Imidazo[1,2-a]pyridine derivatives

Abstract

The present invention relates to formula (I) [Formula 1] JPEG2026513998000166.jpg59125 (wherein the formula, the substituents are as defined in claim 1) The present invention relates to a compound of formula (I), a process and method for preparing a compound of formula (I), a pesticide composition comprising a compound of formula (I) as defined in claim 1, the preparation of these compositions, and the use of the compound or composition in agriculture or horticulture for controlling, preventing or controlling 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 a microbicidal activity, particularly a fungicidal activity, more specifically an activity against oomycetes, for example, a microbicidal imidazo[1,2-a]pyridine derivative as an active ingredient. 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, an agrochemical composition containing at least one of the imidazo[1,2-a]pyridine derivatives, the preparation of these compositions, and the use of the imidazo[1,2-a]pyridine derivatives or compositions in agriculture or horticulture for controlling, preventing or eradicating the ectoparasitism of plant pathogenic microorganisms, particularly fungi, more specifically oomycetes, on plants, harvested food crops, seeds or non-living materials.

Background Art

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

Summary of the Invention

Means for Solving the Problems

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

Chemical Formula

[0003] , 1-6 is CH or N, preferably N, R 1a , R 1b and R 1c are 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 1-6Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and -NHC(O)C 1-6 Selected independently of alkyl, A 2 CR is independent. 2 or N, provided there are 3 or fewer A 2 is N, preferably two or fewer A 2 is N, preferably one or less A 2 is N, and more preferably four A 2 CR 2 The condition is that, 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-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 and C 1-6 Independently selected from alkylcarbonyls, 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, C1-6 Alkylsulfanyl, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Each of the alkylcarbonyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxy and CN, A 3 is CR 3 or N, R 3 is hydroxy, halogen, CN, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkoxy, C 2-6 alkenyl, C 2-6 alkynyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 alkyl, C 1-6 alkoxycarbonyl, C 1-6 alkylsulfanyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, amino, C 1-6 alkylamino, diC 1-6 -alkylamino and C 3-6 selected from cycloalkylamino, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkoxy, C 2-6 alkenyl, C 2-6 alkynyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 alkyl, C 1-6 alkoxycarbonyl, C 1-6 alkylsulfanyl, C1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, 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 halogen, hydroxy and CN, R 3 together with an adjacent R 2 may optionally form a ring, preferably a 5- to 8-membered heterocyclic ring, more preferably a 5-membered heterocyclic ring or a 6-membered heterocyclic ring, 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 selected from alkyl and CN, 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 1-6Alkylsulfinyl-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. A 3 and R 4 Together, they arbitrarily form a ring, preferably a 5-8 membered heterocycle, more preferably a 6-membered heterocycle, 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, 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 CN. The present invention provides compounds or salts or N-oxides thereof.

[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 fungicidal effective amount of a compound of formula (I). The composition may further comprise at least one compound selected from additional active ingredients, suitable formulation 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) or compositions containing compounds of formula (I) according to the present invention can be applied directly to plant pathogens, the habitats of plant pathogens, and especially to plants or plant reproductive materials that are susceptible to attack by plant pathogens.

[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 a plant pathogen, comprising applying a compound of formula (I) described herein or a composition comprising a compound of formula (I) to the plant pathogen, the habitat of the plant pathogen, in particular plants or plant reproductive materials susceptible to attack by the plant pathogen. According to this fourth aspect of the present invention, the method may exclude methods of treating the body of a human or animal by surgery or treatment.

[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 comprising compounds of formula (I) for the control of 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 or plant reproductive materials susceptible to attack by plant pathogenic fungi, particularly oomycetes. According to this sixth aspect of the present invention, this method may exclude methods of treating the body of a human or animal by surgery or treatment.

[0010] When it is indicated that one group is substituted (e.g., alkyl), this includes these groups being part of the other groups (e.g., alkyl 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 linear or branched hydrocarbons 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, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl, are preferred.

[0014] - The term "alkenyl," either alone or as part of a chemical group, preferably refers to 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-di 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, such as 2-propenyl, 2-butenyl, or 1-methyl-2-propenyl, is preferred.

[0015] - The term "alkynyl," either alone or as part of a chemical group, preferably refers to 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 , 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, such as ethynnyl, 2-propynyl or 2-butynyl-2-propenyl, are preferred.

[0016] - The term "haloalkyl" refers to alkyl groups, as generally defined above, that are substituted by one or more identical or different halogen atoms, such as fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, or 2,2,2-trifluoroethyl.

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

[0018] - The term "cycloalkyl," either alone or as part of a chemical group, preferably refers to saturated or partially unsaturated monocyclic, bicyclic, or tricyclic hydrocarbons 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, such as cyclopropyl or cyclobutyl, are preferred.

[0019] - The term "halocycloalkyl" refers to a cycloalkyl ring as defined above, which is substituted by one or more identical or different halogen atoms.

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

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

[0022] - The term "alkylsulfanyl" is derived from the formula -SR a (In the formula, R a This refers to the group of an alkyl group (which is generally defined above).

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

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

[0025] - The term "alkoxycarbonyl" is derived from the formula R a OC(O)-(wherein, R a This refers to the group of an alkyl group (which is generally defined above).

[0026] - The term "alkoxycarbonyl" is derived from the formula R a OC(O)-(wherein, R a This refers to the group of an alkyl group (which is generally defined above).

[0027] - The term "alkylamino" is derived from the formula R a NH-(wherein, R a This refers to the group of an alkyl group (which is generally defined above).

[0028] - The term "cycloalkylamino" is derived from the formula R a NH (in the formula, R a This refers to the group of a cycloalkyl group (which is generally defined as above).

[0029] - The term "alkoxyamino" is derived from the formula R a (In the formula, R a This refers to the group of an alkoxy group (as generally defined above).

[0030] - The term "alkylaminocarbonyl" is derived from the formula R a NHC(O)-(wherein, R a This refers to the group of an alkyl group (which is generally defined above).

[0031] - Hydroxyl or hydroxy 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 oomycetes and other fungi, 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 dose can be readily determined by those skilled in the art by using known techniques and observing the results obtained under similar circumstances. In determining the effective dose, many factors are considered, including but 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 other relevant circumstances.

[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, along with 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, alkane- or arylsulfonic acids, such as methane- or p-toluenesulfonic acid. Compounds of formula (I) having at least one acidic group can form salts with, for example, bases, such as mineral salts, such as alkali metal or alkaline earth metal salts, such as sodium, potassium or magnesium salts, or salts with ammonia 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 is in free form, oxidized form as an N-oxide, covalently hydrated form, or salt form, for example, an agrochemically usable or agrochemically acceptable salt form. The N-oxide is an oxidized form of a tertiary amine or an oxidized form of a nitrogen-containing heteroaromatic compound. 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 compound of formula (I) according to the present invention also includes a hydrate, which may be formed during salt formation.

[0038] In further embodiments, the compound of formula (I) according to the present invention is R 1a , R 1b and R 1c Hydrogen, 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 and C 1-6 Compounds are provided that are independently selected from alkoxys. In certain embodiments, 1a , R 1band R 1c is hydrogen and C 1-6 ~Can be selected independently of alkyl. In another specific embodiment, R 1a and R 1c It can be hydrogen, and 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, and NHC(O)C 1-6 It is selected independently of alkyl.

[0039] In further embodiments, the compound of formula (I) according to the present invention is 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, 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, 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 halogen, hydroxyl, and CN, preferably R 2 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Selected independently of alkoxy, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Each alkoxy group may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxyl, and N, more preferably R 2 is hydrogen, halogen, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Compounds are provided that are independently selected from alkyl and CN.

[0040] In further embodiments, the compound of formula (I) according to the present invention is R 3 These are hydroxy, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, amino, C 1-6 Alkylamino, diC 1-6 -Alkylamino and C 3-6 Selected from cycloalkylaminos, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, amino, C1-6 Alkylamino, diC 1-6 -Alkylamino and C 3-6 Compounds are provided in which each of the cycloalkylamino groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxyl, and CN. More preferably, R 3 These are hydroxy, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Selected from alkoxycarbonyls, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Each alkoxycarbonyl group may be optionally substituted with one substituent selected from halogen, hydroxyl, and CN.

[0041] In a further embodiment, the compound of formula (I) according to the present invention comprises four A 2 CR 2 and A 3 A compound is provided in which N is present.

[0042] In further embodiments, the compound of formula (I) according to the present invention is: [ka] teeth, [ka] Preferably, three A 2 CR 2 and A 3 CR 3 A compound is provided.

[0043] In further embodiments, the compound of formula (I) according to the present invention is: [ka] teeth, [ka] Preferably, three A 2 CR 2 and A 3 CR 3 A compound is provided.

[0044] In a further embodiment, the compound of formula (I) according to the present invention comprises four A 2 CR 2 and A 3 CR 3 A compound is provided.

[0045] In further embodiments, the compound of formula (I) according to the present invention is 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 and C 1-6 Selected from alkoxy, 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 and C 1-6 Each alkoxy 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 1-6Selected from alkoxy, 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, preferably 1 substituent, independently selected from halogens and CN. A 3 and R 4 The compounds provided are those which together form a ring, preferably a 5-8 membered heterocycle, more preferably a 6 membered heterocycle.

[0046] In a further embodiment, the compound of formula (I) according to the present invention is A 3 CR 3 And R 3 and R 4 Together, they form a ring, preferably a 5-8 membered heterocycle, preferably a 6 membered heterocycle, more preferably the following formula (I): [ka] A compound is provided that forms one of the rings W1, W2, or W3 described in the compound.

[0047] The carbon and / or nitrogen atoms forming the ring (W1, W2, or W3) are, in particular, R 3’ It can be substituted with R 3’ is hydrogen, C 1-6 Alkyl, C 3-6 Cycloalkyl, hydroxy, C 1-6 Alkoxy and C 1-6 Selected from alkoxycarbonyls, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy and C 1-6 Each alkoxycarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN. More preferably, R 3’ is hydrogen, C 1-6Alkyl, hydroxy, C 1-6 Alkoxy and C 1-6 Selected from alkoxycarbonyls, C 1-6 Alkyl, C 1-6 Alkoxy and C 1-6 Each alkoxycarbonyl group may be optionally substituted with one substituent selected from halogens and CN. For example, the compounds of formula (I-W3) may be as follows: [ka]

[0048] In preferred embodiments, the compounds of formulas (W1), (W2), and (W3) may be as described below. [ka]

[0049] The carbon and / or nitrogen atoms forming the ring (W1, W2, or W3) are, in particular, R 3’ It can be substituted with R 3’ is hydrogen, C 1-6 Alkyl, hydroxy, C 1-6 Alkoxy, C 1-6 Alkoxycarbonyl and C 3-6 Selected from cycloalkyl, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxycarbonyl and C 3-6 Each cycloalkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN. More preferably, R 3’ is hydrogen, C 1-6 Alkyl, hydroxy, C 1-6 Alkoxy and C 1-6 Selected from alkoxycarbonyls, C 1-6 Alkyl C 1-6 Alkoxy and C 1-6Each alkoxycarbonyl group may be optionally substituted with one substituent selected from halogens and CN. For example, the compounds of formula (I-W3) may be as follows: [ka]

[0050] In further embodiments, the compound of formula (I) according to the present invention is 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 Compounds are provided, selected from alkyl groups, each of which may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN.

[0051] In a particular embodiment, the formula (I-W1, I-W2, or I-W3) according to the present invention [ka] , moreover, [ka] (In the formula, Z is O, A 1 N is, R 1a and R 1c is hydrogen, and 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, and NHC(O)C 1-6 Selected from alkyl groups, Two A's2 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-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkoxycarbonyl and C 1-6 Independently selected from alkylsulfonyls, 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 Alkoxycarbonyl and C 1-6 Each alkylsulfonyl 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, C 1-6 Alkyl, C 1-6 Alkoxy, C1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl and C 1-6 Alkoxy-C 1-6 Each alkoxy group may be substituted with 1 to 3 substituents independently selected from halogen, hydroxyl, and CN, preferably 1 substituent, preferably R 2 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxycarbonyl and C 1-6 Alkoxy-C 1-6 Selected independently of alkyl, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxycarbonyl and C 1-6 Alkoxy-C 1-6 Each alkyl group may be optionally substituted with 1 to 3 substituents, preferably 1 substituent, independently selected from halogens, hydroxyls, and CNs. R 3’ is hydrogen, C 1-6 Alkyl and C 3-6 Selected from cycloalkyl, C 1-6 Alkyl and C 3-6 Each cycloalkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN. 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 and C 1-6 Alkyl C 1-6 Selected from alkoxyaminos, each of the groups may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN, preferably R 5 C1-6 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, each of which may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN.) The compound is provided.

[0052] In further embodiments, the compounds according to the present invention are selected from the following: Methyl N-[5-[6-[2,3-dihydrobenzofuran-7-yl(methyl)carbamoyl]-8-methylimidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-carbonyl)-8-methylimidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[2,3-dihydrobenzofuran-7-yl(methyl)carbamoyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(7-fluoro-2,3-dihydro-1,4-benzoxazine-4-carbonyl)-8-methylimidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(5-methoxy-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl 1-[3-[6-(methoxycarbonylamino)-3-pyridyl]imidazo[1,2-a]pyridine-6-carbonyl]-3,4-dihydro-2H-quinoline-5-carboxylate, Methyl N-[5-[6-(3-methyl-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(8-fluoro-7-methyl-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[(2-chloro-5-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl 1-[3-[6-(methoxycarbonylamino)-3-pyridyl]imidazo[1,2-a]pyridine-6-carbonyl]-3,4-dihydro-2H-quinoline-3-carboxylate, Methyl N-[5-[6-[(3-fluoro-2-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(5-fluoro-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(5-chloroindoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(7-fluoro-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(6-chloro-8-fluoro-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(5,7-difluoroindoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(6-bromo-5-fluoro-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[(2-chloro-4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(5,6-difluoro-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[(2-fluoro-4-methylphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(7-methylsulfonyl-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(6-fluoro-3-hydroxy-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[(6-chloropyridazine-3-yl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(6,7-difluoro-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(5-methyl-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(5-fluoro-6-methyl-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[4-(2-methoxyethyl)-3,4-dihydro-2H-quinoline-1-carbonyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[(4-fluoro-2-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(6-methyl-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(3-methoxy-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl 1-[3-[6-(methoxycarbonylamino)-3-pyridyl]imidazo[1,2-a]pyridine-6-carbonyl]-3,4-dihydro-2H-quinoline-4-carboxylate, Methyl N-[5-[6-[6-(difluoromethoxy)-3,4-dihydro-2H-quinoline-1-carbonyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Ethyl 6-fluoro-1-[3-[6-(methoxycarbonylamino)-3-pyridyl]imidazo[1,2-a]pyridine-6-carbonyl]-3,4-dihydro-2H-quinoline-3-carboxylate, Methyl N-[5-[6-(7-methyl-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[(6-fluoro-2-pyridyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(6-methoxy-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[(2,3-dichlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[methyl-(5-methyl-2-pyridyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(5,7-dimethoxy-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl 1-[3-[6-(methoxycarbonylamino)-3-pyridyl]imidazo[1,2-a]pyridine-6-carbonyl]-3,4-dihydro-2H-1,6-naphthyridine-5-carboxylate, Methyl N-[5-[6-(3-hydroxy-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[methyl-(4-methylpyrimidine-2-yl)carbamoyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl 1-[3-[6-(methoxycarbonylamino)-3-pyridyl]imidazo[1,2-a]pyridine-6-carbonyl]-3,4-dihydro-2H-quinoline-7-carboxylate, Methyl 2-[[3-[6-(methoxycarbonylamino)-3-pyridyl]imidazo[1,2-a]pyridine-6-carbonyl]-methyl-amino]benzoate, Methyl N-[5-[6-[(5-chloro-2-methylphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(6-chloro-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[methyl-(2,3,4-trifluorophenyl)carbamoyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(8-fluoro-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(4-cyclopropyl-6-fluoro-2,3-dihydroquinoxaline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(6-methoxyindoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[(4-chloro-2-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[(2,5-difluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(6-methylsulfonyl-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(7-methoxy-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(6,7-dimethoxy-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[5-(difluoromethoxy)-3,4-dihydro-2H-quinoline-1-carbonyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl 2-[ethyl-[3-[6-(methoxycarbonylamino)-3-pyridyl]imidazo[1,2-a]pyridine-6-carbonyl]amino]benzoate, Methyl N-[5-[6-[(2-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[(5-chloro-2-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(6-fluoro-5-methoxy-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(7-fluoro-6-methoxy-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(6-fluoro-7-methoxy-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(5-fluoroindoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-(6-fluoro-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[(4-fluoro-2,6-diiodophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[(5-chloro-2-pyridyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[(5-cyanopyrazine-2-yl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[(4-methoxy-2-pyridyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[6-[(5-fluoro-2-pyridyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate, Methyl N-[4-[6-[(5-chloro-2-pyridyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]phenyl]carbamate, Methyl N-[4-[6-[(2,6-difluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]phenyl]carbamate, Methyl N-[4-[6-[methyl-(2-methyl-3-pyridyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate, Methyl N-[4-[6-[(2,5-difluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]phenyl]carbamate, Methyl N-[4-[6-[(2-isopropylphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]phenyl]carbamate, Methyl N-[4-[6-[methyl(o-tolyl)carbamoyl]imidazo[1,2-a]pyridine-3-yl]phenyl]carbamate, Methyl N-[4-[6-[(2,4-difluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]phenyl]carbamate, and Methyl N-[4-[6-[(2,4-dichlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]phenyl]carbamate.

[0053] 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.

[0054] The compounds listed in Tables 1.1 to 1.27, 2.1 to 2.45, 3.1 to 3.55, and 4.1 to 4.24 below exemplify the compounds of the present invention.

[0055] Table 1.1 shows equation (Ia) [ka] (In the formula, Z is O, R 1a H is R 1b H is R 1c H is R 3 It is methoxy, and R 5 It is methyl, R 4 , A 2c , A 2b , A 2a and A 1 The value of is defined in Table Z.1 below.) The compound is provided.

[0056] (Continued in Table Z.1) Each of Tables 1.2 to 1.27 is given by equation (Ia) (where Z, R 1a , R 1b , R 1c , R 3 and R 5 This document discloses the individual compounds (specifically defined in Tables 1.2 to 1.27), and for these, R 4 , A 2c , A 2b , A 2aand A 1 Table Z.1, which provides a specific definition, is referenced.

[0057] [Table 1-1]

[0058] [Table 1-2]

[0059] [Table 1-3]

[0060] [Table 1-4]

[0061] [Table 1-5]

[0062] [Table 1-6]

[0063] [Table 1-7]

[0064] [Table 1-8]

[0065] [Table 1-9]

[0066] [Table 1-10]

[0067] Table 1-11

[0068] Table 1-12

[0069] Table 1-13

[0070] Table 1-14

[0071] Table 1-15

[0072] Table 1-16

[0073] Table 1-17

[0074] Table 1-18

[0075] Table 1-19

[0076] Table 1-20

[0077] [Table 1-21]

[0078] [Table 1-22]

[0079] [Table 1-23]

[0080] [Table 1-24]

[0081] [Table 1-25]

[0082] [Table 1-26]

[0083] [Table 1-27]

[0084] Table 1.2: This table shows that Z is O and R 1a H is R 1b H is R 1c H is R 3 is methoxy, and R 5 is methoxy, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0085] Table 1.3: This table shows that Z is O and R 1a H is R 1b H is R 1c H is R 3 is methoxy, and R 5 It is cyclopropyl, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0086] Table 1.4: This table shows that Z is O and R 1a H is R 1b is methyl, R 1c H is R 3 is methoxy, and R 5 is methyl, R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0087] Table 1.5: This table shows that Z is O and R 1a H is R 1b is methyl, and R 1c H is R 3 is methoxy, and R 5 is methoxy, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0088] Table 1.6: This table shows that Z is O and R 1a H is R 1b is methyl, and R 1c H is R 3 is methoxy, and R 5 It is cyclopropyl, and R 4 , A 2c , A2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0089] Table 1.7: This table shows that Z is O and R 1a H is R 1b is methoxymethyl, and R 1c H is R 3 is methoxy, and R 5 is methyl, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0090] Table 1.8: This table shows that Z is O and R 1a H is R 1b is methoxymethyl, and R 1c H is R 3 is methoxy, and R 5 is methoxy, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0091] Table 1.9: This table shows that Z is O and R 1a H is R 1b is methoxymethyl, and R 1c H is R 3 is methoxy, and R 5 It is cyclopropyl, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0092] Table 1.10: This table shows that Z is O and R1a H is R 1b H is R 1c H is R 3 is fluoro, R 5 is methoxy, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0093] Table 1.11: This table shows that Z is O and R 1a H is R 1b H is R 1c H is R 3 is fluoro, R 5 is methoxy, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0094] Table 1.12: This table shows that Z is O and R 1a H is R 1b H is R 1c H is R 3 is fluoro, R 5 It is cyclopropyl, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0095] Table 1.13: This table shows that Z is O and R 1a H is R 1b is methyl, and R 1c H is R 3 is fluoro, R 5 is methyl, and R 4 , A 2c , A 2b , A 2aand A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0096] Table 1.14: This table shows that Z is O and R 1a H is R 1b is methyl, and R 1c H is R 3 is fluoro, R 5 is methoxy, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0097] Table 1.15: This table shows that Z is O and R 1a H is R 1b is methyl, and R 1c H is R 3 is fluoro, R 5 It is cyclopropyl, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0098] Table 1.16: This table shows that Z is O and R 1a H is R 1b is methoxymethyl, and R 1c H is R 3 is fluoro, R 5 is methyl, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0099] Table 1.17: This table shows that Z is O and R 1a H is R 1bis methoxymethyl, and R 1c H is R 3 is fluoro, R 5 is methoxy, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0100] Table 1.18: This table shows that Z is O and R 1a H is R 1b is methoxymethyl, and R 1c H is R 3 is fluoro, R 5 It is cyclopropyl, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0101] Table 1.19: This table shows that Z is O and R 1a H is R 1b H is R 1c H is R 3 That is chloro, and R 5 is methoxy, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0102] Table 1.20: This table shows that Z is O and R 1a H is R 1b H is R 1c H is R 3 That is chloro, and R 5 is methoxy, and R 4 , A 2c , A 2b , A 2a and A 1We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0103] Table 1.21: This table shows that Z is O and R 1a H is R 1b H is R 1c H is R 3 That is chloro, and R 5 It is cyclopropyl, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0104] Table 1.22: This table shows that Z is O and R 1a H is R 1b is methyl, and R 1c H is R 3 That is chloro, and R 5 is methyl, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0105] Table 1.23: This table shows that Z is O and R 1a H is R 1b is methyl, and R 1c H is R 3 That is chloro, and R 5 is methoxy, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0106] Table 1.24: This table shows that Z is O and R 1a H is R 1b is methyl, and R 1c H is R3 That is chloro, and R 5 It is cyclopropyl, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0107] Table 1.25: This table shows that Z is O and R 1a H is R 1b is methoxymethyl, and R 1c H is R 3 That is chloro, and R 5 is methyl, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0108] Table 1.26: This table shows that Z is O and R 1a H is R 1b is methoxymethyl, and R 1c H is R 3 That is chloro, and R 5 is methoxy, and R 4 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0109] Table 1.27: This table shows that Z is O and R 1a H is R 1b is methoxymethyl, and R 1c H is R 3 That is chloro, and R 5 It is cyclopropyl, and R 4 , A 2c , A 2b , A 2a and A 1We disclose a specific compound of formula (Ia) whose value is as defined in Table Z.1.

[0110] The compounds listed in Tables 2.1 to 2.45 below are examples of compounds of the present invention.

[0111] Table 2.1 shows equation (Ib) [ka] (In the formula, Z is O and A 3 and R 4 Together, they form the indicated ring. R 1a H is R 1b H is R 1c H is R 5 It is methyl, RA 2c , A 2b , A 2a and A 1 (The value of is defined in Table Z.2 below.) The compound is provided.

[0112] (Continued in Table Z.2) Each of Tables 2.1 to 2.45 is an expression (Ib), (Ic), (Id), (Ie), and (If) (where R 1a , R 1b , R 1c and R 5 This document discloses the individual compounds (specifically defined in Tables 2.1 to 2.45), and for these, A 2c , A 2b , A 2a and A 1 Table Z.2, which provides a specific definition, is referenced.

[0113] [Table 2-1]

[0114] [Table 2-2]

[0115] [Table 2-3]

[0116] [Table 2-4]

[0117] Table 2.2: This table shows that Z is O and R 1a H is R 1b H is R 1c H is R 5 is methoxy, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ib) whose value is as defined in Table Z.2.

[0118] Table 2.3: This table shows that Z is O and R 1a H is R 1b H is R 1c H is R 5 is cyclopropyl, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ib) whose value is as defined in Table Z.2.

[0119] Table 2.4: This table shows that Z is O and R 1a H is R 1b is methyl, and R 1c H is R 5 is methyl, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ib) whose value is as defined in Table Z.2.

[0120] Table 2.5: This table shows that Z is O and R 1a H is R 1b is methyl, and R1c H is R 5 is methoxy, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ib) whose value is as defined in Table Z.2.

[0121] Table 2.6: This table shows that Z is O and R 1a H is R 1b is methyl, and R 1c H is R 5 is cyclopropyl, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ib) whose value is as defined in Table Z.2.

[0122] Table 2.7: This table shows that Z is O and R 1a H is R 1b is methoxymethyl, and R 1c H is R 5 is methyl, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ib) whose value is as defined in Table Z.2.

[0123] Table 2.8: This table shows that Z is O and R 1a H is R 1b is methoxymethyl, and R 1c H is R 5 is methoxy, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ib) whose value is as defined in Table Z.2.

[0124] Table 2.9: This table shows that Z is O and R 1a H is R 1b is methoxymethyl, and R 1c H is R5 is cyclopropyl, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ib) whose value is as defined in Table Z.2.

[0125] Table 2.10 shows equation (Ic) [ka] (In the formula, Z is O and R 3 and R 4 Together, they form the indicated ring. R 1a H is R 1b H is R 1c H is R 5 It is methyl, A 2c , A 2b , A 2a and A 1 The value is as defined in Table Z.2 above.) The compound is provided.

[0126] Table 2.11: This table shows that Z is O and R 1a H is R 1b H is R 1c H is R 5 is methoxy, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ic) whose value is as defined in Table Z.2.

[0127] Table 2.12: This table shows that Z is O and R 1a H is R 1b H is R 1c H is R 5 is cyclopropyl, and A 2c , A 2b , A 2a and A 1Discloses a specific compound of formula (Ic) where the value of

[0128] Table 2.13: This table shows that Z is O, R 1a is H, R 1b is methyl, R 1c is H, R 5 is methyl, A 2c A 2b A 2a and A 1 Discloses a specific compound of formula (Ic) where the value of

[0129] Table 2.14: This table shows that Z is O, R 1a is H, R 1b is methyl, R 1c is H, R 5 is methoxy, A 2c A 2b A 2a and A 1 Discloses a specific compound of formula (Ic) where the value of

[0130] Table 2.15: This table shows that Z is O, R 1a is H, R 1b is methyl, R 1c is H, R 5 is cyclopropyl, A 2c A 2b A 2a and A 1 Discloses a specific compound of formula (Ic) where the value of

[0131] Table 2.16: This table shows that Z is O, R 1a is H, R 1b is methoxymethyl, R 1c is H, R 5 is methoxy, A 2c A 2b A 2a and A 1We disclose a specific compound of formula (Ic) whose value is as defined in Table Z.2.

[0132] Table 2.17: This table shows that Z is O and R 1a H is R 1b is methoxymethyl, and R 1c H is R 5 is methoxy, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ic) whose value is as defined in Table Z.2.

[0133] Table 2.18: This table shows that Z is O and R 1a H is R 1b is methoxymethyl, and R 1c H is R 5 , A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ic) whose value is as defined in Table Z.2.

[0134] Table 2.19 shows formula (Id) [ka] (In the formula, Z is O and R 3 and R 4 Together, they form the indicated ring. R 1a H is R 1b H is R 1c H is R 5 It is methyl, A 2c , A 2b , A 2a and A 1 The value is as defined in Table Z.2 above.) The compound is provided.

[0135] Table 2.20: This table shows that Z is O and R 1a H is R1b H is R 1c H is R 5 is methoxy, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Id) whose value is as defined in Table Z.2.

[0136] Table 2.21: This table shows that Z is O and R 1a H is R 1b H is R 1c H is R 5 is cyclopropyl, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Id) whose value is as defined in Table Z.2.

[0137] Table 2.22: This table shows that Z is O and R 1a H is R 1b is methyl, and R 1c H is R 5 is methyl, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Id) whose value is as defined in Table Z.2.

[0138] Table 2.23: This table shows that Z is O and R 1a H is R 1b is methyl, and R 1c H is R 5 is methoxy, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Id) whose value is as defined in Table Z.2.

[0139] Table 2.24: This table shows that Z is O and R 1a H is R 1b is methyl, and R 1cis H, and R 5 is cyclopropyl, and A 2c A 2b A 2a and A 1 the values of are as defined in Table Z.2, discloses a specific compound of formula (Id).

