Imidazo[1,2-a]pyridine derivatives

Abstract

The present invention relates to a compound of formula (I). [Formula 1] The present invention relates to a process and method for preparing a compound of formula (I) (wherein the formula, the substituents are as defined in claim 1), a pesticide composition comprising a compound of formula (I) as defined in claim 1, the preparation of such compositions, and the use of such compounds or compositions in agriculture or horticulture to control, prevent or control ectoparasitism of plants, harvested food crops, seeds or non-biological materials by plant pathogenic microorganisms, particularly fungi.

Description

Technical Field

[0001] The present invention relates to microbicidal activity, especially fungicidal activity, more specifically activity against oomycetes, for example microbicidal imidazo[1,2-a]pyridine derivatives as active ingredients. The present invention relates to the preparation of these imidazo[1,2-a]pyridine derivatives, intermediates useful for the preparation of these imidazo[1,2-a]pyridine derivatives, the preparation of these intermediates, pesticidal compositions containing at least one of the imidazo[1,2-a]pyridine derivatives, the preparation of these compositions and the use of imidazo[1,2-a]pyridine derivatives or compositions in agriculture or horticulture for controlling, preventing or protecting plants, harvested food crops, seeds or non-living materials from ectoparasitism by phytopathogenic microorganisms, especially fungi, more specifically oomycetes.

Summary of the Invention

Problems to be Solved by the Invention

[0002] Surprisingly, it has now been found that certain novel imidazo[1,2-a]pyridine derivatives have particularly advantageous fungicidal properties against oomycetes.

Means for Solving the Problems

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

Chemical Formula

[0004] In a second aspect, the present invention provides a pesticide composition comprising a compound of formula (I), more specifically, a pesticide composition comprising a fungicidally effective amount of a compound of formula (I). The composition may further comprise at least one compound selected from additional active ingredients, suitable inert ingredients, carriers, auxiliaries, and any mixtures thereof.

[0005] Compounds of formula (I) can be used to control plant pathogenic microorganisms. Therefore, to control plant pathogens, compounds of formula (I) according to the present invention, or compositions containing compounds of formula (I), can be applied directly to plant pathogens, habitats of plant pathogens, in particular plants susceptible to attack by plant pathogens, or plant reproductive materials.

[0006] Accordingly, in a third aspect, the present invention provides the use of a compound of formula (I) described herein, or a composition comprising a compound of formula (I), for eradicating, preventing, or controlling plant pathogens.

[0007] In a fourth aspect, the present invention provides a method for eradicating, preventing or controlling plant pathogens, comprising applying a compound of formula (I) described herein or a composition containing a compound of formula (I) to the plant pathogen, the habitat of the plant pathogen, in particular plants susceptible to damage by the plant pathogen, or plant reproductive material.

[0008] Compounds of formula (I) are particularly effective in eradicating, preventing, or controlling plant pathogenic fungi, especially oomycetes. Accordingly, in a fifth aspect, the present invention provides the use of compounds of formula (I) described herein, or compositions containing compounds of formula (I), for controlling plant pathogenic fungi, especially oomycetes.

[0009] In a sixth aspect, the present invention provides a method for eradicating, preventing, or controlling plant pathogenic diseases such as plant pathogenic fungi, comprising applying a compound of formula (I) described herein or a composition containing a compound of formula (I) to the plant pathogenic fungi or the habitat of the plant pathogenic fungi (particularly plants susceptible to damage from plant pathogenic fungi, particularly oomycetes) or to the plant's reproductive material.

[0010] When it is indicated that a certain group, for example an alkyl group, is substituted, this includes these groups that are part of other groups, such as the alkyl group in alkylthio. [Modes for carrying out the invention]

[0011] Definition: - The terms "halogen" or "halo" refer to fluorine (fluoro or F), chlorine (chloro or Cl), bromine (bromo or Br), or iodine (iod or I), preferably fluorine, chlorine, or bromine.

[0012] - The term "amino" refers to the -NH2 group.

[0013] -The term "alkyl" as used herein, either alone or as part of a chemical group, preferably refers to a linear or branched hydrocarbon having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 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 alkyl groups having 1 to 4 carbon atoms are preferred, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl.

[0014] -The term "alkenyl," either alone or as part of a chemical group, preferably represents a linear or branched hydrocarbon having 2 to 6 carbon atoms and at least one double bond, such as vinyl, 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl- 2-Pentenyl, 4-Methyl-2-Pentenyl, 3-Methyl-3-Pentenyl, 4-Methyl-3-Pentenyl, 1-Methyl-4-Pentenyl, 2-Methyl-4-Pentenyl, 3-Methyl-4-Pentenyl, 4-Methyl-4-Pentenyl, 1,1-Dimethyl-2-Butenyl, 1,1-Dimethyl-3-Butenyl, 1,2-Dimethyl-2-Butenyl, 1,2-Dimethyl-3-Butenyl, 1,3-Dimethyl-2-Butenyl This represents methyl-2-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, and 1-ethyl-2-methyl-2-propenyl. An alkenyl group having 2 to 4 carbon atoms is preferred, for example, 2-propenyl, 2-butenyl, or 1-methyl-2-propenyl.

[0015] -The term "alkynyl," either alone or as part of a chemical group, preferably represents a linear or branched hydrocarbon having 2 to 6 carbon atoms and at least one triple bond, such as 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl This represents 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-hexadinyl. Alkynnyls having 2 to 4 carbon atoms are preferred, for example, ethinyl, 2-propynyl, or 2-butynyl-2-propenyl.

[0016] - The term "haloalkyl" refers to an alkyl radical as generally defined above, which is substituted by one or more of the same or different halogen atoms, such as fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, or 2,2,2-trifluoroethyl.

[0017] - The term "cyanoalkyl" refers to an alkyl radical as generally defined above, which is substituted with one or more cyano groups.

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

[0019] - The term "halocycloalkyl" refers to a cycloalkyl ring, as generally defined above, that is substituted by one or more of the same or different halogen atoms.

[0020] - The term "cyanocycloalkyl" refers to a cycloalkyl radical, as generally defined above, that is substituted with one or more cyano groups.

[0021] - The term "alkoxy" is derived from the formula -OR a It refers to the base of, and in the formula, R a These are alkyl radicals as generally defined above. Examples of alkoxys include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy, and tert-butoxy. The term "alkoxyalkyl" refers to alkyl radicals substituted with the aforementioned alkoxy groups (as described above). Examples include methoxymethyl, methoxyethyl, ethoxymethyl, and propoxymethyl.

[0022] - The term "alkylsulfanyl" is derived from the formula -SR a It refers to the radical of, in the formula, R a This is an alkyl radical as generally defined above.

[0023] - The term "alkylsulfinyl" is derived from the formula -S(O)R a It refers to the radical of, in the formula, R a This is an alkyl radical as generally defined above.

[0024] - The term "alkylsulfonyl" is derived from the formula -S(O)2R a It refers to the radical of, in the formula, R a This is an alkyl radical as generally defined above.

[0025] - The term "alkoxycarbonyl" is derived from the formula R a This refers to the OC(O)- radical, and in the formula, R a This is an alkyl radical as generally defined above.

[0026] - The term "alkoxycarbonyl" is derived from the formula R a This refers to the OC(O)- radical, and in the formula, R a This is an alkyl radical as generally defined above.

[0027] - The term "alkylamino" is derived from the formula R a This refers to the NH- radical, and in the formula, R a This is an alkyl radical as generally defined above.

[0028] - The term "cycloalkylamino" is derived from the formula R a This refers to the NH- radical, and in the formula, R a This is a cycloalkyl radical as generally defined above.

[0029] - The term "alkoxyamino" is derived from the formula R a This refers to the NH- radical, and in the formula, R a This is an alkoxy radical as generally defined above.

[0030] - The term "alkylaminocarbonyl" is derived from the formula R a This refers to the NHC(O)- radical, and in the formula, R a This is an alkyl radical as generally defined above.

[0031] -Hydroxyl or hydroxyl represents the -OH group.

[0032] In relation to the present invention, the terms “to eradicate,” “to prevent,” or “to control,” and their variations thereof, mean reducing pathogenicity, more specifically plant pathogenicity, any undesirable effects such as fungi including oomycetes, exocytosis or attack on plants or plant-derived products, and pathogenic damage, to a level in which improvement is demonstrated.

[0033] As used herein, the term "effective amount" refers to the amount of a compound, its salt, or N-oxide that produces the desired effect through one or more applications.

[0034] The effective amount can be readily determined by those skilled in the art by observing the results obtained using known techniques and under similar circumstances. In determining the effective amount, several factors are considered, but are not limited to: the type of plant or derivative product to be applied; the pathogen being controlled and its life cycle; the specific compound to be applied; the type of application; and numerous other relevant circumstances, but are not limited to these.

[0035] Compounds of formula (I) having at least one basic center include, for example, strong inorganic acids such as mineral acids, such as perchloric acid, sulfuric acid, nitric acid, nitrite, phosphoric acid, or hydrohalic acid, and strong organic carboxylic acids such as unsubstituted or halogenated C. 1-4 Alkane carboxylic acids, such as acetic acid; saturated or unsaturated dicarboxylic acids, such as oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, or phthalic acid; hydroxycarboxylic acids, such as ascorbic acid, lactic acid, malic acid, tartaric acid, or citric acid; or benzoic acid, together with organic sulfonic acids, such as unsubstituted or halogenated C 1-4Compounds of formula (I) having at least one acidic group can form salts with, for example, alkanes or aryl sulfonic acids, such as methane or p-toluenesulfonic acid. For example, salts with a base, such as mineral salts, such as alkali metal or alkaline earth metal salts, such as sodium, potassium or magnesium salts, or salts with monamines or organic amines, such as morpholine, piperidine, pyrrolidine, mono-, di- or tri-lower alkylamines, such as ethyl-, diethyl-, triethyl or dimethylpropylamine, or mono-, di or trihydroxy lower alkylamines, such as mono-, di- or triethanolamine.

[0036] In each case, the compound of formula (I) according to the present invention exists in a free form, an oxidized form as an N-oxide, a covalently hydrated form, or a salt hydrate, for example, an agrochemically usable or agrochemically acceptable form. The N-oxide is an oxidized form of a tertiary amine or an oxidized form of a nitrogen-containing heteroaromatic compound. These are described, for example, in the book "Heterocyclic N-oxides" by A. Albini and S. Pietra, CRC Press, Boca Raton 1991. The compound of formula (I) according to the present invention also includes hydrates that may be formed during salt formation.

[0037] The compounds of formula (I) according to the present invention also include hydrates that may be formed during salt formation.

[0038] In further embodiments, the present invention relates to a compound of formula (I), wherein R 1a , R 1b and R 1c However, hydrogen, 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 Alkikenyl and C 1-6Compounds are provided that are independently selected from alkoxys.

[0039] In a particular embodiment, R 1a , R 1b and R 1c is hydrogen, C 2-4 Alkenyl and C 1-6 It can be selected independently of alkyl groups.

[0040] In another specific embodiment, R 1a and R 1c It can be hydrogen, R 1b These are hydrogen, hydroxyl, halogen, CN, 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 1-6 Alkoxy, amino, C 2-4 Alkenyl and NHC(O)C 1-6 Alkyl can be selected, more preferably R 1b is hydrogen, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl and C 2-4 It can be selected from alkykenil.

[0041] In further embodiments, the present invention relates to a compound of formula (I), wherein R 2 However, 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 Independently selected from alkylcarbonyls, where C 1-6 Alkyl, C1-6 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 alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; preferably, R 2 However, 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 Selected independently of alkoxy, where 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 alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; more preferably, R 2 However, hydrogen, halogen, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Compounds are provided that are independently selected from alkoxycarbonyl and CN.

[0042] In a further embodiment, the compound of formula (I) according to the present invention, wherein four A 2 CR 4 And one A 2 A compound is provided in which is N.

[0043] In further embodiments, the compound of formula (I) according to the present invention, wherein, [ka] but [ka] Preferably, four A 2 CR 2 A compound is provided.

[0044] In further embodiments, the compound of formula (I) according to the present invention, wherein, [ka] but [ka] Preferably, four A 2 CR 2 A compound is provided.

[0045] In a further embodiment, the compound of formula (I) according to the present invention, wherein five A 2 CR 2 Preferably, [ka] but [ka] A compound is provided.

[0046] In a particular embodiment, in the formula [ka] teeth [ka] And R 2 This is as defined in the present invention, and preferably R 2These are hydrogen, hydroxyl, halogen, CN, and 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 Independently selected from alkylcarbonyls, where 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 alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; preferably, R 2 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 Selected independently of alkoxy, where 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 alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; more preferably, R 2 is hydrogen, halogen, C 1-6 Alkyl, C 1-6 Alkoxy, C1-6 Alkoxy-C 1-6 Alkyl, C 1-6 It is independently selected from alkoxycarbonyl and CN.

[0047] In further embodiments, the present invention relates to a compound of formula (I), wherein R 4 However, 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 Selected from alkoxy, where 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 Compounds are provided in which each alkoxy group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN.

[0048] In further embodiments, the compound of formula (I) according to the present invention is R 5 However, 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 Compounds are provided which are selected from alkyl groups, where each of the groups may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN.

[0049] In a particular embodiment, the compound of formula (I) according to the present invention, wherein the formula includes, Z is O; A 1 is CH or N, more preferably N; R 1a , R 1b and R1c However, 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 Independently selected from alkyl groups, preferably R 1a , R 1b and R 1c is hydrogen, C 2-4 Alkenyl and C 1-6 Selected independently of alkyl; Five A's 2 CR 2 And R 2 However, 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 Independently selected from alkylcarbonyls, where 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 alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; preferably, R 2 However, hydrogen, halogen, CN, C 1-6 Alkyl, C1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl and C 1-6 Alkoxy-C 1-6 Selected independently of alkoxy, where 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 alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; more preferably, R 2 However, hydrogen, halogen, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Selected independently from alkyl and CN; R 4 However, 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 Selected from alkoxy, where 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 alkoxy group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN; R 5 However, 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 1-6Compounds are provided which are selected from alkyl groups, where each of the groups may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN.

[0050] In a preferred embodiment, [ka] teeth [ka] And R 2 This is as defined in the present invention, and preferably R 2 These are hydrogen, hydroxyl, halogen, CN, and 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 Independently selected from alkylcarbonyls, where 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 alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; preferably, R 2 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl and C1-6 Alkoxy-C 1-6 Selected independently of alkoxy, where 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 alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; more preferably, R 2 is hydrogen, halogen, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 It is independently selected from alkoxycarbonyl and CN.

[0051] In further embodiments, the compounds according to the present invention are selected from the following: Methyl N-[5-[6-[(4-chloro-3-methoxybenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-cyano-3-methylbenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(2-methoxypyridine-4-carbonyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-cyano-3-fluoro-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-cyano-3-methoxybenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[cyanomethyl-(4-fluorobenzoyl)amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[cyanomethyl-(4-fluoro-3-methoxy-benzoyl)amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(2-methoxypyridine-4-carbonyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-cyano-3-methoxy-benzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-cyano-3-ethoxy-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-(4-fluoro-3-methylbenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-(3,4-difluorobenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-(4-fluoro-3-methoxybenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-(4-fluoro-3-methoxy-benzoyl)-(2-methoxyethyl)amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-cyano-3-fluoro-benzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-cyano-3-ethoxy-benzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-cyano-3-methylbenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-chloro-3-methoxybenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(3-ethoxy-4-fluoro-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-fluorobenzoyl)-(2-methoxyethyl)amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-fluoro-3-methyl-benzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-(3,4-difluorobenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(3-ethoxy-4-fluoro-benzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-fluorobenzoyl)-(methoxymethyl)amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-(methoxymethyl)amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[4-[6-[(4-chlorobenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]phenyl]carbamate; N-[3-[6-(ethylcarbamoylamino)-3-pyridyl]-8-methylimidazo[1,2-a]pyridin-6-yl]-4-fluoro-3-methoxy-N-methylbenzamide; N-[3-[4-(cyclopropanecarbonylamino)phenyl]-8-methylimidazo[1,2-a]pyridine-6-yl]-4-fluoro-3-methoxy-N-methylbenzamide; 4-Fluoro-3-methoxy-N-[3-[4-(2-methoxyacetyl)amino]phenyl]-8-methylimidazo[1,2-a]pyridine-6-yl]-N-methylbenzamide; Methyl N-[4-[6-[(4-fluoro-3-methoxybenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]phenyl]carbamate; N-[3-[4-acetamidophenyl)-8-methylimidazo[1,2-a]pyridine-6-yl]-4-fluoro-3-methoxy-N-methylbenzamide; N-[3-(6-acetamido-3-pyridyl)-8-methylimidazo[1,2-a]pyridine-6-yl]-4-fluoro-3-methoxy-N-methylbenzamide; Methyl 4-[[3-[6-(methoxycarbonylamino)-3-pyridyl]-8-methylimidazo[1,2-a]pyridine-6-yl]methylcarbamoyl]-2-methylbenzoate; Methyl 5-fluoro-2-[[3-[6-(methoxycarbonylamino)-3-pyridyl]-8-methylimidazo[1,2-a]pyridin-6-yl]methylcarbamoyl]benzoate; Methyl 5-[[3-[6-(methoxycarbonylamino)-3-pyridyl]-8-methylimidazo[1,2-a]pyridin-6-yl]methylcarbamoyl]pyridin-2-carboxylate; Methyl N-[5-[6-[(6-methoxypyridine-2-carbonyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(5-methoxypyridine-2-carbonyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(2-fluoro-4-methoxy-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl 2-[[3-[6-(methoxycarbonylamino)-3-pyridyl]-8-methylimidazo[1,2-a]pyridin-6-yl]methylcarbamoyl]benzoate; Methyl N-[5-[6-[(4-chloro-3-methylbenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(5-cyano-4-methylpyridine-2-carbonyl)-methyl-amino]-8-methylimidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(6-fluoro-5-methylpyridine-3-carbonyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(6-methoxypyridine-3-carbonyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-fluorobenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[8-methyl-6-[methyl-(2-methylsulfanylpyridine-3-carbonyl)amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-cyanobenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(3-fluoro-4-methylbenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-chlorobenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(3-chloro-4-cyanobenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(6-cyanopyridine-3-carbonyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(5-cyano-2-methylbenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(3-methoxybenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(2,4-methoxybenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[8-cyano-6-[(4-fluoro-3-methoxybenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[8-cyclopropyl-6-[(4-fluoro-3-methoxybenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[8-ethyl-6-[(4-fluoro-3-methoxybenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[8-buta-3-enyl-6-[(4-fluoro-3-methoxybenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[8-acetamido-6-[(4-fluoro-3-methoxybenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[8-bromo-6-[(4-fluoro-3-methoxybenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[2-cyanoethyl-(4-fluorobenzoyl)amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate; and Methyl N-[5-[6-[2-cyanoethyl-(4-fluoro-3-methoxy-benzoyl)amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate.

[0052] The methods according to the present invention have advantageous properties for protecting plants from pathogenic attacks or ectoparasites that cause disease and damage to plants, such as plant pathogenic fungi, particularly oomycetes, and in the case of plants in particular, the present invention can control, limit or prevent pathogenic damage to plants, parts of plants, plant propagation materials and / or grown plants.

[0053] The compounds listed in Tables 1.1 to 1.144 below illustrate specific compounds of the present invention.

[0054] Table 1.1 shows equation (Ia) [ka] We provide 660 compounds E1.1 to E1.660, in which R 1b H is A1 CH is A 2a is N, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0055] [Table 1-1]

[0056] [Table 1-2]

[0057] [Table 1-3]

[0058] [Table 1-4]

[0059] [Table 1-5]

[0060] [Table 1-6]

[0061] [Table 1-7]

[0062] [Table 1-8]

[0063] [Table 1-9]

[0064] Table 1-10

[0065] Table 1-11

[0066] Table 1-12

[0067] Table 1-13

[0068] Table 1-14

[0069] Table 1-15

[0070] Table 1-16

[0071] Table 1-17

[0072] Table 1-18

[0073] Table 1-19

[0074] Table 1-20

[0075] Table 1-21

[0076] Table 1-22

[0077] Table 1-23

[0078] Table 1-24

[0079] Table 1-25

[0080] Table 1-26

[0081] Table 1-27

[0082] Table 1-28

[0083] Table 1-29

[0084] [Table 1-30]

[0085] [Table 1-31]

[0086] [Table 1-32]

[0087] [Table 1-33]

[0088] [Table 1-34]

[0089] [Table 1-35]

[0090] Table 1.2 provides 660 compounds E2.1 to E2.660 of formula (Ia), where R 1b H is A 1 CH is A 2a CH is, R 2 , A 2b , R 4 , R 5 This is as defined in Table Z.

[0091] Table 1.3 provides 660 compounds E3.1 to E3.660 of formula (Ia), where R 1b H is A 1 CH is A 2a is CF, R 2 , A 2b , R 4 , R 5 This is as defined in Table Z.

[0092] Table 1.4 provides 660 compounds E4.1 to E4.660 of formula (Ia), where R 1b H is A 1 CH is A 2a is CCl, and R 2 , A 2b , R 4 , R 5 This is as defined in Table Z.

[0093] Table 1.5 provides 660 compounds E5.1 to E5.660 of formula (Ia), where R 1b H is A 1 CH is A 2a is CBr, and R 2 , A 2b , R 4 , R 5 This is as defined in Table Z.

[0094] Table 1.6 provides 660 compounds E6.1 to E6.660 of formula (Ia), where R 1b H is A 1 CH is A 2a It is CCH3, and R 2 , A 2b , R 4 , R 5 This is as defined in Table Z.

[0095] Table 1.7 provides 660 compounds E7.1 to E7.660 of formula (Ia), where R 1b H is A 1 CH is A 2a It is CCH2CH3, and R 2 , A 2b , R 4 , R 5 This is as defined in Table Z.

[0096] Table 1.8 provides 660 compounds E8.1 to E8.660 of formula (Ia), where R 1b H is A 1 CH is A 2a It is CCN, and R 2 , A2b , R 4 , R 5 This is as defined in Table Z.

[0097] Table 1.9 provides 660 compounds E9.1 to E9.660 of formula (Ia), where R 1b H is A 1 CH is A 2a It is COCH3, and R 2 , A 2b , R 4 , R 5 This is as defined in Table Z.

[0098] Table 1.10 provides 660 compounds E10.1 to E10.660 of formula (Ia), where R 1b H is A 1 is N, and A 2a is N, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0099] Table 1.11 provides 660 compounds E11.1 to E11.660 of formula (Ia), where R 1b H is A 1 is N, and A 2a CH is, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0100] Table 1.12 provides 660 compounds E12.1 to E12.660 of formula (Ia), where R 1b H is A 1 is N, and A 2a is CF, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0101] Table 1.13 provides 660 compounds E13.1 to E13.660 of formula (Ia), where R 1b H is A 1 is N, and A 2a is CClF, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0102] Table 1.14 provides 660 compounds E14.1 to E14.660 of formula (Ia), where R 1b H is A 1 is N, and A 2a is CBr, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0103] Table 1.15 provides 660 compounds E15.1 to E15.660 of formula (Ia), where R 1b H is A 1 is N, and A 2a It is CCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0104] Table 1.16 provides 660 compounds E16.1 to E16.660 of formula (Ia), where R 1b H is A 1 is N, and A 2a It is CCH2CH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0105] Table 1.17 provides 660 compounds E17.1 to E17.660 of formula (Ia), where R 1b H is A 1 is N, and A 2a It is CCN, and R 2 , A2b , R 4 , R 5 This is defined in Table Z.

[0106] Table 1.18 provides 660 compounds E18.1 to E18.660 of formula (Ia), where R 1b H is A 1 is N, and A 2a It is COCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0107] Table 1.19 provides 660 compounds E19.1 to E19.660 of formula (Ia), where R 1b It is CH3, and A 1 CH is A 2a is N, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0108] Table 1.20 provides 660 compounds E20.1 to E20.660 of formula (Ia), where R 1b It is CH3, and A 1 CH is A 2a CH is, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0109] Table 1.21 provides 660 compounds E21.1 to E21.660 of formula (Ia), where R 1b It is CH3, and A 1 CH is A 2a is CF, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0110] Table 1.22 provides 660 compounds E22.1 to E22.660 of formula (Ia), where R 1b It is CH3, and A 1 CH is A 2a is CCl, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0111] Table 1.23 provides 660 compounds E23.1 to E23.660 of formula (Ia), where R 1b It is CH3, and A 1 CH is A 2a is CBr, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0112] Table 1.24 provides 660 compounds E24.1 to E24.660 of formula (Ia), where R 1b It is CH3, and A 1 CH is A 2a It is CCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0113] Table 1.25 provides 660 compounds E25.1 to E25.660 of formula (Ia), where R 1b It is CH3, and A 1 CH is A 2a It is CCH2CH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0114] Table 1.26 provides 660 compounds E26.1 to E26.660 of formula (Ia), where R 1b It is CH3, and A 1 CH is A 2a It is CCN, and R2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0115] Table 1.27 provides 660 compounds E27.1 to E27.660 of formula (Ia), where R 1b It is CH3, and A 1 CH is A 2a It is COCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0116] Table 1.28 provides 660 compounds E28.1 to E28.660 of formula (Ia), where R 1b It is CH3, and A 1 is N, and A 2a is N, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0117] Table 1.29 provides 660 compounds E29.1 to E29.660 of formula (Ia), where R 1b It is CH3, and A 1 is N, and A 2a CH is, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0118] Table 1.30 provides 660 compounds E30.1 to E30.660 of formula (Ia), where R 1b It is CH3, and A 1 is N, and A 2a is CF, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0119] Table 1.31 provides 660 compounds E31.1 to E31.660 of formula (Ia), where R 1b It is CH3, and A 1 is N, and A 2a is CCl, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0120] Table 1.32 provides 660 compounds E32.1 to E32.660 of formula (Ia), where R 1b It is CH3, and A 1 is N, and A 2a is CBr, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0121] Table 1.33 provides 660 compounds E33.1 to E33.660 of formula (Ia), where R 1b It is CH3, and A 1 is N, and A 2a It is CCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0122] Table 1.34 provides 660 compounds E34.1 to E34.660 of formula (Ia), where R 1b It is CH3, and A 1 is N, and A 2a It is CCH2CH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0123] Table 1.35 provides 660 compounds E35.1 to E35.660 of formula (Ia), where R 1b It is CH3, and A 1 is N, and A 2a It is CCN, and R 2, A 2b , R 4 , R 5 This is defined in Table Z.

[0124] Table 1.36 provides 660 compounds E36.1 to E36.660 of formula (Ia), where R 1b It is CH3, and A 1 is N, and A 2a It is COCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0125] Table 1.37 provides 660 compounds E37.1 to E37.660 of formula (Ia), where R 1b It is CH2CH3, and A 1 CH is A 2a is N, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0126] Table 1.38 provides 660 compounds E38.1 to E38.660 of formula (Ia), where R 1b It is CH2CH3, and A 1 CH is A 2a CH is, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0127] Table 1.39 provides 660 compounds E39.1 to E39.660 of formula (Ia), where R 1b It is CH2CH3, and A 1 CH is A 2a is CF, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0128] Table 1.40 provides 660 compounds E40.1 to E40.660 of formula (Ia), where R 1b It is CH2CH3, and A 1 CH is A 2a is CCl, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0129] Table 1.41 provides 660 compounds E41.1 to E41.660 of formula (Ia), where R 1b It is CH2CH3, and A 1 CH is A 2a is CBr, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0130] Table 1.42 provides 660 compounds E42.1 to E42.660 of formula (Ia), where R 1b It is CH2CH3, and A 1 CH is A 2a It is CCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0131] Table 1.43 provides 660 compounds E43.1 to E43.660 of formula (Ia), where R 1b It is CH2CH3, and A 1 CH is A 2a It is CCH2CH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0132] Table 1.44 provides 660 compounds E44.1 to E44.660 of formula (Ia), where R 1b It is CH2CH3, and A 1 CH is A 2aIt is CCN, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0133] Table 1.45 provides 660 compounds E45.1 to E45.660 of formula (Ia), where R 1b It is CH2CH3, and A 1 CH is A 2a It is COCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0134] Table 1.46 provides 660 compounds E46.1 to E46.660 of formula (Ia), where R 1b It is CH2CH3, and A 1 is N, and A 2a is N, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0135] Table 1.47 provides 660 compounds E47.1 to E47.660 of formula (Ia), where R 1b It is CH2CH3, and A 1 is N, and A 2a CH is, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0136] Table 1.48 provides 660 compounds E48.1 to E48.660 of formula (Ia), where R 1b It is CH2CH3, and A 1 is N, and A 2a is CF, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0137] Table 1.49 provides 660 compounds E49.1 to E49.660 of formula (Ia), where R 1b It is CH2CH3, and A 1 is N, and A 2a is CCl, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0138] Table 1.50 provides 660 compounds E50.1 to E50.660 of formula (Ia), where R 1b It is CH2CH3, and A 1 is N, and A 2a is CBr, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0139] Table 1.51 provides 660 compounds E51.1 to E51.660 of formula (Ia), where R 1b It is CH2CH3, and A 1 is N, and A 2a It is CCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0140] Table 1.52 provides 660 compounds E52.1 to E52.660 of formula (Ia), where R 1b It is CH2CH3, and A 1 is N, and A 2a It is CCH2CH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0141] Table 1.53 provides 660 compounds E53.1 to E53.660 of formula (Ia), where R 1b It is CH2CH3, and A 1 is N, and A2a It is CCN, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0142] Table 1.54 provides 660 compounds E54.1 to E54.660 of formula (Ia), where R 1b It is CH2CH3, and A 1 is N, and A 2a It is COCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0143] Table 1.55 provides 660 compounds E55.1 to E55.660 of formula (Ia), where R 1b It is CH2OCH3, and A 1 CH is A 2a is N, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0144] Table 1.56 provides 660 compounds E56.1 to E56.660 of formula (Ia), where R 1b It is CH2OCH3, and A 1 CH is A 2a CH is, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0145] Table 1.57 provides 660 compounds E57.1 to E57.660 of formula (Ia), where R 1b It is CH2OCH3, and A 1 CH is A 2a is CF, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0146] Table 1.58 provides 660 compounds E58.1 to E58.660 of formula (Ia), where R 1b It is CH2OCH3, and A 1 CH is A 2a is CCl, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0147] Table 1.59 provides 660 compounds E59.1 to E59.660 of formula (Ia), where R 1b It is CH2OCH3, and A 1 CH is A 2a is CBr, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0148] Table 1.60 provides 660 compounds E60.1 to E60.660 of formula (Ia), where R 1b It is CH2OCH3, and A 1 CH is A 2a It is CCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0149] Table 1.61 provides 660 compounds E61.1 to E61.660 of formula (Ia), where R 1b It is CH2OCH3, and A 1 CH is A 2a It is CCH2CH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0150] Table 1.62 provides 660 compounds E62.1 to E62.660 of formula (Ia), where R 1b It is CH2OCH3, and A1 CH is A 2a It is CCN, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0151] Table 1.63 provides 660 compounds E63.1 to E63.660 of formula (Ia), where R 1b It is CH2OCH3, and A 1 CH is A 2a It is COCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0152] Table 1.64 provides 660 compounds E64.1 to E64.660 of formula (Ia), where R 1b It is CH2OCH3, and A 1 is N, and A 2a is N, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0153] Table 1.65 provides 660 compounds E65.1 to E65.660 of formula (Ia), where R 1b It is CH2OCH3, and A 1 is N, and A 2a CH is, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0154] Table 1.66 provides 660 compounds E66.1 to E66.660 of formula (Ia), where R 1b It is CH2OCH3, and A 1 is N, and A 2a is CF, R 2 , A 2b , R 4 , R 5It is as defined in Table Z.

[0155] Table 1.67 provides 660 compounds E67.1 to E67.660 of formula (Ia), wherein R 1b is CH2OCH3, and A 1 is N, and A 2a is CCl, and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0156] Table 1.68 provides 660 compounds E68.1 to E68.660 of formula (Ia), wherein R 1b is CH2OCH3, and A 1 is N, and A 2a is CBr, and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0157] 0002886Table 1.69 provides 660 compounds E69.1 to E69.660 of formula (Ia), wherein R 1b is CH2OCH3, and A 1 is N, and A 2a is CCH3, and R 2 , A 2b , R 4 , R 5 [END]]is as defined in Table Z.

[0158] Table 1.70 provides 660 compounds E70.1 to E70.660 of formula (Ia), wherein R 1b [[ID=^0]]is CH2OCH3, and A 1 is N, and A 2a is CCH2CH3, and R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0159] Table 1.71 provides 660 compounds E71.1 to E71.660 of formula (Ia), wherein R1b It is CH2OCH3, and A 1 is N, and A 2a It is CCN, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0160] Table 1.72 provides 660 compounds E72.1 to E72.660 of formula (Ia), where R 1b It is CH2OCH3, and A 1 is N, and A 2a It is COCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0161] Table 1.73 provides 660 compounds E73.1 to E73.660 of formula (Ia), where R 1b It is cyclopropyl, and A 1 CH is A 2a is N, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0162] Table 1.74 provides 660 compounds E74.1 to E74.660 of formula (Ia), where R 1b It is cyclopropyl, and A 1 CH is A 2a CH is, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0163] Table 1.75 provides 660 compounds E75.1 to E75.660 of formula (Ia), where R 1b It is cyclopropyl, and A 1 CH is A 2a is CF, R 2 , A 2b , R 4, R 5 is as defined in Table Z.

[0164] Table 1.76 provides 660 compounds E76.1 to E76.660 of formula (Ia), wherein R 1b is cyclopropyl, A 1 is CH, A 2a is CCl, R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0165] Table 1.77 provides 660 compounds E77.1 to E77.660 of formula (Ia), wherein R 1b is cyclopropyl, A 1 is CH, A 2a is CBr, R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0166] Table 1.78 provides 660 compounds E78.1 to E78.660 of formula (Ia), wherein R 1b is cyclopropyl, A 1 is CH, A 2a is CCH3, R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0167] Table 1.79 provides 660 compounds E79.1 to E79.660 of formula (Ia), wherein R 1b is cyclopropyl, A 1 is CH, A 2a is CCH2CH3, R 2 , A 2b , R 4 , R 5 is as defined in Table Z.

