Imidazo[1,2-a]pyrazine derivatives

Abstract

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

Description

Technical Field

[0001] The present invention relates to a microbicidal activity, particularly a fungicidal activity, more specifically an activity against oomycetes, for example, a microbicidal imidazo[1,2-a]pyrazine derivative as an active ingredient. The present invention relates to the preparation of these imidazo[1,2-a]pyrazine derivatives, intermediates useful for the preparation of these imidazo[1,2-a]pyrazine derivatives, the preparation of these intermediates, pesticidal compositions containing at least one of the imidazo[1,2-a]pyrazine derivatives, the preparation of these compositions, and the use of imidazo[1,2-a]pyrazine 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.

Summary of the Invention

Problems to be Solved by the Invention

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

Means for Solving the Problems

[0003] Thus, in a first aspect, the present invention provides a compound of formula (I) which is preferably used as a fungicide

Chemical Formula

[0004] In a particular embodiment of this first aspect, the present invention relates to formula (I) as a fungicide. [ka] (In the formula, Z is O or S, preferably Z is O; A 1 is CH or N, preferably N; R 1a and R 1b These are independently 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 Selected from alkyl groups; preferably R 1a and R 1b is hydrogen; 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 On the condition that; R 2 These are independently 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 Selected from alkylcarbonyl, 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, C2-6 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 halogens, hydroxyls, and CNs; preferably, R 2 These are independently hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, and C 1-6 Selected from alkylcarbonyl, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, and C 1-6 Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; preferably, R 2 These are independently hydrogen, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6Alkoxy-C 1-6 Selected from 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 of the alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; more preferably, R 2 These are independently hydrogen, halogen, CN, and C 1-6 Alkyl and C 1-6 Selected from alkoxy; A 3 CR is independent. 3 or N; R 3 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 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 1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C1-6 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 cycloalkylamino group may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl, diC 1-6 Alkylaminocarbonyl-C 1-6 Selected from alkyl and CN, 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 1-6Alkyl, 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 They may optionally combine to form a ring, more preferably a 5- to 8-membered complex ring, more preferably a 6-membered complex ring; 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, 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. The compound may be a salt or N-oxide thereof.

[0005] In another specific embodiment of this first aspect, the present invention relates to formula (I) [ka] (In the formula, Z is O or S, preferably Z is O; A 1 is CH or N, preferably N; R 1a and R 1b These are independently 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 Selected from alkyl groups; preferably R 1a and R 1b is hydrogen; 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 On the condition that; R 2 These are independently 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 Selected from alkylcarbonyl, 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, C2-6 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 halogens, hydroxyls, and CNs; At least two R 2 Instead of hydrogen, the at least two R 2 Preferably, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Selected from 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 CN; more preferably, halogen, CN, C 1-6 Alkyl and C 1-6 Selected from alkoxy; A 3 CR is independent. 3 or N; R 3 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, C2-6 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 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 1-6 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 Alkylsulfonyl, amino, C 1-6 Alkylamino, diC 1-6 -alkylamino and C 3-6 Each cycloalkylamino group may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6Alkyl, 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; A 3 and R 4 They may optionally combine to form a ring, more preferably a 5- to 8-membered complex ring, more preferably a 6-membered complex ring; 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, and C 1-6 Alkyl C 1-6Selected from alkoxyaminos, each of the groups may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN. The compound may be a salt or N-oxide thereof.

[0006] In a second aspect, the present invention provides a pesticide composition comprising a compound of formula (I), more specifically, a pesticide composition comprising a fungicidally effective amount of a compound of formula (I). The composition may further comprise at least one compound selected from additional active ingredients, suitable inert ingredients, carriers, auxiliaries, and any mixtures thereof.

[0007] Compounds of formula (I) can be used to control plant pathogenic microorganisms. Therefore, to control plant pathogens, compounds of formula (I) according to the present invention, or compositions containing compounds of formula (I), can be applied directly to plant pathogens, to the habitats of plant pathogens, to plants particularly susceptible to attack by plant pathogens, or to the reproductive material of plants.

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

[0009] 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) or a composition containing a compound of formula (I), as described herein, to the plant pathogen, to the habitat of the plant pathogen, particularly to plants susceptible to attack by the plant pathogen, or to the reproductive material of the plant. According to this fourth aspect of the present invention, the method may exclude methods for treating the body of a human or animal by surgery or therapy.

[0010] 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) as described herein, or compositions comprising compounds of formula (I), for controlling plant pathogenic fungi, especially oomycetes.

[0011] 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) as described herein, or a composition containing a compound of formula (I), to the plant pathogenic fungi or the habitat of the plant pathogenic fungi (particularly plants susceptible to attack by plant pathogenic fungi, particularly oomycetes) or to the plant's reproductive material. According to this sixth aspect of the present invention, the method may exclude methods for treating the body of a human or animal by surgery or therapy.

[0012] When it is indicated that one group is substituted (for example, alkyl), this includes these groups that are part of the other groups, for example, alkyl in alkylthio.

[0013] 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.

[0014] - The term "amino" refers to the -NH2 group.

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

[0016] - The term "alkenyl," either alone or as part of a chemical group, preferably represents a linear or branched hydrocarbon having 2 to 6 carbon atoms and at least one double bond, such as vinyl, 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl- 2-Pentenyl, 4-Methyl-2-Pentenyl, 3-Methyl-3-Pentenyl, 4-Methyl-3-Pentenyl, 1-Methyl-4-Pentenyl, 2-Methyl-4-Pentenyl, 3-Methyl-4-Pentenyl, 4-Methyl-4-Pentenyl, 1,1-Dimethyl-2-Butenyl, 1,1-Dimethyl-3-Butenyl, 1,2-Dimethyl-2-Butenyl, 1,2-Dimethyl-3-Butenyl, 1,3-Dimethyl-2-Butenyl This represents methyl-2-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, and 1-ethyl-2-methyl-2-propenyl. An alkenyl group having 2 to 4 carbon atoms is preferred, for example, 2-propenyl, 2-butenyl, or 1-methyl-2-propenyl.

[0017] - 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, and 3-hexynyl This represents 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, and 2,5-hexadinyl. Alkynnyls having 2 to 4 carbon atoms are preferred, for example, ethynnyl, 2-propynyl, or 2-butynyl-2-propenyl.

[0018] - The term "haloalkyl" refers to an alkyl group that is substituted with one or more of the same or different halogen atoms as generally defined above, e.g., fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, or 2,2,2-trifluoroethyl.

[0019] - The term "cyanoalkyl" refers to an alkyl group that is substituted with one or more cyano groups, as generally defined above.

[0020] - The term "cycloalkyl," either alone or as part of a chemical group, preferably refers to a saturated or partially unsaturated monocyclic, bicyclic, or tricyclic hydrocarbon having 3 to 10 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, or adamantyl. Cycloalkyls having 3, 4, 5, 6, or 7 carbon atoms are preferred, such as cyclopropyl or cyclobutyl.

[0021] - The term "halocycloalkyl" refers to a cycloalkyl ring that is substituted by one or more of the same or different halogen atoms as defined above.

[0022] - The term "cyanocycloalkyl" refers to a cycloalkyl group that is substituted with one or more cyano groups as generally defined above.

[0023] - The term "alkoxy" is derived from the formula -OR a It refers to the base of, and in the formula, R a The alkoxy group is an alkyl group as generally defined above. Examples of alkoxy groups include, but are not limited to, methoxy, ethoxy, propoxy, iso-propoxy, 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.

[0024] - The term "alkylsulfanyl" is derived from the formula -SR a It refers to the base of, and in the formula, R a This is an alkyl group as generally defined above.

[0025] - The term "alkylsulfinyl" is derived from the formula -S(O)R a It refers to the base of, and in the formula, R a This is an alkyl group as generally defined above.

[0026] - The term "alkylsulfonyl" is derived from the formula -S(O)2R a It refers to the base of, and in the formula, R a This is an alkyl group as generally defined above.

[0027] - The term "alkoxycarbonyl" is derived from the formula R a It refers to the OC(O)- group, and in the formula, R a This is an alkyl group as generally defined above.

[0028] - The term "alkylamino" is derived from the formula R a It refers to the NH- group, and in the formula, R a This is an alkyl group as generally defined above.

[0029] - The term "cycloalkylamino" is derived from the formula R a It refers to the NH- group, and in the formula, R a This is a cycloalkyl group as generally defined above.

[0030] - The term "alkoxyamino" is derived from the formula R a It refers to the NH- group, and in the formula, R a This is an alkoxy group as generally defined above.

[0031] - The term "alkylaminocarbonyl" is derived from the formula R a It refers to the NHC(O)- group, and in the formula, R a This is an alkyl group as generally defined above.

[0032] - Hydroxyl or hydroxy represents the -OH group.

[0033] In relation to the present invention, the terms “to eradicate,” “to prevent,” or “to control,” and their variations thereof, mean reducing pathogenicity, more specifically plant pathogenicity, any undesirable effects such as fungi including oomycetes, exocytosis or attack on plants or plant-derived products, and pathogenic damage, to a level in which improvement is demonstrated.

[0034] As used herein, the term “effective amount” refers to the amount of a compound, its salt, or N-oxide that provides the desired effect in one or more applications.

[0035] The effective dose is readily determined by those skilled in the art by observing the results obtained using known techniques and under similar circumstances. Several factors are considered in determining the effective dose, 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 being applied; the type of application; and other relevant circumstances. [Modes for carrying out the invention]

[0036] Compounds of formula (I) having at least one basic center can form, for example, acid addition salts with strong inorganic acids, such as mineral acids, such as perchloric acid, sulfuric acid, nitric acid, nitrite, phosphoric acid, or hydrohalic acid; with strong organic carboxylic acids, such as unsubstituted or halogenated C1-4 alkane carboxylic acids, such as acetic acid; with saturated or unsaturated dicarboxylic acids, such as oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, or phthalic acid; with hydroxycarboxylic acids, such as ascorbic acid, lactic acid, malic acid, tartaric acid, or citric acid; or with organic sulfonic acids, such as unsubstituted or halogenated C1-4 alkanes or aryl sulfonic 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, mineral salts, alkali metal or alkaline earth metal salts, sodium, potassium or magnesium salts, or 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.

[0037] In each case, the compound of formula (I) according to the present invention exists in a free form, an oxidized form as an N-oxide, a covalently hydrated form, or a salt 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.

[0038] The compounds of formula (I) according to the present invention also include hydrates that may be formed during salt formation.

[0039] In further embodiments, compounds of formula (I) according to the present invention are provided, and R 1a and R 1b These are, independently, hydrogen and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxys; preferably, R 1a and R 1b It is hydrogen.

[0040] In further embodiments, compounds of formula (I) according to the present invention are provided, and R 3 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, 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 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 Each of the cycloalkylamino groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs. In preferred embodiments, R 3 It could be hydrogen.

[0041] In further embodiments, compounds of formula (I) according to the present invention are provided, wherein four A 2 CR 2 A 3 It is N.

[0042] In further embodiments, compounds of formula (I) according to the present invention are provided, wherein, [ka] teeth, [ka] Preferably, three A 2 CR 2 A 3 CR 3 That is the case.

[0043] In further embodiments, compounds of formula (I) according to the present invention are provided, wherein, [ka] teeth, [ka] Preferably, three A 2 CR 2 A 3 CR 3 That is the case.

[0044] In further embodiments, compounds of formula (I) according to the present invention are provided, wherein four A 2 CR 2 A 3 CR 3 Preferably, [ka] teeth, [ka] That is the case.

[0045] [ka] but [ka] In a particular embodiment, R 2 This is as defined in the present invention; preferably, R 2 These are independently hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, and C 1-6 Selected from alkylcarbonyl, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, and C 1-6 Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; preferably, R 2 These are independently hydrogen, halogen, CN, and C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Selected from alkoxy, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Each of the alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; more preferably, R 2 These are independently hydrogen, halogen, CN, and C 1-6 Alkyl and C 1-6 Selected from alkoxy.

[0046] In further embodiments, compounds of formula (I) according to the present invention are provided, where 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 1-6 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 independently selected from halogens and CN; and A 3 and R 4 These elements can optionally combine to form a ring, more preferably a 5- to 8-membered complex ring, or more preferably a 6-membered complex ring.

[0047] In further embodiments, compounds of formula (I) according to the present invention are provided, wherein 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] It forms one of the rings W1, W2, or W3 as described in the compound.

[0048] The carbon and / or nitrogen atoms forming the ring (W1, W2, or W3) are, in particular, R 3’ It may be substituted with 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. For example, the compounds of formula (I-W3) may be as follows: [ka]

[0049] In preferred embodiments, the compounds of formulas (I-W1), (I-W2), and (I-W3) may be as follows: [ka]

[0050] The carbon and / or nitrogen atoms forming the ring (W1, W2, or W3) are, in particular, R 3’ It may be substituted with R 3’ is hydrogen, C 1-6 Alkyl and C 3-6 Selected from cycloalkyl, C 1-6 Alkyl and C 3-6Each cycloalkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN. For example, the compounds of formula (I-W3) may be as follows: [ka]

[0051] In further embodiments, compounds of formula (I) according to the present invention are provided, where R 5 C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl and C 1-6 Alkoxy C 1-6 Selected from alkyl groups, each of the groups may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN.

[0052] In certain embodiments, a compound of formula (I) according to the present invention is provided, wherein, Z is O; A 1 is N; R 1a 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 from alkyl groups; preferably, R 1a is hydrogen; R 1b These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C1-6 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 from alkyl groups; preferably, R 1b is hydrogen; The four A's 2 CR 2 And; R 2 These are independently 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 Selected from alkylcarbonyl, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, and C 1-6 Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; preferably R 2 These are independently hydrogen, 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 Selected from alkoxy, C 1-6 Alkyl, C1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Each of the alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; more preferably, R 2 These are independently hydrogen, halogen, CN, and C 1-6 Alkyl and C 1-6 Selected from alkoxy; A 3 CR 3 And R 3 These are independently hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, 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 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 Each of the cycloalkylamino groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; preferably, R 3 is hydrogen; R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C1-6 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 independently selected from halogens and CN; A 3 and R 4 They can optionally come together to form a ring, more preferably a 5- to 8-membered complex ring, more preferably a 6-membered complex ring; 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 C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl and C 1-6 Alkoxy C 1-6 Selected from alkyl groups, each of the groups may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN.

[0053] In a preferred embodiment, [ka] teeth, [ka] And in the formula, R 2 This is as defined in the present invention; preferably, R 2 These are independently hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, and C 1-6 Selected from alkylcarbonyl, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, 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; more preferably, R 2 These are independently hydrogen, halogen, CN, and C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Selected from alkoxy, C 1-6 Alkoxy, C 1-6Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Each of the alkoxy groups may be optionally substituted with 1 to 3 substituents selected from halogens, hydroxyls, and CNs; more preferably, R 2 These are independently hydrogen, halogen, CN, and C 1-6 Alkyl and C 1-6 Selected from alkoxy.

[0054] In further embodiments, the compound according to the present invention is N-[5-[6-[(4-fluoro-3-methoxyphenyl)-(methoxymethyl)carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate; N-[5-[6-[cyanomethyl-(4-fluoro-3-methoxyphenyl)carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate; N-[5-[6-[(4-chloro-3-methoxyphenyl)-(cyanomethyl)carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate; N-[5-[6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate; N-(4-chlorophenyl)-3-[4-[[methoxy(methyl)carbamoyl]amino]phenyl]-N-methyl-imidazo[1,2-a]pyrazine-6-carboxamide; N-(4-chlorophenyl)-N-methyl-3-[4-(methylcarbamoylamino)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide; N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]phenyl]isopropyl carbamate; N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]phenyl]carbamate ethyl; N-[4-[6-[(4-cyanophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]phenyl]methyl carbamate; N-[4-[6-(5-chloroindoline-1-carbonyl)imidazo[1,2-a]pyrazine-3-yl]phenyl]acetamide; 3-(4-acetamidophenyl)-N-(4-chlorophenyl)-N-ethyl-imidazo[1,2-a]pyrazine-6-carboxamide; 3-(4-acetamidophenyl)-N-(3,4-dichlorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; 3-(4-acetamidophenyl)-N-(3,4-dimethylphenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; 3-(4-acetamidophenyl)-N-(2,4-dichlorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; 3-(4-acetamidophenyl)-N-(3-chlorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; 3-(4-acetamidophenyl)-N-methyl-N-[2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide; 3-(4-acetamidophenyl)-N-methyl-N-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide; 3-(4-acetamidophenyl)-N-methyl-N-[4-(trifluoromethoxy)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide; 3-(4-acetamidophenyl)-N-(2-chlorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; 3-(4-acetamidophenyl)-N-(4-methoxyphenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; 3-(4-acetamidophenyl)-N-(3-bromophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; 3-(4-acetamidophenyl)-N-(6-chloro-3-pyridyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; 3-(4-acetamidophenyl)-N-methyl-N-(3-pyridyl)imidazo[1,2-a]pyrazine-6-carboxamide; 3-(4-acetamidophenyl)-N-methyl-N-pyrimidine-2-ylimidazo[1,2-a]pyrazine-6-carboxamide; N-(4-chlorophenyl)-N-methyl-3-[4-[(2,2,2-trifluoroacetyl)amino]phenyl]imidazo[1,2-a]pyrazine-6-carboxamide; N-(4-chlorophenyl)-3-[4-[(2,2-difluoroacetyl)amino]phenyl]-N-methyl-imidazo[1,2-a]pyrazine-6-carboxamide; N-(4-chlorophenyl)-3-[4-[(2-methoxyacetyl)amino]phenyl]-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]phenyl]methyl carbamate; N-(4-chlorophenyl)-3-[4-[(1-fluorocyclopropanecarbonyl)amino]phenyl]-N-methyl-imidazo[1,2-a]pyrazine-6-carboxamide; N-(4-chlorophenyl)-3-[4-(cyclopropanecarbonylamino)phenyl]-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; N-(4-chlorophenyl)-N-methyl-3-[4-(2-methylpropanoylamino)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide; N-(4-chlorophenyl)-N-methyl-3-[4-(propanoylamino)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide; 3-[4-[acetyl(methyl)amino]phenyl]-N-(4-chlorophenyl)-N-methyl-imidazo[1,2-a]pyrazine-6-carboxamide; 3-(4-acetamidophenyl)-N-(4-bromophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; 3-(4-acetamidophenyl)-N-(4-chloro-2-fluorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; 3-(4-acetamidophenyl)-N-(4-cyanophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; 3-(4-acetamidophenyl)-N-(4-chlorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; 3-(4-acetamidophenyl)-N-(4-fluorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; N-[5-[6-[(4-methoxy-2-pyridyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate; N-[5-[6-[(4-chloro-3-methylphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate; N-[5-[6-[(4-acetamidophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate N-[5-[6-(6-fluoro-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate; N-[5-[6-[methyl-(3-methylsulfonylphenyl)carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate; 3-[6-(ethylcarbamoylamino)-3-pyridyl]-N-(4-fluoro-3-methoxyphenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; N-(4-fluoro-3-methoxyphenyl)-3-[4-[(2-methoxyacetyl)amino]phenyl]-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; 3-[4-(cyclopropanecarbonylamino)phenyl]-N-(4-fluoro-3-methoxyphenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; 3-[4-(ethylcarbamoylamino)phenyl]-N-(4-fluoro-3-methoxyphenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; 3-[4-(dimethylcarbamoylamino)phenyl]-N-(4-fluoro-3-methoxyphenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; N-[4-[6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]phenyl]benzyl carbamate; 3-[6-(cyclopropanecarbonylamino)-3-pyridyl]-N-(4-fluoro-3-methoxyphenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; 3-(4-acetamidophenyl)-N-(4-fluoro-3-methoxyphenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; 3-(6-acetamido-3-pyridyl)-N-(4-fluoro-3-methoxyphenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide; N-[5-[6-(6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-carbonyl)imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate; N-[5-[6-(7-fluoro-2,3-dihydro-1,4-benzoxazine-4-carbonyl)imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate; N-[5-[6-[(4-cyano-3-methoxyphenyl)-(methoxymethyl)carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate; N-[5-[6-[(4-cyanophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate; N-[5-[6-[(4-cyano-3-methylphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate; N-[4-[6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]phenyl]methyl carbamate; N-[4-[6-[(4-cyano-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]phenyl]methyl carbamate; and N-[5-[6-[(4-cyano-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate Selected from.