[0140] Table 2.25: This table shows that Z is O, and R 1a is H, and R 1b is methoxymethyl, and R 1c is H, and R 5 is methyl, and A 2c A 2b A 2a and A 1 the values of are as defined in Table Z.2, discloses a specific compound of formula (Id).

[0141] Table 2.26: This table shows that Z is O, and R 1a is H, and R 1b is methoxymethyl, and R 1c is H, and R 5 is methoxy, and A 2c A 2b A 2a and A 1 the values of are as defined in Table Z.2, discloses a specific compound of formula (Id).

[0142] Table 2.27: This table shows that R 1a is H, and R 1b is methoxymethyl, and R 1c is H, and R 5 is cyclopropyl, and A 2c A 2b A 2a and A 1 the values of are as defined in Table Z.2, discloses a specific compound of formula (Id).

[0143] Table 2.28 is for formula (Ie)

Chemical formula

[0144] Table 2.29: This table shows that Z is O and R 1a H is R 1b H is R 1c H is R 5 is methoxy, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ie) whose value is as defined in Table Z.2.

[0145] Table 2.30: This table shows that Z is O and R 1a H is R 1b H is R 1c H is R 5 is cyclopropyl, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ie) whose value is as defined in Table Z.2.

[0146] Table 2.31: This table shows that Z is O and R 1a H is R 1b is methyl, and R 1c H is R 5 is methyl, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ie) whose value is as defined in Table Z.2.

[0147] Table 2.32: This table shows that Z is O and R 1a H is R 1b is methyl, and R 1c H is R 5 is methoxy, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ie) whose value is as defined in Table Z.2.

[0148] Table 2.33: This table shows that Z is O and R 1a H is R 1b is methyl, and R 1c H is R 5 is cyclopropyl, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ie) whose value is as defined in Table Z.2.

[0149] Table 2.34: This table shows that Z is O and R 1a H is R 1b is methoxymethyl, and R 1c H is R 5 is methyl, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ie) whose value is as defined in Table Z.2.

[0150] Table 2.35: This table shows that Z is O and R 1a H is R 1b is methoxymethyl, and R 1c H is R 5 is methoxy, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ie) whose value is as defined in Table Z.2.

[0151] Table 2.36: This table is R 1a H is R 1b is methoxymethyl, and R 1c H is R 5 is cyclopropyl, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (Ie) whose value is as defined in Table Z.2.

[0152] Table 2.37 shows the formula (If) [ka] (In the formula, Z is O and R 3 and R 4 Together, they form the indicated ring. R 1a H is R 1b H is R 1c H is R 5 It is methyl, A 2c , A 2b , A 2a and A 1 The value is as defined in Table Z.2 above.) The compound is provided.

[0153] Table 2.38: This table shows that Z is O and R 1a H is R 1b H is R 1c H is R 5 is methoxy, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (If) whose value is as defined in Table Z.2.

[0154] Table 2.39: This table shows that Z is O and R 1a H is R 1b H is R 1c H is R 5 is cyclopropyl, and A2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (If) whose value is as defined in Table Z.2.

[0155] Table 2.40: This table shows that Z is O and R 1a H is R 1b is methyl, and R 1c H is R 5 is methyl, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (If) whose value is as defined in Table Z.2.

[0156] Table 2.41: This table shows that Z is O and R 1a H is R 1b is methyl, and R 1c H is R 5 is methoxy, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (If) whose value is as defined in Table Z.2.

[0157] Table 2.42: This table shows that Z is O and R 1a H is R 1b is methyl, and R 1c H is R 5 is cyclopropyl, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (If) whose value is as defined in Table Z.2.

[0158] Table 2.43: This table shows that Z is O and R 1a H is R 1b is methoxymethyl, and R 1c H is R 5 is methyl, and A 2c , A 2b , A2a and A 1 We disclose a specific compound of formula (If) whose value is as defined in Table Z.2.

[0159] Table 2.44: This table shows that Z is O and R 1a H is R 1b is methoxymethyl, and R 1c H is R 5 is methoxy, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (If) whose value is as defined in Table Z.2.

[0160] Table 2.45: This table shows that Z is O and R 1a H is R 1b is methoxymethyl, and R 1c H is R 5 is cyclopropyl, and A 2c , A 2b , A 2a and A 1 We disclose a specific compound of formula (If) whose value is as defined in Table Z.2.

[0161] The compounds listed in Tables 3.1 to 3.55 below are examples of compounds of the present invention.

[0162] Table 3.1: This table shows the formula (Ig) [ka] (In the formula, Z is O and R 1a H is R 1c H is A 2c CH is, R 4 It is CH3, and R 1b , A 1 , A 2b , R 5 (This is defined in Table 3 below.) The following disclosure concerns specific compounds.

[0163] [Table 3-1]

[0164] [Table 3-2]

[0165] [Table 3-3]

[0166] [Table 3-4]

[0167] [Table 3-5]

[0168] Table 3.2: This table shows that Z is O and R 1a H is R 1c H is A 2c CH is, R 4 And R is CH2CH3, 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0169] Table 3.3: This table shows that Z is O and R 1a H is R 1c H is A 2c CH is, R 4 is CH2OCH3, and R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0170] Table 3.4: This table shows that Z is O and R 1a H is R1c H is A 2c CH is, R 4 And R is CH2CH2OCH3, 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0171] Table 3.5: This table shows that Z is O and R 1a H is R 1c H is A 2c CH is, R 4 CH2CN is, R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0172] Table 3.6: This table shows that Z is O and R 1a H is R 1c H is A 2c This is CCH3, and R 4 CH3 is, R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0173] Table 3.7: This table shows that Z is O and R 1a H is R 1c H is A 2c This is CCH3, and R 4 And R is CH2CH3, 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0174] Table 3.8: This table shows that Z is O and R 1a H is R 1c H is A 2c This is CCH3, and R4 is CH2OCH3, and R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0175] Table 3.9: This table shows that Z is O and R 1a H is R 1c H is A 2c This is CCH3, and R 4 And R is CH2CH2OCH3, 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0176] Table 3.10: This table shows that Z is O and R 1a H is R 1c H is A 2c This is CCH3, and R 4 CH2CN is, R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0177] Table 3.11: This table shows that Z is O and R 1a H is R 1c H is A 2c This is CCH2CH3, and R 4 CH3 is, R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0178] Table 3.12: This table shows that Z is O and R 1a H is R 1c H is A 2c This is CCH2CH3, and R 4 And R is CH2CH3, 1b, A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0179] Table 3.13: This table shows that Z is O and R 1a H is R 1c H is A 2c This is CCH2CH3, and R 4 is CH2OCH3, and R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0180] Table 3.14: This table shows that Z is O and R 1a H is R 1c H is A 2c This is CCH2CH3, and R 4 And R is CH2CH2OCH3, 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0181] Table 3.15: This table shows that Z is O and R 1a H is R 1c H is A 2c This is CCH2CH3, and R 4 CH2CN is, R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0182] Table 3.16: This table shows that Z is O and R 1a H is R 1c H is A 2c CF is R 4 CH3 is, R 1b , A 1 , A 2b , R5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0183] Table 3.17: This table shows that Z is O and R 1a H is R 1c H is A 2c CF is R 4 And R is CH2CH3, 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0184] Table 3.18: This table shows that Z is O and R 1a H is R 1c H is A 2c CF is R 4 is CH2OCH3, and R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0185] Table 3.19: This table shows that Z is O and R 1a H is R 1c H is A 2c CF is R 4 And R is CH2CH2OCH3, 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0186] Table 3.20: This table shows that Z is O and R 1a H is R 1c H is A 2c CF is R 4 CH2CN is, R 1b , A 1 , A 2b , R 5We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0187] Table 3.21: This table shows that Z is O and R 1a H is R 1c H is A 2c CCl is R 4 CH3 is, R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0188] Table 3.22: This table shows that Z is O and R 1a H is R 1c H is A 2c CCl is R 4 And R is CH2CH3, 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0189] Table 3.23: This table shows that Z is O and R 1a H is R 1c H is A 2c CCl is R 4 is CH2OCH3, and R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0190] Table 3.24: This table shows that Z is O and R 1a H is R 1c H is A 2c CCl is R 4 And R is CH2CH2OCH3, 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0191] Table 3.25: This table shows that Z is O and R 1a H is R 1c H is A 2c CCl is R 4 This is CH2CNd, and R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0192] Table 3.26: This table shows that Z is O and R 1a H is R 1c H is A 2c CBr is R 4 CH3 is, R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0193] Table 3.27: This table shows that Z is O and R 1a H is R 1c H is A 2c CBr is R 4 And R is CH2CH3, 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0194] Table 3.28: This table shows that Z is O and R 1a H is R 1c H is A 2c CBr is R 4 is CH2OCH3, and R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0195] Table 3.29: This table shows that Z is O and R 1a H is R 1c H is A 2c CBr is R 4 And R is CH2CH2OCH3, 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0196] Table 3.30: This table shows that Z is O and R 1a H is R 1c H is A 2c CBr is R 4 CH2CN is, R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0197] Table 3.31: This table shows that Z is O and R 1a H is R 1c H is A 2c CCN is R 4 CH3 is, R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0198] Table 3.32: This table shows that Z is O and R 1a H is R 1c H is A 2c CCN is R 4 And R is CH2CH3, 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0199] Table 3.33: This table shows that Z is O and R 1a H is R1c H is A 2c CCN is R 4 is CH2OCH3, and R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0200] Table 3.34: This table shows that Z is O and R 1a H is R 1c H is A 2c CCN is R 4 And R is CH2CH2OCH3, 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0201] Table 3.35: This table shows that Z is O and R 1a H is R 1c H is A 2c CCN is R 4 CH2CN is, R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0202] Table 3.36: This table shows that Z is O and R 1a H is R 1c H is A 2c COCH3 is R 4 CH3 is, R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0203] Table 3.37: This table shows that Z is O and R 1a H is R 1c H is A 2c COCH3 is R4 And R is CH2CH3, 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0204] Table 3.38: This table shows that Z is O and R 1a H is R 1c H is A 2c COCH3 is R 4 is CH2OCH3, and R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0205] Table 3.39 shows that Z is O, and R 1a H is R 1c H is A 2c COCH3 is R 4 And R is CH2CH2OCH3, 1b , A 1 , A 2b , R 5 This provides 192 compounds E-39.001 to E-39.192 of formula (Ig), as defined in Table Z.3.

[0206] Table 3.40: This table shows that Z is O and R 1a H is R 1c H is A 2c COCH3 is R 4 CH2CN is, R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0207] Table 3.41: This table shows that Z is O and R 1a H is R 1c H is A 2c This is COCH2CH3, and R 4CH3 is, R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0208] Table 3.42: This table shows that Z is O and R 1a H is R 1c H is A 2c This is COCH2CH3, and R 4 And R is CH2CH3, 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0209] Table 3.43: This table shows that Z is O and R 1a H is R 1c H is A 2c This is COCH2CH3, and R 4 is CH2OCH3, and R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0210] Table 3.44: This table shows that Z is O and R 1a H is R 1c H is A 2c This is COCH2CH3, and R 4 And R is CH2CH2OCH3, 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0211] Table 3.45: This table shows that Z is O and R 1a H is R 1c H is A 2c This is COCH2CH3, and R 4 CH2CN is, R 1b, A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0212] Table 3.46: This table shows that Z is O and R 1a H is R 1c H is A 2c This is COCH2CH2OCH3, and R 4 CH3 is, R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0213] Table 3.47: This table shows that Z is O and R 1a H is R 1c H is A 2c This is COCH2CH2OCH3, and R 4 And R is CH2CH3, 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0214] Table 3.48: This table shows that Z is O and R 1a H is R 1c H is A 2c This is COCH2CH2OCH3, and R 4 is CH2OCH3, and R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0215] Table 3.49: This table shows that Z is O and R 1a H is R 1c H is A 2c This is COCH2CH2OCH3, and R 4 And R is CH2CH2OCH3, 1b , A1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0216] Table 3.50: This table shows that Z is O and R 1a H is R 1c H is A 2c This is COCH2CH2OCH3, and R 4 CH2CN is, R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0217] Table 3.51: This table shows that Z is O and R 1a H is R 1c H is A 2c COH is, R 4 CH3 is, R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0218] Table 3.52: This table shows that Z is O and R 1a H is R 1c H is A 2c COH is, R 4 And R is CH2CH3, 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0219] Table 3.53: This table shows that Z is O and R 1a H is R 1c H is A 2c COH is, R 4 is CH2OCH3, and R 1b , A 1 , A 2b , R 5We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0220] Table 3.54: This table shows that Z is O and R 1a H is R 1c H is A 2c COH is, R 4 And R is CH2CH2OCH3, 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0221] Table 3.55: This table shows that Z is O and R 1a H is R 1c H is A 2c COH is, R 4 CH2CN is, R 1b , A 1 , A 2b , R 5 We disclose specific compounds of formula (Ig), as defined in Table Z.3.

[0222] The compounds listed in Tables 4.1 to 4.24 below are examples of compounds of the present invention.

[0223] Table 4.1 shows formula (Ih) [ka] (In the formula, Z is O and A 3 and R 4 Together, they form the indicated ring. R 1b H is R 5 CH3 is, A 1 CH is, A 2a , A 2b , A 2c , A 3a , A 3b , A 3c (This is defined in Table Z.4 below.) The compound is provided.

[0224] Table 4-1

[0225] Table 4-2

[0226] Table 4-3

[0227] Table 4-4

[0228] Table 4-5

[0229] Table 4-6

[0230] Table 4-7

[0231] Table 4-8

[0232] Table 4-9

[0233] Table 4-10

[0234] Table 4-11

[0235] Table 4-12

[0236] Table 4-13

[0237] Table 4-14

[0238] Table 4-15

[0239] Table 4-16

[0240] Table 4-17

[0241] Table 4-18

[0242] Table 4-19

[0243] Table 4-20

[0244] Table 4-21

[0245] [Table 4-22]

[0246] [Table 4-23]

[0247] [Table 4-24]

[0248] [Table 4-25]

[0249] [Table 4-26]

[0250] Table 4.2: This table is R 1b H is R 5 CH3 is N, A1 is N, A 2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0251] Table 4.3: This table is R 1b H is R 5 A is methoxy, A1 is CH, and A 2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0252] Table 4.4: This table is R 1b H is R 5 A is methoxy, A1 is N, and A 2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0253] Table 4.5: This table is R 1b H is R 5 A is cyclopropyl, A1 is CH, and A 2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0254] Table 4.6: This table is R 1b H is R 5 A is cyclopropyl, A1 is N, and A 2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0255] Table 4.7: This table is R 1b H is R 5 A is CH2OCH3, A1 is CH, and A 2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0256] Table 4.8: This table is R 1b H is R 5 A is CH2OCH3, A1 is N, and A 2a, A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0257] Table 4.9: This table is R 1b CH3 is, R 5 A is CH3, A1 is CH, and A 2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0258] Table 4.10: This table is R 1b CH3 is, R 5 CH3 is N, A1 is N, A 2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0259] Table 4.11: This table is R 1b CH3 is, R 5 A is methoxy, A1 is CH, and A 2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0260] Table 4.12: This table is R 1b CH3 is, R 5 A is methoxy, A1 is N, and A 2a , A 2b , A 2c , A 3a , A 3b , A 3cWe disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0261] Table 4.13: This table is R 1b CH3 is, R 5 A is cyclopropyl, A1 is CH, and A 2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0262] Table 4.14: This table is R 1b CH3 is, R 5 A is cyclopropyl, A1 is N, and A 2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0263] Table 4.15: This table is R 1b CH3 is, R 5 A is CH2OCH3, A1 is CH, and A 2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0264] Table 4.16: This table is R 1b CH3 is, R 5 A is CH2OCH3, A1 is N, and A 2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0265] Table 4.17: This table is R 1b is CH2OCH3, and R 5 A is CH3, A1 is CH, and A 2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0266] Table 4.18: This table is R 1b is CH2OCH3, and R 5 CH3 is N, A1 is N, A 2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0267] Table 4.19: This table is R 1b is CH2OCH3, and R 5 A is methoxy, A1 is CH, and A 2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0268] Table 4.20: This table is R 1b is CH2OCH3, and R 5 A is methoxy, A1 is N, and A 2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0269] Table 4.21: This table is R 1b is CH2OCH3, and R 5 A is cyclopropyl, A1 is CH, and A2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0270] Table 4.22: This table is R 1b is CH2OCH3, and R 5 A is cyclopropyl, A1 is N, and A 2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0271] Table 4.23: This table is R 1b is CH2OCH3, and R 5 A is CH2OCH3, A1 is CH, and A 2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0272] Table 4.24: This table is R 1b is CH2OCH3, and R 5 A is CH2OCH3, A1 is N, and A 2a , A 2b , A 2c , A 3a , A 3b , A 3c We disclose specific compounds of formula (Ih), as defined in Table Z.4.

[0273] The compounds according to the present invention may have many advantages, including, in particular, favorable levels of biological activity for protecting plants from fungal diseases or excellent properties for use as pesticide active ingredients (e.g., high biological activity, favorable activity spectrum, increased safety profile, improved physicochemical properties, or improved biodegradability). The compounds according to the present invention have particularly favorable levels of biological activity for protecting plants from oomycetes such as Phytophthora, Plasmopara, and Pythium.

[0274] Compounds of formula (I) where Z is O can be produced as shown in the following schemes 1 to 19 (wherein unless otherwise specified, the definitions of each variable are as defined in the present invention).

[0275] The compound of formula (I) is mixed with the compound of formula (III), where X is chloro(Cl), bromo(Br), or iodine(I), in a suitable solvent such as dimethylformamide, dioxane, tetrahydrofuran, ethanol, or water, in the presence of a base such as Cs2CO3, K2CO3, or NaOtBu, and a suitable palladium catalyst such as tetrakistriphenylphosphine palladium, palladium dichloride, [1,1-bis(diphenylphosphine)ferrocene]dichloropalladium(II), palladium acetate, or bis(diphenylphosphine)palladium(II) chloride, and R 7 Hydrogen and C are independent of each other. 1-6 Alkyl or two R 7 together become C 3-8 It can be prepared by Suzuki cross-coupling with a compound of formula (III) that can form a cycloalkyl group. This transformation is shown in Scheme 1. [ka] Scheme 1

[0276] Compounds of formula (II), where X is Cl, Br, or I, can be prepared by reacting a compound of formula (IV), where X is Cl, Br, or I, with a compound of formula (V) and a coupling agent, such as N,N'-dicyclohexylcarbodiimide, bis(2-oxo-3-oxazolidinyl)phosphinate chloride, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, propylphosphonic anhydride, or cyanuryl chloride, and optionally a base such as triethylamine, ethyldiisopropylamine, or N-methylmorpholine. The amine of formula (V) is commercially available or can be synthesized using methods known to those skilled in the art. This conversion is shown in Scheme 2. [ka] Scheme 2

[0277] Compounds of formula (IV) where X is Cl, Br, or I are commercially available, or where X is Cl, Br, or I and R8 is C 1-6 The alkyl compound of formula (VI) can be prepared by saponifying it with a base such as NaOH or LiOH in a suitable solvent such as methanol, ethanol, or water at room temperature to reflux. This transformation is shown in Scheme 3. [ka] Scheme 3

[0278] Instead, the compound of formula (II) where X is Cl, Br or I, in a suitable solvent such as tetrahydrofuran or toluene, in the presence of trimethylaluminum or bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]octane adduct, where X is Cl, Br or I, and R 8 C 1-6These compounds can be prepared directly by reacting the alkyl compound of formula (VI) with the compound of formula (V). These conversions are described in the literature (see, for example, Weinreb, S. et al. Tetrahedron Lett. 1977, 48, 4171; Woodward, S. et al. Tetrahedron Letters 2006, 47, 5767; Woodward S. et al. Org. Process Res. Dev., 2015, 19, 831). This conversion is shown in Scheme 4. [ka] Scheme 4

[0279] X is Cl, Br, or I, and R 8 C 1-6 Compounds of formula (VI) that are alkyl are commercially available, or are prepared in a suitable solvent such as dichloromethane, chloroform, tetrahydrofuran, or acetonitrile, R 8 C 1-6 It can be prepared by reacting an alkyl compound of formula (VII) with a halogenating agent such as N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, or bromine. This transformation is shown in Scheme 5. [ka] Scheme 5

[0280] R 8 C 1-6 A compound of formula (VII) which is alkyl is commercially available, or, in the presence of a catalyst such as [1,1'-bis-(diphenylphosphin)-ferrocene]-dichloropalladium(II) and optionally a base such as triethylamine, a compound of formula (VIII) where X is Cl, Br or I, carbon monoxide and alcohol R 8 OH (in the formula, R 8 C 1-6 It can be prepared by reaction with an alkyl group. This transformation is shown in Scheme 6. [ka] Scheme 6

[0281] The compound of formula (VIII) is commercially available, or in a solvent such as water, ethanol, acetone, or acetonitrile, it is mixed with the compound of formula (IX) where X is Cl, Br, or I, and the compound of formula (X) where X is Cl, Br, or I, or where X is Cl, Br, or I, and R 9 C 1-6 Alkyl or two R 9 together become C 3-8 It can be prepared by reacting the corresponding acetal of formula (XI), which can form a cycloalkyl. The reaction outcome can be improved by using a base such as sodium bicarbonate or potassium carbonate, or by using an acid such as p-toluenesulfonic acid or hydrogen bromide. Furthermore, this conversion is R 8 C 1-6 From the alkyl compound of formula (XII), R 8 C 1-6 This can be used to prepare the alkyl compound of formula (VII) and to prepare the compound of formula (XIII) from the compound of formula (XIV). These transformations are shown in Scheme 7. [ka] [ka] Scheme 7

[0282] Compounds of formula (IX) where X is Cl, Br, or I, R 8 C 1-6 The alkyl compounds of formula (XII) and formula (XIV) are prepared by known methods or are commercially available.

[0283] Alternatively, the compound of formula (I) can be prepared by reacting the compound of formula (XV) with the compound of formula (V) and a coupling agent, such as N,N'-dicyclohexylcarbodiimide, bis(2-oxo-3-oxazolidinyl)phosphinate chloride, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, propylphosphonic anhydride, or cyanuryl chloride, and optionally a base such as triethylamine, ethyldiisopropylamine, or N-methylmorpholine, in a suitable solvent such as ethyl acetate, dimethylformamide, tetrahydrofuran, or dichloromethane. This conversion is shown in Scheme 8. [ka] Scheme 8

[0284] Compound (XV) of formula (XV) can be prepared by using a base such as NaOH or LiOH in a suitable solvent such as methanol, ethanol, or water at room temperature to reflux temperature. 8 C 1-6 It can be prepared by saponifying the alkyl compound of formula (XVI). This transformation is shown in Scheme 9. [ka] Scheme 9

[0285] R 8 C 1-6 Compounds of formula (XVI) that are alkyl are 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 dichloride, [1,1-bis(diphenylphosphine)ferrocene]dichloropalladium(II), palladium acetate, or bis(diphenylphosphine)palladium(II) chloride, where X is Cl, Br, or I, and R 8 C 1-6Compounds of formula (VI) that are alkyl, and R 7 Hydrogen and C are independent of each other. 1-6 Alkyl or two R 7 together C 3-8 These compounds can be prepared by Suzuki cross-coupling with a compound of formula (III) that can form a cycloalkyl group. Furthermore, this conversion can be used to prepare a compound of formula (XV) from a compound of formula (IV). These conversions are shown in Scheme 10. [ka] Scheme 10

[0286] Alternatively, the compound of formula (II), where X is Cl, Br, or I, can be prepared by reacting the compound of formula (XVII) with a halogenating agent such as N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, or bromine in a suitable solvent such as dichloromethane, chloroform, tetrahydrofuran, or acetonitrile. This conversion is shown in Scheme 11. [ka] Scheme 11

[0287] The compound of formula (XVII) can be prepared by reacting the compound of formula (XIII) with the compound of formula (V) and a coupling agent, such as N,N'-dicyclohexylcarbodiimide, bis(2-oxo-3-oxazolidinyl)phosphinate chloride, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, propylphosphonic anhydride, or cyanuryl chloride, and optionally a base such as triethylamine, ethyldiisopropylamine, or N-methylmorpholine, in a suitable solvent such as ethyl acetate, dimethylformamide, tetrahydrofuran, or dichloromethane. This conversion is shown in Scheme 12. [ka] Scheme 12

[0288] Alternatively, the compound of formula (II) can be prepared by reacting the compound of formula (XVIII) with the compound of formula (XIX) (wherein Y is Cl, Br, I, OSO2CF3, OSO2C6H4CH3, or OSO2CH3) in the presence of a base such as Cs2CO3, K2CO3, or NaOtBu. This transformation is shown in Scheme 13. [ka] Scheme 13

[0289] Compounds of formula (XVIII), where X is Cl, Br, or I, can be prepared by reacting a compound of formula (IV), where X is Cl, Br, or I, with a compound of formula (XX) and a coupling agent, such as N,N'-dicyclohexylcarbodiimide, bis(2-oxo-3-oxazolidinyl)phosphinate chloride, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, propylphosphonic anhydride, or cyanuryl chloride, and optionally a base such as triethylamine, ethyldiisopropylamine, or N-methylmorpholine, in a suitable solvent such as ethyl acetate, dimethylformamide, tetrahydrofuran, or dichloromethane. This conversion is shown in Scheme 14. [ka] Scheme 14

[0290] Alternatively, the compound of formula (I) may be prepared by reacting the compound of formula (XXI) with the compound of formula (XXII) (wherein Y is OH) and a coupling agent, such as N,N'-dicyclohexylcarbodiimide, bis(2-oxo-3-oxazolidinyl)phosphinate chloride, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, propylphosphonic anhydride, or cyanuryl chloride, and optionally a base such as triethylamine, ethyldiisopropylamine, or N-methylmorpholine, in a suitable solvent such as ethyl acetate, dimethylformamide, tetrahydrofuran, or dichloromethane. This conversion can also be carried out by reacting the compound of formula (XXI) with the compound of formula (XXII) (wherein Y is Cl) and optionally a base such as triethylamine, ethyldiisopropylamine, or pyridine in a suitable solvent such as ethyl acetate, pyridine, or tetrahydrofuran. This conversion is shown in Scheme 15. [ka] Scheme 15

[0291] The compound of formula (XXI) is mixed with the compound of formula (XXIII) where X is Cl, Br, or I in a suitable solvent such as dimethylformamide, dioxane, tetrahydrofuran, ethanol, or water, in the presence of a base such as Cs2CO3, K2CO3, or NaOtBu, and a suitable palladium catalyst such as tetrakistriphenylphosphine palladium, palladium dichloride, [1,1-bis(diphenylphosphine)ferrocene]dichloropalladium(II), palladium acetate, or bis(diphenylphosphine)palladium(II) chloride, and R 7 Hydrogen and C are independent of each other. 1-6 Alkyl or two R 7 together become C 3-8 It can be prepared by Suzuki cross-coupling with a compound of formula (III) that can form a cycloalkyl group. This transformation is shown in Scheme 16. [ka] Scheme 16

[0292] Compounds of formula (V) and (XX) are commercially available or can be prepared using known methods. For example, M.Milen, B.Nyulasi, T.Nagy, G.Simig, B.Volk, Beilstein J.Org.Chem.2022,18,653; M.Imanishi, M.Sonoda, H.Miyazato, Ko Sugimoto, M.Akagawa, S.Tanimori,ACS Omega2017,2,1875;JXQiao,TCWang,R.Ruel,C.Thibeault,A.L'Heureux,WASchumacher,SASpronk,S.Hiebert,G.Bouthillier,J.Lloyd,Z.Pi,DMSchnur,LMAbell,J.Hua,LAPrice,E.Liu,Q. Wu,TESteinbacher,JSBostwick,M.Chang,J.Zheng,Q.Gao,B.Ma,PAMcDonnell,CSHuang,R.Rehfuss,RRWexler,PYSLamJ.Med.Chem.2013,56,9275-9295;AMMcKinney,KRJackson,R.Nicholas Salvatore, E.-M. Savrides, MJ Edattel, T. Gavin, J. Heterocyclic Chem.2005, 42, 1031; S. Ucar, S. Essiz, A. Dastan, Tetrahedron 2017, 73, 1618-1632; F. Fache, Synlett 2004, 15, 2827-2829.

[0293] R 7 Hydrogen and C are independent of each other. 1-6 Alkyl or two R 7 together become C 3-8Compounds of formula (III) and (XXIII) that can form cycloalkyl groups are prepared by known methods or are commercially available. For example, GSBasarab JIManchester,S.Bist,PABoriack-Sjodin,B.Dangel,R.Illingworth†,BASherer,S.Sriram,M.Uria-Nickelsen,AEEakin,J.Med.Chem.2013,56,8712-8735;M.Gravel,KAThompson,M.Zak,C.Berube ,DGHall,J.Org.Chem.,2002,67,3-15;S.Kitamura,KLHvorecny,J.Niu,BDHammock,DRMadden,C.Morisseau,J.Med.Chem.2016,59,4790-4799;J.Maity,D.Honcharenko,R.Stroemberg,Tetrahedron See Letters2015, 56, 4780-4783.

[0294] Those skilled in the art will understand that the above amide coupling reactions between an acid, an amine, and a coupling agent can also be carried out using the corresponding acid chlorides and amines. The conversion of an acid to its corresponding acid chloride is well known to those skilled in the art.