[0168] Table 1.80 provides 660 compounds E80.1 to E80.660 of formula (Ia), where R 1b It is cyclopropyl, and A 1 CH is A 2a It is CCN, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0169] Table 1.81 provides 660 compounds E81.1 to E81.660 of formula (Ia), where R 1b It is cyclopropyl, and A 1 CH is A 2a It is COCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0170] Table 1.82 provides 660 compounds E82.1 to E82.660 of formula (Ia), where R 1b It is cyclopropyl, and A 1 is N, and A 2a is N, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0171] Table 1.83 provides 660 compounds E83.1 to E83.660 of formula (Ia), where R 1b It is cyclopropyl, and A 1 is N, and A 2a CH is, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0172] Table 1.84 provides 660 compounds E84.1 to E84.660 of formula (Ia), where R 1b It is cyclopropyl, and A 1 is N, and A 2ais CF, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0173] Table 1.85 provides 660 compounds E85.1 to E85.660 of formula (Ia), where R 1b It is cyclopropyl, and A 1 is N, and A 2a is CCl, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0174] Table 1.86 provides 660 compounds E86.1 to E86.660 of formula (Ia), where R 1b It is cyclopropyl, and A 1 is N, and A 2a is CBr, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z. This is defined in Table Z.

[0175] Table 1.87 provides 660 compounds E87.1 to E87.660 of formula (Ia), where R 1b It is cyclopropyl, and A 1 is N, and A 2a It is CCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z. This is defined in Table Z.

[0176] Table 1.88 provides 660 compounds E88.1 to E88.660 of formula (Ia), where R 1b It is cyclopropyl, and A 1 is N, and A 2a It is CCH2CH3, and R 2 , A 2b , R 4 , R 5This is defined in Table Z. This is defined in Table Z.

[0177] Table 1.89 provides 660 compounds E89.1 to E89.660 of formula (Ia), where R 1b It is cyclopropyl, and A 1 is N, and A 2a It is CCN, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z. This is defined in Table Z.

[0178] Table 1.90 provides 660 compounds E90.1 to E90.660 of formula (Ia), where R 1b It is cyclopropyl, and A 1 is N, and A 2a It is COCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0179] Table 1.91 provides 660 compounds E91.1 to E91.660 of formula (Ia), where R 1b It is CH2 cyclopropyl, and A 1 CH is A 2a is N, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0180] Table 1.92 provides 660 compounds E92.1 to E92.660 of formula (Ia), where R 1b It is CH2 cyclopropyl, and A 1 CH is A 2a CH is, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0181] Table 1.93 provides 660 compounds E93.1 to E93.660 of formula (Ia), where R 1b It is CH2 cyclopropyl, and A 1 CH is A 2a is CF, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0182] Table 1.94 provides 660 compounds E94.1 to E94.660 of formula (Ia), where R 1b It is CH2 cyclopropyl, and A 1 CH is A 2a is CCl, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0183] Table 1.95 provides 660 compounds E95.1 to E95.660 of formula (Ia), where R 1b It is CH2 cyclopropyl, and A 1 CH is A 2a is CBr, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0184] Table 1.96 provides 660 compounds E96.1 to E96.660 of formula (Ia), where R 1b It is CH2 cyclopropyl, and A 1 CH is A 2a It is CCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0185] Table 1.97 provides 660 compounds E97.1 to E97.660 of formula (Ia), where R 1b It is CH2 cyclopropyl, and A 1 CH is A2a It is CCH2CH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0186] Table 1.98 provides 660 compounds E98.1 to E98.660 of formula (Ia), where R 1b It is CH2 cyclopropyl, and A 1 CH is A 2a It is CCN, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0187] Table 1.99 provides 660 compounds E99.1 to E99.660 of formula (Ia), where R 1b It is CH2 cyclopropyl, and A 1 CH is A 2a It is COCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0188] Table 1.100 provides 660 compounds E100.1 to E100.660 of formula (Ia), where R 1b It is CH2 cyclopropyl, and A 1 is N, and A 2a is N, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0189] Table 1.101 provides 660 compounds E101.1 to E101.660 of formula (Ia), where R 1b It is CH2 cyclopropyl, and A 1 is N, and A 2a CH is, R 2 , A 2b , R 4 , R 5This is defined in Table Z.

[0190] Table 1.102 provides 660 compounds E102.1 to E102.660 of formula (Ia), where R 1b It is CH2 cyclopropyl, and A 1 is N, and A 2a is CF, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0191] Table 1.103 provides 660 compounds E103.1 to E103.660 of formula (Ia), where R 1b It is CH2 cyclopropyl, and A 1 is N, and A 2a is CCl, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0192] Table 1.104 provides 660 compounds E104.1 to E104.660 of formula (Ia), where R 1b It is CH2 cyclopropyl, and A 1 is N, and A 2a is CBr, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0193] Table 1.105 provides 660 compounds E105.1 to E105.660 of formula (Ia), where R 1b It is CH2 cyclopropyl, and A 1 is N, and A 2a It is CCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0194] Table 1.106 provides 660 compounds E106.1 to E106.660 of formula (Ia), where R 1b It is CH2 cyclopropyl, and A 1 is N, and A 2a It is CCH2CH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0195] Table 1.107 provides 660 compounds E107.1 to E107.660 of formula (Ia), where R 1b It is CH2 cyclopropyl, and A 1 is N, and A 2a It is CCN, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0196] Table 1.108 provides 660 compounds E108.1 to E108.660 of formula (Ia), where R 1b It is CH2 cyclopropyl, and A 1 is N, and A 2a It is COCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0197] Table 1.109 provides 660 compounds E109.1 to E109.660 of formula (Ia), where R 1b NHAc is A 1 CH is A 2a is N, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0198] Table 1.110 provides 660 compounds E110.1 to E110.660 of formula (Ia), where R 1b NHAc is A 1CH is A 2a CH is, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0199] Table 1.111 provides 660 compounds E111.1 to E111.660 of formula (Ia), where R 1b NHAc is A 1 CH is A 2a is CF, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0200] Table 1.112 provides 660 compounds E112.1 to E112.660 of formula (Ia), where R 1b NHAc is A 1 CH is A 2a is CCl, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0201] Table 1.113 provides 660 compounds E113.1 to E113.660 of formula (Ia), where R 1b NHAc is A 1 CH is A 2a is CBr, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0202] Table 1.114 provides 660 compounds E114.1 to E114.660 of formula (Ia), where R 1b NHAc is A 1 CH is A 2a It is CCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0203] Table 1.115 provides 660 compounds E115.1 to E115.660 of formula (Ia), where R 1b NHAc is A 1 CH is A 2a It is CCH2CH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0204] Table 1.116 provides 660 compounds E116.1 to E116.660 of formula (Ia), where R 1b NHAc is A 1 CH is A 2a It is CCN, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0205] Table 1.117 provides 660 compounds E117.1 to E117.660 of formula (Ia), where R 1b NHAc is A 1 CH is A 2a It is COCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0206] Table 1.118 provides 660 compounds E118.1 to E118.660 of formula (Ia), where R 1b NHAc is A 1 is N, and A 2a is N, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0207] Table 1.119 provides 660 compounds E119.1 to E119.660 of formula (Ia), where R 1bNHAc is A 1 is N, and A 2a CH is, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0208] Table 1.120 provides 660 compounds E120.1 to E120.660 of formula (Ia), where R 1b NHAc is A 1 is N, and A 2a is CF, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0209] Table 1.121 provides 660 compounds E121.1 to E121.660 of formula (Ia), where R 1b NHAc is A 1 is N, and A 2a is CCl, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0210] Table 1.122 provides 660 compounds E122.1 to E122.660 of formula (Ia), where R 1b NHAc is A 1 is N, and A 2a is CBr, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0211] Table 1.123 provides 660 compounds E123.1 to E123.660 of formula (Ia), where R 1b NHAc is A 1 is N, and A 2a It is CCH3, and R 2 , A 2b , R 4 , R 5This is defined in Table Z.

[0212] Table 1.124 provides 660 compounds E124.1 to E124.660 of formula (Ia), where R 1b NHAc is A 1 is N, and A 2a It is CCH2CH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0213] Table 1.125 provides 660 compounds E125.1 to E125.660 of formula (Ia), where R 1b NHAc is A 1 is N, and A 2a It is CCN, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0214] Table 1.126 provides 660 compounds E126.1 to E126.660 of formula (Ia), where R 1b NHAc is A 1 is N, and A 2a It is COCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0215] Table 1.127 provides 660 compounds E127.1 to E127.660 of formula (Ia), where R 1b is CN, A 1 CH is A 2a is N, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0216] Table 1.128 provides 660 compounds E128.1 to E128.660 of formula (Ia), where R1b is CN, A 1 CH is A 2a CH is, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0217] Table 1.129 provides 660 compounds E129.1 to E129.660 of formula (Ia), where R 1b is CN, A 1 CH is A 2a is CF, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0218] Table 1.130 provides 660 compounds E130.1 to E130.660 of formula (Ia), where R 1b is CN, A 1 CH is A 2a is CCl, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0219] Table 1.131 provides 660 compounds E131.1 to E131.660 of formula (Ia), where R 1b is CN, A 1 CH is A 2a is CBr, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0220] Table 1.132 provides 660 compounds E132.1 to E132.660 of formula (Ia), where R 1b is CN, A 1 CH is A 2a It is CCH3, and R 2 , A 2b , R 4 , R5 This is defined in Table Z.

[0221] Table 1.133 provides 660 compounds E133.1 to E133.660 of formula (Ia), where R 1b is CN, A 1 CH is A 2a It is CCH2CH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0222] Table 1.134 provides 660 compounds E134.1 to E134.660 of formula (Ia), where R 1b is CN, A 1 CH is A 2a It is CCN, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0223] Table 1.135 provides 660 compounds E135.1 to E135.660 of formula (Ia), where R 1b is CN, A 1 CH is A 2a It is COCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0224] Table 1.136 provides 660 compounds E136.1 to E136.660 of formula (Ia), where R 1b is CN, A 1 is N, and A 2a is N, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0225] Table 1.137 provides 660 compounds E137.1 to E137.660 of formula (Ia), where R 1b is CN, A 1 is N, and A 2a CH is, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0226] Table 1.138 provides 660 compounds E138.1 to E138.660 of formula (Ia), where R 1b is CN, A 1 is N, and A 2a is CF, R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0227] Table 1.139 provides 660 compounds E139.1 to E139.660 of formula (Ia), where R 1b is CN, A 1 is N, and A 2a is CCl, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0228] Table 1.140 provides 660 compounds E140.1 to E140.660 of formula (Ia), where R 1b is CN, A 1 is N, and A 2a is CBr, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0229] Table 1.141 provides 660 compounds E141.1 to E141.660 of formula (Ia), where R 1b is CN, A 1 is N, and A 2a It is CCH3, and R2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0230] Table 1.142 provides 660 compounds E142.1 to E142.660 of formula (Ia), where R 1b is CN, A 1 is N, and A 2a It is CCH2CH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0231] Table 1.143 provides 660 compounds E143.1 to E143.660 of formula (Ia), where R 1b is CN, A 1 is N, and A 2a It is CCN, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0232] Table 1.144 provides 660 compounds E144.1 to E144.660 of formula (Ia), where R 1b is CN, A 1 is N, and A 2a It is COCH3, and R 2 , A 2b , R 4 , R 5 This is defined in Table Z.

[0233] The compounds according to the present invention may have numerous advantages, including, in particular, advantageous levels of biological activity for protecting plants from fungal diseases, or excellent properties for use as agricultural chemical active ingredients (e.g., high biological activity, advantageous activity spectrum, increased safety profile, improved physicochemical properties, or improved biodegradability). The compounds according to the present invention have particularly advantageous levels of biological activity for protecting plants from oomycetes such as Phytophthora, Plasmopara, and Pythium.

[0234] Compounds of formula (I) (wherein Z is O) can be prepared as shown in schemes 1 to 14 below, wherein which case, unless otherwise specified, the definitions of each variable are as defined in this invention.

[0235] The compound of formula (I) is prepared 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 in the presence of a suitable palladium catalyst such as tetrakistriphenylphosphine palladium, palladium chloride, [1,1-bis(diphenylphosphine)ferrocene]dichloropalladium(II), or bis(diphenylphosphine)palladium(II) chloride, by combining the compound of formula (II) (wherein X is Cl, Br, or I) with the compound of formula (III) (wherein R 6 Hydrogen and C are independent of each other. 1-6 Alkyl or two R 6 together become C 3-8 It can be prepared by Suzuki cross-coupling with a compound of formula (III) (wherein R 6 Hydrogen and C are independent of each other. 1-6 Alkyl or two R 6 together become C 3-8 The cycloalkyl compounds (which can form cycloalkyl groups) are prepared by known methods or are commercially available. This conversion is shown in Scheme 1. [ka] Scheme 1

[0236] The compound of formula (II) (wherein X is Cl, Br, or I) reacts with the compound of formula (IV) (wherein X is Cl, Br, or I) and the compound of formula (V) (wherein X 1 However, it can be prepared by reacting it with a suitable leaving group such as Cl, Br, I, triflate, tosyl, or mesyl. This transformation is shown in Scheme 2. [ka] Scheme 2

[0237] The compound of formula (IV) (wherein X is Cl, Br or I) is formed by activating the carboxylic acid functional group of the compound of formula (VII) with the amine compound of formula (VI) (wherein X is Cl, Br or I), resulting in the compound of formula (VII) (wherein X 2 This is an amide coupling conversion with a carboxylic acid (where X is OH), by converting the -OH of the carboxylic acid to a good leaving group such as a chloride group, for example by using (COCl)2 or SOCl2, before treatment with the compound of formula (VI) (where X is Cl, Br, or I), preferably in a suitable solvent (e.g., N-methylpyrrolidone, acetonitrile, dimethylacetamide, dichloromethane, or tetrahydrofuran), preferably at a temperature of 25°C to 60°C, optionally in the presence of a base such as triethylamine or N,N-diisopropylethylamine, or optionally in the presence of a base (e.g., triethylamine or N,N-diisopropylethylamine), in a suitable solvent (e.g., acetonitrile), and obtained by a process that is normally carried out under the conditions described in the literature for amide coupling with 1-propanephosphonic acid cyclic anhydride (T3P), for example. See, for example, Chem.Soc.Rev.2009,38,606 and Chem.Soc.Rev.2011,40,5084. This conversion is shown in Scheme 3. [ka] Scheme 3

[0238] Alternatively, a compound of formula (II) (wherein X is Cl, Br, or I) in the presence of a base such as Cs2CO3, K2CO3, NaH, or NaOtBu, reacts with an amine compound of formula (VI) (wherein X is Cl, Br, or I) and a compound of formula (V) (wherein X 1 However, by reacting with a good leaving group such as Cl, Br, I, triflate, tosyl or mesyl, the compound obtained of formula (IX) (wherein X is Cl, Br or I) is then used to form the compound of formula (VII) (wherein X 2 It can be prepared in two steps by reacting (wherein X is OH) with the above conditions using peptide coupling conversion. Alternatively, the compound of formula (II) (wherein X is Cl, Br or I) can be reacted in a suitable solvent, for example, in the presence of NaBH(OAc)3 or NaBH3CN, and finally in the presence of a Brønsted acid or Lewis acid such as acetic acid, with the aldehyde of formula (VIII) (wherein R 9 However, C 1-5 Alkyl, C 1-5 Alkoxy-C 1-5 Alkyl, C 3-6 Cycloalkyl-C 1-3 Alkyl, C 2-5 Alkenil, C 2-5 Alkinyl, 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 1-6The compound can be obtained from the amine of formula (VI) (wherein X is Cl, Br, or I) by reductive amination with an alkyl group. Alternatively, another reagent system for reductive amination uses a combination of titanium isopropoxide and NaBH4. The synthesis of the compound of formula (II) (wherein X is Cl, Br, or I) from the amine of formula (VI) (wherein X is Cl, Br, or I) is shown in Scheme 4. [ka] Scheme 4

[0239] Alternatively, the compound of formula (II) (wherein X is Cl, Br, or I) can be prepared by reacting the compound 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. The compound of formula (X) can be prepared by reacting the compound of formula (XI) with the compound of formula (V) (wherein X) in the presence of a base such as Cs2CO3, K2CO3, NaH, or NaOtBu. 1 However, it can be obtained by alkylating with Cl, Br, I, triflate, tosyl or mesyl (which are good leaving groups). The compound of formula (XI) can be obtained by using the above conditions to alkylate the amine of formula (XII) to the compound of formula (VII) (wherein X 2 The compound of formula (X) can be obtained by reacting the amine of formula (XIII) with the compound of formula (VII) (wherein X is OH) via peptide coupling conversion. Alternatively, the compound of formula (X) can be obtained by using the above conditions to react the amine of formula (XIII) with the compound of formula (VII) (wherein X is OH). 2 The amine of formula (XIII) can be obtained by reacting the compound of formula (XII) with the compound of formula (V) (wherein X is OH) in the presence of a base such as Cs2CO3, K2CO3, NaH or NaOtBu, via peptide coupling conversion. 1However, it can be prepared by reacting it with a good leaving group such as Cl, Br, I, triflate, tosyl, or mesyl. Alternatively, the compound of formula (XIII) can be prepared in a suitable solvent, for example in the presence of NaBH(OAc)3 or NaBH3CN, and finally in the presence of a Brønsted acid or Lewis acid such as acetic acid, to an aldehyde of formula (VIII) (wherein R 9 However, C 1-5 Alkyl, C 1-5 Alkoxy-C 1-5 Alkyl, C 3-6 Cycloalkyl-C 1-3 Alkyl, C 2-5 Alkenil, C 2-5 Alkinyl, 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 It can be obtained from the amine of formula (XII) by reductive amination with an alkyl group. Alternatively, another reagent system for reductive amination uses a combination of titanium isopropoxide and NaBH4. These conversions are shown in Scheme 5. [ka] Scheme 5

[0240] Compounds of formula (VI) (wherein X is Cl, Br, or I) can be prepared by reducing nitro compounds of formula (XIV) (wherein X is Cl, Br, or I) with a reducing agent such as stannous chloride dihydrate or iron in the presence of ammonium chloride or acetic acid. Such transformations are described in the literature (see, for example, Tetrahedron Lett. 1984, 25, 839). Alternatively, compounds of formula (XIV) (wherein X is Cl, Br, or I) can be prepared 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, a compound of formula (VI) (wherein X is Cl, Br, or I) may be converted into an amine of formula (XVI) (wherein X is Cl, Br, or I) using an acid such as trifluoroacetic acid or hydrochloric acid, or by other methods generally known to those skilled in the art. 3 The amines can be prepared by deprotection of an amine protecting group (wherein X is an amine protecting group such as tert-butoxycarbonyl or benzyloxycarbonyl). The amine of formula (XVI) (wherein X is Cl, Br, or I) can be obtained from a Curtius rearrangement, which is obtained by treating the carboxylic acid of formula (XVII) (wherein X is Cl, Br, or I) with an azidating agent such as diphenyl phosphorazide or sodium azide in the presence of a base, preferably triethylamine and a solvent such as tert-butanol. Examples of such transformations are described in International Publication No. 2008 / 091195 (page 57). Alternatively, the reaction can be carried out using Boc2O and several catalysts such as tetrabutylammonium bromide and zinc triflate (described in Org. Lett. 2005, 7, 4107). These transformations are shown in Scheme 6. [ka] Scheme 6

[0241] The compound of formula (IV) (wherein X is Cl, Br or I) is commercially available, or the compound of formula (VI) (wherein X is Cl, Br or I, R 7 C 1-6 The alkyl compound can be prepared by saponifying it in a suitable solvent such as methanol, ethanol, or water at room temperature to reflux using a base such as NaOH or LiOH. The compound of formula (XVIII) (wherein X is Cl, Br, or I, and R 7 C 1-6 The alkyl compound (wherein R) is commercially available or in a suitable solvent such as dichloromethane, chloroform, tetrahydrofuran, or acetonitrile, is a compound of formula (XIX) (wherein R) 7 C 1-6 It can be prepared by reacting an alkyl group with a halogenating agent such as N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, or bromine. These conversions are shown in Scheme 7. [ka] Scheme 7

[0242] Compound of formula (VII) (wherein R 7 is C 1-6 Alkyl compounds are commercially available or can be prepared by the reaction of a compound of formula (XX) (wherein X is Cl, 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 shown in Scheme 8. [ka] Scheme 8

[0243] The compound of formula (XV) is commercially available, or alternatively, in a solvent such as water, ethanol, acetone, or acetonitrile, the compound of formula (XXI) and the compound of formula (XXIII) (wherein X is Cl, Br, or I, and R) 8C 1-6 Alkyl or two R 8 together become C 3-8 It can be prepared by reacting with a compound of formula (XXIV) (wherein X is Cl, Br, or I), and from a compound of formula (VII) to a compound of formula (XX) (wherein X is Cl, Br, or I), and from a compound of formula (XXV) (wherein R 7 C 1-6 Compounds of formula (XIX) (where R is alkyl) 7 C 1-6 It can be used to prepare compounds of formula (XXI), compounds of formula (XXIV) (wherein X is Cl, Br or I), and compounds of formula (XVI) (wherein R 7 C 1-6 Alkyl compounds are prepared by known methods or are commercially available. These conversions are shown in Scheme 9. [ka] Scheme 9

[0244] Alternatively, the compound of formula (I) can be converted into the compound of formula (XXVI) in the presence of a base such as Cs2CO3, K2CO3, NaH, or NaOtBu, and the compound of formula (XXVI) can be converted into the compound of formula (V) (wherein X 1 However, it can be prepared by alkylating with Cl, Br, I, triflate, tosyl or mesyl (which are good leaving groups). The compound of formula (XXVI) can be prepared by using the above conditions to alkylate the amine of formula (XXVII) with the compound of formula (VII) (wherein X 2 It can be obtained by reacting it with a compound of formula (V) (where X is OH) in the presence of a base such as Cs2CO3, K2CO3, NaH or NaOtBu, via peptide coupling conversion. Alternatively, the compound of formula (XXVII) can be obtained by reacting it with a compound of formula (V) (where X is OH) in the presence of a base such as Cs2CO3, K2CO3, NaH or NaOtBu. 1However, by alkylation with a good leaving group such as Cl, Br, I, triflate, tosyl or mesyl, the compound of formula (XXVIII) can be obtained. Using the above conditions, the amine of formula (XXVIII) and the compound of formula (VII) (wherein X) can be used in a peptide coupling conversion. 2 The reaction with (where is OH) can yield the compound of formula (I). These transformations are shown in scheme 10. [ka] Scheme 10

[0245] Compound (XXVII) of formula (XXIX) (wherein X) is obtained by using an acid such as trifluoroacetic acid or hydrochloric acid, or by other methods generally known to those skilled in the art. 3 It can be prepared by deprotection of an amine protecting group (wherein X is hydrogen or an amine protecting group such as tert-butoxycarbonyl or benzyloxycarbonyl). 3 The compound of formula (XVI) (wherein X is hydrogen, or an amine protecting group such as tert-butoxycarbonyl or benzyloxycarbonyl) is prepared 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 in the presence of a suitable palladium catalyst such as tetrakistriphenylphosphine palladium, palladium chloride, [1,1-bis(diphenylphosphine)ferrocene]dichloropalladium(II), or bis(diphenylphosphine)palladium(II) chloride, where X is Cl, Br, or I, and X 3 A is either hydrogen or an amine protecting group such as tert-butoxycarbonyl or benzyloxycarbonyl) and a compound of formula (III) (wherein A 1 is CH or N, and R 6 Hydrogen and C are independent of each other. 1-6 Alkyl or two R 6 together become C 3-8These can be prepared by Suzuki cross-coupling of a cycloalkyl group (which can form a cycloalkyl group). These transformations are shown in Scheme 11. [ka] Scheme 11

[0246] Alternatively, the compound of formula (I) can be used to make the compound of formula (XXX) into the compound of formula (XXXI) (wherein X 2 The compound of formula (XXX) can be prepared by reacting it with a compound of formula (II) and a compound of formula (XXXII) (where R is OH) by peptide coupling conversion. The compound of formula (XXX) is prepared 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 in the presence of a suitable palladium catalyst such as tetrakistriphenylphosphine palladium, palladium chloride, [1,1-bis(diphenylphosphine)ferrocene]dichloropalladium(II) or bis(diphenylphosphine)palladium(II) chloride, by reacting it with a compound of formula (II) and a compound of formula (XXXII) (where R is OH). 6 Hydrogen and C are independent of each other. 1-6 Alkyl or two R 6 together become C 3-8 It can be prepared by Suzuki cross-coupling with a compound of formula (XXXII) (wherein R 6 Hydrogen and C are independent of each other. 1-6 Alkyl or two R 6 together become C 3-8 These compounds (which can form cycloalkyl groups) are prepared by known methods or are commercially available. These conversions are shown in Scheme 12. [ka] Scheme 12

[0247] The compound of formula (Ib) (wherein Z is S) can be prepared by the reaction of the compound of formula (Ia) (wherein Z is S) with phosphorus pentasulfide or Lawson's reagent (CAS: 19172-47-5) in a suitable solvent such as toluene, xylene, or dichloromethane. This conversion is shown in Scheme 13. [ka] Scheme 13

[0248] Alternatively, the compound of formula (Ib) (where Z is S) can be used to make the compound of formula (XXXb) the compound of formula (XXXI) (where X 2 The compound of formula (XXIV) can be prepared by reacting it with a peptide coupling transform (where OH is present). The compound of formula (XXX) can be prepared by reacting the compound of formula (XXX) with phosphorus pentasulfide or Lawson's reagent (CAS: 19172-47-5) in a suitable solvent such as toluene, xylene, or dichloromethane. This transformation is shown in Scheme 14. [ka] Scheme 14

[0249] When the term "compound according to the present invention" is used, it refers to the compound according to the present invention.

[0250] Alternatively, the compounds according to the present invention can be obtained by transformations using standard synthetic techniques known to those skilled in the art. Non-exclusive 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.

[0251] The compounds according to the present invention can be converted to other compounds according to the present invention in a manner known by means of substituting one or more substituents of the starting compound according to the present invention with other substituents according to the present invention in a conventional manner.

[0252] Depending on the selection of suitable reaction conditions and starting materials in each case, it may be possible, for example, to substitute only one substituent with another substituent according to the present invention in a single reaction step, or to substitute multiple substituents with other substituents according to the present invention in the same reaction step.

[0253] Salts of the compounds according to the present invention can be prepared by known methods. For example, acid addition salts of the compounds according to the present invention can be obtained by treatment with a suitable acid or a suitable ion exchange reagent, and salts with a base can be obtained by treatment with a suitable base or a suitable ion exchange reagent.

[0254] Salts of the compounds according to the present invention can be converted to free compounds by conventional methods, acid addition salts can be converted, for example, by treatment with a suitable basic compound or a suitable ion exchange reagent, and salts with a base can be converted, for example, by treatment with a suitable acid or a suitable ion exchange reagent.

[0255] Salts of the compounds according to the present invention can be converted to other salts of the compounds according to the present invention, acid addition salts, for example, other acid addition salts, by methods known to the present invention, for example, by treatment of an inorganic acid salt, such as a silver acetate hydrochloride, with a suitable metal salt of the acid, such as a sodium, barium, or silver salt of the acid, in a suitable solvent (for example, an inorganic salt that forms silver chloride insoluble therein and therefore precipitates from the reaction mixture).

[0256] Depending on the procedure or reaction conditions, the compounds according to the present invention, which have salt-forming properties, can be obtained in free form or in salt form.

[0257] In each case, the compounds according to the present invention, in free form or salt form, and, where appropriate, their tautomers, may exist in one form of possible isomers or as mixtures thereof, depending on the number, absolute and relative configuration of chiral carbon atoms present in the molecule and / or the stereoconfiguration of non-aromatic double bonds present in the molecule, in the form of pure isomers, such as anticarpone and / or diastereomers, or as stereoisomer mixtures, such as enantiomer mixtures, such as racemic compounds, diastereomer mixtures or racemic compound mixtures; the present invention relates to pure stereoisomers and to all possible isomer mixtures, and in all cases in this sense, even when stereochemical details are not specifically described in any case, it should be understood in this sense in the above and below herein.

[0258] The diastereomer or racemic mixture of compounds according to the present invention, in the free or salt form obtained depending on the selected starting materials and procedure, can be separated into pure diastereomers or racemic compounds based on the physicochemical differences of the components by known methods, such as fractional crystallization, distillation and / or chromatography.

[0259] Enantiomer mixtures such as racemates obtained by similar methods can be decomposed into optical enantiomers by known methods, for example, by recrystallization from an optically active solvent, by chromatography in a chiral adsorbent, for example by high-performance liquid chromatography (HPLC) in acetylcellulose using a suitable microorganism, by cleavage by a specific immobilized enzyme via the formation of an inclusion compound, or by conversion to a diastereomer salt, for example by using a chiral crown ether in which only one enantiomer is combined, for example, by reacting the basic final product racemate with an optically active acid such as a carboxylic acid, for example camphoric acid, tartaric acid, or malic acid, or a sulfonic acid, for example camphor sulfonic acid, and separating the diastereomer mixture thus obtained, for example by fractional crystallization based on different solubility, to obtain a diastereomer from which the desired enantiomer can be released by the action of a suitable substance, for example a basic substance.

[0260] Pure diastereomers or enantiomers can be obtained according to the present invention not only by separating a suitable mixture of stereoisomers, but also by generally known diastereoselective or enantioselective synthesis methods, such as the method according to the present invention using suitable stereochemical starting materials.

[0261] N-oxides can be prepared by reacting the compounds according to the present invention with a suitable oxidizing agent, such as an H2O2 / urea adduct, in the presence of an acid anhydride, such as trifluoroacetic anhydride. Such oxidation is known from the literature, e.g., J.Med.Chem., 32(12), 2561-73, 1989 or International Publication No. 00 / 15615.

[0262] When individual components have different biological activities, it is advantageous to isolate or synthesize the more biologically effective stereoisomers, such as enantiomers or diastereomers, or stereoisomer mixtures, such as enantiomer mixtures or diastereomer mixtures, in each case.

[0263] The compounds according to the present invention and optionally their tautomers may be obtained in free form or salt form, optionally in hydrate form, and / or in other solvents, such as solvents that have been used to crystallize compounds existing in solid form.

[0264] The following examples illustrate, but are not limiting, the present invention.

[0265] The present invention also provides intermediates useful for the preparation of compounds according to the present invention.

[0266] The following intermediates form further embodiments of the present invention.

[0267] Compound of formula (II) [ka] (In the formula, Z is O or S, preferably Z is O; R 1a , R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, 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 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, C 2-4 Alkenyl and -NHC(O)C 1-6 Selected independently of alkyl; preferably, R 1a and R 1c is hydrogen, R 1b is hydrogen, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl and C 2-4 Can be selected from Alkenil; A 2 CR 2 Alternatively, selected independently of N, provided that there are no more than four A's. 2 is N, preferably 3 or fewer A 2 is N, preferably two or fewer A 2 is N, preferably one or less A 2 N is more preferably five A 2 CR 2 and; R 2 These are hydrogen, hydroxyl, halogen, CN, and 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 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, 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 Selected independently from cycloalkylaminos, where 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 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, 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 cycloalkylamino groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs, more preferably R 2 These are hydrogen, hydroxyl, halogen, CN, and 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, C1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl and diC 1-6 Independently selected from alkylaminocarbonyl, where 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 sulfanyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, and C 1-6 Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; R 4 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 Alkenil, C 2-6 Alkinyl, 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 Selected from alkyl and CN, where C 1-6Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl and diC 1-6 Alkylaminocarbonyl-C 1-6 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN, preferably R 4 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 Selected from alkoxy, where 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 alkoxy group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN; and X is Cl, Br, or I; or its salt or N-oxide.

[0268] Compound of formula (X) [ka] (In the formula, Z is O or S, preferably Z is O; R 1a , R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, 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 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, C 2-4 Alkenyl and -NHC(O)C 1-6 Selected independently of alkyl; preferably, R 1a and R 1c is hydrogen, R 1b is hydrogen, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 2-4 Can be selected from Alkenil; A 2 CR 2 Alternatively, selected independently of N, provided that there are no more than four A's. 2 is N, preferably 3 or fewer A 2 is N, preferably two or fewer A 2 is N, preferably one or less A 2 N is more preferably five A 2 CR 2 and; R 2 These are hydrogen, hydroxyl, halogen, CN, and 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 Alkenil, C 2-6 Alkinyl, C3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, 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 Selected independently from cycloalkylaminos, where 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 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, 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 cycloalkylamino groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs, more preferably R 2 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C1-6 Alkoxy, C 3-6 Cycloalkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl and diC 1-6 Independently selected from alkylaminocarbonyl, where 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 sulfanyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl and diC 1-6 Each alkylaminocarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxyl, and CN; and R 4 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 Alkenil, C 2-6 Alkinyl, 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 1-6Selected from alkyl and CN, where 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 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl and diC 1-6 Alkylaminocarbonyl-C 1-6 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN, preferably R 4 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 Selected from alkoxy, where 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 alkoxy group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN. or its salt or N-oxide.

[0269] Compound of formula (XVII) [ka] (In the formula, A 1 is CH or N, preferably N; R 1a , R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, 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 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, C 2-4 Alkenyl and -NHC(O)C 1-6 Selected independently of alkyl; preferably, R 1a and R 1c is hydrogen, R 1b is hydrogen, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl and C 2-4 Can be selected from Alkenil; and R 5 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 Alkoxyaminos, and C 1-6 Alkyl C 1-6 Selected from alkoxyaminos, where C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, diC 1-6 Alkylamino, C 1-6 Alkoxyaminos and C 1-6 Alkyl C 1-6 Each alkoxyamino group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN, preferably R 5 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 Selected from alkyl groups, where each of the groups may be optionally substituted with 1 to 3 substituents independently selected from halogens and CNs. or its salt or N-oxide.

[0270] Compound of formula (XVIII) [ka] (In the formula, A 1 is CH or N, preferably N; R 1a , R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, 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 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, C 2-4 Alkenyl and -NHC(O)C 1-6 Selected independently of alkyl; preferably, R 1a and R 1cis hydrogen, R 1b is hydrogen, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl and C 2-4 Can be selected from Alkenil; R 4 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 Alkenil, C 2-6 Alkinyl, 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 Selected from alkyl and CN, where 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 Alkenil, C 2-6 Alkinyl, 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 1-6Alkylaminocarbonyl-C 1-6 Alkyl and diC 1-6 Alkylaminocarbonyl-C 1-6 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN, preferably R 4 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 Selected from alkoxy, where 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 alkoxy group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN; and R 5 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 Alkoxyaminos, and C 1-6 Alkyl C 1-6 Selected from alkoxyaminos, where 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 Alkoxyaminos and C1-6 Alkyl C 1-6 Each alkoxyamino group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN, preferably R 5 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 Selected from alkyl groups, where each of the groups may be optionally substituted with 1 to 3 substituents independently selected from halogens and CNs. or its salt or N-oxide.

