (Ia) E8.1 to E8.660 are provided, wherein R 1b is H, A 1 is CH, A 2a is CCN and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0176] Table 1.9 660 compounds of formula (Ia) E9.1 to E9.660 are provided, wherein R 1b is H, A 1 is CH, A 2a is COCH3 and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0177] Table 1.10 660 compounds of formula (Ia) E10.1 to E10.660 are provided, wherein R 1b is H, A 1 is N, A 2a is N and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0178] Table 1.11 660 compounds of formula (Ia) E11.1 to E11.660 are provided, wherein R 1b is H, A 1 is N, A 2a is CH and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0179] Table 1.12 660 compounds of formula (Ia) E12.1 to E12.660 are provided, wherein R 1b is H, A 1 is N, A 2a is CF and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0180] Table 1.13660 compounds of formula (Ia) E13.1 to E13.660 are provided, wherein R 1b is H, A 1 is N, A 2a is CC1 and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0181] Table 1.14 660 compounds of formula (Ia) E14.1 to E14.660 are provided, wherein R 1b is H, A 1 is N, A 2a is CBr and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0182] Table 1.15 660 compounds of formula (Ia) E15.1 to E15.660 are provided, wherein R 1b is H, A 1 is N, A 2a is CCH3 and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0183] Table 1.16 660 compounds of formula (Ia) E16.1 to E16.660 are provided, wherein R 1b is H, A 1 is N, A 2a is CCH2CH3 and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0184] Table 1.17 660 compounds of formula (Ia) E17.1 to E17.660 are provided, wherein R 1b is H, A 1 is N, A 2a is CCN and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0185] Table 1.18660 compounds of formula (Ia) E18.1 to E18.660 are provided, wherein R 1b is H, A 1 is N, A 2a is COCH3and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0186] Table 1.19 660 compounds of formula (Ia) E19.1 to E19.660 are provided, wherein R 1b is CH3, A 1 is CH, A 2a is N and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0187] Table 1.20 660 compounds of formula (Ia) E20.1 to E20.660 are provided, wherein R 1b is CH3, A 1 is CH, A 2a is CH and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0188] Table 1.21 660 compounds of formula (Ia) E21.1 to E21.660 are provided, wherein R 1b is CH3, A 1 is CH, A 2a is CF and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0189] Table 1.22 660 compounds of formula (Ia) E22.1 to E22.660 are provided, wherein R 1b is CH3, A 1 is CH, A 2a is CCl and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0190] Table 1.23660 compounds of formula (Ia) E23.1 to E23.660 are provided, wherein R 1b is CH3, A 1 is CH, A 2a is CBr and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0191] Table 1.24 660 compounds of formula (Ia) E24.1 to E24.660 are provided, wherein R 1b is CH3, A 1 is CH, A 2a is CCH3 and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0192] Table 1.25 660 compounds of formula (Ia) E25.1 to E25.660 are provided, wherein R 1b is CH3, A 1 is CH, A 2a is CCH2CH3 and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0193] Table 1.26 660 compounds of formula (Ia) E26.1 to E26.660 are provided, wherein R 1b is CH3, A 1 is CH, A 2a is CCN and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0194] Table 1.27 660 compounds of formula (Ia) E27.1 to E27.660 are provided, wherein R 1b is CH3, A 1 is CH, A 2a is COCH3 and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0195] Table 1.28660 compounds of formula (Ia) E28.1 to E28.660 are provided wherein R 1b is CH3, A 1 is N, A 2a is N and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0196] Table 1.29 660 compounds of formula (Ia) E29.1 to E29.660 are provided wherein R 1b is CH3, A 1 is N, A 2a is CH and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0197] Table 1.30 660 compounds of formula (Ia) E30.1 to E30.660 are provided wherein R 1b is CH3, A 1 is N, A 2a is CF and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0198] Table 1.31 660 compounds of formula (Ia) E31.1 to E31.660 are provided wherein R 1b is CH3, A 1 is N, A 2a is CCI and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0199] Table 1.32 660 compounds of formula (Ia) E32.1 to E32.660 are provided wherein R 1b is CH3, A 1 is N, A 2a is CBr and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0200] Table 1.33660 compounds having formula (Ia) from E33.1 to E33.660 are provided, wherein R 1b It is CH3, A 1 It is N, A 2a It is CCH3 and R 2 A 2b R 4 R 5 It is as defined in Table Z.

[0201] Table 1.34 660 compounds having formula (Ia) from E34.1 to E34.660 are provided, wherein R 1b It is CH3, A 1 It is N, A 2a It is CCH2CH3 and R 2 A 2b R 4 R 5 It is as defined in Table Z.

[0202] Table 1.35 660 compounds having formula (Ia) from E35.1 to E35.660 are provided, wherein R 1b It is CH3, A 1 It is N, A 2a It is CCN and R 2 A 2b R 4 R 5 It is as defined in Table Z.

[0203] Table 1.36 660 compounds having formula (Ia) from E36.1 to E36.660 are provided, wherein R 1b It is CH3, A 1 It is N, A 2a It is COCH3 and R 2 A 2b R 4 R 5 It is as defined in Table Z.

[0204] Table 1.37 660 compounds having formula (Ia) from E37.1 to E37.660 are provided, wherein R 1b It is CH2CH3, A 1 It is CH, A 2a It is N and R 2 A 2b R 4 R 5 It is as defined in Table Z.

[0205] Table 1.38660 compounds of formula (Ia) E38.1 - E38.660 are provided, wherein R 1b is CH2CH3, A 1 is CH, A 2a is CH and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0206] Table 1.39 660 compounds of formula (Ia) E39.1 - E39.660 are provided, wherein R 1b is CH2CH3, A 1 is CH, A 2a is CF and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0207] Table 1.40 660 compounds of formula (Ia) E40.1 - E40.660 are provided, wherein R 1b is CH2CH3, A 1 is CH, A 2a is CCI and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0208] Table 1.41 660 compounds of formula (Ia) E41.1 - E41.660 are provided, wherein R 1b is CH2CH3, A 1 is CH, A 2a is CBr and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0209] Table 1.42 660 compounds of formula (Ia) E42.1 - E42.660 are provided, wherein R 1b is CH2CH3, A 1 is CH, A 2a is CCH3 and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0210] Table 1.43 660 compounds of formula (Ia) E43.1 - E43.660 are provided, wherein R 1b is CH2CH3, A 1 is CH, A 2a is CCH2CH3 and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0211] Table 1.44 660 compounds of formula (Ia) E44.1 - E44.660 are provided, wherein R 1b is CH2CH3, A 1 is CH, A 2a is CCN and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0212] Table 1.45 660 compounds of formula (Ia) E45.1 - E45.660 are provided, wherein R 1b is CH2CH3, A 1 is CH, A 2a is COCH3 and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0213] Table 1.46 660 compounds of formula (Ia) E46.1 - E46.660 are provided, wherein R 1b is CH2CH3, A 1 is N, A 2a is N and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0214] Table 1.47 660 compounds of formula (Ia) E47.1 - E47.660 are provided, wherein R 1b is CH2CH3, A 1 is N, A 2a is CH and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0215] Table 1.48 660 compounds of formula (Ia) E48.1 to E48.660 are provided, wherein R 1b is CH2CH3, A 1 is N, A 2a is CF and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0216] Table 1.49 660 compounds of formula (Ia) E49.1 to E49.660 are provided, wherein R 1b is CH2CH3, A 1 is N, A 2a is CCI and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0217] Table 1.50 660 compounds of formula (Ia) E50.1 to E50.660 are provided, wherein R 1b is CH2CH3, A 1 is N, A 2a is CBr and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0218] Table 1.51 660 compounds of formula (Ia) E51.1 to E51.660 are provided, wherein R 1b is CH2CH3, A 1 is N, A 2a is CCH3 and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0219] Table 1.52 660 compounds of formula (Ia) E52.1 to E52.660 are provided, wherein R 1b is CH2CH3, A 1 is N, A 2a is CCH2CH3 and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0220] Table 1.53 660 compounds E53.1 to E53.660 of formula (Ia) are provided, wherein R 1b is CH2CH3, A 1 is N, A 2a is CCN and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0221] Table 1.54 660 compounds E54.1 to E54.660 of formula (Ia) are provided, wherein R 1b is CH2CH3, A 1 is N, A 2a is COCH3 and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0222] Table 1.55 660 compounds E55.1 to E55.660 of formula (Ia) are provided, wherein R 1b is CH2OCH3, A 1 is CH, A 2a is N and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0223] Table 1.56 660 compounds E56.1 to E56.660 of formula (Ia) are provided, wherein R 1b is CH2OCH3, A 1 is CH, A 2a is CH and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0224] Table 1.57 660 compounds E57.1 to E57.660 of formula (Ia) are provided, wherein R 1b is CH2OCH3, A 1 is CH, A 2a is CF and R 2 , A 2b , R 4 , R 5is as defined in Table Z.

[0225] Table 1.58 660 compounds of formula (Ia) E58.1 to E58.660 are provided, wherein R 1b is CH2OCH3, A 1 is CH, A 2a is CCI and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0226] Table 1.59 660 compounds of formula (Ia) E59.1 to E59.660 are provided, wherein R 1b is CH2OCH3, A 1 is CH, A 2a is CBr and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0227] Table 1.60 660 compounds of formula (Ia) E60.1 to E60.660 are provided, wherein R 1b is CH2OCH3, A 1 is CH, A 2a is CCH3 and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0228] Table 1.61 660 compounds of formula (Ia) E61.1 to E61.660 are provided, wherein R 1b is CH2OCH3, A 1 is CH, A 2a is CCH2CH3 and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0229] Table 1.62 660 compounds of formula (Ia) E62.1 to E62.660 are provided, wherein R 1b is CH2OCH3, A 1 is CH, A 2a is CCN and R 2 , A 2b , R4 , R 5 is as defined in Table Z.

[0230] Table 1.63 660 compounds of formula (Ia) E63.1 to E63.660 are provided, wherein R 1b is CH2OCH3, A 1 is CH, A 2a is COCH3 and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0231] Table 1.64 660 compounds of formula (Ia) E64.1 to E64.660 are provided, wherein R 1b is CH2OCH3, A 1 is N, A 2a is N and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0232] Table 1.65 660 compounds of formula (Ia) E65.1 to E65.660 are provided, wherein R 1b is CH2OCH3, A 1 is N, A 2a is CH and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0233] Table 1.66 660 compounds of formula (Ia) E66.1 to E66.660 are provided, wherein R 1b is CH2OCH3, A 1 is N, A 2a is CF and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0234] Table 1.67 660 compounds of formula (Ia) E67.1 to E67.660 are provided, wherein R 1b is CH2OCH3, A 1 is N, A 2a is CCl and R 2 , A2b , R 4 , R 5 is as defined in table Z.

[0235] Table 1.68 660 compounds of formula (Ia) E68.1 to E68.660 are provided wherein R 1b is CH2OCH3, A 1 is N, A 2a is CBr and R 2 , A 2b , R 4 , R 5 is as defined in table Z.

[0236] Table 1.69 660 compounds of formula (Ia) E69.1 to E69.660 are provided wherein R 1b is CH2OCH3, A 1 is N, A 2a is CCH3 and R 2 , A 2b , R 4 , R 5 is as defined in table Z.

[0237] Table 1.70 660 compounds of formula (Ia) E70.1 to E70.660 are provided wherein R 1b is CH2OCH3, A 1 is N, A 2a is CCH2CH3 and R 2 , A 2b , R 4 , R 5 is as defined in table Z.

[0238] Table 1.71 660 compounds of formula (Ia) E71.1 to E71.660 are provided wherein R 1b is CH2OCH3, A 1 is N, A 2a is CCN and R 2 , A 2b , R 4 , R 5 is as defined in table Z.

[0239] Table 1.72 660 compounds of formula (Ia) E72.1 to E72.660 are provided wherein R 1b is CH2OCH3, A 1 is N, A 2a is COCH3 and R2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0240] Table 1.73 660 compounds of formula (Ia) E73.1 to E73.660 are provided, wherein R 1b is cyclopropyl, A 1 is CH, A 2a is N and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0241] Table 1.74 660 compounds of formula (Ia) E74.1 to E74.660 are provided, wherein R 1b is cyclopropyl, A 1 is CH, A 2a is CH and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0242] Table 1.75 660 compounds of formula (Ia) E75.1 to E75.660 are provided, wherein R 1b is cyclopropyl, A 1 is CH, A 2a is CF and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0243] Table 1.76 660 compounds of formula (Ia) E76.1 to E76.660 are provided, wherein R 1b is cyclopropyl, A 1 is CH, A 2a is CCI and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0244] Table 1.77 660 compounds of formula (Ia) E77.1 to E77.660 are provided, wherein R 1b is cyclopropyl, A 1 is CH, A 2a is CBr and R 2, A 2b , R 4 , R 5 is as defined in Table Z.

[0245] Table 1.78 660 compounds of formula (Ia) E78.1 to E78.660 are provided wherein R 1b is cyclopropyl, A 1 is CH, A 2a is CCH3and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0246] Table 1.79 660 compounds of formula (Ia) E79.1 to E79.660 are provided wherein R 1b is cyclopropyl, A 1 is CH, A 2a is CCH2CH3and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0247] Table 1.80 660 compounds of formula (Ia) E80.1 to E80.660 are provided wherein R 1b is cyclopropyl, A 1 is CH, A 2a is CCN and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0248] Table 1.81 660 compounds of formula (Ia) E81.1 to E81.660 are provided wherein R 1b is cyclopropyl, A 1 is CH, A 2a is COCH3and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0249] Table 1.82 660 compounds of formula (Ia) E82.1 to E82.660 are provided wherein R 1b is cyclopropyl, A 1 is N, A 2a is N and R 2 , A2b 4 5 is as defined in Table Z.

[0250] Table 1.83 660 compounds of formula (Ia) E83.1 to E83.660 are provided, wherein R 1b is cyclopropyl, A 1 is N, A 2a is CH and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0251] Table 1.84 660 compounds of formula (Ia) E84.1 to E84.660 are provided, wherein R 1b is cyclopropyl, A 1 is N, A 2a is CF and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0252] Table 1.85 660 compounds of formula (Ia) E85.1 to E85.660 are provided, wherein R 1b is cyclopropyl, A 1 is N, A 2a is CCI and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0253] Table 1.86 660 compounds of formula (Ia) E86.1 to E86.660 are provided, wherein R 1b is cyclopropyl, A 1 is N, A 2a is CBr and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0254] Table 1.87 660 compounds of formula (Ia) E87.1 to E87.660 are provided, wherein R 1b is cyclopropyl, A 1 is N, A 2a is CCH3 and R 2 , A 2b ​​R 4 R 5 are as defined in Table Z.

[0255] Table 1.88 660 compounds of formula (Ia) E88.1 to E88.660 are provided wherein R 1b is cyclopropyl, A 1 is N, A 2a is CCN and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0256] Table 1.89 660 compounds of formula (Ia) E89.1 to E89.660 are provided wherein R 1b is cyclopropyl, A 1 is N, A 2a is CCN and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0257] Table 1.90 660 compounds of formula (Ia) E90.1 to E90.660 are provided wherein R 1b is cyclopropyl, A 1 is N, A 2a is COCH3 and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0258] Table 1.91 660 compounds of formula (Ia) E91.1 to E91.660 are provided wherein R 1b is CH2cyclopropyl, A 1 is CH, A 2a is N and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0259] Table 1.92 660 compounds of formula (Ia) E92.1 to E92.660 are provided wherein R 1b is CH2cyclopropyl, A 1 is CH, A 2a is CH and R 2 , A 2bR 4 R 5 are as defined in Table Z.

[0260] Table 1.93 660 compounds of formula (Ia) E93.1 to E93.660 are provided, wherein R 1b is CH2cyclopropyl, A 1 is CH, A 2a is CF and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0261] Table 1.94 660 compounds of formula (Ia) E94.1 to E94.660 are provided, wherein R 1b is CH2cyclopropyl, A 1 is CH, A 2a is CCI and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0262] Table 1.95 660 compounds of formula (Ia) E95.1 to E95.660 are provided, wherein R 1b is CH2cyclopropyl, A 1 is CH, A 2a is CBr and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0263] Table 1.96 660 compounds of formula (Ia) E96.1 to E96.660 are provided, wherein R 1b is CH2cyclopropyl, A 1 is CH, A 2a is CCH3 and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0264] Table 1.97 660 compounds of formula (Ia) E97.1 to E97.660 are provided, wherein R 1b is CH2cyclopropyl, A 1 is CH, A 2a is CCH2CH3 and R 2 , A2b , R 4 , R 5 is as defined in Table Z.

[0265] Table 1.98 660 compounds of formula (Ia) E98.1 to E98.660 are provided wherein R 1b is CH2cyclopropyl, A 1 is CH, A 2a is CCN and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0266] Table 1.99 660 compounds of formula (Ia) E99.1 to E99.660 are provided wherein R 1b is CH2cyclopropyl, A 1 is CH, A 2a is COCH3 and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0267] Table 1.100 660 compounds of formula (Ia) E100.1 to E100.660 are provided wherein R 1b is CH2cyclopropyl, A 1 is N, A 2a is N and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0268] Table 1.101 660 compounds of formula (Ia) E101.1 to E101.660 are provided wherein R 1b is CH2cyclopropyl, A 1 is N, A 2a is CH and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0269] Table 1.102 660 compounds of formula (Ia) E102.1 to E102.660 are provided wherein R 1b is CH2cyclopropyl, A 1 is N, A 2a is CF and R2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0270] Table 1.103 660 compounds E103.1 to E103.660 of formula (Ia) are provided, wherein R 1b is CH2cyclopropyl, A 1 is N, A 2a is CCI and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0271] Table 1.104 660 compounds E104.1 to E104.660 of formula (Ia) are provided, wherein R 1b is CH2cyclopropyl, A 1 is N, A 2a is CBr and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0272] Table 1.105 660 compounds E105.1 to E105.660 of formula (Ia) are provided, wherein R 1b is CH2cyclopropyl, A 1 is N, A 2a is CCH3 and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0273] Table 1.106 660 compounds E106.1 to E106.660 of formula (Ia) are provided, wherein R 1b is CH2cyclopropyl, A 1 is N, A 2a is CCH2CH3 and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0274] Table 1.107 660 compounds E107.1 to E107.660 of formula (Ia) are provided, wherein R 1b is CH2cyclopropyl, A 1 is N, A2a is CCN and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0275] Table 1.108 660 compounds of formula (Ia) E108.1 to E108.660 are provided, wherein R 1b is CH2cyclopropyl, A 1 is N, A 2a is COCH3and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0276] Table 1.109 660 compounds of formula (Ia) E109.1 to E109.660 are provided, wherein R 1b is NHAc, A 1 is CH, A 2a is N and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0277] Table 1.110 660 compounds of formula (Ia) E110.1 to E110.660 are provided, wherein R 1b is NHAc, A 1 is CH, A 2a is CH and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0278] Table 1.111 660 compounds of formula (Ia) E111.1 to E111.660 are provided, wherein R 1b is NHAc, A 1 is CH, A 2a is CF and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0279] Table 1.112 660 compounds of formula (Ia) E112.1 to E112.660 are provided, wherein R 1b is NHAc, A 1is CH, A 2a is CCI and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0280] Table 1.113 660 compounds of formula (Ia) E113.1 to E113.660 are provided, wherein R 1b is NHAc, A 1 is CH, A 2a is CBr and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0281] Table 1.114 660 compounds of formula (Ia) E114.1 to E114.660 are provided, wherein R 1b is NHAc, A 1 is CH, A 2a is CCH3 and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0282] Table 1.115 660 compounds of formula (Ia) E115.1 to E115.660 are provided, wherein R 1b is NHAc, A 1 is CH, A 2a is CCH2CH3 and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0283] Table 1.116 660 compounds of formula (Ia) E116.1 to E116.660 are provided, wherein R 1b is NHAc, A 1 is CH, A 2a is CCN and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0284] Table 1.117 660 compounds of formula (Ia) E117.1 to E117.660 are provided, wherein R 1bis NHAc, A 1 is CH, A 2a is COCH3and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0285] Table 1.118 660 compounds of formula (Ia) E118.1 to E118.660 are provided, wherein R 1b is NHAc, A 1 is N, A 2a is N and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0286] Table 1.119 660 compounds of formula (Ia) E119.1 to E119.660 are provided, wherein R 1b is NHAc, A 1 is N, A 2a is CH and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0287] Table 1.120 660 compounds of formula (Ia) E120.1 to E120.660 are provided, wherein R 1b is NHAc, A 1 is N, A 2a is CF and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0288] Table 1.121 660 compounds of formula (Ia) E121.1 to E121.660 are provided, wherein R 1b is NHAc, A 1 is N, A 2a is CCI and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0289] Table 1.122 660 compounds of formula (Ia) E122.1 to E122.660 are provided, wherein R1b is NHAc, A 1 is N, A 2a is CBr and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0290] Table 1.123 660 compounds of formula (Ia) E123.1 to E123.660 are provided, wherein R 1b is NHAc, A 1 is N, A 2a is CCH3 and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0291] Table 1.124 660 compounds of formula (Ia) E124.1 to E124.660 are provided, wherein R 1b is NHAc, A 1 is N, A 2a is CCH2CH3 and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0292] Table 1.125 660 compounds of formula (Ia) E125.1 to E125.660 are provided, wherein R 1b is NHAc, A 1 is N, A 2a is CCN and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0293] Table 1.126 660 compounds of formula (Ia) E126.1 to E126.660 are provided, wherein R 1b is NHAc, A 1 is N, A 2a is COCH3 and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0294] Table 1.127660 compounds of formula (Ia) E127.1 to E127.660 are provided wherein R 1b is CN, A 1 is CH, A 2a is N and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0295] Table 1.128 660 compounds of formula (Ia) E128.1 to E128.660 are provided wherein R 1b is CN, A 1 is CH, A 2a is CH and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0296] Table 1.129 660 compounds of formula (Ia) E129.1 to E129.660 are provided wherein R 1b is CN, A 1 is CH, A 2a is CF and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0297] Table 1.130 660 compounds of formula (Ia) E130.1 to E130.660 are provided wherein R 1b is CN, A 1 is CH, A 2a is CCI and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0298] Table 1.131 660 compounds of formula (Ia) E131.1 to E131.660 are provided wherein R 1b is CN, A 1 is CH, A 2a is CBr and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0299] Table 1.132660 compounds of formula (Ia) E132.1 to E132.660 are provided wherein R 1b is CN, A 1 is CH, A 2a is CCH3and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0300] Table 1.133 660 compounds of formula (Ia) E133.1 to E133.660 are provided wherein R 1b is CN, A 1 is CH, A 2a is CCH2CH3and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0301] Table 1.134 660 compounds of formula (Ia) E134.1 to E134.660 are provided wherein R 1b is CN, A 1 is CH, A 2a is CCNand R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0302] Table 1.135 660 compounds of formula (Ia) E135.1 to E135.660 are provided wherein R 1b is CN, A 1 is CH, A 2a is COCH3and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0303] Table 1.136 660 compounds of formula (Ia) E136.1 to E136.660 are provided wherein R 1b is CN, A 1 is N, A 2a is Nand R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0304] Table 1.137 660 compounds E137.1 to E137.660 of formula (Ia) are provided, wherein R 1b is CN, A 1 is N, A 2a is CH and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0305] Table 1.138 660 compounds E138.1 to E138.660 of formula (Ia) are provided, wherein R 1b is CN, A 1 is N, A 2a is CF and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0306] Table 1.139 660 compounds E139.1 to E139.660 of formula (Ia) are provided, wherein R 1b is CN, A 1 is N, A 2a is CCI and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0307] Table 1.140 660 compounds E140.1 to E140.660 of formula (Ia) are provided, wherein R 1b is CN, A 1 is N, A 2a is CBr and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0308] Table 1.141 660 compounds E141.1 to E141.660 of formula (Ia) are provided, wherein R 1b is CN, A 1 is N, A 2a is CCH3 and R 2 , A 2b , R 4 , R 5 are as defined in table Z.

[0309] Table 1.142 660 compounds of formula (Ia) E142.1 to E142.660 are provided, wherein R 1b is CN, A 1 is N, A 2a is CCH2CH3and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0310] Table 1.143 660 compounds of formula (Ia) E143.1 to E143.660 are provided, wherein R 1b is CN, A 1 is N, A 2a is CCN and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0311] Table 1.144 660 compounds of formula (Ia) E144.1 to E144.660 are provided, wherein R 1b is CN, A 1 is N, A 2a is COCH3and R 2 , A 2b , R 4 , R 5 are as defined in Table Z.

[0312] The compounds according to the application can have many benefits, including inter alia a favorable level of biological activity for the protection of plants against diseases caused by fungi or superior properties for use as active ingredients for agrochemicals (e.g. higher biological activity, a favorable spectrum of activity, increased safety, improved physical-chemical properties, or increased biodegradability). The compounds according to the application have a particularly advantageous level of biological activity for the protection of plants against Oomycetes (such as Phytophthora, Plasmopara and Pythium).

[0313] Compounds of formula (I) according to the application, wherein Z is O, can be prepared as shown in Schemes 1 to 14 below, wherein (unless otherwise specified) the definition of each variable is as defined in the application.

[0314] Compounds of formula (I) can be prepared via the reaction of a compound of formula (II), wherein X is CI, Br or I, and a compound of formula (III), wherein any one of R 6 independently of one another are hydrogen, C 1-6 alkyl, or wherein two R 6together can form C 3-8 (VIII) in the presence of a base such as Cs2C03, K2C03, or NaOtBu and a suitable palladium catalyst such as tetrakis(triphenylphosphine)palladium, [1,1 - bis(diphenylphosphino)ferrocene]dichloropalladium(ll), bis(diphenylphosphino)palladium(ll) chloride, palladium dichloride, or palladium acetate in a suitable solvent such as dimethylformamide, dioxane, tetrahydrofuran, ethanol, or water. Compounds of formula (III) wherein any one of R 6 independently of each other are hydrogen, C 1-6 alkyl, or wherein two R 6 together can form C 3-8 cycloalkyl) are prepared by known methods or are commercially available. This transformation is depicted in Scheme 1.

[0315]

[0316] Compounds of formula (II) wherein X is CI, Br, or I can be prepared by reaction of a compound of formula (IV) wherein X is CI, Br, or I with a compound of formula (V) wherein X 1 is a good leaving group such as CI, Br, I, triflate, tosyl, or mesyl) in the presence of a base such as Cs2C03, K2C03, NaH, or NaOtBu. This transformation is depicted in Scheme 2.

[0317]

[0318] Compounds of formula (IV) wherein X is CI, Br, or I can be obtained by reaction of an amine compound of formula (VI) wherein X is CI, Br, or I with a compound of formula (VII) wherein X 2is OH) of the carboxylic acid function of the compound of formula (VII) which is a process that usually occurs by converting the -OH of the carboxylic acid into a good leaving group (such as a chloride group), for example by using (COCl)2or SOCl2, followed by treatment with a compound of formula (VI) wherein X is Cl, Br or I, preferably in a suitable solvent (for example N-methylpyrrolidinone, acetonitrile, dimethylacetamide, dichloromethane or tetrahydrofuran), preferably at a temperature between 25 and 60 °C, and optionally in the presence of a base such as triethylamine or N,N-diisopropylethylamine; or alternatively under conditions described in the literature for amide coupling (such as 1-propane phosphonic acid anhydride (T3P)) in a suitable solvent (for example acetonitrile), optionally in the presence of a base (for example triethylamine or N,N-diisopropylethylamine). For example, see Chem. Soc. Rev. [Chemical Society Reviews] 2009, 38, 606 and Chem. Soc. Rev. [Chemical Society Reviews] 2011, 40, 5084. This transformation is depicted in Scheme 3.

[0319]

[0320] Alternatively, the compound of formula (II) wherein X is Cl, Br or I can be obtained in two steps by reacting an amine compound of formula (VI) wherein X is Cl, Br or I with a compound of formula (V) wherein X 1 is a good leaving group such as Cl, Br, I, triflate, tosyl or mesyl) in the presence of a base such as Cs2CO3, K2CO3, NaH or NaOtBu; then the obtained amine of formula (IX) wherein X is Cl, Br or I is reacted with a compound of formula (VII) wherein X 2 is OH) in a peptide coupling transformation. Alternatively, the compound of formula (IX) wherein X is Cl, Br or I can be obtained from the amine of formula (VI) wherein X is Cl, Br or I by reaction with an aldehyde of formula (VIII) wherein R 9 is C 1-5 alkyl, C 1-5 alkoxy-C 1-5 alkyl, C 3-6 cycloalkyl-C 1-3 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, C 1-5 alkoxy, C 1-6 alkylsulfanyl-C 1-5 alkyl, C 1-6 alkylsulfinyl-C 1-5 alkyl, C1-6 alkylsulfonyl-C 1-5 alkyl, C 1-6 alkoxycarbonyl-C 1-5 alkyl, C 1-6 alkylaminocarbonyl-C 1-5 alkyl, or diC 1-6 alkylaminocarbonyl-C 1-6 alkyl) is obtained, for example, by reductive amination in the presence of NaBH(OAc)3or NaBH3CN in a suitable solvent, eventually in the presence of a Bronsted or Lewis acid (such as acetic acid). Alternatively, another reagent system for reductive amination uses a combination of titanium isopropoxide and NaBH4. The synthesis of compounds of formula (II) wherein X is Cl, Br or I from amines of formula (VI) wherein X is Cl, Br or I is depicted in Scheme 4.

[0321]

[0322] Alternatively, compounds of formula (II) wherein X is Cl, Br or I can be prepared by reacting compounds of formula (X) 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). Compounds of formula (X) can be obtained by reacting compounds of formula (XI) with compounds of formula (V) wherein X 1 is a good leaving group such as Cl, Br, I, triflate, tosyl or mesyl) in the presence of a base (such as Cs2CO3, K2CO3, NaH or NaOtBu). Compounds of formula (XI) can be obtained by reacting amines of formula (XII) with compounds of formula (VII) wherein X 2 is OH) in a peptide coupling transformation using the conditions described above. Alternatively, compounds of formula (X) can be obtained by reacting amines of formula (XIII) with compounds of formula (VII) wherein X 2 is OH and Z is O or S) in a peptide coupling transformation using the conditions described above. Amines of formula (XIII) can be prepared by reacting amines of formula (XII) with compounds of formula (V) wherein X 1 is a good leaving group such as Cl, Br, I, triflate, tosyl or mesyl) in the presence of a base (such as Cs2CO3, K2CO3, NaH or NaOtBu). Alternatively, compounds of formula (XIII) can be obtained from amines of formula (XII) by reaction with aldehydes of formula (VIII) wherein R 9 is C 1-5alkyl, C 1-5 alkoxy-C 1-5 alkyl, C 3-6 cycloalkyl-C 1-3 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, C 1-5 alkoxy, C 1-6 alkylsulfanyl-C 1-5 alkyl, C 1-6 alkylsulfinyl-C 1-5 alkyl, C 1-6 alkylsulfonyl-C 1-5 alkyl, C 1-6 alkoxycarbonyl-C 1-5 alkyl, C 1-6 alkylaminocarbonyl-C 1-5 alkyl, or diC 1-6 alkylaminocarbonyl-C 1-6 alkyl), for example in the presence of NaBH(OAc)3or NaBH3CN in a suitable solvent, eventually in the presence of a Bronsted or Lewis acid (such as acetic acid) to perform a reductive amination. Alternatively, another reagent system for reductive amination uses a combination of titanium isopropoxide and NaBH4. These transformations are described in Scheme 5.

[0323]

[0324] Compounds of formula (VI) wherein X is CI, Br or I can be prepared by reduction of nitro compounds of formula (XIV) wherein X is CI, Br or I using a reducing agent such as stannous chloride dihydrate or iron in the presence of ammonium chloride or acetic acid. This transformation has been described in the literature (see for example Tetrahedron Lett. 1984, 25, 839). Compounds of formula (XIV) wherein X is CI, Br or I can be obtained by halogenation of compounds of formula (XV) using a halogenating agent such as N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide or bromine in a suitable solvent such as dichloromethane, chloroform, tetrahydrofuran or acetonitrile. Alternatively, compounds of formula (VI) wherein X is CI, Br or I can be prepared by reduction of amines of formula (XVI) wherein X is CI, Br or I and X 3(XVI) by deprotection of the amine protecting group (such as tert-butoxycarbonyl or benzyloxycarbonyl). Amines of formula (XVI) (wherein X is CI, Br or I) can be generated from a Curtius rearrangement by treatment of a carboxylic acid of formula (XVII) (wherein X is CI, Br or I) with an azide reagent (such as diphenyl phosphoric azide or sodium azide) in the presence of a base (preferably triethylamine) and a solvent (such as tert-butanol). Examples of this transformation have been described in WO 2008 / 091195 (page 57). Alternatively, the reaction can be performed using Boc2O and some catalysts (such as tetrabutylammonium bromide and zinc triflate) as described in Org. Lett. 2005, 7, 4107. These transformations are depicted in Scheme 6.