[0295] The compound of formula (Ij) can be prepared by reacting the compound of formula (I), where Z is O, 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 17. [ka] Scheme 17

[0296] Alternatively, the compound of formula (Ij), where Z is S, can be prepared by reacting the compound of formula (XXIV) with the compound of formula (XXII) (wherein Y is OH) and a coupling agent, such as N,N'-dicyclohexylcarbodiimide, bis(2-oxo-3-oxazolidinyl)phosphinate chloride, 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, propylphosphonic anhydride, or cyanuryl chloride, and optionally a base such as triethylamine, ethyldiisopropylamine, or N-methylmorpholine, in a suitable solvent such as ethyl acetate, dimethylformamide, tetrahydrofuran, or dichloromethane. This conversion can also be carried out by reacting the compound of formula (XXIV) with the compound of formula (XXII) (wherein Y is Cl) and optionally a base such as triethylamine, ethyldiisopropylamine, or pyridine in a suitable solvent such as ethyl acetate, pyridine, or tetrahydrofuran. This conversion is shown in Scheme 18. [ka] Scheme 18

[0297] The compound of formula (XXIV) can be prepared by reacting the compound of formula (XXI) 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 19. [ka] Scheme 19

[0298] Those skilled in the art will understand that the above amide coupling reactions between acids, amines, and coupling agents can also be carried out using the corresponding acid chlorides and amines. The conversion of acids to their corresponding acid chlorides is well known to those skilled in the art.

[0299] It will be understood by those skilled in the art that some of the above reactions, in which the nitrogen atom of the central imidazole ring is unsubstituted, may function more efficiently if the nitrogen atom of the imidazole is masked with a protecting group such as trimethylsilylethoxymethyl (SEM), tert-butoxycarbonyl (Boc), or 2-tetrahydropyranyl (THP). The protection reactions of the imidazole ring with SEM, Boc, or THP, along with the subsequent deprotection of those groups, are transformations well understood by those skilled in the art. Information on these transformations can be found in literature such as Greene's Protective Groups, Organic Synthesis, Fourth Edition, Chapter 7.

[0300] When the term "compound / multiple compounds according to the present invention" is used, it refers to the compound according to the present invention.

[0301] Alternatively, the compounds according to the present invention can be obtained by 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.

[0302] A compound according to the present invention can be converted in a manner known to itself to another compound according to the present invention by replacing one or more substituents of a starting compound according to the present invention with other substituents according to the present invention in a conventional manner.

[0303] Depending on the selection of suitable reaction conditions and starting materials in each case, it may be possible, for example, to replace only one substituent with another substituent according to the present invention in one reaction step, or to replace multiple substituents with other substituents according to the present invention in the same reaction step.

[0304] Salts of the compounds according to the present invention can be prepared by methods known in themselves. 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.

[0305] Salts of the compounds according to the present invention can be converted to the 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.

[0306] Salts of compounds according to the present invention can be converted to other salts of compounds according to the present invention by methods known in themselves. For example, an acid addition salt can be converted to another acid addition salt by treating an inorganic acid salt, such as a hydrochloride salt, with a suitable metal salt, such as a sodium salt, barium salt, or silver salt of the acid, for example, silver acetate, in a suitable solvent in which the inorganic salt forming silver chloride is insoluble and therefore precipitates from the reaction mixture.

[0307] 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.

[0308] In each case, the compounds of the present invention in free or salt form, and where appropriate, their tautomers, may exist in one form of possible stereoisomers or as mixtures thereof, depending on the number, absolute or relative configuration of chiral carbon atoms present in the molecule and / or the stereoconfiguration of non-aromatic double bonds present in the molecule, for example, in the form of pure stereoisomers such as anticonformities and / or diastereomers, or as mixtures of stereoisomers such as racemates, diastereomer mixtures or racemic mixtures, and the present invention shall be understood in this sense in each of the above and below cases with respect to pure stereoisomers and all possible mixtures of stereoisomers, even if the details of stereochemistry are not specifically described in each case.

[0309] Depending on the selected starting materials and procedure, the diastereomer mixtures or racemic mixtures of the compounds according to the present invention, in free or salt form, can be separated into pure diastereomers or racemic mixtures based on physicochemical differences of the components by known methods, for example, fractional crystallization, distillation and / or chromatography.

[0310] Enantiomer mixtures such as racemates obtained by similar methods can be broken down 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 suitable microorganisms, by cleavage by specific immobilized enzymes via the formation of inclusion compounds or conversion to diastereomer salts, 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 diastereomers from which the desired enantiomer can be released by the action of a suitable substance, for example a basic substance.

[0311] Pure diastereomers or enantiomers can be obtained according to the present invention not only by separating suitable stereoisomer mixtures, but also by generally known methods of diastereoselective or enantioselective synthesis, such as the method according to the present invention using suitable stereochemical starting materials. 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. When individual components have different biological activities, it is advantageous to isolate or synthesize the biologically more effective stereoisomers, such as enantiomers or diastereomers, or stereoisomer mixtures, such as enantiomer mixtures or diastereomer mixtures, in each case. The compounds according to the present invention, and optionally their tautomers, in their free or salt forms, may also be obtained in hydrate form as needed, and / or in other solvents, such as solvents used for crystallization of compounds existing in solid form. The following examples illustrate, but do not limit, the present invention.

[0312] The present invention also provides intermediates useful for preparing the compounds according to the present invention.

[0313] The following intermediates form further embodiments of the present invention.

[0314] 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 3-6Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and -NHC(O)C 1-6 Independently selected from alkyl groups, preferably R 1a and R 1c is hydrogen, and 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 1-6 Alkylsulfonyl and -NHC(O)C 1-6 Selected from alkyl groups, A 2 CR is independent. 2 or N, provided there are 3 or fewer A 2 is N, preferably two or fewer A 2 is N, preferably one or less A 2 is N, and more preferably four A 2 CR 2 The condition is that, 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-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 1-6Alkylaminocarbonyl and C 1-6 Independently selected from alkylcarbonyls, 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 and C 1-6 Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxyl, and CN, preferably R 2 is hydrogen, halogen, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Selected independently from alkyl and CN, A 3 CR 3 or N, R 3 These are hydroxy, 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-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkyl sulfanyl, C1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, amino, C 1-6 Alkylamino, diC 1-6 -Alkylamino and C 3-6 Selected from cycloalkylaminos, 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 Alkoxycarbonyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, 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 halogen, hydroxyl, and CN, preferably R 3 These are hydroxy, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Selected from alkoxycarbonyls, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Each alkoxycarbonyl group may be optionally substituted with one substituent selected from halogen, hydroxyl, and CN, R 3 is adjacent to R 2 Together with these, a ring, preferably a 5- to 8-membered heterocycle, more preferably a 5-membered heterocycle or a 6-membered heterocycle, is arbitrarily formed. R 4 C1-6 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, 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, C1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy, 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, preferably 1 substituent, which can be independently selected from halogens and CN. 3 and R 4 Together, they arbitrarily form a ring, preferably a 5-8 membered heterocycle, more preferably a 6-membered heterocycle, and X is Cl, Br, or I. A compound of the same, or its salt or N-oxide.

[0315] Formula (XVII) [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, and -NHC(O)C 1-6 Selected independently from alkyl, preferably R1a and R 1c is hydrogen, and R 1bThese are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkylsulfonyl and -NHC(O)C 1-6 Selected from alkyl groups, A 2 CR is independent. 2 or N, provided there are 3 or fewer A 2 is N, preferably two or fewer A 2 is N, preferably one or less A 2 is N, and more preferably four A 2 CR 2 The condition is that, 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-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 and C 1-6 Independently selected from alkylcarbonyls, 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, C3-6 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 and C 1-6 Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxyl, and CN, preferably R 2 is hydrogen, halogen, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Selected independently from alkyl and CN, A 3 CR 3 or N, R 3 These are hydroxy, 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 Alkoxycarbonyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkylsulfonyl, amino, C 1-6 Alkylamino, diC 1-6 -Alkylamino and C 3-6 Selected from cycloalkylaminos, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkylsulfonyl, 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 halogen, hydroxyl, and CN, preferably R 3 These are hydroxy, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Selected from alkoxycarbonyls, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Each alkoxycarbonyl group may be optionally substituted with one substituent selected from halogen, hydroxyl, and CN, R 3 is adjacent to R 2 Together with these, they arbitrarily form a ring, preferably a 5- to 8-membered heterocycle, more preferably a 5-membered heterocycle or a 6-membered heterocycle, 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 1-6Alkylsulfinyl-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, 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, C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C1-4 Alkyl and C 1-6 Each alkoxy group may be optionally substituted with 1 to 3 substituents, preferably 1 substituent, which can be independently selected from halogens and CN. 3 and R 4 (Together, they arbitrarily form a ring, preferably a 5-8 membered heterocycle, more preferably a 6-membered heterocycle.) A compound of the same, or its salt or N-oxide.

[0316] 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 application rates, the sufficient tolerance exhibited by plants, and their environmental safety. They possess highly useful curative, preventive, and systemic properties and can be used to protect many cultivated plants. The compounds of formula (I) as defined in this invention may 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.

[0317] Compounds of formula (I) as defined herein may also be used as fungicides. As used herein, the term “fungicide” means a compound that controls, modifies, or prevents the growth of fungi. The term “fungicidal effective amount” means the amount of such compound or combination of such compounds that can produce an effect on the growth of fungi. Controlling or modifying effects include all deviations from natural occurrence, such as death or delay, and prevention includes the formation of barriers or other defenses in or on plants to prevent fungal infection.

[0318] For protection against fungal infections and plant pathogenic fungi in the soil, the mixture of formula (I) as defined in this invention can also be used as a coating agent for treating plant propagation materials, such as seeds, tubers, or grains of fruits, or plant cuttings (e.g., rice). The propagation material may be treated with a composition containing the compound of formula (I) as defined in this invention before planting. For example, seeds may be coated before sowing. The compound of formula (I) as defined in this invention may also be applied (coated) to grains 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. This invention also relates to such methods for treating plant propagation materials and to plant propagation materials thus treated.

[0319] Furthermore, the compounds of formula (I) as defined in the present invention may be used to control fungi in related fields, such as the protection of industrial materials including wood and wood-related industrial products, food storage, and hygiene management.

[0320] In addition, the present invention can be used to protect non-biological materials, such as sawn timber, wall coverings, and paints, from fungal attacks.

[0321] The compounds of formula (I) as defined in this 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 leaf pathogens of ornamental plants, lawns, vegetables, fields, grains, and fruit crops.

[0322] Examples of controllable diseases include the following fungi and fungal vectors, as well as plant pathogenic bacteria and viruses: This includes species such as Absidia corymbifera, Alternaria spp., Aphanomyces spp., Ascochyta spp., Aspergillus spp. (A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus), Aureobasidium spp. (A. pullulans), Blastomyces dermatidis, Blumeria graminis, and Bremia lactucaea. Botryosphaeria species such as *B. lactucae*, *B. dothidea*, and *B. obtusa*; Botrytis species such as *B. cinerea*; Candida species such as *C. albicans*, *C. glabrata*, *C. krusei*, *C. lusitaniae*, *C. parapsilosis*, and *C. tropicalis*; Cephaloascus fragrans; and Ceratocystis species. Cercospora spp., such as C. arachidicola, Cercosporidium personatum, Cladosporium spp., Claviceps purpurea, Coccidioides immitis, Cochliobolus species, Colletotrichum species such as C. musae, Cryptococcus neoformans, Diaporthe spp., Didymella spp., Drecxlera spp., Elsinoe spp. Species of the genus Epidermophyton, species of the genus Erysiphe such as Erwinia amylovora and E. cichoracearum, Fusarium spp., including Eutypa lata, F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, F. solani, Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, and Gloeosporium musarum. musarum), Glomerella cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Helminthosporium spp, Hemileia spp, Histoplasma spp such as H. capsulatum, Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium sediciosum Mycosphaerella species such as *Mycosphaerella spp.* (including *Mycosphaerella spp.*), *Mycosporum nivale*, *Mycosporum spp.*, *Mycosporum spp.*, *Mycosporum spp.* (including *Mycosphaerella spp.*), *Mycosporum spp.* (including *Mycosphaerella spp.*), *Mycosporum spp.* (including *Mycosphaerella spp.*).), Oncobasidium theobromaeon, Ophiostoma piceae, species of the genus Paracoccidioides, species of the genus Penicillium such as P. digitatum and P. italicum, species of the genus Petriellidium, species of Peronosclerospora such as P. maydis, P. philippinensis and P. sorghi, species of Peronospora, species of Peronospora, Phaeosphaeria nodorum * * Pseudomonas species (Pseudomonas spp.), P. cubensis, P. humuli, and other Pseudoperonospora species, Pseudopeziza tracheiphila, P. hordei, P.Puccinia species such as P. recondita, P. striiformis, and P. triticina; Pyrenopeziza species, Pyrenophora species; Pyricularia species such as P. oryzae; Pythium species such as P. ultimum; Ramularia species; Rhizoctonia species; Rhizomucor pusillus; Rhizopus arrhizus; and Rhynchosporium species. Species of the genus *Scedosporium*, such as *S. apiospermum* and *S. prolificans*, and *Schizothyrium pomi*, are included. Species of the genera Sclerotinia, Sclerotium, Septoria (including S. nodorum and S. tritici), Sphaerotheca macularis, Sphaerotheca fusca (Sphaerothorix fuliginea), Sporothorix, Stagonospora nodorum, Stemphylium, Stereum hirsutum, and Thanatephorus cucumeris. *Trichoderma spp.*, including *T. cucumeris*, *Tielaviopsis basicola*, *Tilletia* species, *T. harzianum*, *T. pseudokoningii*, and *T. viride*. Species belonging to the genera Trichophyton, Typhula, Uncinula necator, Urocystis, Ustilago, Venturia (including V. inaequalis), Verticillium, and Xanthomonas.

[0323] In particular, the compounds of formula (I) as defined in the present invention and fungicidal compositions containing them may be used to control plant diseases caused by broad-spectrum fungal plant pathogens in the classes Basidiomycetes, Ascomycetes, Oomycetes and / or Imperfect Mycetes, Brasocladiomycetes, Chytridiomycetes, Glomusmycetes and / or Mucormycetes. More specifically, the compounds of formula (I) as defined in the present invention may be used to control Oomycetes.

[0324] These pathogens may include the following: Phytophthora diseases, such as those caused by oomycetes including 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 disease, such as that caused by Pythium arrhenomanes, Pythium graminicola, Pythium irregulare, Pythium sylvaticum, and Pythium ultimum;Diseases caused by Peronosporales species such as Peronospora destructor, Peronospora parasitica, Plasmopara viticola, Plasmopara halstedii, Pseudoperonospora cubensis, Albugo candida, Sclerophthora macrospora, and Bremia lactucae, as well as Aphanomyces cochlioides, Labyrinthula zosterae, and Peronosclerospora sorghi Others such as *Sorghi* and *Sclerospora graminicola*; Ascomycetes, such as those causing spotted disease, leaf spot, blast disease, or canker and / or rot, such as Stemphylium solani, Stagonospora tainanensis, Spirocaea oleaginea, Setosphaeria turcica, Pyrenochaeta lycoperisici, Pleospora herbarum, Phoma destructiva, Phaeosphaeria herpotrichoides, and Phaeocryptocus gaeumannii. Ophiosphaerella graminicola, Ophiobolus graminis, Leptosphaeria maculans, Hendersonia creberrima, Helminthosporium triticirepentis, Setosphaeria turcica, Drechslera glycines, Didymella bryoniae, Cycloconium oleagineum, Corynespora cassiicola, Cochliobolus satibus sativus), Bipolaris cactivora, apple scab fungus (Venturia inaequalis), Pyrenophora teres, wheat yellow spot fungus (Pyrenophora tritici-repentis), Alternaria alternataPleosporales species such as Alternaria alternata, Alternaria brassicola, Alternaria solani, and Alternaria tomatophila, Septoria tritici, Septoria nodorum, Septoria glycines, Cercospora arachidicola, Cercospora beticola, Cercospora sojina, Cercospora zeae-maydis, Cercosporella capsellae, and Cercosporella herpotrichoides, all belonging to the Capnodiales order, as well as Cladosporium carpophilum and Cladosporium efsum. effusum), Passalora fulva, Cladosporium oxysporum, Dothistroma septosporum, Isariopsis clavispora, Mycosphaerella fijiensis, Mycosphaerella graminicola, Mycovellosiella koepkeii, Phaeoisariopsis bataticola, Pseudocercospora vitis, Pseudocercosporella herpotrichoid herpotrichoides), Ramularia beticola, Ramularia collo-cygni, Gaeumannomyces graminis, Magnaporthegrisea, rice blast fungus (MagnaportheMagnaporthales (such as oryzae), Anisogramma anomala, Apiognomonia errabunda, Cytospora platani, Diaporthe phaseolorum, Discula destructiva, Gnomonia fructicola, Greeneria uvicola, Melanconium juglandinum, Phomopsis viticola, Sirococcus clavigignenti-jugrandacearam This includes species of the Diaporthales order such as clavigignenti-juglandacearum, Tubakiadryina, Dicarpera spp., Valsa ceratosperma, as well as Actinothyrium graminis, Ascochyta pisi, Aspergillus flavus, Aspergillus fumigatus, Aspergillus nidulans, Asperisporium caricae, and Blumerierella jaapii. Candida spp., Capnodium ramosum, Cephaloascus spp., Cephalosporium gramineum, Ceratocystis paradoxa, Chaetomium spp., Hymenoscyphus pseudoalbidus, Coccidioides spp., Cylindrosporium padi, Diplocarpon malae, Drepanopeziza campestris Campestris), Elsinoe ampelina, Epicoccum nigrum, Epidermophyton spp.), Eutypa lata, Geotrichum candidum, Gibellina cerealis, Gloeocercospora sorghi, Gloeodes pomigena, Gloeosporium perennans, Gloeotinia temulenta, Griphospaeria corticola, Kabatiella lini, Leptographium microsporum, Leptosphaerulinia crassua crassiasca), Lophodermium seditiosum, Marssonina graminicola, Microdochium nivale, Monilinia fructicola, Monographella albescens, Monosporascus cannonballus, Naemacyclus spp., Ophiostoma novo-ulmi, Paracoccidioides brasiliensis, Penicillium expansum, Pestalotia rhododendri (rhododendri), Petriellidium spp., Pezicula spp.), phialophora gregata, Phyllachora pomigena, Phymatotrichum omnivora, Physalospora abdita, Plectosporium tabacinum, Polyscytalum pustulans, Pseudopeziza medicaginis, Pyrenopeziza brassicae, Ramulispora sorghi, Rhabdoclinep seudotsugae, Rhynchosporium sekaris secalis), rice leaf rot fungus (Sacrocladium oryzae), species of the genus Scedosporium, Schizothyrium pomi, Sclerotinia sclerotiorum, Sclerotinia minor, species of the genus Sclerotium, Typhula ishikariensis, etc. Caused by other plants such as Seimatosporium mariae, Lepteutypa cupressi, Septocyta ruborum, Sphaceloma perseae, Sporonema phacidioides, Stigmina palmivora, Tapesia yallundae, Taphrina bullata, Thielviopsis basicola, Trichoseptoria fructigena, Zygophiala jamaicensis, etc.; powdery mildew, for example, Blumeria graminis. Caused by the Erysiphales order, including *Porphyra graminis*, *Erysiphe polygoni*, *Uncinula necator*, *Sphaerotheca fuligena*, *Podosphaera leucotricha*, *Podospaera macularis*, *Golovino mycescichoracearum*, *Leveillula taurica*, *Microsphaera diffusa*, *Oidiopsis gossypii*, *Phyllactinia guttata*, and *Oidium arachidis*;Caused by fungi, such as those belonging to the Botryosphaeriales order, including Dothiorella aromatica, Diplodia seriata, Guignardia bidwellii, Botrytis cinerea, Botryotinia allii, Botryotinia fabae, Fusicoccum amygdali, Lasiodiplodia theobromae, Macrophoma theicola, Macrophomina phaseolina, and Phyllosticta cucurbitacearum;Anthracnose, for example, caused by Glommerelales species such as Colletotrichum gloeosporioides, Colletotrichum lagenarium, Colletotrichum gossypii, Glomerella cingulata, and Colletotrichum graminicola, as well as damping-off or canker, for example, Acremonium strictum, Claviceps purpurea, Fusarium culmorum, Fusarium graminearum, Fusarium bilgriforme Fusarium virguliforme), Fusarium oxysporum, Fusarium subglutinans, Fusarium oxysporum f.sp.cubense, Gerlachia nivale, Gibberella fujikuroi, Gibberella zeae, Gliocladium spp., Myrothecium verrucaria, Nectria ramulariae, Trichoderma viride, Trichothecium roseum Caused by Hypocreales, such as roseum and Verticillium theobromae. Basidiomycetes, such as smut, caused by Ustilaginales species such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, and Ustilago zeae; rust, such as Cerotelium fici, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, 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 Secalis), Pucciniastrum coryli, Cronartium ribicola, Gymnosporangium juniperi-viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor, and Uromyces viciae-fabee. This includes diseases caused by the order Uredinales, such as viciae-fabae, as well as other rot and disease, such as species of the genera 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 Caused by *Tillets* (Moliniae) and *Tilletia caries*. Blastocladiomycetes, such as Physoderma maydis. Mucoromycete species such as Choanephora cucurbitarum, Mucor spp., and Rhizopus arrhizus, as well as Diseases caused by other species and genera closely related to those listed above.

[0325] In addition to their fungicidal activity, compositions comprising the compounds and 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.

[0326] Within the scope of the present invention, the protected target crops and / or useful plants 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, such as basil, borage, chives, coriander, lavender, lavender, mint, oregano, parsley, rosemary, sage, and thyme; legumes, such as kidney beans, lentils, peas, and soybeans; nuts, such as almonds, cashews, peanuts, hazelnuts, peanuts, pecans, pistachios, and walnuts; palms, such as oil palms; ornamental plants, such as flowers, shrubs, and trees; other trees, such as cocoa, coconuts, olives, and rubber trees; vegetables, such as asparagus, eggplant, broccoli, cabbage, carrots, cucumbers, garlic, lettuce, mallow, melon, okra, onions, peppers, potatoes, pumpkins, rhubarb, spinach, and tomatoes, as well as climbing plants, including perennial and annual crops such as grapes.

[0327] 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 marketed 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.

[0328] It should be understood that the terms “useful plants” and / or “target crops” also include useful plants that have been conferred resistance to herbicides such as bromoxynil or herbicides of the same class (e.g., HPPD inhibitors, ALS inhibitors, e.g., primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovir-sikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors, or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional breeding methods or genetic engineering. An example of a crop conferred resistance to imidazolinones, e.g., imazamox, by conventional breeding methods (mutation) 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®.

[0329] 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, which can, for example, 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 proteins (Vip), insecticidal proteins 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 pests (superimposed transgenic events when brought about by so-called genetic modification). For example, a plant may 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).

[0330] It should be understood that the terms “useful plants” and / or “target crops” 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.

[0331] Toxins that can be expressed by transgenic plants include, for example, insecticidal proteins or δ-endotoxins derived from Bacillus cereus or Bacillus popilliae, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, insecticidal proteins derived from Bacillus thuringiensis or vegetative insecticidal proteins (Vip), such as Vip1, Vip2, Vip3 or Vip3A, or nematode symbiotic bacteria, such as Photorhabdus luminescens and Xenorhabdus nematophilus, and species of the genus Photorhabdus. Insecticidal proteins of Xenorhabdus spp. (spp.) or species of the genus Xenorhabdus; toxins produced by animals, such as scorpion toxin, arachnid toxin, wasp toxin and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycete toxin; plant lectins, such as pea lectin, barley lectin or saxifrage lectin; aglutinin; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patain, cystatin, and papain inhibitors; lysine, maize-RIP, Examples include ribosomal inactivating proteins (RIPs) such as abrin, rufin, saporin, or briodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, and HMG-COA-reductase; ion channel blockers such as sodium or calcium channels; juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, vibenzyl synthase, chitinase, and glucanase.

[0332] Furthermore, in connection with the present invention, it should be understood that there are δ-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or vegetative insecticidal proteins (Vip), such as Vip1, Vip2, Vip3, or Vip3A, and more specifically, 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, a protease recognition sequence that is not naturally present is preferably 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).

[0333] 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.

[0334] The processes for preparing 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.

[0335] The toxins contained in transgenic plants confer resistance to harmful insects. Such insects can exist in any of the insect taxa, but are commonly found in beetles (Coleoptera), diptera, and butterflies (Lepidoptera).

[0336] Transgenic plants are known that contain one or more genes encoding insecticide resistance and expressing one or more toxins, some of which 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 phosphinothrycin N-acetyltransferase (PAT) for 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 resistance trait), Agrisure (registered trademark) CB Advantage (Bt11 corn borer (CB) trait), and Protecta (registered trademark).

[0337] Further examples of such genetically modified crops include: 1. Bt11 maize, from 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. Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. Bt176 maize, 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. Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, MIR604 maize, 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. Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. MON 863 maize, registration number C / DE / 02 / 9. MON 863 expresses the Cry3Bb1 toxin and is resistant to certain Coleoptera insects. 5. IPC 531 Cotton, Monsanto Europe, SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02. 6. Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, 1507 Maize, 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 corn, registered under registration number C / GB / 02 / M3 / 03, from Monsanto Europe, SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. This is a conventional hybrid corn variety created by crossing the genetically modified variety NK603 with MON 810. NK603×MON810 corn transgenically expresses the protein CP4 EPSPS obtained from the CP4 strain of Agrobacterium sp., thereby conferring resistance to the herbicide Roundup® (containing glyphosate). It also transgenically expresses the Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki, which provides resistance to certain lepidopteran insects, including the corn borer.

[0338] As used herein, the term “habitat” means a field in which plants grow or on which seeds of cultivated plants are sown or in which seeds will be sown in the soil. It includes the soil, seeds and seedlings, and established vegetation.

[0339] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves, and fruits.

[0340] The term "plant propagation material" is understood to refer to plant materials that can be used for plant propagation, such as seeds and other reproductive parts, as well as cuttings or tubers, such as potatoes. 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 complete or partial treatment by immersion. Preferably, "plant propagation material" is understood to mean seeds.

[0341] The pesticides referred to herein by their common names are known, for example, from "The Pesticide Manual," 19th Ed., British Crop Protection Council 2021.

[0342] The 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 in known methods into emulsifiable concentrates, coating pastes, ready-to-spray or dilutable solutions or suspensions, diluted emulsions, wettable powders, soluble powders, powders for spraying, 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, may be 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.

[0343] 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.

[0344] 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, antifoaming 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.

[0345] 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.

[0346] Emulsifying concentrates are homogeneous liquid compositions that are dispersible in water or other liquids, and may consist solely of the active compound and a liquid or solid emulsifier, or 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 are 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.

[0347] Granular formulations include both extruded 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, sugar, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate, and other organic or inorganic materials that can absorb or be coated with the active compound. Granular formulations typically contain 5% to 25% active ingredients, which may include surfactants such as heavy aromatic naphtha, kerosene, and other petroleum fractions, or stickers such as vegetable oils and / or dextrin, glue, or synthetic resins.

[0348] Powder for dispersal is a free-flowing mixture of an active ingredient and finely ground solids such as talc, clay, powder, and other organic and inorganic solids that act as a dispersant and carrier.

[0349] 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.

[0350] 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.

[0351] Suitable agricultural additives and / or carriers useful for formulating the composition of the present invention in the above-mentioned formulation types are well known to those skilled in the art.

[0352] 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 nic acid, 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.

[0353] 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.

[0354] 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.

[0355] 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.

[0356] In addition, other biocides or compositions may be combined with the composition of the present invention and used in the method of the present invention, and may be applied simultaneously with or sequentially with the composition of the present invention. When applied simultaneously, these further active ingredients may be formulated together with the composition 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.