[0271] The compounds of formula (I) as defined in this invention may be used, for example, as active ingredients for controlling plant pathogens, or as non-living substances for controlling potentially harmful microorganisms or organisms to humans in the agricultural sector and related fields of use. Novel compounds are distinguished by their excellent activity at low doses, the sufficient tolerance exhibited by plants, and their environmental safety. They possess highly useful therapeutic, preventive, and systemic properties and can be used to protect many cultivated plants. The compounds of formula (I) as defined in this invention can also be used to suppress or eradicate pathogens appearing on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of different crops of useful plants, while simultaneously protecting those parts of the plant that will grow later from plant pathogenic microorganisms.

[0272] Compounds of formula (I) as defined in this invention may also be used as mycicides. The term “mycicide” as used herein means a compound that controls, modifies, or prevents the growth of fungi. The term “mycicidal amount” means the amount of such compound or combination of such compounds that can produce an effect against the growth of fungi. Controlling or modifying effects include all deviations from natural occurrence, such as fungicidal or delayed growth, while prevention includes the formation of barriers or other defenses in plants to prevent fungal infections.

[0273] For protection against fungal infections and plant pathogenic fungi occurring in the soil, a mixture of formula (I) as defined in the present invention may also be used as a coating agent for treating plant propagation materials, such as seeds, tubers or grains, or plant cuttings (e.g., rice), such as fruits. The propagation material may be treated with a composition containing a compound of formula (I) as defined in the present invention before planting: for example, seeds may be coated before sowing. The compound of formula (I) as defined in the present invention may also be applied to grains (coated) either by impregnating the seeds in a liquid formulation or by coating the seeds with a solid formulation. The composition may also be applied to the planting site when the propagation material is planted, for example, in the sowing furrow during sowing. The present invention also relates to such methods for treating plant propagation materials and to plant propagation materials treated in this manner.

[0274] Furthermore, compounds of formula (I) as defined in the present invention can be used in related fields, for example, to control fungi in the protection of industrial materials, including wood and wood-related industrial products, in food storage, and in hygiene management.

[0275] In addition, the present invention may also be used to protect non-biological materials, such as sawn timber, wall coverings, and paints, from fungal attacks.

[0276] Compounds of formula (I) as defined in the present invention, and fungicidal compositions containing them, can be used to control plant diseases caused by broad-spectrum fungal plant pathogens. They are effective in controlling broad-spectrum plant diseases such as those caused by leaf pathogens of ornamental plants, lawns, vegetables, fields, grains, and fruit crops.

[0277] Examples of disease-causing fungi and fungal vectors, as well as plant pathogenic bacteria and viruses, that can be controlled include: Absidia corymbifera, species of the genus Alternaria, species of the genus Aphanomyces, species of the genus Ascochyta, species of the genus Aspergillus including A. flavus, A. fumigatus, A. nidulans, A. niger, and A. terrus, species of the genus Aureobasidium including A. pullulans, Blastomyces dermatitidis, Blumeria graminis, and Bremia lactucaea. Species of the genus Botryosphaeria, including B. lactucae, B. dothidea, and B. obtusa; species of the genus Botrytis, including B. cinerea; species of Candida, including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, and C. tropicalis; species of Cephaloascus fragrans and Ceratocystis. Species of the genus Cercospora (spp.), including C. arachidicola, Cercosporidium personatum, species of the genus Cladosporium (spp.), Claviceps purpurea, Coccidioides immitis, species of the genus Cochliobolus (spp.), and species of the genus Colletotrichum (spp.), including C. musae. Cryptococcus neoformans, species of the genus Diaporthe, species of Didymella, species of Drechslera, species of Elsinoe, Species of the genus Epidermophyton (spp.), Erwinia amylovora, and Erysiphe species (spp.), including E. cichoracearum. Fusarium spp., including species of the genus Fusarium such as Eutypa lata, F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, and F. solani, as well as Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, and Gloeosporium musarum. musarum), Glomerella cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, species of Helminthosporium, species of Hemileia, species of Histoplasma including H. capsulatum, Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium sediciosum This includes *Mycosphaerella* species, including *Mycosphaerella spp.*,), Oncobasidium theobromaeon, Ophiostoma piceae, species of the genus Paracoccidioides spp., species of the genus Penicillium including P. digitatum and P. italicum, species of the genus Petriellidium spp., species of the genus Peronosclerospora including P. maydis, P. philippinensis and P. sorghi, species of the genus Peronospora spp., wheat blight fungus (Phaeosphaeria) Species of the genus *Phakopsora nodorum*, Phakopsora pachyrhizi, Phellinus igniarus, species of *Phialophora*, species of *Phoma*, species of *Phytophthora* including *Phomopsis viticola* and *P. infestans*, species of *Plasmopara* including *P. halstedii* and *P. viticola*, species of *Pleospora*, and species of *Podosphaera* including apple powdery mildew fungus (*P. leucotricha*). spp.), Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, species of the genus Pseudomonas (Pseudomonas spp.), species of the genus Pseudoperonospora including P. cubensis and P. humuli (Pseudoperonospora spp.), Pseudopeziza tracheiphila, P.Species of the genus Puccinia (P.hordei, P.recondita, P.striiformis, P.triticina), species of the genera Pyrenopeziza, Pyrenophora, species of Pyricularia (P.oryzae), species of Pythium (P.ultimum), species of Ramularia, species of Rhizoctonia, Rhizomucor pusillus, and Rhizopus arizus. This includes species of the genus Rhynchosporium (including *arrhizus*), species of the genus Sedosporium (including *S. apiospermum* and *S. prolificans*), and *Schizothyrium pomi*. Species of the genera Sclerotinia, Sclerotium, Septoria (including S. nodorum and S. tritici), Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix, Stagonospora nodorum, Stemphylium, Stereum hirsutum, and Thanatephorus cucumeris. This includes species of the genus *Tilletia* (including *Tilletia cucumeris*), *Tilletia basicola*, *Tilletia spp.*, *Tilletia harzianum*, *Tilletia pseudokoningii*, and *Tilletia viride*, as well as species of the genus *Trichoderma* (including *Tilletia viride*). Species of the genera Trichophyton, Typhula, Uncinula necator, Urocystis, Ustilago, Venturia (including V. inaequalis), Verticillium, and Xanthomonas.

[0278] In particular, compounds of formula (I) as defined in the present invention, and fungicidal compositions containing them, can be used to control plant diseases caused by broad-spectrum fungal plant pathogens in basidiomycetes, ascomycetes, oomycetes and / or deuteromycetes, blasocladiomycetes, chytridiomycetes, glomeromycetes and / or mucoromycetes. More particularly, compounds of formula (I) as defined in the present invention can be used to control oomycetes.

[0279] These pathogens may include the following: Phytophthora diseases, such as those caused by Phytophthora capsici, Phytophthora infestans, Phytophthora sojae, Phytophthora fragariae, Phytophthora nicotianae, Phytophthora cinnamomi, Phytophthora citricola, Phytophthora citrophthora, and Phytophthora erythroseptica; and Pythium aphanidermatum and Pythium arenomanes. Pythium diseases, such as those caused by *Pythium arrhenomanes*, *Pythium graminicola*, *Pythium irregulare*, *Pythium sylvaticum*, and *Pythium ultimum*; *Peronospora destructor*, *Peronospora parasitica*, *Plasmopara viticola*, *Plasmopara halstedii*, *Pseudoperonospora cubensis*, *Albugo candida*, and *Sclerophthora macrospora*. Diseases caused by Peronosporales, such as macrospora and Bremia lactucae;Oomycetes, including Aphanomyces cochlioides, Labyrinthula zosterae, Peronosclerospora sorghi, and Sclerospora graminicola, are also included. Ascomycetes, for example, Stemphylium solani, Stagonospora tainanensis, Spirocaea oleaginea, Setosphaeria turcica, Pyrenochaeta lycoperisici, Pleospora herbarum, Phoma destructiva, Phaeosphaeria herpotrichoides, Phaeocryptocus gaeumannii, and Ophiosphaerella graminicola. graminicola), Ophiobolus graminis, Leptosphaeria maculans, Hendersonia creberrima, Helminthosporium triticirepentis, Setosphaeria turcica, Drechslera glycines, Didymella bryoniae, Cycloconium oleagineum, Corynespora cassiicola, Cochliobolus sativus, Bipolaris cactivora cactivora), apple scab fungus (Venturia inaequalis), Pyrenophora teres, wheat yellow spot fungus (Pyrenophora tritici-repentis), Alternaria alternata, Alternaria bracisicola (AlternariaPleosporales species such as brassicicola, Alternaria solani, and Alternaria tomatophila, Septoria tritici, Septoria nodorum, Septoria glycines, Cercospora arachidicola, Cercospora sojina, Cercospora zeae-maydis, Cercosporella capsellae, and Cercosporella herpotrichoides. Capnodiales (including herpotrichoides), Cladosporium carpophilum, Cladosporium effusum, Passalora fulva, Cladosporium oxysporum, Dothistroma septosporum, Isariopsis clavispora, Mycosphaerella fijiensis, Mycosphaerella graminicola, Mycovellosiella koepkeii, Phaeoisariopsis bataticola bataticola), Pseudocercospora vitis, Pseudocercosporella herpotrichoides, Ramularia beticola, Ramularia colo-signiMagnaporthales species such as collo-cygni, Gaeumannomyces graminis, Magnaporthe grisea, and Pyricularia oryzae (rice blast fungus), Anisogramma anomala, Apiognomonia errabunda, Cytospora platani, Diaporthe phaseolorum, Discula destructiva, Gnomonia fructicola, Greeneria uvicola, and Melanconium jugrandinum. Diaporthales species such as *juglandinum*, *Phomopsis viticola*, *Sirococcus clavigignenti-juglandacearum*, *Tubakia dryina*, *Dicarpella spp.*, and *Valsa ceratosperma*, as well as *Actinothyrium graminis*, *Ascochyta pisi*, *Aspergillus flavus*, *Aspergillus fumigatus*, and *Aspergillus nizrans*. * nidulans*, * Asperisporium caricae*, * Blumerierella jaapii*, species of the genus * Candida*, * Capnodium ramosum*, species of the genus * Cephaloascus*, * Cephalosporium gramineum*Gramineum, Ceratocystis paradoxa, Chaetomium spp., Hymenoscyphus pseudoalbidus, Coccidioides spp., Cylindrosporium padi, Diplocarpon malae, Drepanopeziza campestris, Elsinoe ampelina, Epicoccum nigrum, Epidermophyton spp., Eutypa lata, Geotrichum candizum Flea, spot, blast, or canker and / or rot caused by other species such as Gloeotinia candidum, Gibellina cerealis, Gloeocercospora sorghi, Gloeodes pomigena, Gloeosporium perennans, and others; Gloeotinia temulenta, Griphospaeria corticola, Kabatiella lini, Leptographium microsporum, Leptosphaerulinia crassiasca, Lophodermium sediciosum seditiosum), Marssonina graminicola, wheat mold (Microdochium nivale), Monilinia fructicola, Monographella albecensalbescens), Monosporascus cannonballus, species of the genus Naemacyclus, Ophiostoma novo-ulmi, Paracoccidioides brasiliensis, Penicillium expansum, Pestalotia rhododendri, species of the genus Petrielidium, species of the genus Pezicula, Phialophora gregata, Phyllachora pomigena, Phymatotrichum omnivora omnivora), Physalospora abdita, Plectosporium tabacinum, Polyscytalum pustulans, Pseudopeziza medicaginis, Pyrenopeziza brassicae, Ramulispora sorghi, Rhabdocline pseudotsugae, Rhynchosporium secalis, Sacrocladium oryzae (rice leaf rot fungus), species of the genus Scedosporium, Schizothyrium pomi, Sclerotinia sclerotiorum, Sclerotinia minor; species of the genus Sclerotium, Typhula ishikariensis, Seimatosporium marie *Leptophyllum mariae*, *Leptophyllum cupressi*, *Septocyta ruborum*, *Sphacelom perseae*, *Sporonema phacidioides*, *Stigmina palmivora*, *Tapesia yallundae*, *Taphrina bullata*, *Thielviopsis basicola*, *Trichoseptoria fructigena*, *Zygophiala jamaicensis*;For example, Blumeria graminis, Erysiphe polygoni, Uncinula necator, Sphaerotheca fuligena, apple powdery mildew fungus (Podosphaera leucotricha), Podospaera macularis, Golovinomyces cichoracearum, Leveillula taurica, Microsphaera diffusa, Oidiopsis gossypii, Phyllactinia guttata, and Oidium arachidis. Powdery mildew diseases caused by the Erysiphales order, such as Dothiorella aromatica, Diplodia seriata, Guignardia bidwellii, Botrytis cinerea, Botryotinia allii, Botryotinia fabae, Fusicoccum amygdali, Lasiodiplodia theobromae, Macrophoma theicola, Macrophomina phaseolina, and Phyllosticta cucurbitacearum. Molds such as those caused by Botryosphaeriales (e.g., Cucurbitacearum);Anthracnose caused by species of the genus Glommerelales, such as Colletotrichum gloeosporioides, Colletotrichum lagenarium, Colletotrichum gossypii, Glomerella cingulata, and Colletotrichum graminicola; and anthracnose caused by species of the genus Glommerelales, such as Acremonium strictum, Claviceps purpurea, Fusarium culmorum, Fusarium graminearum, and Fusarium bilgriforme. Fusarium virguliforme, Fusarium oxysporum, Fusarium subglutinans, Panama banana disease fungus (Fusarium oxysporum f.sp.cubense), Gerlachia nivale, Gibberella fujikuroi, Gibberella zeae, species of the genus Gliocladium, Myrothecium verrucaria, Nectria ramulariae, Trichoderma viride, Trichothecium roseum, and Verticillium theobromae Wilt or canker disease caused by Hypocreales (such as theobromae); Basidiomycete, which includes the following: smut fungi such as those caused by the order Ustilaginales, such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, and Ustilago zeae; and Puccinia arachidis, Puccinia cacabata, and Puccinia graminis. Puccinia graminis), Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia striiformis f.sp. Hordei, Puccinia striiformis f.sp. cecalisPucciniales, including species such as Secalis, Pucciniastrum coryli, Cronartium ribicola, Gymnosporangium juniperi-viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor, and Uromyces viciae-fabee. Caused by the order Uredinales, such as viciae-fabae; as well as species of the genus Cryptococcus, Exobasidium vexans, Marasmiellus inoderma, and Mycena.), Sphacelotheca reiliana, Typhula ishikariensis, Urocystis agropyri, Itersonilia perplexans, Corticium invisum, Laetisaria fuciformis, Waitea circinata, Rhizoctonia solani (rice sheath blight fungus), Thanetephorus cucurmeris (sugar beet root rot fungus), Entyloma dahliae, Entylomella microspora, Neovossia molliniae Basidiomycetes are fungi that cause other rot and disease, such as those caused by *Tilletia moliniae* and *Tilletia caries*. Blastocladiomycetes, such as Physoderma maydis. Mucoromycete species, such as Choanephora cucurbitarum, Mucor spp., and Rhizopus arrhizus. Furthermore, diseases caused by other species and genera closely related to those listed above.

[0280] In addition to their fungicidal activity, the compounds and compositions comprising the compound of formula (I) as defined in this invention may also be active against bacteria such as Erwinia amylovora, Erwinia caratovora, Xanthomonas campestris, Pseudomonas syringae, Streptomyces scabies and other related species, as well as certain protozoa.

[0281] Within the scope of the present invention, target crops and / or useful plants to be protected are typically berry plants, e.g., blackberries, blueberries, cranberries, raspberries and strawberries; cereals, e.g., barley, corn, millet, oats, rice, rye, sorghum, rye and wheat; fiber plants, e.g., cotton, flax, hemp, jute and sisal; crops, e.g., sugar and fodder beets, coffee, hops, mustard, rapeseed (canola), poppies, sugarcane, sunflowers, tea and tobacco; fruit trees, e.g., apples, apricots, avocados, bananas, cherries, citrus fruits, nectarines, peaches, pears and plums; grasses, e.g., Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St. Augustine grass and zoysia grass; herbs, e.g., basil, borage, chives, coriander, lavender, lavage, mint, oregano, parsley and rosemary , sage and thyme; legumes, e.g., kidney beans, lentils, peas and soybeans; nuts, e.g., almonds, cashews, peanuts, hazelnuts, peanuts, pecans, pistachios and walnuts; palms, e.g., oil palm; ornamental plants, e.g., flowers, shrubs and trees; other trees, e.g., cocoa, coconut, olive and rubber; vegetables, e.g., asparagus, eggplant, broccoli, cabbage, carrots, cucumbers, garlic, lettuce, mallow, melon, okra, onions, pepper, potatoes, pumpkins, rhubarb, spinach and tomatoes; and climbing plants, e.g., grapes, including perennial and annual crops.

[0282] Useful plants and / or target crops according to the present invention include conventional varieties such as insect-resistant (e.g., Bt. and VIP varieties), disease-resistant, herbicide-resistant (e.g., glyphosate- and glufosinate-resistant maize varieties, commercially available under trade names RoundupReady® and LibertyLink®), and nematode-resistant varieties, as well as genetically enhanced or genetically modified varieties. Examples of suitably genetically enhanced or genetically modified varieties include the Stoneville 5599BR cotton and Stoneville 4892BR cotton varieties.

[0283] The terms “useful plants” and / or “target crops” should be understood to also include useful plants that have been given resistance to herbicides such as bromoxynil or certain classifications of herbicides (e.g., HPPD inhibitors, ALS inhibitors such as primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovir-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors, or PPO (protoporphyrinogen-oxidase) inhibitors) by conventional crossbreeding or genetic engineering methods. An example of a crop that has been given resistance to imidazolinones, such as imazamox, by conventional breeding (mutation) methods is Clearfield® summer rapeseed (canola). Examples of crops that have been genetically modified to be resistant to herbicides or a certain class of herbicides include glyphosate- and glufosinate-resistant maize varieties that are commercially available under the trade names RoundupReady®, Herculex I®, and LibertyLink®.

[0284] The terms “useful plants” and / or “target crops” should be understood to include those that naturally exhibit or are conferred resistance to harmful insects. This includes plants transformed by the use of recombinant DNA technology, for example, that can synthesize one or more selectively acting toxins, such as those known from toxin-producing bacteria. Examples of toxins that can be expressed include δ-endotoxin, vegetative insecticidal protein (Vip), insecticidal protein from nematode-symbiotic bacteria, and toxins produced by scorpions, arachnids, wasps, and fungi. An example of a crop modified to express Bacillus thuringiensis toxin is Bt maize KnockOut (Syngenta Seeds). An example of a crop containing two or more genes encoding insecticide resistance and thus expressing two or more toxins is VipCot® (Syngenta Seeds). Crops or their seed materials can also exhibit resistance to multiple types of pests (so-called superimposed transgenic events when produced by genetic modification). For example, a plant can have the ability to express insecticidal proteins and simultaneously be resistant to herbicides, such as Herculex I® (registered trademark) (Dow AgroSciences, Pioneer Hi-Bred International).

[0285] The terms “useful plants” and / or “target crops” should be understood to also include useful plants transformed using recombinant DNA technology so that they can synthesize selectively acting antipathogenic substances, such as so-called “pathogenicity-associated proteins” (PRPs, see, e.g., European Patent Application Publication No. 0 392 225). Examples of such antipathogenic substances and transgenic plants capable of synthesizing such antipathogenic substances are known, for example, from European Patent Application Publication No. 0 392 225, International Publication No. 95 / 33818 and European Patent Application Publication No. 0 353 191. Methods for producing such plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above.

[0286] Toxins that can be expressed by transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis such as δ-endotoxins like Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip) such as Vip1, Vip2, Vip3 or Vip3A; or species of the genus Photorhabdus (Photorhabdus spp.) or Xenorhabdus (Xenorhabdus nematophilus), such as Photorhabdus luminescens or Xenorhabdus nematophilus. Insecticidal proteins of nematode-symbiotic bacteria such as spp.; toxins produced by animals such as scorpion toxin, spider toxin, large wasp (wasp) toxin and other insect-specific neurotoxins; toxins produced by fungi such as Streptomycete toxin, plant lectins such as pea lectin, barley lectin or snowdrop lectin; aglutinin; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patain, cystatin, and papain inhibitors; lysine, Examples include ribosome-inactivating proteins (RIPs) such as corn-RIP, abrin, rufin, saporin, or briodin; steroid metabolic enzymes such as 3-hydroxysteroid xidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, and HMG-COA-reductase; ion channel blockers such as sodium or calcium blockers; juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase, and glucanase.

[0287] Furthermore, it should be understood that in connection with the present invention, there exist δ-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or plant insecticidal proteins (Vip), such as Vip1, Vip2, Vip3, or Vip3A, as well as explicitly hybrid toxins, cleavage toxins, and modified toxins. Hybrid toxins are produced by recombinant synthesis through novel combinations of different domains of these proteins (see, for example, International Publication No. 02 / 15701). Cleavage toxins, such as cleavage Cry1Ab, are known. In the case of modified toxins, one or more amino acids of a naturally occurring toxin are replaced. In such amino acid substitutions, preferably, a protease recognition sequence that does not naturally exist is inserted into the toxin, for example, in the case of Cry3A055, and a cathepsin-G recognition sequence is inserted into the Cry3A toxin (see International Publication No. 03 / 018810).

[0288] Additional examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in European Patent Application Publication No. 0374753, International Publication No. 93 / 07278, International Publication No. 95 / 34656, European Patent Application Publication No. 0427529, European Patent Application Publication No. 451878, and International Publication No. 03 / 052073.

[0289] The preparation processes for such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparations are known, for example, from International Publication No. 95 / 34656, European Patent Application Publication No. 0367474, European Patent Application Publication No. 0401979, and International Publication No. 90 / 13651.

[0290] The toxins contained in transgenic plants confer resistance to harmful insects. Such insects can exist in any of the insect taxa, but are typically found in beetles (Coleoptera), diptera (Diptera), and butterflies (Lepidoptera).

[0291] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known, and some of them are commercially available. Examples of such plants include: YieldGard® (maize variety expressing Cry1Ab toxin); YieldGard Rootworm® (maize variety expressing Cry3Bb1 toxin); YieldGard Plus® (maize variety expressing Cry1Ab and Cry3Bb1 toxins); Starlink® (maize variety expressing Cry9C toxin); Herculex I® (maize variety expressing Cry1Fa2 toxin and the enzyme phosphinothrysin N-acetyltransferase (PAT) to achieve resistance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety expressing Cry1Ac toxin); Bollgard I® (cotton variety expressing Cry1Ac toxin); Bollgard These include II (registered trademark) (cotton varieties expressing Cry1Ac and Cry2Ab toxins); VipCot (registered trademark) (cotton varieties expressing Vip3A and Cry1Ab toxins); NewLeaf (registered trademark) (potato varieties expressing Cry3A toxin); NatureGard (registered trademark), Agrisure (registered trademark) GT Advantage (GA21 glyphosate-tolerant trait), Agrisure (registered trademark) CB Advantage (Bt11 corn borer (CB) trait), and Protecta (registered trademark).

[0292] Further examples of such transgenic crops are as follows: 1. Bt11 maize, Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31, 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize (Zea mays) conferred resistance to attacks by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of the cleavage-type Cry1Ab toxin. Bt11 maize has also acquired resistance to the herbicide glufosinate ammonium by transgenic expression of the enzyme PAT. 2. Bt176 maize, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize (Zea mays) conferred resistance to attacks by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of the cleavage-type Cry1Ab toxin. Bt176 maize has also acquired resistance to the herbicide glufosinate ammonium by transgenic expression of the enzyme PAT. 3. MIR604 maize, Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Maize conferred insect resistance by transgenic expression of modified Cry3A toxin. This toxin is Cry3A055, modified by insertion of a cathepsin-G protease recognition sequence. Preparation of such transgenic maize plants is described in International Publication No. 03 / 018810. 4. MON 863 maize, Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON 863 expresses the Cry3Bb1 toxin and is resistant to certain Coleoptera insects. 5. IPC 531 cotton, manufactured by Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02. 6. 1507 maize, manufactured by Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Genetically modified maize for the expression of the protein Cry1F to acquire resistance to certain Lepidoptera insects and the PAT protein to acquire resistance to the herbicide glufosinate ammonium. 7. NK603×MON810 maize, manufactured by Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. This is a conventional hybrid maize variety created by crossing the genetically modified variety NK603 with MON 810. NK603×MON 810 Maize genetically modifies the protein CP4 EPSPS, obtained from the Agrobacterium sp. strain CP4, which confers resistance to the herbicide Roundup® (which contains glyphosate), and also genetically modifies the Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki, which provides resistance to certain Lepidoptera, including the European corn borer.

[0293] As used herein, the term “habitat” means cultivated land on which plants grow, or on which seeds of cultivated plants are sown, or on which seeds will be sown in the soil. It includes soil, seeds and seedlings, and established vegetation.

[0294] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves, and fruits.

[0295] The term “plant propagation material” is understood to refer to plant materials, such as potatoes, including reproductive parts like seeds, and cuttings or tubers, that can be used for plant propagation. Examples include plant seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, and parts. Germinated plants and seedlings that will be transplanted after germination or emergence from the soil may also be included. These seedlings may be protected before transplantation by full or partial treatment by immersion. Preferably, “plant propagation material” is understood to mean seeds.

[0296] The pesticides referred to herein by their common names are publicly known, for example, from “The Pesticide Manual”, 19th Ed., British Crop Protection Council 2021.

[0297] Compounds of formula (I) as defined in this invention may be used in their unmodified form or, preferably, in combination with auxiliaries conventionally used in the art of formulation. For this purpose, they may be appropriately formulated by known methods into emulsifiable concentrates, coating pastes, ready-to-spray or dilutable solutions or suspensions, diluted emulsions, wettable powders, soluble powders, spray powders, granules, and also, for example, encapsulations in polymeric substances. As with the type of composition, the method of application, such as spraying, misting, powdering, granulation, coating or pouring, is selected according to the intended purpose and the circumstances at hand. The composition may also contain further auxiliaries such as stabilizers, defoamers, viscosity modifiers, binders or tackifiers, as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.

[0298] For example, suitable carriers and / or auxiliaries for agricultural applications may be solids or liquids and are substances useful in formulation techniques, such as natural or recycled inorganic substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders, or fertilizers. Such carriers are described, for example, in International Publication No. 97 / 33890.

[0299] A suspension concentrate is an aqueous formulation in which finely ground solid particles of an active compound are suspended. Such formulations contain anti-settling agents and dispersants, and may further contain wetting agents, defoaming agents, and crystal growth inhibitors to enhance activity. When used, these concentrates are diluted with water and typically applied as a spray to the area to be treated. The amount of the active ingredient may range from 0.5% to 95% of the concentrate.

[0300] Wettable powders are in the form of finely ground particles that disperse easily in water or other liquid carriers. The particles contain the active ingredient held within a solid matrix. Typical solid matrices include Fuller's earth, kaolin clay, silica, and other easily hygroscopic organic or inorganic solids. Wettable powders typically contain 5% to 95% of the active ingredient and small amounts of wetting agents, dispersants, or emulsifiers.

[0301] Emulsifying concentrates are homogeneous liquid compositions that are dispersible in water or other liquids and may consist solely of an active compound and a liquid or solid emulsifier, or they may also contain liquid carriers such as xylene, high-boiling aromatic naphtha, isophorone, and other non-volatile organic solvents. When used, these concentrates are dispersed in water or other liquids and typically applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.

[0302] Granular formulations include both extruded materials and relatively coarse particles and are typically applied undiluted to the area requiring treatment. Typical carriers for granular formulations include sand, fuller's soil, attapulgite clay, bentonite clay, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, gypsum, wood flour, crushed corn cobs, crushed peanut shells, sugars, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate, and other organic or inorganic materials that can absorb or be coated with the active compound. Granular formulations typically contain 5% to 25% active ingredients, which may include surfactants such as heavy aromatic naphtha, kerosene and other petroleum fractions, or vegetable oils; and / or stickers such as dextrin, glue or synthetic resins.

[0303] The powder for spraying is a free-flowing mixture of the active ingredient and finely ground solids such as talc, clay, powder, and other organic and inorganic solids that act as a dispersant and carrier.

[0304] Microcapsules are typically droplets or granules of an active ingredient encapsulated in an inert, porous shell that allows for the release of the encapsulated material into the surroundings at a controlled rate. Encapsulated droplets are typically 1 to 50 microns in diameter. The encapsulated liquid typically constitutes 50 to 95% of the capsule's weight and may include a solvent in addition to the active compound. Encapsulated granules are generally porous granules having a porous membrane that seals the pore openings of the granules, retaining the active species in liquid form within the granular pores. Granules are typically in the range of 1 millimeter to 1 centimeter in diameter, preferably 1 to 2 millimeters. Granules are formed by extrusion, agglomeration, or prilling, or they exist naturally. Examples of such materials include vermiculite, calcined clay, kaolin, attapulgite clay, sawdust, and granular carbon. Shell or membrane materials include natural and synthetic rubber, cellulosic materials, styrene-butadiene copolymers, polyacrylonitrile, polyacrylates, polyesters, polyamides, polyureas, polyurethanes, and starch xanthetes.

[0305] Other useful formulations for agricultural applications include simple solutions of the active ingredient in a solvent in which it is completely dissolved at the desired concentration, such as acetone, alkylated naphthalene, xylene, and other organic solvents. Pressurized sprayers may also be used, in which the active ingredient is dispersed in a finely pulverized form as a result of evaporation of a low-boiling point dispersible solvent carrier.

[0306] Suitable agricultural additives and / or carriers useful for formulating the compositions of the present invention in the above-mentioned formulation types are well known to those skilled in the art.

[0307] Examples of liquid carriers that can be used include water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetate, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidinone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-Trichloroethane, 2-Heptanone, Alpha-pinene, d-Limonene, Ethylene glycol, Ethylene glycol butyl ether, Ethylene glycol methyl ether, γ-Butyrolactone, Glycerol, Glycerol diacetate, Glycerol monoacetate, Glycerol triacetate, Hexadecane, Hexylene glycol, Isoamyl acetate, Isobornyl acetate, Isooctane, Isophorone, Isopropylbenzene, 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, Octadeca Examples include sodium phosphate, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol and amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol and other high molecular weight alcohols, ethylene glycol, propylene glycol, glycerin and N-methyl-2-pyrrolidinone. Water is generally a preferred carrier for diluting concentrates.

[0308] Suitable solid carriers include, for example, talc, titanium dioxide, pyroferrite clay, silica, attapulgite clay, diatomaceous earth (kieselguhr), white pigment, diatomaceous earth (diatomaxeous earth), lime, calcium carbonate, bentonite clay, fuller's earth, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, and lignin.

[0309] A wide range of surfactants are advantageously used in both the liquid and solid compositions, particularly those designed to be diluted with a carrier before application. These agents, when used, typically constitute 0.1% to 15% by mass of the formulation. They may be anionic, cationic, nonionic, or polymeric in nature and can be used as emulsifiers, wetting agents, suspending agents, or for other purposes. Typical surfactants include alkyl sulfate salts, e.g., diethanolammonium lauryl sulfate; alkylaryl sulfonates, e.g., calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, e.g., nonylphenol-C.sub.18 ethoxylate; alcohol-alkylene oxide addition products, e.g., tridecyl alcohol-C.sub.16 ethoxylate; soaps, e.g., sodium stearate; alkylnaphthalene sulfonate salts, e.g., sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, e.g., sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, e.g., sorbitol oleate; quaternary amines, e.g., lauryltrimethylammonium chloride; polyethylene glycol esters of fatty acids, e.g., polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono and dialkyl phosphate esters.

[0310] Other additives commonly used in agricultural compositions include crystallization inhibitors, viscosity modifiers, suspending agents, spray droplet regulators, pigments, antioxidants, foaming agents, defoaming agents, light-shielding agents, compatibilizers, defoaming agents, metal ion chelating agents, neutralizing agents and buffering agents, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, mitigating agents, lubricants and fixing agents.

[0311] In addition, other biocides or compositions may be combined with the compositions of the present invention and used in the methods of the present invention, and may be applied simultaneously with or sequentially to the compositions of the present invention. When applied simultaneously, these further active ingredients may be formulated together with the compositions of the present invention or mixed, for example, in a spray tank. These further biocides may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides, plant growth regulators, and / or biological formulations.