[0055] 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.

[0056] The compounds listed in Tables 1.1 to 1.45 below exemplify specific compounds of the present invention.

[0057] Table 1.1 shows equation (Ia) [ka] (In the formula, A 2a N is R 5 It is CH3, and R 2 , R 3 , R 4 , A 1 , A 2b This provides compounds E1.1 to E1.360 (as defined in Table Z).

[0058] More specifically, Table Z is R 3 and R 4 This also includes compounds in which the atoms combine to form a ring. In this case, the ring is formed by the R atoms bonded together along the amide atoms linked to the biring core of formula (Ia). 3 and R 4 This is shown in the column (Table Z). For example, the R of compound E1.29 3 and R 4 Please refer to the column.

[0059] [Table 1-1]

[0060] [Table 1-2]

[0061] [Table 1-3]

[0062] [Table 1-4]

[0063] [Table 1-5]

[0064] [Table 1-6]

[0065] Table 1-7

[0066] Table 1-8

[0067] Table 1-9

[0068] Table 1-10

[0069] Table 1-11

[0070] Table 1-12

[0071] Table 1-13

[0072] Table 1-14

[0073] Table 1-15

[0074] Table 1-16

[0075] [Table 1-17]

[0076] [Table 1-18]

[0077] [Table 1-19]

[0078] [Table 1-20]

[0079] [Table 1-21]

[0080] [Table 1-22]

[0081] Table 1.2 provides compounds E2.1 to E2.360 of formula (Ia), where A 2a N is R 5 It is OCH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0082] Table 1.3 provides compounds E3.1 to E3.360 of formula (Ia), where A 2a N is R 5 It is cyclopropyl, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0083] Table 1.4 provides compounds E4.1 to E4.360 of formula (Ia), wherein A 2a is N, and R 5 is CH2OCH3, and R 2 , R 3 , R 4 , A 1 , A 2b are as defined in Table Z.

[0084] Table 1.5 provides compounds E5.1 to E5.360 of formula (Ia), wherein A 2a is N, and R 5 is NHCH2CH3, and R 2 , R 3 , R 4 、A 1 、A 2b は、表Zで定義されるとおりである。

[0087] Table 1.8 provides compounds E8.1 to E8.360 of formula (Ia), wherein A 2a is CH, and R 5 is cyclopropyl, and R 2 , R 3 , R​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​4 , A 1 , A 2b This is defined in Table Z.

[0088] Table 1.9 provides compounds E9.1 to E9.360 of formula (Ia), where A 2a CH is, R 5 It is CH2OCH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0089] Table 1.10 provides compounds E10.1 to E10.360 of formula (Ia), where A 2a CH is, R 5 It is NHCH2CH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0090] Table 1.11 provides compounds E11.1 to E11.360 of formula (Ia), where A 2a is CF, R 5 It is CH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0091] Table 1.12 provides compounds E12.1 to E12.360 of formula (Ia), where A 2a is CF, R 5 It is OCH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0092] Table 1.13 provides compounds E13.1 to E13.360 of formula (Ia), where A 2ais CF, R 5 is cyclopropyl, R 2 , R 3 , R 4 , A 1 , A 2b is as defined in Table Z.

[0093] Table 1.14 provides compounds E14.1 to E14.360 of formula (Ia), wherein A 2a is CF, R 5 is CH₂OCH₃, R 2 , R 3 , R 4 , A 1 , A 2b is as defined in Table Z.

[0094] Table 1.15 provides compounds E15.1 to E15.360 of formula (Ia), wherein A 2a is CF, R 5 is NHCH₂CH₃, R 2 , R 3 , R 4 , A 1 , A 2b is as defined in Table Z.

[0095] Table 1.16 provides compounds E16.1 to E16.360 of formula (Ia), wherein A 2a is CCl, R 5 is CH₃, R 2 , R 3 , R 4 , A 1 , A 2b is as defined in Table Z.

[0096] Table 1.17 provides compounds E17.1 to E17.360 of formula (Ia), wherein A 2a is CCl, R 5 is OCH₃, R 2 , R 3 , R 4 , A 1 , A 2b is as defined in Table Z.

[0097] Table 1.18 provides compounds E18.1 to E18.360 of formula (Ia), where A 2a is CCl, and R 5 It is cyclopropyl, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0098] Table 1.19 provides compounds E19.1 to E19.360 of formula (Ia), where A 2a is CCl, and R 5 It is CH2OCH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0099] Table 1.20 provides compounds E20.1 to E20.360 of formula (Ia), where A 2a is CCl, and R 5 It is NHCH2CH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0100] Table 1.21 provides compounds E21.1 to E21.360 of formula (Ia), where A 2a It is CBr, and R 5 It is CH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0101] Table 1.22 provides compounds E22.1 to E22.360 of formula (Ia), where A 2a It is CBr, and R 5 It is OCH3, and R 2 , R 3, R 4 , A 1 , A 2b This is defined in Table Z.

[0102] Table 1.23 provides compounds E23.1 to E23.360 of formula (Ia), where A 2a It is CBr, and R 5 It is cyclopropyl, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0103] Table 1.24 provides compounds E24.1 to E24.360 of formula (Ia), where A 2a It is CBr, and R 5 It is CH2OCH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0104] Table 1.25 provides compounds E25.1 to E25.360 of formula (Ia), where A 2a It is CBr, and R 5 It is NHCH2CH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0105] Table 1.26 provides compounds E26.1 to E26.360 of formula (Ia), where A 2a It is CCH3, and R 5 It is CH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0106] Table 1.27 provides compounds E27.1 to E27.360 of formula (Ia), where A 2a It is CCH3, and R 5 It is OCH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0107] Table 1.28 provides compounds E28.1 to E28.360 of formula (Ia), where A 2a It is CCH3, and R 5 It is cyclopropyl, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0108] Table 1.29 provides compounds E29.1 to E29.360 of formula (Ia), where A 2a It is CCH3, and R 5 It is CH2OCH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0109] Table 1.30 provides compounds E30.1 to E30.360 of formula (Ia), where A 2a It is CCH3, and R 5 It is NHCH2CH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0110] Table 1.31 provides compounds E31.1 to E31.360 of formula (Ia), where A 2a It is CCH2CH3, and R 5 It is CH3, and R 2 , R 3 , R 4, A 1 , A 2b This is defined in Table Z.

[0111] Table 1.32 provides compounds E32.1 to E32.360 of formula (Ia), where A 2a It is CCH2CH3, and R 5 It is OCH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0112] Table 1.33 provides compounds E33.1 to E33.360 of formula (Ia), where A 2a It is CCH2CH3, and R 5 It is cyclopropyl, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0113] Table 1.34 provides compounds E34.1 to E34.360 of formula (Ia), where A 2a It is CCH2CH3, and R 5 It is CH2OCH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0114] Table 1.35 provides compounds E35.1 to E35.360 of formula (Ia), where A 2a It is CCH2CH3, and R 5 It is NHCH2CH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0115] Table 1.36 provides compounds E36.1 to E36.360 of formula (Ia), where A 2a It is CCN, and R 5 It is CH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0116] Table 1.37 provides compounds E37.1 to E37.360 of formula (Ia), where A 2a It is CCN, and R 5 It is OCH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0117] Table 1.38 provides compounds E38.1 to E38.360 of formula (Ia), where A 2a It is CCN, and R 5 It is cyclopropyl, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0118] Table 1.39 provides compounds E39.1 to E39.360 of formula (Ia), where A 2a It is CCN, and R 5 It is CH2OCH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0119] Table 1.40 provides compounds E40.1 to E40.360 of formula (Ia), where A 2a It is CCN, and R 5 It is NHCH2CH3, and R 2 , R 3 , R 4 , A1 , A 2b This is defined in Table Z.

[0120] Table 1.41 provides compounds E41.1 to E41.360 of formula (Ia), where A 2a It is COCH3, and R 5 It is CH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0121] Table 1.42 provides compounds E42.1 to E42.360 of formula (Ia), where A 2a It is COCH3, and R 5 It is OCH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0122] Table 1.43 provides compounds E43.1 to E43.360 of formula (Ia), where A 2a It is COCH3, and R 5 It is cyclopropyl, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0123] Table 1.44 provides compounds E44.1 to E44.360 of formula (Ia), where A 2a It is COCH3, and R 5 It is CH2OCH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0124] Table 1.45 provides compounds E45.1 to E45.360 of formula (Ia), where A 2aIt is COCH3, and R 5 It is NHCH2CH3, and R 2 , R 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0125] The compounds according to the present invention may have numerous advantages, including, in particular, advantageous levels of biological activity for protecting plants from fungal diseases, or excellent properties for use as agricultural chemical active ingredients (e.g., high biological activity, advantageous activity spectrum, increased safety profile, improved physicochemical properties, or improved biodegradability). The compounds according to the present invention have particularly advantageous levels of biological activity for protecting plants from oomycetes such as Phytophthora, Plasmopara, and Pythium.

[0126] Compounds of formula (I) where Z is O can be prepared as shown in schemes 1 to 13 below, and in these, unless otherwise specified, the definition of each variable element is as defined in the present invention.

[0127] The compound of formula (I) is prepared 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, [1,1-bis(diphenylphosphineno)ferrocene]dichloropalladium(II), bis(diphenylphosphine)palladium(II) chloride, palladium dichloride, or palladium acetate, in a suitable solvent such as dimethylformamide, dioxane, tetrahydrofuran, ethanol, or water, and the compound of formula (II) (wherein X is Cl, Br, or I) and the compound of formula (III) (wherein R 6 They are independently hydrogen, C1-6 alkyl, or two R 6 It can be prepared via Suzuki cross-coupling (which can combine to form a C3-8 cycloalkyl group). 6Either they are hydrogen, C1-6 alkyl, or two R 6 Compounds of formula (III) that can combine to form a C3-8 cycloalkyl group are prepared by known methods or are commercially available. This transformation is shown in Scheme 1. [ka] Scheme 1

[0128] Alternatively, the compound of formula (I) can be prepared by the direct arylation of the compound of formula (IV) with the compound of formula (V) (wherein X is Cl, Br, or I) in the presence of a catalyst such as palladium diacetate, a ligand such as triphenylphosphine or (dicyclohexylphosphino)biphenyl, and a base such as cesium carbonate or potassium carbonate. This coupling reaction is shown in Scheme 2. [ka] Scheme 2

[0129] Compound (II) (wherein X is Cl, Br, or I) is reacted with compound (VI) (wherein X is Cl, Br, or I) in the presence of a base such as Cs2CO3, K2CO3, NaH, or NaOtBu, and compound (VI) (wherein X is Cl, Br, or I) is reacted with reagent (VII) (wherein X 1 It can be prepared by reacting with a good leaving group such as Cl, Br, I, triflate, tosyl, or mesyl. Compound of formula (VIII) (wherein R 7 A (wherein X is an electron-withdrawing group such as a cyano or ester) can optionally be used to functionalize the amide nitrogen in the presence of a base such as triethylamine or 1,8-diazabicyclo[5.4.0]undeca-7-ene. The compound of formula (VI) (wherein X is Cl, Br or I) is the compound of formula (IX) (wherein X 2It can be prepared by a peptide coupling reaction between the amine of formula (X) and the compound of formula (IX) (where X is OH and X is Cl, Br, or I), preferably in a suitable solvent (e.g., N-methylpyrrolidone, acetonitrile, dimethylacetamide, dichloromethane, or tetrahydrofuran), preferably at a temperature of 25°C to 60°C, optionally in the presence of a base such as triethylamine or N,N-diisopropylethylamine; or alternatively, in a suitable solvent (e.g., acetonitrile), optionally in the presence of a base (e.g., triethylamine or N,N-diisopropylethylamine), under conditions described in the literature for amide coupling such as 1-propanephosphonic acid cyclic anhydride (T3P), by converting the -OH of the carboxylic acid to a good leaving group such as a chloride group by using, for example, (COCl)2 or SOCl2 before treatment with the amine of formula (X). For example, see Chem.Soc.Rev.2009,38,606 and Chem.Soc.Rev.2011,40,5084. Alternatively, a compound of formula (II) (wherein X is Cl, Br, or I) can be a compound of formula (IX) (wherein X) using the above conditions. 2 This can be obtained by amide coupling transformations between (where is OH and X is Cl, Br, or I) and the amine of formula (XI). These transformations are shown in Scheme 3. [ka] Scheme 3

[0130] The compound of formula (XI) is commercially available or, in the presence of a base such as Cs2CO3, K2CO3, NaH, or NaOtBu, is the compound of formula (X) and the compound of formula (VII) (wherein X 1The compound of formula (XI) can also be obtained by reaction with a good leaving group such as Cl, Br, I, triflate, tosyl, or methyl. Alternatively, the compound of formula (X) can also be obtained by reaction with the compound of formula (VIII) (wherein R is a good leaving group such as Cl, Br, I, triflate, tosyl, or methyl). 7 The compound of formula (XI) can be synthesized by reacting it with an electron-withdrawing group (such as a cyano or ester). Alternatively, the compound of formula (XI) can be synthesized by reacting it with an aldehyde of formula (XII) (wherein R is present in a suitable solvent, optionally in the presence of a Brønsted or Lewis acid such as acetic acid, for example, in the presence of NaBH(OAc)3 or NaBH3CN. 8 C 1-5 Alkyl, C 1-6 Alkoxy-C 1-5 Alkyl, C 3-6 Cycloalkyl-C 1-3 Alkyl, C 1-5 Alkenil, C 1-5 Alkinyl, C 1-5 Alkoxy, C 1-6 Alkylsulfanyl-C 1-5 Alkyl, C 1-6 Alkylsulfinyl-C 1-5 Alkyl, C 1-6 Alkylsulfonyl-C 1-5 Alkyl, C 1-6 Alkoxycarbonyl-C 1-5 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-5 Alkyl, diC 1-6 Alkylaminocarbonyl-C 1-5 It can be obtained from the amine of formula (X) by reductive amination with an alkyl group (selected from alkyl groups). Alternatively, another reagent system for reductive amination uses a combination of titanium isopropoxide and NaBH4. The synthesis of the compound of formula (XI) from the amine of formula (X) is shown in Scheme 4. [ka] Scheme 4

[0131] Compound of formula (IX) (wherein X2 (wherein XIII) is a commercially available compound of formula (XIII) (wherein X is OH and X is Cl, Br or I) using a halogenating agent such as N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide or bromine in a suitable solvent such as dichloromethane, chloroform, tetrahydrofuran or acetonitrile. 2 It can be obtained by halogenation of the compound of formula (XIII) (wherein X is OH). 2 The compound (wherein X is OH) can be commercially available or prepared using methods generally known to those skilled in the art. Alternatively, the compound of formula (IX) (wherein X is OH) can be prepared. 2 A compound of formula (XIV) (wherein X is OH and X is Cl, Br or I) is formed by using a base such as lithium hydroxide or sodium hydroxide (wherein X is Cl, Br or I and R is OH) 9 C 1-6 It can be obtained by hydrolysis of the ester functional group of alkyl. Compound of formula (XIV) (wherein X is Cl, Br or I, and R 9 C 1-6 (It is alkyl) is commercially available or can be used to form a compound of formula (XV) (wherein R is R) using a halogenating agent according to the above conditions. 9 C 1-6 It can be prepared by halogenation of an alkyl compound (wherein R 9 C 1-6 Alkyl compounds can be prepared using commercially available methods or methods commonly known to those skilled in the art. These conversions are shown in Scheme 5. [ka] Scheme 5

[0132] Alternatively, the compound of formula (II) (wherein X is Cl, Br, or I) can be prepared by the reaction of the compound of formula (IV) with a halogenating agent such as N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, or bromine in a suitable solvent such as dichloromethane, chloroform, tetrahydrofuran, or acetonitrile. The compound of formula (IV) is prepared by the reaction of the compound of formula (XIII) (wherein X 2 The ion is formed by amide-coupling conversion of the amine of formula (X) and the compound of formula (XIII) (where X is OH), preferably in a suitable solvent (e.g., N-methylpyrrolidone, acetonitrile, dimethylacetamide, dichloromethane, or tetrahydrofuran), preferably at 25°C. The compound of formula (IV) can be obtained by a process that is usually carried out by converting the -OH group of the carboxylic acid to a good leaving group such as a chloride group by using, for example, (COCl)2 or SOCl2 before treatment with the amine of formula (XI), under conditions described in the literature for amide coupling such as 1-propanephosphonic acid cyclic anhydride (T3P), at a temperature of ~60°C, optionally in the presence of a base such as triethylamine or N,N-diisopropylethylamine; or alternatively, in a suitable solvent (e.g., acetonitrile), optionally in the presence of a base (e.g., triethylamine or N,N-diisopropylethylamine). Alternatively, the compound of formula (IV) can be obtained by the compound of formula (VII) (wherein X, X) in the presence of a base such as Cs2CO3, K2CO3, NaH or NaOtBu. 1 The compound of formula (IV) can also be obtained by alkylation with a good leaving group such as Cl, Br, I, triflate, tosyl, or methyl. Alternatively, the compound of formula (IV) can also be obtained by alkylating the compound of formula (XVI) with the compound of formula (VIII) (wherein R is a good leaving group such as Cl, Br, I, triflate, tosyl, or methyl). 7 The compound of formula (XVI) can be synthesized by reacting it with an electron-withdrawing group such as a cyano or ester. The compound of formula (XIII) (wherein X is used) with an amine of formula (X) using the above conditions. 2It can be prepared by peptide-coupling conversion from (OH). These conversions are shown in Scheme 6. [ka] Scheme 6