[0357] The following combinations of a 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 1.1-1.27, 2.1-2.45, 3.1-3.55, 4.1-4.24 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 -Illacetate+TX, (E,Z)-Tetradeca-4,10-Diene-1-Illacetate+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-arl + TX, (Z)-tetradeca-9-en-1-ol + TX, (Z)-tetradeca-9-en-1-yl acetate + 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-thion + T X, 2-(octylthio)ethanol + TX, 2-chlorophenyl N-methylcarbamate (CPMC) + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide + TX, 4-(quinoxaline-2-ylamino)benzenesulfonamide + TX, 4-methylnonan-5-ol and 4-methylnonanan-5-one + TX, 5-methyl-6-thioxo-1,3,5-Thiadiandinane-3-ylacetate + TX, 6-Isopentylaminopurine + TX, 8-Hydroxyquinoline sulfate + TX, Abamectin + TX, Acequinosyl + TX, Acetamiprid + TX, Acetoprole + TX, Acrinatrin + TX, Acinonapir + TX, Adoxophyes orana GV + TX, Afidopiropen + TX, Afoxolanar + TX, Agrobacterium radiobacter + TX, AKD-3088 + TX, Aranicarb + TX, Aldicarb + TX, Aldoxycarb + TX, Allethrin + TX, Alpha-Cypermethrin + TX, Alpha-Methrin + TX, Alpha-Multistriatin + TX, Amblyseius species 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, AZ60541+TX, Azadirachtin+TX, Azocyclotin+TX, Bacillus aizawai+TX, Bacillus chitinosporus AQ746 (NRRL accession number B-21618)+TX, Bacillus firmus+TX, Bacillus kurstaki+TX, Bacillus mycoides AQ726 (NRRL accession number B-21664)+TX, Bacillus pumilus (NRRL accession number B-30087)+TX, Bacillus pumilus Bacillus pumilus AQ717 (NRRL accession number B-21662) + TX, Bacillus sp. AQ175 (ATCC accession number 55608) + TX, Bacillus sp. AQ177 (ATCC accession number 55609) + TX, Bacillus sp. AQ178 (ATCC accession number 53522) + TX, Bacillus sphaericus Neide + TX, Bacillus subtilis AQ153 (ATCC accession number 55614) + TX, Bacillus subtilis AQ30002 (NRRL accession number B-50421) + TX, Bacillus subtilis subtilis)AQ30004(NRRL accession number B-50455)+TX, Bacillus subtilis(Bacillus subtilis)AQ713(NRRL accession number B-21661)+TX, Bacillus subtilis(Bacillus subtilis)AQ743(NRRL accession number B-21665)+TX, Bacillus subtilis(Bacillus subtilis)Unspecified+TX, Bacillus thuringiensis(Bacillusthuringiensis)AQ52(NRRL accession number B-21619)+TX,Bacillus thuringiensis BD#32 (NRRL accession 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. tenebryonis (subsp. Tenebrionis) + TX, Bacillus thuringiensis subspec. kurstaki (BMP123) + TX, Beauveria bassiana + TX, Beauveria brongniartii + TX, Bencrotiaz + TX, Benomyl + TX, Bensultap + TX, Benzoximate + TX, Benzpyrimoxane + TX, Beta-cyfluthrin + TX, Beta-cypermethrin + TX, Bethoxazine + TX, Bifenazate + TX, Bifenthrin + TX, Binapacril + TX, Biorethrin + TX, Biorethmetrin + TX, Tributyltin oxide + TX, Bisadyl + TX, Bistriflurone + TX, Bisulfurf N+TX, Brevicomin+TX, Brofuranilide+TX, Broflutrinate+TX, Bromoacetamide+TX, Bromophos-ethyl+TX, Bronopol+TX, Busulfan+TX, Butocarboxime+TX, Butopyronoxyl+TX, Butoxy(polypropylene glycol)+TX, Butylpyridaben+TX, Cadsaphos+TX, Calcium arsenate+TX, Carbaryl+TX, Carbofuran+TX, Carbon disulfide+TX, Carbosulfan+TX,Kartap+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 No. 1445683-71-5+TX, CAS No. 1445684-82-1+TX, CAS No. 1594626-19-3+TX, CAS No. 1594637-65-6+TX, CAS No. 1632218-00 -8+TX, CAS 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 1 990457-52-7+TX, CAS number 1990457-55-0+TX, CAS number 1990457-57-2+TX, CAS number 1990457-66-3+TX, CAS number 1990457-77-6+T X, 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 21287 06-04-5+TX, CAS number 2128706-05-6+TX, CAS number 2133042-31-4+TX, CAS number 2133042-44-9+TX, CAS number 2171099-09-3+TX, C AS 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 (Leptinotarsa ​​desemlinator) Decemlineata-specific recombinant double-strand interference GS2) + TX, Chlorantraniliprole + TX, Chlordan + TX, Chlorfenapyr + TX, Chloropicrin + TX, Chloroprallethrin + TX, Chlorpyrifos + TX, Chromafenozide + TX, Chrysopera carnea + TX, Clenpyrin + TX, Chloetocarb + TX, Clothianidin + TX, Codorrelua + TX, Codormon + TX, Copper acetoarsenate + TX, Copper dioctanoate + TX, Copper hydroxide + TX, Copper sulfate + TX, Cresol + TX, Clufomate + TX, Cryptolaemus montrouzieri + TX, Querua + TX, Cyanophenphos + TX, Cyantraniliprole + TX, Sibutrin + TX, Cyclaniliprole + TX, Cyclobtriflurum + TX, Cycloprotrin + TX, Cycloxapride + TX, Cydia pomonella GV + TX, Cyenopyrafen + TX, Cietopyrafen + TX, Cyflumetofen + TX, Cyfluthrin + TX, Cyhalodian + TX, Sirohalothrin + TX, Cypermethrin + TX, Cyphenothrin + TX, Cyprofuranilide + TX, Cyromazine + TX, Cytokinin + TX, Dacnusa sibirica Diglyphus isaea (Diglyphus 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, Dichlorophene + TX, Dicriphos + TX, Dichloromezothiaz + TX, Diethyltoluamide + TX, Diflubenzuron + TX, Diglyphus isaea isaea)+TX, dimatif+TX, dimethoate+TX, dimethyl carbonate+TX, dimethyl phthalate+TX, zinpropyridaz+TX, dinactin+TX, dinocap+TX, dinotefuran+TX, dioxabenzophos+TX, dipirithione+TX, Disparl+TX, D-limonene+TX, dodeca-8-en-1-ylacetate+TX, dodeca-9-en-1-ylacetate+TX, dodeca-8,10-Dien-1-yl acetate + TX, Dodicine + TX, Dominicalua + TX, Doramectin + TX, Emamectin + TX, Emamectin benzoate + TX, Empenthrin + TX, Encarsia formosa + TX, Endotal + TX, Endrin + TX, Epinomectin + TX, Epsilon-monfluorothrin + TX, Epsilon-metofluthrin + TX, Eretmocerus eremicus + TX, Esfenvalerate + TX, Ethion + TX, Ethiprole + TX, Etoprophos + TX, Ethyl 4-methyloctanoate + TX, Ethylhexanediol + TX, Ethylene dibromide + TX, Etofenprox + TX, Ethoxazole + TX, Ethopyrafen+TX, Eugenol+TX, Fermented product from seaweed extract and Melasse+TX, Fermented product from Melasse containing seaweed extract and urea+TX, Seaweed extract and fermented plant product+TX, Fermented plant product containing seaweed extract, plant hormones, vitamins, EDTA-chelated copper, zinc and iron+TX, Famfur+TX, Phenaminosulf+TX, Phenamiphos+TX, Phenazaquin+TX, Fenfluthrin+TX, Fenitrothion+TX, Fenmezodithiaz+TX, Phenobucarb+TX, Phenothiocarb+TX , Phenoxycarb + TX, Fenpropathrin + TX, Fenpyrad + TX, Fenpyroximate + TX, Fensulfothione + 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, Fluchlordiniliprole + TX, Flucitrinate + TX, F Lucycloxurone + 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, Flularaner + TX, Fluvalinate + TX, Fluxamethamide + TX, Formaldehyde + TX, Fostiazate + TX, Fostiethane + TX, Freon Tallinn+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), Grandlua I+TX, Grandlua II+TX, Grandlua III+TX, Grandlua IV+TX, Granulovirus+TX, Guadipyr+TX, GY-81+TX, Halfenprox+TX, Halofenozide+TX, Harpin+TX, Helicoverpa armigera nuclear polyhedron disease virus+TX, Helicoverpa zea (HelicoverpaHelicoverpa zea NPV+TX, Helicoverpa zea nuclear polyhedron virus+TX, Heliothis punctigera nuclear polyhedron virus+TX, Heliothis virescens nuclear polyhedron virus+TX, Hemel+TX, Hempa+TX, Heptafluthrin+TX, Heterophos+TX, Heterorhabditis bacteriophora and H. megidis+TX, Hexalua+TX, Hexamide+TX, Hexithiazox+TX, Hippodamia convergence (Convergents) + TX, Hydralgafen + TX, Slaked lime + TX, Imisiaphos + TX, Imidacloprid + TX, Imiprothrin + TX, Indazapiroxamet + TX, Indoxacarb + TX, Iodomethane + TX, Iprodione + TX, Ipsdienol + TX, Ipsenol + TX, Isamidophos + TX, Isazofos + TX, Isocycloseram + TX, Isoflualanum (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, Leptomastix Dactylopii dactylopii)+TX, linetin+TX, Litlure+TX, lupulua+TX, rotilaner+TX, lufenuron+TX, Macrolophus caliginosus+TX, Mamestra brassicae NPV+TX, mecarphone+TX, medolua+TX, megatomoic acid+TX, metaflumizone+TX, metaldehyde+TX, metam+TX, metam-potassium+TX, metam-sodium+TX, Metaphycus helvolus+TX, Metarhizium anisopliae var. acryldumvar.acridum)+TX, Metarhizium anisopliae var.anisopliae+TX, 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, Methylneodecanamide+TX, Metofluthrin+TX, Metolcarb+TX, Mexacalbate+TX, Milbemectin + TX, Milbemycin oxime + TX, Monfluorothrin + TX, Morzide + TX, Moxidectin + TX, Muscarua + TX, Muscodor albus 620 (NRRL accession number 30547) + TX, Muscodor roseus A3-5 (NRRL accession number 30548) + TX, Nabam + TX, NC-184 + TX, Indian lilac-based products + TX, Neodiprion Safe N. sertifer NPV and N. Lecontei NPV + TX, Nickel bis(dimethyldithiocarbamate) + TX, Niclosamide + TX, Niclosamide-olamine + TX, Nicofluprole + TX, TX, Nitenpyram + TX, Nichiazine + Tx, Nitrapyrine + TX, Octadeca-2,13-diene-1-ylacetate + Tx, Octadeca-3,13-diene-1-ylacetate + Tx, Octylinone + TX, Omethoate + TX, Orphalua + Tx, Orius spp. + TX, Oritalua + TX, Ostramon + TX, Oxamate + TX, Oxamyl + TX, Oxazosulfyl + TX, Oxolinic acid + TX, Oxytetracycline + TX, Paecilomyces humosoroseus fumosoroseus)+TX, Paecilomyces lilacinus+TX, parathion-ethyl+TX, Pasteuria nisizawae+TX, Pasteuria penetrans+TX, Pasteuria usgae+TX, P-cymene+TX, penflurone+TX, pentachlorophenol+TX, permethrin+TX, phenothrin+TX, folate+TX, phosphamidone+TX, phosphocarb+TX, Phytoseiulus persimilispersimilis)+TX, picaridin+TX, pioxaniliprole+TX, piperazine+TX, piperonyl butoxide+TX, pyrimicarb+TX, pyrimiphos-ethyl+TX, pyrimiphos-methyl+TX, Plutella xylostella granuloma virus+TX, Plutella xylostella nuclear polyhedrosis virus+TX, nuclear 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, propargito+TX, propethamphos+TX, propoxer+TX, prothiofos+TX, protrifenbut+TX, piflubamide+TX, pymetrozine+TX, pyraclorazole+TX Phos+TX, Pyrafluprole+TX, Pyretram+TX, Pyridaben+TX, Pyridaryl+TX, Pyridine-4-amine+TX, Pyrifluquinazon+TX, Pyrimidifen+TX, Pyriminostrobin+TX, Pyriprole[394730-71-3]+TX, Pyriprole+TX, Pyriproxyfen+TX, QRD420 (Terpenoid Blend)+TX, QRD452 (Terpenoid Blend)+TX, QRD460 (Terpenoid Blend)+TX, Quillaja saponaria (Quillaja saponaria)+TX, quinoclamin+TX, quinonamide+TX, resmethrin+TX, Rhodococcus globerulus AQ719 (NRRL accession number B-21663)+TX, saloranar+TX, S-biorethrin+TX, cebuphos+TX, selamectin+TX, sigurure+TX, silafluofen+TX, simazine+TX, pentachlorophenoxide sodium+TX, sordidine+TX, spidoxamat+TX, spinetram+TX, spinosad+TX, spirobudiphen+TX, spirodiclofen+TX, spiromesifen+TX, spiropidione+TX, spirotetramat+TX, Spodoptera exigua exigua) Polycapsid Nuclear Polyhedrosis Virus + TX, Spodoptera flugyperdafrugiperda) nuclear polyhedron virus + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema feltiae + TX, Steinernema glaseri + TX, Steinernema riobrave + TX, Steinernema scapteris (Steinernema scapterisci)+TX, Steinernema species (Steinernemaspp.)+TX, Streptomyces galbus (NRRL accession number 30232)+TX, Streptomyces species (Streptomycessp.) (NRRL accession number B-30145)+TX, Streptomycin+TX, Streptomycin sesquisulfate+TX, Strychnin+TX, Sulcatol+TX, Sulfiflumin (CAS number 2377084-09-6)+TX, Sulfoxaflor+TX, Ta Jim Curve + TX, Tebufenozide + TX, Tebufenpyrad + TX, Tebupirimiphos + TX, Tecrophthalam + TX, Tefluthrin + TX, Temephos + TX, Tepa + TX, Terbam + 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, Tigolana + 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, Tricogramma species 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, tran-call+TX, ticlopyrazoflor+TX, Typhlodromus occidentalis+TX, uredepa+TX, Verticillium lecanii+TX, Verticillium spp.+TX, xylenoleic acid+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 can be prepared by the method described in International Publication No. 2019 / 110427) +TX, (3',4',5'-Tolfluorobiphenyl-2-yl)amide +TX, (3-Methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxazole-3-yl]phenyl]methanone (These compounds may be prepared by the method described in International Publication No. 2017 / 220485) +TX, (4-Phenoxyphenyl)methyl 2-amino-6-methylpyridine-3-carboxylate (This compound may be prepared by the method described in International Publication No. 2014 / 006945) +T X, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxazole-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 + T X, (E)-trideca-4-en-1-ylacetate + TX, (E,Z)-tetradeca-4,10-dien-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)-Ikos-13-en-10-one + TX, (Z)-Tetradeca-7-en-1-al + TX, (Z)-Tetradeca-9-en-1-ol + TX, (Z)-Tetradeca-9-en-1-yl acetate + TX, (Z,2E)-5-[1-(2,4-dichlorophenyl)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- [Lolophenyl)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-dihydroisoxazoli-5-yl]-3-chlorophenyl]methanesulfonate + TX, 1-(4,5-dimethylbenzimidazole-1-yl)-4,4,5-tolufluoro-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-tolufluoro-3,3-dimethylisoquinoline + TX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridine-3-yl)-4,4,6-tolufluoro-3,3-dimethylisoquinoline + TX, 1-(6-chloro-7-methylpyrazolo[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 e + TX, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxazol-3-yl]phenyl]methyl]urea + TX, 1-[2-[[1-(4-chlorophenyl)pyrazole-3-yl]oxymethyl]-3-methylphenyl]-4-methyl-tetrazole-5-one + TX, 10-diene-1-yl acetate + TX, 14-methyloctadeca-1-ene + TX, 1-bromo-2-chloroethane + TX, 1-dichloro-1-nitroethane + TX, 1-hydroxy-1H-pyridine-2-thione + TX, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxa [Zol-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-carboxamide + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(1,3-dithiolan-2-yl)phenyldi Methyl carbamate + TX, 2-(2-butoxyethoxy)ethyl piperinylate + TX, 2-(2-butoxyethoxy)ethyl thiothianate + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methyl carbamate + TX, 2-(4-chloro-3,5-xylyloxy)ethanol + TX, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethylindan-4- [Iyl]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-dimethylindan-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-oxazole-3-yl]phenyl]acetamide + TX, 2,4-dichlorophenylbenzenesulfonate + TX, 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-the Thoron (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. 20 (This compound may be prepared by the method described in International Publication No. 17 / 029179) + TX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazole-1-yl)propan-2-ol (This compound may be prepared by the method described in International Publication No. 2017 / 029179) + TX, 2-chlorovinyldiethyl phosphate + TX, 2-fluoro-N-methyl-N-1-naphthyl Acetamide + TX, 2-Imidazolidone + TX, 2-Isovalerylindan-1,3-dione + TX, 2-Methyl(propa-2-inyl)aminophenylmethylcarbamate + TX, 2-Oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxazole-3-yl]phenyl]acetamide (this compound can be prepared by the method described in International Publication No. 2018 / 065414) + TX, 2-thiocyanate ethyl 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)quinoline + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethyl Indan-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-carbonitride (this compound may be prepared by the method described in International Publication No. 2016 / 156290) + TX,3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitride Ryl (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-oxazole-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-methyl-benzimidazole-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-oxazol-3-yl]phenyl]methyl]isoxazolidine-3-one + TX,4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX,4-[[6-[2-(2,4-difluorophenyl)-1, 1-Difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-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]pyridazine-3-one + TX, 4-chlorophenyl Nylsulfone + TX, 4-methyl(propane-2-inyl)amino-3,5-xylylmethylcarbamate + TX, 4-methylnonan-5-ol and 4-methylnonanan-5-one + TX, 5-(1,3-bbenzodioxo-l-5-yl)-3-hexylcyclohexa-2-enone + TX, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxazole-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-thiadiazinan-3-ylacetate TX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methylpyridazine-4-carboxamide (may be prepared by the method described in International Publication No. 2020 / 109391) + TX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide (may be prepared by the method described in International Publication No. 2020 / 109391) + 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 by the method described in International Publication No. 2020 / 109391) + TX,6-ethyl-5,7-dioxo-pyrrolo[4,5][1, 4] Dithiino[1,2-c]isothiazole-3-carbonitride+TX, 6-isopentylaminopurine+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, acetoprole+TX, acibenzolar+TX, acibenzolar-S-methyl+TX, acrylonitrile+TX, Adoxophyes Orana orana) GV+TX, Agrobacterium radiobacter+TX, Aldoxycarb+TX, Aldrin+TX, Allosamidin+TX, Alioxycarb+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 falcifera NPV + TX, Anagrus atomus + TX, Ancimidor + TX, Anilazine + TX, Anisifurupurine + TX, Anthraquinone + TX, Antu + TX, Aphelinus abdominalis + TX, Aphidius colemani colemani)+TX, Aphidoletes aphidimyza+TX, Aphorate+TX, Aramite+TX, Arsenous acid+TX, Atidathion+TX, Autographa californica NPV+TX, Azaconazole+TX, Azamethiphos+TX, Azobenzene+TX, Azothoate+TX, Azoxystrobin+TX, Bacillus sphaericus Neide+TX, Bacillus thuringiensis (Bacillus (thuringiensis) Delta Endotoxin + TX, Barium Carbonate + TX, Barium Hexafluorosilicate + TX, Barium Polysulfide + TX, Bartholin + TX, Bayer 22 / 190 + TX, Bayer 22408 + TX, Beauveria Bronnnyaltii + 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, Bioethanomethrin TX, Biopemethrin + TX, Bis(2-chloroethyl) Ether + TX, Bis(tributyltin) Oxide + TX, Bisadyl + TX, Bisthiosemi + TX,Vitertanol + TX, Bixafen + TX, Blastocydin-S + TX, Borax + TX, Bordeaux mixture + TX, Boscalid + TX, Brevicomin + TX, Brosifacum + TX, Brofenvalerate + TX, Bromadiolon + TX, Bromethalin + TX, Bromfenbinphos + TX, Bromoacetamide + TX, Bromocyclene + TX, Bromo-DDT + TX, Bromophos + TX, Bromopropylate + TX, Bromuconazole + TX, Bronopol + TX, Bufencarb + TX, Bupirimate + TX, Buprof Jedin + 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, Butocarboxyme + TX, Butonate + TX, Butopyronoxyl + TX, Butoxy(polypropylene glycol) + TX, Butoxycarboxyme + TX, Butylpyridaben + TX, Calcium arsenate + TX + TX, Calcium cyanide + TX, Polysulfide calcium + TX, Can Fechlor + TX, Captafor + TX, Captan + TX, Carbanolate + TX, Carbendazim + TX, Carbon Disulfide + TX, Carbon Tetrachloride + TX, Carbophenothion + TX, Carboxine + TX, Cartabone Hydrochloride + TX, CAS No. 2132414-04-9 + TX, CAS No. 2344721-61-3 + TX, Sebazin + TX, Quinomethionate + TX, Chloralose + TX, Chlorbenside + TX, Chlorbicyclene + TX, Chlordan + TX, Chlordecone + TX, Chlordimeform + TX, Chlordimeform Hydrochloride + TX X, Chlorphenetol + TX, Chlorfensone + TX, Chlorfensulfide + TX, Chlorbenzilate + TX, Chloroform + TX, Chloroinconazide + TX, Chloromebform + TX, Chloromethirone + TX, Chloroneb + ​​TX, Chlorophacinone + TX, Chloropicrin + TX, Chloropropylate + TX, Chlorthalonil + TX, Chlorfoxime + TX, Chlorprazofos + TX, Chlorthiofos + TX, Clozolinate + TX, Cholecalciferol + TX, Chrysoperla carnea + TX, Synerin I + TX, Synerin II + TX, Synerin + TX,Sysmethrin + TX, Sysmethrin + TX, Cith-resmethrin + TX, Crocitrin + TX, Closantel + TX, Chodrelua + TX, Chodremon + TX, Copper acetoarsenite + 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, Coumocrol + TX, Coumufuryl + TX, Coumaphos + TX, Coumatetralyl + TX, Cumethoxystrobin (Diaxiangjunzhi) + TX, Cumitoate + TX, Comoxystrobin + TX, Cresol + TX, Crimidine + TX, Crotamiton + TX, Clotoxyphos + TX, Clufomate + TX, Cryolite + TX, Cryptolaemus montorgiensis Montrouzieri) + TX, CS708 + TX, Curelure + TX, Cufraneb + ​​TX, Cyanophenphos + TX, Cyanophos + TX, Cyanophos + TX, Cyanthoate + TX, Cyazofamide + TX, Sibutrin + TX, Cicletorin + TX, Cyclobtrifluram + TX, Cydia pomonella GV + TX, Cyflufenaamide + TX, Simiazole + TX, Cymoxanil + TX, Cyproconazole + TX, Cyprodinil + TX, Cythioate + 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, Dicapton + TX, Dichlorobentiazox + TX, Diclofenthion + TX, Diclofluanide + TX, Dichloron + TX, Dichlorofen + TX, Dichlorvos + TX, Diclozoline + TX, Dicrifos + TX, Diclosimet + TX, Diclomedin + TX, Dichloran + TX, Dicresyl + TX, Dicyclanil + TX, Dicyclopentadiene + TX, Dierdrin + TX, Dienochlor + TX, Dietofencarb + TX, Diethyl 5-methylpyrazole 3-yl phosphate + TX, Diethyltoluamide + TX, Difenacum + TX, Difenoconazole + TX, Difethiaron + TX, Diflovidazine + TX, Diglyphus isaeaisaea)+TX, Dirol+TX, Dimatif+TX, Dimefluthrin+TX, Dimefluthrin+TX, Dimefox+TX, Dimethane+TX, Dimethilimol+TX, Dimethomorph+TX, Dimethrin+TX, Dimethyl carbonate+TX, Dimethyl phthalate+TX, Dimethylvinphos+TX, Dimethilane+TX, Dimoxystrobin+TX, Dynex+TX, Dynex-dicrexin+TX, Diniconasol+TX, Dinocap 4+TX, Dinocap-6+TX, Dinocton+TX, Dinopenton+TX, Dinoprop+TX, Dinosam+TX, Dinoseb+TX, Dinosulfone+TX, Dinoterbone+TX, Diophenolane+TX, Dioxabenzophos+TX, Dioxathion + TX, Diphacinone + TX, Diphenylsulfone + TX, Dipimethitron + TX, Dipirithione + TX, Disparlua + TX, Disulfiram + TX, Dithianone + TX, Diticlophos + TX, DNOC + TX, Dodeca-8-en-1-ylacetate + TX, Dodeca-9-en-1-ylacetate + TX, Dodeca-8 + TX, Dodemorph + TX, Dodicine + TX, Dodyne + TX, Dodyne + TX, Dofenapine + TX, Dominical + TX, Doramectin + TX, DSP + TX, d-Tetramethrin + TX, Ecdysterone + TX, Edifenphos + TX, EI1642 + TX, EMPC + TX, Encarsia formosa Eretmoceras formosa + TX, Endotar + TX, Endothion + TX, Enestrobrin + TX, Enoxastrobin + TX, EPBP + TX, Epoxyconazole + TX, Eprinomectin + TX, Eretmoceras elemicuseremicus)+TX, ergocalciferol+TX, ethafos+TX, etaboxam+TX, ethiofencarb+TX, etyrimol+TX, ethoate-methyl+TX, ethyl 1-[[4-[(Z)-2-ethoxy-3,3,3--trifluoropropa-1-enoxy]phenyl]methyl]pyrazole-3-carboxylate (which can 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 [I]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 may be prepared by the method described in International Publication No. 2018 / 158365) (ru) + TX, Ethyl 4-methyloctanoate + TX, Ethyl formate + TX, Ethyl hexanediol + TX, Ethylene dibromide + TX, Ethylene dichloride + TX, Ethylene oxide + TX, Etridiazole + TX, Etrimophos + TX, Eugenol + TX, EXD + TX, Famoxadone + TX, Farnesol + TX, Farnesol and Nerolidol + TX, Phenamidon + TX, Phenaminosulf + TX, Phenaminestrobin + TX, Phenarimol + TX, Phenazaflor + TX, Fenbuconazole + TX, Fenbutatin Oxy Do+TX, Fenchlorphos+TX, Phenetacarb+TX, Fenflam+TX, Fenhexamide+TX, Fenitrothion+TX, Phenothiocarb+TX, Phenoxacrim+TX, Phenoxanil+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, Ferbam+TX, Felimzon+TX, Ferric phosphate+TX, Furocumafen+TX, Floryl picoxamide+TX, Fluazinam+TX, Fluventeram+TX, Flubenzimine+TX, Flucoflon+TX, Flucycloxlon+TX, Fludioxonil+TX, Fluentyl+TX, Fluphenoxadiazam+TX, Fluphenoxystrobin+TX, Fluindapyr+TX, Flumethylsulfoli Mu + TX, Flumorph + TX, Fluopicolide + TX, Fluopimomid + TX, Fluopyram + TX, Fluorebenside + 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, Flutriafoll+TX, Fluxapiroxad+TX, FMC1137+TX, Forpet+TX, Formaldehyde+TX, Formetanate+TX, Formetanate hydrochloride+TX, Formparanate+TX, Fosetil-aluminum+TX, Fosmetil+TX, Fosspire+TX, Fosthietan+TX, Frontalin+TX, Fuberidazole+TX, Flalaxil+TX, Flamethopyr+TX, Flathiocarb+TX, Fretolin+TX , Furfural + TX, Gamma-HCH + TX, Gliodin + TX, Grandlure + TX, Grandlure I + TX, Grandlure II + TX, Grandlure III + TX, Grandlure IV + TX, Guazatine + TX, Guazatine acetate + TX, Halfenprox + TX, HCH + TX, Hemel + TX, Hempa + TX, HEOD + TX, Heptachlor + TX, Heterophos + TX, Heterorhabditis bacteriophora and H. megidis (H.megidis)+TX, hexaconazole+TX, hexadecylcyclopropanecarboxylate+TX, hexalua+TX, hexamide+TX, HHDN+TX, Hypodamia Convergence (concentrates) + TX, hydralgafen + TX, hydrated lime + TX, hydrogen cyanide + TX, himexazole + TX, hykincarb + TX, imanin + TX, imazalil + TX, imibenconazole + TX, iminoctadine + TX, impulfluxam + TX, ipconazole + TX, ipfentrifluconazole + TX, iflufenoquin + TX, iprobenphos + TX, iprodione + TX, iprovalicarb + TX, ipsdienol + TX, ipsenol + TX, IPSP + TX, isamidophos + TX, isazofos + TX, isobenzan + TX, isocarbophos + TX, isodrine + TX, Isophenphos + TX, Isofetamide + TX, Isoflucipram + TX, Isolan + TX, Isoprothiolan + TX, Isopyrazam + TX, Isothianil + TX, Isoxathion + TX, Japonila + 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 Dactylopii) + TX, Leptophos + TX, Lindan + TX, Linetin + TX, Lilimphos + TX, Littlea + TX, Lupula + TX, Rubenmixian + TX, Lithidathione + TX, Macrolophus caliginosus + TX, Magnesium phosphide + TX, Malonoben + TX, Mamestra brassicae NPV + TX, Mancopper + TX, Mancozeb + TX, Mandestrobin + TX, . Mandipropamide + TX, Maneb + ​​TX, Magidox + TX, m-Cumenylmethylcarbamate + TX, Mecarbam + TX, Mecarfon + TX, Medrua + TX, Mefentrifluconazole + TX, Megatomoic acid + TX, Menazone + TX, Mepanipyrim + TX, Meperfluthrin + TX, Mephosphorane + TX, Mepronil + TX, Mercury oxide + TX, Mercurous chloride + TX, Mesulfen + TX, Mesulfenphos + TX, Metalaxyl + TX, Metam + TX, Metam-potassium + TX, Metam-sodium + TX, Metaphycus helvolus + TX, Metarhizium anisopliae variety Acridam + TX, Metarhizium anisopliae variety Anisopliae var. anisoopliae) + TX, metaleel picoxamide + TX, metconazole + TX, metepa + TX, methacryphos + TX, methanesulfonyl fluoride + TX, metasulfocarb + TX, methiotepa + TX, metoclotophos + TX, methoprene + TX, metoquin-butyl + TX, metotrin + TX, methoxychlor + TX, methyl(Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxypropa-2-enoate + TX, methyl(Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxypropa-2-enoate (these compounds can be prepared by 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 by the method described in International Publication No. 2020 / 079111) + TX,Methyl(Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazole-2-yl]phenoxy]propane-2-enoate + TX, methyl aphorate + TX, methyl bromide + TX, methyl eugenol + TX, methyl isothiacyanate + TX, methyl N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazole-4-yl]-2-methyl-phenyl]methylcarbamate (which can be prepared by 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]methylcarbamate (described in International Publication No. 2020 / 097012) (Can be prepared by the method of) +TX, Methyl N-[[5-[4-(2,4-dimethylphenyl)triazole-2-yl]-2-methylphenyl]methylcarbamate +TX, Methyl chloroform TX, Methylene chloride TX, Methyl neodecanamide TX, Metrilam +TX, Metolcarb +TX, Metminostrobin +TX, Methoxadiazone +TX, Metraphenone +TX, Methyltetraprole +TX, MGK264 +TX, Milbemycin oxime +TX, Mipafox +TX, Mirex +TX, Monoclotophos +TX, Morphothion +TX, Morzide +TX, Moxidectin +TX, Mascala +TX, Mycrobutanil +TX, Mycrozoline +TX, Myrothecium bergaria 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 can be prepared by the methods described in International Publication Nos. 2017 / 055473, 2017 / 055469, 2017 / 093348 and 2017 / 118689), N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoroquinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoroquino Phosphorus-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 N-3-carboxamide + TX, N-[(E)-methoxyiminomethyl]-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-(difluoro (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-ylul)oxy-2,5-dimethylphenyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-l-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine (These compounds were prepared by the method described in International Publication No. 2015 / 155075) (This compound can be prepared by the method described in IPCOM000249876D) + 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 are described in International Publication No. 2018 / 202428) (These compounds can be prepared by the method described in International Publication No. 2018 / 228896) + TX, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine (These compounds can be prepared by the method described in International Publication No. 2018 / 228896) + TX, Nabam + TX, Naphthalophos + TX, Nared + TX, Naphthalene + TX, NC-170 + TX, Neodiprion sertifer NPV and N. lecontei NPV + TX, Nerolidol + TX, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]propanamide + TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetane-2-yl]phenyl]-N-methyl-formamidine + TX, bis(dimethyldithiocarbamic acid)nickel + 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, Nitrilacarb 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]benzenecarbothioamide + TX, Nylbormid + TX, Nualimol + TX, O,O,O',O'-tetrapropyldithiopyrophosphate + TX, Ok Tadeca-2,13-diene-1-ylacetate + TX, Octadeca-3,-diene-1-ylacetate + TX, Octylinone + TX, Oflas + TX, Oleic acid + TX, Omethoate + TX, Orflurua + TX, Orius spp. + TX, Orictalua + TX, Orysastrobin + TX, Ostramon + TX, Oxadixyl + TX, Oxamate + TX, Oxatiapiproline + TX, Oxolinophosphate + TX, Oxocarboxyne + TX, Oxideprophos + TX, Oxydisulfon + TX, Oxytetracycline + TX, Paclobutrazol + TX, Paecilomyces humosoroseus Phytoseiulus persimilis (Phytoseiulus persimilis) + TX, paradichlorobenzene + 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, PH60~38 + TX, phenamacryl + TX, phenakapton + TX, fosacetim + TX, phosalon + TX, phosdiphen + TX, phosphoran + TX, phosglycine + TX, fosniclor + TX, phosphamidone + TX, phosphine + TX, phosphorus + TX, phoxim-methyl + TX, phthalide + TX, Phytoseiulus persimilispersimilis)+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 arsenate+TX, potassium ethylxanoate+TX, potassium hydroxyquinoline sulfate+TX, potassium thiocyanate+TX, pp'-DDT+TX, procosen I+TX, procosen II+TX, procosen III+TX X, Primidophos+TX, Probenzarol+TX, Proclozas+TX, Proclonol+TX, Procymidone+TX, Profluthrin+TX, Promacil+TX, Promecarb+TX, Propamocarb+TX, Propiconazole+TX, Propineb+TX, Propoxul+TX, Propropyl isomer+TX, Proquinazide+TX, Protidathion+TX, Prothioconazole+TX, Prothiophos+TX, Protoate+TX, Pidiflumetofen+TX, Piraclostrobin+TX, Piramethostrobin+TX, Piraoxystrobin+TX, Pirapropoin+TX, Pyraziflumid + TX, Pyrazofos + TX, Pyrethmetrin + TX, Pyrethrin I + TX, Pyrethrin II + TX, Pyrethrin + TX, Pyribencarb + TX, Pyridaclomethyl + TX, Pyridafenthion + TX, Pyridine-4-amine + TX, Pyriphenox + TX, Pyrimethanil + TX, Pyrimate + TX, Pyrimorph + TX, Pyrinulone + TX, Pyriophenone + TX, Pyrisoxazole + TX, Pyrroquilon + TX, Quassia + TX, Quinalphos + TX, Quinalphos-methyl + TX, Quinoclamine + TX, Quinofumelin + TX, Quinonamide + TX, Quinothione + TX, Quinoxyfen + TX, Quinthiophos + TX, Quintozen + TX, R-1492 + TX, Lafoxanide + TX, Resmethrin + TX, Reynoutria saccharinensis Sachalinensis extract + TX, Ribavirin + TX, Rimetalaxyl + TX, Rotenone + TX, Lianya + TX, Lianodine + TX, S421 + TX, Sabajira + TX, Shuradan + TX, Siriloside + TX, Seboctilamine + TX, Cebuphos + TX, Sedaxane + TX, Selamectin + TX, Sesamex + TX, Sesamolin + 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, pentachlorophenoxide + TX, sodium selenate + TX, sodium tetrathiocarbonate + TX, sodium thiocyanate + TX, sofamide + TX, solzidine + TX, spiroxamine + TX, SSI-121 + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema feltiae + TX, Steinernema glaseri + TX, Steinernema riobrave + TX, Steinernema riobravis + TX, Steinernema scapteris (steinernemas)(Capterisci) + TX, Steinernema species (Steinernemaspp.) + 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, Te Bufloxin + TX, Tebupyrimphos + TX, Tecrophthalam + TX, Temephos + TX, Tepa + TX, TEPP + TX, Terarethrin + TX, Terbaum + 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, Thiabendazole + TX, Thiafenox TX, Thiapronil + TX, Cyclophos + TX, Tifluzamide + TX, Thiocarboxyme + TX, Thiocyclam + TX, Thiocyclam hydrogen 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, Thiram + T X, Thuringensine + TX, Thiazinyl + TX, Tolchlorophos-methyl + TX, Tolprocarb + TX, Trilfluanide + TX, Tralomethrin + TX, Transpermethrin + TX, Tretamine + TX, Triadimephone + TX, Triadimenol + TX, Triamiphos + TX, Triatene + TX, Triazamate + TX, Triazophos + TX, Triazooxide + TX, Triazurone + TX, Tributyltin oxide + TX, Trichlormethaphos 3 + TX, Trichloronat + TX, Tricogramma speciesspp.)+TX, Triclopyricarb+TX, Tricyclazole+TX, Tridemorph+TX, Triphenmorph+TX, Triphenophos+TX, Trifloxystrobin+TX, Triflumizole+TX, Triforin+TX, Trimedlua+TX, Trimedlua A+TX, Trimedlua B1+TX, Trimedlua B2+TX, Trimedlua C+TX, Trimetacarb+TX, Trinactin+TX, Trinexapac+TX, Triphenyltin acetate+TX, Triphenyltin hydroxide+TX, Triplen + TX, Triticonazole + TX, Trunc-call + TX, Typhlodromus occidentalis + TX, Uredepa + TX, Validamycin + TX, Valifenarate + TX, Vanidothion + TX, Vaniliprole + TX, Veratrine + TX, Veratrine + TX, Berbutin + TX, Verticillium lecanii + TX, Vinclozoline + TX, Warfarin + TX, XMC + TX, Xylenol + TX, Zeatin + TX, Zetametrine + TX, Zhongshengmycin + TX, Zinc naphthenate + TX, Zinc phosphide + TX, Zinc thiazole + TX, Zineb + ​​TX, Ziram + TX, Zolaprofos + TX, Acinetobacter lwoffii + TX, Acremonium alternatum + TX, Acremonium cephalosporium, 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 destruens (Alternaria destruens)(Smolder(registered trademark))+TX, Ampelomyces quisqualis(AQ10(registered trademark))+TX, Aspergillus flavus AF36(AF36(registered trademark))+TX, Aspergillus flavus NRRL21882(Aflaguard(registered trademark))+TX, Aspergillus spp.+TX, Aureobasidium pullulans+TX, Azospirillum (MicroAZ(registered trademark), TAZO B(registered trademark))+TX(registered trademark), Azotobacter+TX, Azotobacter croocuccum(Azotobacter Bacillus chroocuccum (Azotomeal®) + TX, Azotobacter cysts (Bionatural BloomingBlossoms®) + TX, Bacillus amyloliquefaciens + TX, Bacillus cereus (Bacilluscereus)+TX, Bacillus chitinosporus strain AQ746+TX, 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 (Bacillus Bacillus licheniformis) HB-2 strain (Biostart (trademark), formerly Rhizoboost (registered trademark)) + TX, Bacillus macerans + TX, Bacillus marismortui + TX, Bacillus megaterium + TX, Bacillus mycoides AQ726 strain + TX) + TX, Bacillus papillae (Milky Spore Powder (registered trademark)), Bacillus pumilus + TX, Bacillus pumilus AQ717 strain + TX, Bacillus pumilus GB34 strain (Yield Shield (registered trademark)) + TX, Bacillus pumilus pumilus)OST 2808 strains (Sonata (registered trademark), Bacillus sphaericus (VectoLex (registered trademark)) + TX, Bacillus genus species (Bacillus spp.) AQ175 strains + TX, Bacillus genus species (Bacillus spp.) AQ177 strains + TX, Bacillus spp. AQ178 strains + TX, Bacillus subtilis AQ153 strains + TX, Bacillus subtilis AQ743 strain, Bacillus subtilis QST713 strain (CEASE®, Serenade®, Rhapsody®) + TX, Bacillus subtilis QST 714 (JAZZ®) + TX, Bacillus subtilis QST3002 strains + TX, Bacillus subtilis QST3004 strain + TX, Bacillus subtilis var. amyloricephasiensisamyloliquefacie)FZB24 strain (Taegro®, Rhizopro®) + TX, Bacillus thuringiensis aizawai GC91 (Agree®) + TX, Bacillus thuringiensis Cry2Ae + TX, Bacillus thuringiensis israelensis (BMP123®, Aquabac®, VectoBac®) + TX, Bacillus thuringiensis krustaki (Bacillus thuringiensis Bacillus thuringiensis kurstaki (Javelin®, Deliver®, CryMax®, Bonde®, ScutellaWP®, TurilavWP®, Astuto®, DipelWP®, Biobit®, Foray®) + TX, Bacillus thuringiensis kurstaki BMP 123 (Baritone®) + TX, Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF / 3P®) + TX, Bacillus thuringiensis AQ52 strain + TX, Bacillus thuringiensis BD#32 strain + TX, Bacillus thuringiensis telebrionis (Bacillus thuringiensis tenebrionis (Novodor®, BtBooster) + TX, Bacillus thuringiensis var. aizawai (XenTari®, DiPel®) + TX, Bacteria species (bacteriaspp.)(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® + TX, Beauveria spp. + TX, Botrytis cineria + TX, 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 Candida butyri) + TX, Candida famata + TX, Candida fructus + TX, Candida glabrata + TX, Candida guilliermondii + TX, Candida melibiosica + TX, Candida oleophila strain O + TX, Candida parapsilosis + TX, Candida pelliculosa + TX, Candida pulcherrima + TX, Candida reukaufii + TX, Candida cytoana (Candida Candida saitoana (Bio-Coat®, Biocure®) + TX, Candida sake + TX, Candida spp.) + TX, Candida tenius + TX, Cedecea davisae + TX, Cellulomonas flavigena + TX, Chaetomium cochliodes (Nova-Cide®) + TX, Chaetomium globosum (Nova-Cide®) + TX, Chromobacterium subtsugae PRAA4-1T strain (Grandevo®) + TX, Cladosporium chlorocephalum + TX, Cladosporium cladosporioides + TX, Cladosporium oxysporum (Cladosporium oxysporum)+TX, Cladosporium spp.+TX, Cladosporium tenuissimum+TX, Clonostachys rosea (EndoFine®)+TX, Colletotrichum acutatum+TX, Coniothyrium minitans (CotansWG®)+TX, Coniothyrium spp.)+TX, Cryptococcus albidus (YIELDPLUS(registered trademark))+TX, Cryptococcus humicola+TX, Cryptococcus infirmo-miniatus+TX, Cryptococcus laurentii+TX, Cryptophlebia leucotreta granuvirus (Cryptex(registered trademark))+TX, Cupriavidus campinensis+TX, Cydia pomonella granuvirus (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®, BiofoxC®)+TX, Fusarium proliferatum+TX, Fusarium spp.+TX, Galactomyces geotrichum+TX, Gliocladium catenulatum (Primastop®, . Prestop(registered trademark))+TX, Gliocladium roseum+TX, Gliocladium spp. (SoilGard(registered trademark))+TX, Gliocladium virens (Soilgard(registered trademark))+TX, Granulovirus (Granupom(registered trademark))+TX, Halobacillus halophilus+TX, Halobacillus litoralis+TX, Halobacillus trueperi+TX, Halomonas spp.