[0312] The following combinations of the compound of formula I and another active substance in a 1:1 weight ratio are preferred (where the abbreviation "TX" means "one compound selected from the compounds defined in Tables 1.1 to 1.144 and Table A"): (7E,9Z)-Dodeca-7,9-diene-1-ylacetate+TX, (9Z,11E)-Tetradeca-9,11-diene-1-ylacetate+TX, (9Z,12E)-Tetradeca-9,12-diene-1-ylacetate+TX, (E)-6-methylhepta-2-en-4-ol+TX, (E)-Deca-5-en-1-ylacetate and (E)-Deca-5-en-1-ol+TX, (E)-Trideca-4-en-1-ylacetate+TX, (E,Z)-Tetradeca-4,10-diene-1-ylacetate+TX Luacetate + TX, (Z)-Dodeca-7-en-1-Illacetate + TX, (Z)-Hexadeca-11-en-1-Illacetate + TX, (Z)-Hexadeca-11-Enal + TX, (Z)-Hexadeca-13-en-11-in-1-Illacetate + TX, (Z)-Icosa-13-en-10-on + TX, (Z)-Tetradeca-7-en-1-ar + TX, (Z)-Tetradeca-9-en-1-all + TX, (Z)-Tetradeca-9-en-1-Illacetate + TX, 1,2-Dibromo -3-chloropropane + TX, 1,2-dichloropropane + TX, 1,2-dichloropropane and 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-dichlorotetrahydrothiophene 1,1-dioxide + T X, 4-(quinoxaline-2-ylamino)benzenesulfonamide + TX, 4-methylnonan-5-ol and 4-methylnonan-5-one + TX, 5-methyl-6-thioxo-1,3,5-thiadiadinane-3-ylacetic acid + TX, 6-isopentenylaminopurine + TX, 8-hydroxyquinoline sulfate + TX, abamectin + TX, acequinosyl + TX, acetamiprid + TX, acetoprol + TX, acrinatrin + TX, acinonapyr + TX, Adoxophyes orana GV + TX, afidopiropene + TX, afoxolaner + TX, Agrobacterium radiobacter + TX,AKD-3088+TX, Aranicarb+TX, Aldicarb+TX, Aldoxycarb+TX, Arethrin+TX, Alpha-cypermethrin+TX, Alphamethrin+TX, Alpha-multistriatin+TX, Amblyseius spp.+TX, Amidoflumet+TX, Amino Acids+TX, Aminocarb+TX, Anagrapha falcifera NPV+TX, Anagrus atomus+TX, Aphelinus abdominalis+TX, Aphidius colemani+TX, Aphidoletes aphidimyza+TX, Aphoret+TX, Autographa californica NPV+TX, AZ 60541+TX, Azadirachtin+TX, Azocyclotin+TX, Bacillus aizawai+TX, Bacillus chitinosporus AQ746 (NRRL acceptance number B-21 618)+TX, Bacillus firmus+TX, Bacillus kurstaki+TX, Bacillus mycoides AQ726 (NRRL acceptance number B-21664)+TX, Bacillus pumilus (NRRL acceptance number B-30087)+TX, Bacillus pumilus AQ717 (NRRL acceptance number B-21662)+TX, Bacillus genus sp.)AQ175 (ATCC acceptance number 55608) + TX, Bacillus sp. AQ177 (ATCC acceptance number 55609) + TX, Bacillus sp. AQ178 (ATCC acceptance number 53522) + TX, Bacillus sphaericus Neide + TX, Bacillus subtilis AQ153 (ATCC acceptance number 55614) + TX,Bacillus subtilis AQ30002 (NRRL acceptance number B-50421) + TX, Bacillus subtilis AQ30004 (NRRL acceptance number B-50455) + TX, Bacillus subtilis AQ713 (NRRL acceptance number B-21661) + TX, Bacillus subtilis AQ743 (NRRL acceptance number B-21665) + TX, nonspecific Bacillus subtilis + TX, Bacillus thuringiensis AQ52 (NRRL acceptance number B-21619) + TX, Bacillus thuringiensis Bacillus thuringiensis)BD#32 (NRRL acceptance number B-21530) + TX, Bacillus thuringiensis Berliner + TX, Bacillus thuringiensis subsp. Aizawai + TX, Bacillus thuringiensis subsp. israelensis + TX, Bacillus thuringiensis subsp. Japonensis + TX, Bacillus thuringiensis subsp. Kurstaki + TX, Bacillus thuringiensis subsp. tenebrionis subsp.Tenebrionis)+TX, Bacillus thuringiensis subspec.kurstaki BMP 123+TX, Beauveria bassiana+TX, Beauveria brongniartii+TX, Bencrotiaz+TX, Benomyl+TX, Bensultap+TX, Benzoximate+TX, Benzpyrimoxane+TX, Betacyfluthrin+TX,Beta-cypermethrin + TX, bethoxazine + TX, bifenazate + TX, bifenthrin + TX, binapacril + TX, biorethrin + TX, biorethmethrin + TX, bis(tributyltin) oxide + TX, bisadily + TX, bistriflurone + TX, bisulfurfen + TX, brevicomin + TX, broflanilide + TX, broflutrinate + TX, bromoacetamide + TX, bromophos-ethyl + TX, bronopol + TX, busulfan + TX, butocarboxime + TX, butopyronoxyl + TX, butoxy(polypropylene glycol) Coal)+TX, Butylpyridaben+TX, Cadsaphos+TX, Calcium arsenate+TX, Carbaryl+TX, Carbofuran+TX, Carbon disulfide+TX, Carbosulfan+TX, Cartape+TX, CAS number: 1594624-87-9+TX, CAS number: 1922957-47-8+TX, CAS number: 1255091-74-7+TX, CAS number: 1365070-72-9+TX, CAS number: 1445683-71-5+TX, CAS number: 1445684-82-1+TX, CAS number: 1594626-19-3+TX, CAS number: 1 594637-65-6+TX, CAS number: 1632218-00-8+TX, CAS number: 1808115-49-2+TX, CAS number: 1922957-46-7+TX, CAS number: 1922957-48-9+TX, CAS number: 1956329-03-5+TX , CAS number:1990457-52-7+TX, CAS number:1990457-55-0+TX, CAS number:1990457-57-2+TX, CAS number:1990457-66-3+TX, CAS number:1990457-77-6+TX, CAS number:1990457- 85-6+TX, CAS number:2032403-97-5+TX, CAS number:2044701-44-0+TX, CAS number:2095470-94-1+TX, CAS number:2128706-04-5+TX, CAS number:2128706-05-6+TX, CAS number:2 133042-31-4+TX, CAS number:2133042-44-9+TX, CAS number:2171099-09-3+TX, CAS number:2220132-55-6+TX, CAS number:2396747-83-2+TX, CAS number:2408220-91-5+TX,CAS number: 2408220-94-8+TX, CAS number: 2415706-16-8+TX, Piperfuranilide (CAS number: 2615135-05-0)+TX, CAS number: 2719848-60-7+TX, CAS number: RNA (Colorado leaf beetle (Leptinotarsa ​​decemLineata)-specific recombinant double-strand interference GS2)+TX, Chlorantraniliprole+TX, Chlordane+TX, Chlorfenapyr+TX, Chloropicrin+TX, Chloroprarethrin+TX, Chlorpyrifos+TX, Chromafenozide+TX, Chrysoperla carnea)+TX, clenpyrine+TX, chloetocarb+TX, clothianidin+TX, chodrelua+TX, chodremon+TX, copper acetoarsenite+TX, copper dioctanoate+TX, copper hydroxide+TX, copper sulfate+TX, cresol+TX, cluthomate+TX, Cryptolaemus montrouzieri + TX, Kyurua + TX, Cyanophenphos + TX, Cyantraniliprole + TX, Sibutrin + TX, Cyclaniliprole + TX, Cyclobtrifluram + TX, Cycloprothrin + TX, Cycloxapride + TX, Cydia pomonella GV + TX, Cyenopyrafen + TX, Cietopyrafen + TX, Cyflumetofen + TX, Cyfluthrin + TX, Cyhalodian + TX, Shirohalothrin + TX, Cypermethrin + TX, Cyphenothrin + TX, Cyprofuranilide + TX, Cyromazine + TX, Cytokinin + TX, Dacnusa sibirica)+TX, dazomet+TX, DBCP+TX, DCIP+TX, deltamethrin+TX, diafenthiuron+TX, dialiphos+TX, diamidaphos+TX, dibrom+TX, dibutyl adipate+TX, dibutyl phthalate+TX, dibutyl succinate+TX, diclofenthion+TX, diclofenthion+TX, diclofen+TX, dichlorophene+TX, dicliphos+TX, dichloromezothiaz+TX, diethyltoluamide+TX, diflubenzuron+TX, Diglyphus sibirica isaea)+TX, dimatif+TX, dimethoate+TX, dimethylcarbate+TX, dimethyl phthalate+TX, dinpropyridaz+TX, dinactin+TX, dinocap+TX, dinotefuran+TX, dioxabenzophos+TX, dipirithione+TX, disparla+TX, D-limonene+TX, dodeca-8-en-1-ylacetate+TX, dodeca-9-en-1-ylacetate+TX, dodeca-8,10-dien-1-ylacetate+TX, dodicine+TX, dominicalle+TX, doramectin+TX, emamectin+TX, emamectin benzoate+TX, empenthrin+TX, Encarsia formosa)+TX, endotal+TX, endrin+TX, eprinomectin+TX, epsilon-monfluorothrin+TX, epsilon-metofluthrin+TX, desert dung wasp (Eretmocerus eremicus)+TX, esfenvalerate+TX, ethione+TX, ethiprole+TX, etoprophos+TX, 4-methyloctanoate ethyl+TX,Ethylhexanediol + TX, ethylene dibromide + TX, etofenprox + TX, etoxazole + TX, etopyrafen + TX, eugenol + TX, fermentation products derived from seaweed extract and melasse + TX, fermentation products derived from melasse containing seaweed extract and urea + TX, seaweed extract and fermented plant products + TX, fermented plant products containing seaweed extract and plant hormones, vitamins, EDTA-chelated copper, zinc, and iron + TX, femfur + TX, phenaminosulf + TX, phenamiphos + TX, phenazaquin + TX, fenfluthrin + TX, fenitro Thione + TX, Fenmezodithiaz + TX, Phenobucarb + TX, Phenothiocarb + TX, Phenoxycarb + TX, Fenpropathrin + TX, Fenpyrad + TX, Fenpyroximate + TX, Fensulfothion + TX, Fenthion + TX, Fentin + TX, Fentin acetate + TX, Fenvalerate + TX, Ferric phosphate + TX, Fipronil + TX, Flomethoquin + TX, Flonicamide + TX, Fluacrypyrim + TX, Fluazindolidine + TX, Fluazuron + TX, Flubendiamide + TX, Flubendimine + TX, F Luchlordiniliprole + TX, Flucitrinate + TX, Flucycloxurone + TX, Flucitrinate + TX, Fluensulfone [318290-98-1] + TX, Fluensulfone + TX, Fluphenelim + TX, Flufenprox + TX, Flufiprole + TX, Fluhexaphon + TX, Flumethrin + TX, Fluopyram + TX, Flupyradiflon + TX, Flupyrimin + TX, Flupyroxystrobin + TX, Fluralaner + TX, Fluvalinate + TX, Fluxamethamide + TX, Formaldehyde + TX, Fosthiazate + TX, Phosthietan + TX, Frontalin + TX, Furfural + TX, Gamma-cyhalotrin + TX, Gossyplure (registered trademark) (1:1 mixture of (Z,E) and (Z,Z) isomers of hexadeca-7,11-dien-1-yl acetate) + TX, Grandolure + TX, Grandolure I + TX, Grandolure II + TX, Grandolure III + TX, Grandolure IV + TX, Granulovirus + TX, Guadipyr + TX, GY-81 + TX, Halfenprox + TX, Halofenozide + TX, Harpin + TX,Helicoverpa armigera nuclear polyhedrosis virus + TX, Helicoverpa zea NPV + TX, Helicoverpa zea nuclear polyhedrosis virus + TX, Heliothis punctigera nuclear polyhedrosis virus + TX, Heliothis virescens nuclear polyhedrosis virus + TX, Hemel + TX, Hempa + TX, Heptafluthrin + TX, Heterophos + TX, Heterorhabditis bacteriophora and H. megidis + TX, Hexarua + TX, Hexaamide + TX, Hexithiazox + TX, Hypodamia conbergensis (concentrates) + TX, hydramethylnon + TX, hydralgafen + TX, slaked lime + TX, imisiaphos + TX, imidacloprid + TX, imiprothrin + TX, indazapiroxameth + TX, indoxacarb + TX, iodomethane + TX, iprodione + TX, ipsdienol + TX, ipsenol + TX, isamidophos + TX, isazofos + TX, isocycloserum + TX, isoflua Ranum (CAS number: 2892524-05-7) + TX, Isothioate + TX, Ivermectin + TX, Japonilua + TX, Kappa-bifenthrin + TX, Kappa-tefluthrin + TX, Kasugamycin + TX, Kasugamycin hydrochloride hydrate + TX, Kinetin + TX, Lambda-cyhalothrin + TX, Redoprona + TX, Lepimectin + TX, Fujikona long-horned parasitic wasp (Leptomastix) dactylopii)+TX, lineatin+TX, liturua+TX, lupurua+TX, rotilaner+TX, lufenuron+TX, Macrolophus caliginosus+TX, cutworm (Mamestra brassicae) NPV+TX, mecarfone+TX, medolua+TX, megatomoic acid+TX, metaflumizone+TX, metaldehyde+TX, metam+TX, metam-potassium+TX, metam-sodium+TX, Metaphycus helvolus+TX,Metarhizium anisopliae var. acridum + TX, Metarhizium anisopliae var. anisopliae + TX, species of the genus Metarhizium spp.)+TX, Metepa+TX, Methiocarb+TX, Methiotepa+TX, Methomyl+TX, Methquin-butyl+TX, Methoxyphenozide+TX, Methyl aphorate+TX, Methyl bromide+TX, Methyl eugenol+TX, Methyl isothiocyanate+TX, Methyl neodecanamide+TX, Metofluthrin+TX, Metolcarb+TX, Mexacalvert+TX, Milbemectin+TX, Milbemycin oxime+TX, Monfluorothrin+TX, Morzide+TX, Moxidectin+TX, Muscarua+TX, Muscodor albus 620 (NRRL acceptance number 30547)+TX, Muscodor roseus A3-5 (NRRL acceptance number 30548)+TX, Mulberry dark spot disease fungus (Myrothecium Verrucaria composition + TX, Nabam + TX, NC-184 + TX, Neem tree-based products + TX, Neodiprion sertifer NPV and N. lecontei NPV + TX, Nickel bis(dimethyldithiocarbamate) + TX, Niclosamide + TX, Niclosamide-olamine + TX, Nicofluprole + TX, Nitenpyram + TX, Nichiazine + TX, Nitrapyrine + TX, Octadeca-2,13-dien-1-ylacetate + TX, Octadeca-3,13-dien-1-ylacetate + TX, Octylinone + TX, Omethoate + TX, Orflurua + TX, Orius species spp.)+TX, orictalua+TX, ostramon+TX, oxamate+TX, oxamyl+TX, oxazosulfyl+TX, oxolinic acid+TX, oxytetracycline+TX, Paecilomyces fumosoroseus+TX, Paecilomyces lilacinus+TX, parathion-ethyl+TX,Pasteuria nishizawae + TX, Pasteuria penetrans + TX, Pasteuria ramosa + TX, Pasteuria thornei + TX, Pasteuria usgae + TX, P-cymene + TX, Penflurone + TX, Pentachlorophenol + TX, Permethrin + TX, Phenothrin + TX, Phorate + TX, Phosphamidone + TX, Phosphocarb + TX, Phytoseiulus persimilis + TX, Picalidine + TX, Pioxaniliprole + TX, Piperazine + TX, Piperonyl butoxide + TX, Pyrimicarb + TX, Pyrimiphos-ethyl + TX, Pyrimiphos-methyl + TX, Diamondback moth (Plutella) Xylostella granulovirus + TX, diamondback moth (Plutella) Xylostella) Nuclear Polyhedrosis Virus + TX, Polyhedrosis Virus + TX, Potassium and Molybdenum and EDTA Chelated Manganese + TX, Potassium Ethylxanthogenic Acid + TX, Potassium Hydroxyquinoline Sulfate + TX, Prallethrin + TX, Probenazole + TX, Profenofos + TX, Profluthrin + TX, Propargit + TX, Propetamphos + TX, Propoxur + TX, Prothiofos + TX, Protrifenbut + TX, Piflubmid + TX, Pymetrozine + TX, Pyraclofos + TX, Pyrafluprole + TX, Pyrethrum + TX, Pyridaben + TX, Pyridaryl + TX, Pyridine-4-amine + TX, Pyrifluquinazone + TX, Pyrimidifen + TX, Pyriminostrobin + TX, Pyriprole [394730-71-3] + TX, Pyriprole + TX, Pyriproxyfen + TX, QRD 420 (Terpenoid Blend) + TX, QRD 452 (terpenoid blend) + TX, QRD 460 (terpenoid blend) + TX, Soap tree (Quillaja saponaria) + TX, Quinoclamine + TX, Quinonamide + TX, Resmethrin + TX, Rhodococcus globerulus AQ719 (NRRL acceptance number B-21663) + TX, Saloraner + TX, S-Biorethrin + TX,Cebuphos + TX, Selamectin + TX, Sigrua + TX, Silafluofen + TX, Simazine + TX, Sodium Pentachlorophenoxide + TX, Solzidine + TX, Spidoxamato + TX, Spinetoram + TX, Spinosad + TX, Spirobudifen + TX, Spirodiclofen + TX, Spiromesifen + TX, Spiropidione + TX, Spirotetramato + TX, Spodoptera exigua Multicapsid Polyhedrosis Virus + TX, Spodoptera frugiperda Polyhedrosis Virus + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema feltiae (Steinernema feltiae)+TX, Steinernema glaseri+TX, Steinernema riobrave+TX, Steinernema riobravis+TX, Steinernema scapterisci+TX, Steinernema spp. species+TX, Streptomyces galbus (NRRL acceptance number 30232)+TX, Streptomyces sp.)(NRRL acceptance number B-30145)+TX, streptomycin+TX, streptomycin sesquisulfate+TX, strychnine+TX, sulcatol+TX, sulfiflumin (CAS number: 2377084-09-6)+TX, sulfoxaflor+TX, tadimucarb+TX, tebufenozide+TX, tebufenpyrad+TX, tebupirimiphos+TX, tecrophthalam+TX, tefluthrin+TX, temephos+TX, tepa+TX, tarbaam+TX, terbuphos+TX, terpenoid blend+TX, tetrachlorantraniliprole+TX, tetrachlorothiophene+TX, tetradeca-11-en-1-yl acetate+TX, tetradiphon+TX, tetramethrin+TX, tetramethylfluthrin+TX, tetranactin+TX, tetraniliprole+ TX, Theta-cypermethrin + TX, Thiacloprid + TX, Thiafenox + TX, Thiamethoxam + TX, Thiocyclam + TX, Thiodicarb + TX, Thiofanox + TX, Thiohempa + TX, Thiomersal + TX, Thiometon + TX, Thionadin + TX, Thiophanate + TX, Thiosultap + TX, Thiotepa + TX, Tigolaner + TX, Thiolantraniliprole + TX, Thioxazafen + TX, Tolfenpyrad + TX, Toxaphene + TX, Tralomethrin + TX, Transfluthrin + TX, Tretamine + TX, Triazamate + TX, Triazophos + TX, Triazurone + TX, Tributyltin oxide + TX, Trichlorfon + TX, Trichloronate + TX, Trichlorfon + TX, Species of the genus Trichogramma spp.)+TX, triphenmorph+TX, trifluenfronate+TX, triflumezopyrim+TX, trimedrua+TX, trimedrua A+TX, trimedrua B1+TX, trimedrua B2+TX, trimedrua C+TX, trimetacarb+TX, triphenyltin acetate+TX, triphenyltin hydroxide+TX, trunk-call+TX, cyclopyrazoflor+TX, Typhlodromus occidentalis+TX, uredepa+TX, Verticillium lecanii+TX, Verticillium spp.) + TX, xylenol + TX, YI-5302 + TX, zeatin + TX, zeta-cypermethrin + TX; N-[(1R)-1-benzyl-3-chloro-1-methylbuta-3-enyl]-8-fluoroquinoline-3-carboxamide+TX, N-[(1S)-1-benzyl-3-chloro-1-methylbuta-3-enyl]-8-fluoroquinoline-3-carboxamide+TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine (these compounds (These compounds may be prepared by the method described in International Publication No. 2019 / 110427) + TX, (3',4',5'-trifluorobiphenyl-2-yl)-amide + TX, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone (These compounds may be prepared by the method described in International Publication No. 2017 / 220485) + TX, (4-phenoxyphenyl) Tyl 2-amino-6-methylpyridine-3-carboxylate (this compound can be prepared by the method described in International Publication No. 2014 / 006945) + TX, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone + TX, (7E,9Z)-dodeca-7,9-diene-1-ylacetate + TX, (9Z,11E)-tetradeca-9,11-diene-1-ylacetate TX, (9Z,12E)-tetradeca-9,12-diene-1-ylacetate+TX, (E)-6-methylhepta-2-en-4-ol+TX, (E)-deca-5-en-1-ylacetate and (E)-deca-5-en-1-ol+TX, (E)-trideca-4-en-1-ylacetate+TX, (E,Z)-tetradeca-4,10-diene-1-ylacetate+TX, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, (Z)-dodeca-7-en-1-ylacetate + TX, (Z)-hexadeca-11-en-1-ylacetate + TX, (Z)-hexadeca-11-enal + TX, (Z)-hexadeca-13-en-11-in-1-ylacetate + TX, (Z)-icosa-13-en-10-one + TX, (Z)-tetradeca-7-en-1-al + TX, (Z)-tetradeca-9-en-1-ol + TX, (Z)-tetradeca-9-en-1-ylacetate + TX, (Z (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazole-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide (this compound can be prepared by the method described in International Publication No. 2018 / 153707) + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazole-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide + TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazole-1-yl]acetyl]-4-piperidyl]thiazole -4-yl]-4,5-dihydroisoxazole-5-yl]-3-chlorophenyl]methanesulfonic acid + TX, 1-(4,5-dimethylbenzimidazole-1-yl)-4,4,5-trifluoro-3,3-dimethylisoquinoline + TX, 1-(4,5-dimethylbenzimidazole-1-yl)-4,4-difluoro-3,3-dimethylisoquinoline + TX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridine-3-yl)-4,4,5-trifluoro-3,3-dimethylisoquinoline + TX, 1-(6,7-dimethylpyrazolo[ 1,5-a]pyridine-3-yl)-4,4,6-trifluoro-3,3-dimethylisoquinoline + TX, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridine-3-yl)-4,4-difluoro-3,3-dimethylisoquinoline (these compounds can be prepared by the method described in International Publication No. 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 and 1,3-Dichloropropene + TX, 1,3-Dichloropropene + TX, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea + TX, 1-[2-[[1-(4-chlorophenyl)pyrazole-3-yl]oxymethyl]-3-methylphenyl]-4-methyltetrazole-5-one + TX, 10-Diene-1-ylacetate + TX, 14-Methyloctadeca-1-ene + TX, 1-Bromo-2-chloroethane + TX, 1-Di Chloro-1-nitroethane + TX, 1-hydroxy-1H-pyridine-2-thione + TX, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea + TX, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazole-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxy Samide + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(1,3-dithiolan-2-yl)phenyldimethylcarbamate + TX, 2-(2-butoxyethoxy)ethylpiperonilate + TX, 2-(2-butoxyethoxy)ethylthiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenylmethylcarbamate + TX, 2-(4-chloro-3,5-xylyloxy)ethanol + TX, 2-(difluoromethyl) (Tyl)-N-(3-ethyl-1,1-dimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethylindan-4-yl]pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethylindan-4-yl]pyridine-3-carboxamide (This compound can be prepared by the method described in International Publication No. 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-ethylsulfinylethylmethyl phosphate + TX, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide + TX, 2,4-dichlorophenylbenzenesulfonate + TX, 2,6-dimethyl-1H,5H-[1,4]dimethyl Ino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetron (this compound can be prepared by the method described in International Publication No. 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-triazole-1-yl)propan-2-ol (this compound can be prepared by the method described in International Publication No. 2017 / 029179) (This compound can be prepared by the method described in International Publication No. 2017 / 029179) + TX, 2-chlorovinyl diethyl phosphate + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide + TX, 2-imidazolidone + TX, 2-isovalerylindan-1,3-dione + TX, 2-methyl(propa-2-inyl)aminophenylmethylcarbamate T+TX, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide (this compound may be prepared by the method described in International Publication No. 2018 / 065414) + TX, 2-thiocyanatoethyl laurate + TX, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole (these compounds may be prepared by the method described in International Publication No. 2016 / 156085) + TX, 3-(4,4-Difluoro-3,4-Dihydro-3,3-dimethylisoquinoline-1-yl)quinolone + TX, 3-(4-chlorophenyl)-5-methylrhodanine + 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 is from International Publication No. 2016 / 1 (Can be prepared by the method described in International Publication No. 56290) + TX, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitride (This compound can be prepared by the method described in International Publication No. 2016 / 156290) + TX, 3-bromo-1-chloropropa-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-oxadiazole-3-yl]phenyl]methyl]urea + TX, 3-methyl-1-phenylpyrazole-5-yldimethylcarbamate + TX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine-3-carbonitrile + TX, 4-(2-bromo-4-fluorophenyl)-N-( 2-Chloro-6-fluorophenyl)-2,5-dimethylpyrazole-3-amine + TX, 4-(quinoxaline-2-ylamino)benzenesulfonamide + TX, 4,4-difluoro-1-(5-fluoro-4-methylbenzimidazole-1-yl)-3,3-dimethylisoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridine-3-yl)isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridine-3-yl)isoquinoline + TX, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazole-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-triazole-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-triazole-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + TX, 4-chlorophenylphenyl sulfone + TX, 4-methyl(propane-2-inyl)amino-3,5-xylylmethylcarbamate + TX,4-methylnonan-5-ol and 4-methylnonan-5-one + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohexa-2-enone + TX, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one + TX, 5,5-dimethyl-3-oxocyclohexa-1-enyldimethylcarbamate + TX, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, 5-methyl-6-thioxo-1,3 ,5-thiadiadinane-3-ylacetic acid + TX,6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methylpyridazine-4-carboxamide (may be prepared from the method described in International Publication No. 2020 / 109391) + TX,6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methylpyridazine-4-carboxamide (International Publication No. 2020 / 109 (May be prepared from the method described in International Publication No. 391) + TX, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazole-1-yl)isoquinoline + TX, 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide (May be prepared from the method described in International Publication No. 2020 / 109391) + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c] Sothiazole-3-carbonitride + TX, 6-isopentenylaminopurine + TX, 8-fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, 8-hydroxyquinoline sulfate + TX, acetylone + TX, acetoprol + TX, acibenzolar + TX, acibenzolar-S-methyl + TX, acrylonitrile + TX,Adoxophyes orana GV+TX, Agrobacterium radiobacter+TX, Aldoxycarb+TX, Aldrin+TX, Allosamidin+TX, Alixicarb+TX, Alpha-chlorohydrin+TX, Alpha-ecdysone+TX, Alpha-multistriatin+TX, Aluminum phosphide+TX, Amblyseius spp.+TX, Amectotractin+TX, Ametoctrazine+TX, Amidithione+TX, Amidothioate+TX, Aminocarb+TX, Aminopyriphen+TX, Amisulbrom+TX, Amiton+TX, Amiton hydrogen oxalate+TX, Amitraz+TX, Anabacin+TX, Anagrapha farcifera falcifera) NPV+TX, Anagrus atomus+TX, Ancimidor+TX, Anilazine+TX, Anisifuruprin+TX, Anthraquinone+TX, Antzu+TX, Aphelinus abdominalis+TX, Aphidius colemani+TX, Aphidoletes aphidimyza+TX, Aphorate+TX, Aramite+TX, Arsenic trioxide+TX, Atidathion+TX, Autographa californica NPV+TX, Azaconazole+TX, Azamethiphos+TX, Azobenzene+TX, Azothoate+TX, Azoxystrobin+TX, Bacillus sphaericus Neide)+TX, Bacillus thuringiensis delta-endotoxin+TX, barium carbonate+TX, barium hexafluoridosilicate+TX, barium polysulfide+TX, Bartholin+TX, Bayer 22 / 190+TX, Bayer 22408+TX, Beauveria brongniartii+TX, Benalaxyl+TX, Bencrotiaz+TX, Benomyl+TX, Benoxaphos+TX, Bentiavaricarb+TX, Benzothiostrobin+TX,Benzovindiflupir + TX, benzyl benzoate + TX, beta-cyfluthrin + TX, beta-cypermethrin + TX, bethoxazine + TX, bioetanomethrin + TX, biopermethrin + TX, bis(2-chloroethyl) ether + TX, bis(tributyltin) oxide + TX, bisadily + TX, bisthiosemi + TX, bitertanol + TX, bixafen + TX, blastosidine-S + TX, borax + TX, Bordeaux mixture + TX, boscalid + TX, brevicomin + TX, brodifacum + TX, brofenvalerate + TX, bromaggio Ron+TX, Bromethalin+TX, Bromfenbinphos+TX, Bromoacetamide+TX, Bromocyclene+TX, Bromo-DDT+TX, Bromophos+TX, Bromopropylate+TX, Bromuconazole+TX, Bronopol+TX, Bufencarb+TX, Bupirimate+TX, Buprofezin+TX, Busulfan+TX, Buta-3-inyl N-[6-[[(Z)-[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate+TX, Butacarb+TX, Butathiophos+TX, Butocarboxime+TX, Butonate+TX, Butopyronoxyl+TX, Butoxy(polypropylene glycol)+TX, Butoxycarboxime+TX, Butylpyridabene+TX, Calcium arsenate+TX, Calcium cyanide+TX, Calcium polysulfide+TX, Campechlor+TX, Captahole+TX, Captan+TX, Carbanolate+TX, Carbendazim+TX, Carbon disulfide+TX, Carbon tetrachloride+TX, Carbophenothion+TX, Carboxine+TX, Cartap hydrochloride+TX, CAS number: 2132414-04-9+TX, CAS number Product code: 2344721-61-3+TX, Sebazin+TX, Quinomethionate+TX, Chloralose+TX, Chlorbenside+TX, Chlorbicyclene+TX, Choldane+TX, Chlordecone+TX, Chlordimeform+TX, Chlordimeform hydrochloride+TX, Chlorphenetol+TX, Chlorphenthone+TX, Chlorophenolfide+TX, Chlorobenzylate+TX, Chloroform+TX, Chloroinconazide+TX, Chloromebform+TX, Chloromethirone+TX, Chloroneb+TX, Chlorophacinone+TX, Chloropicrin+TX,Chloropropylate + TX, Chlorothalonil + TX, Chlorphoxime + TX, Chlorprazofos + TX, Chlorthiofos + TX, Clozolinate + TX, Cholecalciferol + TX, Chrysoperla carnea + TX, Synerin I + TX, Synerin II + TX, Synerins + TX, Cysmethrin + TX, Cis-resmethrin + TX, Crocitrin + TX, Closantel + TX, Chodrelua + TX, Chodremon + TX, Copper acetosate + 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, Bear Chloride + TX, Coumafuryl + TX, Coumaphos + TX, Coumatetralyl + TX, Cumethoxystrobin (Diaxiangjunzhi) + TX, Cumithoate + TX, Comoxystrobin + TX, Cresol + TX, Crimidine + TX, Crotamiton + TX, Crotoxyphos + TX, Curuhomet + TX, Cryolite + TX, Cryptolaemus Montrouzieri) + TX, CS 708 + TX, Kyurua + TX, Cufraneb + ​​TX, Cyanophenphos + TX, Cyanophos + TX, Cyanthoate + TX, Cyazofamide + TX, Sibutrin + TX, Cicletorin + TX, Cyclobtriflurum + TX, Cydia pomonella GV + TX, Cyflufenaamide + TX, Simiazole + TX, Cymoxanil + TX, Cyproconazole + TX, Cyprodinil + TX, Cithioate + TX, Cytokinin + TX, Dacnusa sibirica)+TX, DAEP+TX, dazomet+TX, DCIP+TX, DCPM+TX, DDT+TX, debacarb+TX, decarbofuran+TX, demefion+TX, demefion-O+TX, demefion-S+TX, demeton-methyl+TX, demeton-O+TX, demeton-O-methyl+TX, demeton-S+TX, demeton-S-methyl+TX, demeton-S-methylsulfone+TX, diamidaphos+TX, dibutyl adipate+TX, dibutyl phthalate+TX, dibutyl succinate+TX, dikapton+TX, diclobentiazox+TX, diclofenthion+TX, diclofluanide+TX, diclon+TX,Dichlorophene + TX, Dichlorvos + TX, Diclozoline + TX, Dicrifos + TX, Diclosimet + TX, Diclomedin + TX, Dichloran + TX, Diclesil + TX, Dicyclanil + TX, Dicyclopentadiene + TX, Dieldrin + TX, Dienochlor + TX, Dietofencarb + TX, Diethyl 5-methylpyrazole-3-yl phosphate + TX, Diethyltoluamide + TX, Diphenacum + TX, Difenoconazole + TX, Difethiaron + TX, Diflovidazine + TX, Diglyphus (Isaea dwarf wasp) isaea)+TX, Zirol+TX, Dimatif+TX, Dimefluthrin+TX, Dimehox+TX, Dimethane+TX, Dimethyrimol+TX, Dimethomorph+TX, Dimethrin+TX, Dimethylcarbate+TX, Dimethylvinphos+TX, Dimethilane+TX, Dimoxystrobin+TX, Dynex+TX, Dynex-Dicrexin+TX, Diniconasol+TX, Dinocap-4+TX, Dinocap-6+TX, Dinoctone+TX, Dinopenton+TX, Dinoprop+TX, Dinosam+TX, Dinoseb+TX, Dinosulfone+TX, Dinoterbone+TX, Geophenolane +TX, Dioxabenzophos +TX, Dioxathion +TX, Diphacinone +TX, Diphenylsulfone +TX, Dipimethitron +TX, Dipirithione +TX, Dispara +TX, Disulfira +TX, Dithianone +TX, Diticlophos +TX, DNOC +TX, Dodeca-8-en-1-yl acetate +TX, Dodeca-9-en-1-yl acetate +TX, Dodeca-8 +TX, Dodemorph +TX, Dodicin +TX, Dozin +TX, Dofenapine +TX, Dominicalle +TX, Doramectin +TX, DSP +TX, d-tetramethrin +TX, Ecdysterone +TX, Edifenphos +TX, EI 1642+TX, EMPC+TX, Encarsia formosa+TX, Endotar+TX, Endothion+TX, Enestrobrin+TX, Enoxastrobin+TX, EPBP+TX, Epoxyconazole+TX, Eprinomectin+TX, Eretmocerus eremicus+TX, Ergocalciferol+TX, Etaphos+TX, Etaboxam+TX, Ethiofencarb+TX,Ethilimol + TX, ethoate-methyl + TX, ethyl 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-propa-1-enoxy]phenyl]methyl]pyrazole-3-carboxylate (may be prepared by the method described in International Publication No. 2020 / 056090) + TX, ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate (may be prepared by the method described in International Publication No. 2020 / 056090) + TX, ethyl 1-[[4-[5-( (Trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate + TX, ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate (this compound can be prepared by the method described in International Publication No. 2018 / 158365) + TX, ethyl 4-methyloctanoate + TX, ethyl formate + TX, ethyl hexanediol + TX, ethylene dibromide + TX, ethylene dichloride + TX, ethylene oxide + T X, Etridiazole + TX, Etrimophos + TX, Eugenol + TX, EXD + TX, Famoxadone + TX, Farnesol + TX, Farnesol and Nerolidol + TX, Fenamidom + TX, Phenaminosulf + TX, Phenaminestrobin + TX, Phenalimol + TX, Phenazaflor + TX, Fenbuconazole + TX, Fenbutatin oxide + TX, Fenchlorphos + TX, Phenetacarb + TX, Fenflam + TX, Fenhexamide + TX, Fenitrothion + TX, Phenothicarb + TX, Phenoxacrim + TX, Fe Noxanil + TX, Fenpiclonil + TX, Fenpicoxamide + TX, Fenpyritrin + TX, Fenpropidine + TX, Fenpropimorph + TX, Fenpyrad + TX, Fenpyrazamine + TX, Fenpyroximate + TX, Fenson + TX, Fensulfothione + TX, Fenthion + TX, Fenthion-ethyl + TX, Fentin + TX, Fentriphanil + TX, Farbam + TX, Ferimzon + TX, Ferric phosphate + TX, Furocumafen + TX, Florylpicoxamide + TX, Fluazinam + TX, Fluveneteram + TX,Flubendimine + TX, Flucoflon + TX, Flucycloxlon + TX, Fludioxonil + TX, Fluenetil + TX, Fluphenoxadiazam + TX, Fluphenoxystrobin + TX, Fluindapir + TX, Flumethylsulfolimu + TX, Flumorph + TX, Fluopicolide + TX, Fluopimomid + TX, Fluopyram + TX, Fluolbenside + TX, Fluoroacetamide + TX, Fluorimide + TX, Fluoxapiproline + TX, Fluoxastrobin + TX, Fluoxythioconazole + TX, Flupropazine + TX, Flupropazine hydrochloride + TX, Fluquinconazole + TX, Flusilazole + TX, Flusulfamide + TX, Fluthianil + TX, Flutolanil + TX, Flutriahol + TX, Fluxapiroxad + TX, FMC 1137+TX, Forpet+TX, Formaldehyde+TX, Formetanate+TX, Formetanate Hydrochloride+TX, Formparanate+TX, Fosetil-Aluminum+TX, Fosmethilan+TX, Fosspire+TX, Fosthietan+TX, Frontalin+TX, Fuberidazole+TX, Flalaxil+TX, Flamethopyr+TX, Flathiocarb+TX, Freslin+TX, Furfural+TX, Gamma-HCH+TX, Gliodin+TX, Grandolure+TX, Grandolure I+TX, Grandolure II+TX, Grandolure III+TX, Grandolure IV+TX, Guazatine+TX, Guazatine Acetate+TX, Halfenprox+TX, HCH+TX, Hemel+TX, Hempa+TX, HEOD+TX, Heptachlor+TX, Heterophos+TX, Heterorhabditis bacteriophora bacteriophora) and H. megidis + TX, hexaconazole + TX, hexadecylcyclopropane carboxylate + TX, hexaamide + TX, HHDN + TX, Hippodamia convergens + TX, hydralgafen + TX, slaked lime + TX, hydrogen cyanide + TX, himexazole + TX, hikincarb + TX, imanin + TX, imazalil + TX, imibenconazole + TX, iminoctadine + TX, impulfluxam + TX, ipconazole + TX, ipfentrifluconazole + TX,Ipflufenoquine + TX, Iprobenphos + TX, Iprodione + TX, Iprovalicarb + TX, Ipsdienol + TX, Ipsenol + TX, IPSP + TX, Isamidophos + TX, Isazofos + TX, Isobenzane + TX, Isocarbophos + TX, Isodrine + TX, Isofenphos + TX, Isofetamide + TX, Isoflucipram + TX, Isolane + TX, Isoprothiolane + TX, Isopyrazam + TX, Isothianil + TX, Isoxathion + TX X, Japonilua + TX, Jasmolin I + TX, Jasmolin II + TX, Iodophenphos + TX, Juvenile Hormone I + TX, Juvenile Hormone II + TX, Juvenile Hormone III + TX, Cadetrin + TX, Kasugamycin + TX, Kasugamycin Hydrochloride Hydrate + TX, Kereban + TX, Kinetin + TX, Quinoprene + TX, Kresoxim-Methyl + TX, Lead Arsenate + TX, Leptomastix dactylopii + TX, Leptophos + TX, Lindane + TX, Lineatin + TX, Lilimphos + TX, Littleua + TX, Lupulua + TX, Rubenmixianan + TX, Litidathion + TX, Macrolophus caliginosus + TX, Magnesium Phosphate + TX, Malonoben + TX, Mamestra brassicae) NPV+TX, mancapper+TX, manzeb+TX, mandestrobin+TX, mandipropamide+TX, maneb+TX, mazidoc+TX, m-cumenylmethylcarbamate+TX, mecarbam+TX, mecarbhon+TX, medolua+TX, mefentrifluconazole+TX, megatomoic acid+TX, menazone+TX, mepanipyrim+TX, meperfluthrin+TX, mephosphorane+TX, mepronil+TX, mercuric oxide+TX, mercurous chloride+TX, mesulfen+TX, mesulfenphos+TX, metalaxyl+TX, metam+TX, metam-potassium+TX, metam-sodium+TX, Metaphycus helvolus+TX, Metarhizium anisopliae var. acridum+TX,Metarhizium anisopliae var. anisopliae + TX, metharyl picoxamide + TX, metconazole + TX, metepa + TX, methacryphos + TX, methanesulfonic acid fluoride + TX, metasulfocarb + TX, methiotepa + TX, metoclotophos + TX, methoprene + TX, metoquin-butyl + TX, methotrin + TX, methoxychlor + TX, methyl(Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxypropane-2-enoate + TX, methyl(Z)-2-(5-cyclopentyl-2-methylphenoxy) (Z)-3-methoxypropa-2-enoate (These compounds can be prepared from the method described in International Publication No. 2020 / 193387) + TX, Methyl(Z)-2-[5-(3-isopropylpyrazole-1-yl)-2-methylphenoxy]-3-methoxypropa-2-enoate + TX, Methyl(Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazole-1-yl)phenoxy]propa-2-enoate + TX, Methyl(Z)-3-methoxy-2-[2-methyl-5-(4-propyltriazole- 2-yl)phenoxy]propa-2-enoate + TX, methyl(Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazole-1-yl]phenoxy]propa-2-enoate (these compounds can be prepared from the method described in International Publication No. 2020 / 079111) + TX, methyl(Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazole-2-yl]phenoxy]propa-2-enoate + TX, methyl aphorate + TX, methyl bromide + TX, methyl oil Genol + TX, methyl isothiocyanate + TX, methyl N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazole-4-yl]-2-methyl-phenyl]methyl]carbamate (may be prepared from the method described in International Publication No. 2020 / 097012) + TX, methyl N-[[4-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazole-4-yl]-2-methyl-phenyl]methyl]carbamate (may be prepared from the method described in International Publication No. 2020 / 097012) + TX,Methyl N-[[5-[4-(2,4-dimethylphenyl)triazole-2-yl]-2-methylphenyl]methyl]carbamate + TX, methylchloroform + TX, methylene chloride + TX, methylneodecanamide + TX, methylram + TX, methylcarb + TX, metminostrobin + TX, methoxadiazone + TX, metraphenone + TX, methyltetraprole + TX, MGK 264 + TX, milbemycin oxime + TX, mipahox + TX, myrex + TX, monoclotophos + TX, morphothion + TX, molzide + TX, moxidectin + TX, muscarua + TX, mycrobutanil + TX, microzolin + TX, mulberry dark spot fungus (Myrothecium) verrucaria) composition + TX, N-((1R)-1-benzyl-3-chloro-1-methyl-buta-3-enyl)-8-fluoro-quinoline-3-carboxamide (These compounds can be prepared by the method described in International Publication No. 2017 / 153380) + TX, N-((1S)-1-benzyl-3-chloro-1-methyl-buta-3-enyl)-8-fluoro-quinoline-3-carboxamide (These compounds can be prepared by the method described in International Publication No. 2017 / 153380) + TX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine + TX, N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine + TX, N,2-dimethoxy-N-[[4 -[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide + TX, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine (These compounds are described in International Publication No. 2017 / 055473, International Publication No. 2017 / 0 (May be prepared by the methods described in International Publication No. 55469, International Publication No. 2017 / 093348 and International Publication No. 2017 / 118689) + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoroquinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoroquinoline-3-carboxamide + TX,N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoroquinoline-3-carboxamide+TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoroquinoline-3-carboxamide+TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoroquinoline-3-carboxamide+TX, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoroquinoline-3-carboxamide+TX, N-[(E)-Me [Toxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide + TX, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide + TX, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide + TX, N-[2-[2,4-dichlorophenoxy]phenyl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide + TX, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide + TX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared by the method described in International Publication No. 2016 / 202742) + TX, N'-[4-(4,5-dichlorothiazole-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX, N'-[ 5-Bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine (These compounds can be prepared by the method described in International Publication No. 2015 / 155075) + TX, N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (This compound,(Can be prepared by the method described in IPCOM000249876D) + TX, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N-[N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide (These compounds may be prepared by the method described in International Publication No. 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 may be prepared by the method described in International Publication No. 2018 / 228896) + TX, Nabam + TX, Naphthalophos + TX, Nared + TX, Naphthalene + TX, NC-170 + TX, Pine sawfly (Neodiprion)N. sertifer) NPV and N. lecontei NPV + TX, nerolidol + TX, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-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, niclosamide-olamine + TX, nicotine + TX, nicotine sulfate + TX, niflulidide + TX, niccomycin + TX, N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine + TX, nithiazine + TX, nitrapyrine + TX, nitrilacarb + TX, ni Trilacarb 1:1 zinc chloride complex + TX, nitrotar-isopropyl + TX, N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide + TX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide + TX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl] Sadiazole-3-yl]benzenecarbothioamide + TX, norbolmid + TX, nualimol + TX, O,O,O',O'-tetrapropyldithiopyrophosphate + TX, octadeca-2,13-dien-1-yl acetate + TX, octadeca-3,13-dien-1-yl acetate + TX, octylinone + TX, oflace + TX, oleic acid + TX, omethoate + TX, orflurua + TX, species of the genus Orius spp.)+TX, Orictalua+TX, Orysastrobin+TX, Ostramon+TX, Oxadixyl+TX, Oxamate+TX, Oxatiapiproline+TX, Oxine-copper+TX, Oxolinic acid+TX, Oxocarboxyne+TX, Oxideprophos+TX, Oxydisulfon+TX, Oxytetracycline+TX, Paclobutrazol+TX, Paecilomyces humosoroseusFumosoroseus) + TX, Para-dichlorobenzene + TX, Parathion + TX, Parathion-methyl + TX, Pefurazoate + TX, Penconazole + TX, Pencyclon + TX, Penflufen + TX, Penflulon + TX, Pentachlorophenol + TX, Pentachlorophenyl laurate + TX, Penthiopyrad + TX, Permethrin + TX, PH 60-38 + TX, Phenamacryl + TX, Fenkapton + TX, Fosacetim + TX, Phosalon + TX, Phosdiphen + TX, Phospholepha + TX, Phosphorane + TX, Phosglycine + TX, Phosnichlor + TX, Phosphamide + TX, Phosphine + TX, Phoxime-methyl + TX, Phthalide + TX, Predatory mites (Phytoseiulus)persimilis)+TX, picarbtrazox+TX, picaridin+TX, picoxystrobin+TX, pindone+TX, piperazine+TX, piperonyl butoxide+TX, piprotal+TX, pyrimetaphos+TX, polychlorodicyclopentadiene isomer+TX, polychloroterpene+TX, polynactin+TX, polyoxin+TX, potassium arsenite+TX, potassium ethylxanthogenicate+TX, potassium hydroxyquinoline sulfate+TX, potassium thiocyanate Mu+TX, pp'-DDT+TX, Precosen I+TX, Precosen II+TX, Precosen III+TX, Primidophos+TX, Probenazole+TX, Prochloraz+TX, Proclonol+TX, Procymidone+TX, Profluthrin+TX, Promacil+TX, Promecarb+TX, Propamocarb+TX, Propiconazole+TX, Propineb+TX, Propoxur+TX, Propropyl isomer+TX, Proquinazide+TX, Protidathion+TX, Prothioconazole +TX, Prothiophos +TX, Protoate +TX, Pidiflumetofen +TX, Pyraclostrobin +TX, Pyramethostrobin +TX, Pyraoxystrobin +TX, Pyrapropoin +TX, Pyraziflumid +TX, Pyrazophos +TX, Pyrethmetrin +TX, Pyrethrin I +TX, Pyrethrin II +TX, Pyrethrin +TX, Pyribencarb +TX, Pyridaclomethyl +TX, Pyridafenthion +TX, Pyridine-4-amine +TX, Pyriphenox +TX, Pyri Methanil + TX, Pyrimitate + TX, Pyrimorph + TX, Pyrinulone + TX, Pyriophenone + TX, Pyrisoxazole + TX, Pyrroquilon + TX, Cassia + TX, Quinalphos + TX, Quinalphos-methyl + TX, Quinoclamine + TX, Quinofumeline + TX, Quinonamide + TX, Quinotion + TX, Quinoxyfen + TX, Quinthiophos + TX, Quintozen + TX, R-1492 + TX, Lafoxanide + TX, Resmethrin + TX, Japanese knotweed (Reynoutria japonica)Sachalinensis extract + TX, Ribavirin + TX, R-metalaxyl + TX, Rotenone + TX, Lianya + TX, Lianodine + TX, S421 + TX, Sabajira + TX, Shuladan + TX, Siriloside + TX, Seboctilamine + TX, Cebuphos + TX, Sedaxane + TX, Selamectin + TX, Sesamex + TX, Sesasmorin + TX, SI-0009 + TX, Siglua + TX, Simazine + TX, Simeconazole + TX, Sub Sodium arsenate + TX, sodium cyanide + TX, sodium fluoride + TX, sodium fluoroacetate + TX, sodium hexafluorosilicate + TX, sodium pentachlorophenoxide + TX, sodium selenate + TX, sodium tetrathiocarbonate + TX, sodium thiocyanate + TX, sofamide + TX, sordidine + TX, spiroxamine + TX, SSI-121 + TX, Steinernema viviones *Steinernema bibionis* + TX, *Steinernema carpocapsae* + TX, *Steinernema feltiae* + TX, *Steinernema glaseri* + TX, *Steinernema riobrave* + TX, *Steinernema riobravis* + TX, *Steinernema scapterisci* + TX, *Steinernema* species(spp.) + TX, Streptomycin + TX, Streptomycin sesquisulfate + TX, Strychnine + TX, Sulcatol + TX, Sulcoflon + TX, Sulcoflon-sodium + TX, Sulfiram + TX, Sulfuramide + TX, Sulfotep + TX, Sulfoxide + TX, Sulfur + TX, Sulfuryl fluoride + TX, Sulprophos + TX, Tar oil + TX, Tau-fluvalinate + TX, Tadimucarb + TX, TDE + TX, Tebuconazole + TX, Tebufloxin + TX, Tebupyrimphos + TX, Tecrofta Ram+TX, Temephos+TX, Tepa+TX, TEPP+TX, Terarethrin+TX, Turbam+TX, tert-butyl N-[6-[[[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate+TX, tetrachloroethane+TX, tetrachlorothiophene+TX, tetraconazole+TX, tetradeca-11-en-1-yl acetate+TX, tetradiphon+TX, tetramethylfluthrin+TX, tetrasul+TX, thallium sulfate+TX, thiabenda Zol+TX, Thiafenox+TX, Thiapronil+TX, Cyclophos+TX, Tifluzamide+TX, Thiocarboxyme+TX, Thiocyclam+TX, Thiocyclam oxalate+TX, Thiodiazole copper+TX, Thiofanox+TX, Thiohempa+TX, Thiomersal+TX, Thiometon+TX, Thionadin+TX, Thiophanate+TX, Thiophanate-methyl+TX, Thioquinox+TX, Thiosultap+TX, Thiosultap-sodium+TX, Thiotepa+TX, Thyram+TX, Turingien Syn+TX, Thiazinyl+TX, Tolchlorophos-methyl+TX, Tolprocarb+TX, Trilfluanide+TX, Tralomethrin+TX, Transpermethrin+TX, Tretamine+TX, Triadimefone+TX, Triadimenol+TX, Triamiphos+TX, Triatene+TX, Triazamate+TX, Triazophos+TX, Triazoxide+TX, Triazurone+TX, Tributyltin oxide+TX, Trichlormetaphos-3+TX, Trichloronate+TX, Species of the genus Trichogrammaspp.)+TX, Triclopyricarb+TX, Tricyclazole+TX, Tridemorph+TX, Triphenmorph+TX, Triphenofos+TX, Trifloxystrobin+TX, Triflumizole+TX, Triforine+TX, Trimedrua+TX, Trimedrua A+TX, Trimedrua B1+TX, Trimedrua B2+TX, Trimedrua C+TX, Trimetacarb+TX, Trinactin+TX, Trinexapac+TX, Triphenyltin acetate+TX, Triphenyltin hydroxide+TX, Triplene+TX, Triticonazole+TX, Trunc-call+TX, Typhlodromus occidentalis Occidentalis + TX, Uredepa + TX, Validamycin + TX, Valifenarate + TX, Bamidthion + TX, Vaniliprole + TX, Veratridine + TX, Veratrin + TX, Berbutin + TX, Verticillium lecanii + TX, Vinclozoline + TX, Warfarin + TX, XMC + TX, Xylenol + TX, Zeatin + TX, Zetametrin + TX, Zhongshengmycin + TX, Zinc naphthenate + TX, Zinc phosphide + TX, Thiazole zinc + TX, Zineb + ​​TX, Ziram + TX, Zolaprofos + TX; Acinetobacter lwoffii + TX, Acremonium alternatum + TX, Acremonium cephalosporium + TX, Acremonium diospyri + TX, Acremonium obclavatum + TX, Adoxophyes orana granulovirus (AdoxGV) (Capex®) + TX, Agrobacterium radiobacter strain K84 (Galltrol-A®) + TX, Alternaria alternate + TX, Alternaria cassia + TX, Alternaria destoluene (Alternaria destruens)(Smolder(registered trademark))+TX, Ampelomyces quisqualis(AQ10(registered trademark))+TX, Aspergillus flavus AF36(AF36(registered trademark))+TX, Aspergillus flavus NRRL 21882(Aflaguard(registered trademark))+TX, species of the genus Aspergillus (Aspergillus spp.)+TX, Aureobasidium pullulans+TX, Azospirillum (MicroAZ®, TAZO B®)+TX, Azotobacter+TX, Azotobacter chroocuccum (Azotomeal®)+TX, Azotobacter cysts (Bionatural Blooming Blossoms®)+TX, Bacillus amyloliquefaciens+TX, Bacillus cereus+TX, Bacillus chitinosporus strain AQ746+TX, Bacillus Bacillus chitinosporus strain CM-1 + TX, Bacillus circulans + TX, Bacillus firmus (BioSafe®, BioNem-WP®), especially strain CNMC 1-1582 (e.g., VOTIVO® from BASF SE) + TX, Bacillus licheniformis strain 3086 (EcoGuard®, Green Releaf®) + TX, Bacillus licheniformis strain HB-2 (Biostart®, formerly Rhizoboost®) + TX, Bacillus macerans + TX, Bacillus marismortui + TX, Bacillus megatherium megaterium)+TX, Bacillus mycoides strain AQ726+TX, Bacillus papillae (Milky Spore Powder®)+TX, Bacillus pumilus spp.)+TX, Bacillus pumilus strain AQ717+TX, Bacillus pumilus strain GB34 (Yield Shield®)+TX, Bacillus pumilus strain QST 2808 (Sonata®, Ballad Plus®)+TX, Bacillus sphaericus (VectoLex®)+TX, Bacillus spp. +TX, Bacillus spp. strain AQ175+TX, Bacillus spp. strain AQ177+TX, Bacillus spp. spp.) strain AQ178+TX, Bacillus subtilis strain AQ153+TX, Bacillus subtilis strain AQ743+TX, Bacillus subtilis strain QST 713 (CEASE®, Serenade®, Rhapsody®)+TX, Bacillus subtilis strain QST 714 (JAZZ®)+TX, Bacillus subtilis strain QST3002+TX, Bacillus subtilis strain QST3004+TX, Bacillus subtilis var. amyloriquefaciensamyloliquefaciens) strain FZB24 (Taegro®, Rhizopro®) + TX, Bacillus thuringiensis aizawai GC 91 (Agree®) + TX, Bacillus thuringiensis Cry 2Ae + TX, Bacillus thuringiensis Cry 1Ab + TX, Bacillus thuringiensis israelensis (BMP123®, Aquabac®, VectoBac®) + TX, Bacillus thuringiensis krustaki (Bacillus thuringiensis Bacillus thuringiensis kurstaki (Javelin®, Deliver®, CryMax®, Bondide®, Scutella WP®, Turilav WP®, Astuto®, Dipel WP®, Biobit®, Foray®) + TX, Bacillus thuringiensis kurstaki BMP 123 (Baritone®) + TX, Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF / 3P®) + TX, Bacillus thuringiensis strain AQ52 + TX, Bacillus thuringiensis Bacillus thuringiensis) strain BD#32+TX, Bacillus thuringiensis tenebrionis (Novodor®, BtBooster)+TX, Bacillus thuringiensis var. aizawai (XenTari®, DiPel®)+TX, species of the genus Bacteria (bacteria spp.))(GROWMEND(registered trademark), GROWSWEET(registered trademark), Shootup(registered trademark))+TX, Clavipacter michiganensis bacteriophage (AgriPhage(registered trademark), Bakflor(registered trademark))+TX, Beauveria bassiana (Beaugenic(registered trademark), Brocaril WP(registered trademark))+TX, Beauveria bassiana GHA (Mycotrol ES(registered trademark), Mycotrol O(registered trademark), BotaniGuard(registered trademark))+TX, Beauveria brongniartii (Engerlingspilz(registered trademark), Schweizer Beauveria(registered trademark), Melocont(registered trademark))+TX, Beauveria species (Beauveria spp.)+TX, Botrytis cineria cineria)+TX, soybean rhizobia (Bradyrhizobium japonicum) (TerraMax®)+TX, Brevibacillus brevis+TX, Burkholderia cepacia (Deny®, Intercept®, Blue Circle®)+TX, Burkholderia gladii+TX, Burkholderia gladioli+TX, Burkholderia spp.)+TX, Canadian thistle fungus (CBH Canadian Bioherbicide®)+TX, Candida butyri+TX, Candida famata+TX, Candida fructus+TX, Candida glabrata+TX, Candida guilliermondii+TX, Candida melibiosica+TX, Candida oleophila strain O+TX, Candida parapsilosis+TX, Candida pelliculosa+TX, Candida pulcherrima(Candida) Candida pulcherrima)+TX, Candida reukaufii+TX, Candida saitoana (Bio-Coat®, Biocure®)+TX, Candida sake+TX, Candida spp. species+TX, Candida tenius+TX, Cedecea davisae+TX, Cellulomonas flavigena+TX, Chaetomium cochliodes (Nova-Cide®)+TX, Chaetomium globosum (Nova-Cide®)+TX, Chromobacterium subtsugae (subtsugae) strain PRAA4-1T (Grandevo(registered trademark)) + TX, Cladosporium chlorocephalum + TX, Cladosporium cladosporioides + TX, Cladosporium oxysporum + TX, .Cladosporium spp. + TX, Cladosporium tenuissimum + TX, Clonostachys rosea (EndoFine®) + TX, Colletotrichum acutatum + TX, Coniothyrium minitans (Cotans WG®) + TX, Coniothyrium spp.)+TX, Cryptococcus albidus (YIELDPLUS(registered trademark))+TX, Cryptococcus humicola+TX, Cryptococcus infirmo-miniatus+TX, Cryptococcus laurentii+TX, Cryptophlebia leucotreta granulovirus (Cryptex(registered trademark))+TX, Cupriavidus campinensis+TX, Cydia pomonella granulovirus (CYD-X(registered trademark), Madex(registered trademark), Madex(registered trademark)Plus, Madex Max, Carpovirusine®) + TX, Cylindrobasidium laeve (Stumpout®) + TX, Cylindrocladium + TX, Debaryomyces hansenii + TX, Drechslera hawaiinensis + TX, Enterobacter cloacae + TX, Enterobacteriaceae + TX, Entomophtora virulenta (Vektor®) + TX, Epicoccum nigrum + TX, Epicoccum purpurascens + TX, Epicoccum spp.)+TX, Filobasidium floriforme+TX, Fusarium acuminatum+TX, Fusarium chlamydosporum+TX, Fusarium oxysporum (Fusaclean®, Biofox C®)+TX, Fusarium proliferatum+TX, Fusarium spp.+TX, Galactomyces geotrichum+TX, Gliocladium catenulatum (Primastop®, Prestop®)+TX, Gliocladium roseum roseum)+TX, Gliocladium spp. (SoilGard®)+TX, Gliocladium virens (Soilgard®)+TX, Granulovirus (Granupom®)+TX, Halobacillus halophilus+TX, Halobacillus litoralis+TX, Halobacillus trueperi+TX, Halomonas spp.)+TX, Halomonas subglaciescola+TX, Halovibrio variabilis+TX, Hanseniaspora uvarum+TX, Helicoverpa armigera nuclear polyhedra virus (Helicovex®)+TX, Helicoverpa zea nuclear polyhedra virus (Gemstar®)+TX, Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus, PFR-97®, PreFeRal®)+TX, isoflavone formononetin (Myconate®)+TX, Kloeckera apiculata apiculata)+TX, species of the genus Kloeckera (Kloeckera spp.))+TX, Lagenidium giganteum (Laginex®)+TX, Lecanicillium lecanii (formerly known as Verticillium lecanii (Mycotal®)) conidia of strain KV01 (e.g., Vertalec® by Koppert / Arysta)+TX, greenhouse whitefly (Lecanicillium longisporum) (Vertiblast®)+TX, Lecanicillium muscarium (Vertikil®)+TX, gypsy moth (Lymantria Dispar) nuclear polyhedron virus (Disparvirus®)+TX, Marinococcus halophilus+TX, Meira geuraconigii geulakonigii)+TX, Metarhizium anisopliae (Destruxin WP(registered trademark))+TX, Metarhizium anisopliae (Met52(registered trademark))+TX, Metschnikowia fruticola (Shemer(registered trademark))+TX, Metschnikowia pulcherrima+TX, Microdochium dimerum (Antibot(registered trademark))+TX, Micromonospora coerulea+TX, Microsphaeropsis ochracea+TX, Muscodor albus albus)620(Muscudor(registered trademark))+TX, Muscodor roseus, especially strain A3-5 (acceptance number NRRL 30548)+TX, species of the genus Mycorrhizae.)(AMykor(registered trademark), Root Maximizer(registered trademark))+TX, Mulberry dark spot disease fungus (Myrothecium verrucaria) strain AARC-0255 (DiTera(registered trademark), BROS PLUS(registered trademark))+TX, Ophiostoma piliferum strain D97 (Sylvanex(registered trademark))+TX, Paecilomyces farinosus+TX, Paecilomyces lilacinus strain 251 (MeloCon WG(registered trademark))+TX, Paecilomyces linacinus (Biostat WP(registered trademark))+TX, Paenibacillus polymyxa polymyxa)+TX, Pantoea agglomerans (BlightBan C9-1(registered trademark))+TX, Pantoea spp. species+TX, Pasteuria nishizawae, especially strain Pn1 (CLARIVA from Syngenta / ChemChina)+TX, Pasteuria spp. (Econem(registered trademark))+TX, Penicillium aurantiogriseum+TX, Penicillium billai (Jumpstart(registered trademark), TagTeam(registered trademark))+TX, Penicillium brevicompactum+TX, Penicillium phlequentans (Penicillium * Penicillium viridicatum + TX, Phlebiopsis gigantean (Rotstop®) + TX, Phosphollytic bacteria (Phosphomeal®) + TX, Phytophthora cryptogea + TX, Phytophthora palmivora (Devine®) + TX, Pichia anomala + TX, Pichia guilliermondii + TX, Pichia membranaefaciens + TX, Pichia onychis + TX, Pichia stipites + TX, Pseudomonas Pseudomonas aeruginosa) + TX, Pseudomonas aureofasciens (Spot-Less Biofungicide®) + TX, Pseudomonas cepacia + TX, Pseudomonas chlororaphis (AtEze®) + TX, Pseudomonas corrugate + TX, Pseudomonas fluorescens (Zequanox®) + TX, Pseudomonas fluorescens strain A506 (BlightBan A506®) + TX, Pseudomonas putida + TX, Pseudomonas reactance (Pseudomonas reactans)+TX, species of the genus Pseudomonas (Pseudomonas spp.))+TX, Pseudomonas syringae (Bio-Save®)+TX, Pseudomonas viridiflava+TX, Pseudozyma flocculosa strain PF-A22UL (Sporodex L®)+TX, Puccinia canaliculata+TX, Puccinia thlaspeos (Wood Warrior®)+TX, Pythium paroecandrum+TX, Pythium oligandrum (Polygandron®, Polyversum®)+TX, Pythium periprocum (Pythium periplocum)+TX, Rhanella aquatilis+TX, Rhanella spp. species+TX, Rhizobia (Dormal®, Vault®)+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 rubra)+TX, species of the genus Rhodotorula (Rhodotorula spp.))+TX, Saccharomyces cerevisiae+TX, Salinococcus roseus+TX, Sclerotinia minor (SARRITOR®)+TX, Sclerotinia minor+TX, Scytalidium spp.+TX, Scytalidium uredinicola+TX, Serratia marcescens+TX, Serratia plymuthica+TX, Serratia spp.)+TX, Sordaria fimicola+TX, Spodoptera exigua nuclear polyhedron virus (Spod-X®, Spexit®)+TX, Spodoptera littoralis nuclear polyhedron virus (Littovir®)+TX, Sporobolomyces roseus+TX, Stenotrophomonas maltophilia+TX, Streptomyces albaduncus+TX, Streptomyces exfoliates+TX, Streptomyces galbus+TX, Streptomyces glyceoplanus (Streptomyces griseoplanus)+TX, Streptomyces griseoviridis (Mycostop®)+TX, Streptomyces hygroscopicus+TX, Streptomyces lydicus (Actinovate®)+TX, Streptomyces lydicus WYEC-108 (ActinoGrow®)+TX, Streptomyces violaceus+TX, Tilletiopsis minor+TX, species of the genus Tilletiopsis (Tilletiopsis spp.)+TX, Trichoderma asperellum (T34 Biocontrol®)+TX, Trichoderma atroviride (Plantmte®)+TX, Trichoderma gamsii (Tenet®)+TX, Trichoderma hamatum TH 382+TX, Trichoderma harzianum rifai (Mycostar®)+TX, Trichoderma harzianum T-22 (Trianum-P®, PlantShield HC®, RootShield®, Trichoderma-G®)+TX, Trichoderma harzianum (Trichoderma harzianum)T-39(Trichodex(registered trademark))+TX, Trichoderma inhamatum+TX, Trichoderma koningii+TX, Trichoderma lignorum+TX, Trichoderma longibrachiatum+TX, Trichoderma polysporum(Binab T(registered trademark))+TX, Trichoderma species (Trichoderma spp.)LC52(Sentinel(registered trademark))+TX, Trichoderma taxi+TX, Trichoderma virens (formerly Gliocladium virens GL-21)(SoilGuard(registered trademark))+TX, Trichoderma virens+TX, Trichoderma viride+TX, Trichoderma viride strain ICC 080(Remedier(registered trademark))+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 (Botry-Zen®)+TX, Ustilago maydis+TX, various bacteria and auxiliary micronutrients (Natural II®)+TX, various fungi (Millennium Microbes®)+TX, Verticillium chlamydosporium Chlamydosporium)+TX, Vip3Aa20 (VIPtera(registered trademark))+TX, Virgibaclillus marismortui+TX, Xanthomonas campestris pv. Poae (Camperico(registered trademark))+TX, Xenorhabdfus bovienii+TX, Xenorhabdus nematophilus+TX;.AGNIQUE® MMF + TX, Azadirachtin (Plasma Neem Oil®, AzaGuard®, MeemAzal®, Molt-X®, e.g., AZATIN XL from Certis, USA) + TX, Botanical Insect Growth Regulators (Botanical IGRs) (Neemazad®, Neemix®) + TX, BugOil® + TX, Rapeseed Oil (Lilly Miller Vegol®) + TX, American Ant-Grain Grass (Chenopodium ambrosioides near ambrosioides) (Requiem®) + TX, Chrysanthemum Extract (Crisant®) + TX, Lamiaceae Essential Oil (Botania®) + TX, Neem Oil Extract (Trilogy®) + TX, Clove, Rosemary, Peppermint and Thyme Oil Extracts (Garden insect Killer® + TX, Garlic + TX, Glycine Betaine (Greenstim®) + TX, Kaolin (Screen®) + TX, Lemongrass Oil (GreenMatch®) + TX, Melaleuca alternifolia Extract (also known as Tea Tree Oil) (Timorex Gold®) + TX, Clove Peppermint Garlic Oil and Mint Mixture (Soil Shot®) + TX, Clove Rosemary and Peppermint Extract Mixture (EF 400®) + TX, Rosemary Sesame Peppermint Thyme and Cinnamon Extract Mixture (EF 300®) + TX, Neem Oil + TX, Catnip Oil (Nepeta cataria) + TX, Catnip Oil Cataria) + TX, Nicotine + TX, Oregano oil (MossBuster®) + TX, Pedaliaceae oil (Nematon®) + TX, Pine oil (Retenol®) + TX, Pyrethrum + TX, Soap tree (Quillaja saponaria) (NemaQ®) + TX, Japanese knotweed (Reynoutria)sachalinensis (Regalia®, Sakalia®) + TX, rotenone (Eco Roten®) + TX, Rutaceae plant extract (Soleo®) + TX, soybean oil (Ortho ecosense®) + TX, brown algae storage glucan (Laminarin®) + TX, thyme oil + TX; (E,Z)-7,9-Dodecadiene-1-yl acetate + TX, (E,Z,Z)-3,8,11-Tetradecatrienylate + TX, (Z,Z,E)-7,11,13-Hexadecatrienal + TX, 2-Methyl-1-butanol + TX, Biolure® + TX, Blackheaded Fireworm Pheromone (3M Sprayable Blackheaded Fireworm Pheromone®) + TX, Calcium Acetate + TX, Check-Mate® + TX, Codling Moth Pheromone (Paramount dispenser-(CM) / Isomate C-Plus®) + TX, Entostat Powder (Exosex CM®) (Exosex extract from palm trees) + TX, Grape Berry Moth Pheromone (3M MEC-GBM Sprayable Pheromone(registered trademark) + TX, Lavanzuryl senecioate + TX, Leafroller pheromone (3M MEC-LR Sprayable Pheromone(registered trademark)) + TX, Muscamone (Snip7 Fly Bait(registered trademark)) + TX, Oriental Fruit Moth pheromone (3M oriental fruit moth sprayable pheromone(registered trademark)) + TX, Peachtree Borer pheromone (Isomate-P(registered trademark)) + TX, Scenturion(registered trademark) + TX, Starbar Premium Fly Bait(registered trademark)) + TX, Tomato pinworm pheromone (3M Sprayable pheromone(registered trademark)) + TX; Acerophagus papaya + TX, Adalia bipunctata (Adalia-System®) + TX, Adalia bipunctata (Adaline®) + TX, Adalia bipunctata (Aphidalia®) + TX, Ageniaspis citricola + TX, Ageniaspis fuscicollis + TX, Amblyseius andersoni (Anderline®, Andersoni-System®) + TX, Amblyseius californicus (Amblyline®, Spical®) + TX, Amblyseius cucumeris cucumeris) (Thripex®, Bugline cucumeris®) + TX, Amblyseius fallacis (Fallacis®) + TX, Amblyseius swirskii (Bugline swirskii®, Swirskii-Mite®) + TX, Amblyseius womersleyi (WomerMite®) + TX, Amitus hesperidum + TX, Anagrus atomus + TX, Anagyrus fusciventris + TX, Anagyrus kamali + TX, Anagyrus roeckii (Anagyrus loecki)+TX, Anagyrus pseudococci (Citripar(registered trademark))+TX, Anicetus benefices+TX, Anisopteromaluscalandrae)+TX, Anthocoris nemoralis (Anthocoris-System(registered trademark))+TX, Aphelinus abdominalis (Apheline(registered trademark), Aphiline(registered trademark))+TX, Aphelinus asychis+TX, Aphidius colemani (Aphipar(registered trademark))+TX, Aphidius ervi (Aphelinus-System(registered trademark))+TX, Aphidius ervi (Ervipar(registered trademark))+TX, Aphidius gifuensis+TX, Aphidius matricariae (Aphidius matricariae)(Aphipar-M(registered trademark))+TX, Aphidoletes aphidimyza(Aphidend(registered trademark), Aphidoline(registered trademark))+TX, Aphytis lingnanensis+TX, Aphytis melinus+TX, Aprostocetus hagenowii+TX, Atheta coriaria(Staphyline(registered trademark))+TX, Bombus spp. species+TX, Bombus terrestris(Beeline(registered trademark), Tripol(registered trademark))+TX, Bombus terrestris(Natupol Beehive (registered trademark)) + TX, Cephalonomia stephanoderis + TX, Chilocorus nigritus + TX, Chrysoperla carnea (Chrysoline (registered trademark), Chrysopa (registered trademark)) + TX, Chrysoperla rufilabris + TX, Cirrospilus ingenuus + TX, Cirrospilus quadristriatus + TX, Citrostichus phyllocnistoides + TX, Closterocerus chamaeleon + TX, Closterocerus spp. species + TX, Coccidoxenoides perminutus (Planopar®) + TX, Coccophagus cowperi + TX, Coccophagus lycimnia + TX, Cotesia flavipes + TX, Cotesia plutellae)+TX, Cryptolaemus montrouzieri (Cryptobug®, Cryptoline®)+TX, Cybocephalus nipponicus+TX, Dacnusa sibirica (Minusa®, DacDigline®, Minex®)+TX, Delphastus catalinae (Delphastus®)+TX, Delphastus pusillus+TX, Diachasmimorpha krausii+TX, Diachasmimorpha longicaudata+TX, Diaparsis jukunda jucunda)+TX, Diaphorencyrtus aligarhensis+TX, Diglyphus isaea (Diminex®, Miglyphus®, Digline®)+TX, species of the genus Diversinervusspp.)