[0325]

[0326] Compounds of formula (XVII) (wherein X is CI, Br or I) are either commercially available or alternatively can be prepared by saponification of a compound of formula (XVIII) (wherein X is CI, Br or I and R 7 is C 1-6 alkyl) in a suitable solvent (such as methanol, ethanol or water) at a temperature between room temperature and reflux using a base (such as NaOH or LiOH). Compounds of formula (XVIII) (wherein X is CI, Br or I and R 7 is C 1-6 alkyl) are either commercially available or alternatively can be prepared from a compound of formula (XIX) (wherein R 7 is C 1-6 alkyl) and a halogenating agent (such as N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide or bromine) in a suitable solvent (such as dichloromethane, chloroform, tetrahydrofuran or acetonitrile). These transformations are depicted in Scheme 7.

[0327]

[0328] Compounds of formula (XIX) (wherein R 7 is C 1-6 alkyl) are either commercially available or alternatively can be prepared by reaction of a compound of formula (XX) (wherein X is CI, Br or I) with carbon monoxide and an alcohol in the presence of a catalyst (such as [1,1 -bis-(diphenylphosphino)ferrocene] dichloropalladium(II)), and optionally a base (such as triethylamine). This transformation is depicted in Scheme 8.

[0329]

[0330] Compounds of formula (XV) are commercially available or, alternatively, can be prepared by reacting a compound of formula (XXI) and a compound of formula (XXII) (where X is CI, Br or I) or its corresponding acetal of formula (XXIII) (where X is CI, Br or I, and either R 8 are each, independently of the other, C 1-6 alkyl, or wherein two R 8 together can form a C 3-8 cycloalkyl) in a solvent such as water, ethanol, acetone or acetonitrile. In some cases, the outcome of the reaction can be improved by using a base such as sodium bicarbonate or potassium carbonate, or by using an acid such as p-toluenesulfonic acid or hydrogen bromide. Furthermore, this transformation can be used to prepare compounds of formula (XX) (where X is CI, Br or I) from compounds of formula (XXIV) (where X is CI, Br or I), and compounds of formula (XIX) (where R 7 is C 1-6 alkyl) from compounds of formula (XXV) (where R 7 is C 1-6 alkyl). Compounds of formula (XXI), compounds of formula (XXIV) (where X is CI, Br or I) and compounds of formula (XXV) (where R 7 is C 1-6 alkyl) are prepared by known methods or are commercially available. These transformations are depicted in Scheme 9.

[0331]

[0332] Alternatively, compounds of formula (I) can be prepared by alkylating a compound of formula (XXVI) with a compound of formula (V) (where X 1 is a good leaving group such as CI, Br, I, triflate, tosyl or mesyl) in the presence of a base such as Cs2C03, K2C03, NaH or NaOtBu. Compounds of formula (XXVI) can be obtained by reacting an amine of formula (XXVII) with a compound of formula (VII) (where X 2 is OH) using the conditions described above in a peptide coupling transformation. Alternatively, compounds of formula (XXVII) can be alkylated with a compound of formula (V) (where X 1 is a good leaving group such as CI, Br, I, triflate, tosyl or mesyl) in the presence of a base such as Cs2C03, K2C03, NaH or NaOtBu to give a compound of formula (XXVIII). Amines of formula (XXVIII) are reacted with a compound of formula (VII) (where X2 The reaction in peptide coupling transformation using the conditions described above (I) can provide compounds having formula (I). These transformations are depicted in Scheme 10.

[0333]

[0334] Compounds having formula (XXVII) can be reacted, for example, with an acid (such as trifluoroacetic acid or hydrochloric acid) or other methods generally known to those skilled in the art with amines having formula (XXIX) (where X... 3 It is prepared by deprotecting a hydrogen or amine protecting group (such as tert-butoxycarbonyl or benzyloxycarbonyl). An amine having the formula (XXIX) (where X...) 3 A hydrogen or amine protecting group (such as tert-butoxycarbonyl or benzyloxycarbonyl) can be used via a compound having the formula (XVI) (where X is Cl, Br, or I and X... 3 It is a hydrogen or amine protecting group (such as tert-butoxycarbonyl or benzyloxycarbonyl) and a compound having formula (III) (where A) 1 It is CH or N and any one of R 6 Hydrogen and C are independent of each other. 1-6 Alkyl, or two of the Rs 6 Together they can form C 3-8 The cycloalkyl group was prepared by Suzuki cross-coupling in a suitable solvent (such as dimethylformamide, dioxane, tetrahydrofuran, ethanol, or water) in the presence of a base (such as Cs₂CO₃, K₂CO₃, or NaOtBu) and a suitable palladium catalyst (such as tetra(triphenylphosphine)palladium, [1,1-bis(diphenylphosphine)ferrocene]palladium(II) dichloride, bis(diphenylphosphine)palladium(II), palladium dichloride, or palladium acetate). These transformations are depicted in Scheme 11.

[0335]

[0336] Alternatively, a compound having formula (I) can be obtained by mixing a compound having formula (XXX) with a compound having formula (XXXI) (where X... 2 (Is OH) is prepared by using the reaction described above in peptide coupling conversion. Compounds having formula (XXX) can be prepared by reacting a compound having formula (II) and a compound having formula (XXXII) (where either R) 6 Hydrogen and C are independent of each other. 1-6 Alkyl, or two of the Rs 6 Together they can form C 3-8Compounds of formula (XXXII) (wherein any one of R 6 independently of each other are hydrogen, C 1-6 alkyl, or wherein two R 6 together can form a C 3-8 cycloalkyl) are prepared by known methods or are commercially available. These transformations are depicted in Scheme 12.

[0337]

[0338] Compounds of formula (lb) (wherein Z is S) can be prepared by reacting compounds of formula (I) (wherein 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 depicted in Scheme 13.

[0339]

[0340] Alternatively, compounds of formula (lb) (wherein Z is S) can be prepared by reacting compounds of formula (XXXb) with compounds of formula (XXXI) (wherein X 2 is OH) in a peptide coupling transformation using the conditions described above. Compounds of formula (XXXb) can be prepared by reacting compounds of formula (XXX) with phosphorus pentasulfide or Lawesson's reagent (CAS: 19172-47-5) in a suitable solvent such as toluene, xylene or dichloromethane. This transformation is depicted in Scheme 14.

[0341]

[0342] When the term "compound(s) according to the application" is used, it refers to the compounds according to the application.

[0343] Alternatively, compounds according to the application can be obtained by using standard synthesis techniques known to the person skilled in the art. Non-exhaustive examples include oxidation reactions, reduction reactions, hydrolysis reactions, coupling reactions, aromatic nucleophilic or electrophilic substitution reactions, nucleophilic substitution reactions, nucleophilic addition reactions, olefination reactions, oxime formation, alkylation and halogenation reactions.

[0344] The compounds according to the application can be converted in a manner known per se to another compound according to the application by replacing one or more substituents of a starting compound according to the application by another or a further substituent or substituents according to the application in a conventional manner.

[0345] Depending on the reaction conditions and the choice of starting materials appropriate to the individual case, it is possible, for example, to replace only one substituent by another substituent according to the application in one reaction step, or several substituents can be replaced by other substituents according to the application in the same reaction step.

[0346] Salts of the compounds according to the application can be prepared in a manner known per se. Thus, for example, acid addition salts of compounds according to the application are obtained by treatment with a suitable acid or a suitable ion exchanger reagent, and salts with bases are obtained by treatment with a suitable base or with a suitable ion exchanger reagent.

[0347] Salts of the compounds according to the application can be converted in a manner known per se, for example, into the free compounds, acid addition salts (for example by treatment with a suitable basic compound or a suitable ion exchanger reagent) and salts with bases (for example by treatment with a suitable acid or a suitable ion exchanger reagent).

[0348] Salts of the compounds according to the application can be converted in a manner known per se into other salts of compounds according to the application, acid addition salts, for example into other acid addition salts, for example by treatment with a suitable metal salt of an acid, such as a sodium, barium or silver salt, for example with silver acetate, of an inorganic acid, such as hydrochloric acid, in a suitable solvent in which the salt, for example silver chloride, formed does not dissolve and thus precipitates from the reaction mixture.

[0349] Depending on the procedure or the reaction conditions, the compounds according to the application which have salt-forming properties can be obtained in free form or in salt form.

[0350] Depending on the number of asymmetric carbon atoms present in the molecule, the absolute and relative configuration and / or depending on the configuration of non-aromatic double bonds present in the molecule, the compounds according to the application and, where appropriate, their tautomers, in each case in free form or in salt form, can be present in the form of one of the possible stereoisomers or as a mixture of these, for example in the form of pure stereoisomers, such as enantiomers and / or diastereomers, or as a stereoisomer mixture, such as an enantiomer mixture, for example a racemate, a diastereomer mixture or a racemate mixture; the present application relates to the pure stereoisomers and also to all possible stereoisomer mixtures and is to be understood in each case in this sense above and below, even when stereochemical details are not explicitly mentioned in each case.

[0351] Diastereomer mixtures or racemate mixtures of the compounds according to the application in free form or in salt form, which can be obtained depending on the starting materials and procedures chosen, can be separated into the pure diastereomers or racemates in a known manner on the basis of the physicochemical differences of the components, for example by fractional crystallization, distillation and / or chromatography.

[0352] Enantiomer mixtures, such as racemates, which can be obtained in an analogous manner, can be resolved into the optical enantiomers by known methods, for example by recrystallization from an optically active solvent; by chromatography on a chiral adsorbent, for example high-performance liquid chromatography (HPLC) on acetylcellulose; with the aid of suitable microorganisms, by cleavage with specific immobilized enzymes; by complex formation with compounds, for example using chiral crown ethers, in which only one enantiomer is complexed; or by conversion into diastereomeric salts of acids, for example by reaction of basic final products racemates with optically active acids, such as carboxylic acids, for example camphoric acid, tartaric acid or malic acid, or sulfonic acids, for example camphorsulfonic acid, and separation of the diastereomeric mixtures which can be obtained in this way, for example by fractional crystallization on the basis of their different solubilities, to give the diastereomers from which the desired enantiomers can be liberated by the action of suitable reagents, for example basic reagents.

[0353] The pure diastereomers or enantiomers can be obtained according to the application not only by separation of suitable stereoisomer mixtures, but also by generally known methods of diastereoselective or enantioselective synthesis, for example by carrying out the methods according to the application with starting materials having suitable stereochemistry.

[0354] The N-oxides can be prepared by reacting the compounds according to the application with a suitable oxidizing agent, for example H2O2 / urea adduct, in the presence of an acid anhydride, for example trifluoroacetic anhydride. Such oxidations are known from the literature, for example from J. Med. Chem. 32(12), 2561-73, 1989 or WO 00 / 15615.

[0355] If the individual components have different biological activities, it is advantageous to isolate or synthesize in each case the biologically more effective stereoisomer, for example the enantiomer or diastereomer or a mixture of stereoisomers, for example an enantiomeric or diastereomeric mixture.

[0356] If appropriate, the compounds according to the application and, where appropriate, the tautomers thereof, in each case in free form or in salt form, can also be obtained in the form of hydrates and / or include other solvents, such as, for example, those which can have been used for the crystallization of compounds which are present in solid form.

[0357] The following examples illustrate but do not limit the application.

[0358] The present application also provides intermediates useful for preparing the compounds according to the application.

[0359] The following intermediates form a further aspect of the present application.

[0360] A compound of formula (II)

[0361]

[0362] wherein Z is O or S, and preferably Z is O;

[0363] R 1a , R 1b and R 1c are independently selected from the group consisting of hydrogen, hydroxyl, 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, C 2-4 alkenyl, and -NHC(O)C 1-6 alkyl; and preferably, R 1a and R 1c are hydrogen, and R 1b may be selected from the group consisting of hydrogen, C1-6 alkyl, C 3-6 cycloalkyl, C 1-6 alkoxy-C 1-6 alkyl, and C 2-4 alkenyl;

[0364] A 2 independently CR 2 or N, provided that no more than four A 2 are N, preferably no more than three A 2 are N, preferably no more than two A 2 are N, preferably no more than one A 2 are N, and more preferably five A 2 are CR 2 ;

[0365] R 2 is independently selected from the group consisting of hydrogen, hydroxyl, halogen, CN, C 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, di-C 1-6 alkylaminocarbonyl, C 1-6 alkylcarbonyl, amino, C 1-6 alkylamino, di-C 1-6 -alkylamino, and C 3-6 cycloalkylamino, wherein the C 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, C1-6 alkylcarbonyl, C 1-6 alkylaminocarbonyl, diC 1-6 alkylaminocarbonyl, C 1-6 alkylcarbonyl, C 1-6 alkylcarbonyl, C 1-6 alkylaminocarbonyl, diC 1-6 alkylaminocarbonyl, C 1-6 alkylcarbonyl, amino, C 1-6 alkylamino, diC 1-6 -alkylamino, and C 3-6 each of the cycloalkyl groups is optionally substituted with one to three substituents independently selected from the group consisting of halogen, hydroxyl, and CN, and more preferably, R 2 is independently selected from the group consisting of hydrogen, hydroxyl, halogen, CN, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkoxy, C 3-6 cycloalkyl, C 1-6 alkylsulfanyl, C 1-6 alkylsulfonyl, C 1-6 alkoxycarbonyl, C 1-6 alkylaminocarbonyl, and diC 1-6 alkylaminocarbonyl, wherein the C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkoxy, C 3-6 cycloalkyl, C 1-6 alkylsulfanyl, C 1-6 alkylsulfonyl, C 1-6 alkoxycarbonyl, C 1-6 alkylaminocarbonyl, diC 1-6 alkylaminocarbonyl, and C 1-6 each of the alkylcarbonyl groups is optionally substituted with one to three substituents independently selected from the group consisting of halogen, hydroxyl, and CN;

[0366] R 4 is selected from the group consisting of 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, C1-6 alkyl, 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, di-C 1-6 alkylaminocarbonyl-C 1-6 alkyl, and CN, wherein the 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, and di-C 1-6 alkylaminocarbonyl-C 1-6 each of the alkyl groups is optionally substituted with one to three substituents independently selected from the group consisting of halogen and CN; and preferably R 4 is selected from the group consisting of C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 alkyl, and C 1-6 alkoxy, wherein the C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 alkyl, and C 1-6 alkoxy, wherein each of the alkyl groups is optionally substituted with one to three substituents independently selected from the group consisting of halogen and CN; and

[0367] X is CI, Br or I;

[0368] or salts or N-oxides thereof.

[0369] A compound of formula (X)

[0370]

[0371] wherein Z is O or S, and preferably Z is O;

[0372] R 1a , R 1b and R 1c are independently selected from the group consisting of hydrogen, hydroxyl, 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, C 2-4 alkenyl, and -NHC(O)C 1-6 alkyl; and preferably, R 1a and R 1c are hydrogen, and R 1b may be selected from the group consisting of hydrogen, C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 alkoxy-C 1-6 alkyl, and C 2-4 alkenyl;

[0373] A 2 is independently CR 2 or N, provided that no more than four A 2 are N, preferably no more than three A 2 are N, preferably no more than two A 2 are N, preferably no more than one A 2 is N, and more preferably five A 2 are CR 2 ;

[0374] R 2 is independently selected from the group consisting of hydrogen, hydroxyl, halogen, CN, C 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, di-C 1-6 alkylaminocarbonyl, C 1-6 alkylcarbonyl, amino, C 1-6 alkylamino, di-C 1-6 -alkylamino, and C 3-6 cycloalkylamino, wherein each of the C 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, di-C 1-6 alkylaminocarbonyl, C 1-6 alkylcarbonyl, C 1-6 alkoxycarbonyl, C 1-6 alkylaminocarbonyl, di-C 1-6 alkylaminocarbonyl, C 1-6 alkylcarbonyl, amino, C 1-6 alkylamino, di-C 1-6 -alkylamino, and C 3-6 cycloalkylamino, wherein each of the C 2 is optionally substituted with one to three substituents independently selected from the group consisting of halogen, hydroxyl, and CN; and more preferably, R 1-6 is independently selected from the group consisting of hydrogen, hydroxyl, halogen, CN, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkoxy-C 3-6 cycloalkyl, C 1-6 alkylsulfanyl, C 1-6alkylsulfonyl, C 1-6 alkoxycarbonyl, C 1-6 alkylaminocarbonyl, and di-C 1-6 alkylaminocarbonyl, wherein the C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkoxy, C 3-6 cycloalkyl, C 1-6 alkylsulfanyl, C 1-6 alkylsulfonyl, C 1-6 alkoxycarbonyl, C 1-6 alkylaminocarbonyl, and di-C 1-6 each of alkylaminocarbonyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, hydroxyl, and CN; and

[0375] R 4 selected from 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, di-C 1-6 alkylaminocarbonyl-C 1-6 alkyl, and CN, wherein the 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 1-6alkyl, C 1-6 alkylsulfonyl-C 1-6 alkyl, C 1-6 alkyl, C 1-6 alkyl, C 1-6 alkyl, C 1-6 alkyl and diC 1-6 alkyl, C 1-6 each of the alkyl groups is optionally substituted with one to three substituents independently selected from the group consisting of halogen and CN; and preferably R 4 selected from the group consisting of C 1-6 alkyl, C 1-6 alkyl, C 1-6 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 alkyl, and C 1-6 alkoxy, wherein the C 1-6 alkyl, C 1-6 alkyl, C 1-6 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 alkyl, and C 1-6 each of the alkyl groups is optionally substituted with one to three substituents independently selected from the group consisting of halogen and CN; and preferably R

[0376] or a salt or N-oxide thereof.

[0377] a compound of formula (XVII)

[0378]

[0379] wherein A 1 is CH or N, and preferably is N;

[0380] R 1a , R 1b and R 1c are independently selected from the group consisting of hydrogen, hydroxyl, halogen, CN, C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 alkyl, C 1-6 cycloalkyl-C 3-6 alkyl, C 1-4 alkyl, C 1-6 alkylsulfanyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 alkoxy, amino, C 2-4 alkenyl, and -NHC(O)C 1-6 alkyl; and preferably, R 1a and R1c is hydrogen, and R 1b may be selected from hydrogen, C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 alkoxy-C 1-6 alkyl, and C 2-4 alkenyl; and

[0381] R 5 is selected from 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, di-C 1-6 alkylamino, C 1-6 alkoxyamino, and C 1-6 alkyl C 1-6 alkoxyamino, wherein each of said 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, di-C 1-6 alkylamino, C 1-6 alkoxyamino, and C 1-6 alkyl C 1-6 alkoxyamino is optionally substituted with one to three substituents independently selected from the group consisting of halogen and CN; preferably R 5 is selected from C 1-6 alkyl, C 1-6 alkoxy, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 alkyl, and C 1-6 alkoxy C 1-6 alkyl, wherein each of said groups is optionally substituted with one to three substituents independently selected from the group consisting of halogen and CN;

[0382] or a salt or N-oxide thereof.

[0383] a compound of formula (XVIII)

[0384]

[0385] wherein A 1 is CH or N, and preferably N;

[0386] R 1a , R 1b and R 1c are independently selected from the group consisting of hydrogen, hydroxyl, 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, C 2-4 alkenyl, and -NHC(O)C 1-6 alkyl; and preferably, R 1a and R 1c are hydrogen, and R 1b may be selected from the group consisting of hydrogen, C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 alkoxy-C 1-6 alkyl, and C 2-4 alkenyl;

[0387] R 4 is selected from the group consisting of 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, wherein the C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 alkyl, C2-6 alkenyl, C 2-6 alkynyl group, C 1-6 Alkoxy, C 1-6 Alkylthio-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 optionally be substituted by one to three independent substituents selected from the following: halogen and CN; preferably R. 4 Selected from C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 Alkyl and C 1-6 alkoxy group, wherein the C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 Alkyl and C 1-6 Each of the alkoxy groups may optionally be substituted by one to three independent substituents selected from the following: halogens and CN; and

[0388] R 5 Selected from 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, wherein the 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, C1-6 alkylamino, diC 1-6 alkylamino, C 1-6 alkoxyamino, and C 1-6 alkyl C 1-6 each of the alkylamino groups is optionally substituted with one to three substituents independently selected from the group consisting of halogen and CN; preferably R 5 selected from the group consisting of C 1-6 alkyl, C 1-6 alkoxy, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 alkyl, and C 1-6 alkoxy C 1-6 alkyl, wherein each of said groups is optionally substituted with one to three substituents independently selected from the group consisting of halogen and CN;

[0389] or salts or N-oxides thereof.

[0390] The compounds of formula (I) as defined by the present invention can be used as active ingredients in the agricultural sector and related areas of use, for example for controlling plant pathogens, or on non-living materials for the control of spoilage microorganisms or organisms potentially harmful to man. The novel compounds are characterized by excellent activity at low application rates, are well tolerated by plants and are safe for the environment. They have very useful curative, preventive and systemic properties and can be used for protecting numerous cultivated plants. The compounds of formula (I) as defined by the present invention can be used for inhibiting or destroying the pathogens that occur on plants or plant parts (fruit, flowers, leaves, stems, tubers, roots) of different crops of useful plants, while also protecting those plants parts that grow later from infestation by, for example, phytopathogenic microorganisms.

[0391] The compounds of formula (I) as defined by the present invention can also be used as fungicides. As used herein, the term "fungicide" means a compound that controls, modifies, or prevents the growth of fungi. The term "fungicidally effective amount" means an amount of such a compound or combination of such compounds that is capable of having an effect on the growth of fungi. Controlling or modifying effects include all deviations from natural development, such as killing, retarding, and the like, and preventing includes forming a barrier or other defense within or on the plant to prevent fungal infestation.

[0392] The compounds of formula (I) as defined by the present application can also be used as seed dressings for the treatment of plant propagation material, such as seeds (if fruits, tubers, or grains), or plant cuttings (e.g. rice), for protection against fungal infestation together with against phytopathogenic fungi present in the soil. The propagation material can be treated with a composition comprising a compound of formula (I) as defined by the present application before planting: for example, it can be dressed before sowing. The compounds of formula (I) as defined by the present application can also be applied to cereals (coating) by impregnating the seeds in a liquid formulation or by coating them with a solid formulation. The composition can also be applied to the planting site at the time of planting the propagation material, for example to the seed furrow during sowing. The present application also relates to such methods of treating plant propagation material, and to the plant propagation material so treated.

[0393] Furthermore, the compounds of formula (I) as defined by the present application can be used for controlling the fungi of the pertinent art, for example in the protection of industrial materials, including wood and technical products related to wood, in food storage, in hygiene management.

[0394] In addition, the present application can be used for protecting non-living materials (such as timber, wallboard and paints) from fungal attack.

[0395] The compounds of formula (I) as defined by the present application and the fungicidal compositions containing them can be used for controlling plant diseases caused by a broad spectrum of fungal plant pathogens. They are effective in controlling a broad spectrum of plant diseases, such as foliar pathogens of ornamentals, turf, vegetables, field crops, cereals, and fruit crops.

[0396] These fungi and fungal carriers of diseases which can be controlled, together with phytopathogenic bacteria and viruses, are, for example:

[0397] P. umbellatus, Alternaria spp., Scedosporium spp., Aschersonia spp., Aspergillus spp. (including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terreus), Aureobasidium spp. (including A. pullulans), Blastomyces dermatidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp. (including B. dothidea, B. obtusa), Botrytis spp. (including B. cinerea), Candida spp. (including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis), Cephaloascus fragrans, Ceratocystis spp., Cercospora spp. (including C. arachidicola), Cercosporidium personatum, Cladosporium spp., Claviceps spp.,

[0398] Coccidioides immitis, Corynespora cassiicola, Cryptendoxifium spp., Colletotrichum spp. (including C. musae),

[0399] Cryptococcus neoformans, Diaporthe spp., Didymella spp., Drechslera spp., Elsinoe spp.,

[0400] Epicoccum spp., Erysiphe spp. (including E. cichoracearum),

[0401] Eutypa lata, Fusarium spp. (including F. decemcellulare, F. graminearum, F. langsethii, F. moniliforme, F. solani, F. sulcatum, F. oxysporum, F. proliferatum), Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium mmusarum, Glomerella cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Herptora, Hemileccia, Histoplasma spp. (including H. capsulatum), Hymenochaete, Hymenochaete rubiginosa, Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochium nivale, Microsporum spp., Monilinia spp., Mucor spp., Mycosphaerella spp. (including M. graminicola, M. pomi), Mycosphaerella spp., Mycosphaerella destruens, Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaerella spp., Mycosphaoryzae), Pythium (including Pythium ultimosa), Pythium, Rhizobium, Rhizomucor pusillus, Rhizobium spp., Rhizosporium, Hyphomycetes (including Schizothyrium spp. and Schizothyrium spp.), Schizothyrium pomi.

[0402] Species of the genera *Sclerotium*, *Sclerotium*, *Syndrome* (including *S. noodorum* and *S. tritici*), *Sphaerotheca macularis* (fungal mildew fungus), *Sphaerotheca fusca* (cucumber powdery mildew fungus), *Sporothorix*, *Stagonospora nodorum*, *Stemphylium spp*, *Stereum hirsutum*, *Thanatephorus cucumeris* (rice blight fungus), *Thielaviopsis basicola*, *Smutella*, and *Trichoderma* (including *Trichoderma harzianum*, *Trichoderma konjac*, and *Trichoderma viride*).

[0403] Trichophyton species, sclerotium species, clematis species, stilago species, sclerotium species (including *V. inaequalis*), verticillium species, and xanthomonas species.

[0404] In particular, compounds having formula (I) as defined in this invention and fungicidal compositions containing them can be used to control plant diseases caused by a broad spectrum of fungal plant pathogens belonging to the Basidiomycetes, Ascomycetes, Oomycetes and / or Deuteromycetes, Blasocladiomycete, Chytridiomycete, Glomeromycete and / or Mucoromycete classes. More particularly, compounds having formula (I) as defined in this invention can be used to control Oomycetes.

[0405] These pathogens may include:

[0406] Oomycetes, including Phytophthora diseases such as those caused by P. capsici, P. infestans, P. sojae, P. fragariae, P. nicotianae, P. cinnamomi, P. citricola, P. citrophthora, and P. erythroseptica; Pythium diseases such as those caused by P. aphanidermatum, P. arrhenomanes, P. gramineum, P. irregulare, P. sylvaticum, and P. ultimum; diseases caused by Peronosporales such as P. destructor, P. brassicae, P. viticola, P. siliginica, P. cucurbitacearum, A. candida, P. oryzae, and Bremia lactucae; and others such as Spongospora subterranea, Labyrinthula zosterae, Peronosclerospora sorghi, and Sclerospora graminicola.

[0407] Ascomycetes, including blight, spot, blight or wilt and / or rot diseases, for example those caused by species of the order Pleosporales such as Stemphylium solani, Stagonospora atananensis, Cycloconium oleagineum, Setosphaeria turcica, Pyrenochaeta lycoperisici, Cytospora mandshurica, Phoma destructiva, Phaeosphaeria herpotrichoides, Phaeocryptocus gaeumannii, Ophiosphaerella graminicola, Ophiobolus graminis, Leptosphaeria maculans, Hendersonia creberrima, Helminthosporium triticirepentis, Setosphaeria turcica, Drechslera glycines, Didymella bryoniae, Cycloconium oleagineum, Corynespora cassiicola, Pyrenochaeta lycopersici, Bipolaris cactivora, Venturia inaequalis, Pyrenochaeta robusta, Pyrenophora tritici-repentis, Alternaria alternata, Alternaria brassicicola, Alternaria solani and Alternaria tomatophila;Capnodiales such as Septoria tritici, S. nodorum, S. glycines, Cercospora arachidicola, Cercospora sojae, Cercospora zeae-maydis, Cercosporella capsellae and Cercosporella herpotrichoides, Cladosporium carpophilum, Cladosporium effusum, Passalora fulva, Cladosporium oxysporum, Dothistroma septosporum, Isariopsis clavispora, Mycosphaerella fijiensis, Mycosphaerella graminicola, Mycovellosiella koepkeii, Phaeoisariopsis bataticola, Pseudocercospora vitis, Pyrenophora tritici-repentis, Ramularia betae, Ramularia collo-cygni; Diaporthales such as Pyrenochaeta lycopersici, Magnaporthe grisea, Pyricularia oryzae; Diaporthales such as Apiognomonia errabunda, Cytospora platani, Diaporthe phaseolorum var. sojae, Discula destructiva, Gnomonia fructicola, Glomerella cingulata, Melanconium juglandinum, Phomopsis viticola, Sirococcus clavigignenti-juglandacearum, Tubakia dryina, Dicarpella spp., Valsa ceratosperma;and others, such as Actinothyrium graminis, Ascochyta pisi, Aspergillus flavus, Aspergillus fumigatus, Aspergillus nidulans, Colletotrichum gloeosporioides, Blumeriella jaapii, Candida spp., Capnodium ramosum, Cephaloascus spp., Cephalosporium gramineum, Ceratocystis paradoxa, Chaetomium spp., Hymenoscyphus pseudoalbidus, Microsporum spp., Cylindrosporium padi, Diplocarpon malae, Drepanopezia brassicae; z a cam p*Estris*, *Elsinoe ampelina*, *Epiphyton floccosum*, *Epidermophyton* species, grape top blight, *Geotrichum candida*, *Gibellina cerealis*, *Gloeocercospora sorghi*, *Gloeodes pomigena*, *Gloeosporium perennans*; endophytic fungi of dead wheat (Gloeotinia temulenta), *Griphospaeria corticola*, *Kabatiella lini*, *Leptographium microsporum*, *Leptosphaerulinia crassiasca*, *Lophodermium seditiosum*, *Marssonina graminicola*, *Microdochium nivale*, *Monilinia* (Australian type of brown rot fungus of stone fruit). fructicola), rice cloud disease (Monographella albescens), melon black spot root rot fungus (Monosporascus cannonballus), species of the genus *Naemacyclus* spp., new elm wilt fungus (Ophiostoma novo-ulmi), *Paracoccidioides brasiliensis*, *Penicillium expansum*, *Pestalotia rhododendri*, species of the genus *Petriellidium* spp., species of the genus *Pezicula* spp., soybean stem brown rot fungus (Phialophora gregata), pome fruit black spot fungus (Phyllachorapomigena), omnivorous hornworm (Phymatotrichum omnivora), cryptocystis (Physalospora abdita), tobacco cyst shell (Plectosporium) *Taccacinum*, *Polyscytalumpustulans*, *Pseudopezi* z a medicaginis), Pyrenopezi z*Rhamnus abrassicae*, *Ramulispora sorghi*, *Rhabdoclinepseudotsugae*, *Rhynchosporium secalis*, *Sacrocladium oryzae*, *Scedosporium spp.*, *Schizothorax* zothyrium pomi), Sclerotinia sclerotiorum, Sclerotinia minor; Sclerotium spp., Typhula ishikariensis, Seimatosporium mariae, Lepteutypa cupressi, Septocytaruborum, Sphaceloma perseae, Sporonema phacidioides, Stigmina palmivora, Tapesia yallundae, Taphrina bullata, Thielviopsis basicola, Trichoseptoria fructigena, Zygophiala jamaicensis; powdery mildews, for example caused by the order Erysiphales, such as Blumeria graminis, Erysiphe cichoracearum, Uncinula necator, Sphaerotheca fuligena, Microsphaera diffusa, Podospaera macularis, Golovinomyces cichoracearum, Leveillula taurica, Uncinula dispersa, Oidiopsis gossypii, Phyllactinia guttata and Oidium arachidis;Mildews, for example those caused by Botryosphaeria species such as Dothiorella aromatica, Diplodia seriata, Guignardia bidwellii, Botrytis cinerea, Botryotinia allii, Botryotinia fabae, Fusicoccum amygdali, Lasiodiplodia theobromae, Macrophoma theicola, Ascochyta phaseolorum, Phyllosticta cucurbitacearum; anthracnoses, for example those caused by Glommerelales such as Colletotrichum acutatum, C. lagenarium, C. gossypii, C. fructigenum, and C. graminicola; and wilts or blights, for example those caused by the order Mortalies such as Stagonospora curtisii, Mycosphaerella pinodes, Fusarium culmorum, F. graminearum, F. virguliforme, F. oxysporum, F. oxysporum f. sp. cubense, Gerlachia nivale, Gibberella fujikuroi, Gliocladium species, Myrothecium verrucaria, Nectria ramulariae, Trichoderma virens, Podospora fimriata, and Verticillium theobromae.

[0408] Basidiomycetes, including smuts such as those caused by Ustilaginales, e.g. Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, Ustilago zeae, rusts such as those caused by Pucciniales, e.g. Cerotelium fici, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, Puccinia graminis, Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia striiformis f. sp. Hordei, Puccinia striiformis f. sp. Secalis, Pucciniastrum coryli; or Cronartium ribicola, Gymnosporangium juniperi-viginianae, Melampsora medusae, Phakopsora pachyrhizi zi) those caused by Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor, and Uromyces viciae-fabae; and other rots and diseases such as those caused by Cryptococcus spp., Guignardia bidwellii, Marasmiellus inoderma, Mycena spp., Sphacelotheca reiliana, Typhula ishikariensis, Urocystis agropyri, Itersonilia perplexans, Corticium invisum, Laetisaria fuciformis, Waitea circinata, Rhizoctonia solani, Thanetephorus cucurmeris, Entyloma dahliae, Entylomella microspora, Neovossia moliniae, and Tilletia caries.

[0409] Blastocladiomycetes, such as Physoderma maydis.

[0410] Mucoromycetes, such as Choanephora cucurbitarum; Mucor spp.; Rhizidomyces.

[0411] along with diseases caused by other species and genera closely related to those listed above.