[0133] Alternatively, the compound of formula (IV) can be synthesized by reacting the compound of formula (XVII) (wherein X is Cl, Br, or I) with the amine of formula (XI) and carbon monoxide in the presence of a catalyst such as 1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) and optionally a base such as triethylamine. This transformation is shown in Scheme 7. [ka] Scheme 7

[0134] Alternatively, the compound of formula (I) is the compound of formula (XVIII) (wherein X 2 It can be prepared by a process that is usually carried out by converting the -OH of the carboxylic acid to a good leaving group such as a chloride group by using, for example, (COCl)2 or SOCl2 before treatment with the amine of formula (XI), preferably by amide-coupling conversion of the amine of formula (XI) and by activating the carboxylic acid functional group of the compound of formula (XVIII), preferably in a suitable solvent (e.g., N-methylpyrrolidone, acetonitrile, dimethylacetamide, dichloromethane or tetrahydrofuran), preferably at a temperature of 25°C to 60°C, optionally in the presence of a base such as triethylamine or N,N-diisopropylethylamine; or alternatively, in a suitable solvent (e.g., acetonitrile), optionally in the presence of a base (e.g., triethylamine or N,N-diisopropylethylamine), under conditions described in the literature for amide coupling such as 1-propanephosphonic acid cyclic anhydride (T3P). Alternatively, the compound of formula (I) is the compound of formula (VII) (wherein X) in the presence of a base such as Cs2CO3, K2CO3, NaH, or NaOtBu.1 The compound of formula (I) can also be prepared by alkylation with a good leaving group such as Cl, Br, I, triflate, tosyl, or methyl. Alternatively, the compound of formula (I) can also be optionally converted to the compound of formula (XIX) in the presence of a base such as triethylamine or 1,8-diazabicyclo[5.4.0]undeca-7-ene (wherein R is a good leaving group). 7 The compound of formula (XIX) can be synthesized by reacting it with an electron-withdrawing group such as a cyano or ester. The compound of formula (XIX) can be synthesized by reacting it with the compound of formula (XVIII) (wherein X is used) under the above conditions. 2 It can be synthesized by peptide-coupling conversion from the amine of formula (X), where ( is OH). These conversions are shown in Scheme 8. [ka] Scheme 8

[0135] Compound of formula (XVIII) (wherein X 2 (where R is OH) is a compound of formula (XX) (where R is in the formula) 9 C 1-6 It can be obtained by hydrolysis of the ester portion of the alkyl group. Compound of formula (XX) (wherein R 9 C 1-6 A compound of formula (XV) (wherein R is alkyl) is found in the presence of a catalyst such as palladium diacetate, a ligand such as triphenylphosphine or (dicyclohexylphosphine)biphenyl, and a base such as cesium carbonate or potassium carbonate. 9 C 1-6 It can be prepared by direct arylation with a compound of formula (V) (wherein X is Cl, Br, or I) (which is alkyl). Alternatively, a compound of formula (XX) (wherein R 9 C 1-6The alkyl compound (wherein XIV) is prepared 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, [1,1-bis(diphenylphosphine)ferrocene]dichloropalladium(II), bis(diphenylphosphine)palladium(II) chloride, palladium dichloride, or palladium acetate, in a suitable solvent such as dimethylformamide, dioxane, tetrahydrofuran, ethanol, or water, and R 9 C 1-6 Compounds of formula (III) (wherein R is alkyl) and compounds of formula (III) 6 They are independently hydrogen, C1-6 alkyl, or two R 6 These can be obtained from Suzuki cross-coupling (which can combine to form C3-8 cycloalkyl groups). These transformations are shown in Scheme 9. [ka] Scheme 9

[0136] Alternatively, the compound of formula (I) can be synthesized by reacting the compound of formula (XXI) (wherein X is Cl, Br, or I) with the amine of formula (XI) and carbon monoxide in the presence of a catalyst such as [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) and optionally a base such as triethylamine. The compound of formula (XXI) (wherein X is Cl, Br, or I) can be synthesized by reacting the compound of formula (III) (wherein R) 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, [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II), bis(diphenylphosphine)palladium(II) chloride, palladium dichloride, or palladium acetate. 6 They are independently hydrogen, C1-6 alkyl, or two R 6The compounds of formula (XXII) (wherein X is independently Cl, Br, or I) can be prepared via Suzuki cross-coupling of (which together can form C3-8 cycloalkyl groups). These transformations are shown in Scheme 10. [ka] Scheme 10

[0137] Alternatively, the compound of formula (I) can be used in a peptide coupling transformation with the compound of formula (XXIII) and formula (XXIV) (wherein X) using the above conditions. 2 The compounds of formula (XXIII) can be prepared by the reaction of compounds of formula (wherein X is OH). The compounds of formula (XXIII) are prepared in the presence of a base such as Cs2CO3, K2CO3 or NaOtBu, and in the presence of a suitable palladium catalyst such as bis(diphenylphosphine)ferrocene]dichloropalladium(II), tetrakistriphenylphosphinenopalladium, chloride [1,1-bis(diphenylphosphine)dichloropalladium(II), palladium dichloride or palladium acetate, in a suitable solvent such as dimethylformamide, dioxane, tetrahydrofuran, ethanol or water, by the reaction of the compound of formula (II) (wherein X is Cl, Br or I) and the compound of formula (XXV) (wherein R 6 They are independently hydrogen, C1-6 alkyl, or two R 6 It can be prepared via Suzuki cross-coupling (which can combine to form a C3-8 cycloalkyl group). 6 Either they are hydrogen, C1-6 alkyl, or two R 6 Compounds of formula (XXV) that can combine to form C3-8 cycloalkyl groups are prepared by known methods or are commercially available. These transformations are shown in Scheme 11. [ka] Scheme 11

[0138] The compound of formula (Ib) (wherein Z is S) can be prepared by the reaction of the compound of formula (I) (wherein 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 12. [ka] Scheme 12

[0139] Alternatively, the compound of formula (Ib) (wherein Z is S) can be used in a peptide coupling transformation with the compound of formula (XXIIIb) and the compound of formula (XXIV) (wherein X) using the above conditions. 2 The compound of formula (XXIIIb) can be prepared by the reaction of a compound of formula (XXIII) with phosphorus pentasulfide or Lawson's reagent (CAS: 19172-47-5) in a suitable solvent such as toluene, xylene, or dichloromethane. This transformation is shown in Scheme 13. [ka] Scheme 13

[0140] It will be understood by those skilled in the art 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 by those skilled in the art.

[0141] When the term "compound / compounds according to the present invention" is used, it refers to the compounds according to the present invention.

[0142] 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.

[0143] Compounds according to the present invention can be converted to other compounds according to the present invention in a manner known by themselves by replacing one or more substituents of the starting compound according to the present invention with other substituents according to the present invention in a conventional manner.

[0144] Depending on the selection of suitable reaction conditions and starting materials in each case, for example, in one reaction step, it may be possible to replace only one substituent with another substituent according to the present invention, or multiple substituents may be replaced with other substituents according to the present invention in the same reaction step.

[0145] 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.

[0146] The salts of the compounds according to the present invention can be converted to the free compounds by conventional methods, for example, by treating the acid addition salt with a suitable basic compound or a suitable ion exchange reagent, and by treating the salt with a base with a suitable acid or a suitable ion exchange reagent.

[0147] Salts of the compounds according to the present invention can be converted to other salts of the compounds according to the present invention, acid addition salts, for example, other acid addition salts, by methods known to the present invention, for example, by treatment of an inorganic acid salt, such as a silver acetate hydrochloride, with a suitable metal salt of the acid, such as a sodium, barium, or silver salt of the acid, in a suitable solvent (for example, an inorganic salt that forms silver chloride insoluble therein and therefore precipitates from the reaction mixture).

[0148] 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.

[0149] In each case, the compounds according to the present invention, in free form or salt form, and, where appropriate, their tautomers, may exist in one form of possible isomers or as mixtures thereof, depending on the number, absolute and relative configuration of chiral carbon atoms present in the molecule and / or the stereoconfiguration of non-aromatic double bonds present in the molecule, in the form of pure isomers, such as anticarpone and / or diastereomers, or as stereoisomer mixtures, such as enantiomer mixtures, such as racemic compounds, diastereomer mixtures or racemic compound mixtures; the present invention relates to pure stereoisomers and to all possible isomer mixtures, and in all cases in this sense, even when stereochemical details are not specifically described in any case, it should be understood in this sense in the above and below herein.

[0150] The diastereomer or racemic mixture of compounds according to the present invention, in the free or salt form obtained depending on the selected starting materials and procedure, can be separated into pure diastereomers or racemic compounds by known methods based on the physicochemical differences of the components, for example by fractional crystallization, distillation and / or chromatography.

[0151] Enantiomer mixtures such as racemates, which can be obtained by a similar method, can be separated into optical counterparts by known methods, such as recrystallization from an optically active solvent, chromatography on a chiral adsorbent, such as high-performance liquid chromatography (HPLC) on acetylcellulose, cleavage with specific immobilized enzymes using suitable microorganisms, formation of inclusion compounds, for example, using a chiral crown ether that complexes with only one enantiomer, or conversion to a diastereomer salt. This can be achieved by reacting the racemate, for example, a basic final product, with an optically active acid, such as a carboxylic acid, such as camphor, tartaric acid, or malic acid, or a sulfonic acid, such as camphorsulfonic acid. The diastereomer mixture thus obtained can then be separated to obtain diastereomers, for example, by fractional crystallization based on their different solubility (from which the desired enantiomer can be liberated by the action of a suitable reagent, such as a basic reagent).

[0152] Pure diastereomers or enantiomers can be obtained according to the present invention not only by separating a suitable mixture of stereoisomers, but also by generally known diastereoselective or enantioselective synthesis methods, such as the method according to the present invention using suitable stereochemical starting materials.

[0153] 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, for example from J.Med.Chem.,32(12),2561-73,1989 or International Publication No. 00 / 15615.

[0154] When individual components have different biological activities, it is advantageous to isolate or synthesize the more biologically effective stereoisomers, such as enantiomers or diastereomers, or stereoisomer mixtures, such as enantiomer mixtures or diastereomer mixtures, in each case.

[0155] The compounds according to the present invention and, optionally, their tautomers may be obtained in free form or salt form, and optionally in hydrate form, and / or in other solvents, such as solvents that have been used to crystallize compounds existing in solid form.

[0156] The following examples illustrate, but are not limited to, the present invention.

[0157] The present invention also provides intermediates useful for preparing the compounds according to the present invention.

[0158] The following intermediates form further embodiments of the present invention.

[0159] Formula (XXIII) [ka] (In the formula, Z is O or S, preferably Z is O; A 1 is CH or N, preferably N; R 1a and R 1b These are independently 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 from alkyl groups; preferably R 1a and R 1b is hydrogen; 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 2is N, and more preferably four A 2 CR 2 On the condition that; R 2 These are independently 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 Selected from alkylcarbonyl, 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 halogens, hydroxyls, and CNs; preferably, R 2These are independently hydrogen, 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 Selected from 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 of the alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; more preferably, R 2 These are independently hydrogen, halogen, CN, and C 1-6 Alkyl and C 1-6 Selected from alkoxy; at least two R 2 However, preferably, it is not hydrogen; A 3 CR is independent. 3 or N; R 3 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 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 1-6Alkyl, 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 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 halogens, hydroxyls, and CNs; preferably, R 3 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, 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 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 Each of the cycloalkylamino groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; more preferably, R 3 is hydrogen; 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, 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; and A3 and R 4 (These elements can optionally combine to form a ring, more preferably a 5-8 membered heteroring, more preferably a 6-membered heteroring.) Compounds of the same; or salts or N-oxides thereof.

[0160] Formula (IV) [ka] (In the formula, Z is O or S, preferably Z is O; R 1a and R 1b These are independently 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 from alkyl groups; preferably R 1a and R 1b is hydrogen; 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 On the condition that; R 2 These are independently 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, C2-6 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 Selected from alkylcarbonyl, 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 halogens, hydroxyls, and CNs; preferably, R 2 These are independently hydrogen, 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 Selected from alkoxy, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6Each of the alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; more preferably, R 2 These are independently hydrogen, halogen, CN, and C 1-6 Alkyl and C 1-6 Selected from alkoxy; A 3 CR is independent. 3 or N; at least two R 2 Preferably, it is not hydrogen; R 3 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 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 1-6 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 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 halogens, hydroxyls, and CNs; preferably, R 3 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, 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 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 Each of the cycloalkylamino groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; more preferably, R 3 is hydrogen; 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; and A 3 and R 4 (These elements can optionally combine to form a ring, more preferably a 5-8 membered heteroring, more preferably a 6-membered heteroring.) Compounds of the same; or salts or N-oxides thereof.

[0161] Formula (II) [ka] (In the formula, Z is O or S, preferably Z is O; R1a and R 1b These are independently 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 from alkyl groups; preferably R 1a and R 1b is hydrogen; 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 On the condition that; R 2 These are independently 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 Selected from alkylcarbonyl, C1-6 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 halogens, hydroxyls, and CNs; preferably, R 2 These are independently hydrogen, 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 Selected from 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 of the alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; more preferably, R 2 These are independently hydrogen, halogen, CN, and C 1-6 Alkyl and C 1-6 Selected from alkoxy; at least two R 2 However, preferably, it is not hydrogen; A 3 CR is independent. 3 or N; R3 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 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 1-6 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 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 halogens, hydroxyls, and CNs; preferably, R 3 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, C3-6 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 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 Each of the cycloalkylamino groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; more preferably, R 3 is hydrogen; 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, C 1-6 Alkyl, C1-6 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; A 3 and R 4 They may optionally combine to form a ring, more preferably a 5- to 8-membered complex ring, more preferably a 6-membered complex ring; and X is Cl, Br, or I; Compounds of the same; or salts or N-oxides thereof.

[0162] Formula (XVIII) [ka] (In the formula, A 1 is CH or N, preferably N; R 1a and R 1b These are independently 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, C1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Selected from alkyl groups; preferably R 1a and R 1b is hydrogen; 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, 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. Compounds of the same; or salts or N-oxides thereof.

[0163] Formula (XX) [ka] (In the formula, A 1 is CH or N, preferably N; R 1a and R 1b These are independently 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 from alkyl groups; preferably R 1a and R 1bis hydrogen; 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; and R 9 C 1-6 (It is alkyl.) Compounds of the same; or salts or N-oxides thereof.

[0164] Formula (XXI) [ka] (In the formula, A 1 is CH or N, preferably N; R 1a and R 1b These are independently 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 from alkyl groups; preferably R 1a and R 1b is hydrogen; R 5 C 1-6 Alkyl, C 1-6 Alkoxy, C3-6 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; and X is Cl, Br, or I; Compounds of the same; or salts or N-oxides thereof.

[0165] The compounds of formula (I) as defined in this invention can 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. These novel compounds are distinguished by their excellent activity at low application rates, the fact that plants exhibit sufficient tolerance, and their environmental safety. They possess highly useful therapeutic, preventive, and systemic properties and can be used to protect many cultivated plants. Compounds of formula (I) as defined in this invention can also be used to suppress or eradicate pathogens appearing on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of different crops of useful plants, while simultaneously protecting those parts of the plant that will grow later from plant pathogenic microorganisms.

[0166] Compounds of formula (I) as defined in the present invention may also be used as mycicides. As used herein, the term “mycicide” means a compound that controls, modifies, or prevents the growth of fungi. The term “mycicidal amount” means the amount of such compound or combination of such compounds that can produce an effect against the growth of fungi. Controlling or modifying effects include all deviations from natural occurrence, such as fungicidal or delayed growth, while prevention includes the formation of barriers or other defenses in plants to prevent fungal infections.

[0167] For protection against fungal infections and plant pathogenic fungi occurring in the soil, the compounds of formula (I) as defined in this invention may also be used as coating agents for treating plant propagation materials, such as seeds such as fruits, tubers or grains, 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 compounds of formula (I) as defined in this invention may also be applied to grains (coated) either by impregnating the seeds in a liquid formulation or by coating the seeds with a solid formulation. The composition may also be applied to the planting site when the propagation material is planted, for example, in the sowing furrow during sowing. This invention also relates to such methods for treating plant propagation materials and to plant propagation materials treated in this manner.

[0168] Furthermore, the compounds of formula (I) as defined in the present invention can be used to control fungi in related fields, for example, in the protection of industrial materials including wood and wood-related industrial products, food storage, and hygiene management.

[0169] In addition, the present invention can be used, for example, to protect non-biological materials such as timber, wall panels, and paints from fungal attacks.

[0170] 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 a wide range of plant diseases, including leaf pathogens of ornamental plants, turfgrasses, vegetables, crops, grains, and fruit crops.