+TX, Encarsia citrina+TX, Encarsia formosa (Encarsia max(registered trademark), Encarline(registered trademark), En-Strip(registered trademark))+TX, Encarsia guadeloupae+TX, Encarsia haitiensis+TX, Episyrphus balteatus (Syrphidend(registered trademark))+TX, Eretmoceris siphonini+TX, Eretmocerus californicus+TX, Eretmocerus eremicus (Enermix(registered trademark), Ercal(registered trademark), Eretline(registered trademark)) e(registered trademark), Bemimix(registered trademark))+TX, Eretmocerus hayati+TX, Eretmocerus mundus (Bemipar(registered trademark), Eretline m(registered trademark))+TX, Eretmocerus siphonini+TX, Exochomus quadripustulatus+TX, Feltiella acarisuga (Feltiline(registered trademark))+TX, Feltiella acarisuga (Spidend(registered trademark))+TX, Fopius arisanus+TX, Fopius ceratitivorus+TX, formononetin (Wireless Beehome(registered trademark))+TX, Franklinothrips vespiformis (Vespop(registered trademark))+TX, Galendromus occidentalis+TX, Goniozus legneri+TX, Habrobraconhebetor)+TX, Harmonia axyridis (HarmoBeetle®)+TX, Heterorhabditis bacteriophora (NemaShield HB®, Nemaseek®, Terranem-Nam®, Terranem®, Larvanem®, B-Green®, NemAttack®, Nematop®)+TX, Heterorhabditis megidis (Nemasys H®, BioNem H®, Exhibitline hm®, Larvanem-M®)+TX, Heterorhabditis spp. (LawnPatrol®)+TX, Hippodamia convergens) + TX, Hypoaspis aculeifer (Aculeifer-System®, Entomite-A®) + TX, Hypoaspis miles (Hypoline m®, Entomite-M®) + TX, Lbalia leucospoides + TX, Lecanoideus floccissimus + TX, Lemophagus errabundus + TX, Leptomastidea abnormis + TX, Leptomastix dactylopii (Leptopar®) + TX, Leptomastix epona epona)+TX, Lindorus lophanthae+TX, Lipolexis oregmae+TX, Lucilia caesar (Natufly(registered trademark))+TX, Lysiphlebus testacepestestaceipes)+TX, Macrolophus caliginosus (Mirical-N(registered trademark), Macroline c(registered trademark), Mirical(registered trademark))+TX, Mesoseiulus longipes+TX, Metaphycus flavus+TX, Metaphycus lounsburyi+TX, Micromus angulatus (Milacewing(registered trademark))+TX, Microterys flavus+TX, Muscidifurax raptorellus and Spalangia cameroni (Biopar(registered trademark))+TX, Neodryinus typhrosifei typhlocybae)+TX, Neoseiulus californicus+TX, Neoseiulus cucumeris (THRYPEX®)+TX, Neoseiulus fallacis+TX, Nesideocoris tenuis (NesidioBug®, Nesibug®)+TX, Ophyra aenescens (Biofly®)+TX, Orius insidiosus (Thripor-L®, Oriline i®)+TX, Orius laevigatus (Thripor-L®, Oriline i®)+TX, Orius majusukurus (Orius majusculus)(Oriline m(registered trademark))+TX, Orius strigicollis(Thripor-S(registered trademark))+TX, Pauesia juniperorum+TX, Pediobius hobeoletusfoveolatus)+TX, Phasmarhabditis hermaphrodita (Nemaslug®)+TX, Phymastichus coffea+TX, Phytoseiulus macropilus+TX, Phytoseiulus persimilis (Spidex®, Phytoline p®)+TX, Podisus maculiventris (Podisus®)+TX, Pseudacteon curvatus+TX, Pseudacteon obtusus+TX, Pseudacteon tricuspis+TX, Pseudaphycus maclipennis maculipennis)+TX, Pseudleptomastix mexicana+TX, Psyllaephagus pilosus+TX, Psyttalia concolor (complex)+TX, Quadrastichus spp. species+TX, Rhyzobius lophanthae+TX, Rodolia cardinalis+TX, Rumina decollate + TX, Semielacher petiolatus + TX, Sitobion avenae (Ervibank®) + TX, Steinernema carpocapsae (Nematac C®, Millenium®, BioNem C®, NemAttack®, Nemastar®, Capsanem®) + TX, Steinernema feltiae (NemaShield®, Nemasys F®, BioNem F®, Steinernema-System®, NemAttack®, Nemaplus®, Exhibitline) sf(registered trademark), Scia-rid(registered trademark), Entonem(registered trademark))+TX, Steinernema kraussei (Nemasys L(registered trademark), BioNem L(registered trademark), Exhibitline srb(registered trademark))+TX, Steinernema riobrave (BioVector(registered trademark), BioVektor(registered trademark))+TX, Steinernema scapterisci (Nematac S(registered trademark))+TX, species of the genus Steinernema (Steinernema spp.)+TX, species of the genus Steinernematid (Steinernematid spp.))(Guardian Nematodes(registered trademark))+TX, Stethorus punctillum(Stethorus(registered trademark))+TX, Tamarixia radiate+TX, Tetrastichus setifer+TX, Thripobius semiluteus+TX, Torymus sinensis+TX, Trichogramma brassicae(Tricholine b(registered trademark))+TX, Trichogramma brassicae(Tricho-Strip(registered trademark))+TX, Trichogramma evanescens+TX, Trichogramma minutum+TX, Trichogramma * ostriniae* + TX, * Trichogramma platneri* + TX, * Trichogramma pretiosum* + TX, * Xanthopimpla stemmator* + TX; Abscisic acid + TX, Aminomite® + TX, BioGain® + TX, bioSea® + TX, CAS number: 2643947-26-4 + TX, Chondrostereum purpureum (Chontrol Paste®) + TX, Colletotrichum gloeosporioides (Collego®) + TX, Copper octanoate (Cueva®) + TX, Delta Trap (Trapline d®) + TX, Erwinia amylovora (Harpin) (ProAct®), Ni-HIBIT Gold CST(registered trademark))+TX, fatty acids derived from natural by-products of extra virgin olive oil (FLIPPER(registered trademark))+TX, ferric phosphate (Ferramol(registered trademark))+TX, funnel trap (Trapline y(registered trademark))+TX, Gallex(registered trademark)+TX, Grower's Secret(registered trademark)+TX, homobrassonolide+TX, iron phosphate (Lilly Miller Worry Free Ferramol Slug & Snail Bait(registered trademark))+TX, MCP hail trap (Trapline f(registered trademark))+TX, Microctonus hyperodae+TX, Mycoleptodiscus terrestris (Des-X(registered trademark))+TX, Nosema locustae (Semaspore Organic Grasshopper Control(registered trademark))+TX, pheromone trap (Thripline ams(registered trademark)) + TX, potassium bicarbonate (MilStop(registered trademark)) + TX, potassium iodide + potassium thiocyanate (Enzicur(registered trademark)) + TX, potassium salt of fatty acid (Sanova(registered trademark)) + TX, potassium silicate solution (Sil-Matrix(registered trademark)) + TX, spider venom + TX, sticky trap (Trapline)YF(registered trademark), Rebell Amarillo(registered trademark))+TX, SuffOil-X(registered trademark)+TX, Trap(Takitrapline y+b(registered trademark))+TX; Bacillus mojavensis strain R3B (acceptance number NCAIM(P)B001389) (International Publication No. 2013 / 034938) + TX manufactured by Certis USA LLC, Bacillus pumilus strain BU F-33 (BASF's CARTISSA® registered trademark, EPA registration number 71840-19) + TX with NRRL acceptance number 50185, Bacillus subtilis CX-9060 manufactured by Certis USA LLC, Bacillus sp. strain D747 (available as DOUBLE NICKEL® manufactured by Kumiai Chemical Industry Co., Ltd.), acceptance number FERM U.S. Patent No. 7,094,592 + TX, containing BP-8234, Bacillus subtilis strain BU1814 (VELONDIS® PLUS, VELONDIS® FLEX and VELONDIS® EXTRA from BASF SE) + TX, Bacillus subtilis var. amyloliquefaciens strain FZB24 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5)) + TX, Bacillus subtilis, in particular strain QST713 / AQ713 (NRRL acceptance number B-21661, described in U.S. Patent No. 6,060,051, Bayer CropScience Paenibacillus polymyxa, particularly strain AC-1 (e.g., TOPSEED® from Green Biotech Company Ltd.) +TX, with acceptance number NRRL B-50972 or acceptance number NRRL B-67129 (Paenibacillus sp.)), International Publication No. 2016 / 154297+TX, Pantoea agglomerans, in particular strain E325 (acceptance number NRRL B-21856) (available as BLOOMTIME BIOLOGICAL® FD BIOPESTICIDE from Northwest Agri Products)+TX, Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena)+TX; Aureobasidium pullulans, in particular spores of strain DSM 14940, spores of strain DSM 14941, or a mixture of spores of strains DSM14940 and DSM14941 (e.g., BOTECTOR® and BLOSSOM PROTECT® from bio-ferm,CH) + TX, Pseudozyma aphidis (disclosed in International Publication No. 2011 / 151819 by Yissum Research Development Company of the Hebrew University of Jerusalem) + TX, Saccharomyces cerevisiae, in particular Lesaffre et al. Strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938 or CNCM No. 1-3939 from Compagnie, FR (International Publication No. 2010 / 086790) + TX; Agrobacterium radiobacter strain K84 (e.g., GALLTROL-A® from AgBioChem, CA) + TX, Bacillus amyloliquefaciens isolate B246 (e.g., AVOGREEN® from University of Pretoria) + TX, Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL acceptance number B-50768, International Publication No. 2014 / 028521) (STARGUS® from Marrone Bio Innovations) + TX, Bacillus amyloliquefaciens strain FZB42, acceptance number DSM 23117 (available as RHIZOVITAL® from ABiTEP, DE) + TX, Bacillus amyloliquefaciens, particularly strain D747 (available as Double Nickel® from Kumiai Chemical Industry Co., Ltd., with acceptance number FERM BP-8234, U.S. 7,094,Specification No. 592) + TX, Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (QUARTZO® (WG) and PRESENCE® (WP) manufactured by FMC Corporation) + TX, Bacillus licheniformis, in particular strain SB3086 with acceptance number ATCC55406, International Publication No. 2003 / 000051 (available from Novozymes as ECOGUARD® Biofungicide and GREEN RELEAF®) + TX, Bacillus methylotrophicus strain BAC-9912 (manufactured by the Chinese Academy of Sciences' Institute of Applied Ecology) + TX, Bacillus mycoides mycoides), isolate, acceptance number B-30890 (available from Certis USA LLC as BMJ TGAI® or WG and LifeGard®) + TX, Bacillus pumilus, in particular strain GB34 (available from Bayer AG, DE as Yield Shield®) + TX, Bacillus pumilus, in particular strain QST2808 (available from Bayer CropScience LP, US as SONATA®, acceptance number NRRL B-30087, US 6,245,(as described in Specification No. 551) +TX, Bacillus subtilis CX-9060 +TX from Certis USA LLC, Bacillus subtilis IAB / BS03 (AVIV (trademark) from STK Bio-Ag Technologies, PORTENTO (registered trademark) from Idai Nature) +TX, Bacillus subtilis KTSB strain (FOLIACTIVE (registered trademark) from Donaghys) +TX, Bacillus subtilis strain BU1814 (VELONDIS (registered trademark) PLUS, VELONDIS (registered trademark) FLEX and VELONDIS (registered trademark) EXTRA from BASF SE) +TX, Bacillus subtilis strain GB03 (available as Kodiak (registered trademark) from Bayer AG, DE) +TX, Bacillus subtilis Bacillus subtilis strain MBI 600 (available from BASF SE as SUBTILEX), acceptance number NRRL B-50595, U.S. Patent No. 5,061,495 + TX, Bacillus subtilis strain Y1336 (available from Bion-Tech, Taiwan as BIOBAC® WP, registered in Taiwan as a biological fungicide under registration numbers 4764, 5454, 5096 and 5277) + TX, Bacillus subtilis var. amyloliquefaciens strain FZB24 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5)) + TX, Bacillus subtilis subtilis)Y1336(Bion-Tech,Paenibacillus epiphyticus (International Publication No. 2016 / 020371) +TX from BASF SE, Paenibacillus polymyxa ssp. plantarum (International Publication No. 2016 / 020371) +TX from BASF SE, Paenibacillus sp. strains with acceptance number NRRL B-50972 or acceptance number NRRL B-67129, International Publication No. 2016 / 154297 +TX, Pseudomonas chlororaffis Pseudomonas chlororaphis strain AFS009, acceptance number NRRL B-50897, International Publication No. 2017 / 019448 (e.g., HOWLER® and ZIO® by AgBiome Innovations, US) + TX, Pseudomonas chlororaphis, in particular strain MA342 (e.g., CEDOMON®, CERALL®, and CEDRESS® by Bioagri and Koppert) + TX, Pseudomonas fluorescens strain A506 (e.g., BLIGHTBAN® A506 by NuFarm) + TX, Pseudomonas proradix (e.g., PRORADIX® by Sourcon Padena) + TX, Streptomyces glyceobilidis griseoviridis) strain K61 (also known as Streptomyces galbus strain K61) (acceptance number DSM 7206) (MYCOSTOP® by Verdera, PREFENCE® by BioWorks, Crop Protection 2006, 25)See pages 468-475) +TX, Streptomyces lydicus strain WYEC108 (also known as Streptomyces lydicus strain WYCD108US) (manufactured by Novozymes under ACTINO-IRON® and ACTINOVATE®) +TX; Trichoderma atroviride, strain T11 (IMI352941 / CECT20498) + TX; Ampelomyces quisqualis strain AQ10 (e.g., AQ10® by IntrachemBio Italia) + TX with acceptance number CNCM 1-807; Ampelomyces quisqualis, in particular strain AQ10 (e.g., AQ10® by IntrachemBio Italia) + TX; Aspergillus flavus strain NRRL 21882 (product known as AFLA-GUARD® by Syngenta / ChemChina) + TX; Aureobasidium pullulans, in particular strain DSM 14941 spores + TX, Aureobasidium pullulans, especially strain DSM14940 spores + TX, Aureobasidium pullulans, especially a mixture of spores of strains DSM14940 and DSM14941 (e.g., Botector® by bio-ferm, CH) + TX, Chaetomium cupreum (acceptance number CABI 353812) (e.g., BIOKUPRUM® by AgiLife) + TX, Chaetomium globosum (available as RIVADIOM® by Rivale) + TX, Cladosporium cladospolioides Coniothyrium minitans, particularly strain CON / M / 91-8 (acceptance number DSM9660, e.g., Bayer CropScience Biologics), has strain H39, acceptance number CBS122244, U.S. Patent Application Publication No. 2010 / 0291039 (by Stichting Dienst Landbouwkundig Onderzoek) + TX, Coniothyrium minitans, in particular strain CON / M / 91-8 (acceptance number DSM9660, e.g., Bayer CropScience Biologics).Contans(registered trademark) +TX from GmbH, Cryptococcus flavescens, strain 3C (NRRL Y-50378) +TX, Dactylaria candida, Dilophosphora alopecuri (available as TWIST FUNGUS(registered trademark)), Fusarium oxysporum, strain Fo47 (available as FUSACLEAN(registered trademark) from Natural Plant Protection) +TX, Gliocladium catenulatum (synonym: Clonostachys rosea f. catenulate) strain J1446 (e.g., Prestop(registered trademark) by Lallemand) +TX, Gliocladium roseum * Clonostachys rosea f 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', Australasian Plant Pathol. 2007, 36(2):95-101) + TX, *Gliocladium roseum (also known as *Clonostachys rosea f rosea*), particularly strain 321U from Adjuvants Plus, strain ACM941 disclosed in Xue AG (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root tot complex of field pea, Can Jour Plant Science)2003,83(3):519-524)+TX, Metschnikowia fructicola, especially strain NRRL Y-30752+TX, Microsphaeropsis ochracea, Penicillium steckii (DSM 27859, International Publication No. 2015 / 067800)+TX from BASF SE, Trichoderma asperellum strain ICC 012 (also known as Trichoderma harzianum ICC012) with acceptance number CABI CC IMI 392716, and Trichoderma gammii with acceptance number IMI 392151 A mixture of gamsii (formerly T. viride) strain ICC 080 (e.g., BIO-TAM® from Isagro USA, Inc. or BIODERMA® by Agrobiosol de Mexico, SA de CV) + TX, Penicillium vermiculatum + TX, Phlebiopsis gigantea strain VRA 1992 (ROTSTOP® C from Danstar Ferment) + TX, Pseudozyma flocculosa strain PF-A22 UL (available as SPORODEX® L from Plant Products Co., CA) + TX, Saccharomyces cerevisiae strain LAS117 cell wall (CEREVISANE® from Lesaffre, BASF) SE-made ROMEO(registered trademark))+TX, Saccharomyces cerevisiae strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938, CNCM No. 1-3939 (International Publication No. 2010 / 086790)+TX, Saccharomyces cerevisiae*Trichoderma cerevisiae*, especially strain LASO2 (from Agro-Levures et Derives) +TX, Simplicillium lanosoniveum +TX, strain T34 (e.g., T34 Biocontrol by Biocontrol Technologies SL,ES) 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 (acceptance number NRRL B-50759) (TRICHO PLUS® registered trademark from BASF SE) +TX, Trichoderma asperelum Trichoderma asperellum, in particular strain SKT-1, acceptance number FERM P-16510 (e.g., ECO-HOPE® from Kumiai Chemical Industry) + TX, Trichoderma asperellum, in particular strain kd (e.g., T-Gro from Andermatt Biocontrol) + TX, Trichoderma atroviride strain 77B (T77 from Andermatt Biocontrol) + TX, Trichoderma atroviride strain ATCC 20476 (IMI 206040) + TX, Trichoderma atroviride strain LC52 (e.g., Tenet from Agrimm Technologies Limited) + TX, Trichoderma atroviride strain LU132 (e.g., Agrimm Sentinel)+TX, Trichoderma atroviride strain NMI number V08 / 002388+TX, manufactured by Technologies Limited.Trichoderma atroviride strain NMI number V08 / 002389+TX, Trichoderma atroviride strain NMI number V08 / 002390+TX, Trichoderma atroviride strain number V08 / 002387+TX, Trichoderma atroviride strain SKT-1 (FERM P-16510), Japanese Patent Publication No. 11-253151+TX, Trichoderma atroviride strain SKT-2 (FERMP-16511), Japanese Patent Publication No. 11-253151+TX, Trichoderma atroviride Trichoderma atroviride) strain SKT-3 (FERMP-17021), Japanese Patent Publication No. 11-253151 + TX, Trichoderma atroviride, especially strain SC1 (acceptance number CBS 122089, International Publication No. 2009 / 116106 and U.S. Patent No. 8,431,120 (from Bi-PA)) + TX, Trichoderma atroviride strain CNCM 1-1237 (e.g., Esquive® WP from Agrauxine, FR) + TX, Trichoderma fertile (e.g., BASF product TrichoPlus) + TX, Trichoderma gumsii (Trichoderma Trichoderma gamsii (formerly T. viride) + TX, Trichoderma gamsii (formerly T. viride) strain ICC 080 (IMI CC 392151 CABI) (available as BIODERMA® by AGROBIOSOL DE MEXICO, SADE CV) + TX, Trichoderma gamsii strain ICC080 (IMI CC 392151 CABI, e.g., BioDerma by AGROBIOSOL DE MEXICO, SADE CV) + TX, Trichoderma harmatum + TX, Trichoderma harmatum + TX with acceptance number ATCC 28012, Trichoderma harzianum + TX, Trichoderma harzianum rifai T39 (e.g., Trichodex® from Makhteshim, US) + TX, Trichoderma harzianum strain Cepa SimbT5 (Simbiose (from Agro) +TX, Trichoderma harzianum strain DB 103 (available as T-GRO® 7456 from Dagutat Biolab) +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 by Mycontrol) +TX, Trichoderma polysporum strain IMI 206039 (e.g., Binab TF by BINAB Bio-Innovation AB, Sweden) Trichoderma stromaticum (e.g., CEPLAC) with acceptance number Ts3550, WP)+TXTrichoderma virens (also known as Gliocladium virens), particularly strain GL-21 (e.g., SoilGard by Certis, US), Trichoderma virens strain G-41 (formerly known as Gliocladium virens) (acceptance number ATCC 20906) (e.g., ROOTSHIELD® PLUS WP and TURFSHIELD® PLUS WP from BioWorks, US), Trichoderma viride, particularly strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie). 161:125-137)+TX, Trichoderma viride strain TV1 (e.g., Trianum-P by Koppert)+TX, Ulocladium oudemansii strain U3 with acceptance number NM 99 / 06216 (e.g., BOTRY-ZEN® by Botry-Zen Ltd, New Zealand and BOTRYSTOP® from BioWorks, Inc.)+TX, Verticillium albo-atrum (formerly V. dahliae), strain WCS850 with acceptance number WCS850 deposited at the Central Bureau for Fungi Cultures (e.g., DUTCH TRIG® by Tree Care Innovations)+TX, Verticillium chlamidosporium chlamydosporium)+TX;, A mixture of Azotobacter vinelandii and Clostridium pasteurianum (available as INVIGORATE® from Agrinos) + TX, a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available as QUARTZO® (WG) and PRESENCE® (WP) from FMC Corporation) + TX, Azorhizobium caulinodans, especially strain ZB-SK-5 + TX, Azospirillum brasilense (e.g., VIGOR® from KALO, Inc.) + TX, Azospirillum lipoferum Bacillus lipoferum (e.g., VERTEX-IF™ manufactured by TerraMax, Inc.) + TX, Azotobacter chroococcum, especially strain H23 + TX, Azotobacter vinelandii, especially strain ATCC 12837 + TX, Bacillus amyloliquefaciens BS27 (acceptance number NRRL B-5015) + TX, Bacillus amyloliquefaciens, especially strain FZB42 (e.g., RHIZOVITAL™ manufactured by ABiTEP, DE) + TX, Bacillus amyloliquefaciens Bacillus amyloliquefaciens), especially strain IN937a+TX, Bacillus amyloliquefaciens pm414 (LOLI-PEPTA® manufactured by Biofilm Crop Protection)+TX, Bacillus amyloliquefaciensBacillus amyloliquefaciens)SB3281 (ATCC#PTA-7542, International Publication No. 2017 / 205258) + TX, Bacillus amyloliquefaciens TJ1000 (available from Novozymes as QUIKROOTS®) + TX, Bacillus cereus member EE128 (NRRL number B-50917) + TX, Bacillus cereus member EE349 (NRRL number B-50928) + TX, Bacillus cereus, especially strain BP01 (ATCC 55675, e.g., MEPICHLOR® from Arysta Lifescience, US) + TX, Bacillus mycoides Bacillus mycoides BT155 (NRRL number B-50921) + TX, Bacillus mycoides BT46-3 (NRRL number B-50922) + TX, Bacillus mycoides EE118 (NRRL number B-50918) + TX, Bacillus mycoides EE141 (NRRL number B-50916) + TX, Bacillus pumilus, especially strain GB34 (e.g., YIELD SHIELD (registered trademark) from Bayer Crop Science, DE) + TX, Bacillus pumilus, especially strain QST2808 (acceptance number NRRL number B-30087) + TX, Bacillus siamensis Bacillus subtilis, particularly strain KCTC 13613T+TX, Bacillus subtilis, particularly strain AQ30002 (acceptance number NRRL, acceptance number B-50421 and U.S. Patent Application Publication No. 13 / 330,576)+TX, Bacillus subtilis, particularly strain AQ30004 (acceptance number NRRL, acceptance number B-50455 and U.S. Patent Application Publication No. 13 / 330,576)+TX, Bacillus subtilisBacillus subtilis, especially strain MBI 600 (e.g., SUBTILEX® from BASF SE) + TX, Bacillus subtilis rm303 (RHIZOMAX® from Biofilm Crop Protection) + TX, Bacillus subtilis strain BU1814 (available from BASF SE as TEQUALIS®) + TX, Bacillus tequilensis, especially strain NII-0943 + TX, Bacillus thuringiensis BT013A (NRRL number B-50924), also known as Bacillus thuringiensis 4Q7 + TX, soybean rhizobia (Bradyrhizobium) japonicum (e.g., Novozymes' OPTIMIZE®) + TX, Delftia acidovorans, especially strain RAY209 (e.g., Brett Young Seeds' BIOBOOST®) + TX, Lactobacillus sp. (e.g., LACTOPLANT® from LactoPAFI) + TX, Mesorhizobium cicer (e.g., NODULATOR from BASF SE) + TX, Paenibacillus polymyxa, especially strain AC-1 (e.g., TOPSEED® from Green Biotech Company Ltd.) + TX, Pseudomonas aeruginosa, especially strain PN1 + TX, Pseudomonas proradix (e.g., Sourcon PRORADIX® (registered trademark) + TX from Padena, Hairy vetch rhizobia (Rhizobium leguminosarium biovar viciae) (e.g., NODULATOR from BASF SE) + TX, Rhizobium leguminosariumLeguminosarum), especially strain bv. viceae Z25 (acceptance number CECT 4585) + TX; Serratia marcescens, especially strain SRM (acceptance number MTCC 8708) + TX; Alfalfa rhizobia (Sinorhizobium meliloti) strain NRG-185-1 (NITRAGIN® GOLD from Bayer CropScience) + TX; Thiobacillus sp. (e.g., CROPAID® from Cropaid Ltd UK) + TX; Myrothecium verrucaria strain AARC-0255 (e.g., DiTera® from Valent Biosciences) + TX, Penicillium bilaii strain ATCC 22348 (e.g., JumpStart® from Acceleron BioAg) + TX, Penicillium bilaii strain ATCC ATCC20851 + TX, Purpureocillium lilacinum (formerly known as Paecilomyces lilacinus) strain 251 (AGAL 89 / 030550, e.g., BioAct from Bayer CropScience Biologics GmbH) + TX, Pythium oliligandrum Pythium oligandrum strain DV74+TX, Pythium oligandrum strain M1 (ATCC 38472, e.g., Polyversum from Bioprepraty, CZ)+TX, Rhizopogon amylopogon (Myco-Sol from Agri-Enterprise, LLC (formerly Helena Chemical Company))+TX, Rhizopogon fulvigleba (Myco-Sol from Agri-Enterprise, LLC (formerly Helena Chemical Company))+TX, Talaromyces flavus strain V117b+TX, Trichoderma asperellum strain (Plant Health Products,Eco-T)+TX from ZA, Trichoderma asperellum strain kd (e.g., T-Gro from Andermatt Biocontrol)+TX, Trichoderma atroviride, particularly strain number V08 / 002387+TX, Trichoderma atroviride strain CNCM 1-1237 (e.g., Esquive® WP from Agrauxine, FR)+TX, Trichoderma atroviride strain LC52 (also known as Trichoderma atroviride strain LU132, e.g., Sentinel from Agrimm Technologies Limited)+TX, Trichoderma atroviride Trichoderma atroviride strain number NMI number V08 / 002388+TX, Trichoderma atroviride strain number NMI number V08 / 002389+TX, Trichoderma atroviride strain number NMI number V08 / 002390+TX, Trichoderma atroviride strain SC1 (described in International Publication No. 2009 / 116106)+TX, Trichoderma harzianum strain 1295-22+TX, Trichoderma harzianum strain ITEM 908+TX, Trichoderma harzianum strain T-22 (e.g., Andermatt Biocontrol or Koppert's Trianum-P)+TX, Trichoderma harzianum strain TSTh20+TX, Trichoderma virens strain GI-3+TX, Trichoderma virens strain GL-21 (e.g., Certis,SoilGard® (USA-made) +TX, Trichoderma viride strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161:125-137) +TX, Verticillium albo-atrum (formerly V. dahliae) strain WCS850 (CBS 276.92, e.g., Dutch Trig from Tree Care Innovations) +TX; Agrobacterium radiobacter strain K84 (Galltrol from AgBiochem Inc.) + TX, Bacillus amyloliquefaciens, especially strain PTS-4838 (e.g., AVEO from Valent Biosciences, US) + TX, Bacillus mycoides, isolate J. (e.g., BmJ from Certis USA LLC) + TX, Bacillus sphaericus, especially Serotype H5a5b strain 2362 (strain ABTS-1743) (e.g., VECTOLEX® from Valent BioSciences, US) + TX, Bacillus thuringiensis israelensis strain BMP 144 (e.g., Becker Microbial Products IL's AQUABAC(registered trademark)+TX, Bacillus thuringiensis subsp. aizawai strain GC-91+TX, Bacillus thuringiensis subsp. aizawai, especially serotype H-7 (e.g., FLORBAC(registered trademark) WG from Valent BioSciences, US)+TX, Bacillus thuringiensis subsp. aizawai, especially strain ABTS-1857 (SD-1372, e.g., XENTARI(registered trademark) from Valent BioSciences)+TX, Bacillus thuringiensis subsp. israelensis (serotype H-14) strain AM65-52 (acceptance number ATCC) 1276) (e.g., VECTOBAC® by Valent BioSciences, US) + TX, Bacillus thuringiensis subsp. crustachyBacillus thuringiensis subsp. kurstaki strain ABTS 351 + TX, Bacillus thuringiensis subsp. kurstaki strain BMP 123 (BARITONE, manufactured by Becker Microbial Products, IL and Bayer CropScience) + TX, Bacillus thuringiensis subsp. kurstaki strain EG 2348 (LEPINOX, manufactured by Certis, US) + TX, Bacillus thuringiensis subsp. kurstaki strain EG 7841 (CRYMAX®, manufactured by Certis, US) + TX, Bacillus thuringiensis subsp. kurstaki strain HD-1 (e.g., Valent BioSciences, US-made DIPEL(registered trademark) ES) + TX, Bacillus thuringiensis subsp. kurstaki strain PB 54 + TX, Bacillus thuringiensis subsp. kurstaki strain SA 11 (Certis, US-made JAVELIN) + TX, Bacillus thuringiensis subsp. kurstaki strain SA 12 (Certis, US-made THURICIDE) + TX, Bacillus thuringiensis subsp. tenebrionis strain NB 176 (SD-5428, e.g., BioFa DE-made NOVODOR(registered trademark) FC) + TX, Bacillus thuringiensis variety Colmeli (Bacillus Bacillus thuringiensis var. Colmeri) (e.g., TIANBAOBTC by Changzhou Jianghai Chemical Factory) + TX, Bacillus thuringiensis var. japonensisBacillus thuringiensis var. kurstaki strain EVB-113-19 (e.g., BIOPROTEC® from AEF Global) +TX, Brevibacillus laterosporus +TX, Burkholderia spp. species, especially Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis strain MBI 305) (acceptance number NRRL B-50319, international publications 2011 / 106491 and 2013 / 032693, e.g., MBI206 from Marrone Bio Innovations) TGAI and ZELTO (registered trademarks) + TX, Chromobacterium subtsugae, especially strain PRAA4-1T (e.g., MBI-203, e.g., GRANDEVO (registered trademark) from Marrone Bio Innovations) + TX, Lecanicillium muscarium Ve6 (MYCOTAL from Koppert) + TX, Paenibacillus popilliae (formerly Bacillus popilliae, e.g., St.MILKY SPORE POWDER (trademark) or MILKY SPORE GRANULAR (trademark) manufactured by Gabriel Laboratories + TX; Serratia entomophila (e.g., INVADE (registered trademark) by Wrightson Seeds) + TX; Serratia marcescens, especially strain SRM (acceptance number MTCC 8708) + TX; Trichoderma asperellum (TRICHODERMAX manufactured by Novozymes) + TX; Wolbachia pipientis ZAP strain (e.g., ZAP MALES (registered trademark) manufactured by MosquitoMate) + TX; Beauveria bassiana strain ATCC 74040 (e.g., NATURALIS® from Intrachem Bio Italia) + TX, Beauveria bassiana strain ATP02 (acceptance number DSM 24665), strain Apopka 97 (PREFERAL® from SePRO) + TX, Beauveria bassiana strain GHA (acceptance number ATCC74250, e.g., BOTANIGUARD® ES and MYCONTROL-O® from Laverlam International Corporation) + TX, Metarhizium anisopliae 3213-1 (deposited under NRRL acceptance number 67074, disclosed in International Publication No. 2017 / 066094, Pioneer Hi-Bred International) +TX, Metarhizium robertsii 15013-1 (deposited under NRRL receipt number 67073) +TX, Metarhizium robertsii 23013-3 (deposited under NRRL receipt number 67075) +TX, Paecilomyces lilacinus strain 251 (MELOCON® registered trademark from Certis, US) +TX; Cydia pomonella (codlinga) granulovirus (GV) + TX, Helicoverpa armigera (tobacco budworm) nuclear polyhedra disease virus (NPV) + TX, Adoxophyes orana (apple leafroller) granulovirus (GV) + TX, Spodoptera exigua (white fall armyworm) mNPV + TX, Spodoptera frugiperda (white fall armyworm) mNPV + TX; Species of the genus Burkholderia (Burkholderia spp.), especially Burkholderia cepacia (formerly known as Pseudomonas cepacia) + TX, species of the genus Gigaspora + TX, species of the genus Glomus + TX, species of the genus Laccaria + TX, Lactobacillus buchneri + TX, species of the genus Paraglomus + TX, Pisolithus tinctorus + TX, species of the genus Pseudomonas + TX, species of the genus Rhizobium, especially clover rhizobia (Rhizobium) trifolii)+TX, Rhizopogon spp.+TX, Scleroderma spp.+TX, Streptomyces spp.+TX, Suillus spp.+TX, Agrobacterium spp.+TX, Azorhizobium caulinodans+TX, Azospirillum spp.+TX, Azotobacter spp.+TX, Bradyrhizobium spp.+TX, Gigaspora monosporum+TX; Garlic (Allium sativum) (NEMGUARD by Eco-Spray, BRALIC by ADAMA) + TX, Armour-Zen + TX, Wormwood (Artemisia absinthium) + TX, Biokeeper WP + TX, Brassicaceae extract, especially rapeseed powder or mustard powder + TX, Cassia nigricans + TX, Celastrus angulatus + TX, American anthelminticum (Chenopodium anthelminticum) + TX, Quinoa (Chenopodium quinoa) saponin extract from quinoa seeds (e.g., Heads Up plant Protectants,CA-made Head Up (Saponins of Quinoa) + TX, Chitin + TX, Dryopteris filix-mas + TX, Equisetum arvense + TX, Fortune Aza + TX, Fungastop + TX, Melaleuca alternifolia extract (STK-made TIMOREX GOLD) + TX, Natural Blad polypeptide extracted from lupine seeds (FMC-made FRACTURE) + TX, Natural Blad polypeptide extracted from lupine seeds (Certis EU-made PROBLAD) + TX, Pyrethrins + TX, Quassia amara + TX, Quercus + TX, Quillaja extract (BASF-made QL AGRI 35) + TX, Marrone Bio-made REGALIA MAXX+TX, Requiem® Insecticide+TX, Japanese knotweed (Reynoutria sachalinensis) extract (REGALLIA)+TX, ryania / ryanodine+TX, Symphytum officinale+TX, Tansy (Tanacetum vulgare)+TX, Thymol+TX, Thymol mixed with geraniol (CEDROZ, Eden Research)+TX, Thymol mixed with geraniol and eugenol (MEVALONE, Eden Research)+TX, Triact 70+TX, TriCon+TX, Nasturtium (Tropaeulum majus)+TX, Urtica dioica+TX, Veratrine+TX, Viscum album+TX; Mercuric oxide + TX, octylinone + TX, thiophanate-methyl + TX; MGK 264 + TX, 2-(2-butoxyethoxy)ethyl piperonylate + TX, 2-isovalerylindan-1,3-dione + TX, 4-(quinoxaline-2-ylamino)benzenesulfonamide + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohexa-2-enone + TX, acibenzolar + TX, acibenzolar-S-methyl + TX, alpha-bromadiolone + TX, alpha-chlorohydrin + TX, aluminum phosphide + TX, anthraquinone + TX, anthu + TX, arsenic trioxide + TX, barium carbonate + TX X, Benoxacol + TX, Bisthiosemi + TX, Brodifacum + TX, Bromadiolon + TX, Bromethalin + TX, Calcium cyanide + TX, Chloralose + TX, Chlorophacinone + TX, Cholecalciferol + TX, Croquintocet (including Croquintocet-Mexyl) + TX, Copper naphthenate + TX, Copper oxychloride + TX, Coumacrol + TX, Coumafuryl + TX, Coumatetralyl + TX, Crimidine + TX, Cyprosulfamide + TX, Diazinon + TX, Dichlormid + TX, Dicyclopentadiene + TX, Diphenacum + TX, Difethiaron + TX, Difacinone + TX, Ergocalciferol + TX, Farnesol + TX, Farnesol and Nerolidol + TX, Fenchlorazole (including fenchlorazole-ethyl) + TX, Fenchlorim + TX, Furocumafen + TX, Fluoroacetamide + TX, Flupropazine + TX, Flupropazine hydrochloride + TX, Fluxofenim + TX, Frillazole + TX, Gamma-HCH + TX, Guazatine + TX, Guazatine acetate + TX, HCH + TX, Hydrogen cyanide + TX, Imanine + TX, Iodomethane + TX, Isoxadifen (containing isoxadifen-ethyl) + TX, Lindane + TX, Magnesium phosphide + TX, MB-599 + TX, Mefenyphen (containing mefenyphen-diethyl) + TX, Metocamifen + TX, Methiocarb + TX, Methyl bromide + TX, Nerolidol + TX, Norbolmid + TX, Petroleum + TX, Fosacetim + TX, Phosphine + TX, Phosphate + TX, Pincdon + TX, Piperonyl butoxide + TX, Piprotal + TX, Potassium arsenite + TX, Probenazole + TX, Propyl isomer + TX, Pyridine-4-amine + TX,Pyrinulone + TX, Japanese knotweed (Reynoutria sachalinensis) extract + TX, Ribavirin + TX, S421 + TX, Ciriloside + TX, Sesamex + TX, Sesasmorin + TX, Sodium arsenite + TX, Sodium cyanide + TX, Sodium fluoroacetate + TX, Strychnine + TX, Sulfoxide + TX, Thallium sulfate + TX, Thyram + TX, Trimetacarb + TX, Warfarin + TX, Zinc naphthenate + TX, Zinc phosphide + TX, Ziram + TX.