+TX, Halomonas subglaciescola+TX, Halovibrio variabilis+TX, Hanseniaspora ubarum uvarum)+TX, Helicoverpa armigera nuclear polyhedron virus (Helicovex®)+TX, Helicoverpa zea nuclear polyhedron virus (Gemstar®)+TX, Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus strain PFR-97®, PreFeRal®)+TX, isoflavone formononetin (Myconate®)+TX, Kloeckera apiculata+TX, 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, Lecanicillium longisporum (Vertiblast®)+TX, Lecanicillium muscarium (Vertikil®)+TX, Lymantria Dispar nuclear polyhedron disease virus (Disparvirus®)+TX, Marinococcus halophyllus halophilus)+TX, Meira geulakonigii+TX, Metarhizium anisopliae (Destruxin WP®)+TX, Trichopyrus (Metarhizium anisopliae) (Met52®)+TX, Metschnikowia fruticola (Shemer®)+TX, Metschnikowia pulcherrima+TX, Microdochium dimerum (Antibot®)+TX, Micromonospora coerulea+TX, Microsphaeropsis ochracea+TX, Muscodor albus albus)620(Muscudor(registered trademark))+TX, Muscodorroseus, especially strain A3-5 (accession number NRRL30548)+TX, Mycorrhizae spp.)(AMykor(registered trademark), RootMaximizer(registered trademark))+TX, Myrothecium verrucaria AARC-0255 strain (DiTera(registered trademark), BROSPLUS(registered trademark))+TX, Ophiostoma piliferum D97 strain (Sylvanex(registered trademark))+TX, Paecilomyces farinosus+TX, Paecilomyces lilacinus 251 strain (MeloConWG(registered trademark))+TX, Paecilomyces linacinus (BiostatWP(registered trademark))+TX, Paenibacillus polymixa polymyxa)+TX, Pantoea agglomerans (BlightBan C9-1(registered trademark))+TX, Pantoea species (Pantoeaspp.)+TX, Pasteuria nishizawae, especially Pn1 strain (CLARIVA (from Syngenta / ChemChina));+TX, Pasteuria species (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 frequentans) + TX, Penicillium griseofulvum + TX, Penicillium purpurogenum + TX, Penicillium spp.)+TX, Penicillium viridicatum+TX, Phlebiopsis gigantean (Rotstop®)+TX, Phosphate-soluble bacteria (Phosphomeal®)+TX, Phytophthora cryptogea+TX, Phytophthora palmivora (Devine®)+TX, Pichia anomala+TX, Pichia guilliermondii+TX, Pichia membranaefaciens+TX, Pichia onychis+TX, Pichia stipites (Pichia Pseudomonas stipites) + TX, 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 A506 strain (BlightBanA506®) + TX, Pseudomonas petida (Pseudomonas putida)+TX, Pseudomonas reactan s+TX, Pseudomonas spp.)+TX, Pseudomonas syringae (Bio-Save®)+TX, Pseudomonas viridiflava+TX, Pseudozyma flocculosa PF-A22UL strain (SporodexL®)+TX, Puccinia canaliculata+TX, Puccinia thlaspeos (WoodWarrior®)+TX, . Pythium paroecandrum + TX, Pythium oligandrum (Polygandron®, Polyversum®) + TX, Pythium periplocum + TX, Rhanella aquatilis + TX, Rhanella spp. + TX, Rhizobia (Dormal®, Vault®) + TX, Rhizoctonia + TX, Rhodococcus globerulus AQ719 strain + TX, Rhodosporidium diobovatum + TX, Rhodosporidium torroides (Rhodosporidium toruloides)+TX, Rhodotorula glutinis+TX, Rhodotorula graminis+TX, Rhodotorula mucilagnosa+TX, Rhodotorula rubra+TX, Rhodotorula spp.+TX, Saccharomyces cerevisiae+TX, Salinococcus roseus+TX, Sclerotinia minor (SARRITOR®)+TX, Sclerotinia minor+TX, Scytalidium spp.+TX, Scytalidium urezinicola uredinicola)+TX, Serratia marcescens+TX, Serratia plymuthica+TX, Serratia species (Serratiaspp.)+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 *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, . Tilletiopsis species (Tilletiopsis spp.) + TX, Trichoderma asperellum (T34 Biocontrol®) + TX, Trichoderma atroviride (Plantmate®) + TX, Trichoderma gamsii (Tenet®) + TX, Trichoderma hamatum TH382 + TX, Trichoderma harzianum rifai (Mycostar®) + TX, Trichoderma harzianum (Trichoderma Trichoderma harzianum)T-22(Trianum-P(registered trademark), PlantShieldHC(registered trademark), RootShield(registered trademark), Trichoderma-G(registered trademark)+TX, Trichoderma harzianum T-39(Trichodex(registered trademark))+TX, Trichoderma inhamatum+TX, Trichoderma koningii+TX, Trichoderma lignorum+TX, Trichoderma longibrachiatum+TX, Trichoderma polysporum(BinabT(registered trademark))+TX, 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 ICC080 strain (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 (NaturalII®)+TX, various fungi (Millennium Microbes®)+TX, Verticillium chlamydosporium+TX, Vip3Aa20 (VIPtera®)+TX, Virgibaclillus marismortzii marismortui)+TX, Xanthomonas campestris pv. Poae (Camperico®)+TX, Xenorhabdfus bovienii+TX, Xenorhabdus nematophilus+TX, . AGNIQUE® MMF + TX, Azadirachtin (PlasmaNeemOil®, AzaGuard®, MeemAzal®, MOLT-X®, e.g., AZATINXL from Certis, US) + TX, Plant IGR (Neemazad®, Neemix®) + TX, BugOil + TX, Canola Oil (LillyMillerVegol®) + TX, Chenopodium amuibrosioides (C), a close relative of the genus Chenopodium. Henopodium ambrosioides (Requiem®) + TX, Chrysanthemum extract (Crisant®) + TX, Labiatae essential oil (Botania®) + TX, Neem oil extract (Trilogy®) + TX, Clove, rosemary, peppermint and thyme oil extract (Garden Insect Killer) + TX, Garlic + TX, Glycine betaine (Greenstim®) + TX, Kaolin (Screen®) + TX, Lemongrass oil (GreenMatch®) + TX X, Melaleuca alternifolia extract (also known as tea tree oil) (TimorexGold®) + TX, Clove peppermint garlic oil and mint mixture (SoilShot®) + TX, Clove rosemary and peppermint extract mixture (EF400®) + TX, Rosemary, sesame, peppermint, thyme and cinnamon extract mixture (EF300®) + TX, Neem oil + TX, Nepeta cataria a) Catnip oil + TX, Nepeta catataria + TX, Nicotine + TX, Oregano oil (MossBuster®) + TX, Pedaliaceae oil (Nematon®) + TX, Pine oil (Retenol®) + TX, Pyrethrum + TX, Quillaja saponaria (NemaQ®) + TX, Reynoutria sachalinensis (Regalia®),Sakalia (registered trademark) + TX, Rotenone (EcoRoten (registered trademark)) + TX, Rutaceae plant extract (Soleo (registered trademark)) + TX, Soybean oil (Orthoecosense (registered trademark)) + TX, Brown algae storage glucam (Laminarin (registered trademark)) + 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 calihornicus californicus) (Amblyline(registered trademark), Spical(registered trademark)) + TX, Amblyseius cucumeris (Thripex(registered trademark), Bugline cucumeris(registered trademark)) + TX, Amblyseius Fallacis(registered trademark)) + TX, Amblyseius swirskii (Bugline swirskii(registered trademark), Swirskii-Mite(registered trademark)) + TX, Amblyseius womersleyi (WomerMite(registered trademark)) + TX, Amitus hesperidum + TX, Anagrus atomus + TX, Anagyrus fusciventris + TX, Anagyrus kamali+TX, Anagyrus loecki+TX, Anagyrus pseudococci(Citripar(R))+TX, Anicetus benefices+TX, Anisopteromalus calandrae+TX, Anthocoris nemoralis(Anthocoris-System(R))+TX, AphelinusAphytis abdominalis (Apheline®, Aphiline®), +TX, Aphelinus asychis +TX, Aphidius colemani (Aphipar®) +TX, Aphidius ervi (Aphelinus-System®) +TX, Aphidius ervi (Ervipar®) +TX, Aphidius gifuensis +TX, Aphidius matricariae (Aphipar-M®) +TX, Aphidoletes aphidimyza (Aphidend®, Aphidoline®) +TX, Aphytis lingnanensis +TX, Aphytis melinus (Aphytis melinus)+TX, Aprostocetus hagenowii+TX, Atheta coriaria (Staphyline®)+TX, Bombus spp.+TX, Bombus terrestris (Beeline®, Tripol®)+TX, Bombusterrestris (NatupolBeehive®)+TX, Cephalonomia stephanoderis+TX, Chilocorus nigritus+TX, Chrysoperla carnea (Chrysoline®, Chrysopa®)+TX, Chrysoperla rufirabris (Chrysoperla rufilabris)+TX, Cirrospilus ingenuus+TX, Cirrospilus quadristriatus+TX, Citrosticus philochnistoidesphyllocnistoides)+TX, Closteroceruschamaeleon+TX, Closterocerus spp.+TX, Coccidoxenoides perminutus (Planopar®)+TX, Coccophagus cowperi+TX, Coccophagus lycimnia+TX, Cotesia flavipes+TX, Cotesia plutellae+TX, Cryptolaemus montrouzieri (Cryptobug®+TX, Cryptoline®)+TX, Cybocephalus nipponicus)+TX, Dacnusasibirica (Minusa®, DacDigline®, Minex®) + TX, Delphastus catalinae (Delphastus®) + TX, Delphastus pusillus + TX, Diachasmimorpha krausii + TX, Diachasmimorpha longicaudata + TX, Diaparsis jucunda + TX, Diaphorencyrtus aligarhensis + TX, Diglyphus isaea) (Diminex(registered trademark), Miglyphus(registered trademark), Digline(registered trademark)) + TX, Diversinervus spp. + TX, Encarsia citrina + TX, Encarsia formosa (Encarsia max(registered trademark) + TX, Encarline(registered trademark) + TX, En-Strip(registered trademark)) + TX, Encarsia guadeloupae + TX, Encarsia haitiensis + TX, Episyrphus balteatus (Syrphidend(registered trademark)) + TX, Eretmoceris siphonini + TX, Eretmocerus californicus californicus)+TX, desert parasitic wasp (Eretmocerus eremicus) (Enermix(registered trademark), Ercal(registered trademark), Eretlinee(registered trademark), Bemimix(registered trademark))+TX, Eretmocerus hayati+TX, Eretmocerus mundus (Eretmocerusmundus) (Bemipar®, Eretlinem®) + TX, Eretmocerus siphonini + TX, Exochomus quadripustulatus + TX, Feltiella acarisuga (Spidend®) + TX, Feltiella acarisuga (Spidend®) + TX, Fopius arisanus + TX, Fopius ceratitivorus + TX, Hormononetin (Wirless Beehome®) + TX, Franklinothrips vespiformis (Vespop®) + TX, Galendromus osidentalis occidentalis)+TX, Goniozus legneri+TX, Habrobracon hebetor+TX, Harmonia axyridis (HarmoBeetle®)+TX, Heterorhabditis bacteriophora (NemaShieldHB®, Nemaseek®, Terranem-Nam®, Terranem®, Larvanem®, B-Green®, NemAttack®, Nematop®)+TX, Heterorhabditis spp. (Lawn Patrol®)+TX, Hippodamia convergens)+TX, Hypoaspisaculeifer (Aculeifer-System(registered trademark), Entomite-A(registered trademark))+TX, Hypoaspis miles (Hypolinem(registered trademark), Entomite-M(registered trademark))+TX, Lubalia leucospoides (LbaliaLeucospoides) + TX, Lecanoideus floccissimus + TX, Lemophagus errabundus + TX, Leptomastidea abnormis + TX, Leptomastix dactylopii (Leptopar®) + TX, Leptomastix epona + TX, Lindorus lophanthae + TX, Lipolexis oregmae + TX, Lucilia caesar (Natufly®) + TX, Lysiphlebus testaceus testaceipes)+TX, Macrolophus caliginosus (Mirical-N(registered trademark), Macrolinec(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-I®, Orilinei®) + TX, Orius laevigatus (Thripor-L®, Orilinel®) + TX, Orius majusculus (Orilinem®) + TX, Orius strigicollis (Thripor-S®) + TX, Pauesia juniperorum Juniperorum) + TX, Pediobius foveolatus + 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 trixspis (Pseudacteon tricuspis)+TX, Pseudaphycus maculipennis+TX, Pseudleptomastix mexicana+TX, Psyllaephagus pilosus+TX, Psyttalia concolorconcolor) (complex) + TX, Quadrastichus spp. + TX, Rhyzobius lophanthae + TX, Rodolia cardinalis + TX, Rumina decollate + TX, Semielacher petiolatus + TX, Sitobion avenae (Ervibank®) + TX, Steinernema carpocapsae (Nematac C®, Millenium®, BioNem C®, NemAttack®, Nemastar®, Capsanem®) + TX, Steinernema feltiae (NemaShield®, Nemasys) F (registered trademark), BioNem F (registered trademark), Steinernema-System (registered trademark), NemAttack (registered trademark), Nemaplus (registered trademark), Exhibitlines f (registered trademark), Scia-rid (registered trademark), Entonem (registered trademark)) + TX, Steinernema kraussei (Nemasys L (registered trademark), BioNe L (registered trademark), Exhibitline srb (registered trademark)) + TX, Steinernema riobrave (BioVector (registered trademark), BioVektor® + TX, Steinernema scapterisci (NematacS®) + TX, Steinernema spp. + TX, Steinernematid spp. (Guardian Nematodes®) + TX, Stethorus punctillum (Stethorus®) + TX, Tamarixia radiate + TX, Tetrastichus setifer + TX, Thripobius semiluteus + TX, Torymus sinensis + TX, Egg parasitic wasp (Trichogramma brassicae)(Tricholineb(registered trademark))+TX, egg parasitic wasp (Trichogramma brassicae)(Tricho-Strip(registered trademark))+TX, armyworm egg parasitoid wasp (Trichogramma evanescens)+TX, Tricogramma minutum+TX, corn borer egg parasitoid wasp (Trichogramma ostriniae)+TX, Tricogramma platneri+TX, Tricogramma pretiosum+TX, yellow-legged flat wasp (Xanthopimpla stemmator)+TX, Abscisic acid + TX, Aminomite (registered trademark) + TX, BioGain (registered trademark) + TX, bioSea (registered trademark) + TX, CAS number 2643947-26-4 + TX, Chondrostereum purpureum (Chontrol Paste (registered trademark)) + TX, Colletotrichum gloeosporioides (Collego (registered trademark)) + TX, Copper octanoate (Cueva (registered trademark)) + TX, Delta Trap (Trapline d (registered trademark)) + TX, Erwinia amylovora (Harpin) (ProAct (registered trademark)) + TX, 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, homo-brassonolide+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®) + TX, Nosema locustae (Semaspore Organic Grasshopper Control®) + TX, Pheromone trap (Thripline ams®) + TX, Potassium bicarbonate (MilStop®) + TX, Potassium iodide + potassium thiocyanate (Enzicur®) + TX, Potassium salt of fatty acid (Sanova®) + TX, Potassium silicate solution (Sil-Matrix®) + TX, Spider venom + TX, Sticky trap (Trapline YF® + TX, Rebell Amarillo®) + TX, SuffOil-X® + TX, Trap (Takitrapline y+b®) + TX, Bacillus mojavensis strain R3B (accession number NCAIM(P)B001389) (International Publication No. 2013 / 034938) + TX from Certis USA LLC, Bacillus pumilus strain BU F-33 (from BASF, CARTISSA®, EPA registration number 71840-19) + TX with NRRL accession number 50185, Bacillus subtilis CX-9060 from Certis USA LLC, Bacillus species Bacillus subtilis (sp.), particularly strain D747 (available from Kumiai Chemical Industry Co. as DOUBLENICKEL®) with accession number FERMBP-8234 (US Patent No. 7,094,592) + TX, Bacillus subtilis (Bacillus subtilis) strain BU1814 (VELONDIS® PLUS, VELONDIS® FLEX and VELONDIS® EXTRA from BASF SE) + TX, Bacillus subtilis var. Amyloliquefaciens (Bacillus subtilis var. Amyloliquefaciens) strain FZB24 (available from Novozymes as TAEGRO® or TAEGRO® ECO) with accession number DSM10271 (EPA registration number 70127-5) + TX, Bacillus subtilis Paenibacillus subtilis), particularly strain QST713 / AQ713 (having NRRL accession number B-21661, described in U.S. Patent No. 6,060,051, and available from Bayer CropScienceLP, U.S. as SERENADE® OPTI or SERENADE® ASO) + TX, Paenibacillus polymyxa, particularly strain AC-1 (e.g., TOPSEEED® from Green Biotech Company Ltd.) + TX, Paenibacillus species (Paenibacillus sp.) having accession number NRRL B-50972 or accession number NRRL B-67129.) strain (International Publication No. 2016 / 154297) + TX, Pantoea agglomerans, in particular strain E325 (Accession No. NRRL B-21856) (available from Northwest Agri Products as BLOOMTIMEBIOLOGICAL® FD BIOPESTICIDE) + TX, Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena) + TX, etc. Aureobasidium pullulans + TX, especially spores of strain DSM14940 + TX, spores of strain DSM14941 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, especially Lesaffre et al. Strains from Compagnie, FR, CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938 or CNCM No. 1-3939 (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 MBI110) (NRRL accession number B-50768, International Publication No. 2014 / 028521) (STARGUS® from Marrone Bio Innovations) + TX, Bacillus amyloliquefaciens strain FZB42, accession number DSM 23117 (ABiTEP, available from DE as RHIZOVITAL® registered trademark) + TX, Bacillus amyloliquefaciens, especially strain D747 (Kumiai Chemical Industry Co., Ltd.)Available from Double Nickel (trademark), with accession number FERM BP-8234, U.S. Patent No. 7,094,592) + TX, Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (QUARTZO (registered trademark) (WG) and PRESENCE (registered trademark) (WP) from FMC Corporation + TX, Bacillus licheniformis, in particular SB3086 (with accession number ATCC55406, International Publication No. 2003 / 000051) (available from Novozymes as ECOGUARD (registered trademark) Biofungicide and GREEN RELEAF (trademark)) + TX, Bacillus methylotrophicus strain BAC-9912 (Chinese Academy of Sciences (from Sciences' Institute of Applied Ecology) +TX, Bacillus mycoides isolate with accession number B-30890 (available from Certis USA LLC as BMJ TGAI® or WG and LifeGardt®) +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®, with accession number NRRL B-30087, described in U.S. Patent No. 6,245,551) +TX, Bacillus subtilis CX-9060 +TX from Certis USA LLC, Bacillus subtilis (Bacillus (subtilis) IAB / BS03 (AVIV (trademark) from STK Bio-Ag Technologies, PORTENTO (registered trademark) from Idai Nature) + TX, . Bacillus subtilis KTSB strain (FOLIACTIVE® from Donaghys) + TX, Bacillus subtilis BU1814 strain (available from BASF SE as VELONDIS® PLUS, VELONDIS® FLEX and VELONDIS® EXTRA) + TX, Bacillus subtilis GB03 strain (available from Bayer AG, DE as Kodiak®) + TX, Bacillus subtilis MBI 600 strain (available from BASF SE as SUBTILEX), accession number NRRL B-50595, U.S. Patent No. 5,061,495 + TX, Bacillus subtilis Bacillus subtilis) Y1336 strain (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 FZB24 strain (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5)) + TX, Bacillus subtilis) 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, BASF From SE: Paenibacillus epiphyticus (International Publication No. 2016 / 020371) + TX, From BASF SE: Paenibacillus polymyxa ssp. plantarum.Plantarum) (International Publication No. 2016 / 020371) + TX, Paenibacillus sp. (International Publication No. 2016 / 154297) + TX with registration number NRRL B-50972 or accession number NRRL B-67129, Pseudomonas chlororaphis strain AFS009, International Publication No. 2017 / 019448 (e.g., AgBiome Innovations, HOWLER (trademark) and ZIO (registered trademark) from the US) + TX, Pseudomonas chlororaphis Chloraphis), particularly strain MA342 (e.g., CEDOMON®, CERALL®, and CEDRESS® by Bioagri and Koppert) + TX, Pseudomonas fluorescens A506 (e.g., BLIGHTBAN® A506 by NuFarm) + TX, Pseudomonas proradix (e.g., PRORADIX® by Sourcon Padena) + TX, Streptomyces griseoviridis K61 (also known as Streptomyces galbus K61) (Accession number DSM 7206) (MYCOSTOP® from Verdera, PREFENCE® from BioWorks, cf. Crop Protection) (2006, 25, 468-475) + TX, Streptomyces lydicus WYEC108 strain (also known as Streptomyces lydicus WYCD108US strain) (ACTINO-IRON® and ACTINOVATE® from Novozymes) + TX, . Trichoderma atroviride T11 strain (IMI352941 / CECT20498) + TX, Ampelomyces quisqualis AQ10 strain (e.g., AQ10® by IntrachemBio Italia) + TX with accession number CNCM 1-807, Ampelomyces quisqualis especially AQ10 strain (e.g., AQ10® by IntrachemBio Italia) + TX, Aspergillus flavus NRRL21882 strain (product known as AFLA-GUARD® from Syngenta / ChemChina) + TX, Aureobasidium pullulans Aureobasidium pullulans, especially blastocysts of strain DSM14941 + TX, Aureobasidium pullulans, especially strain DSM14940 + TX, Aureobasidium pullulans, especially a mixture of blastocysts of strains DSM14940 and DSM14941 (e.g., Botector® by bio-ferm, CH) + TX, Chaetomium cupreum (accession number CABI353812) (e.g., BIOKUPRUM® by AgriLife) + TX, Chaetomium globosum (available as RIVADIOM® by Rivale) + TX, Cladosporium cladospolioides with accession number BS122244 Coniothyrium cladosporioides) H39 strain, U.S. Patent Application Publication No. 2010 / 0291039 (by Stichting Dienst Landbouwkundig Onderzoek) + TX, Coniothyrium minitans, in particular CON / M / 91-8 strain (accession number DSM9660, e.g., Bayer CropScience Biologics)Contans(registered trademark) from GmbH +TX, Cryptococcus flavescens strain 3C (NRRL Y-50378), +TX, Dactylaria candida dilophosphora alopecuri (available as TWIST FUNGUS(registered trademark)), Fusarium oxysporum Fo47 (available as FUSACLEAN by Natural Plant Protection) +TX, Gliocladium catenulatum (synonym: Clonostachys rosea f. catenulate J1446 (e.g., Prestop(registered trademark) by Lallemand)) +TX, Gliocladium roseum Chlonostachys 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 Chlonostachys rosea f. rosea) + TX, especially strain 321U from Adjuvants Plus, Xue AG (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root tot complex of field pea + TX, Can Jour Plant Science)ACM941+TX, Metschnikowia fructicola, particularly NRRL Y-30752+TX, Microsphaeropsis ochracea, Penicillium steckii (DSM 27859, International Publication No. 2015 / 067800)+TX from BASF SE, Trichoderma asperellum ICC 012 strain (also known as Trichoderma harzianum ICC012) with accession number CABI CC IMI 392716, and accession number IMI Mixture with Trichoderma gamsii (formerly T. viride) ICC 080 strain (e.g., BIO-TAM® from Isagro USA, Inc. or BIODERMA® by Agrobiosol de Mexico, SA de CV) containing 392151 + TX, Penicillium vermiculatum + TX, Phlebiopsis gigantea VRA1992 strain (ROTSTOP® C from Danstar Ferment) + TX, Pseudozyma flocculosa PF-A22UL strain (available as SPORODEX® L by Plant Products Co., CA) + TX, Saccharomyces cerevisiae Saccharomyces cerevisiae) LAS117 cell wall (CEREVISANE® from Lesaffre, ROMEO® from BASF SE) + TX, Saccharomyces cerevisiae from Lesaffre et Compagnie, FRSaccharomyces 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, especially strain LASO2 (from Agro-Levures et Derives) + TX, Simplicillium lanosoniveum + TX, strain T34 (e.g., T34 Biocontrol by Biocontrol Technologies S.L., ES) or ICC 012 strain from Isagro + TX, strain WRL-076 (NRRL Y-30842), U.S. Patent No. 7,579,183 + TX, Talaromyces flavus flavus)V117b strain + TX, Trichoderma asperelloides JM41R (accession number NRRLB-50759) (TRICHOPLUS® from BASFSE) + TX, Trichoderma asperellum, in particular SKT-1 with accession number FERMP-16510 (e.g., ECO-HOPE® from Kumiai Chemical Industry) + TX, Trichoderma asperellum, in particular kd strain (e.g., T-Grofrom from Andermatt Biocontrol) + TX, Trichoderma atroviride 77B strain (T77 from Andermatt Biocontrol) + TX, Trichoderma atroviride ATCC20476 strain (IMI 206040)+TX, Trichoderma atroviride LC52 strain (e.g., Tenet by Agrimm Technologies Limited)+TX, Trichoderma atroviride LU132 strain (e.g., Agrimm TechnologiesSentinel Limited +TX, Trichoderma atroviride NMI No. V08 / 002388 strain +TX, Trichoderma atroviride NMI No. V08 / 002389 strain +TX, Trichoderma atroviride NMI No. V08 / 002390 strain +TX, Trichoderma atroviride No. V08 / 002387 strain +TX, Trichoderma atroviride SKT-1 strain (FERM P-16510), Japanese Patent Publication No. 11-253151 +TX, Trichoderma atroviride KT-2 strain (FERM P-16511), Japanese Patent Publication No. 11-253151 + TX, Trichoderma atroviride SKT-3 strain (FERM P-17021), Japanese Patent Publication No. 11-253151 + TX, Trichoderma atroviride, particularly strain SC1 (accession number CBS122089, International Publication No. 2009 / 116106 and U.S. Patent No. 8,431,120 (from Bi-PA)) + TX, Trichoderma atroviride CNCM 1-1237 strain (e.g., Agrauxine, Esquive® WP from FR) + TX, Trichoderma fertile (e.g., product TrichoPlus from BASF) + TX, Trichoderma gamsii (formerly T. viride) + TX, Trichoderma gamsii (formerly T. viride) ICC ICC080 strain (IMI CC 392151 CABI) (available as BIODERMA® by AGROBIOSOL DE MEXICO, SADE CV) + TX, Trichoderma gamsii ICC080 strain (IMI CC 392151 CABI, BioDerma by AGROBIOSOL DE MEXICO, SADE CV), + TX, Trichoderma harmatum + TX, Trichoderma harmatum + TX with accession number ATCC28012, Trichoderma harzianum + TX, Trichoderma harzianum rifai Trichoderma harzianum strain T39 (e.g., Makhteshim, Trichoderma® from the US) + TX, Trichoderma harzianum strain Cepa SimbT5 (from Simbiose Agro), + TX, Trichoderma harzianum strain DB103 (available from Dagutat Biolab as T-GRO® 7456) + TX, Trichoderma harzianumTrichoderma harzianum ITEM 908 strain (e.g., Trianum-P from Koppert) + TX, Trichoderma harzianum T-22 strain (e.g., Trianum-P from Andermatt Biocontrol or Koppert) + TX, Trichoderma harzianum TH35 strain (e.g., Root-Pro by Mycontrol) + TX, Trichoderma polysporum IMI206039 strain (e.g., BINABBio-InnovationAB, Binab TFWP by Sweden) + TX, Trichoderma stromaticum with accession number Ts3550 (e.g., Tricovab by CEPLAC, Tricovab by Brazil) + TX, Trichoderma virens Trichoderma virens (also known as Gliocladium virens), particularly strain GL-21 (e.g., SoilGard by Certis, US) + TX, Trichoderma virens G-41 strain (accession number ATCC 20906) (e.g., ROOTSHIELD® PLUS WP and TURFSHIELD® PLUS WP from BioWorks, US) + TX, Trichoderma viride, particularly strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161:125-137) + TX, Trichoderma viride Ulocladium oudemansii U3 strain (e.g., Botry-Zen Ltd+TX, New) with accession number NM99 / 06216, TV1 strain (e.g., Trianum-P by Koppert) + TX.BOTRY-ZEN® by Zealand and BOTRYSTOP® from BioWorks, Inc. +TX, Verticillium albo-atrum (formerly V. dahliae) WCS850 strain with accession number WCS850 deposited with the Central Bureau for Fungi Cultures (e.g., DUTCH TRIG® by Tree Care Innovations) +TX, Verticillium chlamydosporium +TX, A mixture of Azotobacter vinelandii and Clostridium pasteurianum (available from Agrinos as INVIGORATE®) + TX, a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available from FMC Corporation as QUARTZO® (WG), PRESENCE® (WP)) + TX, Azorhizobium caulinodans, especially strain ZB-SK-5 + TX, Azospirillum brasilense (e.g., VIGOR® from ALO, Inc.) + TX, Azospirillum lipoferum Bacillus lipoferum (e.g., VERTEX-IF(trademark) from TerraMax, Inc.) + TX, Azotobacter chroococcum, especially strain H23 + TX, Azotobacter vinelandii, especially ATCC 12837 + TX, Bacillus amyloliquefaciens BS27 (accession number NRRLB-5015) + TX, Bacillus amyloliquefaciens, especially strain FZB42 (e.g., RHIZOVITAL(trademark) from BiTEP, DE) + TX, Bacillus amyloliquefaciens Bacillus amyloliquefaciens), especially strain IN937a + TX, Bacillus amyloliquefaciens pm414 (Biofilm CropLOLI-PEPTA(registered trademark) from Protectionkarano + TX, Bacillus amyloliquefaciens SB3281 (ATCC#PTA-7542, International Publication No. 2017 / 205258) + TX, Bacillus amyloliquefaciens TJ1000 (available from Novozymes as QUIKROOTS(registered trademark)) + TX, Bacillus cereus family member EE128 (NRRL No. B-50917) + TX, Bacillus cereus family member EE349 (NRRL No. B-50928) + TX, Bacillus cereus, especially strain BP01 (ATCC55675, e.g., Arysta) MEPICHLOR® from Lifescience, US +TX, Bacillus mycoides BT155 (NRRL No. B-50921) +TX, Bacillus mycoides BT46-3 (NRRL No. B-50922) +TX, Bacillus mycoides EE118 (NRRL No. B-50918) +TX, Bacillus mycoides EE141 (NRRL No. B-50916) +TX, Bacillus pumilus, especially strain GB34 (e.g., YIELDSHIELD® from Bayer Crop Science, DE) +TX, Bacillus pumilus Bacillus pumilus, especially strain ST2808 (accession number NRRL number B-30087) + TX, Bacillus siamensis, especially strain KCTC 13613T + TX, Bacillus subtilis, especially strain AQ30002 (accession number NRRL number B-50421 and described in U.S. Patent Application No. 13 / 330,576) + TX, Bacillus subtilis, especially strain AQ30004 (described in NRRL number B-50455 and U.S. Patent Application No. 13 / 330,576) + TX, Bacillus subtilis, especially strain MBI600 (e.g., SUBTILEX® from BASF SE) + TX, Bacillus subtilis rm303 (RHIZOMAX® from Biofilm Crop Protection) + TX, Bacillus subtilis BU1814 (available from BASF SE as TEQUALIS®) + TX, Bacillus tequilensis, especially strain NII-0943 + TX, Bacillus thuringiensis Bacillus thuringiensis BT013A (NRRL number B-50924), also known as 4Q7, +TX; Bradyrhizobium japonicum (e.g., OPTIMIZE® from Novozymes) +TX; Delftia acidovorans, especially strain RAY209 (e.g., BIOBOOST® from Brett Young Seeds) +TX; Lactobacillus sp. (e.g., LACTOPLANT® from LactoPAFI) +TX; Mesorhizobium cicer (e.g., NODULATOR from BASF SE) +TX; Paenibacillus polymixa polymyxa), especially strain AC-1 (e.g., Green BiotechCompany Ltd.)TOPSEED® +TX, Pseudomonas aeruginosa, especially strain PN1 +TX, Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena) +TX, Rhizobium leguminosarium biovar viciae (e.g., NODULATOR from BASF SE) +TX, Rhizobium leguminosarum, especially strain Z25 of bv. viceae (accession number CECT4585) +TX, Serratia marcescens, especially strain SRM (accession number MTCC8708), +TX, Sinorhizobium meliloti)NRG-185-1 strain (NITRAGIN® GOLD from Bayer CropScience) + TX. Thiobacillus species (e.g., CROPAID® from Cropaid Ltd UK) + TX, Myrothecium verrucaria AARC-0255 strain (e.g., DiTera® from Valent Biosciences) + TX, Penicillium bilaii ATCC22348 strain (e.g., JumpStart® from Acceleron BioAg) + TX, Penicillium bilaii ATCC ATCC20851 strain + TX, Purpureocillium lilacinum (formerly known as Paecilomyces lilacinus) 251 strain (AGAL89 / 030550, e.g., BioAct from Bayer CropScience Biologics GmbH) + TX, Pythium oliligandrum Pythium oligandrum (DV74 strain) + TX, Pythium oligandrum (M1 strain) (ATCC38472, 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 (V117b strain) + TX, Trichoderma asperellum strain (Eco-T from Plant Health Products, ZA) + TX, Trichoderma asperellum (Trichoderma Trichoderma atroviride, specifically strain V08 / 002387 + TX, Trichoderma atrovirideTrichoderma atroviride) CNCM1-1237 strain (e.g., Agrauxine, Esquive® WP from FR) + TX, Trichoderma atroviride LC52 strain (also known as Trichoderma atroviride LU132, e.g., Sentinel from Agrimm Technologies Limited) + TX, Trichoderma atroviride NMI No. V08 / 002388 strain + TX, Trichoderma atroviride NMI No. V08 / 002389 strain + TX, Trichoderma atroviride NMI No. V08 / 002390 strain + TX, Trichoderma atroviride atroviride) SC1 strain (described in International Publication No. 2009 / 116106) + TX, Trichoderma harzianum 1295-22 strain + TX, Trichoderma harzianum ITEM 908 strain + TX, Trichoderma harzianum T-22 strain (e.g., Trianum-P from Andermatt Biocontrol or Koppert) + TX, Trichoderma harzianum TSTh20 strain + TX, Trichoderma harzianum GI-3 strain + TX, Trichoderma virens (Trichoderma virens) GL-21 strain (e.g., SoilGard® from Certis, USA) + TX, Trichoderma viride B35 strain (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161:125-137) + TX, Verticillium albo-atrum (formerly V. dahliae) WCS850 strain (CBS 276.92, e.g., Tree Care)Dutch Trig) + TX from Innovations, Agrobacterium radiobacter K84 strain (Galltrol from AgBiochem Inc.), +TX, Bacillus amyloliquefaciens, especially strain PTS-4838 (e.g., Valent Biosciences), AVEO from the US), +TX, Bacillus mycoides, isolate J. (e.g., BmJ from Certis USA LLC), +TX, Bacillus sphaericus, in particular serotype H5a5b, strain 2362 (ABTS-1743) (e.g., VECTOLEX® from Valent BioSciences, US), +TX, Bacillus thuringiensis israelensis BMP144 strain (e.g., AQUABAC® by Becker Microbial Products IL), +TX, Bacillus thuringiensis subsp. aizawai C-91 strain, +TX, Bacillus thuringiensis Bacillus thuringiensis subsp. aizawai), especially serotype H-7 (e.g., FLORBAC® WG from Valent BioSciences, US) + TX, Bacillus thuringiensis subsp. aizawai, especially strain ABTS-1857 (SD-1372, e.g., XENTARI® from Valent BioSciences) + TX, Bacillus thuringiensis subsp. israelensis (serotype H-14) AM65-52 strain (accession number ATCC1276) (e.g., VECTOBAC® by Valent BioSciences, US) + TX, Bacillus thuringiensis subsp. krustaki subsp. Kurstaki) ABTS351 strain + TX, Bacillus thuringiensis subsp. KurstakiBacillus thuringiensis subsp. Kurstaki (BMP123 strain from Becker Microbial Products, IL, BARITONE from Bayer CropScience) + TX, Bacillus thuringiensis subsp. Kurstaki (EG2348 strain from Certis, US, LEPINOX) + TX, Bacillus thuringiensis subsp. Kurstaki (EG7841 strain from Certis, US, CRYMAX) + TX, Bacillus thuringiensis subsp. Kurstaki (HD-1 strain from Valent BioSciences, US, DIPEL® ES) + TX, Bacillus thuringiensis Bacillus thuringiensis subsp. Kurstaki) PB54 strain + TX, Bacillus thuringiensis subsp. Kurstaki SA11 strain (JAVELIN from Certis, US) + TX, Bacillus thuringiensis subsp. Kurstaki A12 (THURICIDE from Certis, US) + TX, Bacillus thuringiensis subsp. tenebrionis NB176 strain (SD-5428, e.g., NOVODOR® FC from BioFa DE) + TX, Bacillus thuringiensis var. Colmeri (e.g., Changzhou Jianghai Chemical) Factory's TIANBAOBTC)+TX, Bacillus thuringiensis var. japonensis Buibui strain+TX, Bacillus thuringiensis var. crustaceankurstaki)EVB-113-19 strain (e.g., BIOPROTEC® from AEF Global) + TX, Brevibacillus laterosporus + TX, Burkholderia spp., especially Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis MBI305 strain) (Accession number NRRL B-50319, International Publication No. 2011 / 106491 and International Publication No. 2013 / 032693, e.g., MBI206 TGAI and ZELTO® from Marrone Bio Innovations), + TX, Chromobacterium subtsugae subtsugae), especially the PRAA4-1T strain (e.g., MBI-203, e.g., GRANDEVO® from Marrone Bio Innovations) + TX, Lecanicillium muscarium Ve6 (MYCOTAL from Koppert) + TX, Paenibacillus popilliae (formerly Bacillus popilliae, e.g., MILKY SPORE POWDER® or MILKY SPORE GRANULAR® from St. Gabriel Laboratories) + TX, Serratia entomophila (e.g., INVADE® by Wrightson Seeds) + TX, Serratia marcescens, especially the SRM strain (accession number MTCC8708) + TX, Trichoderma asperelum Asperellum (TRICHODERMAX from Novozymes) + TX, Wolbachia pipientis ZAP strain (e.g., ZAP MALES® from MosquitoMate) + TX, . Beauveria bassiana strain ATCC74040 (e.g., NATURALIS® from Intrachem Bio Italia) + TX, Beauveria bassiana strain ATP02 (accession number DSM24665), Apopka 97 (PREFERAL from SePRO) + TX, Beauveria bassiana strain GHA (accession number ATCC74250, e.g., BOTANIGUARD® ES and MYCONTROL-O® from Laverlam International Corporation) + TX, Metarhizium anisopliae 3213-1 (deposited under NRRL accession number 67074, disclosed in International Publication No. 2017 / 066094, Pioneer Hi-Bred) International) + TX, Metarhizium robertsii 15013-1 (deposited under NRRL accession number 67073) + TX, Metarhizium robertsii 23013-3 (deposited under NRRL accession number 67075) + TX, Paecilomyces lilacinus 251 strains (Certis, MELOCON from US) + TX, Cydia pomonella (codling moth) granuloma virus (GV) + TX, Helicoverpa armigera (American tobacco moth larva) nuclear polyhedra virus (NPV) + TX, Adoxophyes Orana (apple tortrix moth) granuloma virus (GV) + TX, Spodoptera exigua (beet armyworm) mNPV + TX, Spodoptera fulgiperda (white fall armyworm) + TX, Burkholderia spp., especially Burkholderia cepacia (formerly known as Pseudomonas cepacia) + TX, Gigaspora spp. + TX, Glomus spp. + TX, Laccaria spp. + TX, Lactobacillus buchneri + TX, Paraglomus spp. + TX, Pisolithus tinctorus + TX, Pseudomonas spp. + TX, Rhizobium spp., especially Rhizobium trifolii trifolii)+TX, Rhizopogon spp.+TX, Scleoderma 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, Allium sativum (NEMGUARD from Eco-Spray, BRALIC from ADAMA) + TX, Armor-Zen + TX, Artemisia absinthium + TX, BioKeeper WP + TX, Brassicaceae extract, especially rapeseed oil powder or mustard powder + TX, Cassia nigricans + TX, Celastrus angulatus + TX, Chenopodium anthelminticum + TX, Chenopodium quinoa saponin extract from quinoa seeds (e.g., Heads Up plant protectants, Heads from CA) Up(registered trademark) (quinoa saponins) + TX, Chitin + TX, Dryopteris filix-mas + TX, Equisetum arvense + TX, Fortune Aza + TX, Fungastop + TX, Melaleuca alternifolia extract (TIMOREX GOLD from STK) + TX, Natural Blad polypeptide extracted from lupin seeds (FRACTURE(registered trademark) from FMC) + TX, Natural Blad polypeptide extracted from lupin seeds (PROBLAD(registered trademark) from Certis EU) + TX, Pyrethrin + TX, Quassia amara + TX, Quercus + TX, Quillaja extract (QL AGRI 35 from BASF) + TX, REGALIA from Marrone Bio MAXX)+TX, Requiem (trademark) insecticide+TX, Reynoutria sachalinensis extract (REGALLIA+TX), Rianya / Ryanodine+TX, Symphytum officinale+TX, Tanacetum vulgarevulgare)+TX, thymol+TX, thymol mixed with geraniol (CEDROZ from Eden Research)+TX, thymol mixed with geraniol and eugenol (MEVALONE from Eden Research)+TX, Triact70+TX, TriCon+TX, Tropaeulum majus+TX, Urtica dioica+TX, gelatrin+TX, Viscum album+TX, Mercuric oxide + TX, Octylinone + TX, Thiophanate-methyl + TX, MGK264+TX, 2-(2-butoxyethoxy)ethylpiperonylate+TX, 2-isovaleryllindan-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, antu+TX, arsenite+TX, barium carbonate+TX Benoxacol + TX, Bisthiosemi + TX, Brodifacum + TX, Bromadiolon + TX, Bromethalin + TX, Calcium cyanide + TX, Chloralose + TX, Chlorophacinone + TX, Cholecalciferol + TX, Chloquintoset (including Chloquintoset-Mexyl) + TX, Copper naphthenate + TX, Copper oxychloride + TX, Comacrol + TX, Coumafuryl + TX, Coumatetralyl + TX, Crimidine + TX, Cyprosulfamide + TX, Diazinon + TX, Dichlormid + TX, Dicyclopentadiene + TX, Diphenacum + TX, Di Fethialone + 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, Imanin + TX, Iodomethane + TX, Isoxadi Fen (containing isoxadiphen-ethyl) + TX, Lindan + TX, Magnesium phosphide + TX, MB-599 + TX, Mefenypr (containing mefenypr-diethyl) + TX, Metocamifen + TX, Methiocarb + TX, Methyl bromide + TX, Nerolidol + TX, Norbolmid + TX, Petroleum + TX, Phosacetim + TX, Phosphine + TX, Phosphate + TX, Pincdon + TX, Piperonyl butoxide + TX, Piprotal + TX, Potassium arsenite + TX, Probenazole + TX, Propyl isomer + TX, Pyridine-4-amine + TX, Pyrynulone + TX,Reynoutria sachalinensis extract + TX, ribavirin + TX, S421 + TX, siriloside + TX, sesamex + TX, sesamolin + 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.