[0171] The fungi and fungal vectors, as well as plant pathogenic bacteria and viruses, that can be controlled for these diseases include, for example, the following: This includes species such as Absidia corymbifera, Alternaria spp., Aphanomyces spp., Ascochyta spp., Aspergillus spp. (including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus), Aureobasidium spp. (including A. pullulans), Blastomyces dermatitidis, Blumeria graminis, and Bremia lactucaea. This includes species of the genus Botryosphaeria (including B. lactucae, B. dothidea, and B. obtusa), species of the genus Botrytis (including B. cinerea), species of Candida (including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, and C. tropicalis), species of Cephaloascus fragrans, and species of Ceratocystis. Cercospora spp. (including C. arachidicola), Cercosporidium personatum, Cladosporium spp., Claviceps purpurea, Coccidioides immitis, Cochliobolus spp., and Colletotrichum spp., including C. musae. Cryptococcus neoformans, Diaporthe spp., Didymella spp., Drechslera spp., Elsinoe spp. This includes species of the genus Epidermophyton (spp.), Erwinia amylovora, and Erysiphe species, including 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. including H. capsulatum, Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium sediciosum This includes species such as *Mycosphaerella* (including *M. graminicola*), *Microdochium nivale*, *Microsporum*, *Monilinia*, *Mucor*, *M. graminicola*, and *M. pomi*.), Oncobasidium theobromaeon, Ophiostoma piceae, species of the genus Paracoccidioides spp., species of the genus Penicillium including P. digitatum and P. italicum, species of the genus Petriellidium spp., species of Peronosclerospora including P. maydis, P. philippinensis and P. sorghi, species of Peronospora spp., species of Peronospora, wheat blight fungus (Phaeosphaeria) *Phonophora nodorum*, Phakopsora pachyrhizi, Phellinus igniarus, *Phialophora* spp., *Phoma* spp., *Phomopsis viticola*, *Phytophthora* spp. including *P. infestans*, *Plasmopara* spp. including *P. halstedii*, *P. viticola*, *Pleospora* spp., *Podosphaera* spp. including apple powdery mildew fungus (*P. leucotricha*), *Polymyxa graminis* Pseudomonas graminis), Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp., Pseudoperonospora spp. including P. cubensis and P. humuli, Pseudopeziza tracheiphila, P. hordei (P.Puccinia spp. (including P. hordei), P. recondita, P. striiformis, P. triticina), Pyrenopeziza spp., Pyrenophora spp., Pyricularia spp. (including P. oryzae, the rice blast fungus), Pythium spp. (including P. ultimum), Ramularia spp., Rhizoctonia spp., Rhizomucor pusillus, Rhizopus arizus This includes species of the genus Rhynchosporium (including *arrhizus*), *Rhynchosporium* spp., *Scedosporium* spp. (including *S. apiospermum* and *S. prolificans*), and *Schizothyrium pomi*. Species of the genera Sclerotinia, Sclerotium, Septoria (including S. nodorum and S. tritici), Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix, Stagonospora nodorum, Stemphylium, Stereum hirsutum, and Thanatephorus cucumeris. This includes species such as *Tilletia cucumeris*, *Tilletia basicola*, *Tilletia spp.*, *T. harzianum*, *T. pseudokoningii*, and *T. viride*, as well as species of the genus *Trichoderma*. Species belonging to the genera Trichophyton, Typhula, Uncinula necator, Urocystis, Ustilago, Venturia (including V. inaequalis), Verticillium, and Xanthomonas.

[0172] In particular, the compounds of formula (I) as defined in the present invention and the fungicidal and fungicidal compositions containing them can be used to control plant diseases caused by a wide range of fungal plant pathogens in the classes Basidiomycete, Ascomycete, Oomycete and / or Deuteromycete, Blasocladiomycete, Chrytidiomycete, Glomeromycete and / or Mucoromycete. More specifically, the compounds of formula (I) as defined in the present invention can be used to control Oomycetes.

[0173] These pathogens may include the following: Phytophthora diseases, such as those caused by Phytophthora capsici, Phytophthora infestans, Phytophthora sojae, Phytophthora fragariae, Phytophthora nicotianae, Phytophthora cinnamomi, Phytophthora citricola, Phytophthora citrophthora, and Phytophthora erythroseptica; and Pythium aphanidermatum and Pythium arenomanes. Pythium diseases, such as those caused by *Pythium arrhenomanes*, *Pythium graminicola*, *Pythium irregulare*, *Pythium sylvaticum*, and *Pythium ultimum*; *Peronospora destructor*, *Peronospora parasitica*, *Plasmopara viticola*, *Plasmopara halstedii*, *Pseudoperonospora cubensis*, *Albugo candida*, and *Sclerophthora macrospora*. Diseases caused by Peronosporales, such as macrospora and Bremia lactucae;Oomycetes include other species such as Aphanomyces cochlioides, Labyrinthula zosterae, Peronosclerospora sorghi, and Sclerospora graminicola. Bruises, spots, blast or canker and / or rot, for example, Stemphylium solani, Stagonospora tainanensis, Spirocaea oleaginea, Setosphaeria turcica, Pyrenochaeta lycoperisici, Pleospora herbarum, Phoma destructiva, Phaeosphaeria herpotrichoides, Phaeocryptocus gaeumannii, Ophiosphaerella graminicola (graminicola), Ophiobolus graminis, Leptosphaeria maculans, Hendersonia creberrima, Helminthosporium triticirepentis, (Setosphaeria turcica), Drechslera glycines, Didymella bryoniae, Cycloconium oleagineum, Corynespora cassiicola, Cochliobolus sativus, Bipolaris cactivora cactivora), Venturia inaequalis, Pyrenophora teres, 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 sojina, Cercospora zeae-maydis, Cercosporella capsellae, and Cercosporella herpotrichoides Capnodiales (including herpotrichoides), Cladosporium carpophilum, Cladosporium effusum, Passalora fulva, Cladosporium oxysporum, Dothistroma septosporum, Isariopsis clavispora, Mycosphaerella fijiensis, Mycosphaerella graminicola, Mycovellosiella koepkeii, Phaeoisariopsis bataticola (bataticola), Pseudocercosporella vitis, Pseudocercosporella herpotrichoides, Ramularia bataticolaMagnaporthales species such as beticola, Ramularia collo-cygni, Gaeumannomyces graminis, Magnaporthe grisea, Pyricularia oryzae, Anisogramma anomala, Apiognomonia errabunda, Cytospora platani, Diaporthe phaseolorum, Discula destructiva, Gnomonia fructicola, and Greeneria ubicola. Diaporthales species such as *Melanconium uvicola*, *Melanconium juglandinum*, *Phomopsis viticola*, *Sirococcus clavigignenti-juglandacearum*, *Tubakia dryina*, *Dicarpella spp.*, and *Valsa ceratosperma*, as well as Actinothyrium graminis, *Ascochyta pisi*, *Aspergillus flavus*, *Aspergillus fumigatus*, and *Aspergillus nidurans*. *Candida nidulans*, *Asperisporium caricae*, *Blumeriella jaapii*, *Candida spp.*, *Capnodium ramosum*, *Cephaloascus*(spp.), Cephalosporium gramineum, Ceratocystis paradoxa, Chaetomium spp., Hymenoscyphus pseudoalbidus, Coccidioides spp., Cylindrosporium padi, Diplocarpon malae, Others include Drepanopeziza campestris, Elsinoe ampelina, Epicoccum nigrum, Epidermophyton species, Eutypa lata, Geotrichum candidum, Gibellina cerealis, Gloeocercospora sorghi, Gloeodes pomigena, Gloeosporium perennans, and others; Gloeotinia temulenta, Griphospaeria colticola. corticola), Kabatiella lini, Leptographium microsporum, Leptosphaerulinia crassiasca, Lophodermium seditiosum, Marssonina graminicola, Microdochium nivale, Monilinia fructicola, Monographella albescens, Monosporascus cannonballus, Naemacyclus spp., Ophiostoma novo-urumi (novo-ulmi), Paracoccidioides brasiliensis, Penicillium expansum, Pestalotia rhododendri, Petriellidium speciesPezicula spp., Phialophora gregata, Phyllachora pomigena, Phymatotrichum omnivora, Physalospora abdita, Plectosporium tabacinum, Polyscytalum pustulans, Pseudopeziza medicaginis, Pyrenopeziza brassicae, Ramulispora sorghi, Rhabdocline (pseudotsugae), Rhynchosporium secalis, Sacrocladium oryzae, Scedosporium spp., Schizothyrium pomi, Sclerotinia sclerotiorum, Sclerotinia minor; Sclerotium spp., Typhula ishikariensis, Seimatosporium mariae, Lepteutypa cupressi, Septocyta ruborum, Sphaceloma persea (Perseae), Sporonema phacidioides, Stigmina palmivora, Tapesia yallundae, Taphrina bullata, Thielviopsis basicola, Trichoseptoria fructigenaPowdery mildew caused by plants such as *Zygophiala jamaicensis*, *Blumeria graminis*, *Erysiphe polygoni*, *Uncinula necator*, *Sphaerotheca fuligena*, *Podosphaera leucotricha*, *Podospaera macularis*, *Golovinomyces cichoracearum*, *Leveillula taurica*, *Microsphaera diffusa*, and *Oidiopsis gossipi*. Powdery mildews caused by Erysiphales, such as gossypii, Phyllactinia guttata, and Oidium arachidis; molds, such as Dothiorella aromatica, Diplodia seriata, Guignardia bidwellii, Botrytis cinerea, Botryotinia allii, Botryotinia fabae, Fusicoccum amygdali, Lasiodiplodia theobromae, and Macrophoma teicola theicola), Macrophomina phaseolina, Phyllosticta cucurbitacearumDiseases caused by Botryosphaeriales, such as cucurbitacearum; anthracnose, for example, caused by Glommerelales, such as Colletotrichum gloeosporioides, Colletotrichum lagenarium, Colletotrichum gossypii, Glomerella cingulata, and Colletotrichum graminicola; and wilt or canker, for example, Acremonium strictum, Claviceps purpurea, Fusarium culmorum, Fusarium graminealum *Fusarium graminearum*, *Fusarium virguliforme*, *Fusarium oxysporum*, *Fusarium subglutinans*, *Fusarium oxysporum f.sp.cubense*, *Gerlachia nivale*, *Gibberella fujikuroi*, *Gibberella zeae*, *Gliocladium spp.*, *Myrothecium verrucaria*, *Nectria ramulariae*, *Trichoderma viride*, *Trichothecium roseum* Ascomycetes, including those caused by the order Hypocleae, such as roseum and Verticillium theobromae. Basidiomycete, which includes the following: smut fungi such as those caused by the order Ustilaginales, such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, and Ustilago zeae; and Puccinia graninis, such as Cerotelium fici, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, and Puccinia graninis. Puccinia graminis), Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia striiformis f.sp. Hordei, Puccinia striiformis f.sp. cecalisPucciniales, such as Secalis, Pucciniastrum coryli, or Cronartium ribicola, Gymnosporangium juniperi-viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor, and Uromyces viciae-fabee. Caused by species of the order Uredinales, such as viciae-fabae; as well 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 Other rot and disease-causing diseases, such as those caused by *Tilletia moliniae* and *Tilletia caries*. Blastocladiomycetes, such as Physoderma maydis. Mucoromycete species, such as Choanephora cucurbitarum, Mucor spp., and Rhizopus arrhizus. Furthermore, diseases caused by other species and genera closely related to those listed above.

[0174] In addition to their fungicidal activity, compositions comprising the compounds defined in the present invention and the compound of formula (I) 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.

[0175] Within the scope of the present invention, target crops and / or useful plants to be protected are typically berry plants, e.g., blackberries, blueberries, cranberries, raspberries and strawberries; cereals, e.g., barley, corn, millet, oats, rice, rye, sorghum, rye and wheat; fiber plants, e.g., cotton, flax, hemp, jute and sisal; crops, e.g., sugar and fodder beets, coffee, hops, mustard, rapeseed (canola), poppies, sugarcane, sunflowers, tea and tobacco; fruit trees, e.g., apples, apricots, avocados, bananas, cherries, citrus fruits, nectarines, peaches, pears and plums; grasses, e.g., Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St. Augustine grass and zoysia grass Herbs, 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; and climbing plants, such as grapes and other perennial and annual crops.

[0176] Useful plants and / or target crops according to the present invention include conventional varieties such as insect-resistant (e.g., Bt. and VIP varieties), disease-resistant, herbicide-resistant (e.g., glyphosate- and glufosinate-resistant maize varieties, commercially available under trade names RoundupReady® and LibertyLink®), and nematode-resistant varieties, as well as genetically enhanced or genetically modified varieties. As an example, suitable genetically enhanced or genetically modified crop varieties include Stoneville 5599BR cotton and Stoneville 4892BR cotton varieties.

[0177] The terms “useful plants” and / or “target crops” should be understood to also include useful plants that have been given resistance to herbicides such as bromoxynil or certain classifications of herbicides (e.g., HPPD inhibitors, ALS inhibitors such as primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovir-sikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors, or PPO (protoporphyrinogen-oxidase) inhibitors) by conventional crossbreeding or genetic engineering methods. An example of a crop that has been given resistance to imidazolinones, such as imazamox, by conventional breeding (mutation) methods is Clearfield® summer rapeseed (canola). Examples of crops in which resistance to herbicides or certain classes of herbicides has been induced through genetic engineering include glyphosate- and glufosinate-resistant maize varieties marketed under trade names RoundupReady®, Herculex I®, and LibertyLink®.

[0178] The terms “useful plants” and / or “target crops” should be understood to include those that are naturally resistant to or conferred resistance to harmful insects. This includes plants transformed by the use of recombinant DNA technology, for example, to synthesize one or more selectively acting toxins, such as those known from toxin-producing bacteria. Examples of toxins that can be expressed include δ-endotoxin, vegetative insecticidal protein (Vip), insecticidal protein from nematode-symbiotic bacteria, and toxins produced by scorpions, arachnids, wasps, and fungi. An example of a crop modified to express Bacillus thuringiensis toxin is Bt maize KnockOut (Syngenta Seeds). An example of a crop containing two or more genes encoding insecticidal resistance and therefore expressing two or more toxins is VipCot® (Syngenta Seeds). Crops or their seed materials can also possess resistance to multiple types of pests (so-called superimposed transgenic events when genetically modified). For example, plants can be herbicide resistant and express insecticidal proteins at the same time, such as Herculex I® (Dow AgroSciences, Pioneer Hi-Bred International).

[0179] The terms “useful plants” and / or “target crops” should be understood to also include useful plants transformed using recombinant DNA technology to enable the synthesis of selectively acting antipathogenic substances, such as so-called “infection-specific 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 transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above.

[0180] Toxins that can be expressed by transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis such as δ-endotoxins like Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C; or vegetative insecticidal proteins (Vip) such as Vip1, Vip2, Vip3 or Vip3A; or species of the genus Photorhabdus, such as Photorhabdus luminescens or Xenorhabdus nematophilus, for example Photorhabdus spp. or Xenorhabdus Insecticidal proteins of nematode-symbiotic bacteria such as spp.; toxins produced by animals such as scorpion toxin, spider toxin, large wasp (wasp) toxin and other insect-specific neurotoxins; toxins produced by fungi such as Streptomycete toxin, plant lectins such as pea lectin, barley lectin or snowdrop lectin; aglutinin; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patain, cystatin, and papain inhibitors; lysine, Examples include ribosome-inactivating proteins (RIPs) such as corn-RIP, abrin, rufin, saporin, or briodin; steroid metabolic enzymes such as 3-hydroxysteroid xidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, and HMG-COA-reductase; ion channel blockers such as sodium or calcium blockers; juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase, and glucanase.

[0181] 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 plant insecticidal proteins (Vip), such as Vip1, Vip2, Vip3, or Vip3A, as well as explicitly hybrid toxins, cleavage toxins, and modified toxins. Hybrid toxins are produced by recombinant synthesis through novel combinations of different domains of these proteins (see, for example, International Publication No. 02 / 15701). Cleavage toxins, such as cleavage Cry1Ab, are known. In the case of modified toxins, one or more amino acids of a naturally occurring toxin are replaced. In such amino acid substitutions, preferably, a protease recognition sequence that does not naturally exist is inserted into the toxin, for example, in the case of Cry3A055, and a cathepsin-G recognition sequence is inserted into the Cry3A toxin (see International Publication No. 03 / 018810).

[0182] 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.

[0183] The preparation processes for such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparations are known, for example, from International Publication No. 95 / 34656, European Patent Application Publication No. 0367474, European Patent Application Publication No. 0401979, and International Publication No. 90 / 13651.

[0184] The toxins contained in transgenic plants confer resistance to harmful insects. Such insects can exist in any of the insect taxa, but are typically found in beetles (Coleoptera), diptera (Diptera), and butterflies (Lepidoptera).

[0185] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known, and some of them are commercially available. Examples of such plants include: YieldGard® (maize variety expressing Cry1Ab toxin); YieldGard Rootworm® (maize variety expressing Cry3Bb1 toxin); YieldGard Plus® (maize variety expressing Cry1Ab and Cry3Bb1 toxins); Starlink® (maize variety expressing Cry9C toxin); Herculex I® (maize variety expressing Cry1Fa2 toxin and the enzyme phosphinothrysin N-acetyltransferase (PAT) 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).

[0186] 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. 1507 Maize, registration number C / NL / 00 / 10, from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium. Genetically modified maize for the expression of the protein Cry1F to acquire resistance to certain Lepidoptera insects and the PAT protein to acquire resistance to the herbicide glufosinate ammonium. 7. NK603×MON810 Maize, registered under registration number C / GB / 02 / M3 / 03, is from Monsanto Europe, SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. It consists of a conventional hybrid maize variety created by crossing the genetically modified variety NK603 with MON 810. NK603×MON 810 Maize genetically modifies the protein CP4 EPSPS, obtained from the Agrobacterium sp. strain CP4, which confers resistance to the herbicide Roundup® (which contains glyphosate), and also genetically modifies the Cry1Ab toxin, obtained from Bacillus thuringiensis subsp. kurstaki, which provides resistance to certain Lepidoptera, including the European corn borer.

[0187] As used herein, the term “habitat” means cultivated land on which plants grow, or on which seeds of cultivated plants are sown, or on which seeds will be sown in the soil. It includes soil, seeds and seedlings, and established vegetation.

[0188] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves, and fruits.

[0189] The term "plant propagation material" is understood to refer to plant materials, such as seeds and other reproductive parts, as well as cuttings or tubers, that can be used for plant propagation, 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 full or partial treatment by immersion. Preferably, "plant propagation material" is understood to mean seeds. The pesticides referred to herein by their common names are known, for example, from "The Pesticide Manual," 19th Ed., British Crop Protection Council 2021.

[0190] The compounds of formula (I) as defined in this invention may be used in their original form or, preferably, in combination with auxiliaries conventionally used in the art of formulation. For this purpose, they may be appropriately incorporated in known forms into emulsifiable concentrates, coating pastes, ready-to-spray or dilutable solutions or suspensions, diluted emulsions, wettable powders, soluble powders, powders, granules, as well as encapsulations in polymeric substances. As with the type of composition, the method of application, such as spraying, misting, powdering, granulation, coating, or pouring, is selected according to the intended purpose and general circumstances. The composition may also include further auxiliaries such as stabilizers, defoamers, viscosity modifiers, binders, or tackifiers, and other formulations for obtaining fertilizers, sources of micronutrients, or special effects.

[0191] Suitable carriers and / or auxiliary materials, for example, carriers and auxiliary materials for agricultural use, may be solids or liquids and are substances useful in compounding 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.