[0313] In addition, the compositions of the present invention may be applied together with one or more systemic acquired resistance inducers ("SAR" inducers). SAR inducers are known, for example, as described in U.S. Patent No. 6,919,298, and include, for example, salicylates and the commercially available SAR inducer acibenzolar-S-methyl.

[0314] The compounds of formula (I) as defined in the present invention are typically used in the form of compositions and can be applied to a planted area or a plant to be treated, simultaneously or sequentially, to further compounds. These further compounds may be, for example, fertilizers or sources of trace elements or other preparations that affect plant growth. They may also be selective or non-selective herbicides, as well as insecticides, fungicides, bactericidal agents, nematicides, molluscicides, or mixtures of these preparations, together with further carriers, surfactants, or application-enhancing adjuvants as commonly used in the art of formulation, as needed.

[0315] The compounds of formula (I) as defined in the present invention can be used in the form of a (fungicidal) composition for the control or protection of plant pathogenic microorganisms, comprising, as an active ingredient, at least one compound of formula (I) as defined in the present invention or at least one preferred individual compound defined in free form or in agrochemically usable salt form, and at least one of the above-mentioned auxiliary agents.

[0316] Accordingly, the present invention provides a composition, preferably a fungicidal composition, comprising at least one compound of formula (I) as defined in the present invention, an agriculturally acceptable carrier, and optionally an auxiliary agent. The agriculturally acceptable carrier is, for example, a carrier suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, in addition to the compound of formula (I) as defined in the present invention, the composition may contain at least one or more toxic biological compounds, such as additional fungicidal active ingredients.

[0317] Further aspects of the present invention relate to methods for controlling or preventing ectoparasitism by potentially harmful plant pathogenic or putrefactive microorganisms or organisms, particularly fungi, of plants, such as useful plants, such as crop plants, their reproductive materials, such as seeds, harvested crops, such as harvested food crops, or non-biological materials, the methods comprising the application of compounds of formula (I) as defined in the present invention, or preferred individual compounds as defined above as active ingredients for plants, to plants, to parts of plants or their habitats, to their reproductive materials, or to any part of non-biological materials.

[0318] Control or prevention means reducing ectopic parasites by insects, plant pathogenic or putrefactive microorganisms, or organisms potentially harmful to humans, particularly fungi, to a level where improvement is demonstrated.

[0319] A preferred method for controlling or preventing ectoparasitism of crop plants by plant pathogenic microorganisms, particularly fungi, including the application of a compound of formula (I) as defined in the present invention, or a pesticide composition containing at least one of the said compounds, is foliar application. The frequency and amount of application will depend on the risk of ectoparasitism by the corresponding pathogen or insect. However, a compound of formula (I) as defined in the present invention can also be introduced into plants through the soil via the roots (osmotic action) by drenching the plant habitat with a liquid formulation or by applying the compound in solid form, such as granular form, to the soil (soil application). In rice crops, such granular material can be applied to flooded paddy fields. A compound of formula (I) as defined in the present invention can also be applied to seeds (coating) by either impregnating the seeds or tubers with a liquid formulation of the fungicide or coating them with a solid formulation.

[0320] A composition containing a compound of formula (I) as defined in the present invention, and optionally a solid or liquid additive or a monomer for encapsulating the compound of formula (I) as defined in the present invention, can be prepared by known methods, typically by closely mixing and / or grinding the compound with an extender, such as a solvent, a solid carrier, and optionally a surface-active compound (surfactant).

[0321] Another subject of the present invention is the use of the composition for methods of controlling the above-mentioned types of pathogens, i.e., methods of application for the composition, i.e., spraying, misting, dusting, brushing, coating, diffusion, or pouring (these should be selected according to the intended purpose of the general situation). Typical concentration ratios are 0.1 to 1000 ppm, preferably 0.1 to 500 ppm of the active ingredient. The application rate per hectare is preferably 1 g to 2000 g of the active ingredient per hectare, more preferably 10 to 1000 g / ha, and most preferably 10 to 600 g / ha. When used as a seed drenching agent, a convenient dosage is 10 mg to 1 g of the active substance per 1 kg of seeds.

[0322] When the combination of the present invention is used for seed treatment, it is generally sufficient to use a ratio of the compound of formula (I) of 0.001 to 50 g per kg of seed, preferably 0.01 to 10 g per kg of seed.

[0323] Preferably, a composition comprising a compound of formula (I) according to the present invention as defined herein is applied either preventively (meaning before the onset of disease) or therapeutically (meaning after the onset of disease).

[0324] The compositions of the present invention may be any of the conventional forms, for example, two-component systems, dry seed treatment powder (DS), seed treatment emulsion (ES), seed treatment fluid concentrate (FS), seed treatment solution (LS), seed treatment water-dispersible powder (WS), seed treatment capsule suspension (CF), seed treatment gel (GF), emulsion concentrate (EC), suspension concentrate (SC), suspension emulsion (SE), capsule suspension (CS), water-dispersible granules (WG), emulsifying granules It can be employed in the form of granules (EG), water-in-oil (EO) emulsions, oil-in-water (EW) emulsions, microemulsions (ME), oil dispersions (OD), oil-miscible flowables (OF), oil-miscible liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), industrial concentrates (TK), dispersible concentrates (DC), wettable powders (WP), or any technically feasible formulation combined with agriculturally acceptable adjuvants.

[0325] Such compositions can be produced by conventional methods, for example, by mixing an active ingredient with a suitable formulation deactivator (diluent, solvent, filler, and optionally other formulation components such as surfactants, biocides, antifreezes, spreading agents, thickeners, and compounds that provide auxiliary effects). Conventional sustained-release formulations can also be used when sustained effectiveness over a long period is desired. In particular, formulations applied in spray form, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules, may contain surfactants, such as wetting agents and dispersants, and other compounds that provide auxiliary effects, such as formaldehyde, and condensation products of naphthalene sulfonates, alkylaryl sulfonates, lignin sulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0326] The seed coating formulation is applied to seeds in a manner known to the present invention, utilizing the combination and diluent of the present invention in a preferred seed coating formulation form, such as an aqueous suspension or a dry powder form having good adhesion to seeds. Such seed coating formulations are known in the art. The seed coating formulation may contain a single active ingredient or a combination of active ingredients in encapsulated form, such as slow-release capsules or microcapsules.

[0327] Generally, a formulation comprises 0.01 to 90% by weight of an active agent, 0 to 20% of an agrochemically acceptable surfactant, and 10 to 99.99% of a solid or liquid inert formulation and auxiliary agents, wherein the active agent consists of at least a compound of formula (I) as defined in this invention, together with components (B) and (C), and optionally other active agents such as particularly microbial agents or preservatives. The concentrated form of the composition generally contains about 2 to 80%, preferably about 5 to 70% by weight of the activator. The application form of the formulation may contain, for example, 0.01 to 20% by weight, preferably 0.01 to 5% by weight of the activator. Commercial products are preferably formulated as concentrates, but end users will typically use diluted formulations.

[0328] While it is preferable to incorporate commercially available products as concentrates, end users typically utilize dilute formulations. [Examples]

[0329] The following examples illustrate the present invention. Certain compounds of the present invention can be distinguished from known compounds by their greater potency at lower doses, which can be verified by those skilled in the art using the experimental procedures outlined in the examples.

[0330] Combination example

[0331] [Table 2]

[0332] By thoroughly mixing the active ingredient with an auxiliary agent and thoroughly grinding the mixture in a suitable pulverizer, a wettable powder can be obtained that can be diluted with water to form a suspension of the desired concentration.

[0333] [Table 3]

[0334] The active ingredient is thoroughly mixed with the auxiliary agent, and the mixture is thoroughly ground in a suitable mill to yield a powder that can be used directly for seed treatment.

[0335] emulsifiable concentrate Active ingredient [compound of formula (I)] 10% Octylphenol polyethylene glycol ether 3% (4-5 mol of ethylene oxide) Calcium dodecylbenzenesulfonate 3% Castor oil polyglycol ether (ethylene oxide 35 mol) 4% Cyclohexanone 30% Xylene mixture 50%

[0336] Emulsions of any required dilution suitable for plant protection can be obtained from this concentrate by dilution with water.

[0337] [Table 4]

[0338] Ready-to-use powders are obtained by mixing the active ingredient with a carrier and grinding the mixture in a suitable mill. Such powders can also be used for drying and coating seeds.

[0339] Extruded granules Active ingredient [compound of formula (I)] 15% Sodium lignin sulfonate 2% Carboxymethylcellulose 1% Kaolin 82%

[0340] The active ingredient is mixed with an auxiliary agent and ground, and the mixture is moistened with water. The mixture is then extruded and dried in an airflow.

[0341] Coated granules Active ingredient [compound of formula (I)] 8% Polyethylene glycol (molecular weight 200) 3% Kaolin 89%

[0342] The finely ground active ingredient is uniformly applied to kaolin moistened with polyethylene glycol in a mixer. A non-dusting coated granule is thus obtained.

[0343] Suspension concentrate Active ingredient [compound of formula (I)] 40% Propylene glycol 10% Nonylphenol polyethylene glycol ether (ethylene oxide 15 mol) 6% Sodium lignin sulfonate 10% Carboxymethylcellulose 1% Silicone oil (in the form of a 75% emulsion in water) 1% water 32%

[0344] The finely ground active ingredient is tightly mixed with an auxiliary agent to obtain a suspension concentrate. By diluting this with water, a suspension of the desired dilution can be obtained. Using such dilutions, not only growing plants but also plant propagation materials can be treated by spraying, pouring, or immersion to protect them from microbial ectoparasitism.

[0345] Flowable formulation for seed treatment Active ingredient [compound of formula (I)] 40% Propylene glycol 5% Copolymer Butanol PO / EO 2% Tristyrenephenol 2% with 10-20 moles of EO 1,2-Benzisothiazolin-3-one (20% aqueous solution) 0.5% Monoazo pigment calcium salt 5% Silicone oil (in the form of a 75% emulsion in water) 0.2% Water 45.3%

[0346] The finely ground active ingredient is tightly mixed with an auxiliary agent to obtain a suspension concentrate. By diluting this with water, a suspension of the desired dilution can be obtained. Using such dilutions, not only growing plants but also plant propagation materials can be treated by spraying, pouring, or immersion to protect them from microbial ectoparasitism.

[0347] Sustained-release capsule suspension Mix 28 parts of the compound combination of formula (I) with 2 parts of aromatic solvent and 7 parts of a toluene diisocyanate / polymethylene-polyphenyl isocyanate mixture (8:1). Emulsify this mixture in a mixture of 1.2 parts polyvinyl alcohol, 0.05 parts defoamer, and 51.6 parts water until the desired particle size is reached. Add a mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts water to this emulsion. Stir the mixture until the polymerization reaction is complete.

[0348] The resulting capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersant. The capsule suspension formulation contains 28% of the active ingredient. The diameter of the capsules is 8 to 15 micrometers.

[0349] The resulting formulation is applied to seeds as an aqueous suspension using equipment suitable for the purpose.

[0350] Analysis method Throughout this specification, temperatures are expressed in degrees Celsius (°C), and "mp" indicates the melting point. LC / MS stands for liquid chromatography-mass spectrometry, and the apparatus and method are described below.

[0351] LC-MS method: Method A: The spectra were recorded using a Waters mass spectrometer equipped with an electrospray source (SQD, SQDII single quadrupole mass spectrometer) (polarity: cation or anion, capillary: 3.00kV, cone range: 30V, extractor: 2.00V, source temperature: 150℃, desolvation temperature: 350℃, cone gas flow rate: 50l / hour, desolvation gas flow rate: 650l / hour, mass range: 100~900Da) and a Waters Acquity UPLC: binary pump, heated column compartment, diode array detector, and ELSD detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm, Temperature: 60°C, DAD wavelength range (nm): 210~500, Solvent gradient: A = Water + 5% MeOH + 0.05% HCOOH, B = Acetonitrile + 0.05% HCOOH, Gradient: 10~100% B (1.2 min); Flow rate (ml / min): 0.85.

[0352] Method B: Spectra were recorded using the following: an ACQUITY mass spectrometer (SQD or SQDII single quadrupole mass spectrometer) from Waters Corporation equipped with an electrospray source (polarity: positive and negative ions, capillary voltage: 3.0kV, cone voltage: 30V, extractor voltage: 3.00V, source temperature: 150°C, desolvation temperature: 400°C, cone gas flow rate: 60L / hour, desolvation gas flow rate: 700L / hour, mass range: 140~800Da), and an ACQUITY UPLC from Waters Corporation equipped with a solvent degasser, binary pump, heated column compartment, and diode array detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm, Temperature: 60°C, DAD wavelength range (nm): 210~400, Solvent gradient: A = Water / Methanol 9:1 + 0.1% Formic Acid, B = Acetonitrile + 0.1% Formic Acid, Gradient: 0~100% B over 2.5 minutes; Flow rate (ml / min) 0.75.

[0353] Method C: The spectra were obtained using a Waters Corporation mass spectrometer (SQD, SQDII, or QDA single quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive and negative ions), capillary voltage: 0.8~3.00kV, cone voltage: 5~30V, source temperature: 120~150℃, desolvation temperature: 350~600℃, cone gas flow rate: 50~150 l / h, desolvation gas flow rate: 650~1000 l / h, mass range: 110~950Da, and a Waters Corporation Acquity UPLC: binary pump, heated column compartment, diode array detector, and ELSD, with a Waters UPLC HSS column. T3, 1.8 μm, 30 × 2.1 mm, Temperature: 60°C, DAD wavelength range (nm): 210~400, Run time: 1.5 min; Solvent: A = Water + 5% MeOH + 0.05% HCOOH, B = Acetonitrile + 0.05% HCOOH; Flow rate (mL / min) 0.85, Gradient: 0.2 min at 10% B constant composition, then 1.0 min at 10~100% B, 0.2 min at 100% B constant composition, 0.05 min at 100~10% B, 0.05 min at 10% B constant composition.

[0354] Table A below summarizes the compounds of formula (I): -LC-MS data, e.g., retention time (RT), [M+H] + etc. -Type of method, and / or - Melting point (mp).

[0355] [Table 5-1]

[0356] [Table 5-2]

[0357] [Table 5-3]

[0358] [Table 5-4]

[0359] [Table 5-5]

[0360] [Table 5-6]

[0361] [Table 5-7]

[0362] [Table 5-8]

[0363] [Table 5-9]

[0364] Preparation example: Example 1: Preparation of methyl N-[4-[6-[(4-chlorobenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]phenyl]carbamate (compound 27) [ka] Step A: Preparation of 3-bromoimidazo[1,2-a]pyridine-6-amine (compound X-1) [ka] To a solution of 3-bromo-6-nitroimidazo[1,2-a]pyridine (1.00 g, 3.97 mmol) in ethyl acetate (30 mL), tin(II) chloride dihydrate (3.13 g, 15.9 mmol, 4.00 equivalents) was added, and the reaction mixture was stirred at room temperature for 16 hours. A 2 M sodium hydroxide solution was added to the suspension until the pH became basic. The suspension was filtered on a Celite pad, washed with ethyl acetate, and the filtrate was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluted with cyclohexane / ethyl acetate) to obtain 3-bromoimidazo[1,2-a]pyridine-6-amine as a green solid. LC-MS (Method A): Rt 0.15 min, m / z=212(M+H) + 1 H-NMR (400MHz, 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).

[0365] Step B: Preparation of N-(3-bromoimidazo[1,2-a]pyridine-6-yl)-4-chlorobenzamide [ka] 3-Bromoimidazo[1,2-a]pyridine-6-amine (compound X-1) (0.260 g, 1.13 mmol, 1.00 equivalent) and triethylamine (0.346 g, 3.38 mmol, 0.476 mL, 3.00 equivalent) were dissolved in tetrahydrofuran (7.80 mL). 4-Chlorobenzoyl chloride (0.302 g, 1.69 mmol, 0.221 mL, 1.50 equivalent) was added dropwise at 10°C to 15°C, and the mixture was stirred at room temperature for 1 hour. The mixture was diluted with ethyl acetate and treated with a saturated solution of sodium bicarbonate. The aqueous layer was extracted with ethyl acetate, the combined organic layers were washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluted with ethyl acetate / methanol) to obtain N-(3-bromoimidazo[1,2-a]pyridine-6-yl)-4-chlorobenzamide. LC-MS (Method A): Rt 0.84 min, m / z=350 / 352 / 354(M+H) + 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).

[0366] Step C: Preparation of N-(3-bromoimidazo[1,2-a]pyridine-6-yl)-4-chloro-N-methylbenzamide [ka] To an ice-cold mixture of N-(3-bromoimidazo[1,2-a]pyridine-6-yl)-4-chlorobenzamide (0.190 g, 0.488 mmol, 1.00 equivalent) in tetrahydrofuran (5.70 mL) purged with argon, sodium hydride (60% by mass in oil) (25.4 mg, 0.634 mmol, 1.30 equivalent) was added in small amounts, and the resulting mixture was stirred at 0°C for 20 minutes. 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 hours. The mixture was diluted with ethyl acetate and treated with ice-cold water. The aqueous layer was extracted with ethyl acetate, the combined organic layers were washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluting with cyclohexane / ethyl acetate) to obtain N-(3-bromoimidazo[1,2-a]pyridine-6-yl)-4-chloro-N-methyl-benzamide as a yellow-brown resin. LC-MS (Method A): Rt 0.84 min, m / z=364 / 366 / 368(M+H) + 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).

[0367] Step D: Preparation of methyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate [ka] To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.200 g, 0.895 mmol, 1.00 equivalent) and pyridine (0.216 g, 2.68 mmol, 3.00 equivalent) in ethyl acetate (4 mL), methyl chloroformate (0.213 g, 0.175 mL, 2.24 mmol, 2.50 equivalent) was added dropwise over 5 minutes at 10°C. The resulting mixture was stirred at room temperature for 1 hour. The mixture was diluted with ethyl acetate and treated with a saturated solution of sodium bicarbonate. The aqueous layer was extracted with ethyl acetate, the combined organic layers were washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluting with cyclohexane / ethyl acetate) to obtain methyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate. LC-MS (Method A): Rt 1.00 min, m / z=278(M+H) + 1 H-NMR (400MHz, 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).

[0368] Step E: Preparation of methyl N-[4-[6-[(4-chlorobenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]phenyl]carbamate (compound 27) Methyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (30.4 mg, 0.110 mmol, 2.00 equivalents), N-(3-bromoimidazo[1,2-a]pyridine-6-yl)-4-chloro-N-methylbenzamide (20.0 mg, 0.0549 mmol, 1.00 equivalent), cesium carbonate (26.8 mg, 0.0823 mmol, 1.50 equivalents), and tetrakis(triphenylphosphine)palladium(0) (3.170 mg, 0.002743 mmol, 0.050 equivalents) were dissolved in water (0.5 mL) and 1,4-dioxane (1.5 mL). The suspension was purged with an argon stream by three freeze-pump-thaw cycles and irradiated in microwaves at 100°C for 30 minutes. After cooling to room temperature, the reaction mixture was filtered through a Celite pad and washed with ethyl acetate. The filtrate was washed with water, then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by reverse-phase preparative HPLC (eluting with water / acetonitrile) to obtain methyl N-[4-[6-[(4-chlorobenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]phenyl]carbamate. LC-MS (Method A): Rt 0.74 min, m / z=435 / 437(M+H)+ 1 H-NMR (400MHz, 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, 1H),7.23-7.34(m,5H),7.45-7.53(m,2H),7.60-7.68(m,2H),7.70-7.82(m,1H).

[0369] Example 2: Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 26) [ka] Step A: Preparation of N-(3-bromoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxybenzamide (compound X-2) [ka] To a solution of 3-bromoimidazo[1,2-a]pyridine-6-amine (compound X-1, 2.00 g, 9.43 mmol, 1.00 equivalent) and 4-fluoro-3-methoxybenzoic acid (CAS: 82846-18-2) (1.60 g, 9.43 mmol, 1.00 equivalent) in pyridine (30 mL), a solution of 1-propanephosphonic anhydride (50% in ethyl acetate, 12.0 g, 18.9 mmol, 2.00 equivalent) was added dropwise under nitrogen. The resulting solution was stirred at 70°C for 3 hours. The reaction mixture was quenched with a saturated aqueous solution of sodium carbonate. The precipitate was collected by filtration, washed with water, and triturated with diethyl ether to obtain N-(3-bromoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxybenzamide as a brown solid. LC-MS (Method A): Rt 1.09 min, m / z=364 / 366(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=10.51(s,1H),9.24(dd,J=2.0,0.9Hz,1H),7.76(dd,J=8.3,2.1Hz,1H),7.72(d,J=5.7Hz,1H),7.72 -7.68(m,1H),7.65(ddd,J=8.5,4.4,2.2Hz,1H),7.60(dd,J=9.7,2.0Hz,1H),7.46-7.39(m,1H),3.96(s,3H).

[0370] Step B: Preparation of N-(3-bromoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-methylbenzamide [ka] The mixture was purged with an argon stream and ice-cold to an ice-cold mixture of N-(3-bromoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxybenzamide (compound X-2, 0.267 g, 0.706 mmol, 1.00 equivalent) dissolved in tetrahydrofuran (11.4 mL). Sodium hydride (60% by mass in oil) (0.0488 g, 1.22 mmol, 1.30 equivalent) was added in small amounts, and the resulting mixture was stirred at 0°C for 20 minutes. Iodomethane (0.200 g, 0.0877 mL, 1.41 mmol, 1.50 equivalent) 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 target substance was extracted with ethyl acetate, the combined organic layers were washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluted with cyclohexane / ethyl acetate; ethanol 3:1) to obtain N-(3-bromoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-methylbenzamide. LC-MS (Method A): Rt 0.77 min, m / z=378 / 380(M+H) + 1 H-NMR (400MHz, 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).

[0371] Step C: Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 26) N-(3-bromoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-methylbenzamide (0.267 g, 0.706 mmol, 1.00 equivalent) 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 equivalent) were dissolved in dioxane (4.24 mL) and water (1.41 mL). Cesium carbonate (0.345 g, 1.06 mmol, 1.50 equivalent) was added, and the mixture was purged with an argon stream for 5 minutes. Then, tetrakis(triphenylphosphine)palladium (0) (0.0421 g, 0.0353 mmol, 0.05 equivalent) 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 and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash column chromatography on silica gel (eluting with cyclohexane / ethyl acetate; ethanol 3:1) to obtain methyl N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate as a beige solid. LC-MS (Method A): Rt 0.67 min, m / z=450(M+H) + 1 H-NMR (400MHz, 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).

[0372] Example 3: Preparation of methyl N-[5-[6-[(4-cyano-3-ethoxy-benzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 16) [ka] Step A: Preparation of 3-bromo-N-methylimidazo[1,2-a]pyridine-6-amine [ka] To a solution of 3-bromoimidazo[1,2-a]pyridine-6-amine (compound X-1, 3.70 g, 17.4 mmol, 1.00 equivalent) in diethoxymethoxyethane (40.0 mL), 2,2,2-trifluoroacetic acid (0.0995 g, 0.872 mmol, 0.05 equivalent) was added. The solution was heated at 120 °C for 2 hours. The reaction mixture was cooled and concentrated to obtain a yellow liquid. To a solution of this liquid in anhydrous ethanol (40.0 mL), sodium borohydride (1.98 g, 52.3 mmol, 3.00 equivalent) was added at 0 °C. The resulting suspension was stirred at room temperature for 20 hours, then heated at 80 °C for 3 hours. 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 flash chromatography on silica gel (eluted with petroleum ether / ethyl acetate) to obtain 3-bromo-N-methylimidazo[1,2-a]pyridine-6-amine as a green solid. LC-MS (Method A): Rt 0.55 min, m / z=226(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=7.49(s,1H),7.41(d,J=9.6Hz,1H),7.10(d,J=1.2Hz,1H),6.94(dd,J=9.6,2.0Hz,1H),5.85(s,1H),2.70(d,J=3.8Hz,3H).

[0373] Step B: Preparation of methyl N-[5-[6-(methylamino)imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X-3) [ka] To a solution of 3-bromo-N-methylimidazo[1,2-a]pyridine-6-amine (2.70 g, 11.9 mmol, 1.00 equivalent) in dioxane / water (4:1, 35.0 mL), methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (CAS: 1073372-02-7) (3.99 mg, 14.3 mmol, 1.20 equivalent), potassium carbonate (4.13 g, 29.9 mmol, 2.50 equivalent), and 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (0.874 g, 1.19 mmol, 0.10 equivalent) were added. The mixture was stirred under nitrogen at 65°C 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 flash chromatography on silica gel (eluting with dichloromethane / methanol) to obtain methyl N-[5-[6-(methylamino)imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate as a green solid. LC-MS (Method A): Rt 0.70 min, m / z=298(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=10.37(s,1H),8.53(d,J=1.8Hz,1H),8.09(dd,J=8.6,2.4Hz,1H),7.99(d,J=8.6Hz,1H),7.57(s,1H),7.44(d,J= 9.4Hz,1H),7.32(s,1H),6.92(dd,J=9.6,2.0Hz,1H),5.66(d,J=4.8Hz,1H),3.71(d,J=6.4Hz,3H),2.64(d,J=4.2Hz,3H).

[0374] Step C: Preparation of methyl 4-cyano-3-ethoxybenzoate [ka] To a solution of methyl 4-cyano-3-hydroxybenzoate (CAS: 6520-87-2) (2.00 g, 11.3 mmol, 1.00 equivalent) in dimethylformamide (30.0 mL), cesium carbonate (7.356 g, 22.5 mmol, 2.00 equivalent) and iodoethane (5.28 g, 33.86 mmol) were added 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 obtain methyl 4-cyano-3-ethoxybenzoate as a white solid. 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=7.90(d,J=7.8Hz,1H),7.62(dd,J=9.4,1.4Hz,2H),4.28(q,2H),3.90(s,3H),1.39(t,3H).

[0375] Step D: Preparation of 4-cyano-3-ethoxybenzoic acid [ka] To a solution of methyl 4-cyano-3-ethoxybenzoate (2.00 g, 9.75 mmol, 1.00 equivalent) in methanol / tetrahydrofuran / water (5:5:4, 28.0 mL), lithium hydroxide (0.350 g, 14.6 mmol, 1.50 equivalent) was added. The reaction mixture was stirred at room temperature for 3 hours. The organic solvent was removed, and the aqueous solution was adjusted to pH 2-3 with 2N hydrogen chloride solution. The precipitate was collected by filtration and washed with water to obtain 4-cyano-3-ethoxybenzoic acid as a grayish-white solid. LC-MS (Method A): Rt 1.01 min, m / z=190(M+H) - 1 H-NMR (400MHz, DMSO-d 6,ppm)δ=13.53(s,1H),7.86(d,J=7.8Hz,1H),7.64-7.58(m,2H),4.27(q,2H),1.39(t,3H).

[0376] Step E: Preparation of methyl N-[5-[6-[(4-cyano-3-ethoxy-benzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 16) A solution of methyl N-[5-[6-(methylamino)imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X-3) (0.300 g, 1.01 mmol, 1.00 equivalent) and 4-cyano-3-ethoxybenzoic acid (0.212 g, 1.11 mmol, 1.10 equivalents) in pyridine (5.0 mL) was added dropwise to a solution of 1-propanephosphonic acid anhydride (50% in ethyl acetate, 1.93 g, 3.03 mmol, 3.00 equivalents) under nitrogen at 55°C. The mixture was stirred at 55°C for 3 hours. The resulting mixture was diluted with saturated sodium carbonate aqueous 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 obtain methyl N-[5-[6-[(4-cyano-3-ethoxybenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate as a white solid. LC-MS (Method A): Rt 0.96 min, m / z=471(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=10.43(s,1H),8.59(s,1H),8.40(s,1H),7.98(d,J=8.6Hz,1H),7.78(s,2H),7.59(d,J=1 2.4Hz,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).