[0412] In addition to their fungicidal activity, these compounds and compositions comprising a compound of Formula (I) as defined in the present application can also have activity against bacteria such as Erwinia amylovora, Erwinia caratovora, Xanthomonas campestris, Pseudomonas syringae, Strptomyces scabies and other related species, and certain protozoa.

[0413] Within the scope of the present application, the target crops and / or useful plants to be protected typically include perennial and annual crops, such as berry plants, for example blackberry, blueberry, cranberry, raspberry, and strawberry; cereals, for example barley, maize (corn), millet, oats, rice, rye, sorghum, triticale, and wheat; fiber plants, for example cotton, flax, hemp, jute, and sisal; field crops, for example sugar and fodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugarcane, sunflower, tea, and tobacco; fruit trees, for example apple, apricot, avocado, banana, cherry, citrus tree, nectarine, peach, pear, and plum; grass, for example Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St. Augustine grass, and Zoysia grass; herbs, for example basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage, and thyme; legumes, for example bean, lentil, pea, and soybean; nuts, for example almond, cashew, groundnut, hazelnut, peanut, pecan, pistachio, and walnut; palm plants, for example oil palm; ornamental plants, for example flowers, shrubs, and trees; other trees, for example cacao tree, coconut palm, olive tree, and rubber tree; vegetables, for example asparagus, aubergine, broccoli, cabbage, carrot, cucumber, garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach, and tomato; and vines, for example grapevine.

[0414] The useful plants and / or target crops according to the present application include conventional as well as genetically enhanced or genetically engineered varieties, such as for example insect-resistant (e.g. Bt. and VIP varieties) as well as disease-resistant, herbicide-tolerant (e.g. corn varieties that are tolerant to glyphosate and glufosinate ammonium under the trade names Round and Pioneer® and LibertyLink® (commercially available)) and nematode-resistant varieties. By way of example, suitable genetically enhanced or genetically engineered crop varieties include the Stoneville 5599BR cotton and Stoneville 4892BR cotton varieties.

[0415] The terms "useful plants" and / or "target crops" are to be understood as including useful plants that, as a result of genetic engineering, are made resistant to herbicides (such as bromoxynil) or classes of herbicides (for example, such as HPPD inhibitors, ALS inhibitors, for example primisulfuron, prosulfuron and tritosulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional methods of breeding or genetic engineering. An example of a crop that has been made tolerant to imidazolinones (for example imazamox) by conventional methods of breeding (mutagenesis) is the Clearfield® rice variety CL 161 from RiceTec. Summer rapeseed (Canola). Examples of crops that have been genetically engineered to be resistant to herbicides or herbicides include glyphosate-resistant and glufosinate-resistant maize varieties, marketed under the trade name... and Available for commercial purchase.

[0416] The terms “useful plant” and / or “target crop” should be understood to include those that are naturally or have been conditioned to be resistant to harmful insects. This includes plants transformed using recombinant DNA technology to, for example, synthesize one or more selectively acting toxins, as known from, for example, toxin-producing bacteria. Examples of toxins that can be expressed include δ-endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins from nematode-parasitic bacteria, and toxins produced by scorpions, arachnids, wasps, and fungi. An example of a crop modified to express Bacillus thuringiensis toxins is Btmaize. (Syngenta Seeds). Examples include crops that encode insecticidal resistance and thereby express more than one gene for more than one toxin. (Syngenta Seeds). Crops or their seed material can also be resistant to multiple types of pests (so-called superimposed transgenic events when produced through genetic modification). For example, plants can express insecticidal proteins while being resistant to herbicides, e.g. (Dow AgroSciences, Pioneer Hi-Bred International)

[0417] The terms “useful plant” and / or “target crop” should be understood to also include useful plants that have been transformed using recombinant DNA technology to synthesize selectively active resistance substances, such as so-called “pathogenic mechanism-associated proteins” (PRPs, see, for example, EP-A-0 392 225). Examples of such resistance substances and transgenic plants capable of synthesizing such resistance substances are known, for example, from EP-A-0 392 225, WO 95 / 33818, and EP-A-0 353 191. Methods for producing such transgenic plants are generally known to those skilled in the art and are described in, for example, the disclosures mentioned above.

[0418] Toxins expressible by the transgenic plant include, for example, insecticidal proteins from Bacillus cereus or Bacillus japonicas; or insecticidal proteins from Bacillus thuringiensis, such as delta-endotoxins, e.g., CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl or Cry9C, or vegetative insecticidal proteins (ViPs), e.g., Vip 1, Vip 2, Vip 3 or Vip 3 A; or insecticidal proteins from bacteria-plant nematode symbionts, such as Photorhabdus spp. or Xenorhabdus spp., e.g., Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, spider toxins, bee toxins and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea or barley lectins or snowdrop lectin; agglutinins; protease inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, cucurmosin, saporin or gelonin; steroid metabolism enzymes, such as 3-hydroxy-steroid oxidase, ecdysteroid-UDP-glucosyl-transferase, cholesterol oxidase, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers, such as blockers of sodium or calcium channels, juvenile hormone esterase, diuretic hormone receptors, stilben synthase, bibenzyl synthase, chitinases and glucanases.

[0419] Further, in the context of the present application, delta-endotoxins (e.g., CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl or Cry9C) or vegetative insecticidal proteins (ViPs) (e.g., Vip 1, Vip 2, Vip 3 or Vip 3 A) are to be understood as obviously also including hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are recombinantly produced by new combinations of different domains of those proteins (see, e.g., WO 02 / 15701 ). Truncated toxins, e.g., truncated CrylAb, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid replacements, it is preferred to insert into the toxin a non-naturally occurring protease recognition sequence, e.g., like in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into the Cry3A toxin (see WO 03 / 018810).

[0420] Further examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in EP-A-0 374 753, WO 93 / 07278, WO 95 / 34656, EP-A-0 427 529, EP-A-451 878 and WO 03 / 052073.

[0421] Methods for preparing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. Cry I type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90 / 13651.

[0422] The toxins comprised in the transgenic plants impart to the plants tolerance to harmful insects. Such insects can occur in any taxonomic group of insects, but are especially commonly found in beetles (Coleoptera), two-winged insects (Diptera) and moths (Lepidoptera).

[0423] Transgenic plants comprising one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of which are commercially available. Examples of such plants are: (zea mays variety, expressing CrylAb toxin); YieldGard (zea mays variety, expressing Cry3Bbl toxin); YieldGard (zea mays variety, expressing CrylAb and Cry3Bbl toxins); (zea mays variety, expressing Cry9C toxin); Herculex (zea mays variety, expressing CrylFa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) conferring tolerance to the herbicide glufosinate ammonium); NuCOTN (gossypium hirsutum variety, expressing CrylAc toxin); Bollgard (gossypium hirsutum variety, expressing CrylAc toxin); Bollgard (gossypium hirsutum variety, expressing CrylAc and Cry2Ab toxins); (gossypium hirsutum variety, expressing Vip3A and CrylAb toxins); (solanum tuberosum variety, expressing Cry3A toxin); GT Advantage (GA21 glyphosate-tolerance trait), CB Advantage (Btl 1 corn borer (CB) trait) and

[0424] Further examples of such transgenic crops are:

[0425] 1. Bt1 1 maize from Syngenta Seeds SAS, Chemindel'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize, by transgenic expression of a truncated CrylAb toxin, enabling resistance to attack by European corn borer (corn borer and pink stem borer). The Bt1 1 maize also transgenically expresses the PAT enzyme for tolerance to the herbicide glufosinate ammonium.

[0426] 2. Bt176 maize from Syngenta Seeds SAS, Chemindel'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize, by transgenic expression of a CrylAb toxin, enabling resistance to attack by European corn borer (corn borer and pink stem borer). The Bt176 maize also transgenically expresses the PAT enzyme for tolerance to the herbicide glufosinate ammonium.

[0427] 3. MIR604 maize from Syngenta Seeds SAS, Chemindel'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Maize with insect resistance by transgenic expression of a modified Cry3A toxin. This toxin is a Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The production of such transgenic maize plants is described in WO 03 / 018810.

[0428] 4. MON 863 maize from Monsanto Europe S.A., 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON 863 expresses a Cry3Bbl toxin and is resistant to certain Coleoptera insects.

[0429] 5. IPC 531 cotton from Monsanto Europe S.A., 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02.

[0430] 6. Zea mays from Pioneer Overseas Corporation, Avenue Tedesco, 7B-1 160 Brussels, Belgium, registration number C / NL / 00 / 10. Genetically modified maize expressing the protein Cry1 F for resistance to certain lepidopteran insects and the PAT protein for tolerance to the herbicide glufosinate ammonium.

[0431] 7. NK603 x MON 810 maize from Monsanto Europe S.A., 270-272 Avenue de Tervuren, B-1 150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. Composed of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810. NK603 x MON 810 maize genetically expresses the protein CP4 EPSPS obtained from Agrobacterium strain CP4, which confers tolerance to the herbicide Roundup® (containing glyphosate), and also expresses the Cry1 Ab toxin obtained from Bacillus thuringiensis subspecies kurstaki, which confers tolerance to certain lepidopteran insects, including European corn borer.

[0432] As used herein, the term "locus" means the place in which or on which the plant grows, or the place in which the seeds of the cultivated plants are sown, or the place in which the seeds are to be placed in the soil. It includes the soil, the seeds as well as the seedlings, together with the established vegetation.

[0433] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.

[0434] The term "plant propagation material" is to be understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the plant, and vegetative material, such as cuttings or tubers (e.g. potatoes). There can be mentioned, for example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, and parts of plants. Germinated plants and young plants which are to be transplanted after germination from the soil or after emergence from it, can also be mentioned. These young plants can be treated prior to transplantation by total or partial immersion. Preferably, "plant propagation material" is to be understood as meaning seeds.

[0435] The pesticides referred to herein using their common names are known, for example, from "The Pesticide Manual", 19th Edition, British Crop Protection Council 2021. ​

[0436] The compounds of formula (I) as defined by the present application can be used in unmodified form, or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end they can be conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations (for example in polymeric substances). The type of composition will depend on the intended purpose; the application method (spraying, atomizing, dusting, scattering, spreading, or pouring) and the prevailing circumstances. The compositions can also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders, or adhesion agents, together with fertilizers, micronutrient donors or other formulating agents for achieving special effects.

[0437] Suitable carriers and / or adjuvants, for example for agricultural use, can be solid or liquid and are substances intended to facilitate the application of a chemical to plants or to the locus of the plants, such as natural or regenerated mineral substances, solvents, dispersants, humectants, tackifiers, thickeners, binders or fertilizers. Such carriers are described, for example, in WO 97 / 33890.

[0438] Suspension concentrates are aqueous formulations in which finely divided solid particles of the active compound are suspended. Such formulations contain anti-settling agents and dispersants, and can further contain wetting agents to enhance activity, and antifoam and crystal growth inhibitors. At the time of use, these concentrates are diluted in water and are usually applied as a spray to the area to be treated. The amount of active ingredient can range from 0.5% to 95% of the concentrate.

[0439] Wettable powders are in the form of finely divided particles which disperse readily in water or other liquid carriers. The particles contain the active ingredient retained in a solid matrix. Typical solid matrices include fuller's earth, kaolin clays, silicas and other readily wet organic or inorganic solids. Wettable powders usually contain 5% to 95% of active ingredient plus small amounts of wetting, dispersing or emulsifying agents.

[0440] Emulsifiable concentrates are uniform liquid compositions which emulsify readily in water or other liquid carriers. They can consist entirely of active compound and liquid or solid emulsifying agents, or they can contain, in addition, a liquid carrier such as xylene, heavy aromatic petroleum, isophorone and other non-volatile organic solvents. At the time of use, these concentrates are emulsified in water or other liquid and usually applied as a spray to the area to be treated. The amount of active ingredient can range from 0.5% to 95% of the concentrate.

[0441] Granular formulations include both extrudates and coarser granules and are usually applied to the area to be treated without dilution. Typical carriers for granular formulations include sand, Fuller's earth, attapulgite clays, bentonite clays, montmorillonite clays, vermiculite, perlite, calcium carbonate, brick, pumice, smectite clays, dolomite, stucco, wood flour, ground corn cobs, ground peanut hulls, sugar, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesium oxide, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, ice crystals, gypsum, diatomaceous earth, calcium sulfate, and other organic or inorganic absorbent active compounds or materials that can be coated with active compounds. Granular formulations usually contain from 5% to 25% of the active ingredient, which can include surfactants such as heavy aromatic naphthalenes, kerosene and other petroleum fractions, or vegetable oils; and / or sticking agents such as dextrin, gum or synthetic resins.

[0442] Dusts are free-flowing mixtures of the active ingredient with finely divided solids such as talc, clays, flours, and other organic and inorganic solids which act as dispersing agents and carriers.

[0443] Microcapsules are typically microscopic droplets or particles of the active ingredient encased in an inert porous shell which allows the entrapped material to escape into the environment at a controlled rate. The diameter of the encapsulated droplets is typically 1 to 50 microns. The encapsulated liquid typically comprises 50% to 95% by weight of the capsule and can contain solvents in addition to the active compound. Encapsulated particles are usually porous particles in which a porous membrane seals the particle pores, retaining the active species in liquid form inside the particle pores. The diameter of the particles typically ranges from 1 millimeter to 1 centimeter and preferably 1 to 2 millimeters. The particles are formed by extrusion, coacervation or spheronization or are naturally occurring. Examples of such materials are vermiculite, sintered clay, kaolin, attapulgite clay, sawdust and carbon granules. Shell or membrane materials include natural and synthetic rubbers, fibrous materials, styrene-butadiene copolymers, polyacrylonitrile, polyacrylate, polyester, polyamide, polyurea, polyurethane and starch xanthate.

[0444] 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 the active ingredient is completely dissolved at the desired concentration. Pressurized sprays can also be used in which the active ingredient is dispersed in finely divided form as a result of evaporation of a low-boiling dispersant solvent carrier.

[0445] Suitable agricultural adjuvants and / or carriers useful in formulating the compositions of the present application in the above-mentioned formulation types are well known to those skilled in the art.

[0446] Liquid carriers that can be employed include, for example, water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, glycolic acid diethylene glycol ester, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, diproxitol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, alkyl pyrrolidinone, ethyl acetate, 2-ethyl hexanol, ethylene carbonate, 1,1,1-trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol diacetate, glycerol monocacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobutyl 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, octanoic acid, octyl, 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, isoprohyl alcohol, and higher molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexyl alcohol, octyl alcohol, etc., ethylene glycol, propylene glycol, glycerine, and N-methyl-2-pyrrolidinone. Water is generally the carrier of choice for diluting concentrates.

[0447] Suitable solid carriers include, for example, talc, titanium dioxide, smectite clays, silica, attapulgite clays, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, fuller's earth, cottonseed hulls, wheat middlings, soybean flour, pumice, wood flour, walnut shell flour, and lignin.

[0448] A wide range of surfactants can be advantageously employed in the liquid and solid compositions, especially those designed to be diluted with a carrier prior to application. These agents, when used, are generally present at 0.1% to 15% by weight of the formulation. They can be anionic, cationic, non-ionic or polymeric in nature and can be employed as emulsifying agents, wetting agents, suspending agents or for other purposes. Typical surfactants include alkyl sulfates such as diethanolammonium lauryl sulfate; alkyl aryl sulfonates such as calcium dodecyl benzene sulfonate; alkyl phenol-epoxyalkane addition products such as nonyl phenol-C.sub.18 ethoxylate; alcohol-epoxyalkane addition products such as tridecanol-C.sub.16 ethoxylate; soaps such as sodium stearate; alkyl naphthalene sulfonates such as sodium dibutylnaphthalene sulfonate; salts of dialkyl sulfosuccinates such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters such as sorbitol oleate; quaternary amines such as lauryl trimethylammonium 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 phosphates.

[0449] Other adjuvants commonly used in agricultural compositions include crystallization inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, de-foaming agents, light absorbers, compatibility agents, anti-foaming agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emulsifiers, lubricants, and sticking agents.

[0450] Further, still further, other biocidal active ingredients or compositions can be combined with the compositions of the present application, and used in the methods of the present application and applied simultaneously or sequentially with the compositions of the present application. When applied simultaneously, these additional active ingredients can be formulated or mixed together with the compositions of the present application, for example, in a spray tank. These additional biocidal active ingredients can be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides, plant growth regulators, and / or biological agents.

[0451] Preferred combinations of compounds of formula I with another active substance are the following combinations in a weight ratio of 1 : 1 (wherein the abbreviation "TX" means "one compound selected from the compounds defined in Tables 1.1 to 1.144 and Table A"):

[0452] (7E,9Z)-dodeca-7,9-dien-1-yl acetate + TX, (9Z,11E)-tetradeca-9,11-dien-1-yl acetate + TX, (9Z,12E)-tetradeca-9,12-dien-1-yl acetate + TX, (E)-6-methylhept-2-en-4-ol + TX, (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol + TX, (E)-tridec-4-en-1-yl acetate + TX, (E,Z)-tetradeca-4,10-dien-1-yl acetate + TX, (Z)-dodec-7-en-1-yl acetate + TX, (Z)-hexadeca-11-en-1-yl acetate + TX, (Z)-hexadec-11-enal + TX, (Z)-hexadec-13-en-11-yn-1-yl acetate + TX, (Z)-eicosa-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, 1,2-dibromo-3-chloropropane + TX, 1,2-dichloropropane + TX, 1,2-dichloropropane with 1,3-dichloropropene + TX, 1,3-dichloropropene + TX, 14-methyloctadeca-1-ene + TX, 1-hydroxy-1H-pyridine-2-thione + TX, 2-(octylthio)ethanol + TX, 2-chlorophenyl N-methylcarbamate (CPMC) + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 3,4-dichlorothiophene 1,1-dioxide + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide + TX, 4-methylnon-5-ol with 4-methylnon-5-one + TX, 5-methyl-6-thioxo-1,3,5-thiadiazin-3-yl acetate + TX, 6-isopentenylaminopurine + TX, 8-hydroxyquinoline sulfate + TX, abamectin + TX, acequinocyl + TX, acetamiprid + TX, acrinathrin + TX, acrinathrin + TX, acynonapyr + TX, adegothix GV + TX, afidopyropen + TX, afidopyropen + TX, afidopyropen + TX, agrobacterium radiobacter + TX, AKD-3088 + TX, aldicarb + TX, aldicarb + TX, aldicarb + TX, allethrin + TX, allethrin + TX, allethrin + TX, alpha-multistriatin + TX, amblyseius spp. + TX, amidoflumet + TX, amino acids + TX, anthial + TX, autographa californica npv + TX, anagasta kuehniella + TX, aphidoletes aphidimyza + TX, aphidius gossypii + TX, aphidius gossypii + TX, aphidius gossypii + TX, azadirachtin + TX, azadirachtin + TX, azadirachtin + TX, azadirachtin + TX, azadirachtin + TX, azadirachtin + TX,Bacillus chitinosporus AQ746 (NRRL Accession No. B-21618) + TX, Bacillus firmus + TX, Bacillus amyloliquefaciens Kurst. + TX, Bacillus mycoides AQ726 (NRRL Accession No. B-21664) + TX, Bacillus pumilus (NRRL Accession No. B-30087) + TX, Bacillus pumilus AQ717 (NRRL Accession No. B-21662) + TX, Bacillus sp. AQ175 (ATCC Accession No. 55608) + TX, Bacillus sp. AQ177 (ATCC Accession No. 55609) + TX, Bacillus sp. AQ178 (ATCC Accession No. 53522) + TX, Bacillus sphaericus + TX, Bacillus subtilis AQ153 (ATCC Accession No. 55614) + TX, Bacillus subtilis AQ30002 (NRRL Accession No. B-50421) + TX, Bacillus subtilis AQ30004 (NRRL Accession No. B-50455) + TX, Bacillus subtilis AQ713 (NRRL Accession No. B-21661) + TX, Bacillus subtilis AQ743 (NRRL Accession No. B-21665) + TX, Bacillus subtilis unspecified + TX, Bacillus thuringiensis AQ52 (NRRL Accession No. B-21619) + TX, Bacillus thuringiensis BD#32 (NRRL Accession No. B-21530) + TX, Bacillus thuringiensis + TX, Bacillus thuringiensis var. aizawai + TX, Bacillus thuringiensis var. israelensis + TX, Bacillus thuringiensis var. japonensis + TX, Bacillus thuringiensis var. kurstaki + TX, Bacillus thuringiensis var. tenebrionis + TX, Bacillus thuringiensis var. kurstaki BMP 123 + TX, Beauveria bassiana + TX, Beauveria brongniartii + TX, benzene chlorothion + TX, benomyl + TX, bensultap + TX, benzoxate + TX, benzoylurea + TX, beta-cyfluthrin + TX, beta-cypermethrin + TX, binxadin + TX, bifenazate + TX, bifenithrin + TX, binexate + TX, bioallethrin + TX, bioresmethrin + TX, bis (tri-butyl tin) oxide + TX, bisazir + TX, bistrifluron + TX, bis-CAS No. 1594624-87-9 + TX, CAS No. 1922957-47-8 + TX, CAS No. 1255091-74-7 + TX, CAS No. 1365070-72-9 + TX, CAS No. 1445683-71-5 + TX, CAS No. 1445684-82-1 + TX, CAS No. 1594626-19-3 + TX, CAS No. 1594637-65-6 + TX, CAS No. 1632218-00-8 + TX, CAS No. 1808115-49-2 + TX, CAS No. 1922957-46-7 + TX, CAS No. 1922957-48-9 + TX, CAS No. 1956329-03-5 + TX, CAS No. 1990457-52-7 + TX, CAS No. 1990457-55-0 + TX, CAS No. 1990457-57-2 + TX, CAS No. 1990457-66-3 + TX, CAS No. 1990457-77-6 + TX, CAS No. 1990457-85-6 + TX, CAS No. 2032403-97-5 + TX, CAS No. 2044701-44-0 + TX, CAS No. 2095470-94-1 + TX, CAS No. 2128706-04-5 + TX, CAS No. 2128706-05-6 + TX, CAS No. 2133042-31-4 + TX, CAS No. 2133042-44-9 + TX, CAS No. 2171099-09-3 + TX, CAS No. 2220132-55-6 + TX, CAS No. 2396747-83-2 + TX, CAS No. 2408220-91-5 + TX, CAS No. 2408220-94-8 + TX, CAS No. 2415706-16-8 + TX, Piperflanilide (CAS No. 2615135-05-0) + TX, CAS No. 2719848-60-7 + TX, CAS No. RNA (Spodoptera exigua-specific recombinant double-stranded interfering GS2) + TX, Chloethozylate + TX, Chlordane + TX, Chlorfenapyr + TX, Chloropicrin + TX, Chlorprifos + TX, Chromafenozide + TX, Chrysoperla carnea + TX, Clofentezine + TX, Cloethocarb + TX, Cryptolaemus montrouzieri + TX,Cuelure + TX, Cadanfos + TX, Cyantraniliprole + TX, Cybutryne + TX, Cyenopyrafen + TX, Cyclobutrifluram + TX, Pyrethrin + TX, Cycloxaprid + TX, Carpocapsa pomonella GV + TX, Clofentazine + TX, Cyetpyrafen + TX, Cyflumetofen + TX, Cyfluthrin + TX, Cyhalodiamide + TX, Cylohalothrin + TX, Cypermethrin + TX, Cyphenothrin + TX, Cyproflanilide + TX, Cyromazine + TX, Cytokinins + TX, Dacnusa sibirica + TX, Dazomet + TX, DBCP + TX, DCIP + TX, Deltamethrin + TX, Diafenthiuron + TX, Diamido + TX, Dibrom + TX, Dibutyl adipate + TX, Dibutyl phthalate + TX, Dibutyl succinate + TX, Dimefox + TX, Dicamba + TX, Diglyphus isaea + TX, Dimatif + TX, Dimethoate + TX, Dimethylcarbate + TX, Dimethyl phthalate + TX, Dimpropyridaz + TX, Diapocin + TX, Dinocap + TX, Dinotefuran + TX, Disulfoton + TX, Disulfito + TX, Disparlure + TX, D-limonene + TX, Dodec-8-en-1-yl acetate + TX, Dodec-9-en-1-yl acetate + TX, Dodec-8,10-dien-1-yl acetate + TX, Dothion + TX, Dominicalure + TX, Doramectin + TX, Emamectin + TX, Emamectin benzoate + TX, Etofenprox + TX, Encarsia + TX, Endothall + TX, Eprinomectin + TX, Epsilon-momfluorothrin + TX, Epsilon-methoxycarbonylfluorothrin + TX, Eretmocerus eremicus + TX, Esbiothrin + TX, Ethion + TX, Ethiprole + TX, Ethoprophos + TX, Ethyl 4-methyloctanoate + TX, Ethylhexanediol + TX, Ethylene dibromide + TX, Ethyl pyrethrum + TX, Etioxazine + TX,Seaweed extract and fermented products derived from glycoyl (including urea) + TX, seaweed extract and fermented plant products + TX, seaweed extract and fermented plant products (including plant hormones, vitamins, EDTA chelated copper, zinc, and iron) + TX, phosmet + TX, sodium dichloroisocyanurate + TX, fenamiphos + TX, quinalfen + TX, pendimethalin + TX, fenitrothion + TX, fenmezoditiaz + TX, methyl parathion + TX, fenthion + TX, fenthion +TX, Fenoxycarb +TX, Cypermethrin +TX, Fenpyrad +TX, Azoxystrobin +TX, Fusoxam +TX, Fenthion +TX, Triphenyltin +TX, Ethylmethrin +TX, Cypermethrin +TX, Ferrous Phosphate +TX, Fipronil +TX, Flumetoquin +TX, Flupyridine +TX, Pyrimethanil +TX, Trifluralin +TX, Acetamide +TX, Pyrimethanil +TX, Flufenoxuron +TX, Flufenoxuron +TX, Flufenoxuron +TX, Fluchlorfenapyr +TX, flucitrinate+TX, flufenoxuron+TX, flufenoxuron+TX, fluensulfone [318290-98-1]+TX, flufenoxuron+TX, pyrimethanil+TX, trifluralin+TX, fipronil+TX, fluhexafon+TX, flupyridamole+TX, flupyroxystrobin+TX, fluralaner+TX, lambda-cyhalothrin+TX, fluxametamide+TX, formaldehyde+TX, fosthiazate+TX, fosthietan+TX, frontalin+TX, furfural+TX, γ-cyhalothrin+TX (Z, E) and (Z, Z) isomers of (hexadeca-7, 11 -dien-1 -yl-acetate) 1 :1 mixture) + TX, grandlure + TX, grandlure I + TX, grandlure II + TX, grandlure III + TX, grandlure IV + TX, granulovirus + TX, gossyplure + TX, GY-81 + TX, halofenprox + TX, halofenozide + TX, harpin + TX, heliothis armigera nuclear polyhedrosis virus + TX, heliothis zea NPV + TX, heliothis zea nuclear polyhedrosis virus + TX, heliothis punctiger nuclear polyhedrosis virus + TX, heliothis virescens nuclear polyhedrosis virus + TX, hemel + TX, hempa + TX, heptamulid + TX, heptenophos + TX, heterorhabditis bacteriophora and H. megidis + TX, hexalure + TX, hexamide + TX, hexythiazox + TX, Hippodamia convergens + TX, hydramethylnon + TX, imidacloprid + TX, imiprothrin + TX, indazapyroxamet + TX, indoxacarb + TX, iodomethane + TX, iprodione + TX, ipsdienol + TX, ipsenol + TX, isamidofos + TX, isofenphos + TX, isocycloseram + TX, isoflualanam (CAS No.: 2892524-05-7) + TX, isoxathion + TX, ivermectin + TX, japonilure + TX, kappa-bifenthrin + TX, kappa-hexaflumuron + TX, kasugamycin + TX, kasugamycin hydrochloride hydrate + TX, kinetin + TX, lambda-cyhalothrin + TX, ledprona + TX, leptomycin + TX, Leptomastix dactylopii + TX, lineatin + TX, litlure + TX, looplure + TX, lotilaner + TX, lufenuron + TX, Macrolophus caliginosus + TX, mamestra brassicae NPV + TX, mecarphon + TX, medlure + TX, megatomoic acid + TX,cyromazine + TX, tetraalkyl orthoformate + TX, metam + TX, metam potassium salt + TX, metam sodium salt + TX, Metaphycus helvolus + TX, Metarhizium anisopliae var. acridum + TX, Metarhizium anisopliae var. anisopliae + TX, Metarhizium spp. + TX, metepa + TX, methiocarb + TX, methiotepa + TX, methomyl + TX, methoquin-butyl + TX, methoxyfenozide + TX, methyl apholate + TX, methyl bromide + TX, methyl eugenol + TX, methyl isothiocyanate + TX, methyl neodecanamide + TX, methoxychlor + TX, metolcarb + TX, metoxadiazone + TX, milbemycin oxime + TX, momfluorothrin + TX, morzid + TX, moxidine + TX, muscalure + TX, Muscodor albus 620 (NRRL Accession No. 30547) + TX, Muscodor roseus A3-5 (NRRL Accession No. 30548) + TX, Myrothecium verrucaria composition + TX, nabam + TX, NC-184 + TX, neem-based products + TX, Neodiprion sertifer NPV and N. lecontei NPV + TX, nickel bis(dimethyldithiocarbamate) + TX, niclosamide + TX, niclosamide-ethanolamine + TX, nicofluprole + TX, nitenpyram + TX, nitomate + TX, nitrapyrin + TX, orflalure + TX, Orthius spp. + TX, orytalure + TX, ostramone + TX, oxamate + TX, oxamyl + TX, oxazosulfyl + TX, oxolinic acid + TX, oxytetracycline + TX, Paecilomyces fumosa-ceus + TX, Paecilomyces lilacinus + TX, parathion-ethyl + TX, Paratrypa-nums strasserius + TX, Pasteuria penetrans + TX,Bacillus firmus + TX, Pasteuria penetrans + TX, Pasteuria ramosa + TX, Pasteuria thornei + TX, Bacillus thuringiensis + TX, p-cymene + TX, penfluron + TX, pentachlorophenol + TX, permethrin + TX, phenothrin + TX, phorate + TX, phosphamidon + TX, phosphocarb + TX, Phytoseiulus persimilis + TX, picarbutrazox + TX, pioxaniliprole + TX, piperazine + TX, piperonyl butoxide + TX, pirimicarb + TX, pirimiphos-ethyl + TX, pirimiphos-methyl + TX, plutella xylostella granulovirus + TX, plutella xylostella nuclear polyhedrosis virus + TX, polyhedrosis virus + TX, potassium and molybdenum and EDTA chelated manganese + TX, potassium ethyl xanthate + TX, potassium hydroxyquinoline sulfate + TX, propargite + TX, proquinazid + TX, profenofos + TX, profluralin + TX, propargite + TX, propetamphos + TX, propoxur + TX, prothiofos + TX, protrifenbute + TX, pyflubumide + TX, pymetrozine + TX, pyraclofos + TX, pyrafluprole + TX, pyrethrum + TX, pyridaben + TX, pyridalyl + TX, pyrifluquinazon + TX, pyriminostrobin + TX, pyriminostrobin + TX, pyridalyl [394730-71-3] + TX, pyridalyl + TX, pyriproxyfen + TX, QRD 420 (terpenoid blend) + TX, QRD 452 (terpenoid blend) + TX, QRD 460 (terpenoid blend) + TX, Quillaja saponaria + TX, quinoclamine + TX, quinonamid + TX, resmethrin + TX, Rhodococcus globerulus AQ 719 (NRRL Accession No. B-21663) + TX, sarolaner + TX, S-bioallethrin + TX, sebufos + TX, selamectin + TX, siglure + TX, silafluofen + TX, simazine + TX, sodium pentachlorophenol + TX, sordidin + TX, spidoxamat + TX, spinetoram + TX, spinosad + TX, spirobudifen + TX, spirodiclofen + TX, spiromesifen + TX, spiropidion + TX, spirotetramat + TX, Spodoptera exigua multicapsid nuclear polyhedrosis virus + TX,Spodoptera littoralis nuclear polyhedrosis virus + 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, Streptomyces galbus (NRRL Accession No. 30232) + TX, Streptomyces sp. (NRRL Accession No. B-30145) + TX, Streptomycin + TX, Streptomycin Bisulfate + TX, Strychnine + TX, sulcatol + TX, sulfiflumin (CAS No.: 2377084-09-6) + TX, sulfiram + TX, tazimcarb + TX, tebufenozide + TX, tebufenpyrad + TX, tebupirimiphos + TX, tecloftalam + TX, tefluthrin + TX, terbufos + TX, terpene blend + TX, tetrachlorantraniliprole + TX, tetrachlorothiophene + TX, tetradecan-11-en-1-yl acetate + TX, tetradiphon + TX, tetrachlorvinphos + TX, tetrachlorvinphos + TX, tetramethrin + TX, tetramethylfluthrin + TX, thiamethoxam + TX, theta-cypermethrin + TX, thiacloprid + TX, thiafenox + TX, thiamethoxam + TX, thiodicarb + TX, thiodicarb + TX, thiohempa + TX, thiomersal + TX, thiometon + TX, thiometon + TX, thionaz + TX, thiosultaphos + TX, thiosultaphos + TX, tigolaner + TX, tiorantraniliprole + TX, tioxazafen + TX, tolfenpyrad + TX, tolclofos-methyl + TX, tolfenpyrad + TX, tralomethrin + TX, transtetrachlor + TX, transfluthrin + TX, tralomethrin + TX, triazamate + TX, triazophos + TX, triazuron + TX, trichlorfon + TX, trichlorfon + TX, trichlorphon + TX, trichogramma spp. + TX, trifenmorph + TX,trifluenfuronate + TX, triflumezopyrim + TX, trimedlure + TX, trimedlure A + TX, trimedlure B1 + TX, trimedlure B2 + TX, trimedlure C + TX, trimethacarb + TX, tin