[0192] A suspension concentrate is an aqueous formulation in which finely ground solid particles of an active compound are suspended. Such formulations contain anti-settling agents and dispersants, and may further contain wetting agents, defoaming agents, and crystal growth inhibitors to enhance activity. When used, these concentrates are diluted with water and typically applied as a spray to the area to be treated. The amount of the active ingredient may range from 0.5% to 95% of the concentrate.

[0193] 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.

[0194] Emulsifying concentrates are homogeneous liquid compositions that are dispersible in water or other liquids and may consist solely of an active compound and a liquid or solid emulsifier, or they may also contain liquid carriers such as xylene, high-boiling aromatic naphtha, isophorone, and other non-volatile organic solvents. When used, these concentrates are dispersed in water or other liquids and are typically applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.

[0195] Granular formulations include both extruded materials and relatively coarse particles and are typically applied undiluted to the area requiring treatment. Typical carriers for granular formulations include sand, fuller's soil, attapulgite clay, bentonite clay, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, gypsum, wood flour, crushed corn cobs, crushed peanut shells, sugars, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate, and other organic or inorganic materials that can absorb or be coated with the active compound. Granular formulations typically contain 5% to 25% active ingredients, which may include surfactants such as heavy aromatic naphtha, kerosene and other petroleum fractions, or vegetable oils; and / or stickers such as dextrin, glue or synthetic resins.

[0196] The powder is a fluid mixture of the active ingredient and finely ground solids such as talc, clay, powder, and other organic and inorganic solids that act as a dispersant and carrier.

[0197] 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.

[0198] 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.

[0199] Suitable agricultural additives and / or carriers useful for formulating the compositions of the present invention in the above-mentioned formulation types are well known to those skilled in the art.

[0200] Examples of usable liquid carriers include water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetate, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidinone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-Trichloroethane, 2-Heptanone, Alpha-pinene, d-Limonene, Ethylene glycol, Ethylene glycol butyl ether, Ethylene glycol methyl ether, γ-Butyrolactone, Glycerol, Glycerol diacetate, Glycerol monoacetate, Glycerol triacetate, Hexadecane, Hexylene glycol, Isoamyl acetate, Isobornyl acetate, Isooctane, Isophorone, Isopropylbenzene, Isopropyl myristate, Lactic acid, Laurylamine, Mesityl oxide, Methoxypropanol, Methyl isoamyl ketone, Methyl isobutyl ketone, Methyl laurate, Methyl octanoate, Methyl oleate, Methylene chloride, m-Xylene, n-Hexane, n-Octylamine, Octadeca Examples include sodium phosphate, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol and amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol and other high molecular weight alcohols, ethylene glycol, propylene glycol, glycerin and N-methyl-2-pyrrolidinone. Water is generally a preferred carrier for diluting concentrates.

[0201] Suitable solid carriers include, for example, talc, titanium dioxide, pyroferrite clay, silica, attapulgite clay, porous diatomaceous earth (kieselguhr), white pigment, diatomaceous earth, lime, calcium carbonate, bentonite clay, fuller's earth, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, and lignin.

[0202] 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.

[0203] 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.

[0204] 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 to the composition of the present invention. When applied simultaneously, these further active ingredients may be compounded 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.