[0358] In addition, the compositions of the present invention may be administered together with one or more systemic acquired resistance inducers ("SAR" inducers). SAR inducers are known and described, for example, in U.S. Patent No. 6,919,298, and include, for example, salicylates and the commercially available SAR inducer acibenzolar-S-methyl.

[0359] The compounds of formula (I) as defined in this invention are typically used in the form of compositions and can be applied simultaneously with or consecutively to a crop or treated plant with further compounds. These further compounds may be, for example, fertilizers or sources of trace elements or other preparations that affect plant growth. These may also be selective or non-selective herbicides, as well as insecticides, fungicides, bactericidal agents, nematicides, molluskicides, or mixtures thereof, and may include, as necessary, further carriers, surfactants, or application enhancers commonly used in the art of formulations.

[0360] The compounds of formula (I) as defined in the present invention may 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 as defined above in free form or in agrochemically usable salt form, and at least one of the above-mentioned adjuvants.

[0361] 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, the composition may, in addition to the compound of formula (I) as defined in the present invention, comprise at least one or more pesticides, such as additional fungicidal active ingredients.

[0362] Further aspects of the present invention relate to methods for controlling or preventing ectoparasitism 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, by plant pathogenic or putrefactive microorganisms or organisms, particularly fungi, that are potentially harmful to humans, and that methods include the application of a compound of formula (I) as defined in the present invention, or any of the preferred individual compounds as defined above as active ingredients for plants, to any part of a plant, a part of a plant or its habitat, its reproductive material, or non-biological material.

[0363] 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.