[0453] 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-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N- methyl-formamidine (these compounds can be prepared from the methods described in WO 2019 / 110427) + TX, (3',4',5'-trifluoro-biphenyl-2-yl)-amide + TX, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone (these compounds can be prepared from the methods described in WO 2017 / 220485) + TX, 2-amino-6-methyl-pyridine-3-carboxylic acid (4-phenoxy-phenyl)-methyl ester (this compound can be prepared from the methods described in WO 2014 / 006945) + TX, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate + TX, (9Z,11E)-tetradeca-9,11-dien-1-yl acetate + TX, (9Z,12E)-tetradeca-9,12-dien-1-yl acetate + TX, (E)-6-methylhept-2-en-4-ol + TX, (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol + TX, (E)-tridec-4-en-1-yl acetate + TX, (E,Z)-tetradeca-4,10-dien-1-yl acetate + TX, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, (Z)-dodeca-7-en-1-yl acetate + TX, (Z)-hexadeca-11-en-1-yl acetate + TX, (Z)-hexadeca-11-enal + TX, (Z)-hexadeca-13-en-11-yn-1-yl acetate + TX, (Z)-eica-13-en-10-one + TX, (Z)-tetradeca-7-en-1-al + TX, (Z)-tetradeca-9-en-1-ol + TX, (Z)-tetradeca-9-en-1-yl acetate + TX, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamine (this compound can be prepared from the methods described in WO 2018 / 153707) + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamine + 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, 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, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl- isoquinoline + TX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline (these compounds can be prepared from the methods described in WO 2017 / 025510) + TX, 1,1-bis(4- chlorophenyl)-2-ethoxyethanol + TX, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane + TX, 1,2-dibromo-3- chloropropane + TX, 1,2-dichloropropane with 1,3-dichloropropene + TX, 1,3-dichloropropene + TX, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one + TX, 10-dien-1-yl acetate + TX, 14-methyloctadeca-1-ene + TX, 1-bromo-2-chloroethane + TX, 1- dichloro-1-nitroethane + TX, 1-hydroxy-1H-pyridine-2-thione + TX, 1-methoxy-3-methyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 1-methyl-4-[3-methyl-2-[[2- methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one + TX, 2- (difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N- ((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate + TX, 2-(2-butoxyethoxy)ethyl piperate + TX, 2-(2-butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenylmethylcarbamate + TX, 2-(4-chloro-3,5-dimethylphenoxy)ethanol + TX,2-(difluoromethyl)-N-(3-ethyl-1,1 -dimethyl-indan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1 -dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1 -dimethyl-indan-4-yl]pyridine-3-carboxamide (this compound can be prepared from the method described in WO 2014 / 095675) + TX, 2-(difluoromethyl)-N-[3-ethyl-1,1 -dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, 2-(octylthio)ethanol + TX, 2,2,2-trichloro-1 -(3,4-dichlorophenyl)ethyl acetate + TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methylphosphonate + TX, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX, 2,4-dichlorophenyl phenylsulfonate + TX, 2,6-dimethyl-1 H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone (this compound can be prepared from the method described in WO 2011 / 138281 ) + TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol + TX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1 -(1,2,4-triazol-1 -yl)propan-2-ol (this compound can be prepared from the method described in WO 2017 / 029179) + TX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1 -(1,2,4-triazol-1 -yl)propan-2-ol (this compound can be prepared from the method described in WO 2017 / 029179) + TX, 2-chlorovinyl diethyl phosphonate + TX, 2-fluoro-N-methyl-N-1 -naphthaleneacetamide + TX, 2-imidazolinone + TX, 2-isovalerylindan-1,3-dione + TX, 2-methyl(prop-2-ynyl)aminophenylmethylcarbamate + TX, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide (this compound can be prepared from the method described in WO 2018 / 065414) + TX, 2-thiocyanatoethyl laurate + TX, 3-(4,4-difluoro-3,3-dimethyl-1 -isoquinolinyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole (these compounds can be prepared from the method described in WO 2016 / 156085) + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1 -yl)quinolone + TX, 3-(4-chlorophenyl)-5-methyl rhodanine + TX,3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide + TX, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound can be prepared from the method described in WO 2016 / 156290) + TX, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound can be prepared from the method described in WO 2016 / 156290) + TX, 3-bromo-1-chloroprop-1-ene + TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid + TX, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate + TX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide + TX, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline + TX, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)phenyl]-3-pyridyl]oxy]benzonitrile + TX, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + TX, 4-chlorophenyl phenyl sulfone + TX,4-methyl(prop-2-ynyl)amino-3,5-dimethylphenyl methylcarbamate + TX, 4-methylnon-5-ol and 4-methylnon-5-one + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone + TX, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, 5,5-dimethyl-3-oxocyclohex-1 -enyl dimethylcarbamate + TX, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1 ) + TX, 5-methyl-6-thioxo-1,3,5-thiadiazin-3-ylacetic acid + TX, 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (can be prepared from the method described in WO 2020 / 109391 ) + TX, 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (can be prepared from the method described in WO 2020 / 109391 ) + TX, 6-chloro-4,4-difluoro-3,3-dimethyl-1 -(4-methylbenzoimidazol-1 -yl)isoquinoline + TX, 6-chloro-N-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide (can be prepared from the method described in WO 2020 / 109391 ) + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile + TX, 6-isopentenylaminopurine + TX, 8-fluoro-N-[(1 R)-1 -[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, 8-fluoro-N-[(1 S)-1 -[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, 8-hydroxyquinoline sulfate + TX, acephate + TX, acetylcholine chloride + TX, acibenzolar + TX, acibenzolar-S-methyl + TX, acrylonitrile + TX, acyptolisiana GV + TX, agrobacterium radiobacter + TX, aldoxycarb + TX, aldrin + TX, aloi + TX, allosamycin + TX, allosamidin + TX, allosids + TX, alpha-chlorohydrin + TX, alpha-ecdysone + TX, alpha-multistriatin + TX, aluminium phosphide + TX, amblyseius spp. + TX, amectotractin + TX, ametoctradin + TX, amicarbalide + TX, amiton + TX,amino pyrifen + TX, aminopterin + TX, amitraz + TX, anabasine + TX, anagrapha falcifera NPV + TX, anagrus atomus + TX, ancymidol + TX, anilazine + TX, anisiflupurin + TX, anthraquinones + TX, antu + TX, aphelinus abdominalis + TX, aphelinus sericeus + TX, aphidoletes aphidimyza + TX, apholate + TX, aphidicolin + TX, arsenic trioxide + TX, athidathion + TX, autographa californica NPV + TX, azaconazole + TX, azamethiphos + TX, azobenzene + TX, azocyclotin + TX, azoxystrobin + TX, bacillus sphaericus neide + TX, bacillus thuringiensis delta-endotoxin + TX, barium carbonate + TX, barium hexafluorosilicate + TX, barium polysulfide + TX, benzoyl picolinic acid + TX, beaver 22 / 190 + TX, beaver 22408 + TX, beauveria brongniartii + TX, benalaxyl + TX, benclothiaz + TX, benomyl + TX, benoxafos + TX, benothiocarb + TX, benthiavalicarb + TX, benzbatacyl + TX, beta-fluorochlorocyclodiene + TX, beta-cyfluthrin + TX, bethoxazin + TX, bioethanomethrin + TX, bioresmethrin + TX, bis(2-chloroethyl)ether + TX, bis(tributyltin)oxide + TX, bisazir + TX, bistrifluron + TX, bitertanol + TX, bixafen + TX, boric acid + TX, borax + TX, boscalid + TX, brevicomin + TX, brodifacoum + TX, bromethrin + TX, bromo-Dipterex + TX, bromoform + TX, bromomethylcyclohexane + TX, bromophos + TX, bromoacetamide + TX, bromoethane + TX, bromo-DDT + TX, bromophos-ethyl + TX, bromopropylate + TX, bromoxynil + TX, buprofezin + TX, busulfan + TX, but-3-ynyl n-[6-[[(z)-[(1-methyltetrazol-5-yl)-phenyl-methylidene]amino]oxymethyl]-2-pyridinyl]carbamate + TX, butacarb + TX, butathiofos + TX, butocarboxim + TX, butonate + TX,Butopyronoxyl + TX, Butoxyl (polypropylene glycol) + TX, Butyl ketone sulfonate + TX, Butylpyridinium + TX, Calcium arsenate + TX, Calcium cyanide + TX, Calcium polysulfide + TX, Camphene octachlorophene + TX, Captan + TX, Carbendazim + TX, Chlorpyrifos + TX, Carbendazim + TX, Carbon disulfide + TX, Carbon tetrachloride + TX, Phosphate + TX, Carbofuran + TX, Bataan Hydrochloride + TX, CAS No.: 2132414-04-9 + TX, CA S-type: 2344721-61-3+TX, Veratrine+TX, Acaricide+TX, Chlorpyrifos+TX, Acaricide+TX, Borneol+TX, Chlordane+TX, Decachlorone+TX, Amitraz+TX, Amitraz Hydrochloride+TX, Dichlorvos+TX, Acaricide+TX, Ethyl Acetate+TX, Chloroform+TX, Chlorindolehydrazine+TX, Amitraz+TX, Diflubenzuron+TX, Dimethoate+TX, Chlorpyrifos+TX, Chlorothalonil+TX, Chloropicrin+TX, Propyl Acetate+TX Chlorothalonil + TX, chlorpyrifos + TX, chlorpyrifos + TX, chlorfenapyr + TX, ethoxysulfuron + TX, cholecalciferol + TX, common lacewing + TX, cismethrin I + TX, cis-resmethrin + TX, cypermethrin + TX, cloxacillin + TX, dodecadienol + TX, cypermethrin + TX, copper arsenite + TX, copper arsenate + TX Copper dioctanoate + TX, copper hydroxide + TX, copper naphthenate + TX, copper oleate + TX, copper oxide + TX, copper oxychloride + TX, copper sulfate + TX, chlorpyrifos + TX, chlorpyrifos + TX, phosmet + TX, naphthalene + TX, cypermethrin + TX, phosmet + TX, eugenol + TX, pyrimidine + TX, phosmet + TX, phosmet + TX, phosmet + TX, cryolite + TX, *Cryptospira moniliforme* + TX, CS 708+TX, Fly-attractant +TX, Thiazol +TX, Benzoate +TX, Mefenoxam +TX, Folic Acid +TX, Cyprodinil +TX, Cyclopyralid +TX, Pyrethrum +TX, Triflupyridamole +TX, Codling Moth GV +TX, Cycloflufenicol +TX, Acaricide +TX, Cymoxanil +TX, Cyclopyralid +TX, Cyclopyralid +TX, Cyclopyralid +TX, Cyclopyralid +TX, Cyclopyralid +TX, Cyclopyralid +TX, Siberian Parasitic Wasp +TX, DAEP +TX, Dazomet +TX, DCIP +TX, DCPM +TX, DDT +TX, Imazalil +TX, Demethylcarbofuran +TX, Tebuconazole +TX, Tebuconazole-O +TX, Tebuconazole-S +TX, Demeton-methyl +TX, Demeton-O +TX, Demeton-O-methyl +TX, Demeton-S +TX, Demeton-S-methyl +TXDemeton-S-methyl sulfon + TX, dinocap + TX, dibutyl adipate + TX, dibutyl phthalate + TX, dibutyl succinate + TX, dichlofenthion + TX, dichlorophenyl dimethyl urea + TX, dichlo- rothion + TX, dichlo- rothion + TX, dichlone + TX, dichlorophen + TX, dichlorvos + TX, dimetachlone + TX, di- chlorpyriphene + TX, di- chlorpyriphene + TX, ditalimfos + TX, diclomezni + TX, dithianon + TX, DNOC + TX, dodec-8-en-1-yl acetate + TX, dodec-9-en-1-yl acetate + TX, dodeca-8 + TX, dodemorph + TX, doglucide + TX, dodine + TX, domi- nocide + TX, domiphen + TX, doramectin + TX, DSP + TX, d-allethrin + TX, de- pside + TX, edifenphos + TX, EI 1642 + TX, EMPC + TX, encarsia formosa + TX, endo- sulfan + TX, endothion + TX, enox- folate + TX, enox- folate + TX, EPBP + TX, ep- roconazole + TX, ipconazole + TX, er- sila + TX, ergocalciferol + TX, etaphos + TX, ethaboxam + TX, etho- phenprox + TX, ethoxyfen + TX, ethyl 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro- prop-1-enyloxy]phenyl]methyl]pyrazole-3-carboxylate (can be prepared from the method described in WO 2020 / 056090) + TX,1-[[4-[[2-(trifluoromethyl)-1,3-dioxolane-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate (which can be prepared by the method described in WO 2020 / 056090) + TX, 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate + TX, 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate (which can be prepared by the method described in WO2018 / 158365) + TX, ethyl 4-methyloctanoate + TX, ethyl formate + TX, ethylhexanediol + TX, dibromoethane + TX, dichloroethane + TX, ethylene oxide + TX, tebuconazole + TX, ethirimol + TX, eugenol + TX, EXD + TX, oxadixyl + TX, farnesol + TX, farnesol with nerolidol + TX, imidacloprid + TX, sodium dichloroisocyanurate + TX, tebuconazole + TX, chlorpyrifos + TX, fenbutatin + TX, phosmet + TX, ethylcarbamide + TX, mefenoxam + TX, cyclophosphamide + TX, fenitrothion + TX, fenthiocarb + TX, oxypyrimethanil + TX, isoprothiolane + TX, mix The following are listed: pyraclostrobin + TX, benzyme + TX, pyrimethanil + TX, benzoyl + TX, pyridaben + TX, pyridaben + TX, pyridaben + TX, pyridaben + TX, fenthion + TX, ethyl fenthion + TX, triphenyltin + TX, flunitridinium + TX, ferric ammonium + TX, pyraclostrobin + TX, ferric phosphate + TX, fludioxonil + TX, diflubenzuron + TX, fluazinam + TX, fluazinam + TX, flufenoxuron + TX, flufenoxuron + TX, fludioxonil + TX, fludioxonil + TX. Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Fluinbazin + TX, Flusulfanilamide + TX, Flumorph + TX, Fluopyram + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, Flufenoxam + TX, FMC 1137+TX, Captan+TX, Formaldehyde+TX, Amitraz+TX, Amitraz Hydrochloride+TX, Ammonium Chloride+TX, Aluminum Tris(ethylphosphonate)+TX, Butylthion+TX, Phosphate-Arsenate+TX, Butylthion+TX, Southern Pine Bark Beetle Collector Pheromone+TX, Wheat-Earing Agent+TX, Furazolidone+TX, Furazolidone+TX, Pyrethrum+TX, Furfural+TX, γ-HCH+TX, Fruit Green Agent+TX, Inducing Agent Mixture+TX, Inducing Agent Mixture I+TXThe following are listed as examples of attractant mixtures: Isotrione Mixture II + TX, Isotrione Mixture III + TX, Isotrione Mixture IV + TX, Biguanide Octyl Salt + TX, Biguanide Octyl Acetate + TX, Benzylfentanyl + TX, HCH + TX, Hexamethylmelamine + TX, Hexamethylphos + TX, HEOD + TX, Heptachlor + TX, Phosphate + TX, Heterotrophic Acid (Heterorhabditis bacteriophora) and Hemibarbus megidis + TX, Hexaconazole + TX, Cetylcyclopropane Carboxylate + TX, Hexaconazole + TX, Hexafen + TX, HHDN + TX, Spotted Ladybug + TX, Mercaptan + TX, Quicklime + TX, Hydrogen Cyanide + TX, Hymexazol + TX, Quinoline + TX, Imanin + TX, Imazalil + TX, Imidazole + TX, Biguanide Octylamine + TX, Indazol + TX, Smecta + TX, Isothiazinon + TX Isopropylquinoline + TX, Isoprothiolane + TX, Iprodione + TX, Propineb + ​​TX, Tebufenozide + TX, Tebufenozide + TX, IPSP + TX, Isamidophos + TX, Chlorpyrifos + TX, Carbochlor + TX, Methamidophos + TX, Isaldrin + TX, Isofenphos + TX, Isopropylthiophanate + TX, Isopropylfluopyram + TX, Transplanting Agent + TX, Isoprothiolane + TX, Pyraclostrobin + TX, Isofenphos + TX, Oxadiazon + TX, Scarab Beetle Sex Toner + TX, Jasminyl I+TX, Jasmine Chloride II+TX, Iodine Thiophanate +TX, Juvenile Hormone I+TX, Juvenile Hormone II+TX, Juvenile Hormone III+TX, Thiamethoxam +TX, Kasugamycin +TX, Kasugamycin Hydrochloride Hydrate +TX, Chloramphenicol +TX, Kinetin +TX, Acetaminophen +TX, Azoxystrobin +TX, Lead Arsenate +TX, Citrus citrus scale parasitic wasp +TX, Bromophenylphos +TX, Lindane +TX, Trimethyldioxane-nonane +TX, Acetaminophen +TX, Noctuid moth pheromone +TX, Powdery mildew Noctuid moth pheromone + TX, lvbenmixianan + TX, thiamethoxam + TX, mirid bug + TX, magnesium phosphide + TX, propiconazole + TX, cabbage noctuid moth NPV + TX, mancozeb + TX, mancozeb + TX, mandespin + TX, dimethomorph + TX, mancozeb + TX, azidophos + TX, m-isopropylphenyl methyl carbamate + TX, phosmet + TX, methyl phosmet + TX, phosmet + TX, chlorfluazuron + TX, megatomoic acid acid)+TX, phosmet+TX, pyraclostrobin+TX, chlorpyrifos+TX, dithiamethoxam+TX, methamidophos+TX, mercuric oxide+TX, mercurous chloride+TX, methifenol+TX, methyl sulfoxide+TX, metalaxyl+TX, thiamethoxam+TX, thiamethoxam potassium salt+TX, thiamethoxam sodium salt+TX, yellow-spotted flea +TX, yellow-green metamillinomyces+TX, Metarhizium anisopliae microsporum variety of beetle +TX, pyridaben+TX, tebuconazole+TX, methyl thiophanate+TX, chlorfenapyr+TXMethylsulfonyl fluoride + TX, Sobufos + TX, Methiocarb + TX, Butenachlor + TX, Methoprene + TX, Methoxyfenozide + TX, Methojarath + TX, Methoxychlor + TX, (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2- enoic acid methyl ester + TX, (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy- prop-2-enoic acid methyl ester (these compounds can be prepared by the methods described in WO 2020 / 193387) + TX, (Z)-2-[5-(3-isopropylpyrazol-1-yl)-2-methyl- phenoxy]-3-methoxy-prop-2-enoic acid methyl ester + TX, (Z)-3-methoxy-2-[2-methyl- 5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoic acid methyl ester + TX, (Z)-3-methoxy- 2-[2-methyl-5-(4-propyltriazol-2-yl)phenoxy]prop-2-enoic acid methyl ester + TX, (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2- enoic acid methyl ester (these compounds can be prepared by the methods described in WO 2020 / 079111) + TX, (Z)-3-methoxy-2-[2-methyl-5-[4- (trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoic acid methyl ester + TX, Methoxam + TX, Bromomethane + TX, Methoprene + TX, Methyl isothiocyanate + TX, N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl] carbamic acid methyl ester (can be prepared by the methods described in WO 2020 / 097012) + TX, N-[[4-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl] carbamic acid methyl ester (can be prepared by the methods described in WO 2020 / 097012) + TX, N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamic acid methyl ester + TX, Methyl chloroform + TX, Dichloromethane + TX, Methyl neodecanamide + TX, Metiram + TX, Metolcarb + TX, Metrafenone + TX, Metiram + TX, MGK 264 + TX, Milbemycin oxime + TX, Propamocarb + TX, Mirex + TX, Monocrotyl + TX, Moxyde + TX, Muscalure + TX, Myclobutanil + TX, Myclobutanil + TX, Myrothecium verrucaria composition + TX, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide (these compounds can be prepared by the methods described in WO 2017 / 153380) + TX,N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide (these compounds can be prepared from the methods described in WO 2017 / 153380) + TX, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine (these compounds can be prepared from the methods described in WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348 and WO 2017 / 118689) + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-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-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared from the methods described in WO 2016 / 202742) + TX, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-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-isopropyl-N-methyl-formamidine (these compounds can be prepared from the methods described in WO 2015 / 155075) + TX, N'-[5-bromo-2-methyl-6-(2- propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared from the methods described in IPCOM000249876D) + TX, N'-[5-bromo-2-methyl-6- [(1 R)-1 -methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-[(1 S)-1 -methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N- methyl-formamidine + TX, N'-[5-chloro-2-methyl-6-(1 -methyl-2-propoxy-ethoxy)-3- pyridyl]-N-ethyl-N-methyl-formamidine + TX, N-[N-methoxy-C-methyl-carboximidoyl]-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (these compounds can be prepared from the methods described in WO 2018 / 202428) + TX, N'-[4-(1 - cyclopropyl-2,2,2-trifluoro-1 -hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N- methyl-formamidine (these compounds can be prepared from the methods described in WO 2018 / 228896) + TX, Nabami + TX, Naugard® + TX, Naugard® P + TX, Naugard® S + TX, Naphthalene + TX, NC-170 + TX, Neodiprion sertifer NPV and N. lecontei NPV + TX, Nerolidol + TX, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl] propanamide + TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]- N-methyl-formamidine + TX, Nickel bis(dimethyldithiocarbamate) + TX, Nitroscanate- ethanolamine + TX, Nicotine + TX, Nicotine sulfate + TX, Mirex + TX, Nikcomycin + TX, N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1 -hydroxy-1 -phenyl-ethyl)phenyl]- N-methyl-formamidine + TX, Nitrofenpyramide + TX, Picolinafen + TX,N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide + TX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide + TX, brodifacoum + TX, difenacoum + TX, fenthion + TX, O,O,O',O'-tetrapropyl dithiophosphorothioic acid + TX, octadeca-2,13-dien-1-yl acetate + TX, octadeca-3,13-dien-1-yl acetate + TX, octhilinone + TX, furametpyr + TX, oleic acid + TX, omethoate + TX, hecogenin + TX, cryptolestes spp. + TX, dinoderes punctatus aggregation pheromone + TX, famoxadone + TX, fenamidone + TX, fosetyl + TX, fosetyl-aluminum + TX, iprobenfos + TX, oxine-copper + TX, oxolinic acid + TX, oxycarboxin + TX, isofenphos + TX, phosphamidon + TX, terramycin + TX, paclobutrazol + TX, paecilomyces fumosoroseus + TX, p-dichlorobenzene + TX, parathion + TX, methyl-parathion + TX, pefurazoate + TX, penconazole + TX, pencycuron + TX, penthiopyrad + TX, phenthoate + TX, phorate + TX, phosalone + TX, phosmet + TX, phorate + TX, phosphamidon + TX, phosphine + TX, phosphorus + TX, profenofos + TX, prothioconazole + TX, prothiofos + TX, pyaclofos + TX, pydiflumetofen + TX, pyrimethanil + TX, pyrithiobac-sodium + TX, pyriproxyfen + TX, pyroxychlor + TX, pyroxyfur + TX, chilean small eriophyid mite + TX, pyracarbolid + TX, pyrametostrobin + TX, pyraclostrobin + TX, pyrametostrobin + TX, pyrametostrobin + TX, pyridalyl + TX,Fluazinam + TX, Phenthoate + TX, Pyrid-4-amine + TX, Pyridaben + TX, Pyrimethanil + TX, Pyrimithanate + TX, Pyrimorph + TX, Rodex + TX, Spicamone + TX, Spirodiclofen + TX, Spiroxamine + TX, Quassoid extract + TX, Quinothion + TX, Quinothion-methyl + TX, Quinoclamine + TX, Quinoxyfen + TX, Quinoxyfen + TX, Quintozene + TX, R-1492 + TX, Rafoxanide + TX, Reserpisone + TX, Reynoutria extract + TX, Ribavirin + TX, R-metamidophos + TX, Rotenone + TX, Rostiline + TX, S421 + TX, Sabacon + TX, Soman + TX, Squarine + TX, Sinitrin + TX, Spinosad + TX, Spinotoram + TX, Spirofam + TX, Sirexan + TX, Sisaline + TX, SI-0009 + TX, Sirexan + TX, Simazine + TX, Silthiofam + TX, Sodium arsenite + TX, Sodium cyanide + TX, Sodium fluoride + TX, Sodium fluoroacetate + TX, Sodium hexafluorosilicate + TX, Sodium pentachlorophenol + TX, Sodium selenate + TX, Sodium tetrathio-carbonate + TX, Sodium thiocyanate + TX, Sulfotep + TX, Banana borer attractant + TX, Spirofam + TX, SSI-121 + TX, Steinermona + TX, Compana + TX, Heliothis + TX, Gladiolus + TX, Rhabditis + TX, Steinernema riobravis + TX, Scutigerella + TX, Steinernema spp. + TX, Streptomycin + TX, Streptomycin sesquisulfate + TX, Strophantin + TX, Sirexan + TX, Sulfallat + TX, Sulfallat sodium salt + TX, Sulfluramid + TX, Sulfofpic + TX, Sulfoxide + TX, Sulfur + TX, Sulfuryl fluoride + TX, Sulfotep + TX, Tar + TX, Tau-fluvalinate + TX, Tetradifon + TX, Teflubenzuron + TX, Terbufos + TX, Tetrachloroethane + TX, Tetrachlorothiophene + TX, Tefluthrin + TX, Tetradecan-11-en-1-yl acetate + TX, Tetrasul + TX, Tetramethrin + TX, Thallium sulfate + TX, Thiabendazole + TX, Thiafenox + TX, Thiofanox + TX, Thiocarboxime + TX, Thiocloprid + TX, Thiocyano + TX, Thiodicarb + TX, Thiodicarb + TX, Thiometon + TX, Thiometon + TX, Thionex + TX,Methyl phorate + TX, chlorpyrifos + TX, thiophanate-methyl + TX, methyl thiophanate + TX, chlorpyrifos + TX, chlorpyrifos + TX, chlorpyrifos sodium + TX, thiophanate-methyl + TX, siloxane + TX, thiamethoxam + TX, methyl thiophanate + TX, trifluralin + TX, parathion + TX, tetrabromopropylate + TX, permethrin + TX, tratamethrin + TX, triadimefon + TX, triadimefon + TX, phosmet + TX Benfenthiamethoxam + TX, Azoxystrobin + TX, Triazophos + TX, Imidazin + TX, Azoxystrobin + TX, Tributyltin oxide + TX, Isofenphos-3 + TX, Phosphorus + TX, Trichogramma spp. + TX, Chlorpyrifos + TX, Tricyclazole + TX, Tridemorph + TX, Snailicide + TX, Trichloropropoxyphos + TX, Azoxystrobin + TX, Fluopyram + TX, Azoxystrobin + TX, Mediterranean fruit fly attractant + TX, Mediterranean fruit fly attractant A+ TX, Mediterranean fruit fly attractant B1+TX, Mediterranean fruit fly attractant B2+TX, Mediterranean fruit fly attractant C+TX, mixed carbendazim+TX, thiophanate-methyl+TX, anti-rot ester+TX, triphenyltin acetate+TX, triphenyltin hydroxide+TX, tebufenozide+TX, cypermethrin+TX, methylphenidate+TX, trunc-call+TX, Western mirid mite+TX, urethaneimine+TX, effectivemycin+TX, valafenamide+TX, aphid-killing agent+TX , including: fipronil + TX, veratrine + TX, veratrine + TX, synergistic alkyne + TX, Verticillium clade + TX, ethylene sclerotinia + TX, rodenticide + TX, XMC + TX, xylenol + TX, zeatin + TX, zetamethrin + TX, kasugamycin + TX, zinc naphthenate + TX, zinc phosphide + TX, zinc thiamethoxam + TX, zineb + ​​TX, thiram + TX; , oxadiazon + TX;