[0205] 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 to 1.45 and Table A"): (7E,9Z)-dodeca-7,9-dien-1-yl acetate + TX, (9Z,11E)-tetradeca-9,11-dien-1-yl acetate + TX, (9Z,12E)-tetradeca-9,12-dien-1-yl acetate + TX, (E)-6-methylhepta-2-en-4-ol + TX, (E)-deca-5-en-1-ol acetate (E)-deca-5-en-1- Il + TX, (E)-trideca-4-en-1-yl acetate + TX, (E,Z)-tetradeca-4,10-dien-1-yl acetate + TX, (Z)-dodeca-7-en-1-yl acetate + TX, (Z)-hexadeca-11-en-1-yl acetate + TX, (Z)-hexadeca-11-enal + TX, (Z)-hexadeca-13-en-11-in-1-yl acetate + T X, (Z)-Ikos-13-en-10-one + TX, (Z)-Tetradeca-7-en-1-ar + 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 with 1,3-Dichloropropene + TX, 1,3-Dichloropropene + TX, 14-Methyloctadeca-1-ene + TX, 1-H-Pyridine-2-thione + TX, 2-(Octylthio)ethanol + TX, 2-chlorophenyl (CPMC) N-methylcarbamate + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 3,4-Dichlorotetrahydrothiophene 1,1-Dioxide + TX, 4-(Quinoxaline-2-ylamino)benzenesulfonamide + TX, 4-Methylnonan-5-ol with 4-Methylnonan-5-one + TX, 5-Methyl-6-thioxo-1,3,5-thiadiadinan-3-yl acetate + TX, 6-Isopentenylaminopurine + TX, 8-Hydroxyquinoline sulfate + TX, Abamectin + TX, Acequinosyl + TX, Acetamiprid + TX, Acetoprole + TX, Acrinatrin + TX, Acinonapyr + TX, Adoxophyes orana GV + TX, Afidopyropen + TX, Afoxolaner + TX, Agrobacterium radiobacter + TX, AKD-3088 + TX, Aranicarb + TX, Aldicarb + TX,Aldoxycarb + TX, Allethrin + TX, Alpha-cypermethrin + TX, Alphamethrin + TX, Alpha-multistriatin + TX, Amblyseius spp. + TX, Amidoflumet + TX, Amino Acids + TX, Aminocarb + TX, Anagrapha falcifera NPV + TX, Anagrus atomus + TX, Aphelinus abdominalis + TX, Aphidius colemani + TX, Aphidoletes aphidimyza + TX, Apholate + TX, Autographa californica NPV + TX, AZ 60541 + TX, Azadirachtin + TX, Azocyclotin + TX, Bacillus aizawai aizawai)+TX, Bacillus chitinosporus AQ746 (NRRL acceptance No. B-21 618)+TX, Bacillus firmus+TX, Bacillus kurstaki+TX, Bacillus mycoides AQ726 (NRRL acceptance No. B-21664)+TX, Bacillus pumilus (NRRL acceptance No. B-30087)+TX, Bacillus pumilus AQ717 (NRRL acceptance No. B-21662)+TX, a species of Bacillus (Bacillus sp.)AQ175 (ATCC acceptance No. 55608) + TX, Bacillus sp. AQ177 (ATCC acceptance No. 55609) + TX, Bacillus sp. AQ178 (ATCC acceptance No. 53522) + TX, Bacillus sphaericus Neide + TX, Bacillus subtilis AQ153 (ATCC acceptance No. 55614) + TX,Bacillus subtilis AQ30002 (NRRL acceptance No. B-50421) + TX, Bacillus subtilis AQ30004 (NRRL acceptance No. B-50455) + TX, Bacillus subtilis AQ713 (NRRL acceptance No. B-21661) + TX, Bacillus subtilis AQ743 (NRRL acceptance No. B-21665) + TX, Bacillus subtilis (unspecified) + TX, Bacillus thuringiensis AQ52 (NRRL acceptance No. B-21619) + TX, Bacillus thuringiensis (Bacillus Bacillus thuringiensis)BD#32 (NRRL Acceptance No. B-21530) +TX, Bacillus thuringiensis Berliner +TX, Bacillus thuringiensis 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 BMP 123+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, Bioarethrin + TX, Biorethmetrin + TX, Bis(tributyltin) oxide + TX, Bisagil + TX, Bistriflurone + TX, Bisulfurfen + TX, Brevicomin + TX, Broflanilide + TX, Broflusrinate + TX, Bromoacetamide + TX, Bromophos-ethyl + TX, Bronopol + TX, Busulfan + TX, Butocarboxyme + TX, Butopyronoxyl + TX, Butoxy(polypropylene glycol)+TX, Butylpyridabene+TX, Cadsaphos+TX, Calcium arsenate+TX, Carbaryl+TX, Carbofuran+TX, Carbon disulfide+TX, Carbosulfan+TX, Cartap+TX, CAS No.: 1594624-87-9+TX, CAS No.: 1922957-47-8+TX, CAS No.: 1255091-74-7+TX, CAS No.: 1365070-72-9+TX, CAS No.: 1445683-71-5+TX, CAS No.: 1445684-82-1+TX, CAS No.: 1594 626-19-3+TX, CAS number: 1594637-65-6+TX, CAS number: 1632218-00-8+TX, CAS number: 1808115-49-2+TX, CAS number: 1922957-46-7+TX, CAS number: 1922957-48-9+TX, CA S number: 1956329-03-5+TX, CAS number: 1990457-52-7+TX, CAS number: 1990457-55-0+TX, CAS number: 1990457-57-2+TX, CAS number: 1990457-66-3+TX, CAS number: 1990457-77 -6+TX, CAS number: 1990457-85-6+TX, CAS number: 2032403-97-5+TX, CAS number: 2044701-44-0+TX, CAS number: 2095470-94-1+TX, CAS number: 2128706-04-5+TX, CAS number: 21 28706-05-6+TX, CAS number: 2133042-31-4+TX, CAS number: 2133042-44-9+TX, CAS number: 2171099-09-3+TX, CAS number: 2220132-55-6+TX, CAS number: 2396747-83-2+TX,CAS number: 2408220-91-5+TX, CAS number: 2408220-94-8+TX, CAS number: 2415706-16-8+TX, Piperfuranilide (CAS number: 2615135-05-0)+TX, CAS number: 2719848-60-7+TX, CAS number: RNA (Colorado beetle (Leptinotarsa ​​decemlineata) specific recombinant double-stranded interfering GS2)+TX, Chlorantraniliprole+TX, Chlordane+TX, Chlorfenapyr+TX, Chloropicrin+TX, Chloroprallethrin+TX, Chlorpyrifos+TX, Chromafenozide+TX, Chrysoperla Carnea) + TX, Clenpyrin + TX, Chloetocarb + TX, Clothianidin + TX, Codrelia + TX, Codlememon + TX, Copper arsenite acetate + TX, Copper dioctanoate + TX, Copper hydroxide + TX, Copper sulfate + TX, Cresol + TX, Culfomate + TX, Cryptolaemus montrouzieri + TX, Curelua + TX, Cyanophenphos + TX, Cyantraniliprole + TX, Sibutrin + TX, Cyclaniliprole + TX, Cyclobtriflurum + TX, Cycloproslin + TX, Cycloxapride + TX, Codlinga (Cydia) Pomonella GV+TX, cyenopyrafen+TX, cyetopyrafen+TX, cyflumetofen+TX, cyfluthrin+TX, cyhalodimide+TX, sirohalothrin+TX, cypermethrin+TX, cyphenothrin+TX, cyprofuranilide+TX, cyromazine+TX, cytokinin+TX, Dacnusa sibirica sibirica)+TX, dazomet+TX, DBCP+TX, DCIP+TX, deltamethrin+TX, diafenthiuron+TX, dialiphos+TX, diamidaphos+TX, dibrom+TX, dibutyl adipate+TX, dibutyl phthalate+TX, dibutyl succinate+TX, diclofenthion+TX, diclofenthion+TX, diclofen+TX, dichlorophene+TX, dicliphos+TX, dichloromesothiaz+TX, diethyltoluamide+TX, diflubenzuron+TX, Diglyphus isaea+TX, Dimatif + TX, Dimethoate + TX, Dimethylcalvert + TX, Dimethyl phthalate + TX, Dimypropyridaz + TX, Dinactin + TX, Dinocap + TX, Dinotefuran + TX, Dioxabenzophos + TX, Dipirithione + TX, Dispala + TX, D-Limonene + TX, Dodeca-8-en-1-yl acetate + TX, Dodeca-9-en-1-yl acetate + TX, Dodeca-8,10-dien-1-yl acetate + TX, Dodicine + TX, Dominicalua + TX, Doramectin + TX, Emamectin + TX, Emamectin benzoate + TX, Empenthrin + TX, Encarsia Eretmoceras formosa) + TX, Endotar + TX, Endrin + TX, Eprinomectin + TX, Epsilon-momufluorothrin + TX, Epsilon-metofluthrin + TX, Eretmoceras eremicus Eremicus + TX, Esfenvalerate + TX, Ethion + TX, Ethiprole + TX, Etoprophos + TX, Ethyl 4-methyloctanoate + TX, Ethyl hexanediol + TX, Ethylene dibromide + TX, Etofenprox + TX, Ethoxazole + TX, Etopyrafen + TX, Eugenol + TX, Fermentation products derived from seaweed extract and molasses + TX, Fermentation products derived from seaweed extract and molasses containing urea + TX, Seaweed extract and plant fermentation products + TX, Seaweed extract and plant fermentation products containing plant hormones, vitamins, EDTA chelate copper, zinc, iron + TX, Famful + TX, Fenaminsulf + TX, Fenamiphos + TX, Fenazaquin + TX, Fenfluthrin + TX X, Fenitrothion + TX, Fenmezoditiaz + 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, Flomethoquine + TX, Flonicamide + TX, Fluacrypyrim + TX, Fluazindolidine + TX, Fluazuron + TX, Flubendiamide + TX, Flubendimine + TX, Fluchlordiniliprole + TX, Flucitrinate + TX, Flucycloxurone + TX, Flucitrinate + TX,Fluensulfone [318290-98-1] + TX, Fluensulfone + TX, Fluphenelim + TX, Flufenprox + TX, Flufiprole + TX, Fluhexaphon + TX, Flumethrin + TX, Fluopyram + TX, Flupyradiflon + TX, Flupyrimin + TX, Flupyroxystrobin + TX, Fluralaner + TX, Fluvalinate + TX, Flaxamethamide + TX, Formaldehyde + TX, Fostiazate + TX, Fostiethane + TX, Frontalin + TX, Furfural + T X, Gamma-Cyhalothrin + TX, Gossyplure (registered trademark) (1:1 mixture of (Z,E) and (Z,Z) isomers of hexadeca-7,11-dien-1-yl acetate) + TX, Grandrya + TX, Grandrya I + TX, Grandrya II + TX, Grandrya III + TX, Grandrya IV + TX, Granulovirus + TX, Guadipyr + TX, GY-81 + TX, Halfenprox + TX, Halofenozide + TX, Harbin + TX, Helicoverpa Heliothis punctigera (Nuclear Polyhedrosis Virus) + TX, Helicoverpa zea (Nuclear Polyhedrosis Virus) + TX, Helicoverpa zea (Nuclear Polyhedrosis Virus) + TX, Heliothis punctigera (Nuclear Polyhedrosis Virus) + TX, Heliothis virescens (Nuclear Polyhedrosis Virus) + TX, Hemel + TX, Hempa + TX, Heptafluthrin + TX, Heterophos + TX, Heterorhabditis bacteriophora and H. megidis + TX, Hexalurea + TX, Hexamide + TX, Hexithiazox + TX, Hypodamia convergence (Condens) + TX, Hydramethylnon + TX, Hydralgafen + TX, Calcium hydroxide + TX, Imisiaphos + TX, Imidacloprid + TX, Imiprothrin + TX, Indazapiroxamet + TX, Indoxacarb + TX, Iodomethane + TX, Iprodione + TX, Ipsdienol + TX, Ipsenol + TX, Isamidophos + TX, Isazophos + TX, Isocycloserum + 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-cyhalotrin + TX, Redoprona + TX, Lepimectin + TX, Leptomastix dactylopii + TX, Lineatin + TX, Littolua + TX, Lupulua + TX, Lotilaner + TX, Lufenuron + TX, Macrolophus caliginosus + TX, Mamestra brassicae) NPV+TX, mecarfone+TX, medolua+TX, megatomoic acid+TX, metaflumizone+TX, metaldehyde+TX, metam+TX, metam potassium+TX, metam sodium+TX, Metaphycus helvolus+TX, Metarhizium anisopliae var. acridum+TX, Metarhizium anisopliae var. anisopliae+TX, Metarhizium species spp.)+TX, Metepa+TX, Methiocarb+TX, Methiotepa+TX, Methomyl+TX, Methquin-butyl+TX, Methoxyphenozide+TX, Methylafolet+TX, Methylbromide+TX, Methyleugenol+TX, Methylisothiocyanate+TX, Methylneodecanamide+TX, Metofluthrin+TX, Metolcarb+TX, Mexacalbate+TX, Milbemectin+TX, Milbemycin oxime+TX, Momfluorothrin+TX, Morzide+TX, Moxidectin+TX, Mascaria+TX, Muscodor albus 620 (NRRL acceptance No. 30547)+TX, Muscodor roseus A3-5 (NRRL acceptance No. 30548)+TX, Myrothecium perlucaria Verrucaria composition + TX, Nabam + TX, NC-184 + TX, Neem tree-derived product + TX,Neodiprion sertifer NPV and N. lecontei NPV + TX, bis(dimethyldithiocarbamate) nickel + TX, niclosamide + TX, niclosamide-olamine + TX, nicoflurprole + TX, nitenpyram + TX, nithiazine + TX, nitrapyrine + TX, octadeca-2,13-dien-1-yl acetate + TX, octadeca-3,13-dien-1-yl acetate + TX, octylinone + TX, omethoate + TX, orflura + TX, Orius spp. + TX, orictalua + TX, ostramon + TX, oxamate + TX, oxamyl + TX, oxazosulfyl + TX, oxolinic acid + TX, oxytetracycline + TX, Paecilomyces fumosoroseus fumosoroseus)+TX, Paecilomyces lilacinus+TX, parathion-ethyl+TX, Pasteuria nishizawae+TX, Pasteuria penetrans+TX, Pasteuria ramosa+TX, Pasteuria thornei+TX, Pasteuria usgae+TX, p-cymene+TX, penfluron+TX, pentachlorophenol+TX, permethrin+TX, phenothrin+TX, phorate+TX, phosphamidone+TX, phosphocarb+TX, Chilean predatory mite (Phytoseiulus) persimilis)+TX, picaridin+TX, pioxaniliprole+TX, piperazine+TX, piperonyl butoxide+TX, pyrimicarb+TX, pyrimiphos-ethyl+TX, pyrimiphos-methyl+TX, diamondback moth (Plutella xylostella) granuloma virus+TX, diamondback moth (Plutella xylostella) nuclear polyhedrosis virus+TX, polyhedrosis virus+TX, potassium and molybdenum and EDTA chelate manganese+TX, potassium ethylxanthonate+TX, potassium hydroxyquinoline sulfate+TX, prallethrin+TX, probenazole+TX, profenofos+TX,Profluthrin + TX, Propalgit + TX, Propetamphos + TX, Propoxur + TX, Prothiophos + TX, Protrifenbute + TX, Piflubmid + TX, Pymetrozine + TX, Piraclophos + TX, Pirafluprole + 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, QRD 420 (terpenoid blend) + TX, QRD 452 (terpenoid blend) + TX, QRD 460 (terpenoid blend) + TX, Quillaja saponaria + TX, Quinoclamine + TX, Quinonamide + TX, Resmethrin + TX, Rhodococcus globulus globerulus)AQ719 (NRRL acceptance No. B-21663)+TX, sarolaner+TX, S-biorethrin+TX, cebuphos+TX, selamectin+TX, sigrua+TX, silafluofen+TX, simazine+TX, pentachlorophenoxide sodium+TX, sordidine+TX, spidoxamato+TX, spinetoram+TX, spinosad+TX, spirobudifen+TX, spirodiclofen+TX, spiromesifen+TX, spiropidione+TX, spirotetramato+TX, Spodoptera exigua polyhedrosis virus+TX, Spodoptera frugiperda nuclear polyhedrosis virus+TX, Steinernema viviones bibionis)+TX, Steinernema carpocapsae+TX, Steinernema feltiae+TX, Steinernema glaseri+TX, Steinernema riobrave+TX, Steinernema riobravis+TX, Steinernema scapterisci+TX, Steinernema spp.)+TX, Streptomyces galbus (NRRL acceptance No. 30232)+TX, a species of the genus Streptomyces sp.) (NRRL Acceptance No. B-30145) + TX, Streptomycin + TX, Streptomycin sesquisulfate + TX, Strychnine + TX, Sulcatol + TX, Sulfiflumin (CAS number: 2377084-09-6) + TX, Sulfoxaflor + TX, Tadimucarb + TX, Tebufenozide + TX, Tebufenpyrad + TX, Tebupirimiphos + TX, Tecrophthalam + TX, Tefluthrin + TX, Temephos + TX, Tepa + TX, 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, Tetranilipro Lu+TX, Theta-cypermethrin+TX, Thiacloprid+TX, Thiafenox+TX, Thiamethoxam+TX, Thiocyclam+TX, Thiodicarb+TX, Thiofanox+TX, Thiohempa+TX, Thimerosal+TX, Thiometon+TX, Thionadin+TX, Thiophanate+TX, Thiosultap+TX, Thiotepa+TX, Tigoraner+TX, Thiolantraniliprole+TX, Thioxazafen+TX, Tolfenpyrad+TX, Toxaphen+TX, Tralomethrin+TX, Transfluthrin+TX, Tretamine+TX, Triazamate+TX, Triazophos+TX, Triazurone+TX, Tributyltin oxide+TX, Trichlorfon+TX, Trichloronate+TX, Trichlorfon+TX, Trichogramma spp.)+TX, Triphenmorph+TX, Trifluenfronate+TX, Triflumezopyrim+TX, Trimedrua+TX, Trimedrua A+TX, Trimedrua B1+TX, Trimedrua B2+TX, Trimedrua C+TX, Trimetacarb+TX, Triphenyltin acetate+TX, Triphenyltin hydroxide+TX, Tranquol+TX, Cyclopyrazoflor+TX, Typhlodromus occidentalis+TX, Uredepa+TX, Verticillium lecanii+TX, Verticillium spp.+TX, Xylenols+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 (this (These compounds may be prepared by the method described in International Publication No. 2019 / 110427) + TX, (3',4',5'-trifluorobiphenyl-2-yl)-amide + TX, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone (These compounds may be prepared by the method described in International Publication No. 2017 / 220485) + TX, 2-amide No-6-methylpyridine-3-carboxylic acid (4-phenoxyphenyl)methyl (this compound can be prepared by the method described in International Publication No. 2014 / 006945) + TX, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate + TX, (9Z,11E)-tetradeca-9,11- Dien-1-yl + TX, (9Z,12E)-tetradeca-9,12-dien-1-yl acetate + TX, (E)-6-methylhept-2-en-4-ol + TX, (E)-deca-5-en-1-yl acetate with (E)-deca-5-en-1-ol + TX, (E)-trideca-4-en-1-yl acetate + TX, (E,Z)-tetradeca-4,10-dien-1-yl acetate + TX, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-Trimethylindan-4-yl]pyrazole-4-carboxamide + TX, (Z)-dodeca-7-en-1-yl acetate + TX, (Z)-hexadeca-11-en-1-yl acetate + TX, (Z)-hexadeca-11-enal + TX, (Z)-hexadeca-13-en-11-in-1-yl acetate + TX, (Z)-icos-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 from the method described in International Publication No. 2018 / 153707) + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazole-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide + TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazole-1-yl]acetyl]-4-piperidyl] Azole-4-yl]-4,5-dihydroisoxazole-5-yl]-3-chlorophenyl]methanesulfonate + TX, 1-(4,5-dimethylbenzimidazole-1-yl)-4,4,5-trifluoro-3,3-dimethylisoquinoline + TX, 1-(4,5-dimethylbenzimidazole-1-yl)-4,4-difluoro-3,3-dimethylisoquinoline + TX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridine-3-yl)-4,4,5-trifluoro-3,3-dimethylisoquinoline + TX, 1-( 6,7-dimethylpyrazolo[1,5-a]pyridine-3-yl)-4,4,6-trifluoro-3,3-dimethylisoquinoline + TX, 1-(6-chloro-7-methylpyrazolo[1,5-a]pyridine-3-yl)-4,4-difluoro-3,3-dimethylisoquinoline (these compounds can be prepared from 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 with 1,3-dichloropropene + TX, 1,3-dichloropropene + TX, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea + TX, 1-[2-[[1-(4-chlorophenyl)pyrazole-3-yl]oxymethyl]-3-methylphenyl]-4-methyltetrazole-5-one + TX, 10-dien-1-yl acetate + TX, 14-methyloctadeca-1-ene + TX, 1-bromo -2-chloroethane + TX, 1-dichloro-1-nitroethane + TX, 1-hydroxy-1H-pyridine-2-thione + TX, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea + TX, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazole-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl) Pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate + TX, 2-(2-butoxyethoxy)ethyl peronylate + TX, 2-(2-butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate + TX, 2-(4-chloro-3,5-xylyloxy)ethanol + TX, 2-(difluoromethyl) (Difluoromethyl)-N-(3-ethyl-1,1-dimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethylindan-4-yl]pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethylindan-4-yl]pyridine-3-carboxamide (This compound can be prepared from the method described in International Publication No. 2014 / 095675) + TX, 2-(difluoromethyl)-N-[3-ethyl-1,1-Dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, 2-(octylthio)ethanol + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate + TX, 2,2-dichlorovinyl 2-ethylsulfinylethylmethyl methyl phosphate + TX, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide + TX, 2,4-dichlorophenyl benzenesulfonic acid + TX, 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3 -c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetron (this compound can be prepared by the method described in International Publication No. 2011 / 138281) + TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol + TX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazole-1-yl)propan-2-ol (this compound can be prepared by the method described in International Publication No. 2017 / 029179) ) + TX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazole-1-yl)propan-2-ol (this compound can be prepared from the method described in International Publication No. 2017 / 029179) + TX, 2-chlorovinyldiethyl phosphate + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide + TX, 2-imidazolidone + TX, 2-isovalerylindan-1,3-dione + TX, 2-methyl(propa-2-inyl)aminophenyl methylcarbamate + TX, 2-oxo -N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide (this compound may be prepared by the method described in International Publication No. 2018 / 065414) + TX, 2-thiocyanatoethyl laurate + TX, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole (these compounds may be prepared by the method described in International Publication No. 2016 / 156085) + TX, 3-(4,4-difluoro-3,4-dihydro-3, 3-Dimethylisoquinoline-1-yl)quinolone + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide + TX, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carboninitrile (this compound can be prepared from the method described in International Publication No. 2016 / 156290) + TX, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carboninitrile (this compound can be prepared from the method described in International Publication No. 2016 / 156290) (Can be prepared by the method described in No. 56290) + TX, 3-bromo-1-chloropropa-1-ene + TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid + TX, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea + TX, dimethylcarbamine 3-methyl-1-phenylpyrazole-5-yl acid + 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-carbonitride + 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-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazole-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1, 2,4-triazole-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazole-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazine-3-one + TX, 4-chlorophenylphenylsulfate Hon + TX, 4-methyl(propa-2-inyl)amino-3,5-xylyl methylcarbamate + TX, 4-methylnonan-5-ol with 4-methylnonan-5-one + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohexa-2-enone + TX, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one + TX, 5,5-dimethyl-3- dimethylcarbamate Oxocyclohexa-1-enyl + TX, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, 5-methyl-6-thioxo-1,3,5-thiadiadinanan-3-yl acetate + TX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide (which may be prepared from the method described in International Publication No. 2020 / 109391) + TX, 6-Chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methylpyridazine-4-carboxamide (may be prepared from 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-difluoro-ethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide (may be prepared from the method described in International Publication No. 2020 / 109391) + T X, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazol-3-carbonitrile+TX, 6-isopentenylaminopurine+TX, 8-fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide+TX, 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide+TX, 8-hydroxyquinoline sulfate+TX, acetylone+TX, acetoprol+TX, acibenzolar+TX, acibenzolar-S-methyl+TX, acrylonitrile+TX, Adoxophyes Orana orana) GV+TX, Agrobacterium radiobacter+TX, Aldoxycarb+TX, Aldrin+TX, Allosamidin+TX, Alixicarb+TX, Alpha-chlorohydrin+TX, Alpha-ecdysone+TX, Alpha-multistriatin+TX, Aluminum phosphide+TX, Amblyseius spp.