[0364] A preferred method for controlling or preventing ectoparasitism of crop plants by plant pathogenic microorganisms, particularly fungi, is foliar application, which involves the application of a pesticide composition containing a compound of formula (I) as defined in the present invention or at least one of said compounds. The frequency and amount of application will depend on the risk of ectoparasitism by the corresponding pathogen or insect. However, the 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. The 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.

[0365] Formulations, for example, compositions 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 expander, such as a solvent, a solid carrier, and optionally a surfactant.

[0366] Another subject of the present invention is the use of the composition for methods of controlling the above-mentioned types of pathogens, such as application methods 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.

[0367] When the combination of the present invention is used for seed treatment, it is generally sufficient to use a ratio of 0.001 to 50 g of the compound of formula (I) per 1 kg of seeds, preferably 0.01 to 10 g per 1 kg of seeds.

[0368] 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).

[0369] The compositions of the present invention may be any of the conventional forms, for example, a two-component system, a dry seed treatment powder (DS), a seed treatment emulsion (ES), a seed treatment fluid concentrate (FS), a seed treatment solution (LS), a seed treatment water-dispersible powder (WS), a seed treatment capsule suspension (CF), a seed treatment gel (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspension emulsion (SE), a capsule suspension (CS), water-dispersible granules (WG), or emulsifying granules. It may be employed in any technically feasible formulation form, such as 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 in combination with agriculturally acceptable adjuvants.

[0370] Such compositions can be produced by conventional methods, for example, by mixing an active ingredient with a suitable formulation inert component (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 efficacy 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, as well as 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.

[0371] The seed coating formulation is applied to seeds in a manner known to the art, using the combination and diluent of the present invention in a preferred seed coating formulation form, for example, as an aqueous suspension or in 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, for example, as a slow-release capsule or microcapsule.

[0372] Generally, a formulation comprises 0.01 to 90% by weight of an activator, 0 to 20% of an agrochemically acceptable surfactant, and 10 to 99.99% of solid or liquid formulation inert components and auxiliary agents, wherein the activator consists of at least compounds of formula (I) as defined in this invention, together with components (B) and (C) and optionally other activators such as particularly microbial agents or preservatives. The concentrate 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 typically use diluted formulations.

[0373] While it is preferable to formulate commercially available products as concentrates, end users typically utilize dilute formulations. [Examples]

[0374] The following examples illustrate the present invention. Certain compounds of the present invention may 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.

[0375] Combination example

[0376] [Table 5]

[0377] A wettable powder can be obtained by thoroughly mixing the active ingredient with an auxiliary agent, thoroughly grinding the mixture in a suitable mill, and diluting it with water to obtain a suspension of the desired concentration.

[0378] [Table 6]

[0379] The active ingredient is thoroughly mixed with an auxiliary agent, and the mixture is thoroughly ground in a suitable mill to obtain a powder that can be used directly for seed treatment.

[0380] emulsifiable concentrate Active ingredient [compound of formula (I)] 10% Octylphenol polyethylene glycol ether (ethylene oxide 4-5 mol) 3% Calcium dodecylbenzenesulfonate 3% Castor oil polyglycol ether (ethylene oxide 35 mol) 4% Cyclohexanone 30% Xylene mixture 50%

[0381] Any emulsion of any required dilution that may be used for plant protection can be obtained from this concentrate by dilution with water.

[0382] [Table 7]

[0383] The active ingredient is mixed with a carrier, and this mixture is ground in a suitable mill to obtain a ready-to-use powder. Such a powder can also be used for drying and coating seeds.

[0384] Extruded granules Active ingredient [compound of formula (I)] 15% Sodium lignin sulfonate 2% Carboxymethylcellulose 1% Kaolin 82%

[0385] 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.

[0386] Coated granules Active ingredient [compound of formula (I)] 8% Polyethylene glycol (molecular weight 200) 3% Kaolin 89%

[0387] The finely ground active ingredient is uniformly applied in a mixer to kaolin moistened with polyethylene glycol. A non-dusting coated granule is thus obtained.

[0388] 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%

[0389] By tightly mixing the finely ground active ingredient with an auxiliary agent, a suspension concentrate can be obtained, which can then be diluted with water to obtain a suspension of any desired dilution. 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.

[0390] 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 (in the form of a 20% aqueous solution) 0.5% Monoazo pigment calcium salt 5% Silicone oil (in the form of a 75% emulsion in water) 0.2% Water 45.3%

[0391] By tightly mixing the finely ground active ingredient with an auxiliary agent, a suspension concentrate can be obtained, which can then be diluted with water to obtain a suspension of any desired dilution. 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.

[0392] 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. Stabilize the resulting capsule suspension by adding 0.25 parts thickener and 3 parts dispersant. The capsule suspension formulation contains 28% active ingredient. The diameter of the medium capsules is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension using equipment suitable for its purpose.

[0393] 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.

[0394] Method A: Equipment: Shimadzu LCMS2020 mass spectrometer; Column: HALO C 18 2.7 μm, 3.0 mm × 30 mm; Mobile phase: MeCN (containing 0.05% HCOOH or 0.05% TFA) - Water (containing 0.05% HCOOH or 0.05% TFA); Gradient: MeCN from 5% to 95% over 1.4 min, hold for 0.6 min, total run time 2.5 min; Flow rate: 1.8 mL / min; Column temperature: 50°C; Wavelength: 214 nm and 254 nm PDA.

[0395] Methods B1 and B2: Agilent 1100 series LC / MSD system equipped with DAD / ELSD Alltech 2000ES and Agilent LC / MSD VL (G1956B) and SL (G1956B) mass spectrometers. Agilent 1200 series LC / MSD system equipped with DAD / ELSD Alltech 3300 and Agilent LC / MSD G6130A and G6120B mass spectrometers. Agilent Technologies 1260 Infinity LC / MSD system with DAD / ELSD Alltech 3300 and Agilent. LC\MSDG6120B mass spectrometer. Agilent Technologies 1260 Infinity II LC / MSD stem equipped with DAD / ELSD G7102A 1290 Infinity II and Agilent LC / MSD G6120B mass spectrometer. Agilent 1260 series LC / MSD system equipped with DAD\ELSD and Agilent LC\MSD (G6120B) mass spectrometer. UHPLC Agilent 1290 series LC / MSD system equipped with DAD\ELSD and Agilent LC\MSD (G6125B) mass spectrometer.

[0396] Method B1: Column: Agilent Poroshell 120 SB-C18 4.6×30mm 2.7μm Column temperature: 60℃ Mobile phase: A-Water (0.1% formic acid), B-Acetonitrile (0.1% formic acid), Flow rate: 3ml / min Gradient: 0.01 min - 1% B, 1.5 min - 100% B, 1.73 min - 100% B MS ionization mode: Electrospray ionization (ESI) MS scan range: 83-600 m / z UV detection: 215nm, 254nm, 280nm.

[0397] Method B2: Column: Agilent Poroshell 120 SB-C18 4.6×30mm 2.7 Temperature: 60℃ Mobile phase: A-Water (0.1% formic acid), B-Acetonitrile (0.1% formic acid), Flow rate: 3ml / min Gradient: 0.01 min -1% B, 1.5 min -100% B, 2.2 min -100% B. MS ionization mode: Electrospray ionization (ESI) MS scan range: 83~1000 m / z UV detection: 215nm, 254nm, 280nm.

[0398] Method C: Spectra were recorded 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: 0.8–3.00kV, cone: 5–30V, source temperature: 120–150°C, desolvation temperature: 350–600°C, cone gas flow rate: 50–150 l / h, desolvation gas flow rate: 650–1000 l / h, mass range: 110–950 Da, and a Waters Corporation Acquity UPLC: binary pump, heated column compartment, diode array detector, and ELSD. Column: Waters UPLC HSS 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: 10% B fixed composition for 0.2 min, then 10~100% B for 1.0 min, 100~10% B for 0.2 min, 100~10% B for 0.05 min, 10% B fixed composition for 0.05 min

[0399] Method D: Spectra were recorded using a Waters Corporation ACQUITY mass spectrometer (SQD or SQDII single quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive and negative ions), capillary: 3.0kV, cone: 30V, extractor: 3.00V, source temperature: 150°C, desolvation temperature: 400°C, cone gas flow rate: 60 L / h, desolvation gas flow rate: 700 L / h, mass range: 140~800 Da), as well as a Waters Corporation ACQUITY UPLC equipped with a solvent degasser, binary pump, heated column compartment, and diode array detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm, Temperature: 60°C, DAD wavelength range (nm): 210~400, Solvent gradient: A = Water / Methanol 9:1 + 0.1% Formic Acid, B = Acetonitrile + 0.1% Formic Acid, Gradient: 0~100% B over 2.5 minutes; Flow rate (ml / min) 0.75.

[0400] Table A below summarizes the compounds of formula (I): - LC / MS data (retention time (RT), [M+H] + etc.), - Type of method, and / or - Melting point (mp).

[0401] [Table 8-1]

[0402] [Table 8-2]

[0403] [Table 8-3]

[0404] [Table 8-4]

[0405] [Table 8-5]

[0406] [Table 8-6]

[0407] [Table 8-7]

[0408] [Table 8-8]

[0409] [Table 8-9]

[0410] Example 1: This example illustrates the preparation of methyl N-[5-[6-[2,3-dihydrobenzofuran-7-yl(methyl)carbamoyl]-8-methylimidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (Compound 1). Step 1: Preparation of methyl 8-methylimidazo[1,2-a]pyridine-6-carboxylate [ka] A mixture of methyl 8-bromoimidazo[1,2-a]pyridine-6-carboxylate (CAS 1234616-08-0; 1.00 g, 3.80 mmol, 1.00 equivalent), methylboronic acid (0.460 g, 7.50 mmol, 2.00 equivalent), and potassium carbonate (1.00 g, 7.50 mmol, 2.00 equivalent) in 2-methyltetrahydrofuran (28 mL) was flushed with argon for 5 minutes. Then, Xphos Pd G4 (CAS 1599466-81-5; 0.17 g, 0.19 mmol, 0.05 equivalent) was added, and the reaction mixture was heated at 80°C and stirred for a further 16 hours. The reaction mixture was cooled to room temperature, and then water was added. 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 using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain methyl 8-methylimidazo[1,2-a]pyridine-6-carboxylate as a brown solid. LC / MS (Method C) retention time = 0.14 min; [M+H] + =190 1 H NMR(400MHz,CDCl3)δ ppm 8.81(s,1H),7.70(d,J=1.2Hz,1H),7.66(d,J=1.2Hz,1H),7.54(s,1H),3.95(s,3H),2.65(s,3H).

[0411] Step 2: Preparation of methyl 3-bromo-8-methylimidazo[1,2-a]pyridine-6-carboxylate [ka] To a stirred solution of methyl 8-imidazo[1,2-a]pyridine-6-carboxylate (3.00 g, 16.0 mmol, 1.00 equivalent) in acetonitrile (79 mL), N-bromosuccinimide (3.20 g, 17.0 mmol, 1.10 equivalent) was added at room temperature, and the mixture was stirred for a further 2 hours. The reaction mixture was quenched with a saturated aqueous solution of sodium bisulfite, and the precipitate was collected by filtration. The filtered cake was washed with water and dried overnight at 40°C under vacuum. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain methyl 3-bromo-8-methylimidazo[1,2-a]pyridine-6-carboxylate as a pale yellow solid. LC / MS (Method C) Retention time=0.79;[M+H] + =269 / 271 1 H NMR(400MHz,CDCl3)δ ppm 8.78(br s,1H),7.68(s,1H),7.60-7.64(m,1H),3.99(s,3H),2.60(s,3H).

[0412] Step 3: Preparation of 3-bromo-8-methylimidazo[1,2-a]pyridine-6-carboxylic acid (compound X1) [ka] (Compound X1) Lithium hydroxide (1.25 g, 52.0 mmol, 2.00 equivalents) was added to a solution of methyl 3-bromo-8-methylimidazo[1,2-a]pyridine-6-carboxylate (7.00 g, 26.0 mmol, 1.00 eq.) in tetrahydrofuran / water (1 / 1, 120 mL). The resulting mixture was stirred at room temperature for 1 hour. The reaction product was diluted with water and extracted with diethyl ether. The aqueous layer was then acidified to pH=2 with 2 M aqueous HCl, the precipitate was collected by filtration, washed with water, and concentrated under reduced pressure to obtain 3-bromo-8-methylimidazo[1,2-a]pyridine-6-carboxylic acid as a brown solid. LC / MS (Method C) retention time=0.44;[M+H] + =255 / 257 1 H NMR(400MHz,DMSO-d6)δ ppm 13.46(br s,1H),8.64(br s,1H),7.82(s,1H),7.58(s,1H),2.54(s,3H).

[0413] Step 4: Preparation of 3-bromo-N-(2,3-dihydrobenzofuran-7-yl)-8-methylimidazo[1,2-a]pyridine-6-carboxamide [ka] To an ice-cold solution of 2,3-dihydrobenzofuran-7-amine (0.400 g, 2.96 mmol, 1.00 equivalent) and 3-bromo-8-methylimidazo[1,2-a]pyridine-6-carboxylic acid (compound X1) (0.830 g, 3.26 mmol, 1.10 equivalent) in pyridine (10.0 mL), phosphoryl trichloride (1.36 g, 8.88 mmol, 3.00 equivalent) was added dropwise. The solution was stirred at room temperature for 2 hours. The aqueous solution was adjusted to pH approximately 7 with a saturated solution of sodium bicarbonate. The reaction mixture was cooled to room temperature, and then water was added. 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 using a silica gel cartridge (petroleum ether / ethyl acetate) to obtain 3-bromo-N-(2,3-dihydrobenzofuran-7-yl)-8-methylimidazo[1,2-a]pyridine-6-carboxamide as a yellow solid. LC / MS (Method B) Retention time=1.16;[M+H] + =372 / 374 1 H NMR(400MHz,DMSO-d6)δ ppm 10.16(s,1H),8.85(s,1H),7.81(s,1H),7.67(s,1H),7.31(d,J=7.8Hz,1H),7.12(d,J=7. 2Hz,1H),6.85(t,J=7.6Hz,1H),4.58(t,J=8.6Hz,2H),3.25(t,J=8.6Hz,2H),2.56(s,3H).

[0414] Step 5: Preparation of 3-bromo-N-(2,3-dihydrobenzofuran-7-yl)-N,8-dimethylimidazo[1,2-a]pyridine-6-carboxamide [ka] 3-bromo-8-methyl-N-(2,3,4,5-tetrahydrobenzofuran-7-yl)imidazo[1,2-a]pyridine-6-carboxamide (0.260 g, 0.695 mmol, 1.00 equivalent) was dissolved in dimethylformamide (3.0 mL) and purged with an argon stream. Sodium hydride (60% by mass in oil; 0.025 g, 1.0 mmol, 1.50 equivalent) was added in small amounts to this ice-cold solution, and the resulting mixture was stirred at 0°C for 20 minutes. Then, iodomethane (0.197 g, 1.39 mmol, 2.00 equivalent) was added dropwise, and the mixture was stirred, warmed to room temperature, and stirred for a further 2 hours. The mixture was then diluted with ethyl acetate and treated with ice-cold water. The aqueous phase 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 using a silica gel cartridge (dichloromethane / methanol) to obtain 3-bromo-N-(2,3-dihydrobenzofuran-7-yl)-N,8-dimethylimidazo[1,2-a]pyridine-6-carboxamide as a yellow solid. LC / MS (Method B) Retention time=1.15;[M+H] + = 386 / 388 1 H NMR(400MHz,DMSO-d6)δ ppm 7.93(s,1H),7.67(s,1H),7.31-7.05(m,2H),6.98(d,J=7.6Hz,1H),6.72(t,J=7.6Hz,1H),4.56(br s,2H),3.27(s,3H),3.17(br m,2H),2.41(s,3H).

[0415] Step 6: Preparation of methyl N-[5-[6-[2,3-dihydrobenzofuran-7-yl(methyl)carbamoyl]-8-methylimidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate [ka] A mixture of 3-bromo-N-(2,3-dihydrobenzofuran-7-yl)-N,8-dimethylimidazo[1,2-a]pyridine-6-carboxamide (0.210 g, 0.544 mmol, 1.00 equivalent) and methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (0.227 g, 0.816 mmol, 1.50 equivalent) was mixed with dioxane / water (4 / 1; 3.0 mL) and potassium carbonate (0.188 g, 1.36 mmol, 2.50 equivalent), and the mixture was purged with an argon stream for 5 minutes. Next, [1,1'-bis-(diphenylphosphino)-ferrocene]-dichloropalladium(II) (0.040 g, 0.054 mmol, 0.10 equivalents) was added, and the mixture was heated at 100°C for 30 minutes under microwave irradiation. The mixture was cooled and diluted with dichloromethane and water. The aqueous phase was extracted with dichloromethane, 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 in a silica gel cartridge (dichloromethane / methanol) to obtain methyl N-[5-[6-[(2,3-dihydrobenzofuran-7-yl(methyl)carbamoyl)]-8-methylimidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate as an off-white solid. LC / MS (Method B) Retention time=0.924;[M+H] + =458 1 H NMR(400MHz,DMSO-d6)δ ppm 10.48(s,1H),8.23-8.15(m,1H),7.98(d,J=8.6Hz,1H),7.90(s,1H),7.70(s,1H),7.60(d,J=7.4 Hz,1H),7.20(s,1H),7.07(d,J=6.8Hz,1H),6.89(d,J=7.6Hz,1H),6.69(t,J=7.6Hz,1H),4.55(br s,1H),4.29(br s,1H),3.74(s,3H),3.24(s,3H),3.11(br s,2H),2.47(s,3H).

[0416] Example 2: This example illustrates the preparation of methyl N-[5-[6-[6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-carbonyl)-8-methylimidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 2). Step 1: Preparation of 2-(5-fluoro-N-methyl-2-nitro-anilino)acetic acid [ka] To a solution of 2,4-difluoro-1-nitrobenzene (CAS 446-35-5) (5.00 g, 31.4 mmol, 1.00 equivalent) in an ethanol / water mixture (7:3, 130 mL), 2-(methylamino)acetic acid (2.80 g, 31.4 mmol, 1.00 equivalent) and sodium bicarbonate (6.60 g, 78.6 mmol, 2.50 equivalent) were added. The mixture was then heated to 80°C and stirred for a further 2 hours. The organic solvent was then removed under reduced pressure, and the aqueous solution was adjusted to pH approximately 4 with 2N HCl. The resulting mixture was diluted with water, extracted with dichloromethane, washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to obtain 2-(5-fluoro-N-methyl2-nitro-anilino)acetic acid. LC / MS (Method B) Retention time=1.00;[M+H] + =229

[0417] Step 2: Preparation of 6-fluoro-4-methyl-1,3-dihydroquinoxaline-2-one [ka] To a solution of 2-(5-fluoro-N-methyl-2-nitro-anilino)acetic acid (4.00 g, 17.5 mmol, 1.00 equivalent) and potassium carbonate (18.9 g, 137 mmol, 7.80 equivalents) in water (45 mL), sodium hyposulfite (19.2 g, 110 mmol, 6.30 equivalents) in water (55 mL) was added dropwise. The reaction mixture was stirred at room temperature for a further 1 hour, and then the aqueous solution was adjusted to pH approximately 4 with 6N HCl. The resulting mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (petroleum ether / ethyl acetate) to obtain 6-fluoro-4-methyl-1,3-dihydroquinoxarin-2-one as a yellow solid. LC / MS (Method B) Retention time=0.94;[M+H] + =181

[0418] Step 3: Preparation of 6-fluoro-4-methyl-2,3-dihydro-1H-quinoxaline [ka] A solution of 6-fluoro-4-methyl-1,3-dihydroquinoxaline-2-one (1.20 g, 6.66 mmol, 1.00 equivalent) in tetrahydrofuran (20.0 mL) was added dropwise to an ice-cold solution of lithium aluminum hydride (1.01 g, 26.6 mmol, 4.00 equivalent) in tetrahydrofuran (30.0 mL). The reaction mixture was then warmed to room temperature and stirred for a further 6 hours. The resulting mixture was quenched with water, a 15% sodium hydroxide aqueous solution, and water. The mixture was filtered, and the filtrate was concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (petroleum ether / ethyl acetate) to obtain 6-fluoro-4-methyl-2,3-dihydro-1H-quinoxaline as a yellow oily substance. This compound is also commercially available (CAS 1354953-50-6). LC / MS (Method B) Retention time=0.68;[M+H] + =167

[0419] Step 4: Preparation of (3-bromo-8-methylimidazo[1,2-a]pyridine-6-yl)-(6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-yl)methanone [ka] To an ice-cold solution of 6-fluoro-4-methyl-2,3-dihydro-1H-quinoxaline (0.200 g, 1.20 mmol, 1.00 equivalent) and 3-bromo-8-methylimidazo[1,2-a]pyridine-6-carboxylic acid (compound X1) (0.338 g, 1.32 mmol, 1.10 equivalents) in pyridine (5.0 mL), phosphoryl trichloride (0.554 g, 3.61 mmol, 3.00 equivalents) was added dropwise, and the reaction mixture was stirred at room temperature for a further 3 hours. The mixture was then adjusted to a pH of approximately 7 with saturated sodium bicarbonate solution, further 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 crude residue was purified using a silica gel cartridge (petroleum ether / ethyl acetate) to obtain (3-bromo-8-methylimidazo[1,2-a]pyridine-6-yl)-(6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-yl)methanone as a yellow solid. LC / MS (Method B) Retention time=1.26;[M+H] + =403 / 405 1 H NMR(400MHz,DMSO-d6)δ ppm 8.24(s,1H),7.76(s,1H),7.09(s,1H),6.92(s,1H),6.57(dd,J=12.0,2.8Hz,1H),6.19( t,J=8.2Hz,1H),3.88(t,J=5.2Hz,2H),3.44(t,J=5.0Hz,2H),2.96(s,3H),2.45(s,3H).

[0420] Step 5: Preparation of methyl N-[5-[6-[6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-carbonyl)-8-methylimidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate [ka] Potassium carbonate (0.120 g, 0.868 mmol, 2.50 equivalents) was added to a solution of (3-bromo-8-methylimidazo[1,2-a]pyridine-6-yl)-(6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-yl)methanone (0.140 g, 0.347 mmol, 1.00 equivalent) and methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (0.145 g, 0.521 mmol, 1.50 equivalent) in 1,4-dioxane / water (4:1, 2.5 mL). The mixture was purged with an argon stream for 2 minutes, and then [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.0254 g, 0.0347 mmol, 0.100 equivalents) was added to the reaction mixture under an N2 atmosphere. The resulting reaction mixture was heated at 65°C for 1 hour. After cooling to room temperature, the reaction mixture was filtered through a Celite pad and further extracted with ethyl acetate. The filtrate was washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by trituration with acetonitrile to obtain methyl N-[5-[6-[6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-carbonyl)-8-methylimidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate as a yellow solid. LC / MS (Method B) Retention time=1.10;[M+H] + =475 1 H NMR(400MHz,DMSO-d6)δ ppm 10.45(s,1H),8.43(d,J=1.6Hz,1H),8.28(s,1H),7.96(d,J=8.6Hz,1H),7.81(s,1H),7.73(s,1H),7.11(s,1H),6.88(s,1H),6.57 (dd,J=12.0,2.6Hz,1H),6.21(t,J=7.2Hz,1H),3.88(t,J=4.9Hz,2H),3.72(s,3H),3.43(t,J=4.9Hz,2H),2.94(s,3H),2.49(s,3H)

[0421] Example 3: This example illustrates the preparation of methyl N-[5-[6-[6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 3). Step 1: Preparation of (3-bromoimidazo[1,2-a]pyridine-6-yl)-(6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-yl)methanone [ka] To an ice-cold solution of 6-fluoro-4-methyl-2,3-dihydro-1H-quinoxaline (0.400 g, 2.41 mmol, 1.00 equivalent) and 3-bromoimidazo[1,2-a]pyridine-6-carboxylic acid (CAS 886362-00-1) (0.638 g, 2.65 mmol, 1.10 equivalent) in pyridine (10.0 mL), phosphoryl trichloride (1.11 g, 7.22 mmol, 3.00 equivalent) was added dropwise. The reaction mixture was stirred at room temperature for 3 hours. The mixture was then adjusted to a pH of approximately 7 with saturated sodium bicarbonate solution, further 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 crude residue was purified using a silica gel cartridge (petroleum ether / ethyl acetate) to obtain (3-bromoimidazo[1,2-a]pyridine-6-yl)-(6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-yl)methanone as a yellow solid. LC / MS (Method B) Retention time=1.22;[M+H] + =389 / 391 1 H NMR(400MHz,DMSO-d6)δ ppm 8.44(s,1H),7.80(s,1H),7.57(d,J=9.2Hz,1H),7.14(d,J=8.0Hz,1H),6.84(s,1H),6.57(dd ,J=12.0,2.6Hz,1H),6.16(s,1H),3.90(t,J=5.0Hz,2H),3.47(t,J=5.0Hz,2H),2.96(s,3H).

[0422] Step 2: Preparation of methyl N-[5-[6-[6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 3) [ka] (Compound 3) Potassium carbonate (0.249 g, 1.80 mmol, 2.50 equivalents) was added to a solution of (3-bromoimidazo[1,2-a]pyridine-6-yl)-(6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-yl)methanone (0.280 g, 0.719 mmol, 1.00 equivalent) and methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (0.300 g, 1.08 mmol, 1.50 equivalents) in 1,4-dioxane / water (4:1, 3.00 mL). The mixture was purged with an argon stream for 2 minutes, and [1,1'-bis-(diphenylphosphino)-ferrocene]-dichloropalladium(II) (0.053 g, 0.072 mmol, 0.10 equivalents) was added. The resulting reaction mixture was heated at 65°C for 1 hour. After cooling to room temperature, the reaction mixture was filtered through a Celite pad and further extracted with ethyl acetate. The filtrate was washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by trituration with acetonitrile to obtain methyl N-[5-[6-[6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate as a yellow solid. LC / MS (Method B) Retention time=1.03;[M+H] + =461 1H NMR(400MHz,DMSO-d6)δ ppm 10.46(s,1H),8.55-8.41(m,2H),7.98(d,J=8.6Hz,1H),7.86(s,1H),7.85(d,J=5.0Hz,1H),7.60(d,J=9.2Hz,1H),7.17(d,J=8.8Hz,1H), 6.84(s,1H),6.57(dd,J=12.0,2.6Hz,1H),6.19(t,J=7.4Hz,1H),3.89(t,J=5.0Hz,2H),3.72(s,3H),3.46(t,J=4.8Hz,2H),2.95(s,3H).

[0423] Example 4: This example illustrates the preparation of methyl N-[5-[6-[7-fluoro-2,3-dihydro-1,4-benzoxazine-4-carbonyl)-8-methylimidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 5). Step 1: Preparation of methyl 3-iodo-8-methylimidazo[1,2-a]pyridine-6-carboxylate [ka] To a solution of methyl 8-imidazo[1,2-a]pyridine-6-carboxylate (3.00 g, 16.0 mmol, 1.00 equivalent) in acetonitrile (79 mL, 5.00 mL / mmol), N-iodosuccinimide (3.20 g, 17.0 mmol, 1.10 equivalent) was added at room temperature, and the mixture was stirred for 2 hours. The reaction mixture was then quenched with a saturated aqueous solution of sodium thiosulfate, and the precipitate was collected by filtration. The filtered cake was washed with water and dried overnight at 40°C under vacuum. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain methyl 3-iodo-8-methylimidazo[1,2-a]pyridine-6-carboxylate as a pale yellow solid. LC / MS (Method B) Retention time=1.13;[M+H] + =317 1H NMR(400MHz,DMSO-d6)δ ppm 8.62(dd,J=1.6,0.6Hz,1H),7.81(s,1H),7.51-7.54(m,1H),3.91(s,3H),2.53(s,3H).

[0424] Step 2: Preparation of 3-iodo-8-methylimidazo[1,2-a]pyridine-6-carboxylic acid (compound X2) [ka] (Compound X2) Lithium hydroxide (1.25 g, 52.0 mmol, 2.00 equivalents) was added to a solution of methyl 3-iodo-8-methylimidazo[1,2-a]pyridine-6-carboxylate (7.00 g, 26.0 mmol, 1.00 eq.) in a tetrahydrofuran / water mixture (1 / 1, 120.0 mL). The resulting mixture was stirred at room temperature for 1 hour. The reaction product was diluted with water and extracted with diethyl ether. The aqueous layer was then acidified to pH 2 with a 2 M aqueous HCl solution, the precipitate was collected by filtration, washed with water, and concentrated under reduced pressure to obtain 3-iodo-8-methylimidazo[1,2-a]pyridine-6-carboxylic acid as a brown solid. LC / MS (Method B) Retention time=0.75;[M+H] + =303 1 H NMR(400MHz,DMSO-d6)δ ppm 8.52(s,1H),7.64(s,1H),7.58-7.62(m,1H),2.47(s,3H).