[0454] Acinetobacter rumeni + TX, Acremonium spp. + TX, Acremonium diospyri + TX, Acremonium obclavatum + TX, AdoxGV (cotton brown belt moth granulovirus). +TX, Agrobacterium radioactive strain K84 +TX, Alternaria +TX, Alternaria cassia +TX, Damaged Alternaria +TX, powdery parasitic spores +TX, Aspergillus AF36 +TX, Aspergillus flavus NRRL 21882 +TX, Aspergillus species +TX, Budding Brachyphorus +TX, Azospirillum genus +TX, nitrogen-fixing bacteria +TX, brown coccidia +TX, Bionatural Blooming +TX, Bacillus amyloliquefaciens +TX, Bacillus cereus +TX, Bacillus chitinosporus strain AQ746 +TX, Bacillus chitinosporus strain CM-1 +TX, Bacillus circulans +TX, Bacillus firmus In particular strain CNMC1-1582 (e.g. from BASF SE, under the trade name +TX, Bacillus licheniformis strain 3086 +TX, Bacillus licheniformis strain HB-2 (Biostart TM formerly known as +TX, Bacillus lentimorbus +TX, Bacillus maroccanus +TX, Bacillus megaterium +TX, Bacillus mycoides strain AQ726 +TX, Bacillus naoshenyensis (Milky Spore +TX, Bacillus pumilus sp. +TX, Bacillus pumilus strain AQ717 +TX, Bacillus pumilus strain GB34 (Yield +TX, Bacillus pumilus strain QST 2808 Ballad +TX, Bacillus sphaericus +TX, Bacillus sp. +TX, Bacillus strain AQ175 +TX, Bacillus strain AQ177 +TX, Bacillus strain AQ178 +TX, Bacillus subtilis strain AQ153 +TX, Bacillus subtilis strain AQ743 +TX, Bacillus subtilis strain QST 713 +TX, Bacillus subtilis strain QST 714 +TX, Bacillus subtilis strain QST3002 +TX, Bacillus subtilis strain QST3004 +TX, Bacillus subtilis var. amyloliquefaciens strain FZB24 +TX, Bacillus thuringiensis aizawai GC 91 +TX, Bacillus thuringiensis Cry 2Ae +TX, Bacillus thuringiensis CrylAb +TX, Bacillus thuringiensis israelensis +TX, Bacillus thuringiensis kurstaki (Dipel®) Scutella Turilav Dipel +TX, Bacillus thuringiensis kurstaki BMP 123 +TX, Bacillus thuringiensis kurstaki HD-1 +TX, Bacillus thuringiensis strain AQ52 +TX, Bacillus thuringiensis strain BD#32 +TX, Bacillus thuringiensis galleriae BtBooster) +TX, Bacillus thuringiensis var. kurstaki +TX, Bacteroides sp. +TX, Bacteriophage of Clavipacter michiganensis +TX, Beauveria bassiana Brocaril ) +TX, Beauveria bassiana GHA (Mycotrol Mycotrol ) +TX, Beauveria brongniartii Schweizer ) +TX, Beauveria sp. +TX, Botrytis cinerea +TX, Bradyrhizobium japonicum +TX, Brevibacillus brevis +TX, Burkholderia cenocepacia Blue ) +TX, Burkholderia sp. +TX, Burkholderia gladioli +TX, Burkholderia sp. +TX, Canadian thistle fungus (CBH Canadian ) +TX, Candida kefyr +TX, Candida paronychia +TX, Candida fructus +TX, Candida glabrata +TX, Candida guilliermondii +TX, Candida +TX, Candida sake +TX, Candida sp. +TX, Candida tenuis +TX, Cedecea davisae +TX, Cellulomonas flavidus +TX, Chaetomium atroviride +TX, Chaetomium globosum +TX, Calodococcus tsugae strain PRAA4-1T +TX, Cladosporium cladosporioides +TX, Cladosporium cladosporioides +TX, Cladosporium oxysporum +TX, Cladosporium sp. +TX, Cladosporium tenuissimum +TX, Clonostachys rosea +TX, Colletotrichum acutatum +TX, Sphaeropsis ) +TX, Sphaeropsis sp. +TX, Cryptococcus albidus + TX, Cryptococcus neoformans + TX, Cryptococcus infirmo-miniatus + TX, Cryptococcus laurentii + TX, Grapholita funebrana gran- tiviruses + TX, Cupriavidus campinensis + TX, Cydia pomonella gran- tiviruses Plus, Madex Max, + TX, Cylindrobasidium laeve + TX, Drebachia + TX, Debaryomyces hansenii + TX, Drechslera hawaiinensis + TX, Enterobacter cloacae + TX, Enterobacteriaceae + TX, Entomophthora virulenta + TX, Epicoccum + TX, Epicoccum nigrum + TX, Epicoccum sp. + TX, Filobasidium floriforme + TX, Fusarium acuminatum + TX, Fusarium sporotrichioides + TX, Fusarium oxysporum Biofox ) + TX, Fusarium proliferatum + TX, Fusarium sp. + TX, Geotrichum candidum + TX, Gliocephalum catenatum + TX, Gliocephalum roseum + TX, Gliocephalum sp. + TX, Gliocephalum viride + TX, Granulovirus + TX, Halobacterium halophilum + TX, Halobacterium halophilum + TX, Halobacterium thalpium + TX, Halomonas sp. + TX, Halomonas subglaciescola + TX, Halovibrio variabilis + TX, Hanseniaspora uvarum + TX, Helicoverpa armigera nuclear polyhedrosis virus + TX, Helicoverpa zea nuclear polyhedrosis virus + TX, Isaria fumosorosea (formerly Paecilomyces fumosa- roseus strain, ) + TX, Isoflavone formononetin + TX, Kloeckera apiculata + TX, Kloeckera sp. + TX, Leptolegnia caudata + TX, Lecanicillium lecanii (formerly Verticillium lecanii strain KV01 (e.g. Mycotal® by Koppert / Arysta) ) Verticillium lecanii Conidia + TX, Lecanicillium longisporum + TX, Lecanicillium muscarium + TX, Lymantria dispar nucleopolyhedrovirus + TX, M. halophila + TX, M. grisea + TX, Destruxin + TX, Destruxin + TX, Metschnikowia fruticola + TX, M. pulcherrima + TX, Microdochium dimerum + TX, Micromonospora coerulea + TX, Microsphaeropsis ochracea + TX, Muscodor albus 620 + TX, Muscodor roseus, especially strain A3-5 (Accession No. NRRL 30548) + TX, Myccorrhapha sp. Root + TX, Myrothecium verrucaria strain AARC-0255 BROS + TX, Ophiostoma piliferum strain D97 + TX, Paecilomyces variotii + TX, Paecilomyces lilacinus strain 251 (MeloCon + TX, Paecilomyces lilacinus (Biostat + TX, Paenibacillus polymyxa + TX, Pantoea agglomerans (BlightBan + TX, Pantoea sp. + TX, Pseudomonas synxantha, especially strain Pn1 (CLARIVA from Syngenta / ChemChina) + TX, Pasteuria sp. + TX, Penicillium chrysogenum + TX, Penicillium breyi + TX, Penicillium brevicompactum + TX, Penicillium frequentans + TX, Penicillium canescens + TX, Penicillium purpurogenum + TX, Penicillium sp. + TX, Phlebiopsis gigantea + TX, Resupinatus + TX, Phosphate solubilizing bacteria + TX, Phytophthora cryptogea + TX, Phytophthora palmivora + TX, Pseudomonas aeruginosa + TX, Pseudomonas aureofasciens (Spot-Less )+ TX, Pseudomonas cepacia + TX, Pseudomonas chlororaphis )+ TX, Pseudomonas corrugate + TX, Pseudomonas fluorescens )+ TX, Pseudomonas fluorescens strain A506 (Blight Ban )+ TX, Pseudomonas putida + TX, Pseudomonas reactans + TX, Pseudomonas spp. + TX, Pseudomonas syringae )+ TX, Pseudomonas viridiflava + TX, Pseudozyma flocculosa strain PF-A22 UL (Sporodex )+ TX, Puccinia canaliculata + TX, Puccinia thlaspeos (Wood )+ TX, Pythium paroecandrum + TX, Pythium oligandrum )+ TX, Pythium periplocum + TX, Rhanella aquatilis + TX, Rhanella spp. + TX, Rhizobia +TX, Rhizoctonia +TX, Rhodococcus globerulus strain AQ719 +TX, Rhodosporidium diobovatum +TX, Rhodosporidium toruloides +TX, Rhodotorula glutinis +TX, Rhodotorula graminis +TX, Rhodotorula mucilagnosa +TX, Rhodotorula rubra +TX, Rhodotorula spp. +TX, Saccharomyces cerevisiae +TX, Salinococcus roseus +TX, Sclerotium spp. +TX, Sclerotiniaminor +TX, Scytalidium spp. +TX, Scytalidium uredinicola +TX, Serratia marcescens +TX, Serratia plymuthica +TX, Serratia spp. +TX, Sordaria fimicola +TX, Beet armyworm nucleopolyhedrovirus +TX, Spodopteralittoralis nucleopolyhedrovirus (Sea Grey-winged Noctuid Moth) +TX, Sporobolomyces roseus +TX, Stenotrophomonas maltophilia +TX, Streptomyces albaduncus +TX, Streptomyces exfoliates +TX, Streptomyces galbus +TX, Streptomyces griseoplanus +TX, Streptomyces griseoviridis +TX, Streptomyces hygroscopicus +TX, Streptomyces lydicus +TX, Streptomyces lydicus WYEC-108 +TX, Streptomyces violaceus +TX, Tilletiopsis minor +TX, Tilletiopsis spp. +TX, Trichoderma asperellum (T34 )+TX, Trichoderma atroviride +TX, Trichoderma gamsii +TX, Trichoderma hamatum TH 382 +TX, Trichoderma harzianum rifai +TX, Trichoderma harzianum T-22 PlantShield )+TX, Trichoderma harzianum T-39 +TX, Trichoderma inhamatum +TX, Trichoderma koningii +TX, Trichoderma lignorum +TX, Trichoderma longibrachiatum +TX, Trichoderma polysporum (Binab )+TX, Trichoderma spp. LC 52 +TX, Trichoderma taxi +TX, Trichoderma virens (formerly known as Gliocladium virens GL-21) +TX, Trichoderma virens +TX, Trichoderma viride +TX, Trichoderma viride strain ICC 080 +TX, *Trichosporon pullulans* +TX, *Trichosporon* spp. +TX, *Trichothecium roseum* +TX, *Trichothecium* spp. +TX, *Typhula phacorrhiza* strain 94670 +TX, *Typhula phacorrhiza* strain 94671 +TX, *Ulocladium atrum* +TX, *Ulocladium oudemansii* +TX, Ustilago maydis (corn smut), various bacteria and supplements (Natural) )+TX, various fungi (Millennium) )+TX, Verticillium chlamydosporium+TX, Vip3Aa20 +TX, *Virgibaclillus marismortui* +TX, *Xanthomonas campestris* pv. Poae +TX, Burkholderia bronchiseptica +TX, Nematophyte pathogens +TX;

[0455] MMF+TX, Plasma Neem For example, AZATIN XL+TX from Certis, USA, and plant-based IGR +TX、 +TX, canola oil (Lilly Miller) )+TX, Chenopodium ambrosioides near ambrosioides +TX, chrysanthemum extract +TX, Labiatae essential oil +TX, Neem oil extract +TX, clove-rosemary-peppermint and thyme oil extracts (Garden insect) )+TX, garlic+TX, betaine +TX, Kaolin +TX, lemongrass oil + TX, Melaleuca alternifolia extract (also known as tea tree oil) (Timorex + TX, Syzygium-mentha-garlic oil and mint mixture (Soil + TX, Syzygium-rosemary and peppermint extract mixture (EF + TX, Rosemary-sesame-peppermint-thyme and cinnamon extract mixture (EF + TX, Neem oil + TX, Catnip (Nepeta cataria) (catnip oil) + TX, Nepeta catarina + TX, Nicotine + TX, Oregano oil + TX, Pedaliaceae oil + TX, Pine oil + TX, Pyrethrum + TX, Quillaja saponaria + TX, Giant knotweed + TX, Rotenone (Eco + TX, Rutaceae plant extract + TX, Soybean oil (Ortho + TX, Storage glucan of brown algae + TX, Thyme oil + TX;

[0456] (E,Z)-7,9-dodecadien-1-yl acetate + TX, (E,Z,Z)-3,8,11 tetradecatrienyl acetate + TX, (Z,Z,E)-7,11,13-hexadecatrienal + TX, 2-methyl-1-butanol + TX, + TX, Blackheaded fireworm pheromone (3M Sprayable Blackheaded Fireworm + TX, Calcium acetate + TX, + TX, Codling moth pheromone (Paramount dispenser-(CM) / Isomate + TX, Entostat powder (extract from palm trees) (Exosex + TX, Grape berry moth pheromone (3M MEC-GBM Sprayable + TX, Lavender thymol + TX, Looper moth pheromone (3M MEC-LR Sprayable + TX, Housefly pheromone (Snip7 Fly +TX, oriental fruit moth sprayable pheromone (3M )+TX, Peachtree Borer pheromone +TX, +TX, Starbar Premium Fly )+TX, Tomato Pinworm pheromone (3M Sprayable )+TX;

[0457] Acerophagus papaya +TX, Two-spotted ladybird +TX, Two-spotted ladybird +TX, Two-spotted ladybird +TX, Telenomus remus +TX, Telenomus tritoli +TX, Andersonius australis +TX, Amblyseius Californicus +TX, Amblyseius cucumeris Bugline )+TX, Amblyseius pseudolongispinosus +TX, Amblyseius strawsoni (Bugline )+TX, Amblyseius ovalis +TX, Coccobius fulvus +TX, Comperflia salicis +TX, Cremnopsida obscuripennis +TX, Cremnopsida kamali +TX, Anagyrus loecki +TX, Coccobius fulvus +TX, Coccobius sinicus +TX, Chrysopa perla +TX, Anthocoris nemoralis +TX, Aprostocetus coquilletii +TX, Aprostocetus stigmater +TX, Aphidius gifuensis +TX, Aphidius gifuensis +TX, Aphidius uzbekicus +TX, Aphidius rosae +TX, Bactrocera cucurbitae +TX, Coccobius fulvus +TX, Coccobius fulvus +TX, Cremnopsida obscuripennis +TX, Cremnopsida kamali +TX, Anagyrus loecki +TX, Coccobius fulvus +TX, Bombus spp. +TX, Bombus terrestris +TX, Bombus terrestris (Natupol )+TX, Cephalonomia stephanoderis +TX, Cheilomenes sexmaculata +TX, Chrysopa communis + TX, Telenomus remus + TX, Telenomus sp. + TX, Telenomus tarsalis + TX, Tetrastichus galleruccii + TX, Tetrastichus sp. + TX, Tetrastichus + TX, Tetrastichus sp. + TX, Tetrastichus trichopterorum + TX, Tetrastichus trichopterorum + TX, Tetrastichus trichopterorum + TX, Tetrastichus trichopterorum + TX, Tetrastichus trichopterorum + TX, Tetrastichus trichopterorum Eretmocerus + TX, Tetrastichus trichopterorum + TX, Tetrastichus trichopterorum + TX, Tetrastichus trichopterorum + TX, Tetrastichus trichopterorum + TX, Tetrastichus trichopterorum + TX, Tetrastichus trichopterorum + TX, Tetrastichus trichopterorum + TX, Tetrastichus trichopterorum BioNem Exhibitline + TX, Tetrastichus trichopterorum )+TX, Spotted Ladybug +TX, Stenoptera stenoptera mite +TX, Hypoline )+TX, Black Gall Beetle +TX, Lecanoideus floccissimus +TX, Lemophagus errabundus +TX, Tricolor Jumping Wasp +TX, Orange Scale Parasitic Wasp +TX, Longhorn Jumping Wasp +TX, Lindorus lophanthae +TX, Lipolexis oregmae +TX, Forked Leaf Greenfly +TX, Tea-footed Aphid Parasitic Wasp +TX, Mirid Bug ( Macroline )+TX, Mesoseiulus longipes+TX, Yellow broad-stalked jumping wasp+TX, Metaphycus lounsburyi+TX, horned-veined brown lacewing +TX, Yellow Flower-winged Jumping Bee +TX, Muscidifuraxraptorellus and Spalangia cameroni +TX, Neodryinus typhlocybae+TX, Neoseido Seymite caecalii+TX, Neoseido Seymite cucumeris +TX, pseudo-new small seimitium +TX, Nesideocoristenuis +TX, Bronze Black Fly +TX、The Cunning Little Flower Bug ( Oriline )+TX, hairless small flower bug (Orius laevigatus) ( Oriline +TX, Oriline (a type of flower bug) +TX, Black Flower Stink Bug +TX, Pauesia juniperorum+TX, Ladybug stalk wasp+TX, Phasmarhabditis hermaphrodita +TX, Phymastichus coffea+TX, Physeieus coarse-haired +TX, Physeieus hilaris ( Phytoline )+TX, Spotted Belly-Stinging Beneficial Bug + TX, parasitic midge Curvotaenia curvatus + TX, parasitic midge Curvotaenia obtusus + TX, parasitic midge Curvotaenia tricuspis + TX, Pseudaphycus maculipennis + TX, Pseudleptomastix mexicana + TX, Tamarixia dryi + TX, Cotesia flavipes (complex) + TX, Telenomus sp. + TX, Rhyzobius lophanthae + TX, Rodolia australasiae + TX, Rumina decollate + TX, Semielacher petiolatus + TX, Sitobion avenae + TX, Steinerema carpocapsae (Nematac BioNem ) + TX, Steinerema scirpiperda (Nemasys Nemasys BioNem Exhibitline ) + TX, Xylechinema pilosum (Nemasys BioNem Exhibitline ) + TX, Xiphinema index + TX, Steinerema gryllium (Nematac ) + TX, Steinerema sp. + TX, Steinernema sp. (Guardian ) + TX, Cheyletus eruditus + TX, Leptomastix mubaraki + TX, Tetrastichus setifer + TX, Thripobius semiluteus + TX, Torymus sinensis + TX, Trichogramma brassicae ) + TX, Trichogramma brassicae + TX, Trichogramma chilonis + TX, Trichogramma minutum + TX, Trichogramma nubilale + TX, Trichogramma platneri + TX, Trichogramma pretiosum + TX, Telenomus sp. + TX, Telenomus sp. (Telenomicid

[0458] Abscisic acid + TX, + TX, + TX, + TX, CAS No.: 2643947-26-4 + TX, Chondrostereum purpureum (Chontrol ) + TX, Discula annulata + TX, Copper octanoate +TX, Delta trap (Trapline) )+TX, Erwinia amyloliquefaciens (Harpin) Ni-HIBIT Gold )+TX, fatty acids derived from natural byproducts of extra virgin olive oil +TX, Ferric Phosphate +TX, Funnel trap (Trapline) )+TX、 +TX、Grower's +TX, Homo-brassonolide, ferric phosphate (Lilly Miller Worry Free Ferramol Slug & Snail) +TX, MCP hail trap (Trapline) )+TX, parasitic insects, Southern food beetle (Microctonus hyperodae)+TX, Mycoleptodiscus terrestris +TX, Semaspore Organic Grasshopper +TX, Thripline (Pheromone Network) )+TX, potassium bicarbonate +TX, potassium iodide + potassium thiocyanate +TX, potassium salts of fatty acids +TX, potassium silicate solution +TX, Spider Venom +TX, Trapline Rebell )+TX、 +TX, Capture (Takitrapline y+) )+TX;

[0459] Mojave Bacillus strain R3B (accession number NCAIM(P)B001389)(WO2013 / 034938)+TX from Certis USA, a small spore-forming bacterium, particularly strain BU F-33, with NRRL accession number 50185 (from BASF). Bacillus subtilis strain D747 (from Kumiai Chemical Industry Co., Ltd. as DOUBLE NEMASEEK® Bacillus subtilis strain BU1814 (from BASF SE as RHAPSODUS® PLUS, FLEX and EXTRA) + TX, Bacillus amyloliquefaciens var. strain FZB24 with registration number DSM 10271 (from Novozymes as RHAPSODUS® or ECO available (EPA registration number 70127-5)) + TX, Bacillus subtilis, in particular strain QST713 / AQ713 (with NRRL registration number B-21661 and described in U.S. Patent No. 6,060,051 from Bayer CropScience LP as SERENADE® OPTI or ASO available) + TX, Paenibacillus polymyxa, in particular strain AC-1 (for example from Green Biotech Company Ltd. as BIOLOGICAL ) + TX, Paenibacillus sp. strain with registration number NRRL B-50972 or registration number NRRL B-67129, WO 2016 / 154297 + TX, Pantoea agglomerans, in particular strain E325 (registration number NRRL B-21856) (from Northwest Agri Products as BLOOMTIME BIOLOGICAL TM FDBIOPESTICIDE available) + TX, Pseudomonas proradix (for example from Sourcon Padena as ) + TX;

[0460] Aureobasidium pullulans, in particular blastospores of strain DSM14940, blastospores of strain DSM 14941 or a mixture of blastospores of strain DSM14940 and DSM14941 (for example from bio-ferm, Switzerland as and BLOSSOM ) + TX, Pseudozyma aphidis (as disclosed in WO 2011 / 151819 by Yissum Research Development Company, Jerusalem Hebrew University) + TX, Saccharomyces cerevisiae, in particular strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938 or CNCM No. 1-3939 from Lesaffre et Compagnie (WO 2010 / 086790) + TX;

[0461] Agrobacterium radiobacter strain K84 (e.g. from AgBioChem, California, USA ) + TX, Bacillus amyloliquefaciens isolate B246 (e.g. from AVOGREEN, University of Pretoria TM ) + TX, Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL Accession No. B-50768, WO 2014 / 028521) (from Marrone BioInnovations ) + TX, Bacillus amyloliquefaciens strain FZB42, Accession No. DSM 23117 (available from ABiTEP, Germany, under the trade name Rhizogreen® available) + TX, Bacillus amyloliquefaciens, in particular strain D747 (available from Double Nickel, a Division of Chem-I-Corp under the trade name TM available, having Accession No. FERM BP-8234, US Patent No. 7,094,592) + TX, Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (from FMC Corporation under the trade name (WG) and (WP) + TX, Bacillus licheniformis, in particular strain SB3086, having Accession No. ATCC 55406, WO 2003 / 000051 (from Novozymes under the trade name Biofungicide and GREEN RELEAF TMAvailable)+TX, Bacillus methylotrophicus strain BAC-9912 (from Chinese Academy of Sciences’ Institute of Applied Ecology) +TX, Bacillus mycoides, isolate, having Accession No. B-30890 (from Certis USA under the trade name or WG and LifeGard TM Available)+TX, Bacillus pumilus, particularly strain GB34 (from Bayer CropScience AG, Germany under the trade name Available)+TX, Bacillus pumilus, particularly strain QST2808 (from Bayer CropScience, USA under the trade name Available, having Accession No. NRRL B-30087 and described in U.S. Patent No. 6,245,551)+TX, Bacillus subtilis CX-9060 from Certis USA+TX, Bacillus subtilis IAB / BS03 (from AVIV of STK Bio-Ag Technologies TM from Idai Nature )+TX, Bacillus subtilis KTSB strain (from Donaghys )+TX, Bacillus subtilis strain BU1814, (from BASF SE under the trade name PLUS, FLEX and EXTRA Available)+TX, Bacillus subtilis strain GB03 (from Bayer CropScience AG, Germany under the trade name Available)+TX, Bacillus subtilis strain MBI 600 (from BASF SE under the trade name SUBTILEX Available), having Accession No. NRRL B-50595, U.S. Patent No. 5,061,495+TX, Bacillus subtilis strain Y1336 (from Bion-Tech, Taiwan under the trade name WP Available, registered in Taiwan, China as a biofungicide under Accession Nos. 4764, 5454, 5096 and 5277)+TX, Bacillus subtilis var. amyloliquefaciens strain FZB24, having Accession No. DSM 10271 (from Novozymes under the trade name or ECO Available (EPA Reg. No. 70127-5))+TX, Bacillus subtilis Y1336 (from Bion-Tech, Taiwan under the trade name WP available as a biofungicide registered in Taiwan, China under registration numbers 4764, 5454, 5096 and 5277) + TX, Clavibacter spp. from BASF SE (WO 2016 / 020371) + TX, Paenibacillus polymyxa plant species from BASF SE (WO 2016 / 020371) + TX, Paenibacillus sp. strain with registration number NRRL B-50972 or registration number NRRL B-67129, WO 2016 / 154297 + TX, Pseudomonas chlororaphis strain AFS009 with registration number NRRL B-50897, WO 2017 / 019448 (e.g., HOWLER TM and ) + TX, Pseudomonas chlororaphis, in particular strain MA342 (e.g., from Bioagri and Koppert and ) + TX, Pseudomonas fluorescens strain A506 (e.g., from NuFarm A506) + TX, Pseudomonas proradix (e.g., from Sourcon Padena ) + TX, Streptomyces griseoviridis strain K61 (also known as Streptomyces galbus strain K61) (registration number DSM 7206) (from Verdera from BioWorks see Crop Protection 2006, 25, 468-475) + TX, Streptomyces lydicus strain WYEC108 (also known as Streptomyces lydicus strain WYCD108US) (from Syngenta) and ) + TX;

[0462] Trichoderma atroviride strain T11 (IMI 352941 / CECT 20498) + TX, Isaria fumosorosea strain AQ10 with registration number CNCM 1-807 (e.g., AQ ) + TX, Isaria fumosorosea, in particular strain AQ 10 (e.g., AQ ) + TX, Aspergillus flavus strain NRRL 21882 (as Bio-Flux® from Syngenta / China National Chemical Corporation) Known products) +TX, budding short-stemmed molds, especially budding spores of strain DSM 14941 +TX, budding short-stemmed molds, especially budding spores of strain DSM 14940 +TX, budding short-stemmed molds, especially mixtures of budding spores of strains DSM 14940 and DSM 14941 (e.g., from Bio-Film, Switzerland) )+TX, Chaetomium cupreum (registration number CABI 353812) (e.g., BIOKUPRUM from AgriLife) TM )+TX, Chaetomium globosum (available from Rivale) Acquired) +TX, Cladosporium cladosporioides, strain H39, with accession number CBS122244, US2010 / 0291039 (by the Wageningen Research Foundation (Stichting Dienst Landbouwkundig Onderzoek)) +TX, scutellarin, especially strain CON / M / 91-8 (accession number DSM9660, e.g., from Bayer CropScience Biosciences). )+TX, Cryptococcus flavescens, strain 3C (NRRL Y-50378)+TX, Dactylaria candida, Dilophosphora alopecuri (can be TWIST) (Available from Natural Plant Protection), Fusarium oxysporum, strain Fo47 (Obtained) +TX, *Streptococcus pyrenoidospora* strain J1446 (e.g., from Lallemand). ) + TX, Clonostachys rosea (also known as Clonostachys rosea f. rosea) 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' [Particular emphasis on the near commercial fungal antagonist Clonostachys rosea strain 'IK726' for plant disease control with special emphasis on the near commercial fungal antagonist Clonostachys rosea strain 'IK726'], Australasian Plant Pathol. 2007, 36(2): 95-101) + TX, Clonostachys rosea, in particular strain 321U from Adjuvants Plus, strain ACM941 as disclosed in Xue A.G. (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root rot complex of field pea [Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root rot complex of field pea]), Can Jour Plant Sci 2003, 83(3): 519-524) + TX, Metschnikowia fructicola, in particular strain NRRL Y-30752 + TX, Microsphaeropsis ochracea, Penicillium steckii (DSM 27859, WO 2015 / 067800) from BASF SE + TX, Trichoderma asperellum strain ICC 012 (also known as T. harzianum ICC012) with registration number CABI CC IMI 392716 and Trichoderma gamsii (originally T. virens) strain ICC 080 with registration number IMI 392151 (e.g., BIO-TAM TM or from Agrobiosol de Mexico, S.A. de C.V. ) + TX, Penicillium vermiculatum + TX, Phlebiopsis gigantea strain VRA 1992 (from Danstar Ferment C) + TX, Pseudozyma flocculosa strain PF-A22 UL (available from Plant Products Co. in California under the trade name Mycoshield® L) + TX, Saccharomyces cerevisiae strain LAS117 cell wall (from Lesaffre from BASF SE is Mycostop® ) + TX, Saccharomyces cerevisiae strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938, CNCM No. 1-3939 from Lesaffre in France (WO 2010 / 086790) + TX, Saccharomyces cerevisiae, in particular strain LASO2 (from Agro-Levures et Derives) + TX, Simplicillium lanosoniveum + TX, strain T34 (e.g. T34 from Biocontrol Technologies S.L. in Spain) or strain ICC 012 from Isagro + TX, strain WRL-076 (NRRL Y-30842), U.S. Patent No. 7,579,183 + TX, Talaromyces flavus, strain V117b + TX, Trichoderma asperelloides JM41R (Accession No. NRRL B-50759) (TRICHO ) + TX, Trichoderma asperelloides, in particular strain SKT-1, with Accession No. FERM P-16510 (e.g. from Combi-chem Industries Co. in Japan) Trichoderma echinococcus, especially strain kd (e.g., T-Gro from Andermatt Biocontrol) +TX, Trichoderma viride strain 77B (T77 from Andermatt Biocontrol) +TX, Trichoderma viride strain ATCC 20476 (IMI 206040) +TX, Trichoderma viride strain LC52 (e.g., Tenet from Agrim Technologies Limited) +TX, Trichoderma viride strain LU132 (e.g., Sentinel from Agrim Technologies Limited) +TX, Trichoderma viride strain NMI V08 / 002388 +TX, Trichoderma viride strain NMI V08 / 002389 +TX, Trichoderma viride strain NMI V08 / 002390 +TX, Trichoderma viride strain V08 / 002387 +TX, Trichoderma viride strain SKT-1 (FERM) P-16510), Japanese Patent Application (Kokai) 11-253151A+TX, Trichoderma viride strain SKT-2 (FERM P-16511), Japanese Patent Application (Kokai) 11-253151A+TX, Trichoderma viride strain SKT-3 (FERM P-17021), Japanese Patent Application (Kokai) 11-253151A+TX, Trichoderma viride, especially strain SC1 (registration number CBS122089, WO 2009 / 116106 and US Patent No. 8,431,120 (from Bi-PA)+TX), Trichoderma viride, strain CNCM 1-1237 (e.g. from Agrauxine, France). WP)+TX, Trichoderma pygmyces (e.g., TrichoPlus from BASF)+TX, Trichoderma galbsiella (formerly Trichoderma viride)+TX, Trichoderma galbsiella (formerly Trichoderma viride) strain ICC 080 (IMI CC 392151CABI) (available from Agribilso Mexico) (Obtained) +TX, Trichoderma galbense strain ICC080 (IMI CC 392151CABI, e.g. BioDerma from Agriberso Mexico) +TX, Trichoderma harzianum +TX, Trichoderma harzianum with accession number ATCC 28012 +TX, Trichoderma harzianum +TX, Trichoderma harzianum rifai T39 (e.g. from Makhteshim, USA) )+TX, Trichoderma harzianum strain Cepa SimbT5 (from Simbiose Agro)+TX, Trichoderma harzianum strain DB 103 (available from Dagutat Biolab) 7456 obtained)+TX, Trichoderma harzianum strain ITEM 908 (e.g., Trianum-P from Koppert)+TX, Trichoderma harzianum strain T-22 (e.g., Trianum-P from Andermatt Biocontrol or Koppert)+TX, Trichoderma harzianum strain TH35 (e.g., Root-Pro from Mycontrol)+TX, Trichoderma multisporum strain IMI 206039 (e.g., Binab TF WP from BINAB Bio-Innovation AB, Sweden)+TX, Trichoderma stromatophora, with accession number Ts3550 (e.g., Tricovab from CEPLAC, Brazil)+TX, Trichoderma viride (also known as green broom mold) especially strain GL-21 (e.g., SoilGard from Sertis, USA)+TX, Trichoderma viride strain G-41, formerly known as green broom mold (accession number ATCC) 20906) (For example, from the US-based Byvo company) PLUS WP and

[0463] PLUS WP)+TX, Trichoderma viride, especially strain B35 (Pietr et al., 1993, Zesz.Nauk.AR wSzczecinie 161:125-137)+TX, Trichoderma viride strain TV1 (e.g., Trianum-P from Corbert)+TX, Ulocladium oudemansii strain U3, with accession number NM 99 / 06216 (e.g., from Botry-Zen Ltd, New Zealand) and from Baivo )+TX, Verticillium albo-atrum (formerly Verticillium dahliae) strain WCS850, with accession number WCS850, is deposited at the Fungal Culture Centre (e.g., from DUTCH, Tree Care Innovations). )+TX, Verticillium chlamydosporium +TX;

[0464] A mixture of brown azotocin and Clostridium pasteurellium (available from Agrinos) (Obtained) +TX, a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available from FMC Corporation) (WG) (WP) obtained)+TX, *Semen Sesamum indicum*, especially strain ZB-SK-5+TX, *Azotobacter brasiliensis* (e.g., from KALO). )+TX, lipogenic azospirobacteria (e.g., VERTEX-IF from TerraMax) TM +TX, azotobacters, especially strain H23 +TX, brown azotobacters, especially strain ATCC 12837 +TX, Bacillus amyloliquefaciens BS27 (accession number NRRL B-5015) +TX, Bacillus amyloliquefaciens, especially strain FZB42 (e.g., from Abitep GmbH, Germany) +TX, Bacillus amyloliquefaciens, especially strain IN937a+TX, Bacillus amyloliquefaciens pm414 (from Biofilm Crop Protection). )+TX, Bacillus amyloliquefaciens SB3281 (ATCC#PTA-7542, WO 2017 / 205258)+TX, Bacillus amyloliquefaciens TJ1000 (available from Novozymes) (Obtained) +TX, Bacillus cereus member EE128 (NRRL No. B-50917) +TX, Bacillus cereus member EE349 (NRRL No. B-50928) +TX, Bacillus cereus, especially strain BP01 (ATCC55675, for example from Arysta Lifescience, USA) )+TX, Bacillus mycosis fungoides BT155 (NRRL No. B-50921)+TX, Bacillus mycosis fungoides BT46-3 (NRRL No. B-50922)+TX, Bacillus mycosis fungoides EE118 (NRRL No. B-50918)+TX, Bacillus mycosis fungoides EE141 (NRRL No. B-50916)+TX, Bacillus pumilus, especially strain GB34 (e.g., YIELD from Bayer Crop Science, Germany) Bacillus subtilis, particularly strain QST2808 (NRRL No. B-30087), Bacillus sicca, particularly strain KCTC 13613T, Bacillus subtilis, particularly strain AQ30002 (NRRL No. B-50421 and described in U.S. Patent Application No. 13 / 330,576), Bacillus subtilis, particularly strain AQ30004 (NRRL No. B-50455 and described in U.S. Patent Application No. 13 / 330,576), Bacillus subtilis, particularly strain MBI 600 (e.g., from BASF AG) +TX, Bacillus subtilis rm303 (from a biofilm crop protection company) )+TX, Bacillus subtilis strain BU1814 (available from BASF AG) (Obtained) +TX, Bacillus tekirae, especially strain NII-0943+TX, Bacillus thuringiensis BT013A (NRRL No. B-50924), also known as Bacillus thuringiensis 4Q7+TX, soybean slow-growing rhizobia (e.g. from Novozymes) )+TX, Delfty acidophilic bacteria, especially strain RAY209 (e.g. from Brett Young Seeds) )+TX, Lactobacillus species (e.g., from LactoPAFI) )+TX, medium- and slow-growing rhizobia (e.g., NODULATOR from BASF AG)+TX, Bacillus polymyxa, especially strain AC-1 (e.g., from Green Biotechnology Co., Ltd.) )+TX, Pseudomonas aeruginosa, especially strain PN1+TX, Pseudomonas proradix (e.g. from Sourcon Padena) +TX, Rhizobium leguminosarium biovarviciae (e.g., NODULATOR from BASF) +TX, Rhizobium leguminosarium strain Z25 (accession number CECT 4585) +TX, Serratia marcescens strain SRM (accession number MTCC 8708) +TX, Rhizobium sinense strain NRG-185-1 (from Bayer Crop Science) GOLD)+TX, Thiobacillus species (e.g., from Cropaid Ltd, UK) )+TX;

[0465] Varicella valerate strain AARC-0255 (e.g., DiTera from Valent Biosciences) TM )+TX, Penicillium baicalensis strain ATCC 22348 (e.g. from Acceleron BioAg) )+TX, Penicillium baicalensis strain ATCC ATCC20851+TX, Paecilomyces lilacinus (formerly known as Paecilomyces lilacinus) strain 251 (AGAL 89 / 030550, e.g., BioAct from Bayer CropScience Biotechnology)+TX, Pythium oligandii strain DV74+TX, Pythium oligandii strain M1 (ATCC 38472, e.g., Polyversum from Bioprepraty, Czech Republic)+TX, Rhizopogon amylopogon (from Agri-Enterprise, formerly Myco-Sol from Helena Chemical Company)+TX, Rhizopogon folvii fulvigleba (e.g., from Agri-Enterprise, formerly Myco-Sol from Helena Chemicals) + TX, *Trichoderma fulvigleba* strain V117b + TX, *Trichoderma fulvigleba* strain (from Plant Health Products, South Africa, Eco-T) + TX, *Trichoderma fulvigleba* strain kd (e.g., from Andermart Biocontrol, T-Gro) + TX, *Trichoderma viride*, especially strain number V08 / 002387 + TX, *Trichoderma viride* strain CNCM 1-1237 (e.g., from Aglaucus, France) WP)+TX, Trichoderma viride strain LC52 (also known as Trichoderma viride strain LU132, e.g., Sentinel from Agrim Technology Ltd.)+TX, Trichoderma viride strain NMI number V08 / 002388+TX, Trichoderma viride strain NMI number V08 / 002389+TX, Trichoderma viride strain NMI number V08 / 002390+TX, Trichoderma viride strain SC1 (described in WO 2009 / 116106)+TX, Trichoderma harzianum strain 1295-22+TX, Trichoderma harzianum strain ITEM 908+TX, Trichoderma harzianum strain T-22 (e.g., from Andermatt Biocontrol or Cobert's Trianum-P)+TX, Trichoderma harzianum strain TSTh20,+TX, Trichoderma viride strain GI-3+TX, Trichoderma viride strain GL-21 (e.g., from Sertis, Inc.) )+TX, Trichoderma viride strain B35 (Pietr et al., 1993, Zesz.Nauk.AR w Szczecinie 161:125-137)+TX, Verticillium leuciscinum (formerly Verticillium dahliae) strain WCS850 (CBS276.92, e.g. Dutch Trig from Tree Care Innovations)+TX;