+TX, Amectotrazine+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, Anisifuruprin + TX, Anthraquinone + TX, Antu + TX, Aphelinus abdominalis + TX, Aphidius colemani + TX, Aphidoletes aphidimyza + TX, Afolet + TX, Aramite + TX, Arsenous acid + TX, Atidathion + TX, Autographa californica NPV + TX, Azaconazole + TX, Azamethiphos + TX, Azobenzene + TX, Azotoate + TX, Azoxystrobin + TX, Bacillus sphaericus Neide + TX, Bacillus thuringiensis (thuringiensis) Delta Endotoxin + TX, Barium Carbonate + TX, Barium Hexafluorosilicate + TX, Barium Polysulfide + TX, Valthrin + TX, Bayer 22 / 190 + TX, Bayer 22408 + TX, Beauveria brongniartii + TX, Benalaxyl + TX, Bencrotiaz + TX, Benomyl + TX, Benoxaphos + TX, Bentiavaricarb + TX, Benzothiostrobin + TX, Benzovindiflupir + TX, Benzyl Benzoate + TX, Beta-Cyfluthrin + TX, Beta-Cypermethrin + TX, Bethoxazine + TX, Bioetanomesrin + TX, Biopermethrin + TX, Bis(2-chloroethyl) ether + TX, Bis(tributyltin) oxide + TX, Bisadyl + TX, Bisthiosemi + TX X, Vitertanol + TX, Bixafen + TX, Blasticidin-S + TX, Borax + TX, Bordeaux mixture + TX, Boscalid + TX, Brevicomin + TX, Brodifacum + TX, Brofenvalerate + TX, Bromadiolon + TX, Bromesaline + TX, Bromfenbinphos + TX, Bromoacetamide + TX, Bromocyclene + TX, Bromo-DDT + TX, Bromophos + TX, Bromopropylate + TX, Bromuconazole + TX, Bronopol + TX, Bufencarb + TX, Bupirimate + TX,Buprofezin + TX, Busulfan + TX, N-[6-[[(Z)-[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate buta-3-inyl + TX, Butacarb + TX, Butathiophos + TX, Butocarboxim + TX, Butonate + TX, Butopyronoxyl + TX, Butoxy(polypropylene glycol) + TX, Butoxycarboxim + TX, Butylpyridaben + TX, Calcium arsenate + TX, Calcium cyanide + TX, Calcium polysulfide + TX, Canfechlor + TX, Captafor + TX, Captan + TX, Carbanolate + TX, Carbendazim + TX, Carbon disulfide + TX, Carbon tetrachloride + TX, Carbophenothion + TX, Carboxine + TX, Cartap hydrochloride + TX, CAS number: 2132414-04-9 + T X, CAS number: 2344721-61-3+TX, Sebazin+TX, Quinomethionate+TX, Chloralose+TX, Chlorbenside+TX, Chlorbicyclene+TX, Choldane+TX, Chlordecone+TX, Chlordimeform+TX, Chlordimeform hydrochloride+TX, Chlorphenetol+TX, Chlorfensone+TX, Chlorfensulfide+TX, Chlorobenzylate+TX, Chloroform+TX, Chloroinconazide+TX, Chloromebform+TX, Chloromethirone+TX, Chloroneb+TX, Chlorophacinone+TX, Chloropicrin+TX, Chloropropylate+TX, Chlorthalonil+TX, Chlorphoxime+TX, Chlorprazophos+TX, Chlorthiophos+TX, Clozolinate+TX, Cholecalciferol+TX, Chrysoperla carnea carnea)+TX, synerin I+TX, synerin II+TX, synerin derivatives+TX, cismethrin+TX, cis-resmethrin+TX, crocitrin+TX, closantel+TX, chodrel+TX, chodremon+TX, copper arsenate+TX, copper arsenate+TX, copper dioctanoate+TX, copper hydroxide+TX, copper naphthenate+TX, copper oleate+TX, copper oxide+TX, copper(I) oxychloride+TX, copper sulfate+TX, coumocrol+TX, coumafuryl+TX, coumphos+TX, coumtetralyl+TX, coumoxystrobin+TX, coumoxystrobin+TX,Cresol + TX, Crimidine + TX, Crotamiton + TX, Clothoxyphos + TX, Culfomate + TX, Cryolite + TX, Cryptolaemus montrouzieri + TX, CS 708 + TX, Querua + TX, Cufraneb + ​​TX, Cyanophenphos + TX, Cyanophos + TX, Cyanthioate + TX, Cyazofamide + TX, Sibutrin + TX, Cycloresrin + TX, Cyclobtriflame + TX, Cydia pomonella GV + TX, Cyflufenamid + TX, Simizole + TX, Cymoxanil + TX, Cyproconazole + TX, Cyprodinil + TX, Cythioate + TX, Cytokinins + TX, Dacnusa sibirica 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, diclobentiazox+TX, diclofenthion +TX, Diclofluanide +TX, Diclon +TX, Dichlorofen +TX, Dichlorvos +TX, Diclozoline +TX, Dicliphos +TX, Diclocimet +TX, Diclomezin +TX, Dichloran +TX, Diclesil +TX, Dicyclanil +TX, Dicyclopentadiene +TX, Dieldrin +TX, Dienochlore +TX, Dietofencarb +TX, Diethyl 5-methylpyrazole-3-yl phosphate +TX, Diethyltoluamide +TX, Diphenacum +TX, Difenoconazole +TX, Difethiaron +TX, Diflovidazine +TX, Diglyphus isae isaea)+TX, dirol+TX, dimatif+TX, dimeflusrin+TX, dimefox+TX, dimethane+TX, dimethilimol+TX, dimethomorph+TX, dimesrin+TX, dimethyl carbamate+TX, dimethyl phthalate+TX, dimethylvinphos+TX, dimethilane+TX,Dimoxystrobin + TX, Dynex + TX, Dynex-Dikrexin + TX, Diniconasol + TX, Dinocap-4 + TX, Dinocap-6 + TX, Dinoctone + TX, Dinopenton + TX, Dinoprop + TX, Dinosam + TX, Dinoseb + TX, Dinosulfone + TX, Dinotervon + TX, Geophenolan + TX, Dioxabenzophos + TX, Dioxathion + TX, Difacinone + TX, Diphenylsulfone + TX, Dipimethitron + TX, Dipirithione + TX, Disparluer+TX, Disulfiram+TX, Dithianone+TX, Diticlophos+TX, DNOC+TX, Dodeca-8-en-1-yl acetate+TX, Dodeca-9-en-1-yl acetate+TX, Dodeca-8+TX, Dodemorph+TX, Dodicin+TX, Dozin+TX, Dofenapine+TX, Dominicala+TX, Doramectin+TX, DSP+TX, d-Tetramesrin+TX, Ecdysterone+TX, Edifenphos+TX, EI 1642+TX, EMPC+TX, Encarsia formosa+TX, Endotal+TX, Endothione+TX, Enestrobin+TX, Enoxastrobin+TX, EPBP+TX, Epoxyconazole+TX, Eprinomectin+TX, Eretmocerus elemicus eremicus)+TX, ergocalciferol+TX, etaphos+TX, etaboxam+TX, ethiphencarb+TX, etylimol+TX, etoate-methyl+TX, 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoropropa-1-enoxy]phenyl]methyl]pyrazole-3-carboxylate ethyl (may be prepared from the method described in International Publication No. 2020 / 056090)+TX, 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate ethyl (may be prepared from the method described in International Publication No. 2020 / 056090)+TX, 1-[[4-[5-(trifluoromethyl)-1,2,4- Oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate ethyl + TX, 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate ethyl (this compound can be prepared from the method described in International Publication No. 2018 / 158365) + TX, 4-methyloctanoate ethyl + TX, ethyl formate + TX, ethyl hexanediol + TX, ethylene dibromide + TX, ethylene dichloride + TX, ethylene oxide + TX, etridiazole + TX, etrimphos + TX, eugenol + TX, EXD + TX, famoxadone + TX, farnesol + TX, farnesol with nerolidol + TX, phenamidone + TX,Phenamine Sulfo+TX, Phenamine Strobin+TX, Phenalimol+TX, Phenazaflor+TX, Fenbuconazole+TX, Fenbutatin Oxide+TX, Fenchlorphos+TX, Phenetacarb+TX, Fenflam+TX, Fenhexamide+TX, Fenitrothion+TX, Phenothicarb+TX, Phenoxacrim+TX, Phenoxanil+TX, Fenpiclonil+TX, Fenpicoxamide+TX, Fenpyrislin+TX, Fenpropidine+TX, Fenpropimorph+TX, Fenpyrad+TX, Fenpyrazamine+TX, Fenpyroximate+TX, Fenson+TX, Phensulfothion+TX, Fenthion+TX, Fenthion-ethyl+TX, Fentin+TX, Fentriphanil+TX, Ferbam+TX, Ferimzon+TX, Ferric Phosphate+TX, Furocumafen+TX, Flori Lupicoxamide + TX, Fluazinam + TX, Fluveneteram + TX, Flubendimine + TX, Flucoflon + TX, Flucycloxlon + TX, Fludioxonil + TX, Fluenetil + TX, Fluphenoxadiazam + TX, Fluphenoxystrobin + TX, Fluindapir + TX, Flumethylsulfolimu + TX, Flumorph + TX, Fluopicolide + TX, Fluopimomid + TX, Fluopyram + TX, Fluolbenside + TX, Fluoroacetamide + TX, Fluorimide + TX, Fluoxapiproline + TX, Fluoxastrobin + TX, Fluoxythioconazole + TX, Flupropazine + TX, Flupropazine hydrochloride + TX, Fluquinconazole + TX, Flusilazole + TX, Flusulfamide + TX, Fluthianil + TX, Flutranil + TX, Flutriafole + TX, Flaxapiroxad + TX, FMC 1137+TX, Holpet+TX, Formaldehyde+TX, Formethanate+TX, Formethanate Hydrochloride+TX, Formparanate+TX, Fosetyl-Aluminum+TX, Fosmethilane+TX, Phosspire+TX, Phosthiethane+TX, Frontalin+TX, Fuberidazole+TX, Flalaxil+TX, Flamethopir+TX, Flathiocarb+TX, Fretolin+TX, Furfural+TX, Gamma-HCH+TX, Gliodin+TX, Grandluer+TX, Grandluer I+TX, Grandluer 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+TX, Hexaconazole+TX, Hexadecyl Cyclopropanecarboxylate+TX, Hexaleluer+TX, Hexamide+TX, HHDN+TX, Hippodamia conbergensis (concentrates) + TX, hydragafen + TX, calcium hydroxide + TX, hydrogen cyanide + TX, himexazole + TX, hikincarb + TX, imanin + TX, imazalil + TX, imibenconazole + TX, iminoctadine + TX, impflufluxam + TX, ipconazole + TX, ipfentrifluconazole + TX, ipflufenoquin + 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, Japonyl+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, linden+TX, lineatin+TX, lilimphos+TX, liturua+TX, lulua+TX, rubenmixianan+TX, lithidathion+TX, Macrolophus caliginosus+TX, magnesium phosphide+TX, maronoben+TX,Mamestra brassicae NPV+TX, Mankapper+TX, Mancozeb+TX, Mandestrobin+TX, Mandipropamide+TX, Maneb+TX, Magidox+TX, M-Cumenyl Methylcarbamate+TX, Mecarbam+TX, Mecarbhon+TX, Medrua+TX, Mefentrifluconazole+TX, Megatomoic Acid+TX, Menazone+TX, Mepanipyrim+TX, Meparflusrin+TX, Mephosphoran+TX, Mepronil+TX, Mercuric Oxide+TX, Mercurous Chloride+TX, Mesulfen+TX, Mesulfenphos+TX, Metalaxyl+TX, Metam+TX, Metam-Potassium+TX, Metam-Sodium+TX, Metaphycus helvolus + TX, Metarhizium anisopliae var. acridum + TX, Metarhizium anisopliae var. anisopliae + TX, metharyl picoxamide + TX, metconazole + TX, metepa + TX, metacrinphos + TX, methanesulfonyl fluoride + TX, metasulfocarb + TX, methotepa + TX, metoclotophos + TX, methoprene + TX, metoquinone-butyl + TX, methotrin + TX, methoxychlor + TX, (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxypropane-2-methyl phenoxy + TX, (Z)-2-(5 -Cyclopentyl-2-methylphenoxy)-3-methoxypropa-2-enoate methyl (These compounds can be prepared from the methods described in International Publication No. 2020 / 193387) + TX, (Z)-2-[5-(3-isopropylpyrazole-1-yl)-2-methylphenoxy]-3-methoxypropa-2-enoate methyl + TX, (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazole-1-yl)phenoxy]propa-2-enoate methyl + T X, (Z)-3-methoxy-2-[2-methyl-5-(4-propyltriazole-2-yl)phenoxy]prop-2-enoate methyl + TX, (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazole-1-yl]phenoxy]prop-2-enoate methyl (These compounds may be prepared from the methods described in International Publication No. 2020 / 079111) + TX, (Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl) Methyl riazol-2-yl]phenoxy]propa-2-enoate + TX, methyl aphorate + TX, methyl bromide + TX, methyl eugenol + TX, methyl isothiocyanate + TX, N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazole-4-yl]-2-methyl-phenyl]methyl]carbamate (may be prepared from the method described in International Publication No. 2020 / 097012) + TX, N-[[4-[1-(4-cyclopropyl-2,6-Difluorophenyl)pyrazole-4-yl]-2-methylphenyl]methyl]carbamate methyl (may be prepared from the method described in International Publication No. 2020 / 097012) + TX, N-[[5-[4-(2,4-dimethylphenyl)triazole-2-yl]-2-methylphenyl]methyl]carbamate methyl + TX, methylchloroform + TX, methylene chloride + TX, methylneodecanamide + TX, methylam + TX, methylcarb + TX, metminostrobin + TX, methoxadiazone + TX, metraphenone + TX, methyltetraprole + TX, MGK 264+TX, Milbemycin oxime+TX, Mipahox+TX, Mirex+TX, Monoclotophos+TX, Morphothion+TX, Morzide+TX, Moxidectin+TX, Muscalua+TX, Mycrobutanil+TX, Microzoline+TX, Myrothecium werrucarya verrucaria) composition + TX, N-((1R)-1-benzyl-3-chloro-1-methyl-buta-3-enyl)-8-fluoro-quinoline-3-carboxamide (these compounds can be prepared from 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 from 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-phenoxy (C-phenyl)-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) + TX, N-[(1R)-1-benzyl-1,[3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide+TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide+TX, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide+TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quino Phosphorus-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethylbutyl]-8-fluoroquinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methylpropyl]-8-fluoroquinoline-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-(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-methylphenyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared from the method described in International Publication No. 2016 / 202742) + TX, N'-[4-(4,5-dichlorothiazole-2-yl)oxy-2,5-dimethylphenyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine (These compounds are prepared by the method described in International Publication No. 2015 / 155075) (Obtained) + 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 N'-[5- (These compounds can be prepared from the methods 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 from the methods 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(dimethyldithiocarbamate)nickel + TX, niclosamide-olamine + TX, nicotine + TX, nicotine sulfate + TX, niflulidide + TX, niccomycins + 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, norbolmid + TX, nualimol + TX, O,O,O',O'-tetrapropyldithiopyrophosphate + TX, octadeca-2,13-dien-1-yl acetate + TX, octadeca-3,13-Dien-1-yl + TX, Octylinone + TX, Oflas + TX, Oleic acid + TX, Omethoate + TX, Orfura + TX, Orius spp. + TX, Orictal + TX, Orysastrobin + TX, Ostramon + TX, Oxadixyl + TX, Oxamate + TX, Oxatiapiproline + TX, Oxin-copper + TX, Oxolinic acid + TX, Oxycarboxyne + TX, Oxideprophos + TX, Oxydisulfon + TX, Oxytetracycline + TX, Paclobutrazol + TX, Paecilomyces fumosoroseus + TX, Para-dichlorobenzene + TX, Parathion + TX, Parathion-methyl + TX, Pefurazoate + TX, Penconazole + TX, Pencyclon + TX, Penflufen + TX, Penflulon + TX, Pentachlorophenol + TX, Pentachlorophenyl laurate + TX, penthiopyrad + TX, permethrin + TX, PH 60-38 + TX, phenamacryl + TX, fencapton + TX, phosacetim + TX, phosalon + TX, phosdiphen + TX, phospholane + TX, phosglycine + TX, phosniclor + 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, piperonylbutoxide+TX, piprotal+TX, pyrimetaphos+TX, polychlorodicyclopentadiene isomer+TX, polychloroterpenes+TX, polynactins+TX, polyoxins+TX, potassium arsenite+TX, potassium ethylxanthogenicate+TX, potassium hydroxyquinoline sulfate+TX, potassium thiocyanate +TX, pp'-DDT+TX, Precosen I+TX, Precosen II+TX, Precosen III+TX, Primidophos+TX, Probenazole+TX, Prochloraz+TX, Proclonal+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, Pro Rothiofos + TX, Protoate + TX, Pidiflumetofen + TX, Pyraclostrobin + TX, Pyramethostrobin + TX, Pyraoxystrobin + TX, Pyrapropoin + TX, Pyraziflumid + TX, Pyrazofos + TX, Pyrethmesrin + TX, Pyrethrin I + TX, Pyrethrin II + TX, Pyrethrins + TX, Pyribencarb + TX, Pyridaclomethyl + TX, Pyridafenthion + TX, Pyridine-4-amine + TX, Pyriphenox + TX, Pyrimethanil + TX, Pirimitate + TX, Pirimorph + TX, Pyrinulone + TX, Pyriophenone + TX, Pyrisoxazole + TX, Pyrroquilon + TX, Quasia + TX, Quinalphos + TX, Quinalphos-methyl + TX, Quinoclamine + TX, Quinofumeline + TX, Quinonamide + TX, Quinothione + TX, Quinoxifen + TX, Quintozen + TX, R-1492 + TX, Lafoxanide + TX, Resmethrin + TX, Reynoutria sakhalinensisSachalinensis extract + TX, Ribavirin + TX, R-metalaxyl + TX, Rotenone + TX, Lianya + TX, Lianodine + TX, S421 + TX, Sabajira + TX, Shuradan + TX, Siriloside + TX, Seboctilamine + TX, Sebuphos + TX, Sedaxane + TX, Selamectin + TX, Sesamex + TX, Sesasmorin + TX, SI-0009 + TX, Sigluar + TX, Simazine + TX, Simeconazole + TX, Sub Sodium arsenate + TX, sodium cyanide + TX, sodium fluoride + TX, sodium fluoroacetate + TX, sodium hexafluorosilicate + TX, sodium pentachlorophenoxide + TX, sodium selenate + TX, sodium tetrathiocarbonate + TX, sodium thiocyanate + TX, sofamide + TX, sordidine + TX, spiroxamine + TX, SSI-121 + TX, Steinernema viviones bibionis)+TX, Steinernema carpocapsae+TX, Steinernema feltiae+TX, Steinernema glaseri+TX, Steinernema riobrave+TX, Steinernema riobravis+TX, Steinernema scapterisci+TX, Steinernema species(spp.) + TX, Streptomycin + TX, Streptomycin sesquisulfate + TX, Strychnine + TX, Sulcatol + TX, Sulcoflon + TX, Sulcoflon-sodium + TX, Sulfiram + TX, Sulfuramide + TX, Sulfotep + TX, Sulfoxide + TX, Sulfur + TX, Sulfuryl fluoride + TX, Sulprophos + TX, Tar oil + TX, Tau-fluvalinate + TX, Tadimucarb + TX, TDE + TX, Tebuconazole + TX, Tebufloxin + TX, Tebupyrimphos + TX, Tecrofta Lam+TX, Temephos+TX, Tepa+TX, TEPP+TX, Terarethrin+TX, Terbam+TX, N-[6-[[[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate tert-butyl+TX, Tetrachloroethane+TX, Tetrachlorothiophene+TX, Tetraconazole+TX, Tetradeca-11-en-1-yl acetate+TX, Tetradiphon+TX, Tetramethylfursulin+TX, Tetrasul+TX, Thallium sulfate+TX, Thiabendazoyl L+TX, Thiafenox+TX, Thiapronil+TX, Cyclophos+TX, Tifluzamide+TX, Thiocarboxyme+TX, Thiocyclam+TX, Thiocyclam Hydroxalate+TX, Thiadiazole 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+TX, Turingie Nsin + TX, Thiazinyl + TX, Tolchlorophos-methyl + TX, Tolprocarb + TX, Trilfluanide + TX, Tralomesrin + TX, Transpermesrin + TX, Tretamine + TX, Triadimefone + TX, Triadimenol + TX, Triamiphos + TX, Triatene + TX, Triazamate + TX, Triazophos + TX, Triazoxide + TX, Triazurone + TX, Tributyltin oxide + TX, Trichlormetaphos-3 + TX, Trichloronate + TX, Tricogramma speciesspp.)+TX, Triclopyricarb+TX, Tricyclazole+TX, Tridemorph+TX, Triphenmorph+TX, Triphenophos+TX, Trifloxystrobin+TX, Triflumizole+TX, Triforine+TX, Trimedluar+TX, Trimedluar A+TX, Trimedluar B1+TX, Trimedluar B2+TX, Trimedluar C+TX, Trimetacarb+TX, Trinactin+TX, Trinexapac+TX, Triphenyltin acetate+TX, Triphenyltin hydroxide+TX, Triplene+TX, Triticonazole+TX, Tranquol+TX, Typhlodromus occidentalis Occidentalis + TX, Uredepa + TX, Validamycin + TX, Valifenarate + TX, Bamidthion + TX, Vaniliprole + TX, Veratridine + TX, Veratrin + TX, Berbutin + TX, Verticillium lecanii + TX, Vinclozoline + TX, Warfarin + TX, XMC + TX, Xylenols + TX, Zeatin + TX, Zetamesrin + TX, Jonsemycin + TX, Zinc naphthenate + TX, Zinc phosphide + TX, Thiazole zinc + TX, Zineb + ​​TX, Ziram + TX, Zolaprofos + TX; Acinetobacter lwoffii + TX, Acremonium alternatum + TX, Acremonium cephalosporium + TX, Acremonium diospyri + TX, Acremonium obclavatum + TX, Adoxophyes orana granulovirus (AdoxGV) (Capex®) + TX, Agrobacterium radiobacter strain K84 (Galltrol-A®) + TX, Alternaria alternata + TX, Alternaria cassia + TX, Alternaria destoluene (Alternaria destruens)(Smolder(registered trademark))+TX, Ampelomyces quisqualis(AQ10(registered trademark))+TX, Aspergillus flavus AF36(AF36(registered trademark))+TX, Aspergillus flavus NRRL 21882(Aflaguard(registered trademark))+TX, Aspergillus spp.)