[0377] Example 4: Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-(methoxymethyl)amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 25) [ka] Step A: Preparation of N-(3-bromoimidazo[1,2-a]pyridine-6-yl)4-fluoro-3-methoxy-N-(methoxymethyl)benzamide [ka] To a solution of N-(3-bromoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxybenzamide (compound X-2, 200 mg, 0.549 mmol, 1.00 equivalent) in dry tetrahydrofuran (4.0 mL), NaH (60.0% in oil) (43.9 mg, 1.10 mmol, 2.00 equivalent) was added under nitrogen at room temperature. The reaction mixture was stirred at room temperature for 60 minutes. Then, bromo(methoxy)methane (82.4 mg, 0.659 mmol, 1.20 equivalent) 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 flash chromatography on silica gel (eluted with dichloromethane / methanol) to obtain N-(3-bromoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-(methoxymethyl)benzamide as a viscous solid. LC-MS (Method A): Rt 1.10 min, m / z=408 / 410(M+H) +

[0378] Step B: Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-(methoxymethyl)amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 25) To a mixture of N(3-bromoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-(methoxymethyl)benzamide (200 mg, 0.490 mmol, 1.00 equivalent) and methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (CAS: 1073372-02-7) (204 mg, 0.735 mmol, 1.50 equivalent) in a pre-mixed dioxane / water (5:1, 8 mL), 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (35.8 mg, 0.049 mmol, 0.10 equivalent) and potassium carbonate (169 mg, 1.22 mmol, 2.50 equivalent) were added. The reaction mixture was stirred under nitrogen at 65°C for 1 hour. The reaction mixture was concentrated under reduced pressure, and the crude residue was purified by reverse-phase chromatography (eluting with acetonitrile / water containing 0.1% formic acid) to obtain methyl N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-(methoxymethyl)amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate as a grayish-white solid. LC-MS (Method A): Rt 0.90 min, m / z=480(M+H) + 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).

[0379] Example 5: Preparation of methyl N-[5-[6-[(2-methoxypyridine-4-carbonyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 8) [ka] To a mixture of 2-methoxypyridine-4-carboxylic acid (0.124 g, 0.807 mmol, 1.20 equivalents) in dimethylformamide (6 mL), 1-methylimidazole (0.166 g, 2.02 mmol, 3.00 equivalents) and [chloro(dimethylamino)methylene]-dimethyl-ammonium hexafluorophosphate (0.283 g, 1.01 mmol, 1.50 equivalents) were added. This reaction mixture was stirred at room temperature for 15 minutes. Then, methyl N-[5-[6-(methylamino)imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X-3, 0.200 g, 0.673 mmol, 1.00 equivalent) was added in small amounts. The resulting reaction mixture was stirred at room temperature for 2 hours. The mixture was filtered off, and the residue was purified by reverse-phase chromatography (eluting with water / acetonitrile containing 0.1% formic acid) to obtain methyl N-[5-[6-[(2-methoxypyridine-4-carbonyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate as a grayish-white solid. LC-MS (Method A): Rt 0.80 min, m / z=433(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=10.45(s,1H),8.61(s,1H),8.40(s,1H),8.00(d,J=8.7Hz,2H),7.85-7.71(m,2H),7.61(d,J=9 .6Hz,1H),7.35(d,J=9.4Hz,1H),6.94-6.85(m,1H),6.82(s,1H),3.75(s,3H),3.73(s,3H),3.36(s,3H)

[0380] Example 6: Preparation of methyl N-[5-[6-[(4-cyano-3-methoxy-benzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 9) [ka] Step A: Preparation of methyl 4-cyano-3-methoxybenzoate [ka] To a solution of methyl 4-cyano-3-hydroxybenzoate (1.00 g, 5.64 mmol, 1.00 equivalent) in dimethylformamide (15.0 mL), cesium carbonate (3.68 g, 11.3 mmol, 2.00 equivalent) and iodomethane (2.40 g, 16.9 mmol, 3.00 equivalent) were added. 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 obtain methyl 4-cyano-3-methoxybenzoate as a white solid. 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=7.91(d,J= 7.8Hz,1H),7.64(dd,J= 10.2,2.2Hz,2H),4.00(s,3H),3.91(s,3H).

[0381] Step B: Preparation of 4-cyano-3-methoxybenzoic acid [ka] A solution of methyl 4-cyano-3-methoxybenzoate (1.00 g, 5.23 mmol, 1.00 equivalent) in methanol / tetrahydrofuran / water (5:5:4, 14.0 mL) was mixed with lithium hydroxide (0.188 g, 7.85 mmol, 1.50 equivalent). 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 using 2N hydrogen chloride. The precipitate formed was filtered off, washed with water, and dried under reduced pressure to obtain 4-cyano-3-methoxybenzoic acid as a white solid. LC-MS (Method A): Rt 0.99 min, m / z=176(MH) - 1 H-NMR (400MHz, DMSO-d 6,ppm)δ=13.61(s,1H),7.87(d,J= 7.8Hz,1H),7.69-7.57(m,2H)3.99(s,3H).

[0382] Step C: Preparation of methyl N-[5-[6-[(4-cyano-3-methoxy-benzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 9) To a solution of 4-cyano-3-methoxybenzoic acid (0.150 g, 0.847 mmol, 1.00 equivalent) in dimethylformamide (4.0 mL), 1-methylimidazole (0.209 g, 2.54 mmol), followed by [chloro(dimethylamino)methylene]-dimethyl-ammonium hexafluorophosphate (0.356 g, 1.27 mmol, 1.5 equivalents) was added. The reaction mixture was stirred at room temperature for 15 minutes. Next, methyl N-[5-[6-(methylamino)imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X-3) (0.277 g, 0.931 mmol, 1.10 equivalents) was added. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with saturated sodium carbonate aqueous solution. The formed precipitate was filtered off, washed with water, and triturated in acetonitrile / tert-butyl methyl ether (2:1) to obtain methyl N-[5-[6-[(4-cyano-3-methoxy-benzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate as a grayish-white solid. LC-MS (Method A): Rt 0.90 min, m / z=457(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=10.43(s,1H),8.56(s,1H),8.34(s,1H),7.98(d,J=8.6Hz,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).

[0383] Example 7: Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxybenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 13) [ka] Step A: Preparation of tert-butyl N-(8-methylimidazo[1,2-a]pyridine-6-yl)carbamate [ka] A solution of 6-bromo-8-methylimidazo[1,2-a]pyridine (2.00 g, 9.48 mmol, 1.00 equivalent), tert-butyl carbamate (4.44 g, 37.9 mmol, 4.00 equivalent), and sodium 2-methylpropane-2-oleate (3.64 g, 37.9 mmol, 4.00 equivalent) in dioxane (30.0 mL) is prepared by adding [2-(2-aminophenyl)phenyl]-methyl Disulfonyloxypalladium;dicyclohexyl-[3,6-dimethoxy-2-(2,4,6-triisopropylphenyl)phenyl]phosphane (0.859 g, 0.948 mmol, 0.10 equivalents) and dicyclohexyl-[3,6-dimethoxy-2-(2,4,6-triisopropylphenyl)phenyl]phosphane (1.02 g, 1.90 mmol, 0.20 equivalents) were added. The reaction mixture was stirred under nitrogen at 100°C for 8 hours. The resulting mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluted with dichloromethane / methanol) to obtain tert-butyl N-(8-methylimidazo[1,2-a]pyridine-6-yl)carbamate as a yellow solid. LC-MS (Method A): Rt 0.74 min, m / z=248(M+H) +

[0384] Step B: Preparation of tert-butyl N-methyl-N-(8-methylimidazo[1,2-a]pyridine-6-yl)carbamate [ka] To an ice-cold solution of tert-butyl N-(8-methylimidazo[1,2-a]pyridine-6-yl)carbamate (0.0200 g, 0.0809 mmol, 1.00 equivalent) in tetrahydrofuran (3.00 mL), sodium hydride (60% in oil, 0.0029 g, 0.12 mmol, 1.3 equivalents) was added under nitrogen. The solution was stirred at 0°C for 45 minutes, and then iodomethane (0.0230 g, 0.162 mmol, 2.00 equivalents) was added dropwise. The resulting solution was slowly warmed to room temperature and stirred for 3 hours. 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 obtain tert-butyl N-methyl-N-(8-methylimidazo[1,2-a]pyridine-6-yl)carbamate as a yellow solid. LC-MS (Method A): Rt 0.76 min, m / z=262(M+H)+

[0385] Step C: Preparation of tert-butyl N-[3-bromo-8-methylimidazo[1,2-a]pyridine-6-yl]-N-carbamate [ka] A solution of tert-butyl N-methyl-N-(8-methylimidazo[1,2-a]pyridine-6-yl)carbamate (0.480 g, 1.84 mmol, 1.00 equivalent) in dimethylformamide (4.00 mL) was met with a dropwise addition of a solution of 1-bromopyrrolidine-2,5-dione (0.360 g, 2.02 mmol, 1.10 equivalent) in dimethylformamide (1.0 mL). The reaction mixture was stirred at room temperature for 1 hour. 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 obtain tert-butyl N-[3-bromo-8-methylimidazo[1,2-a]pyridine-6-yl]-N-carbamate as a yellow solid. LC-MS (Method A): Rt 1.23 min, m / z=340 / 342(M+H) +

[0386] Step D: Preparation of 3-bromo-N,8-dimethylimidazo[1,2-a]pyridine-6-amine [ka] A solution of tert-butyl N-[3-bromo-8-methylimidazo[1,2-a]pyridine-6-yl]-N-carbamate (8.40 g, 24.7 mmol, 1.00 equivalent) in dichloromethane / trifluoroacetic acid (1:1, 100.0 mL) was stirred at room temperature for 1 hour. The aqueous solution was diluted with a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to obtain 3-bromo-N,8-dimethylimidazo[1,2-a]pyridine-6-amine as a yellow solid. LC-MS (Method A): Rt 0.62 min, m / z=240 / 242(M+H) +

[0387] Step E: Preparation of methyl N-[5-[8-methyl-6-(methylamino)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate [ka] 3-bromo-N,8-dimethylimidazo[1,2-a]pyridine-6-amine (0.750 g, 3.12 mmol, 1.00 equivalent), methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (1.04 g, 3.75 mmol, 1.20 equivalent), and dipotassium carbonate (1.08 g, 7.81 mmol, 2.50 equivalent) were stirred together in dioxane / water (5:1, 10.0 mL). 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloromethane complex (0.255 g, 0.312 mmol, 0.1 equivalent) was added to this mixture. The reaction mixture was stirred under nitrogen at 60°C for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by flash chromatography on silica gel (eluted with dichloromethane / methanol) to obtain methyl N-[5-[8-methyl-6-(methylamino)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate as a white solid. LC-MS (Method A): Rt 0.80 min, m / z=312(M+H)+

[0388] Step F: Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 13) To a mixture of 4-fluoro-3-methoxybenzoic acid (0.0656 g, 0.385 mmol, 1.20 equivalents) in dimethylformamide (6 mL), 1-methylimidazole (0.0791 g, 0.964 mmol, 3.00 equivalents) and [chloro(dimethylamino)methylene]-dimethylammonium hexafluorophosphate (0.135 g, 0.482 mmol, 1.50 equivalents) were added. The reaction mixture was stirred at room temperature for 5 minutes. Then, methyl N-[5-[8-methyl-6-(methylamino)imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (0.100 g, 0.321 mmol, 1.00 equivalent) was added in small amounts. The resulting reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with saturated sodium bicarbonate aqueous 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 resulting residue was purified by reverse-phase chromatography (water / acetonitrile containing 0.1% formic acid) to obtain methyl N-[5-[6-[(4-fluoro-3-methoxybenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate as a white solid. LC-MS (Method A): Rt 0.93 min, m / z=464(M+H) + 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).

[0389] Example 8: Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-(2-methoxyethyl)amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 14) [ka] Step A: Preparation of N-(3-bromoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-(2-methoxyethyl)benzamide [ka] To a solution of N-(3-bromoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxybenzamide (compound X-2) (0.260 g, 0.714 mmol, 1.00 equivalent) in dimethylformamide (6.0 mL), sodium 2-methylpropane-2-oleate (0.172 g, 1.78 mmol, 2.50 equivalents) and 1-bromo-2-methoxyethane (0.397 g, 2.86 mmol, 4.00 equivalents) were added under nitrogen. The reaction mixture was stirred at 80°C for 16 hours. The resulting reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluted with dichloromethane / methanol) to obtain N-(3-bromoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-(2-methoxyethyl)benzamide as a green oil. LC-MS (Method A): Rt 1.09 min, m / z=422 / 424(M+H) +

[0390] Step B: Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-(2-methoxyethyl)amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 14) To a solution of N-(3-bromoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-(2-methoxyethyl)benzamide (80.0 mg, 0.189 mmol, 1.00 equivalent), methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (0.0632 g, 0.227 mmol), and potassium carbonate (0.0655 g, 0.474 mmol, 2.50 equivalents), 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (0.0139 g, 0.0189 mmol, 0.10 equivalent) was added. The reaction mixture was stirred under nitrogen at 65°C for 2 hours. 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 obtain methyl N-[5-[6-[(4-fluoro-3-methoxy-benzoyl)-(2-methoxyethyl)amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate as a white solid. LC-MS (Method A): Rt 0.92 min, m / z=494(M+H) + 1 H-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)

[0391] Example 9: Preparation of methyl N-[5-[6-[(4-cyano-3-methylbenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 17) [ka] To a mixture of 4-cyano-3-methylbenzoic acid (0.02 g, 0.124 mmol, 1.00 equivalent) in dimethylformamide (2 mL), 1-methylimidazole (0.0306 g, 0.372 mmol, 3.00 equivalent) and [chloro(dimethylamino)methylene]-dimethylammonium hexafluorophosphate (0.052 g, 0.186 mmol, 1.50 equivalent) were added. The reaction mixture was stirred at room temperature for 5 minutes. Then, N-[5-[6-(methylamino)imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X-3) (0.044 g, 0.149 mmol, 1.00 equivalent) was added in small amounts. The resulting reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was quenched with saturated sodium bicarbonate aqueous 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 crude residue was purified by reverse-phase chromatography (eluted with water / acetonitrile containing 0.1% formic acid) to obtain methyl N-[5-[6-[(4-cyano-3-methylbenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate as a white solid. LC-MS (Method A): Rt 0.88 min, m / z=441(M+H) + 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).

[0392] Example 10: Preparation of methyl N-[5-[6-[(4-cyano-3-methylbenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 2) [ka] To a mixture of 4-cyano-3-methylbenzoic acid (CAS 73831-13-7, 0.0656 g, 0.385 mmol) in N,N-dimethylformamide (3.00 mL), 1-methylimidazole (0.0791 g, 0.964 mmol) and [chloro(dimethylamino)methylene]-dimethylammonium hexafluorophosphate (0.135 g, 0.482 mmol) were added at room temperature. The solution was stirred for 5 minutes. Then, methyl N-[5-[8-methyl-6-(methylamino)imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X-4, 0.100 g, 0.321 mmol) was added in small amounts. The resulting solution was stirred for 2 hours. 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 reverse-phase chromatography (eluted with acetonitrile / water containing 0.1% formic acid) to obtain methyl N-[5-[6-[(4-cyano-3-methylbenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate as a white solid. LC-MS (Method A): Rt 0.92 min, m / z=455(M+H) + 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).

[0393] Example 11: Preparation of methyl N-[5-[6-[(4-cyano-3-ethoxy-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 10) [ka] Step A: Preparation of 4-cyano-3-ethoxybenzoic acid [ka] Lithium hydroxide (0.350 g, 14.6 mmol) was added to a solution of methyl 4-cyano-3-ethoxybenzoate (CAS 220380-12-1, 2.00 g, 9.75 mmol) in methanol / tetrahydrofuran / water (5:5:4, 28.0 mL). The mixture was stirred at room temperature for 3 hours. The organic solvent was then removed under reduced pressure. The aqueous solution was adjusted to pH 2-3 with 2N hydrochloric acid. The precipitate was collected by filtration and washed with water to obtain 4-cyano-3-ethoxybenzoic acid as a white solid. LC-MS (Method A): Rt 1.10 min, m / z=189.9(MH) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=13.53(s,1H),7.86(d,J=7.8Hz,1H),7.64-7.58(m,2H),4.27(q,J=7.0Hz,2H),1.39(t,J=7.0Hz,3H).

[0394] Step B: Preparation of methyl N-[5-[6-[(4-cyano-3-ethoxy-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 10) A solution of methyl N-[5-[8-methyl-6-(methylamino)imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X-4, 0.200 g, 0.642 mmol) and 4-cyano-3-ethoxybenzoic acid (0.135 g, 0.707 mmol) in pyridine (3.0 mL) was met with a 50.0% solution of propanephosphonic anhydride (2.45 g, 3.85 mmol) added dropwise under nitrogen 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 sodium bicarbonate aqueous solution and extracted with ethyl acetate. The combined organic layers were washed with water and then brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by reverse-phase chromatography (eluting with water / acetonitrile containing 0.1% formic acid) to obtain methyl N-[5-[6-[(4-cyano-3-ethoxybenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate as a grayish-white solid. LC-MS (Method A): Rt 0.95 min, m / z=485(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=10.42(s,1H),8.37(d,J=16.4Hz,2H),7.97(d,J=8.6Hz,1H),7.72(d,J=10.6Hz,2H),7.56(s,1H) ),7.26(d,J=10.0Hz,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).

[0395] Example 12: Preparation of methyl N-[5-[6-[(3-ethoxy-4-fluoro-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 19) [ka] To a mixture of 3-ethoxy-4-fluorobenzoic acid (0.0650 g, 0.353 mmol) in N,N-dimethylformamide (2.00 mL), 1-methylimidazole (0.0869 g, 1.06 mmol) and [chloro(dimethylamino)methylene]-dimethyl-ammonium hexafluorophosphate (0.149 g, 0.529 mmol) were added at room temperature. The solution was stirred for 5 minutes. Then, methyl N-[5-[8-methyl-6-(methylamino)imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X-4, 0.121 g, 0.388 mmol) was added in small amounts. The resulting solution was stirred at room temperature for 2 hours. 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 resulting residue was purified by reverse-phase chromatography (eluting with acetonitrile / water containing 0.1% formic acid) to obtain methyl N-[5-[6-[(3-ethoxy-4-fluoro-benzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate as a grayish-white solid. LC-MS (Method A): Rt 0.96 min, m / z=478(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=10.43(s,1H),8.35(d,J=13.8Hz,2H),7.96(d,J=8.6Hz,1H),7.78(s,1H),7.71(d,J=8.4Hz,1H),7.26(s,1H),7.18(d,J= 7.8Hz,1H),7.11-7.05(m,1H),6.89(s,1H),3.91(q,J=6.6Hz,2H),3.72(s,3H),3.35(s,3H),2.48(s,3H),1.16(t,J=6.8Hz,3H).

[0396] Example 13: Preparation of methyl N-[5-[6-[(3-methoxybenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 53) [ka] 3-methoxybenzoic acid (0.6 mmol) in N,N-dimethylacetamide (0.30 mL) was placed in a vial, followed by diisopropylethylamine (0.041 mL, 0.24 mmol), methyl N-[5-[8-methyl-6-(methylamino)imidazo[1,2-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)phosphinate chloride (20.6 mg, 0.080 mmol) in N,N-dimethylacetamide (0.50 mL). The reaction mixture was stirred at 60°C for 4 hours. Next, methanol (0.30 mL) was added, and the mixture was purified by reverse-phase chromatography to obtain memethyl N-[5-[6-[(3-methoxybenzoyl)-methyl-amino]-8-methyl-imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate. LC-MS (Method D): Rt 0.83 min, m / z=446(M+H) +

[0397] Example 14: Preparation of methyl N-[5-[8-acetamido-6-[(4-fluoro-3-methoxybenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 59) [ka] Step A: Preparation of 8-bromo-6-nitroimidazo[1,2-a]pyridine (compound X-5) [ka] To a stirred solution of 3-bromo-5-nitropyridine-2-amine (10.0 g, 45.9 mmol) in ethanol (100 mL), 2-chloroacetaldehyde (25.2 g, 321 mmol) and sodium bicarbonate (6.94 g, 82.6 mmol) were added at room temperature. The reaction mixture was stirred at 80 °C for 16 hours. The solvent was then removed, the residue was basicized with saturated sodium bicarbonate aqueous solution, and extracted with dichloromethane. The combined organic phase was concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluted with petroleum ether / ethyl acetate) to obtain 8-bromo-6-nitroimidazo[1,2-a]pyridine as a yellow solid. LC-MS (Method A): Rt 0.95 min, m / z=242(M+2H) 2+

[0398] Step B: Preparation of 8-bromoimidazo[1,2-a]pyridine-6-amine [ka] To a solution of 8-bromo-6-nitroimidazo[1,2-a]pyridine (compound X-5) (5.00 g, 20.7 mmol) in ethanol / water (1:1, 60.0 mL), ammonium chloride (5.53 g, 103 mmol) and iron (5.77 g, 103 mmol) were added 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 under vacuum. The residue was purified by flash chromatography on silica gel (eluting with pentane / ethyl acetate) to obtain 8-bromoimidazo[1,2-a]pyridine-6-amine as a yellow solid. LC-MS (Method A): Rt 0.22 min, m / z=214(M+2H) 2+

[0399] Step C: Preparation of 8-bromo-N-methylimidazo[1,2-a]pyridine-6-amine [ka] To a solution of 8-bromoimidazo[1,2-a]pyridine-6-amine (0.400 g, 1.89 mmol) in triethyl orthoformate (4.0 mL), trifluoroacetic acid (0.0108 g, 0.0943 mmol) was added. The reaction was heated at 120 °C for 2 hours. The mixture was then cooled 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 in small amounts 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 obtain 8-bromo-N-methylimidazo[1,2-a]pyridine-6-amine as a brown solid, which was used in the next step without further purification. LC-MS (Method A): Rt 0.31 min, m / z=226(M+H) +

[0400] Step D: Preparation of N-(8-bromoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-methylbenzamide (compound X-6) [ka] To a solution of 8-bromo-N-methylimidazo[1,2-a]pyridine-6-amine (1.50 g, 6.64 mmol) and 4-fluoro-3-methoxybenzoic acid (1.35 g, 7.96 mmol) in pyridine (20.0 mL), propanephosphonic anhydride (50.0%, 6.33 g, 19.9 mmol) was added 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 layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluted with dichloromethane / methanol) to obtain N-(8-bromoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-methylbenzamide as a yellow solid. LC-MS (Method A): Rt 0.93 min, m / z=380(M+H)+

[0401] Step E: Preparation of N-(8-acetamidoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-methylbenzamide [ka] To a solution of N-(8-bromoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-methylbenzamide (compound X-6) (0.200 g, 0.529 mmol) in dioxane (2.00 mL), acetamide (0.0625 g, 1.06 mmol), xanthophos Pd G2 (0.0470 g, 0.0529 mmol), and cesium carbonate (0.516 g, 1.59 mmol) were added. The mixture was stirred at 100°C for 16 hours under an N2 atmosphere. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluted with methanol / dichloromethane) to obtain N-(8-acetamidoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-methylbenzamide as a white solid. LC-MS (Method A): Rt 1.24 min, m / z=357(M+H) +

[0402] Step F: Preparation of N-(8-acetamido-3-bromoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-methylbenzamide [ka] To a solution of N-(8-acetamidoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-methyl-benzamide (0.130 g, 0.365 mmol) in dichloromethane (4.0 mL), N-bromosuccinimide (0.0714 g, 0.401 mmol) was added under nitrogen at -30°C for 1 hour. 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 flash chromatography on silica gel (dichloromethane / methanol elution) to obtain N-(8-acetamido-3-bromo-imidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-methyl-benzamide as a white solid. LC-MS (Method A): Rt 1.42 min, m / z=435(M+H) +

[0403] Step G: Preparation of methyl N-[5-[8-acetamido-6-[(4-fluoro-3-methoxybenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 59) To a solution of N-(8-acetamido-3-bromoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-methylbenzamide (0.130 g, 0.299 mmol) in dioxane (4.00 mL) and water (1.00 mL), methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (0.166 g, 0.597 mmol), 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (0.0217 g, 0.0299 mmol), and potassium carbonate (0.0832 g, 0.597 mmol) were added. The mixture was stirred under a nitrogen atmosphere at 50°C for 2.5 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 flash chromatography on silica gel (eluted with dichloromethane / methanol) to obtain methyl N-[5-[8-acetamido-6-[(4-fluoro-3-methoxybenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate as a white solid. LC-MS (Method A): Rt 1.04 min, m / z=507(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ =10.44(s,1H),10.16(s,1H),8.35(d,J=2.4Hz,1H),8.19(s,1H),8.04(d,J=1.8Hz,1H),7.97(d,J=8.7Hz,1H),7.78(s,1H),7. 73(d,J=8.6Hz,1H),7.24(d,J=8.3Hz,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).

[0404] Example 15: Preparation of methyl N-[5-[8-cyano-6-[(4-fluoro-3-methoxybenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 55) [ka] Step A: Preparation of N-(8-cyanoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-methylbenzamide [ka] To a solution of N-(8-bromoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-methylbenzamide (compound X-6) (0.200 g, 0.529 mmol) in N,N-dimethylacetamide (3.00 mL), zinc cyanide (0.124 g, 1.06 mmol), (5-diphenylphosphanyl-9,9-dimethyl-xanthene-4-yl)-diphenylphosphan (0.0612 g, 0.106 mmol), and Pd2(dba)3 (0.0484 g, 0.0529 mmol) were sequentially added. The mixture was heated under nitrogen in a microwave reactor at 100°C for 1 hour. 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 (eluted with dichloromethane / methanol) to obtain N-(8-cyanoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-methylbenzamide as a green solid. LC-MS (Method A): Rt 0.97 min, m / z=325(M+H) +

[0405] Step B: Preparation of N-(3-bromo-8-cyanoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-methylbenzamide [ka] To a solution of N-(8-cyanoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-methyl-benzamide (0.190 g, 0.586 mmol) in dichloromethane (3.0 mL), N-bromosuccinimide (0.104 g, 0.586 mmol) was added at -30°C, 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 flash chromatography on silica gel (eluted with petroleum ether / ethyl acetate) to obtain N-(3-bromo-8-cyanoimidazo[1,2-a]pyridine-6-yl)-4-fluoro-3-methoxy-N-methyl-benzamide as a yellow solid. LC-MS (Method A): Rt 1.15 min, m / z=403(M+H) +

[0406] Step C: Preparation of methyl N-[5-[8-cyano-6-[(4-fluoro-3-methoxybenzoyl)-methyl-amino]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 55) To a...

Claims

1. Equation (I): 【Chemistry 1】 (wherein Z is O or S, preferably Z is O; A 1 However, it is CH or N; R 1a 、 R 1b and R 1c are independently selected from hydrogen, hydroxy, halogen, CN, C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 alkoxy-C 1-6 alkyl, C 3-6 cycloalkyl-C 1-4 alkyl, C 1-6 alkylsulfanyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 alkoxy, amino, C 2-4 alkenyl, and -NHC(O)C 1-6 alkyl; A 2 However, CR 2 Alternatively, selected independently of N, provided that A is 4 or less. 2 It is N, preferably three or fewer A 2 is N, preferably two or fewer A 2 is N, preferably one or less A 2 N is more preferably five A 2 CR 2 And; R 2 However, 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 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 Alkylcarbonyl, C 1-6 Alkoxycarbonyl, 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 Independently selected from cycloalkylaminos, where 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 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, 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 cycloalkylamino groups may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs; R 4 is C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 alkoxy, C 1-6 alkylsulfanyl-C 1-6 alkyl, C 1-6 alkylsulfinyl-C 1-6 alkyl, C 1-6 alkylsulfonyl-C 1-6 alkyl, C 1-6 alkoxycarbonyl-C 1-6 alkyl, C 1-6 alkylaminocarbonyl-C 1-6 alkyl, diC 1-6 alkylaminocarbonyl-C 1-6 alkyl, and selected from CN, where 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[[ID=​ R 5 However, 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 Alkoxyaminos and C 1-6 Alkyl C 1-6 Selected from alkoxyaminos, where 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 Alkoxyaminos and C 1-6 Alkyl C 1-6 Each alkoxyamino group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CNs; A compound thereof, or its salt or N-oxide.

2. R 1a , R 1b and R 1c However, hydrogen, 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 A compound according to claim 1, independently selected from alkoxys.

3. R 1a , R 1b and R 1c However, hydrogen, C 2-4 Alkenyl and C 1-6 A compound according to claim 1 or 2, independently selected from alkyl groups.

4. R 1a and R 1c is hydrogen, R 1b However, 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 A compound according to claim 1, selected from alkyl groups.

5. R 2 However, 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 Independently selected from alkylcarbonyls, where 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 The compound according to any one of claims 1 to 4, wherein each alkylcarbonyl group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs.

6. The four A's 2 CR 4 And one A 2 A compound according to any one of claims 1 to 5, wherein is N. 【Request Item 7】 【Chemistry 2】 but 【Transformation 3】 Preferably, four A 2 CR 2 The compound according to any one of claims 1 to 6. 【Request Item 8】 【Chemistry 4】 but 【Transformation 5】 Preferably, four A 2 CR 2 The compound according to any one of claims 1 to 6.

9. Five A's 2 CR 2 The compound according to any one of claims 1 to 5. 【Request Item 10】 【Chemistry 6】 but 【Transformation 7】 The compound according to claim 9.

11. R 4 However, 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 Selected from alkoxy, where 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 The compound according to any one of claims 1 to 10, wherein each alkoxy group may be optionally substituted with one to three substituents independently selected from halogens and CNs.

12. R 5 However, 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 The compound according to any one of claims 1 to 11, selected from alkynyl groups, wherein each of the groups may be optionally substituted with 1 to 3 substituents independently selected from halogens and CNs.

13. A composition comprising a fungicidal amount of the compound according to any one of claims 1 to 12.

14. The composition according to claim 14, further comprising at least one compound selected from additional active ingredients, suitable inactive ingredients, carriers, auxiliaries, and any mixtures thereof.

15. A method for eradicating, preventing, or controlling plant pathogenic diseases, comprising applying a fungicidal amount of a compound according to any one of claims 1 to 12, or a composition containing a compound according to any one of claims 1 to 12, or a composition according to claim 13 or 14, to a plant pathogen, a habitat of a plant pathogen, a plant susceptible to damage by a plant pathogen, or a plant reproductive material thereof.

16. Formula (II): 【Transformation 8】 (wherein Z is O or S, preferably Z is O; R 1a , R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, 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 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, C 2-4 Alkenyl and -NHC(O)C 1-6 Selected independently of alkyl groups; preferably, R 1a and R 1c is hydrogen, R 1b However, hydrogen, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl and C 2-4 Can be selected from Alkenil; A 2 However, CR 2 Alternatively, selected independently of N, provided that there are four or fewer A's. 2 It is N, preferably three or fewer A 2 is N, preferably two or fewer A 2 is N, preferably one or less A 2 N is more preferably five A 2 CR 2 And; R 2 However, 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 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, 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 Independently selected from cycloalkylaminos, where 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 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 Alkylcarbonyl, C 1-6 Alkoxycarbonyl, 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 cycloalkylamino groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs, more preferably R 2 However, 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 sulfanyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl and diC 1-6 Independently selected from alkylaminocarbonyl, where 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 sulfanyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, and C 1-6 Each alkylcarbonyl group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs; R 4 However, 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 Alkenil, C 2-6 Alkinyl, 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 Selected from alkyl and CN, where 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 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl and diC 1-6 Alkylaminocarbonyl-C 1-6 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CNs, preferably R 4 However, 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 Selected from alkoxy, where 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 be optionally substituted with 1 to 3 substituents independently selected from halogens and CNs; and X is Cl, Br, or I); Compounds thereof, or their salts or N-oxides, Or Formula (X): 【Chemistry 9】 (wherein Z is O or S, preferably Z is O; R 1a , R 1b and R 1c However, 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 sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, C 2-4 Alkenyl and -NHC(O)C 1-6 Selected independently of alkyl groups; preferably, R 1a and R 1c is hydrogen, R 1b is hydrogen, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl and C 2-4 Can be selected from Alkenil; A 2 However, CR 2 Alternatively, selected independently of N, provided that there are four or fewer A's. 2 It is N, preferably three or fewer A 2 is N, preferably two or fewer A 2 is N, preferably one or less A 2 N is more preferably five A 2 CR 2 And; R 2 However, 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 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, 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 Independently selected from cycloalkylaminos, where 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 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 Alkylcarbonyl, C 1-6 Alkoxycarbonyl, 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 cycloalkylamino groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs, more preferably R 2 However, 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 sulfanyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl and diC 1-6 Independently selected from alkylaminocarbonyl, where 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 sulfanyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl and diC 1-6 Each alkylaminocarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; and R 4 However, 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 Alkenil, C 2-6 Alkinyl, 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 Selected from alkyl and CN, where 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 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl and diC 1-6 Alkylaminocarbonyl-C 1-6 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CNs, preferably R 4 However, 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 Selected from alkoxy, where 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 alkoxy group may be optionally substituted with one to three substituents independently selected from halogens and CNs; A compound thereof, or its salt or N-oxide.

17. Formula (XVII): 【Chemistry 10】 (In the formula, A 1 However, it is CH or N, preferably N; R 1a , R 1b and R 1c ga is 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 sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, C 2-4 Alkenyl and -NHC(O)C 1-6 Selected independently of alkyl groups; preferably, R 1a and R 1c is hydrogen, R 1b However, hydrogen, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl and C 2-4 Can be selected from Alkenil; and R 5 However, 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 acids, and C 1-6 Alkyl C 1-6 Selected from alkoxyaminos, where 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 Alkoxyaminos and C 1-6 Alkyl C 1-6 Each alkoxyamino group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CNs, preferably R 5 However, 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 Selected from alkyl groups, where each of the groups may be optionally substituted with 1 to 3 substituents independently selected from halogens and CNs); Compounds thereof, or their salts or N-oxides, Or Formula (XVIII): 【Chemistry 11】 (In the formula, A 1 However, it is CH or N, preferably N; R 1a , R 1b and R 1c However, 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 sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, C 2-4 Alkenyl and -NHC(O)C 1-6 Selected independently of alkyl groups; preferably, R 1a and R 1c is hydrogen, R 1b However, hydrogen, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl and C 2-4 Can be selected from Alkenil; R 4 However, 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 Alkenil, C 2-6 Alkinyl, 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 Selected from alkyl and CN, where 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 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl and diC 1-6 Alkylaminocarbonyl-C 1-6 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CNs, preferably R 4 However, 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 Selected from alkoxy, where 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 be optionally substituted with 1 to 3 substituents independently selected from halogens and CNs; and R 5 However, 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 acids, and C 1-6 Alkyl C 1-6 Selected from alkoxyaminos, where 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 Alkoxyaminos and C 1-6 Alkyl C 1-6 Each alkoxyamino group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CNs, preferably R 5 However, 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 Selected from alkyl groups, where each of the groups may be optionally substituted with 1 to 3 substituents independently selected from halogens and CNs); A compound thereof, or its salt or N-oxide.

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