[0466] Agrobacterium radialis strain K84 (from Galltrol, Agribusiness Biosciences) + TX, Bacillus amyloliquefaciens, especially strain PTS-4838 (e.g., AVEO from Valencia Biosciences, USA) + TX, Bacillus mycosis fungoides, isolate J. (e.g., BmJ from Certis, USA) + TX, Bacillus spheroidae, especially serotype H5a5b strain 2362 (strain ABTS-1743) (e.g., from Valencia Biosciences, USA) +TX, Bacillus thuringiensis Israel strain BMP 144 (e.g., from Becker Microbial Products, IL, Illinois) )+TX, Bacillus thuringiensis subsp. niger strain GC-91+TX, Bacillus thuringiensis subsp. niger, especially serotype H-7 (e.g., from Valencia Biosciences, USA) WG)+TX, Bacillus thuringiensis subsp. niger, especially strain ABTS-1857 (SD-1372, for example, from Huarun Biosciences). )+TX, Bacillus thuringiensis subsp. Israel (serotype H-14) strain AM65-52 (accession number ATCC 1276) (e.g., from Valencia Biosciences, USA) +TX, Bacillus thuringiensis Kurstak subspecies strain ABTS 351 +TX, Bacillus thuringiensis Kurstak subspecies strain BMP 123 (from Becker Microbial Products, Illinois; BARITONE from Bayer Crop Science) +TX, Bacillus thuringiensis Kurstak subspecies strain EG 2348 (from Cetis, USA; LEPINOX) +TX, Bacillus thuringiensis Kurstak subspecies strain EG 7841 (from Cetis, USA; CRYMAX) +TX, Bacillus thuringiensis Kurstak subspecies strain HD-1 (e.g., from Valencia Biosciences, USA) ES)+TX, Bacillus thuringiensis Kurstak subspecies strain PB 54+TX, Bacillus thuringiensis Kurstak subspecies strain SA 11 (from JAVELIN, Certis, USA)+TX, Bacillus thuringiensis Kurstak subspecies strain SA 12 (from THURICIDE, Certis, USA)+TX, Bacillus thuringiensis Tenebrionibacterium subspecies strain NB 176 (SD-5428, for example from BioFa DE, Germany) Bacillus thuringiensis var. kurstaki (e.g., TIANBAO BTG® from Changzhou Jianghai Chemical Factory) + TX, Bacillus thuringiensis var. japonensis strain Buibui + TX, Bacillus thuringiensis var. kurstaki strain EVB-113-19 (e.g., BIOLEPTIN® from AEF Global) + TX, Bacillus vallismortis + TX, Paenibacillus alvei + TX, Burkholderia spp. especially Burkholderia rhizoxia strain A396 (also known as Burkholderia rhizoxia strain MBI 305) (Accession No. NRRL B-50319, WO 2011 / 106491 and WO 2013 / 032693, e.g., MBI206 TGAI and MBI206 TGAI from Maroni BioInnovation) + TX, Chromobacterium subtsugae especially strain PRAA4-1T (e.g., MBI-203, e.g., BIOLEPTIN® from Maroni BioInnovation) + TX, Lysinibacillus sphaericus strain 2362 (e.g., MBI-202, e.g., BIOLEPTIN® from Maroni BioInnovation) + TX, Veigella sp. (e.g., MBI-201, e.g., BIOLEPTIN® from Maroni BioInnovation) + TX, Paenibacillus popilliae (formerly Bacillus popilliae), e.g., MILKY SPORE POWDER (e.g., MILKY SPORE GRANULAR (e.g., from St. Gabriel Laboratories) + TX, Serratia entomophila (e.g., BIOLEPTIN® from Wrightson Seeds) + TX, Serratia marcescens especially strain SRM (Accession No. MTCC 8708) + TX, Trichoderma asperellum (TRICHODERMAX from Novozymes) + TX, Wolbachia pipientis ZAP strain (e.g., ZAP from MosquitoMate) + TX; TM TM

[0467] ​​​​​​​​) + TX, Beauveria bassiana strain ATP02 (Accession No. DSM 24665), Apopka 97 (PREFERAL from SePRO) + TX, Beauveria bassiana strain GHA (Accession No. ATCC 74250, e.g., from Laverlam International Corporation) + TX, Metarhizium anisopliae strain 3213-1 (deposited under NRRL Accession No. 67074, disclosed in WO 2017 / 066094, Pioneer Hi-Bred International) + TX, Metarhizium robertsii 15013-1 (deposited under NRRL Accession No. 67073) + TX, Metarhizium robertsii 23013-3 (deposited under NRRL Accession No. 67075) + TX, Paecilomyces lilacinus strain 251 (MELOCON from Archer Daniels Midland Company) + TX; ES and ) + TX, Beauveria bassiana strain ATP02 (Accession No. DSM 24665), Apopka 97 (PREFERAL from SePRO) + TX, Beauveria bassiana strain GHA (Accession No. ATCC 74250, e.g., from Laverlam International Corporation) + TX, Metarhizium anisopliae strain 3213-1 (deposited under NRRL Accession No. 67074, disclosed in WO 2017 / 066094, Pioneer Hi-Bred International) + TX, Metarhizium robertsii 15013-1 (deposited under NRRL Accession No. 67073) + TX, Metarhizium robertsii 23013-3 (deposited under NRRL Accession No. 67075) + TX, Paecilomyces lilacinus strain 251 (MELOCON from Archer Daniels Midland Company) + TX;

[0468] Cydia pomonella (codling moth) granulovirus (GV) + TX, Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV) + TX, Adoxophyes orana (summer fruit tortrix) granulovirus (GV) + TX, Spodoptera exigua (beet armyworm) mNPV + TX, Spodoptera frugiperda (fall armyworm) mNPV + TX;

[0469] Burkholderia species, especially Burkholderia zanus (formerly known as Pseudomonas zanus) +TX, Gigasparora species +TX, Glomus species +TX, Laccaria species +TX, LactoBacillus buchneri +TX, Paraglomus species +TX, Pisolithus tinctorus +TX, Pseudomonas species +TX, Rhizobium species, especially Rhizobium trifoliatum +TX, Rhizopogon species +TX, Scleroderma species +TX, Streptomyces species +TX, Suillus species spp.)+TX, Agrobacterium spp.+TX, Azorhizobium caulinodans+TX, Azospirillum spp.+TX, Azotobacter spp.+TX, Bradyrhizobium spp.+TX, Gigasparora monosporum+TX;

[0470] Garlic (NEMGUARD from Eco-Spray, BRALIC from ADAMA) +TX, Armour-Zen +TX, Wormwood +TX, Biokeeper WP +TX, Cruciferous extracts, especially rapeseed powder or mustard powder +TX, Black Cassia Seed +TX, Bitter Vine +TX, American Wild Mustard (Chenopodium anthelminticum) +TX, Quinoa Saponin Extract from Quinoa Seeds (e.g., Heads from Heads Up Plant Protectants, Canada) +TX Quinoa saponins + TX, chitin + TX, Dryopteris filix-mas + TX, horsetail + TX, Fortune Aza + TX, Fungastop + TX, Melaleuca alternifolia extract (from Stockton (STK) TIMOREX GOLD) + TX, naturally occurring Blad peptides extracted from lupin seeds (from FMC) ) + TX, naturally occurring Blad polypeptide extracted from Lupin seeds (from Sederma) ) + TX, pyrethrin + TX, Quassia amara + TX, Quercus + TX, Quillaja extract (QL AGRI 35 from BASF) + TX, REGALIA MAXX from Maroth Biotech) + TX, Requiem TM insecticide + TX, Reynoutria sachalinensis extract (REGALLIA + TX, Ryanodine / Ryanobiol + TX, Satureja + TX, Satureja montana + TX, Thymol + TX, Thymol mixed with geraniol (CEDROZ from Eden Research) + TX, Thymol mixed with geraniol and eugenol (MEVALONE from Eden Research) + TX, Triact 70 + TX, TriCon + TX, Tropaeulum majus + TX, Ulex europaeus + TX, Veratrine + TX, Viscum album + TX;

[0471] Mercury oxide + TX, Octhilinone + TX, Thiophanate-methyl + TX;

[0472] MGK 264 + TX, 2-(2-butoxyethoxy)ethyl piperinylate + TX, 2- isovalerylindan-1,3-dione + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone + TX, allylphenylglycidate + TX, allyl-S-methyl + TX, alpha-bromadiethylacetal + TX, aluminium phosphide + TX, anthraquinone + TX, antu + TX, arsenic trioxide + TX, barium carbonate + TX, benoxacor + TX, bispyribac + TX, bromethalin + TX, bromadiolone + TX, brofenprox + TX, calcium cyanide + TX, chloralose + TX, cholecalciferol + TX, cloquintocet (including cloquintocet-mexyl) + TX, copper naphthenate + TX, copper oxychloride + TX, coumachlor + TX, diphacin + TX, diphacinone + TX, difenadione + TX, difenapyramide + TX, dicyclopentadiene + TX, dimetridazole + TX, disulfiram + TX, dursban + TX, endosulfan + TX, ethylene dibromide + TX, ethylene dichloride + TX, ethylene oxide + TX, fenchlorazole (including fenchlorazole-ethyl) + TX, fenclorim + TX, fenitrothion + TX, fluacrypyrim + TX, fluracryl + TX, flupropadine + TX, flurprimidol + TX, flurprimidol hydrochloride + TX, flurazole + TX, gamma-HCH + TX, guazatine + TX, guazatine acetate + TX, HCH + TX, hydrogen cyanide + TX, imidacloprid + TX, iodomethane + TX, isoxadifen (including isoxadifen-ethyl) + TX, lindane + TX, magnesium phosphide + TX, MB-599 + TX, mefenpyr (including mefenpyr-diethyl) + TX, mefenpyr-sodium + TX, methiocarb + TX, methyl bromide + TX, nerolidol + TX, nifluramid + TX, petroleum oil + TX, phosphamidon + TX, phosphine + TX, phosphorus + TX, pindone + TX, piperonyl butoxide + TX, propionaldehyde + TX, potassium arsenite + TX, proquinazid + TX, propyl isomer + TX, pyridine-4-amine + TX, pyriminostim + TX, Polygonum cuspidatum extract + TX, ribavirin + TX, S421 + TX, scilliroside + TX, spinosad + TX, sodium arsenite + TX, sodium cyanide + TX, sodium fluoroacetate + TX, strychnine + TX, sulfoxide + TX, thallium sulfate + TX, selenium + TX, sulfallat + TX, warfarin + TX, zinc naphthenate + TX, zinc phosphide + TX, ziram + TX.

[0473] Furthermore, the compositions of the present application can also be applied together with one or more systemic acquired resistance inducers ("SAR" inducers). SAR inducers are known and described, for example, in US Patent No. US 6,919,298, and include, for example, salicylates as well as the commercial SAR inducer acibenzolar-S-methyl.

[0474] The compounds of formula (I) as defined in the present application are generally used in the form of compositions and can be applied to the crop area or to the crops to be treated, simultaneously or in succession with further compounds. These further compounds can be, for example, nutrients or micronutrients, or other preparations which influence the growth of plants. They can also be selective herbicides or non-selective herbicides, together with insecticides, fungicides, bactericides, nematocides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or adjuvants customarily employed in the art of formulation.

[0475] The compounds of formula (I) as defined in the present application can be used in the form of (fungicidal) compositions for controlling or protecting against phytopathogenic microorganisms, which comprise at least one compound of formula (I) as defined in the present application or at least one of the preferred individual compounds as defined above as active ingredient (in free form or in the form of an agricultically acceptable salt), and at least one of the abovementioned adjuvants.

[0476] The present application thus provides compositions, preferably fungicidal compositions, comprising at least one compound of formula (I) as defined in the present application, an agriculturally acceptable carrier and optionally adjuvants. An agriculturally acceptable carrier is, for example, a carrier suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, in addition to comprising a compound of formula (I) as defined in the present application, the compositions can comprise at least one or more pesticidally active compounds, for example additional fungicidally active ingredients.

[0477] Another aspect of the present application relates to a method of controlling or preventing infestation of a plant, for example a useful plant such as a crop plant, its propagation material, for example seeds, a harvested crop, for example a harvested food crop, or a non-living material by a phytopathogenic microorganism or a spoilage microorganism or an organism potentially harmful to man, especially a fungal organism, which comprises applying a compound of formula (I) as defined in the present application or a preferred individual compound as defined above as active ingredient to the plant, to a part thereof or the locus thereof, to its propagation material, or to any part of the non-living material.

[0478] By control or prevention is meant reducing the infestation by insects or by phytopathogenic microorganisms or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, to such a level that is deemed to be improved.

[0479] A preferred method of controlling or preventing infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, is foliar application, which comprises applying a compound of formula (I) as defined by the present application, or an agrochemical composition containing at least one of said compounds. The frequency of application and the rate of application will depend on the risk of infestation by the respective pathogen or insect. However, the compounds of formula (I) as defined by the present application can also penetrate the plant via the soil through the roots (systemic action) by drenching the locus of the plant with a liquid formulation or by applying the compound in solid form, e.g. in granular form, to the soil (soil application). In rice crops such granular formulations can be applied to the flooded rice field. The compounds of formula (I) as defined by the present application can also be applied to the seed (coating) by impregnating the seed or tuber with a liquid formulation of the fungicide or coating it with a solid formulation.

[0480] The formulations (e.g. compositions containing a compound of formula (I) as defined by the present application, and if desired, solid or liquid adjuvants or monomers for encapsulating a compound of formula (I) as defined by the present application) can be prepared in known manner, typically by intimately mixing the compound with extenders, e.g. solvents, solid carriers and, optionally, surface active compounds (surfactants).

[0481] The methods of applying these compositions, i.e. the methods of controlling the pathogens of the above-mentioned type, such as spraying, atomizing, dusting, brushing, coating, broadcasting or watering, as well as the use of these compositions for controlling the pathogens of the above-mentioned type, are further subjects of the present application. Typical concentrations are between 0.1 ppm and 1000 ppm, preferably between 0.1 ppm and 500 ppm, of active ingredient. The rate of application per hectare is preferably between 1 g and 2000 g, more preferably between 10 and 1000 g, most preferably between 10 and 600 g, of active ingredient per hectare. When used as seed-drenching agents, appropriate dosages are from 10 mg to 1 g of active substance per kg of seed.

[0482] When the combinations of the present application are used for treating seed, application rates 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, are generally sufficient.

[0483] Suitably, the composition comprising a compound of formula (I) as defined in the present application is applied preventively (meaning before the development of the disease) or curatively (meaning after the development of the disease).

[0484] The compositions of the present application can be used in any conventional form, for example, in the form of a twin pack, a dustable powder for dry seed treatment (DS), an emulsion for seed treatment (ES), a flowable concentrate for seed treatment (FS), a solution for seed treatment (LS), a water dispersible powder for seed treatment (WS), a capsule suspension for seed treatment (CF), a gel for seed treatment (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspoemulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an oil miscible (EO), a water miscible (EW), a microemulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra low volume suspension (SU), an ultra low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0485] Such compositions can be produced in a conventional manner, for example, by mixing the active ingredient with appropriate formulation inerts (diluents, solvents, fillers and optionally other formulation ingredients such as surfactants, biocides, anti-freeze agents, sticking agents, thickeners and compounds providing additional effects). Conventional slow release formulations aimed at long lasting efficacy can also be used. In particular, formulations to be applied in spray form, such as water dispersible concentrates (e.g. EC, SC, DC, OD, SE, EW, EO etc.), wettable powders and granules can contain surfactants such as wetting agents and dispersants and other compounds providing additional effects, for example, condensation products of formaldehyde with naphthalene sulphonate, alkyl aryl sulphonates, lignin sulphonates, fatty alkyl sulphates and ethoxylated alkyl phenols and ethoxylated fatty alcohols.

[0486] The compositions of the present application are applied to the seed in a suitable seed dressing formulation, for example, in the form of an aqueous suspension or a dry powder having good adhesion to the seed, using means known per se. Such seed dressing formulations are known in the art. The seed dressing formulation can contain a single active ingredient or a combination of active ingredients in encapsulated form, for example, as slow release capsules or microcapsules.

[0487] Generally, the formulations comprise from 0.01 % to 90% by weight of the active ingredient, from 0 to 20% of an agriculturally acceptable surfactant and from 10% to 99.99% of a solid or liquid formulation inert and one or more adjuvants, the active agent consisting of at least the compound of formula (I) as defined by the present application together with components (B) and (C) and optionally other active agents, in particular microbiocides or preservatives etc. Concentrated forms of the compositions usually contain between about 2% and 80%, preferably between about 5% and 70%, by weight of the active agent. Application forms of the formulations can for example contain from 0.01 % to 20%, preferably from 0.01 % to 5%, by weight of the active agent. However commercial products will preferably be formulated as concentrates, the end user will usually employ diluted formulations.

[0488] However commercial products will preferably be formulated as concentrates, the end user will usually employ diluted formulations.

[0489] Examples

[0490] The following examples serve to illustrate the present application. Certain compounds of the present application can differ from known compounds in that they have greater efficacy at low application rates, which can be demonstrated by the skilled person using the experimental procedures outlined in the examples.

[0491] Formulation Examples

[0492]

[0493] The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, to provide a wettable powder which can be diluted with water to give the desired concentration of the suspension.

[0494]

[0495] The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, to provide a powder which can be used directly for seed treatment.

[0496] Emulsifiable concentrates

[0497]

[0498] Emulsions of any desired dilution which can be used in plant protection can be obtained from such concentrates by dilution with water.

[0499]

[0500] By mixing the active ingredient with the carrier and grinding the mixture in a suitable mill, ready-to-use dusts are obtained. Such dusts can also be used for dry seed dressing.

[0501] Extruder granules

[0502]

[0503] The active ingredient is mixed and ground with the adjuvants and the mixture is moistened with water. The mixture is extruded and then dried in an air stream.

[0504] Coated granules

[0505] Active ingredient [compound of formula (I)] 8%

[0506] Polyethylene glycol (molecular weight 200) 3%

[0507] Kaolin 89%

[0508] The finely ground active ingredient is evenly applied in a mixer to kaolin moistened with polyethylene glycol. In this way, dust-free coated granules are obtained.

[0509] Suspension concentrates

[0510]

[0511] The finely ground active ingredient is intimately mixed with the adjuvants to give a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants and plant propagation materials can be treated and protected from microbial infestation by spraying, drenching or dipping.

[0512] Flowable concentrates for seed treatment

[0513]

[0514] The finely ground active ingredient is intimately mixed with the adjuvants to give a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants and plant propagation materials can be treated and protected from microbial infestation by spraying, drenching or dipping.

[0515] Slow release capsule suspensions

[0516] A mixture of 28 parts of the compound of formula (I) is combined with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate / poly-methylene-polyphenyl isocyanate-mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of an antifoam agent and 51.6 parts of water until the desired particle size is achieved. To this emulsion is added a mixture of 2.8 parts of 1,6-hexanediamine in 5.3 parts of water. The mixture is stirred until the polymerization is complete.

[0517] The obtained capsule suspension is stabilized by adding 0.25 parts of a thickening agent and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of active ingredient. The diameter of the media capsules is 8-15 microns.

[0518] The resulting formulation is applied to the seed as an aqueous suspension in a device suitable for this purpose.

[0519] Analytical Methods:

[0520] Throughout this specification, temperatures are given in degrees Celsius (°C) and "mp." means melting point. LC / MS means liquid chromatography mass spectrometry and the description of the apparatus and method is as follows:

[0521] LC-MS Method:

[0522] Method A:

[0523] The spectra are recorded on a mass spectrometer (SQD, SQDII single quadrupole mass spectrometer) from Waters equipped with an electrospray source (polarity: positive and negative ions, capillary: 3.00 kV, cone aperture 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 to 900 Da) and an Acquity UPLC from Waters: binary pump, heated column compartment, diode array detector and ELSD detector. Column: Waters UPLC HSS T3, 1.8 pm, 30 x 2.1 mm, temperature: 60 °C, DAD wavelength range (nm): 210 to 500, solvent gradient: A = water + 5% MeOH + 0.05% HCOOH, B = acetonitrile + 0.05% HCOOH; gradient: 10% - 100% B in 1.2 min; flow (ml / min) 0.85.

[0524] Method B:

[0525] Spectra were recorded on an ACQUITY mass spectrometer (SQD or SQDII single quadrupole mass spectrometer) from Waters Corporation equipped with an electrospray source (polarity: positive or negative ions, 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 to 800 Da) and an ACQUITY UPLC from Waters Corporation with solvent degasser, binary pump, heated column compartment and diode array detector. Column: Waters UPLC HSS T3, 1.8 pm, 30 x 2.1 mm, temperature: 60 °C, DAD wavelength range (nm): 210 to 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 (mL / min) 0.75.

[0526] Method C:

[0527] Spectra were recorded on a mass spectrometer (SQD, SQDII or QDA single quadrupole mass spectrometer) from Waters Corporation (Waters Corporation) equipped with an electrospray source (polarity: positive and negative ions), capillary voltage: 0.8-3.00 kV, cone: 5-30 V, source temperature: 120 °C-150 °C, desolvation temperature: 350 °C-600 °C, cone gas flow: 50-150 l / h, desolvation gas flow: 650-1000 l / h, mass range: 110 to 950 Da and an Acquity UPLC from Waters Corporation: binary pump, heated column compartment, diode array detector and ELSD. Column: Waters UPLC HSS T3, 1.8 pm, 30 x 2.1 mm, temperature: 60 °C, DAD wavelength range (nm): 210 to 400, run time: 1.5 min; solvents: A = water + 5% MeOH + 0.05% HCOOH, B = acetonitrile + 0.05% HCOOH; flow (mL / min) 0.85, gradient: 10% B isocratic for 0.2 min, then 10% - 100% B in 1.0 min, 100% B isocratic for 0.2 min, 100% - 10% B in 0.05 min, 10% B isocratic for 0.05 min

[0528] The following table A summarizes compounds of formula (I):

[0529] LC-MS data, such as retention time (RT), [M+H] + ,

[0530] - the type of method, and / or

[0531] - melting point (mp).

[0532] Table A:

[0533]

[0534]

[0535]

[0536]

[0537]

[0538]

[0539]

[0540]

[0541]

[0542]

[0543]

[0544] Preparation Examples:

[0545] Example 1: Preparation of N-[4-[6-[(4-chlorobenzoyl)-methyl-amino]imidazo[l,2- a]pyridin-3-yl]phenyl]carbamic acid methyl ester (Compound 27) Step A: Preparation of 3-bromoimidazo[l,2-a]pyridin-6-amine (Compound X-1)

[0546]

[0547] Step B: Preparation of N-(3-bromoimidazo[l,2-a]pyridin-6-yl)-4-chloro- benzamide

[0548]

[0549] To a solution of 3-bromo-6-nitro-imidazo[l,2-a]pyridine (1.00 g, 3.97 mmol) in ethyl acetate (30 mL) was added tin(II) chloride dihydrate (3.13 g, 15.9 mmol, 4.00 equiv) and the reaction mixture was stirred at room temperature for 16 hours. To the suspension was added 2 M sodium hydroxide solution until basic pH. The suspension was filtered over a pad of celite, washed with ethyl acetate, and the filtrate was extracted with ethyl acetate. 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 flash chromatography eluting with cyclohexane / ethyl acetate to give 3-bromoimidazo[l,2-a]pyridin-6-amine as a green solid.

[0550] LC-MS (Method A): Rt 0.15 min, m / z = 212 (M+H) +

[0551] 1 H-NMR (400 MHz, DMSO-d 6 , ppm) δ = 5.10-5.24 (m, 2H), 6.89-6.96 (m, 1H), 7.34-7.43 (m, 1H), 7.45-7.50 (m, 1H), 7.52-7.56 (m, 1H).

[0552] Step B: Preparation of N-(3-bromoimidazo[l,2-a]pyridin-6-yl)-4-chloro- benzamide

[0553]

[0554] To a solution of 3-bromoimidazo[l,2-a]pyridin-6-amine (compound X-1) (0.260 g, 1.13 mmol, 1.00 equiv) and triethylamine (0.346 g, 3.38 mmol, 0.476 mL, 3.00 equiv) was dissolved in tetrahydrofuran (7.80 mL). 4-Chlorobenzoyl chloride (0.302 g, 1.69 mmol, 0.221 mL, 1.50 equiv) was added dropwise at 10-15 °C and the mixture was stirred at room temperature for 1 hour. The mixture was diluted with ethyl acetate and treated with saturated sodium bicarbonate solution. The aqueous layer was extracted with ethyl acetate, 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 flash chromatography eluting with ethyl acetate / methanol to give N-(3-bromoimidazo[l,2-a]pyridin-6-yl)-4-chloro-benzamide.

[0555] LC-MS (Method A): Rt 0.84 min, m / z = 350 / 352 / 354 (M+H) +

[0556] 1 H-NMR (400MHz, DMSO-d) 6 ,ppm)δ=7.45-7.48(m,1H),7.48-7.50(m,1H),7.53-7.56(m,1H),7.56 -7.58(m,1H),7.59-7.63(m,1H),7.64-7.66(m,1H),7.96-8.01(m,3H).

[0557] Step C: Preparation of N-(3-bromoimidazo[l,2-a]pyridin-6-yl)-4-chloro-N- methyl-benzamide

[0558]

[0559] Sodium hydride (60% by weight in oil) (25.4 mg, 0.634 mmol, 1.30 equivalent) was added dropwise to an ice-cooled mixture of N-(3-bromoimidazolo[1,2-a]pyridin-6-yl)-4-chlorobenzamide (0.190 g, 0.488 mmol, 1.00 equivalent) dissolved in tetrahydrofuran (5.70 mL) and purged with argon. The resulting mixture was stirred at 0 °C for 20 min. Iodomethane (0.11 g, 0.046 mL, 0.73 mmol, 1.50 equivalent) was added dropwise, and the mixture was stirred at room temperature for 4 h. The mixture was diluted with ethyl acetate and treated with ice-cold water. The aqueous layer was extracted with ethyl acetate, and 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 silica gel rapid chromatography (eluting with cyclohexane / ethyl acetate) to obtain N-(3-bromoimidazolo[1,2-a]pyridin-6-yl)-4-chloro-N-methyl-benzamide in a yellow-brown resin.

[0560] LC-MS (Method A): Rt 0.84 min, m / z = 364 / 366 / 368 (M+H) +

[0561] 1 H-NMR (400MHz, DMSO-d) 6 ,ppm)δ=3.47-3.56(m,3H),7.05-7.13(m,1H),7.18-7.24(m,2H),7.30 -7.36(m,2H),7.55-7.61(m,1H),7.61-7.67(m,1H),7.80-7.89(m,1H).

[0562] Step D: Preparation of methyl N-[4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl]carbamate Step E: Preparation of methyl N-[4-[6-[(4-chlorobenzoyl)-methyl-amino]imidazo[l,2- a]pyridin-3-yl]phenyl]carbamate (Compound 27)

[0563]

[0564] To a solution of 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (0.200 g, 0.895 mmol, 1.00 equiv) and pyridine (0.216 g, 2.68 mmol, 3.00 equiv) in ethyl acetate (4 mL) at 10 °C was added methyl chloroformate (0.213 g, 0.175 mL, 2.24 mmol, 2.50 equiv) dropwise over 5 min. The resulting mixture was stirred at room temperature for 1 h. The mixture was diluted with ethyl acetate and treated with saturated sodium bicarbonate solution. The aqueous layer 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 flash chromatography eluting with cyclohexane / ethyl acetate to give methyl N-[4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]carbamate.

[0565] LC-MS (Method A): Rt 1.00 min, m / z = 278 (M+H) +

[0566] 1 H-NMR (400 MHz, DMSO-d 6 , ppm) δ = 1.30 - 1.36 (m, 12H), 3.74 - 3.84 (m, 3H), 6.60 - 6.72 (m, 1H), 7.35 - 7.45 (m, 2H), 7.69 - 7.81 (m, 2H).

[0567] Step E: Preparation of methyl N-[4-[6-[(4-chlorobenzoyl)-methyl-amino]imidazo[l,2- a]pyridin-3-yl]phenyl]carbamate (Compound 27) Example 2: Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-methyl- amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridinyl]carbamate (Compound 26)

[0568] Methyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (30.4 mg, 0.110 mmol, 2.00 equiv), N-(3-bromoimidazo[1,2-a]pyridin-6-yl)-4-chloro-N-methyl- benzamide (20.0 mg, 0.0549 mmol, 1.00 equiv), cesium carbonate (26.8 mg, 0.0823 mmol, 1.50 equiv) and tetrakis(triphenylphosphine)palladium(0) (3.170 mg, 0.002743 mmol, 0.050 equiv) were dissolved in water (0.5 mL) and 1,4-dioxane (1.5 mL). The suspension was purged with a stream of argon through three freeze-pump-thaw cycles and irradiated in a microwave at 100 °C for 30 min. After cooling to room temperature, the reaction mixture was filtered through a pad of celite 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 reverse phase chromatography (eluting with water / acetonitrile) to give methyl N-[4-[6-[(4-chlorobenzoyl)-methyl-amino]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate.

[0569] LC-MS (Method A): Rt 0.74 min, m / z = 435 / 437 (M+H)+

[0570] 1 H-NMR (400 MHz, DMSO-d 6 , ppm) δ = 3.38 - 3.50 (m, 3H), 3.75 - 3.85 (m, 3H), 6.99 - 7.08 (m, 2H), 7.09 - 7.17 (m, 1 H), 7.23 - 7.34 (m, 5H), 7.45 - 7.53 (m, 2H), 7.60 - 7.68 (m, 2H), 7.70 - 7.82 (m, 1 H).

[0571] Step A: Preparation of N-(3-bromoimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy- N-methyl-benzamide (Compound X-2) Step B: Preparation of N-(3-bromoimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy- N-methyl-benzamide

[0572]

[0573] Step C: Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-methyl- amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridinyl]carbamate (Compound 26) Example 3: Preparation of methyl N-[5-[6-[(4-cyano-3-ethoxy-benzoyl)-methyl- amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridinyl]carbamate (Compound 16)

[0574]

[0575] To a solution of 3-bromoimidazo[l,2-a]pyridin-6-amine (compound X-1, 2.00 g, 9.43 mmol, 1.00 equiv) and 4-fluoro-3-methoxy-benzoic acid (CAS: 82846-18-2) (1.60 g, 9.43 mmol, 1.00 equiv) in pyridine (30 mL) was added dropwise l-propanephosphonic anhydride solution (50% in ethyl acetate, 12.0 g, 18.9 mmol, 2.00 equiv) under nitrogen. The resulting solution was stirred at 70 °C for 3 hours. The reaction mixture was quenched with saturated aqueous sodium carbonate solution. The precipitate was collected by filtration, washed with water, triturated with diethyl ether to give N-(3-bromoimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy-benzamide as a brown solid.

[0576] LC-MS (Method A): Rt 1.09 min, m / z = 364 / 366 (M+H) +

[0577] 1 H-NMR (400 MHz, DMSO-d 6 , ppm) δ = 10.51 (s, 1H), 9.24 (dd, J = 2.0, 0.9 Hz, 1H), 7.76 (dd, J = 8.3, 2.1 Hz, 1H), 7.72 (d, J = 5.7 Hz, 1H), 7.72 - 7.68 (m, 1H), 7.65 (ddd, J = 8.5, 4.4, 2.2 Hz, 1H), 7.60 (dd, J = 9.7, 2.0 Hz, 1H), 7.46 - 7.39 (m, 1H), 3.96 (s, 3H).

[0578] Step A: Preparation of 3-bromo-N-methyl-imidazo[l,2-a]pyridin-6-amine Step B: Preparation of methyl N-[5-[6-(methylamino)imidazo[l,2-a]pyridin-3-yl]-2- pyridinyl]carbamate (Compound X-3)

[0579]

[0580] To an ice-cooled mixture of N-(3-bromoimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3- methoxy-benzamide (compound X-2, 0.267 g, 0.706 mmol, 1.00 equiv) dissolved in tetrahydrofuran (11.4 mL) purged with a stream of argon was added sodium hydride (60 mass% in oil) (0.0488 g, 1.22 mmol, 1.30 equiv) in portions and the resulting mixture was stirred at 0 °C for 20 minutes, iodomethane (0.200 g, 0.0877 mL, 1.41 mmol, 1.50 equiv) was added dropwise and the mixture was stirred at room temperature for 4 hours. The mixture was diluted with ethyl acetate and treated with ice-cold water. The desired material was extracted with ethyl acetate, 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 flash chromatography (eluting with cyclohexane / ethyl acetate; ethanol 3: 1) to give N-(3-bromoimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy-N-methyl- benzamide.

[0581] LC-MS (Method A): Rt 0.77 min, m / z = 378 / 380 (M+H) +

[0582] 1 H-NMR (400 MHz, DMSO-d 6 , ppm) δ = 3.46-3.56 (m, 3H), 3.75-3.84 (m, 3H), 6.79-6.94 (m, 2H), 7.07-7.14 (m, 1H), 7.14-7.21 (m, 1H), 7.58-7.70 (m, 2H), 7.80-7.91 (m, 1H).