[0425] Step 3: Preparation of (7-fluoro-2,3-dihydro-1,4-benzoxazine-4-yl)-(3-iodo-8-methylimidazo[1,2-a]pyridine-6-yl)methanone [ka] A mixture of 3-iodo-8-methylimidazo[1,2-a]pyridine-6-carboxylic acid (compound X2) (0.500 g, 1.66 mmol, 1.00 equivalent) in dimethylformamide (8.00 mL) was mixed with 1-methylimidazole (0.340 g, 4.14 mmol, 2.50 equivalents) and [chloro(dimethylamino)methylene]-dimethyl-ammonium hexafluorophosphate (0.697 g, 2.48 mmol, 1.50 equivalents). This solution was stirred at room temperature for 15 minutes, then 7-fluoro3,4-dihydro-2H-1,4-benzoxazine (0.279 g, 1.82 mmol, 1.10 equivalents) was added, and the resulting mixture was stirred at room temperature for a further 3 hours. The reaction mixture was then cooled to room temperature, and water was added. 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 using a silica gel cartridge (petroleum ether / ethyl acetate) to obtain (7-fluoro-2,3-dihydro-1,4-benzoxazine-4-yl)-(3-iodo-8-methylimidazo[1,2-a]pyridine-6-yl)methanone as a brown solid. LC / MS (Method B) Retention time=1.10;[M+H]-=438

[0426] Step 4: Preparation of methyl N-[5-[6-[7-fluoro-2,3-dihydro-1,4-benzoxazine-4-carbonyl)-8-methylimidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 5) [ka] (Compound 5) Potassium carbonate (158 mg, 1.14 mmol, 2.50 equivalents) was added to a solution of (7-fluoro-2,3-dihydro-1,4-benzoxazine-4-yl)-(3-iodo-8-methylimidazo[1,2-a]pyridine-6-yl)methanone (200 mg, 0.457 mmol, 1.00 equivalent) and methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (191 mg, 0.686 mmol, 1.50 equivalents) in 1,4-dioxane / water (4:1, 5.00 mL). The mixture was purged with an argon stream for 2 minutes, and [1,1'-bis-(diphenylphosphino)-ferrocene]-dichloropalladium(II) (33.5 mg, 0.0457 mmol, 0.10 equivalents) was added. The resulting reaction mixture was heated at 65°C for 1 hour. 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 and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by trituration with acetonitrile to obtain methyl N-[5-[6-[7-fluoro-2,3-dihydro-1,4-benzoxazine-4-carbonyl)-8-methylimidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate as an off-white solid. LC / MS (Method B) Retention time=1.03;[M+H] + =462 1 H NMR(400MHz,DMSO-d6)δ ppm 10.44(s,1H),8.60-8.44(m,2H),8.04-7.87(m,2H),7.84(s,1H),7.47(s,1H),7.25(s,1H),6.83(dd,J=10. 0,3.0Hz,1H),6.68(td,J=8.7,2.9Hz,1H),4.39-4.25(m,2H),4.03-3.85(m,2H),3.71(s,3H),2.54(s,3H).

[0427] Example 5: This example illustrates the preparation of methyl N-[5-[6-[(2-chloro-4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound 20). Step 1: Preparation of 3-[6-(methoxycarbonialamino)-3-pyridyl]imidazo[1,2-a]pyridine-6-carboxylic acid (compound X3) [ka] (Compound X3) Sodium carbonate (0.132 g, 1.24 mmol, 3.00 equivalent) was added to a solution of 3-bromoimidazo[1,2-a]pyridine-6-carboxylic acid (CAS 886362-00-1) (0.100 g, 0.415 mmol, 1.00 equivalent) and methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (0.173 g, 0.622 mmol, 1.50 equivalent) in 1,4-dioxane / water (4 / 1, 2.00 mL). The mixture was purged with an argon stream for 2 minutes, then tetrakistriphenylphosphine palladium (0) (0.024 g, 0.021 mmol, 0.050 equivalent) was added, and the resulting reaction mixture was heated at 90°C for 4 hours. Next, the reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was diluted with water, the aqueous layer was acidified to pH 2 with a 2 M aqueous HCl solution, and the resulting precipitate was collected by filtration, washed with water, and dried under reduced pressure to obtain 3-[6-(methoxycarbonylamino)-3-pyridyl]imidazo[1,2-a]pyridine-6-carboxylic acid as an off-white solid. LC / MS (Method B) Retention time=0.82;[M+H] + =313 1 H NMR(400MHz,CD3OD)δ ppm 9.13-9.17(m,1H)8.68-8.73(m,1H)8.50-8.57(m,1H)8.33-8.44(m,3H)8.11-8.17(m,1H)7.98-8.05(m,1H)3.85(s,3H).

[0428] Step 2: Preparation of methyl N-[5-[6-[(2-chlorolo-4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 20) [ka] (Compound 20) To a solution of 2-chloro-4-fluoro-N-methylaniline (18 mg, 0.113 mmol, 2.00 equivalents) and 3-[6-(methoxycarbonylamino)-3-pyridyl]imidazo[1,2-a]pyridine-6-carboxylic acid (compound X3) (24 mg, 0.077 mmol, 1.00 equivalent) in dry acetonitrile (0.5 ml), 2-chloro-N-methylpyridinium iodide (27 mg, 0.11 mmol, 1.40 equivalents) and diisopropylethylamine (31 mg, 0.24 mmol, 3.1 equivalents) were added. The reaction mixture was stirred at room temperature for 30 minutes, then heated to 80°C and stirred for a further 12 hours. The mixture was then cooled to room temperature and the solvent was evaporated under reduced pressure. The resulting residue was dissolved in dimethyl sulfoxide, and this solution was filtered. The crude product was purified by HPLC (water (0.1% formic acid) / acetonitrile (0.1% formic acid)) to obtain methyl N-[5-[6-[(2-chloro-4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate. LC / MS (Method B) Retention time = 0.84 min; [M+H] + =454

[0429] Example 6: This example illustrates the preparation of methyl N-[5-[6-[(6-fluoro-5-methoxy-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 62). Step 1: Preparation of 8-bromo-6-fluoroquinoline-5-ol [ka] Glycerol (0.390 mL, 0.492 g, 1.20 equivalents) was added at room temperature to a solution of 2-bromo-4-fluoro-5-methoxyaniline (1.00 g, 4.41 mmol, 1.00 equivalent) and sodium iodide (0.007 g, 0.04 mmol, 0.01 equivalent) in sulfuric acid (4.4 mL). The reaction mixture was heated to 150 °C and stirred for a further 5 hours. The mixture was then cooled to 0-5 °C and slowly basicized with a saturated solution of sodium bicarbonate to pH 5. 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 using a silica gel cartridge (cyclohexane / ethyl acetate; ethanol (3 / 1)) to obtain 8-bromo-6-fluoro-quinoline-5-ol as a pale pink solid. LC / MS (Method C) Retention time=0.72;[M+H] + = 242 / 244 1 H NMR(400MHz,CD3OD)δ ppm 8.85-8.92(m,1H)8.68-8.75(m,1H)7.91-8.00(m,1H)7.55-7.58(m,1H)

[0430] Step 2: Preparation of 8-bromo-6-fluoro-5-methoxyquinoline [ka] To a solution of 8-bromo-6-fluoroquinoline-5-ol (0.420 g, 0.868 mmol, 1.00 equivalent) and potassium carbonate (0.600 g, 4.34 mmol, 5.00 equivalent) in acetone (8.68 mL, 10 mL), methyl iodide (0.271 mL, 0.619 g, 4.34 mmol, 5.00 equivalent) was added dropwise. The reaction mixture was stirred at room temperature for 2 hours, then quenched with water. 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 using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain 8-bromo-6-fluoro-5-methoxyquinoline as a white solid. LC / MS (Method C) retention time=0.92;[M+H]+ = 256 / 258 1 H NMR(400MHz,CDCl3)δ ppm 8.91-9.03(m,1H)8.43-8.58(m,1H)7.81-7.95(m,1H)7.41-7.54(m,1H)4.15(s,3H).

[0431] Step 3: Preparation of 6-fluoro-5-methoxy-1,2,3,4-tetrahydroquinoline [ka] A solution of 8-bromo-6-fluoro-5-methoxyquinoline (0.140 g, 0.547 mmol, 1.00 equivalent) in ethanol (13.7 mL) was passed through an H-Cube® under the following conditions: Pd / C cartridge, complete H2, 40 bar, 50°C, flow rate 1 mL / min. The reaction mixture was concentrated under reduced pressure to obtain 6-fluoro-5-methoxy-1,2,3,4-tetrahydroquinoline as a white solid. LC / MS (Method C) Retention time=0.55;[M+H] + =182 1 H NMR(400MHz,CDCl3)δ ppm 10.67-11.28(br s,1H)7.40(dd,J=9.1,4.0Hz,1H),7.05(dd,J=11.1,8.9Hz,1H),3.99(s,3H),3.45-3.59(m,2H),2.83(t,J=6.5Hz,2H),2.22-2.32(m,2H).

[0432] Step 4: Preparation of methyl N-[5-[6-[6-fluoro-5-methoxy-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 62) [ka] (Compound 62) To a suspension of 3-[6-(methoxycarbonylamino)-3-pyridyl]imidazo[1,2-a]pyridine-6-carboxylic acid (compound X3) (0.135 g, 0.432 mmol, 1.00 equivalent), 6-fluoro-5-methoxy-1,2,3,4-tetrahydroquinoline (0.0783 g, 0.432 mmol, 1.00 equivalent), and triethylamine (0.241 mL, 1.73 mmol, 4.00 equivalent) in acetonitrile (4.32 mL, 10 mL / mmol), propylphosphonic anhydride (50% in ethyl acetate; 0.515 mL, 0.865 mmol, 2.00 equivalent) was added. The reaction mixture was stirred at room temperature for 18 hours, then 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 using a silica gel cartridge (cyclohexane / ethyl acetate:ethanol (3 / 1)) to obtain methyl N-[5-[6-(6-fluoro-5-methoxy3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate as a yellow solid. LC / MS (Method C) retention time = 0.73 min; [M+H] + =476 1 H NMR(400MHz,CDCl3)δ ppm 8.40-8.46(m,1H),8.34-8.40(m,1H),8.21-8.29(m,1H),8.14(d,J=8.7Hz,1H),7.72-7.73(m,1H),7.70(dd,J= 8.7,2.5Hz,1H),7.51(dd,J=9.5,0.7Hz,1H),7.02(dd,J=9.5,1.5Hz,1H),6.70(dd,J=11.3,8.7Hz,1H),6.46(br dd,J=8.5,3.8Hz,1H),4.01(d,J=2.5Hz,3H),3.86-3.89(t,J=6.4Hz,2H),3.85(s,3H),2.84(t,J=6.7Hz,2H),1.99-2.08(m,2H).

[0433] Example 7: This example illustrates the preparation of methyl N-[5-[6-[(7-fluoro-6-methoxy-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 63). Step 1: Preparation of 7-fluoro-6-methoxy-1,2,3,4-tetrahydroquinoline [ka] A colorless solution of 7-fluoro-6-methoxyquinoline (50.0 mg, 0.280 mmol, 1.00 equivalent) in ethanol (7.1 mL) was treated in an H-Cube® at a flow rate of 1 mL / min through a Pd / C cartridge at 40 bar H2 and 50°C. The reaction mixture was concentrated under reduced pressure to obtain 7-fluoro-6-methoxy-1,2,3,4-tetrahydroquinoline as a colorless solid. LC / MS (Method C) retention time = 0.38 min; [M+H] + =182 1 H NMR(400MHz,CDCl3)δ ppm 6.59(d,J=9.1Hz,1H),6.26(d,J=12.7Hz,1H),3.79(s,3H),3.16-3.32(m,2H),2.70(t,2H),1.84-1.99(m,2H).

[0434] Step 2: Preparation of methyl N-[5-[6-[7-fluoro-6-methoxy-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 63) [ka] (Compound 63) To a suspension of 3-[6-(methoxycarbonylamino)-3-pyridyl]imidazo[1,2-a]pyridine-6-carboxylic acid (75.0 mg, 0.240 mmol, 1.00 equivalent) and 7-fluoro-6-methoxy-1,2,3,4-tetrahydroquinoline (44.0 mg, 0.240 mmol, 1.00 equivalent) in acetonitrile (3.60 mL) and triethylamine (0.130 mL, 0.960 mmol, 4.00 equivalent), propylphosphonic anhydride (50% in ethyl acetate, 0.290 mL, 0.480 mmol, 2.00 equivalent) was added. The reaction mixture was stirred at room temperature for 16 hours, then quenched with a saturated aqueous solution of sodium bicarbonate and diluted with ethyl acetate. The mixture 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 using a silica gel cartridge (cyclohexane / (ethyl acetate / ethanol 3:1)) to obtain methyl N-[5-[6-[(7-fluoro-6-methoxy-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate as a white solid. LC / MS (Method C) Retention time = 0.70 min; [M+H] + =476 1 H NMR(400MHz,CDCl3)δ ppm 8.50(br s,1H),8.36-8.43(m,2H),8.11(d,J=8.72Hz,1H),7.73(s,1H),7.64(dd,J=8.54,2.36Hz,1H),7.54(d,J=9.45Hz,1H),7.09(dd, J=9.45,1.45Hz,1H),6.82(d,J=9.08Hz,1H),6.59-6.70(m,1H),3.90(s,3H),3.84-3.89(m,5H),2.79(t,2H),2.02-2.06(m,2H).

[0435] Example 8: This example illustrates the preparation of methyl N-[5-[6-[(6-fluoro-7-methoxy-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 64). Step 1: Preparation of 6-fluoro-7-methoxy-1,2,3,4-tetrahydroquinoline [ka] A colorless solution of 6-fluoro-7-methoxyquinoline (CAS 851985-93-8) (50.0 mg, 0.280 mmol, 1.00 equivalent) prepared as described, for example, in International Publication No. 2005047280, in ethanol (5.60 mL) was passed through a Pd / C cartridge at 1 mL / min at 30 bar and 40°C in an H-Cube®. A second run at 40 bar, 50°C and 1 mL / min was required. The reaction mixture was concentrated to obtain 6-fluoro-7-methoxy-1,2,3,4-tetrahydroquinoline as a colorless, rubbery substance. LC / MS (Method C) Retention time = 0.50 min; [M+H] + =182 1 H NMR(400MHz,CDCl3)δ ppm 6.68(d,J=11.99Hz,1H),6.11(d,J=7.63Hz,1H),3.80(s,3H),3.23-3.27(m,2H),2.66(t,2H),1.84-1.97(m,2H).

[0436] Step 2: Preparation of methyl N-[5-[6-[6-fluoro-7-methoxy-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 64) [ka] (Compound 64) To a suspension of 3-[6-(methoxycarbonylamino)-3-pyridyl]imidazo[1,2-a]pyridine-6-carboxylic acid (62.0 mg, 0.200 mmol, 1.00 equivalent) and 6-fluoro-7-methoxy-1,2,3,4-tetrahydroquinoline (36.0 mg, 0.200 mmol, 1.00 equivalent) in acetonitrile (2.00 mL) and triethylamine (0.110 mL, 0.790 mmol, 4.00 equivalent), propylphosphonic anhydride (50% in ethyl acetate, 0.240 mL, 0.400 mmol, 2.00 equivalent) was added. The reaction mixture was stirred at room temperature for 3 hours, then quenched with a saturated aqueous solution of sodium bicarbonate and further diluted with ethyl acetate. The mixture was extracted with ethyl acetate, the combined organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (cyclohexane / (ethyl acetate / ethanol 3:1)) to obtain methyl N-[5-[6-[(6-fluoro-7-methoxy-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate as a white solid. LC / MS (Method C) retention time = 0.72 min; [M+H] + =476 1 H NMR(400MHz,CDCl3)δ ppm 8.35-8.43(m,3H),8.14(d,J=8.4Hz,1H),7.74(s,1H),7.61-7.69(m,1H),7.59(d,J=9.5Hz,1H),7.16(dd,J=9.1,1.5Hz,1H),6.9 4(d,J=11.3Hz,1H),6.50-6.62(m,1H),3.89(t,J=6.5Hz,2H),3.86(s,3H),3.50(s,3H),2.77(t,J=6.7Hz,2H),1.99-2.04(m,2H).

[0437] Example 9: This example illustrates the preparation of methyl N-[5-[6-[(6-fluoro-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 66). Step 1: Preparation of (3-bromoimidazo[1,2-a]pyridine-6-yl)-(6-fluoro-3,4-dihydro-2H-quinoline-1-yl)methanone [ka] A mixture of 3-bromoimidazo[1,2-a]pyridine-6-carboxylic acid (200 mg, 0.830 mmol, 1.00 equivalent) and 6-fluoro-1,2,3,4-tetrahydroquinoline (CAS 59611-52-8; 192 mg, 1.25 mmol, 1.50 equivalent) in N,N-dimethylacetamide (5.00 mL) was mixed with N-ethyl-N-isopropyl-propan-2-amine (0.710 mL, 4.15 mmol, 5.00 equivalent) and propylphosphonic anhydride (50% in ethyl acetate, 1.24 mL, 2.07 mmol, 2.50 equivalent). The reaction mixture was stirred at 55°C for 35 minutes, then diluted with ethyl acetate and quenched with a saturated aqueous solution of sodium bicarbonate. The mixture 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 using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain (3-bromoimidazo[1,2-a]pyridine-6-yl)-(6-fluoro-3,4-dihydro-2H-quinoline-1-yl)methanone as a white solid. LC / MS (Method C) retention time = 0.88 min; [M+H] + =374 1 H NMR(400MHz,CDCl3)δ ppm 8.48(dd,J=1.6,0.9Hz,1H),7.68(s,1H),7.42(dd,J=9.5,0.7Hz,1H),6.96(br dd,J=8.4,2.9Hz,1H),6.93(br dd,J=9.5,1.5Hz,1H),6.75(br d,J=4.7Hz,1H),6.70-6.63(m,1H),3.96(t,J=6.7Hz,2H),2.89(t,J=6.5Hz,2H),2.15-2.06(m,2H).

[0438] Step 2: Preparation of methyl N-[5-[6-[6-fluoro-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate (compound 66) [ka] (Compound 66) Cesium carbonate (366 mg, 1.12 mmol, 1.50 equivalents) was added to a solution of (3-bromoimidazo[1,2-a]pyridine-6-yl)-(6-fluoro-3,4-dihydro-2H-quinoline-1-yl)methanone (280 mg, 0.748 mmol, 1.00 equivalent) and methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (307 mg, 1.12 mmol, 1.50 equivalents) in a mixture of 2-methyltetrahydrofuran (4.5 mL) and water (1.50 mL). The mixture was purged with argon for 5 minutes, then tetrakis(triphenylphosphine)palladium(0) (456 mg, 0.0370 mmol, 0.050 equivalents) was added, and the mixture was heated at 100°C for 1 hour under microwave irradiation. The mixture was cooled to room temperature, water was added, 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 in a silica gel cartridge (cyclohexane / (ethyl acetate / ethanol 3:1)) to obtain methyl N-[5-[6-[(6-fluoro-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyridine-3-yl]-2-pyridyl]carbamate. LC / MS (Method C) Retention time = 0.75 min; [M+H] + =446 1H NMR(400MHz,CDCl3)δ ppm 8.44-8.36(m,3H),8.15(d,J=8.7Hz,1H),7.75(s,1H),7.65(dd,J=8.7,2.2Hz,1H),7.51(d,J=9.5Hz,1H),7.03(dd,J=9.5,1.5Hz, 1H),6.98(dd,J=8.5,2.7Hz,1H),6.77-6.65(m,2H),3.92(t,J=6.5Hz,2H),3.87(s,3H),2.83(t,J=6.5Hz,2H),2.12-2.02(m,2H).

[0439] Example 10: This example illustrates the preparation of methyl N-[4-[6-[(2,4-difluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridine-3-yl]phenyl]carbamate (compound 78). Step 1: Preparation of methyl 3-(4-aminophenyl)imidazo[1,2-a]pyridine-6-carboxylate [ka] A mixture of 1,4-dioxane (57 mL) and water (5.7 mL) was mixed with methyl 3-bromoimidazo[1,2-a]pyridine-6-carboxylate (1.00 g, 3.80 mmol, 1.00 equivalent) and (4-aminophenyl)boronic acid salt (0.893 g, 4.94 mmol, 1.30 equivalent). Cesium carbonate (3.13 g, 9.51 mmol, 2.50 equivalent) was added to this stirred mixture. The mixture was purged with argon for 2 minutes, and cataCXium A Pd G3 (CAS 1651823-59-4, 0.146 g, 0.190 mmol, 0.050 equivalent) was added. The mixture was stirred at 80°C for 16 hours. The reaction mixture was cooled, diluted with ethyl acetate, quenched with a saturated solution of sodium bicarbonate, and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain methyl 3-(4-aminophenyl)imidazo[1,2-a]pyridine-6-carboxylate as a pale yellow solid. LC / MS (Method C) retention time = 0.41 min; [M+H] + =268 1 H NMR(400MHz,DMSO-d6)δ ppm 8.99(dd,J=1.8,1.1Hz,1H),7.69-7.74(m,1H),7.66(s,1H),7.63-7.66(m,1H),7.31-7.38(m,2H),6.83-6.88(m,2H),3.93(s,3H),3.91(br s,2H).

[0440] Step 2: Preparation of methyl 3-[4-(methoxycarbonylamino)phenyl]imidazo[1,2-a]pyridine-6-carboxylate [ka] Methyl chloroformate (614 mg, 6.43 mmol, 0.502 mL, 2.00 equivalent) was added dropwise to a mixture of methyl 3-(4-aminophenyl)imidazo[1,2-a]pyridine-6-carboxylate (905 mg, 3.22 mmol, 1.00 equivalent) and pyridine (1280 mg, 16.1 mmol, 1.31 mL, 5.00 equivalent) in ethyl acetate (36 mL). The reaction mixture was stirred at room temperature for 4 hours and then quenched with a saturated aqueous solution of sodium bicarbonate. The resulting solid was filtered and washed with water and ethyl acetate. The solid was dried under reduced pressure to obtain 3-[4-(methoxycarbonylamino)phenyl]imidazo[1,2-c]pyridine-6-carboxylate as a beige solid. LC / MS (Method C) retention time = 0.66 min; [M+H...

Claims

1. Equation (I) 【Chemistry 1】 (In the formula, Z is O or S, preferably Z is O) A 1 is CH or N, preferably 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 and -NHC(O)C 1-6 alkyl, and A 2 CR is independent 2 or N, provided there are three or fewer A's. 2 is N, preferably two or fewer A 2 is N, preferably one or less A 2 is N, and more preferably the four A 2 CR 2 The condition is that, 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-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 and C 1-6 Independently selected from alkylcarbonyls, the C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 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 and C 1-6 Each alkylcarbonyl group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs. A 3 CR is independent 3 or N, R 3 is selected from hydroxy, halogen, CN, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkoxy, C 2-6 alkenyl, C 2-6 alkynyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 alkyl, C 1-6 alkoxycarbonyl, C 1-6 alkylsulfanyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, amino, C 1-6 alkylamino, di-C 1-6 -alkylamino and C 3-6 cycloalkylamino, and each of the C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkoxy, C 2-6 alkenyl, C 2-6 alkynyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 alkyl, C 1-6 alkoxycarbonyl, C 1-6 alkylsulfanyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, amino, C 1-6 alkylamino, di-C 1-6 -alkylamino and C 3-6 cycloalkylamino group may each be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxy and CN, R 3 is adjacent to R 2 Together with these, a ring, preferably a 5- to 8-membered heterocycle, more preferably a 5-membered or 6-membered heterocycle, is arbitrarily formed. 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, 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 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 one to three substituents independently selected from halogens and CNs. A 3 and R 4 Together, they arbitrarily form a ring, preferably a 5-8 membered heterocycle, more preferably a 6-membered heterocycle, 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, the C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, diC 1-6 Alkylamino, C 1-6 Alkoxyaminos and C 1-6 Alkyl C 1-6 Each alkoxyamino group may be optionally substituted with one to three substituents independently selected from halogens and CNs. A compound of the same, or its salt or N-oxide.

2. R 1a , R 1b and R 1c is 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 and C 1-6 Alkoxy, preferably hydrogen and C 1-6 A compound according to claim 1, independently selected from alkyl groups.

3. R 1a and R 1c is hydrogen, and 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 and NHC(O)C 1-6 A compound according to claim 1, selected from alkyl groups.

4. 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, the C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 The compound according to any one of claims 1 to 3, wherein each alkylcarbonyl group may be optionally substituted with one to three substituents independently selected from halogen, hydroxyl, and CN.

5. R 3 is hydroxy, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, amino, C 1-6 Alkylamino, diC 1-6 - Alkylamino and C 3-6 Selected from cycloalkylaminos, the C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, amino, C 1-6 Alkylamino, diC 1-6 - Alkylamino and C 3-6 The compound according to any one of claims 1 to 4, wherein each cycloalkylamino group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs.

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

9. The four A's 2 CR 2 and A 3 CR 3 The compound according to any one of claims 1 to 5.

10. 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 and C 1-6 Selected from alkoxy, 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 Alkenil, C 2-6 Alkinyl and C 1-6 The compound according to any one of claims 1 to 9, wherein each alkoxy group may be optionally substituted with one to three substituents independently selected from halogens and CNs.

11. The compound of formula (I) is compound I-W1, I-W2, or I-W3: 【Transformation 6】 , moreover, 【Transformation 7】 (In the formula, R 3’ is hydrogen, C 1-6 Alkyl and C 3-6 Selected from cycloalkyl, the C 1-6 Alkyl and C 3-6 Each cycloalkyl group may be optionally substituted with one to three substituents independently selected from halogens and CNs. The compound according to any one of claims 1 to 5.

12. 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 The compound according to any one of claims 1 to 11, wherein each of the groups is selected from alkyl groups, and each of the groups may be optionally substituted with one to three substituents independently selected from halogens and CNs.

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

14. The composition according to claim 13, further comprising at least one compound selected from additional active ingredients, suitable formulation inactive ingredients, carriers, auxiliaries, and any mixture 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 attack by a plant pathogen, or a plant reproductive material thereof.

16. Formula (II) 【Transformation 8】 (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, and -NHC(O)C 1-6 Independently selected from alkyl groups, preferably R 1a and R 1c is hydrogen, and 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 1-6 Alkylsulfonyl and -NHC(O)C 1-6 Selected from alkyl groups, A 2 CR is independent 2 or N, provided there are three or fewer A's. 2 is N, preferably two or fewer A 2 is N, preferably one or less A 2 is N, and more preferably the four A 2 CR 2 The condition is that, 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-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 and C 1-6 Independently selected from alkylcarbonyls, the C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 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 and C 1-6 Each alkylcarbonyl group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs, preferably R 2 is hydrogen, halogen, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Selected independently from alkyl and CN, A 3 CR 3 or N, R 3 is hydroxy, 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 Alkoxycarbonyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, amino, C 1-6 Alkylamino, diC 1-6 - Alkylamino and C 3-6 Selected from cycloalkylaminos, the C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, 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, preferably R 3 is hydroxy, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Selected from alkoxycarbonyls, the C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Each alkoxycarbonyl group may be optionally substituted with one substituent selected from halogen, hydroxyl, and CN, R 3 is adjacent to R 2 Together with these, a ring, preferably a 5- to 8-membered heterocycle, more preferably a 5-membered or 6-membered heterocycle, is arbitrarily formed. 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, 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 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 one to three substituents independently selected from halogens and CNs, 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, the C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Each alkoxy group may be optionally substituted with one to three substituents, preferably one substituent, which can be independently selected from halogens and CNs. 3 and R 4 Together, they arbitrarily form a ring, preferably a 5-8 membered heterocycle, more preferably a 6-membered heterocycle, and X is Cl, Br, or I. A compound of the same or its salt or N-oxide, or Formula (XVII) 【Chemistry 9】 (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, and -NHC(O)C 1-6 Independently selected from alkyl groups, preferably R1a and R 1c is hydrogen, and 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 1-6 Alkylsulfonyl and -NHC(O)C 1-6 Selected from alkyl groups, A 2 CR is independent 2 or N, provided there are three or fewer A's. 2 is N, preferably two or fewer A 2 is N, preferably one or less A 2 is N, and more preferably the four A 2 CR 2 The condition is that, 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-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 and C 1-6 Independently selected from alkylcarbonyls, the C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 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 and C 1-6 Each alkylcarbonyl group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs, preferably R 2 is hydrogen, halogen, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Selected independently from alkyl and CN, A 3 CR 3 or N, R 3 is hydroxy, 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 Alkoxycarbonyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, amino, C 1-6 Alkylamino, diC 1-6 - Alkylamino and C 3-6 Selected from cycloalkylaminos, the C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, 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, preferably R 3 is hydroxy, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Selected from alkoxycarbonyls, the C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Each alkoxycarbonyl group may be optionally substituted with one substituent selected from halogen, hydroxyl, and CN, R 3 is adjacent to R 2 Together with these, a ring, preferably a 5- to 8-membered heterocycle, more preferably a 5-membered heterocycle or a 6-membered heterocycle, is arbitrarily formed, 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 1-6 Selected from alkyl and CN, 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 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 one to three substituents independently selected from halogens and CNs, 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, the C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Each alkoxy group may be optionally substituted with one to three substituents, preferably one substituent, which can be independently selected from halogens and CNs. 3 and R 4 They combine to form a ring, preferably a 5-8 membered heterocycle, more preferably a 6-membered heterocycle. A compound of the same, or its salt or N-oxide.

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