[0583] Step C: Preparation of methyl 4-cyano-3-ethoxy-benzoate Step D: Preparation of 4-cyano-3-ethoxy-benzoic acid

[0584] N-(3-bromoimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy-N-methyl- benzamide (0.267 g, 0.706 mmol, 1.00 equiv) and methyl N-[5-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (0.283 g, 0.988 mmol, 1.40 equiv) were dissolved in dioxane (4.24 mL) and water (1.41 mL). Cesium carbonate (0.345 g, 1.06 mmol, 1.50 equiv) was added and the mixture was purged with a stream of argon for 5 minutes. Then tetrakis(triphenylphosphine)palladium(0) (0.0421 g, 0.0353 mmol, 0.05 equiv) was added. The mixture was irradiated in a microwave oven at 100 °C for 30 minutes. The mixture was diluted with ethyl acetate and treated with water. The aqueous layer was extracted with ethyl acetate, 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 flash chromatography eluting with cyclohexane / ethyl acetate; ethanol 3:1 to give methyl N-[5-[6-[(4-fluoro-3-methoxy- benzoyl)-methyl-amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate as a beige solid.

[0585] LC-MS (Method A): Rt 0.67 min, m / z = 450 (M+H) +

[0586] 1 H-NMR (400 MHz, DMSO-d 6 , ppm) δ = 3.43-3.52 (m, 3H), 3.76-3.83 (m, 3H), 3.84-3.90 (m, 3H), 6.75-6.89 (m, 1H), 6.90-7.00 (m, 1H), 7.04-7.12 (m, 1H), 7.20-7.26 (m, 1H), 7.36-7.45 (m, 1H), 7.65-7.72 (m, 1H), 7.72-7.79 (m, 2H), 7.82-7.92 (m, 1H), 8.05-8.14 (m, 1H), 8.14-8.20 (m, 1H).

[0587] Step E: Preparation of methyl N-[5-[6-[(4-cyano-3-ethoxy-benzoyl)-methyl- amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridinyl]carbamate (Compound 16) Example 4: Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)- (methoxymethyl)amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridinyl]carbamate (Compound 25)

[0588]

[0589] Step A: Preparation of N-(3-bromoimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy- N-(methoxymethyl)benzamide

[0590]

[0591] To a solution of 3-bromoimidazo[l,2-a]pyridin-6-amine (compound X-1, 3.70 g, 17.4 mmol, 1.00 equiv) in diethoxymethoxyethane (40.0 mL) was added 2,2,2-trifluoroacetic acid (0.0995 g, 0.872 mmol, 0.05 equiv). The solution was heated at 120 °C for 2 h. The reaction mixture was cooled and concentrated to give a yellow liquid. To a solution of this liquid in anhydrous ethanol (40.0 mL) at 0 °C was added sodium borohydride (1.98 g, 52.3 mmol, 3.00 equiv). The resulting suspension was stirred at room temperature for 20 min, and then heated at 80 °C for 3 h. The reaction mixture was cooled and concentrated. The residue was partitioned between diethyl ether and water, and the aqueous layer was extracted 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 silica gel flash chromatography (eluting with petroleum ether / ethyl acetate) to give 3-bromo-N-methyl-imidazo[l,2-a]pyridin-6-amine as a green solid.

[0592] LC-MS (Method A): Rt 0.55 min, m / z = 226 (M+H) +

[0593] 1 H-NMR (400 MHz, DMSO-d 6 , ppm) δ = 7.49 (s, 1H), 7.41 (d, J = 9.6 Hz, 1H), 7.10 (d, J = 1.2 Hz, 1H), 6.94 (dd, J = 9.6, 2.0 Hz, 1H), 5.85 (s, 1H), 2.70 (d, J = 3.8 Hz, 3H).

[0594] Step B: Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)- (methoxymethyl)amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridinyl]carbamate (Compound 25) Example 5: Preparation of methyl N-[5-[6-[(2-methoxypyridine-4-carbonyl)- methyl-amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridinyl]carbamate (Compound 8)

[0595]

[0596] To a solution of 3-bromo-N-methyl-imidazo[l,2-a]pyridin-6-amine (2.70 g, 11.9 mmol, 1.00 equiv) in dioxane / water (4: 1, 35.0 mL) was added methyl N-[5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (CAS: 1073372-02-7) (3.99 g, 14.3 mmol, 1.20 equiv), potassium carbonate (4.13 g, 29.9 mmol, 2.50 equiv) and l,l'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (0.874 g, 1.19 mmol, 0.10 equiv). The mixture was stirred at 65 °C under nitrogen for 2 hours. The resulting mixture was diluted with water and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel flash chromatography eluting with dichloromethane / methanol to give methyl N-[5-[6-(methylamino)imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate as a green solid.

[0597] LC-MS (Method A): Rt 0.70 min, m / z = 298 (M+H) +

[0598] 1 H-NMR (400 MHz, DMSO-d 6 , ppm) δ = 10.37 (s, 1H), 8.53 (d, J = 1.8 Hz, 1H), 8.09 (dd, J = 8.6, 2.4 Hz, 1H), 7.99 (d, J = 8.6 Hz, 1H), 7.57 (s, 1H), 7.44 (d, J = 9.4 Hz, 1H), 7.32 (s, 1H), 6.92 (dd, J = 9.6, 2.0 Hz, 1H), 5.66 (d, J = 4.8 Hz, 1H), 3.71 (d, J = 6.4 Hz, 3H), 2.64 (d, J = 4.2 Hz, 3H).

[0599] ​

[0600]

[0601] To a solution of methyl 4-cyano-3-hydroxy-benzoate (CAS: 6520-87-2) (2.00 g, 11.3 mmol, 1.00 equiv) in dimethylformamide (30.0 mL) was added cesium carbonate (7.356 g, 22.5 mmol, 2.00 equiv) and iodoethane (5.28 g, 33.86 mmol) under nitrogen. The reaction mixture was stirred at 40 °C for 2 hours. The resulting mixture was diluted with water 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 4-cyano-3-ethoxy-benzoate as a white solid.

[0602] 1 H-NMR (400 MHz, DMSO-d 6 , ppm) δ = 7.90 (d, J = 7.8 Hz, 1H), 7.62 (dd, J = 9.4, 1.4 Hz, 2H), 4.28 (q, 2H), 3.90 (s, 3H), 1.39 (t, 3H).

[0603] ​

[0604]

[0605] To a solution of methyl 4-cyano-3-ethoxy-benzoate (2.00 g, 9.75 mmol, 1.00 equiv) in methanol / tetrahydrofuran / water (5:5:4, 28.0 mL) was added lithium hydroxide (0.350 g, 14.6 mmol, 1.50 equiv). The reaction mixture was stirred at room temperature for 3 hours. The organic solvents were removed and the aqueous solution was adjusted to pH 2-3 with 2N hydrogen chloride solution. The precipitate was collected by filtration, washed with water to give 4-cyano-3-ethoxy-benzoic acid as an off-white solid.

[0606] LC-MS (Method A): Rt 1.01 min, m / z = 190 (M+H) -

[0607] 1 H-NMR (400 MHz, DMSO-d 6 , ppm) δ = 13.53 (s, 1H), 7.86 (d, J = 7.8 Hz, 1H), 7.64-7.58 (m, 2H), 4.27 (q, 2H), 1.39 (t, 3H).

[0608] ​ ​

[0609] To a solution of methyl N-[5-[6-(methylamino)imidazo[l,2-a]pyridin-3-yl]-2- pyridyl]carbamate (compound X-3) (0.300 g, 1.01 mmol, 1.00 equiv) and 4- cyano-3-ethoxy-benzoic acid (0.212 g, 1.11 mmol, 1.10 equiv) in pyridine (5.0 mL) was added dropwise 1-propanephosphonic anhydride solution (50% in ethyl acetate, 1.93 g, 3.03 mmol, 3.00 equiv) under nitrogen at 55 °C. The mixture was stirred at 55 °C for 3 hours. The resulting mixture was diluted with saturated aqueous sodium carbonate solution and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by reverse phase chromatography (eluting with acetonitrile / water containing 0.1% formic acid) to give methyl N-[5-[6-[(4-cyano-3-ethoxy-benzoyl)-methyl-amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate as a white solid.

[0610] LC-MS (Method A): Rt 0.96 min, m / z = 471 (M+H) +

[0611] 1 H-NMR (400 MHz, DMSO-d 6 , ppm) δ = 10.43 (s, 1H), 8.59 (s, 1H), 8.40 (s, 1H), 7.98 (d, J = 8.6 Hz, 1H), 7.78 (s, 2H), 7.59 (d, J = 12.4 Hz, 2H), 7.38 - 7.24 (m, 2H), 6.98 (s, 1H), 4.01 (s, 2H), 3.73 (s, 3H), 3.38 (s, 3H), 1.18 (s, 3H).

[0612] ​ ​

[0613]

[0614] ​ ​

[0615]

[0616] To a solution of N-(3-bromoimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy- benzamide (compound X-2, 200 mg, 0.549 mmol, 1.00 equiv) in dry tetrahydrofuran (4.0 mL) was added NaH 60.0% (43.9 mg, 1.10 mmol, 2.00 equiv) in oil at room temperature under nitrogen. The reaction mixture was stirred at room temperature for 60 minutes. Then bromo(methoxy)methane (82.4 mg, 0.659 mmol, 1.20 equiv) in tetrahydrofuran (1.0 mL) was added dropwise at 0 °C. The resulting solution was warmed to room temperature and stirred for 1 hour. The resulting mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel flash chromatography eluting with dichloromethane / methanol to give N-(3-bromoimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy-N- (methoxymethyl)benzamide as a sticky solid.

[0617] LC-MS (Method A): Rt 1.10 min, m / z = 408 / 410 (M+H) +

[0618] ​ ​

[0619] To a mixture of N-(3-bromoimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy-N- (methoxymethyl)benzamide (200 mg, 0.490 mmol, 1.00 equiv) and methyl N-[5-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (CAS: 1073372-02-7) (204 mg, 0.735 mmol, 1.50 equiv) in a pre-mixed solvent of dioxane / water (5:1, 8 mL) was added l, l'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (35.8 mg, 0.049 mmol, 0.10 equiv) and potassium carbonate (169 mg, 1.22 mmol, 2.50 equiv). The reaction mixture was stirred at 65 °C under nitrogen for 1 hour. The reaction mixture was concentrated under reduced pressure and the residue was purified by reverse phase chromatography eluting with water / acetonitrile containing 0.1% formic acid to give methyl N-[5-[6-[(4-fluoro-3-methoxy- benzoyl)-(methoxymethyl)amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate as an off-white solid.

[0620] LC-MS (Method A): Rt 0.90 min, m / z = 480 (M+H) +

[0621] 1 H-NMR (400MHz, DMSO-d) 6 ,ppm)δ=10.44(s,1H),8.56(s,1H),8.47-8.40(m,1H),8.00(d,J=8.7Hz,1H),7.85(s,1H),7.80(s,1H),7.60(d,J=9.5Hz,1H),7.33 (d,J=8.2Hz,1H),7.25(dd,J=9.5,1.9Hz,1H),7.12(d,J=10.2Hz,1H),7.01(s,1H),5.15(s,2H),3.73(d,J=6.8Hz,6H),3.35(s,3H).

[0622] ​ ​

[0623]

[0624] Add 1-methylimidazole (0.166 g, 2.02 mmol, 3.00 equivalents) and [chloro(dimethylamino)methylene]-dimethyl-hexafluorophosphate ammonium (0.283 g, 1.01 mmol, 1.50 equivalents) to a mixture of 2-methoxypyridinium-4-carboxylic acid (0.124 g, 0.807 mmol, 1.20 equivalents) in dimethylformamide (6 mL) to the mixture. Stir the reaction mixture at room temperature for 15 minutes. Then add N-[5-[6-(methylamino)imidazole[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X-3, 0.200 g, 0.673 mmol, 1.00 equivalents) in portions. Stir the resulting reaction mixture at room temperature for 2 hours. The mixture was filtered out and the residue was purified by reversed-phase chromatography (eluting with water / acetonitrile containing 0.1% formic acid) to give N-[5-[6-[(2-methoxypyridin-4-carbonyl)-methyl-amino]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate as a grayish-white solid.

[0625] LC-MS (Method A): Rt 0.80 min, m / z = 433(M+H) +

[0626] 1 H-NMR (400MHz, DMSO-d) 6ppm) δ = 10.45 (s, 1H), 8.61 (s, 1H), 8.40 (s, 1H), 8.00 (d, J = 8.7 Hz, 2H), 7.85-7.71 (m, 2H), 7.61 (d, J = 9.6 Hz, 1H), 7.35 (d, J = 9.4 Hz, 1H), 6.94-6.85 (m, 1H), 6.82 (s, 1H), 3.75 (s, 3H), 3.73 (s, 3H), 3.36 (s, 3H)

[0627] Example 6: Preparation of methyl N-[5-[6-[(4-cyano-3-methoxy- benzoyl)-methyl-amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate (Compound 9) Example 6: Preparation of methyl N-[5-[6-[(4-cyano-3-methoxy- benzoyl)-methyl-amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate (Compound 9)

[0628]

[0629] Step A: Preparation of methyl 4-cyano-3-methoxy-benzoate

[0630]

[0631] To a solution of methyl 4-cyano-3-hydroxy-benzoate (1.00 g, 5.64 mmol, 1.00 equiv) in dimethylformamide (15.0 mL) was added cesium carbonate (3.68 g, 11.3 mmol, 2.00 equiv) and iodomethane (2.40 g, 16.9 mmol, 3.00 equiv). The reaction mixture was stirred at 40 °C for 2 hours. The resulting mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford methyl 4-cyano-3-methoxy-benzoate as a white solid.

[0632] 1 H-NMR (400 MHz, DMSO-d 6 ppm) δ = 7.91 (d, J = 7.8 Hz, 1H), 7.64 (dd, J = 10.2, 2.2 Hz, 2H), 4.00 (s, 3H), 3.91 (s, 3H).

[0633] Step B: Preparation of 4-cyano-3-methoxy-benzoic acid

[0634]

[0635] To a solution of methyl 4-cyano-3-methoxy-benzoate (1.00 g, 5.23 mmol, 1.00 equiv) in methanol / tetrahydrofuran / water (5:5:4, 14.0 mL) was added lithium hydroxide (0.188 g, 7.85 mmol, 1.50 equiv). The reaction mixture was stirred at room temperature for 3 hours. The resulting mixture was concentrated under reduced pressure and the aqueous solution was adjusted to pH 2-3 with 2N hydrochloric acid. The formed precipitate was filtered off, washed with water and dried under reduced pressure to give 4-cyano-3-methoxy-benzoic acid as a white solid.

[0636] LC-MS (Method A): Rt 0.99 min, m / z = 176 (M-H) -

[0637] 1 H-NMR (400 MHz, DMSO-d 6 , ppm) δ = 13.61 (s, 1H), 7.87 (d, J = 7.8 Hz, 1H), 7.69-7.57 (m, 2H) 3.99 (s, 3H).

[0638] Step C: Preparation of methyl N-[5-[6-[(4-cyano-3-methoxy- benzoyl)-methyl-amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate (Compound 9) Example 6: Preparation of methyl N-[5-[6-[(4-cyano-3-methoxy- benzoyl)-methyl-amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate (Compound 9)

[0639] To a solution of methyl 4-cyano-3-methoxy-benzoate (1.00 g, 5.23 mmol, 1.00 equiv) in methanol / tetrahydrofuran / water (5:5:4, 14.0 mL) was added lithium hydroxide (0.188 g, 7.85 mmol, 1.50 equiv). The reaction mixture was stirred at room temperature for 3 hours. The resulting mixture was concentrated under reduced pressure and the aqueous solution was adjusted to pH 2-3 with 2N hydrochloric acid. The formed precipitate was filtered off, washed with water and dried under reduced pressure to give 4-cyano-3-methoxy-benzoic acid as a white solid.

[0640] LC-MS (Method A): Rt 0.90 min, m / z = 457 (M+H) +

[0641] 1 H-NMR (400 MHz, DMSO-d6 ppm) δ = 10.43 (s, 1H), 8.56 (s, 1H), 8.34 (s, 1H), 7.98 (d, J = 8.6 Hz, 1H), 7.78 (s, 2H), 7.59 (s, 2H), 7.40-7.29 (m, 2H), 6.98 (s, 1H), 3.79 (s, 3H), 3.73 (s, 3H), 3.38 (s, 3H).

[0642] Example 7: Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy- benzoyl)-methyl-amino]-8-methyl-imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate (Compound 13) Step A: Preparation of tert-butyl N-(8-methylimidazo[l,2-a]pyridin-6- yl)carbamate

[0643]

[0644] Step B: Preparation of tert-butyl N-methyl-N-(8-methylimidazo[l,2- a]pyridin-6-yl)carbamate

[0645]

[0646] To a solution of 6-bromo-8-methyl-imidazo[l,2-a]pyridine (2.00 g, 9.48 mmol, 1.00 equiv), tert-butyl carbamate (4.44 g, 37.9 mmol, 4.00 equiv) and sodium 2-methylpropan-2-olate (3.64 g, 37.9 mmol, 4.00 equiv) in dioxane (30.0 mL) was added [2-(2- aminophenyl)phenyl]-methylsulfonyloxy-palladium; dicyclohexyl-[3,6-dimethoxy-2-(2,4,6- triisopropylphenyl)phenyl]phosphine (0.859 g, 0.948 mmol, 0.10 equiv) and dicyclohexyl-[3,6-dimethoxy-2-(2,4,6-triisopropylphenyl)phenyl]phosphine (1.02 g, 1.90 mmol, 0.20 equiv). The reaction mixture was stirred at 100 °C under nitrogen for 8 hours. The resulting mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with dichloromethane / methanol to afford tert-butyl N-(8-methylimidazo[l,2-a]pyridin-6-yl)carbamate as a yellow solid.

[0647] LC-MS (Method A): Rt 0.74 min, m / z = 248 (M+H) +

[0648] Step C: Preparation of tert-butyl N-(3-bromo-8-methyl-imidazo[l,2- a]pyridin-6-yl)-N-methyl-carbamate

[0649]

[0650] To an ice-cooled solution of tert-butyl N-(8-methylimidazo[l,2- a]pyridin-6-yl)carbamate (0.0200 g, 0.0809 mmol, 1.00 equiv) in tetrahydrofuran (3.00 mL) under nitrogen was added sodium hydride (60% in oil, 0.0029 g, 0.12 mmol, 1.3 equiv). The solution was stirred at 0 °C for 45 min and then iodomethane (0.0230 g, 0.162 mmol, 2.00 equiv) was added dropwise. The resulting solution was slowly warmed to room temperature and stirred for 3 h. The aqueous solution was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford tert-butyl N-methyl-N-(8-methylimidazo[l,2-a]pyridin-6-yl)carbamate as a yellow solid.

[0651] LC-MS (Method A): Rt 0.76 min, m / z = 262 (M+H)+

[0652] Step D: Preparation of 3-bromo-N,8-dimethyl-imidazo[l,2-a]pyridin-6- amine Step E: Preparation of methyl N-[5-[8-methyl-6-(methylamino)imidazo[l,2- a]pyridin-3-yl]-2-pyridyl]carbamate

[0653]

[0654] To a solution of tert-butyl N-methyl-N-(8-methylimidazo[l,2-a]pyridin-6- yl)carbamate (0.480 g, 1.84 mmol, 1.00 equiv) in dimethylformamide (4.00 mL) was added a solution of l-bromopyrrolidine-2,5-dione (0.360 g, 2.02 mmol, 1.10 equiv) in dimethylformamide (1.0 ml) dropwise. The reaction mixture was stirred at room temperature for 1 h. The aqueous solution was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford tert-butyl N-(3-bromo-8-methyl-imidazo[l,2-a]pyridin-6-yl)-N-methyl- carbamate as a yellow solid.

[0655] LC-MS (Method A): Rt 1.23 min, m / z = 340 / 342 (M+H) +

[0656] Step F: Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)- methyl-amino]-8-methyl-imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate (Compound 13)

[0657]

[0658] A solution of N-(3-bromo-8-methyl-imidazo[l,2-a]pyridin-6-yl)-N-methyl- carbamic acid tert-butyl ester (8.40 g, 24.7 mmol, 1.00 equiv) in dichloromethane / trifluoroacetic acid (1 : 1, 100.0 mL) was stirred at room temperature for 1 hour. The aqueous solution was diluted with saturated aqueous sodium carbonate solution 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 3-bromo-N,8-dimethyl-imidazo[l,2-a]pyridin-6-amine as a yellow solid.

[0659] LC-MS (Method A): Rt 0.62 min, m / z = 240 / 242 (M+H) +

[0660] Example 8: Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy- benzoyl)-(2-methoxyethyl)amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate (Compound 14) Step A: Preparation of N-(3-bromimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3- methoxy-N-(2-methoxyethyl)benzamide

[0661]

[0662] To a stirred mixture of 3-bromo-N,8-dimethyl-imidazo[l,2-a]pyridin-6-amine (0.750 g, 3.12 mmol, 1.00 equiv), methyl N-[5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-2- pyridyl]carbamate (1.04 g, 3.75 mmol, 1.20 equiv), and potassium carbonate (1.08 g, 7.81 mmol, 2.50 equiv) in dioxane / water (5: 1, 10.0 mL) was added 1,1'- bis(diphenylphosphino)ferrocene-palladium(II) dichloromethane complex (0.255 g, 0.312 mmol, 0.1 equiv). The reaction mixture was stirred at 60 °C under nitrogen for 2 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel flash chromatography eluting with dichloromethane / methanol to give methyl N-[5-[8-methyl-6-(methylamino)imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate as a white solid.

[0663] LC-MS (Method A): Rt 0.80 min, m / z = 312 (M+H)+

[0664] Step B: Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)- (2-methoxyethyl)amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate (Compound 14) Example 9: Preparation of methyl N-[5-[6-[(4-cyano-3-methyl- benzoyl)-methyl-amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate (Compound 17)

[0665] To a mixture of 4-fluoro-3-methoxy-benzoic acid (0.0656 g, 0.385 mmol, 1.20 equiv) in dimethylformamide (6 mL) was added 1-methylimidazole (0.0791 g, 0.964 mmol, 3.00 equiv) and [chloro(dimethylamino)methylene]-dimethyl-ammonium hexafluorophosphate (0.135 g, 0.482 mmol, 1.50 equiv). The reaction mixture was stirred at room temperature for 5 minutes. Then methyl N-[5-[8-methyl-6-(methylamino)imidazo[l,2- a]pyridin-3-yl]-2-pyridyl]carbamate (0.100 g, 0.321 mmol, 1.00 equiv) was added portionwise. The resulting reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with saturated aqueous sodium carbonate solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography (eluting with water / acetonitrile containing 0.1% formic acid) to give methyl N-[5-[6-[(4-fluoro-3-methoxy- benzoyl)-methyl-amino]-8-methyl-imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate as a white solid.

[0666] LC-MS (Method A): Rt 0.93 min, m / z = 464 (M+H) +

[0667] 1 H-NMR (400 MHz, DMSO-d 6 , ppm) δ = 10.56 (s, 1H), 8.58 (s, 1H), 8.37 (s, 1H), 8.28 (s, 1H), 8.03 (d, J = 8.7 Hz, 1H), 7.77 (s, 2H), 7.25 (d, J = 7.1 Hz, 1H), 7.13-7.08 (m, 1H), 6.89 (s, 1H), 3.73 (s, 6H), 3.36 (s, 3H), 2.55 (s, 3H).

[0668] Example 10: Preparation of methyl N-[5-[6-[(4-cyano-3-methyl- benzoyl)-methyl-amino]-8-methyl-imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate (Compound 2) ​

[0669]

[0670] ​ ​

[0671]

[0672] To a solution of N-(3-bromoimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy- benzenecarboxamide (compound X-2) (0.260 g, 0.714 mmol, 1.00 equiv) in dimethylformamide (6.0 mL) was added sodium 2-methylpropan-2-olate (0.172 g, 1.78 mmol, 2.50 equiv) and 1-bromo-2-methoxy-ethane (0.397 g, 2.86 mmol, 4.00 equiv) under nitrogen. The reaction mixture was stirred at 80 °C for 16 h. The resulting reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with dichloromethane / methanol to give N-(3-bromoimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy-N-(2-methoxyethyl)benzenecarboxamide as a green oil.

[0673] LC-MS (Method A): Rt 1.09 min, m / z = 422 / 424 (M+H) +

[0674] ​ ​

[0675] To a solution of N-(3-bromoimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy-N-(2- methoxyethyl)benzenecarboxamide (80.0 mg, 0.189 mmol, 1.00 equiv), methyl N-[5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (0.0632 g, 0.227 mmol) and potassium carbonate (0.0655 g, 0.474 mmol, 2.50 equiv) in dioxane / water (4: 1, 1.5 mL) was added l, l'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (0.0139 g, 0.0189 mmol, 0.10 equiv). The reaction mixture was stirred at 65 °C for 2 h under nitrogen. The resulting mixture was concentrated under reduced pressure and the crude residue was purified by reverse phase chromatography eluting with water / acetonitrile containing 0.1% formic acid to give methyl N-[5-[6-[(4-fluoro-3-methoxy- benzenecarbonyl)-(2-methoxyethyl)amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate as a white solid.

[0676] LC-MS (Method A): Rt 0.92 min, m / z = 494 (M+H) +

[0677] 1H-NMR (400MHz, DMSO-d) 6 ,ppm)δ=10.44(s,1H),8.55(s,1H),8.39(s,1H),7.99(d,J=8.6Hz,1H),7.82(s,2H),7.58(d,J=9.4Hz,1H),7.2 6(d,J=10.0Hz,2H),7.06(s,1H),6.87(s,1H),3.98(s,2H),3.72(s,3H),3.70(s,3H),3.56(s,2H),3.23(s,3H)

[0678] ​ ​

[0679]

[0680] Add 1-methylimidazole (0.0306 g, 0.372 mmol, 3.00 equivalent) and [chloro(dimethylamino)methylene]-dimethyl-hexafluorophosphate ammonium (0.052 g, 0.186 mmol, 1.50 equivalent) to a mixture of 4-cyano-3-methylbenzoic acid (0.02 g, 0.124 mmol, 1.00 equivalent) and dimethylformamide (2 mL) to a mixture of 4-cyano-3-methylbenzoic acid (0.02 g, 0.186 mmol, 1.50 equivalent). Stir the reaction mixture at room temperature for 5 minutes. Then add N-[5-[6-(methylamino)imidazole[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X-3) (0.044 g, 0.149 mmol, 1.00 equivalent) in portions. Stir the resulting reaction mixture at room temperature for 1 hour. Quench the reaction mixture with a saturated aqueous sodium carbonate solution and extract with ethyl acetate. Wash the combined organic layers with brine, dry over sodium sulfate, filter, and concentrate under reduced pressure. The residue was purified by reversed-phase chromatography (eluting with water / acetonitrile containing 0.1% formic acid) to give N-[5-[6-[(4-cyano-3-methyl-benzoyl)-methyl-amino]imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]carbamate as a white solid.

[0681] LC-MS (Method A): Rt 0.88 min, m / z = 441(M+H) +

[0682] 1 H-NMR (400MHz, DMSO-d) 6,ppm)δ=10.44(s,1H),8.55(s,1H),8.32(s,1H),7.99(d,J=8.6Hz,1H),7.80(s,1H),7.71(m,1 H),7.60(m,2H),7.55(s,1H),7.32(d,1H),7.20(s,1H),3.70(s,3H),3.40(s,3H),2.40(s,3H).

[0683] ​ ​

[0684]

[0685] At room temperature, 1-methylimidazole (0.0791 g, 0.964 mmol) and [chloro(dimethylamino)methylene]-dimethyl-hexafluorophosphate ammonium (0.135 g, 0.482 mmol) were added to a mixture of 4-cyano-3-methylbenzoic acid (CAS 73831-13-7, 0.0656 g, 0.385 mmol) and N,N-dimethylformamide (3.00 mL). The solution was stirred for 5 min. Then, N-[5-[8-methyl-6-(methylamino)imidazole[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X-4, 0.100 g, 0.321 mmol) was added in portions. The resulting solution was stirred for 2 h. The reaction mixture was quenched with saturated sodium bicarbonate aqueous solution 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 residue was purified by reversed-phase chromatography (eluting with acetonitrile / water containing 0.1% formic acid) to provide N-[5-[6-[(4-cyano-3-methyl-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]carbamate as a white solid.

[0686] LC-MS (Method A): Rt 0.92 min, m / z = 455(M+H) +

[0687] 1 H-NMR (400MHz, DMSO-d) 6 ,ppm)δ=10.56(s,1H),8.58(s,1H),8.37(s,1H),8.28(s,1H),8.03(d,J=8.7Hz,1H),7.77(s,2H ),7.25(d,J=7.1Hz,1H),7.13-7.08(m,1H),6.89(s,1H),3.73(s,6H),3.36(s,3H),2.55(s,3H).

[0688] Example 11: Preparation of methyl N-[5-[6-[(4-cyano-3-ethoxy-benzoyl)-methyl- amino]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]carbamate (Compound 10) Example 11: Preparation of methyl N-[5-[6-[(4-cyano-3-ethoxy-benzoyl)-methyl- amino]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]carbamate (Compound 10)

[0689]

[0690] Step A: Preparation of 4-cyano-3-ethoxy-benzoic acid

[0691]

[0692] To a solution of methyl 4-cyano-3-ethoxy-benzoate (CAS 220380-12-1, 2.00 g, 9.75 mmol) in methanol / tetrahydrofuran / water (5:5:4, 28.0 mL) was added lithium hydroxide (0.350 g, 14.6 mmol). The mixture was stirred at room temperature for 3 hours. The organic solvents were then removed under reduced pressure. The aqueous solution was adjusted to pH 2-3 with 2N hydrochloric acid. The precipitate was collected by filtration, washed with water to afford 4-cyano-3-ethoxy-benzoic acid as a white solid.

[0693] LC-MS (Method A): Rt 1.10 min, m / z = 189.9 (M-H) +

[0694] 1 H-NMR (400 MHz, DMSO-d 6 , ppm) δ = 13.53 (s, 1 H), 7.86 (d, J = 7.8 Hz, 1 H), 7.64-7.58 (m, 2H), 4.27 (q, J = 7.0 Hz, 2H), 1.39 (t, J = 7.0 Hz, 3H).

[0695] Step B: Preparation of methyl N-[5-[6-[(4-cyano-3-ethoxy-benzoyl)-methyl-amino]- 8-methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]carbamate (Compound 10) Example 11: Preparation of methyl N-[5-[6-[(4-cyano-3-ethoxy-benzoyl)-methyl- amino]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]carbamate (Compound 10)

[0696] To a solution of methyl N-[5-[8-methyl-6-(methylamino)imidazo[l,2- a]pyridin-3-yl]-2-pyridyl]carbamate (compound X-4, 0.200 g, 0.642 mmol) and 4- cyano-3-ethoxy-benzoic acid (0.135 g, 0.707 mmol) in pyridine (3.0 mL) was added propanephosphonic anhydride (50.0%, 2.45 g, 3.85 mmol) dropwise under a nitrogen atmosphere at 65 °C. The mixture was heated at 65 °C for 6 hours. The resulting mixture was then concentrated under reduced pressure. The reaction mixture was diluted with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organic layers were washed with water then brine, dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by reverse phase chromatography (water / acetonitrile containing 0.1% formic acid) to provide methyl N-[5-[6-[(4-cyano-3-ethoxy-benzoyl)-methyl-amino]-8-methyl- imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate as an off-white solid.

[0697] LC-MS (Method A): Rt 0.95 min, m / z = 485 (M+H) +

[0698] 1 H-NMR (400 MHz, DMSO-d 6 , ppm) δ = 10.42 (s, 1H), 8.37 (d, J = 16.4 Hz, 2H), 7.97 (d, J = 8.6 Hz, 1H), 7.72 (d, J = 10.6 Hz, 2H), 7.56 (s, 1H), 7.26 (d, J = 10.0 Hz, 2H), 6.97 (s, 1H), 4.01 (s, 2H), 3.72 (s, 3H), 3.36 (s, 3H), 2.46 (s, 3H), 1.19 (s, 3H).

[0699] Example 12: Preparation of methyl N-[5-[6-[(3-ethoxy-4-fluoro-benzoyl)-methyl- amino]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]carbamate (Compound 19) Example 13: Preparation of methyl N-[5-[6-[(3-methoxybenzoyl)-methyl-amino]-8- methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]carbamate (Compound 53)

[0700]

[0701] To a mixture of 3-ethoxy-4-fluoro-benzoic acid (0.0650 g, 0.353 mmol) in N,N- dimethylformamide (2.00 mL) was added 1-methylimidazole (0.0869 g, 1.06 mmol) and [chloro(dimethylamino)methylene]-dimethyl-ammonium hexafluorophosphate (0.149 g, 0.529 mmol) at room temperature. The solution was stirred for 5 min. Then methyl N-[5-[8-methyl-6-(methylamino)imidazo[l,2- a]pyridin-3-yl]-2-pyridyl]carbamate (Compound X-4, 0.121 g, 0.388 mmol) was added portionwise. The resulting solution was stirred at room temperature for 2 hours. The reaction mixture was quenched with saturated aqueous sodium bicarbonate solution 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 residue was purified by reverse phase chromatography eluting with acetonitrile / water containing 0.1% formic acid to afford methyl N-[5-[6-[(3-ethoxy-4-fluoro-benzoyl)-methyl-amino]-8-methyl- imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate as an off-white solid.

[0702] LC-MS (Method A): Rt 0.96 min, m / z = 478 (M+H) +

[0703] 1 H-NMR (400 MHz, DMSO-d 6 , ppm) δ = 10.43 (s, 1H), 8.35 (d, J = 13.8 Hz, 2H), 7.96 (d, J = 8.6 Hz, 1H), 7.78 (s, 1H), 7.71 (d, J = 8.4 Hz, 1H), 7.26 (s, 1H), 7.18 (d, J = 7.8 Hz, 1H), 7.11 - 7.05 (m, 1H), 6.89 (s, 1H), 3.91 (q, J = 6.6 Hz, 2H), 3.72 (s, 3H), 3.35 (s, 3H), 2.48 (s, 3H), 1.16 (t, J = 6.8 Hz, 3H).

[0704] Example 14: Preparation of methyl N-[5-[8-acetamido-6-[(4-fluoro-3-methoxy- benzoyl)-methyl-amino]imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]carbamate (Compound 59) Step A: Preparation of 8-bromo-6-nitro-imidazo[1,2-a]pyridine (Compound X-5)

[0705]

[0706] A vial was charged with 3-methoxybenzoic acid (0.6 mmol) in N,N- dimethylacetamide (0.30 mL), followed by diisopropylethylamine (0.041 mL, 0.24 mmol) in N,N-dimethylacetamide (0.20 mL), methyl N-[5-[8-methyl-6- (methylamino)imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate (Compound X-4) (12.5 mg, 0.040 mmol) in N,N-dimethylacetamide (0.20 mL), and bis(2-oxo-3- oxazolidinyl)phosphinic chloride (20.6 mg, 0.080 mmol) in N,N-dimethylacetamide (0.50 mL). The reaction mixture was stirred at 60 °C for 4 h. Then, methanol (0.30 mL) was added and the mixture was purified by reverse phase chromatography to give methyl N-[5-[6-[(3-methoxybenzoyl)-methyl-amino]-8-methyl- imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate.

[0707] LC-MS (Method D): Rt 0.83 min, m / z = 446 (M+H) +

[0708] Step B: Preparation of 8-bromo-imidazo[1,2-a]pyridin-6-amine Step C: Preparation of 8-bromo-N-methyl-imidazo[1,2-a]pyridin-6-amine

[0709]

[0710] Step D: Preparation of N-(8-bromo-imidazo[1,2-a]pyridin-6-yl)-4-fluoro-3-methoxy- N-methyl-benzamide (Compound X-6)

[0711]

[0712] To a stirred solution of 3-bromo-5-nitro-pyridin-2-amine (10.0 g, 45.9 mmol) in ethanol (100 mL) was added 2-chloroacetaldehyde (25.2 g, 321 mmol) and sodium bicarbonate (6.94 g, 82.6 mmol) at room temperature. The reaction mixture was stirred at 80 °C for 16 h. Then, the solvent was removed and the residue was basified with saturated aqueous sodium bicarbonate solution and extracted with dichloromethane. The combined organic phases were concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with petroleum ether / ethyl acetate to give 8-bromo-6-nitro-imidazo[l,2-a]pyridine as a yellow solid.

[0713] LC-MS (Method A): Rt 0.95 min, m / z = 242 (M+2H) 2+

[0714] Step E: Preparation of N-(8-acetamido-imidazo[1,2-a]pyridin-6-yl)-4-fluoro-3- methoxy-N-methyl-benzamide

[0715]

[0716] To a solution of 8-bromo-6-nitro-imidazo[l,2-a]pyridine (compound X-5) (5.00 g, 20.7 mmol) in ethanol / water (1 : 1, 60.0 mL) was added ammonium chloride (5.53 g, 103 mmol) and iron (5.77 g, 103 mmol) at room temperature. The reaction mixture was stirred at 80 °C for 4 hours. The mixture was concentrated under reduced pressure, filtered and washed with ethyl acetate. The resulting mixture was then diluted with water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with pentane / ethyl acetate to give 8-bromoimidazo[l,2-a]pyridin-6-amine as a yellow solid.

[0717] LC-MS (Method A): Rt 0.22 min, m / z = 214 (M+2H) 2+

[0718] Step F: Preparation of N-(8-acetamido-3-bromo-imidazo[1,2-a]pyridin-6-yl)-4-fluoro- 3-methoxy-N-methyl-benzamide

[0719]

[0720] To a solution of 8-bromoimidazo[l,2-a]pyridin-6-amine (0.400 g, 1.89 mmol) in triethyl orthoformate (4.0 mL) was added trifluoroacetic acid (0.0108 g, 0.0943 mmol). The solution was heated at 120 °C for 2 hours. The mixture was then allowed to cool to room temperature and concentrated under reduced pressure. The resulting yellow liquid was diluted with ethanol (4.0 mL) and sodium borohydride (0.0714 g, 1.89 mmol) was added portionwise at 0 °C. The resulting suspension was stirred at 80 °C for 3 hours. The mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure to give 8-bromo-N-methyl-imidazo[l,2-a]pyridin-6-amine as a brown solid which was used directly in the next step without further purification.

[0721] LC-MS (Method A): Rt 0.31 min, m / z = 226 (M+H) +

[0722] Step G: Preparation of methyl N-[5-[8-acetamido-6-[(4-fluoro-3-methoxy- benzoyl)-methyl-amino]imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]carbamate (Compound 59) Example 15: Preparation of methyl N-[5-[8-cyano-6-[(4-fluoro-3-methoxy- benzoyl)-methyl-amino]imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]carbamate (Compound 55)

[0723]

[0724] To a solution of 8-bromo-N-methyl-imidazo[l,2-a]pyridin-6-amine (1.50 g, 6.64 mmol) and 4-fluoro-3-methoxy-benzoic acid (1.35 g, 7.96 mmol) in pyridine (20.0 mL) was added propanephosphonic anhydride (50.0%, 6.33 g, 19.9 mmol) dropwise under a nitrogen atmosphere. The mixture was stirred at 70 °C for 2 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with dichloromethane / methanol to afford N-(8-bromoimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy-N-methyl-benzamide as a yellow solid.

[0725] LC-MS (Method A): Rt 0.93 min, m / z = 380 (M+H) +

[0726] Step A: Preparation of N-(8-cyano-imidazo[1,2-a]pyridin-6-yl)-4-fluoro-3-methoxy- N-methyl-benzamide Step B: Preparation of N-(3-bromo-8-cyano-imidazo[1,2-a]pyridin-6-yl)-4-fluoro-3- methoxy-N-methyl-benzamide

[0727]

[0728] To a solution of N-(8-bromoimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy-N- methyl-benzamide (Compound X-6) (0.200 g, 0.529 mmol) in dioxane (2.00 mL) was added acetamide (0.0625 g, 1.06 mmol), Xantphos Pd G2 (0.0470 g, 0.0529 mmol) and cesium carbonate (0.516 g, 1.59 mmol). The mixture was stirred at 100 °C under a N2atmosphere for 16 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with methanol / dichloromethane to afford N-(8-acetamidimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy-N-methyl- benzamide as a white solid.

[0729] LC-MS (Method A): Rt 1.24 min, m / z = 357 (M+H) +

[0730] ​ ​

[0731]

[0732] To a solution of N-(8-acetamidoimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3- methoxy-N-methyl-benzamide (0.130 g, 0.365 mmol) in dichloromethane (4.0 mL) under nitrogen at -30 °C was added N-bromosuccinimide (0.0714 g, 0.401 mmol) for 1 h. The mixture was diluted with water and extracted with ethyl acetate (50 mL). The organic layer was concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with dichloromethane / methanol to give N-(8-acetamido-3-bromo-imidazo[l,2-a]pyridin-6-yl)-4-fluoro-3- methoxy-N-methyl-benzamide as a white solid.

[0733] LC-MS (Method A): Rt 1.42 min, m / z = 435 (M+H) +

[0734] ​ ​

[0735] To a solution of N-(8-acetamido-3-bromo-imidazo[l,2-a]pyridin-6-yl)-4-fluoro-3- methoxy-N-methyl-benzamide (0.130 g, 0.299 mmol) in dioxane (4.00 mL) and water (1.00 mL) was added methyl N-[5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-2- pyridyl]carbamate (0.166 g, 0.597 mmol), l, l'-bis(diphenylphosphino)ferrocene- dichloropalladium(ll) (0.0217 g, 0.0299 mmol) and potassium carbonate (0.0832 g, 0.597 mmol). The mixture was stirred under nitrogen atmosphere at 50 °C for 2.5 h. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with dichloromethane / methanol to give methyl N-[5-[8-acetamido-6-[(4-fluoro-3-methoxy- benzoyl)-methyl-amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate as a white solid.

[0736] LC-MS (Method A): Rt 1.04 min, m / z = 507 (M+H) +

[0737] 1 H-NMR (400 MHz, DMSO-d 6ppm) δ = 10.44 (s, 1H), 10.16 (s, 1H), 8.35 (d, J = 2.4 Hz, 1H), 8.19 (s, 1H), 8.04 (d, J = 1.8 Hz, 1H), 7.97 (d, J = 8.7 Hz, 1H), 7.78 (s, 1H), 7.73 (d, J = 8.6 Hz, 1H), 7.24 (d, J = 8.3 Hz, 1H), 7.12-7.04 (m, 1H), 6.89 (s, 1H), 3.72 (s, 3H), 3.70 (s, 3H), 3.35 (s, 3H), 2.22 (s, 3H).

[0738] ​ ​

[0739]

[0740] ​ ​

[0741]

[0742] To a solution of N-(8-bromoimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy-N- methyl-benzamide (compound X-6) (0.200 g, 0.529 mmol) in N,N-dimethylformamide (3.00 mL) were added successively zinc cyanide (0.124 g, 1.06 mmol), (5-diphenylphosphanyl-9,9-dimethyl-xanthene-4-yl)-diphenyl-phosphane (0.0612 g, 0.106 mmol) and Pd2(dba)3(0.0484 g, 0.0529 mmol). The mixture was heated at 100 °C for 1 hour under nitrogen in a microwave reactor. The resulting mixture was then diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with dichloromethane / methanol to give N-(8-cyanoimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy-N-methyl- benzamide as a green solid.

[0743] LC-MS (Method A): Rt 0.97 min, m / z = 325 (M+H) +

[0744] ​ ​

[0745]

[0746] To a solution of N-(8-cyanoimidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy-N- methyl-benzamide (0.190 g, 0.586 mmol) in dichloromethane (3.0 mL) at -30 °C was added N-bromosuccinimide (0.104 g, 0.586 mmol) and the resulting mixture was stirred under nitrogen at -30 °C for 1 hour. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with petroleum ether / ethyl acetate to give N-(3-bromo-8-cyano-imidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy-N- methyl-benzamide as a yellow solid.

[0747] LC-MS (Method A): Rt 1.15 min, m / z = 403 (M+H) +

[0748] Step C: Preparation of N-[5-[8-cyano-6-[(4-fluoro-3-methoxy- benzoyl)-methyl-amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamic acid methyl ester (Compound 55) Example 16: Preparation of N-[5-[8-ethyl-6-[(4-fluoro-3-methoxy- benzoyl)-methyl-amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamic acid methyl ester (Compound 57)

[0749] To a solution of N-(3-bromo-8-cyano-imidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy- N-methyl-benzamide (0.130 g, 0.322 mmol) in dioxane (2.00 mL) and water (0.50 mL) was added methyl N-[5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (0.135 g, 0.484 mmol), l,l'-bis(diphenylphosphino)ferrocene- dichloropalladium(ll) (0.0236 g, 0.0322 mmol) and potassium carbonate (0.111 g, 0.806 mmol). The mixture was stirred under nitrogen at 50 °C for 1.5 hours and then concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with dichloromethane / methanol to give methyl N-[5-[8-cyano-6-[(4-fluoro-3-methoxy- benzoyl)-methyl-amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate as a yellow solid.

[0750] LC-MS (Method A): Rt 1.12 min, m / z = 475 (M+H) +

[0751] 1 H-NMR (400 MHz, DMSO-d 6ppm) δ = 8.17-8.10 (m, 2H), 7.95 (s, 1H), 7.85 (s, 1H), 7.82 (s, 1H), 7.65 (d, J = 1.8 Hz, 1H), 7.42 (d, J = 8.6 Hz, 1H), 7.12 (dd, J = 8.0, 2.0 Hz, 1H), 6.99 (dd, J = 10.6, 8.2 Hz, 1H), 6.79 (s, 1H), 3.88 (s, 3H), 3.86 (s, 3H), 3.47 (s, 3H).

[0752] Step A: Preparation of 6-nitro-8-vinyl-imidazo[l,2-a]pyridine Step B: Preparation of 8-ethylimidazo[l,2-a]pyridin-6-amine

[0753]

[0754] Step C: Preparation of 8-ethyl-N-methyl-imidazo[l,2-a]pyridin-6-amine

[0755]

[0756] To a mixture of 8-bromo-6-nitro-imidazo[l,2-a]pyridine (compound X-5) (1.00 g, 4.13 mmol) and trifluoro(vinyl)borohydride (0.784 g, 8.26 mmol) in pre-mixed dioxane / H20 (10:1, 20.0 mL) was added l,l'-bis(diphenylphosphino)ferrocene- dichloropalladium(ll) (0.302 g, 0.413 mmol) and potassium carbonate (1.14 g, 8.26 mmol). The mixture was stirred at 80 °C under nitrogen atmosphere for 8 hours. The resulting mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with petroleum ether / ethyl acetate to give 6-nitro-8-vinyl-imidazo[l,2-a]pyridine as a yellow solid.

[0757] LC-MS (Method A): Rt 1.09 min, m / z = 190 (M+H) +

[0758] Step D: Preparation of 3-bromo-8-ethyl-N-methyl-imidazo[l,2-a]pyridin-6-amine

[0759]

[0760] To a solution of 6-nitro-8-vinylimidazo[l,2-a]pyridine (0.280 g, 1.48 mmol) in methanol (5.0 mL) was added Pd / C (20%, 56 mg). The mixture was evacuated and backfilled with hydrogen three times, and then charged with hydrogen. The resulting mixture was stirred at room temperature for 4 hours. The mixture was then filtered through celite. The filtrate was concentrated under reduced pressure to give crude 8-ethylimidazo[l,2-a]pyridin-6-amine which was used directly in the next step without further purification.

[0761] LC-MS (Method A): Rt 0.22 min, m / z = 162 (M+H) +

[0762] Step E: Preparation of N-(3-bromo-8-ethyl-imidazo[l,2-a]pyridin-6-yl)-4- fluoro-3-methoxy-N-methyl-benzamide

[0763]

[0764] To a solution of 8-ethylimidazo[l,2-a]pyridin-6-amine (0.200 g, 1.24 mmol) in diethoxyethoxyethane (4.0 mL) was added 2,2,2-trifluoroacetic acid (0.00707 g, 0.0620 mmol). The solution was heated to reflux at 120 °C for 2 hours, cooled and concentrated to give a yellow liquid. To this solution was added absolute ethanol (4 mL) at 0 °C followed by sodium borate (0.141 g, 3.72 mmol). The resulting suspension was stirred at room temperature for 20 min, heated at 80 °C for 2 hours, cooled and concentrated to give a brown oil. The residue was partitioned between ether and water and the aqueous layer was extracted with ethyl acetate. The organic phases were combined, washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with petroleum ether / ethyl acetate to give 8-ethyl-N-methyl-imidazo[l,2-a]pyridin-6-amine as a yellow solid.

[0765] LC-MS (Method A): Rt 0.57 min, m / z = 176 (M+H) +

[0766] Step F: Preparation of N-[5-[8-ethyl-6-[(4-fluoro-3-methoxy- benzoyl)-methyl-amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamic acid methyl ester (Compound 57)

[0767]

[0768] To a solution of 8-ethyl-N-methyl-imidazo[l,2-a]pyridin-6-amine (0.200 g, 1.14 mmol) in dichloromethane (5.0 mL) was added N-bromosuccinimide (0.223 g, 1.26 mmol) at -30 °C and the mixture was stirred under nitrogen at -30 °C for 1 hour. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with dichloromethane / methanol to give 3-bromo-8-ethyl-N-methyl-imidazo[l,2-a]pyridin-6-amine as a yellow solid.

[0769] LC-MS (Method A): Rt 0.68 min, m / z = 255 (M+H) +

[0770] Biological Examples: ​

[0771]

[0772] To a mixture of 4-fluoro-3-methoxy-benzoic acid (0.113 g, 0.665 mmol) in N,N- dimethylformamide (5.00 mL) was added 1-methylimidazole (0.126 g, 1.53 mmol) and [chloro(dimethylamino)methylene]-dimethyl-ammonium hexafluorophosphate (0.215 g, 0.767 mmol) at room temperature. The solution was stirred for 5 min. Then 3-bromo-8-ethyl-N-methyl- imidazo[l,2-a]pyridin-6-amine (0.130 g, 0.512 mmol) was added portionwise. The resulting solution was stirred for 2 hours. The reaction mixture was diluted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with dichloromethane / methanol to give N-(3-bromo-8-ethyl-imidazo[l,2-a]pyridin-6-yl)-4-fluoro-3-methoxy-N-methyl- benzamide as a brown solid.

[0773] LC-MS (Method A): Rt 1.21 min, m / z = 408 (M+2H) 2+

[0774] ​ ​

[0775] To a solution of N-(3-bromo-8-ethyl-imidazo[l,2-a]pyridin-6-yl)-4-fluoro-3- methoxy-N-methyl-benzamide (0.130 g, 0.322 mmol) in dioxane (4.00 mL) and water (1.00 mL) was added methyl N-[5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-2- pyridyl]carbamate (0.134 g, 0.484 mmol), l,l'-bis(diphenylphosphino)ferrocene- dichloropalladium(ll) (0.0234 g, 0.0322 mmol) and potassium carbonate (0.133 g, 0.960 mmol). The mixture was stirred at 45 °C under nitrogen atmosphere for 2 hours and then concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with dichloromethane / methanol to give the desired compound which was further purified by trituration with acetonitrile / petroleum ether (1 :10) to give methyl N-[5-[8-ethyl-6-[(4-fluoro-3-methoxy- benzoyl)-methyl-amino]imidazo[l,2-a]pyridin-3-yl]-2-pyridyl]carbamate as a white solid.

[0776] LC-MS (Method A): Rt 0.96 min, m / z = 478 (M+H) +

[0777] 1 H-NMR (400 MHz, DMSO-d 6 , ppm) δ = 8.15 (s, 1H), 8.08 (d, J = 8.6 Hz, 1H), 7.84 (s, 1H), 7.66 (s, 1H), 7.61 (s, 1H), 7.39 (d, J = 8.2 Hz, 1H), 7.07 (d, J = 7.0 Hz, 1H), 7.01 (s, 1H), 6.96-6.91 (m, 1H), 6.84 (s, 1H), 3.85 (s, 3H), 3.79 (s, 3H), 3.46 (s, 3H), 3.10 (d, J = 7.4 Hz, 2H), 1.40 (t, J = 7.4 Hz, 3H).

[0778] ​

[0779] The fungicidal activity of the compounds of the present application has been tested as follows:

[0780] Phytophthora infestans / tomato / leaf disc preventive (late blight)

[0781] Tomato leaf disks were placed on water agar in multiwell plates (24 well format) and sprayed with formulated test compound diluted in water. One day after application, the leaf disks were inoculated with a spore suspension of the fungus. Inoculated leaf disks were incubated in a growth chamber under a light regime of 24h darkness followed by 12h light / 12h darkness at 16°C and 75% rh and the activity of the compounds was evaluated as the percentage of disease control compared to untreated when a suitable level of disease damage had developed in the untreated check leaf disks (5-7 days after application).

[0782] The following compounds gave at least 80% control of the pathogenic Pythium ultimum at 200 ppm: 1, 3, 5, 10, 11, 12, 13, 19, 21, 22, 23, 24, 25, 26, 37, 40, 41, 43, 45, 46, 47, 49, 51, 53, 54, 55, 56, 57, 58, 59, 60, 62

[0784] Grapevine Plasmopara viticola / Grape / Leaf disks preventive (Downy Mildew)

[0785] Grapevine leaf disks were placed on water agar medium in multiwell plates (24 well format) and sprayed with formulated test compound diluted in water. One day after application, the leaf disks were inoculated with a spore suspension of the fungus. Inoculated leaf disks were incubated in a growth chamber under a light regime of 12h light / 12h darkness at 19°C and 80% rh and the activity of the compounds was evaluated as the percentage of disease control compared to untreated when a suitable level of disease damage had developed in the untreated check leaf disks (6-8 days after application).

[0786] The following compounds gave at least 80% control of the pathogenic Pythium ultimum at 200 ppm: 1, 5, 10, 11, 12, 13, 25, 26, 27, 41, 45, 47, 49, 53, 54, 55, 56, 57, 58, 60

[0788] Pythium ultimum / Liquid culture (Seedling damping off)

[0789] Freshly grown fungal liquid culture mycelial fragments as well as oospores were mixed directly into nutrient broth (PDB (potato dextrose broth)). After placing the (DMSO) solution of test compound in microtiter plates (96 well format), the nutrient liquid medium containing the fungal mycelia / spore mixture was added. The test plates were incubated at 24°C and inhibition of growth was determined photometrically 2-3 days after application.

[0790] The following compounds gave at least 80% control of Pythium ultimum at 20 ppm when compared to untreated controls which showed extensive disease development under the same conditions:

[0791] 1, 2, 3, 4, 5, 6, 7, 10, 11, 12, 13, 14, 15, 17, 19, 21, 22, 23, 24, 25, 26, 27, 41, 43, 45, 47, 49, 53, 54, 55, 56, 57, 58, 59, 60, 62.

Claims

1. A compound having formula (I) Where Z is O or S, and preferably Z is O; A 1 It is CH or N; R 1a R 1b and R 1c Independently selected from hydrogen, hydroxyl, 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 Alkyl thioalkyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 Alkoxy, amino, C 2-4 alkenyl and -NHC(O)C 1-6 alkyl; A 2 Independently, it is CR 2 Or N, provided that there are no more than four A's. 2 If it is N, then no more than three A's are preferred. 2 If it is N, then no more than two A's are preferred. 2 If it is N, then no more than one A is preferred. 2 It is N, and more preferably five A's. 2 It is CR 2 ; R 2 Independently selected from hydrogen, hydroxyl, halogen, CN, C 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 group, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl thioalkyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 Alkyl carbonyl, amino, C 1-6 Alkylamino, diC 1-6 -alkylamino, and C 3-6 cycloalkylamino, wherein the C 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 group, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl thioalkyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 alkyl carbonyl, C 1-6 alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 Alkyl carbonyl, amino, C 1-6 Alkylamino, diC 1-6 -alkylamino, and C 3-6 Each of the cycloalkylamino groups may optionally be substituted by one to three independent substituents selected from the following: halogen, hydroxyl, and CN; R 4 Selected from 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 group, C 1-6 Alkoxy, C 1-6 Alkylthio-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 groups and CN, wherein the 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 group, C 1-6 Alkoxy, C 1-6 Alkylthio-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 optionally be substituted by one to three independent substituents selected from the following: halogens and CN; and R 5 Selected from 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, wherein the 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 Each of the alkoxyamino groups may optionally be substituted by one to three independent substituents selected from the following: halogens and CN; Or its salts or N-oxides.

2. The compound according to claim 1, wherein, R 1a R 1b and R 1c Independently selected from hydrogen and 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 2-4 alkenyl and C 1-6 Alkyl group.

3. The compound according to claim 1 or 2, wherein, R 1a R 1b and R 1c Independently selected from hydrogen and C 2-4 alkenyl and C 1-6 alkyl.

4. The compound according to claim 1, wherein, R 1a and R 1c It is hydrogen; and R 1b Selected from hydrogen, hydroxyl, 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 Alkoxy, amino, C 2-4 alkenyl and NHC(O)C 1-6 alkyl.

5. The compound according to any one of the preceding claims, wherein, R 2 Independently selected from hydrogen, hydroxyl, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 alkylaminocarbonyl, and C 1-6 alkyl carbonyl, wherein the C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 alkylaminocarbonyl, and C 1-6 Each of the alkyl carbonyl groups may optionally be substituted by one to three independent substituents selected from the following: halogen, hydroxyl, and CN.

6. The compound according to any one of the preceding claims, wherein, Four A's 2 It is CR 4 And an A 2 It is N.

7. The compound according to any one of the preceding claims, wherein, yes And preferably four A's 2 It is CR 2 .

8. The compound according to any one of claims 1 to 6, wherein, yes And preferably four A's 2 It is CR 2 .

9. The compound according to any one of claims 1 to 5, wherein, The five A's 2 It is CR 2 .

10. The compound according to claim 9, wherein, yes 11. The compound according to any one of the preceding claims, wherein, R 4 Selected from C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 Alkyl and C 1-6 Alkoxy, wherein the C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 Alkyl and C 1-6 Each of the alkoxy groups may optionally be substituted by one to three substituents independently selected from the following: halogens and CN.

12. The compound according to any one of the preceding claims, wherein, R 5 Selected from C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 Alkyl and C 1-6 Alkoxy C 1-6 Alkyl groups, wherein each of the groups is optionally substituted by one to three substituents independently selected from the following: halogens and CN.

13. A composition comprising an effective amount of the compound as described in any one of claims 1 to 12.

14. The composition according to claim 14, wherein, The composition further comprises at least one compound selected from the following: additional active ingredients, suitable formulation inert agents, carriers, adjuvants, and any mixtures thereof.

15. A method for combating, preventing or controlling plant pathogenic diseases, the method comprising applying to a plant pathogen, a site of a plant pathogen, a plant susceptible to a plant pathogen, or its plant propagation material an effective amount of a compound according to any one of claims 1 to 12, or a composition comprising a compound according to any one of claims 1 to 12, or a composition according to claim 13 or 14.

16. A compound having formula (II) Where Z is O or S, and preferably Z is O; R 1a R 1b and R 1c Independently selected from hydrogen, hydroxyl, 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 Alkyl thioalkyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 Alkoxy, amino, C 2-4 alkenyl and -NHC(O)C 1-6 Alkyl; and preferably, R 1a and R 1c It is hydrogen, and R 1b It can be selected from hydrogen, C 1-6 Alkyl, C 3-6 cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl and C 2-4 alkenyl; A 2 Independently, it is CR 2 Or N, provided that there are no more than four A's. 2 If it is N, then no more than three A's are preferred. 2 If it is N, then no more than two A's are preferred. 2 If it is N, then no more than one A is preferred. 2 It is N, and more preferably five A's. 2 It is CR 2 ; R 2 Independently selected from hydrogen, hydroxyl, halogen, CN, C 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 group, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl thioalkyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 Alkyl carbonyl, amino, C 1-6 Alkylamino, diC 1-6 -alkylamino, and C 3-6 cycloalkylamino, wherein the C 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 group, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl thioalkyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 alkyl carbonyl, C 1-6 alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 Alkyl carbonyl, amino, C 1-6 Alkylamino, diC 1-6 -alkylamino, and C 3-6 Each of the cycloalkylamino groups is optionally substituted by one to three substituents independently selected from the following: halogen, hydroxyl, and CN, and more preferably, R 2 Independently selected from hydrogen, hydroxyl, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 cycloalkyl, C 1-6 Alkyl thioalkyl, C 1-6 alkylsulfonyl, C 1-6 alkoxycarbonyl, C 1-6 alkylaminocarbonyl and diC 1-6 alkylaminocarbonyl, wherein the C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 cycloalkyl, C 1-6 Alkyl thioalkyl, C 1-6 alkylsulfonyl, C 1-6 alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 alkylaminocarbonyl, and C 1-6 Each of the alkyl carbonyl groups may optionally be substituted by one to three independent substituents selected from the following: halogen, hydroxyl, and CN; R 4 Selected from 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 group, C 1-6 Alkoxy, C 1-6 Alkylthio-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 groups and CN, wherein the 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 group, C 1-6 Alkoxy, C 1-6 Alkylthio-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 optionally be substituted by one to three independent substituents selected from the following: halogen and CN; and preferably R. 4 Selected from C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 Alkyl and C 1-6 Alkoxy, wherein the C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 Alkyl and C 1-6 Each of the alkoxy groups may optionally be substituted by one to three independent substituents selected from the following: halogens and CN; and X is Cl, Br, or I; Or its salts or N-oxides; or A compound having formula (X) Where Z is O or S, and preferably Z is O; R 1a R 1b and R 1c Independently selected from hydrogen, hydroxyl, 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 Alkyl thioalkyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 Alkoxy, amino, C 2-4 alkenyl and -NHC(O)C 1-6 Alkyl; and preferably, R 1a and R 1c It is hydrogen, and R 1b It can be selected from hydrogen, C 1-6 Alkyl, C 3-6 cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl and C 2-4 alkenyl; A 2 Independently, it is CR 2 Or N, provided that there are no more than four A's. 2 If it is N, then no more than three A's are preferred. 2 If it is N, then no more than two A's are preferred. 2 If it is N, then no more than one A is preferred. 2 It is N, and more preferably five A's. 2 It is CR 2 ; R 2 Independently selected from hydrogen, hydroxyl, halogen, CN, C 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 group, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl thioalkyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 Alkyl carbonyl, amino, C 1-6 Alkylamino, diC 1-6 -alkylamino, and C 3-6 cycloalkylamino, wherein the C 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 group, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl thioalkyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 alkyl carbonyl, C 1-6 alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 Alkyl carbonyl, amino, C 1-6 Alkylamino, diC 1-6 -alkylamino, and C 3-6 Each of the cycloalkylamino groups may optionally be substituted by one to three substituents independently selected from the following: halogen, hydroxyl, and CN; and more preferably, R 2 Independently selected from hydrogen, hydroxyl, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 cycloalkyl, C 1-6 Alkyl thioalkyl, C 1-6 alkylsulfonyl, C 1-6 alkoxycarbonyl, C 1-6 alkylaminocarbonyl and diC 1-6 alkylaminocarbonyl, wherein the C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 cycloalkyl, C 1-6 Alkyl thioalkyl, C 1-6 alkylsulfonyl, C 1-6 alkoxycarbonyl, C 1-6 alkylaminocarbonyl and diC 1-6 Each of the alkylamino carbonyl groups may optionally be substituted by one to three independent substituents selected from the following: halogen, hydroxyl, and CN; and R 4 Selected from 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 group, C 1-6 Alkoxy, C 1-6 Alkylthio-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 groups and CN, wherein the 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 group, C 1-6 Alkoxy, C 1-6 Alkylthio-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 optionally be substituted by one to three independent substituents selected from the following: halogen and CN; and preferably R. 4 Selected from C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 Alkyl and C 1-6 Alkoxy, wherein the C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 Alkyl and C 1-6 Each of the alkoxy groups may optionally be substituted by one to three independent substituents selected from the following: halogens and CN; Or its salts or N-oxides.

17. A compound having formula (XVII) Where A 1 It is CH or N, and preferably N; R 1a R 1b and R 1c Independently selected from hydrogen, hydroxyl, 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 Alkyl thioalkyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 Alkoxy, amino, C 2-4 alkenyl and -NHC(O)C 1-6 Alkyl; and preferably, R 1a and R 1c It is hydrogen, and R 1b It can be selected from hydrogen, C 1-6 Alkyl, C 3-6 cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl and C 2-4 alkenyl; and R 5 Selected from 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, wherein the 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 Each of the alkoxyamino groups may optionally be substituted by one to three independent substituents selected from the following: halogen and CN; preferably R. 5 Selected from C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 Alkyl and C 1-6 Alkoxy C 1-6 Alkyl groups, wherein each of the groups is optionally substituted by one to three substituents independently selected from the following: halogens and CN; Or its salts or N-oxides; or A compound having the formula (XVIII) Where A 1 It is CH or N, and preferably N; R 1a R 1b and R 1c Independently selected from hydrogen, hydroxyl, 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 Alkyl thioalkyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 Alkoxy, amino, C 2-4 alkenyl and -NHC(O)C 1-6 Alkyl; and preferably, R 1a and R 1c It is hydrogen, and R 1b It can be selected from hydrogen, C 1-6 Alkyl, C 3-6 cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl and C 2-4 alkenyl; R 4 Selected from 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 group, C 1-6 Alkoxy, C 1-6 Alkylthio-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 groups and CN, wherein the 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 group, C 1-6 Alkoxy, C 1-6 Alkylthio-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 optionally be substituted by one to three independent substituents selected from the following: halogen and CN; preferably R. 4 Selected from C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 Alkyl and C 1-6 Alkoxy, wherein the C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 Alkyl and C 1-6 Each of the alkoxy groups may optionally be substituted by one to three independent substituents selected from the following: halogens and CN; and R 5 Selected from 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, wherein the 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 Each of the alkoxyamino groups may optionally be substituted by one to three independent substituents selected from the following: halogen and CN; preferably R. 5 Selected from C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 Alkyl and C 1-6 Alkoxy C 1-6 Alkyl groups, wherein each of the groups is optionally substituted by one to three substituents independently selected from the following: halogens and CN; Or its salts or N-oxides.

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