+TX, Aureobasidium pullulans+TX, Azospirillum (MicroAZ®, TAZO B®)+TX, Azotobacter+TX, Azotobacter chroocuccum (Azotomeal®)+TX, Azotobacter cysts (Bionatural Blooming Blossoms®)+TX, Bacillus amyloliquefaciens+TX, Bacillus cereus+TX, Bacillus chitinosporus strain AQ746+TX, Bacillus chitinosporus (Bacillus Bacillus chitinosporus strain CM-1 + TX, Bacillus circulans + TX, Bacillus firmus (BioSafe®, BioNem-WP®), especially strain CNMC 1-1582 (e.g., VOTIVO® from BASF SE) + TX, Bacillus licheniformis strain 3086 (EcoGuard®, Green Releaf®) + TX, Bacillus licheniformis strain HB-2 (Biostart®, formerly Rhizoboost®) + TX, Bacillus macerans + TX, Bacillus marismortui + TX, Bacillus megatherium (Bacillus megaterium)+TX, Bacillus mycoides strain AQ726+TX, Bacillus papillae (Milky Spore Powder®)+TX, Bacillus pumilus spp.)+TX, Bacillus pumilus strain AQ717+TX, Bacillus pumilus strain GB34 (Yield Shield®)+TX, Bacillus pumilus strain QST 2808 (Sonata®, Ballad Plus®)+TX, Bacillus sphaericus (VectoLex®)+TX, Bacillus spp.+TX, Bacillus spp. strain AQ175+TX, Bacillus spp. strain AQ177+TX, Bacillus spp. strain AQ178+TX, Bacillus subtilis (Bacillus Bacillus subtilis strain AQ153+TX, Bacillus subtilis strain AQ743+TX, Bacillus subtilis strain QST 713 (CEASE®, Serenade®, Rhapsody®)+TX, Bacillus subtilis strain QST 714 (JAZZ®)+TX, Bacillus subtilis strain QST3002+TX, Bacillus subtilis strain QST3004+TX, Bacillus subtilis var. amyloriquefaciensamyloliquefaciens) strain FZB24 (Taegro®, Rhizopro®) + TX, Bacillus thuringiensis aizawai GC 91 (Agree®) + TX, Bacillus thuringiensis Cry 2Ae + TX, Bacillus thuringiensis Cry1Ab + TX, Bacillus thuringiensis israelensis (BMP123®, Aquabac®, VectoBac®) + TX, Bacillus thuringiensis krustaki (Bacillus thuringiensis Bacillus thuringiensis kurstaki (Javelin®, Deliver®, CryMax®, Bondide®, Scutella WP®, Turilav WP®, Astuto®, Dipel WP®, Biobit®, Foray®) + TX, Bacillus thuringiensis kurstaki BMP 123 (Baritone®) + TX, Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF / 3P®) + TX, Bacillus thuringiensis strain AQ52 + TX, Bacillus thuringiensis Bacillus thuringiensis) strain BD#32+TX, Bacillus thuringiensis tenebrionis (Novodor®, BtBooster)+TX, Bacillus thuringiensis var. aizawai (XenTari®, DiPel®)+TX, Bacteria spp.)(GROWMEND(registered trademark), GROWSWEET(registered trademark), Shootup(registered trademark))+TX, Clavipacter michiganensis bacteriophage (AgriPhage(registered trademark), Bakflor(registered trademark))+TX, Beauveria bassiana (Beaugenic(registered trademark), Brocaril WP(registered trademark))+TX, Beauveria bassiana GHA (Mycotrol ES(registered trademark), Mycotrol O(registered trademark), BotaniGuard(registered trademark))+TX, Beauveria brongniartii (Engerlingspilz(registered trademark), Schweizer Beauveria(registered trademark), Melocont(registered trademark))+TX, Beauveria spp.+TX, Botrytis cineria 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+TX, Candida famata+TX, Candida fructus+TX, Candida glabrata+TX, Candida guilliermondii+TX, Candida melibiosica+TX, Candida oleophila strain O+TX, Candida parapsilosis+TX, Candida pelliculosa+TX, Candida pulcherrima(Candida) Candida pulcherrima + TX, Candida reukaufii + TX, Candida saitoana (Bio-Coat®, Biocure®) + TX, . Candida sake + TX, Candida spp. + TX, Candida tenius + TX, Cedecea davisae + TX, Cellulomonas flavigena + TX, Chaetomium cochliodes (Nova-Cide®) + TX, Chaetomium globosum (Nova-Cide®) + TX, Chromobacterium subtsugae strain PRAA4-1T (Grandevo®) + TX, Cladosporium chlorocephalum chlorocephalum)+TX, Cladosporium cladosporioides+TX, Cladosporium oxysporum+TX, Cladosporium spp.+TX, Cladosporium tenuissimum+TX, Clonostachys rosea (EndoFine®)+TX, Colletotrichum acutatum+TX, Coniothyrium minitans (Cotans WG®)+TX, Coniothyrium spp.)+TX, Cryptococcus albidus (YIELDPLUS®)+TX, Cryptococcus humicola+TX, Cryptococcus infirmo-miniatus+TX, Cryptococcus laurentii+TX, Cryptophlebia leucotreta granulovirus (Cryptex®)+TX, Cupriavidus campinensis+TX, Cydia pomonella granulovirus (CYD-X®, Madex®, Madex® Plus, Madex Max, Carpovirusine®) + TX, Cylindrobasidium laeve (Stumpout®) + TX, Cylindrocladium + TX, Debaryomyces hansenii + TX, Drecslera hawaiinensis + TX, Enterobacter cloacae + TX, Enterobacteriaceae + TX, Entomophtora virulenta (Vektor®) + TX, Epicoccum nigrum + TX, Epicoccum purpurascens + TX, Epicoccum species spp.)+TX, Filobasidium floriforme+TX, Fusarium acuminatum+TX, Fusarium chlamydosporum+TX, Fusarium oxysporum (Fusaclean®, Biofox C®)+TX, Fusarium proliferatum+TX, Fusarium spp.+TX, Galactomyces geotrichum+TX, Gliocladium catenulatum (Primastop®, Prestop®)+TX, Gliocladium roseum roseum)+TX, Gliocladium spp. (SoilGard®)+TX, Gliocladium virens (Soilgard®)+TX, Granulovirus (Granupom®)+TX, Halobacillus halophilus+TX, Halobacillus litoralis+TX, Halobacillus trueperi+TX, Halomonas spp.)+TX, Halomonas subglaciescola+TX, Halovibrio variabilis+TX, Hanseniaspora uvarum+TX, Helicoverpa armigera nuclear polyhedron virus (Helicovex®)+TX, Helicoverpa zea nuclear nuclear polyhedron virus (Gemstar®)+TX, Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus strain, PFR-97®, PreFeRal®)+TX, Isoflavone formononetin formononetin)(Myconate(registered trademark))+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® of Koppert / Arysta))+TX, Lecanicillium longisporum (Vertiblast®)+TX, Lecanicillium muscarium (Vertikil®)+TX, Lymantria Dispar nuclear polyhedron disease virus (Disparvirus®)+TX, Marinococcus halophilus halophilus)+TX, Meira geulakonigii+TX, Metarhizium anisopliae (Destruxin WP(registered trademark))+TX, Metarhizium anisopliae (Met52(registered trademark))+TX, Metschnikowia fruticola (Shemer(registered trademark))+TX, Metschnikowia pulcherrima+TX, Microdochium dimerum (Antibot(registered trademark))+TX, Micromonospora coerulea+TX, Microsphaeropsis okracea ochracea)+TX, Muscodor albus 620 (Muscudor(registered trademark))+TX, Muscodor roseus, especially strain A3-5 (acceptance No. NRRL 30548)+TX, Mycorrhizae spp.)(AMykor(registered trademark), Root Maximizer(registered trademark))+TX, . Myrothecium verrucaria strain AARC-0255 (DiTera®, BROS PLUS®) + TX, Ophiostoma piliferum strain D97 (Sylvanex®) + TX, Paecilomyces farinosus + TX, Paecilomyces lilacinus strain 251 (MeloCon WG®) + TX, Paecilomyces linacinus (Biostat WP®) + TX, Paenibacillus polymyxa + TX, Pantoea agglomerans (BlightBan C9-1(registered trademark))+TX, Pantoea spp. +TX, Pasteuria nishizawae, especially strain Pn1 (CLARIVA of Syngenta / ChemChina)+TX, Pasteuria spp. (Econem(registered trademark))+TX, Penicillium aurantiogriseum+TX, Penicillium billai (Jumpstart(registered trademark), TagTeam(registered trademark))+TX, Penicillium brevicompactum+TX, Penicillium frequentans+TX, Penicillium griseofulum (Penicillium 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 corrugata + TX, Pseudomonas fluorescens (Zequanox®) + TX, Pseudomonas fluorescens strain A506 (BlightBan A506®) + TX, Pseudomonas putida (Pseudomonas putida)+TX, Pseudomonas reactans+TX, Pseudomonas spp.)+TX, Pseudomonas syringae (Bio-Save®)+TX, Pseudomonas viridiflava+TX, Pseudozyma flocculosa strain PF-A22 UL (Sporodex L®)+TX, Puccinia canaliculata+TX, Puccinia thlaspeos (Wood Warrior®)+TX, Pythium paroecandrum+TX, Pythium oligandrum (Polygandron®, Polyversum®)+TX, Pythium periprocum (Pythium periplocum)+TX, Rhanella aquatilis+TX, Rhanella spp.+TX, Rhizobia (Dormal®, Vault®)+TX, Rhizoctonia+TX, Rhodococcus globerulus strain AQ719+TX, Rhodosporidium diobovatum+TX, Rhodosporidium toruloides+TX, Rhodotorula glutinis+TX, Rhodotorula graminis+TX, Rhodotorula musiraginosa 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 uredinicola+TX, Serratia marcescens+TX, Serratia plymuthica+TX, Serratia spp.)+TX, Sordaria fimicola+TX, Spodoptera exigua nuclear polyhedron virus (Spod-X®, Spexit®)+TX, Spodoptera littoralis nuclear polyhedron virus (Littovir®)+TX, Sporobolomyces roseus+TX, Stenotrophomonas maltophilia+TX, Streptomyces albaduncus+TX, Streptomyces exfoliates+TX, Streptomyces galbus+TX, Streptomyces glyceoplanus (Streptomyces griseoplanus)+TX, Streptomyces griseoviridis (Mycostop®)+TX, Streptomyces hygroscopicus+TX, Streptomyces lydicus (Actinovate®)+TX, Streptomyces lydicus WYEC-108 (ActinoGrow®)+TX, Streptomyces violaceus+TX, Tilletiopsis minor+TX, Tilletiopsis spp.)+TX, Trichoderma asperellum (T34 Biocontrol®)+TX, Trichoderma atroviride (Plantmate®)+TX, Trichoderma gamsii (Tenet®)+TX, Trichoderma hamatum TH 382+TX, Trichoderma harzianum rifai (Mycostar®)+TX, Trichoderma harzianum T-22 (Trianum-P®, PlantShield HC®, RootShield®, Trichoderma-G®)+TX, Trichoderma harzianum T-39 (Trichoderma *Trichoderma harzianum T-39* (Trichodex®) + TX, *Trichoderma inhamatum* + TX, *Trichoderma koningii* + TX, *Trichoderma lignorum* + TX, *Trichoderma longibrachiatum* + TX, . Trichoderma polysporum (Binab T®) + TX, Trichoderma spp. LC 52 (Sentinel®) + TX, Trichoderma taxi + TX, Trichoderma virens (formerly Gliocladium virens GL-21) (SoilGuard®) + TX, Trichoderma virens + TX, Trichoderma viride + TX, Trichoderma viride strain ICC 080 (Remedier®) + TX, Trichosporon pullulans + TX, Trichosporon species (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 supplemental micronutrients (Natural II®)+TX, various fungi (Millennium Microbes®)+TX, Verticillium chlamydosporium chlamydosporium)+TX, Vip3Aa20(VIPtera(registered trademark))+TX, Virgibaclillus marismortui+TX, Xanthomonas campestris pv. poaePoae) (Camperico(registered trademark))+TX, Xenorhabdfus bovienii+TX, Xenorhabdus nematophilus+TX;. AGNIQUE® MMF+TX, Azadirachtin (Plasma Neem Oil®, AzaGuard®, MeemAzal®, Molt-X®, e.g., AZATIN XL from Certis, US)+TX, Botanical IGR (Neemazad®, Neemix®)+TX, BugOil®+TX, Canola Oil (Lilly Miller Vegol®)+TX, Chenopodium ambrosioides near ambrosioides) (Requiem®) + TX, Chrysanthemum extract (Crisant®) + TX, Lamiaceae essential oil (Botania®) + TX, Neem oil extract (Trilogy®) + TX, Clove, rosemary, peppermint and thyme oil extract (Garden insect killer®) + TX, Garlic + TX, Glycine betaine (Greenstim®) + TX, Kaolin (Screen®) + TX, Lemongrass oil (GreenMatch®) + TX, Melaleuca alternifolia extract (also known as tea tree oil) (Timorex Gold®) + TX, Clove, peppermint, garlic oil and mint mixture (Soil Shot®) + TX, Clove, rosemary and peppermint extract mixture (EF 400 (registered trademark)) + TX, a mixture of rosemary, sesame, peppermint, thyme and cinnamon extracts (EF 300 (registered trademark)) + TX, neem oil + TX, catnip oil (Nepeta cataria) + TX, Nepeta catarina + TX, nicotine + TX, oregano oil (MossBuster (registered trademark)) + TX, sesame oil (Nematon (registered trademark)) + TX, pine oil (Retenol (registered trademark)) + TX, pyrethrum + TX, Quillaja saponaria (Quillaja saponaria)Saponaria (NemaQ®) + TX, Reynoutria sachalinensis (Regalia®, Sakalia®) + TX, Rotenone (Eco Roten®) + TX, Rutaceae plant extract (Soleo®) + TX, Soybean oil (Ortho ecosense®) + TX, Brown algae storage glucan (Laminarin®) + TX, Thyme oil + TX; (E,Z)-7,9-Dodecadiene-1-yl acetate + TX, (E,Z,Z)-3,8,11-Tetradecatrienylate + TX, (Z,Z,E)-7,11,13-Hexadecatrienal + TX, 2-Methyl-1-butanol + TX, Biolure® + TX, Blackheaded Fireworm Pheromone (3M Sprayable Blackheaded Fireworm Pheromone®) + TX, Calcium Acetate + TX, Check-Mate® + TX, Codling Moth Pheromone (Paramount dispenser-(CM) / Isomate C-Plus®) + TX, Entostat Powder (Exosex CM®) (Exosex extract from palm trees) + TX, Grape Berry Moth Pheromone (3M MEC-GBM Sprayable Pheromone(registered trademark))+TX, Lavandryl senecioate+TX, Leafroller pheromone (3M MEC-LR Sprayable Pheromone(registered trademark))+TX, Muscamone (Snip7 Fly Bait(registered trademark))+TX, Oriental Fruit Moth pheromone (3M oriental fruit moth sprayable pheromone(registered trademark))+TX, Peachtree Borer pheromone (Isomate-P(registered trademark))+TX, Scenturion(registered trademark)+TX, Starbar Premium Fly Bait(registered trademark))+TX, Tomato pinworm pheromone (3M Sprayable pheromone(registered trademark))+TX; Acerophagus papaya + TX, Adalia bipunctata (Adalia-System®) + TX, Adalia bipunctata (Adaline®) + TX, Adalia bipunctata (Aphidalia®) + TX, Ageniaspis citricola + TX, Ageniaspis fuscicollis + TX, Amblyseius andersoni (Anderline®, Andersoni-System®) + TX, Amblyseius californicus (Amblyline®, Spical®) + TX, Amblyseius cucumeris cucumeris) (Thripex®, Bugline cucumeris®) + TX, Amblyseius fallacis (Fallacis®) + TX, Amblyseius swirskii (Bugline swirskii®, Swirskii-Mite®) + TX, Amblyseius womersleyi (WomerMite®) + TX, Amitus hesperidum + TX, Anagrus atomus + TX, Anagyrus fusciventris + TX, Anagyrus kamali + TX, Anagyrus roecki (Anagyrus loecki)+TX, Anagyrus pseudococci (Citripar(registered trademark))+TX, Anicetus benefices+TX, Anisopteromalus calandraecalandrae)+TX, Anthocoris nemoralis (Anthocoris-System(registered trademark))+TX, Aphelinus abdominalis (Apheline(registered trademark), Aphiline(registered trademark))+TX, Aphelinus asychis+TX, Aphidius colemani (Aphipar(registered trademark))+TX, Aphidius ervi (Aphelinus-System(registered trademark))+TX, Aphidius ervi (Ervipar(registered trademark))+TX, Aphidius gifuensis+TX, Aphidius matricariae (Aphidius Aphidoletes aphidimyza (Aphidend®, Aphidoline®) +TX, Aphytis lingnanensis +TX, Aphytis melinus +TX, Aprostocetus hagenowii +TX, Atheta coriaria (Staphyline®) +TX, Bombus spp. +TX, Bombus terrestris (Beeline®, Tripol®) +TX, Bombus terrestris (Natupol Beehive (registered trademark) + TX, Cephalonomia stephanoderis + TX, Chilocorus nigritus + TX, Chrysoperla carnea (Chrysoline (registered trademark), Chrysopa (registered trademark)) + TX, Chrysoperla rufilabri (Chrysoperlarufilabris)+TX, Cirrospilus ingenuus+TX, Cirrospilus quadristriatus+TX, Citrostichus phyllocnistoides+TX, Closterocerus chamaeleon+TX, Closterocerus spp.+TX, Coccidoxenoides perminutus (Planopar®)+TX, Coccophagus cowperi+TX, Coccophagus lycimnia+TX, Cotesia flavipes+TX, Cotesia plutellae plutellae)+TX, Cryptolaemus montrouzieri (Cryptobug®, Cryptoline®)+TX, Cybocephalus nipponicus+TX, Dacnusa sibirica (Minusa®, DacDigline®, Minex®)+TX, Delphastus catalinae (Delphastus®)+TX, Delphastus pusillus+TX, Diachasmimorpha krausii+TX, Diachasmimorpha longicaudata longicaudata)+TX, Diaparsis jucunda+TX, Diaphorencyrtus aligarhensis+TX, Diglyphus isaeisaea) (Diminex(registered trademark), Miglyphus(registered trademark), Digline(registered trademark)) + TX, Diversinervus spp. + TX, Encarsia citrina + TX, Encarsia formosa (Encarsia max(registered trademark), Encarline(registered trademark), En-Strip(registered trademark)) + TX, Encarsia guadeloupae + TX, Encarsia haitiensis + TX, Episyrphus balteatus (Syrphidend(registered trademark)) + TX, Eretmoceris siphonini + TX, Eretmocerus californicus californicus)+TX, Eretmocerus eremicus (Enermix(registered trademark), Ercal(registered trademark), Eretline e(registered trademark), Bemimix(registered trademark))+TX, Eretmocerus hayati+TX, Eretmocerus mundus (Bemipar(registered trademark), Eretline m(registered trademark))+TX, Eretmocerus siphonini+TX, Exochomus quadripustulatus+TX, Feltiella acarisuga (Feltiline(registered trademark))+TX, Feltiella acarisuga (Spidend(registered trademark))+TX, Phopius alisanus arisanus) + TX, Fopius ceratitivorus + TX, Formononetin (Wirless Beehome®) + TX, Franklinothrips vespiformisvespiformis)(Vespop(registered trademark))+TX, Galendromus occidentalis+TX, Goniozus legneri+TX, Habrobracon hebetor+TX, Harmonia axyridis(HarmoBeetle(registered trademark))+TX, Heterorhabditis bacteriophora(NemaShield HB(registered trademark), Nemaseek(registered trademark), Terranem-Nam(registered trademark), Terranem(registered trademark), Larvanem(registered trademark), B-Green(registered trademark), NemAttack(registered trademark), Nematop(registered trademark))+TX, Heterorhabditis megidis(Nemasys H(registered trademark), BioNem H (registered trademark), Exhibitline hm (registered trademark), Larvanem-M(registered trademark))+TX, Heterorhabditis spp. (Lawn Patrol(registered trademark))+TX, Hippodamia convergens+TX, Hypoaspis aculeifer (Aculeifer-System(registered trademark), Entomite-A(registered trademark))+TX, Hypoaspis miles (Hypoline m(registered trademark), Entomite-M(registered trademark))+TX, Ibalia leucospoides+TX, Lecanoideus floccissimus+TX, Lemophagus errabundus+TX, Leptomastidea abnormis abnormis)+TX, Leptomastix dactylopii (Leptopar®)+TX, Leptomastix epona+TX, Lindorus lophanthae+TX, Lipolexis oregmae+TX, Lucilia caesar (Natufly®)+TX, Lysiphlebus testaceipes+TX, Macrolophus caliginosus (Mirical-N®, Macroline c®, Mirical®)+TX, Mesoseiulus longipes longipes)+TX, Metaphycus flavus+TX, Metaphycus lounsburyi+TX, Micromus angulatus (Milacewing(registered trademark))+TX, Microterys flavusflavus)+TX, Muscidifurax raptorellus and Spalangia cameroni (Biopar®)+TX, Neodryinus typhlocybae+TX, Neoseiulus californicus+TX, Neoseiulus cucumeris (THRYPEX®)+TX, Neoseiulus fallacis+TX, Nesideocoris tenuis (NesidioBug®, Nesibug®)+TX, Ophyra aenescens aenescens) (Biofly(registered trademark))+TX, Orius insidiosus (Thripor-I(registered trademark), Oriline i(registered trademark))+TX, Orius laevigatus (Thripor-L(registered trademark), Oriline l(registered trademark))+TX, Orius majusculus (Oriline m(registered trademark))+TX, Orius strigicollis (Thripor-S(registered trademark))+TX, Pauesia juniperorum+TX, Pediobius foveolatus+TX, Phasmarhabditis hermaphrodita hermaphrodita) (Nemaslug®) + TX, Phymastichus coffea + TX, Phytoseiulus macropilus + TX, Phytoseiulus persimilis (Spidex®, Phytoline p®) + TX, Podisus maclibentalis (Podisusmaculiventris) (Podisus(registered trademark))+TX, Pseudacteon curvatus+TX, Pseudacteon obtusus+TX, Pseudacteon tricuspis+TX, Pseudaphycus maculipennis+TX, Pseudleptomastix mexicana+TX, Psyllaephagus pilosus+TX, Psyttalia concolor (complex)+TX, Quadrastichus spp.+TX, Rhyzobius lophantae lophanthae)+TX, Rodolia cardinalis+TX, Rumina decollate+TX, Semielacher petiolatus+TX, Sitobion avenae (Ervibank®)+TX, Steinernema carpocapsae (Nematac C®, Millenium®, BioNem C®, NemAttack®, Nemastar®, Capsanem®)+TX, Steinernema feltiae (NemaShield®, Nemasys F®, BioNem F®, Steinernema-System®, NemAttack®, Nemaplus®, Exhibitline) sf(registered trademark), Scia-rid(registered trademark), Entonem(registered trademark))+TX, Steinernema kraussei (Nemasys L(registered trademark), BioNem L(registered trademark), Exhibitlinesrb(registered trademark))+TX, Steinernema riobrave (BioVector(registered trademark), BioVektor(registered trademark))+TX, Steinernema scapterisci (Nematac S(registered trademark))+TX, Steinernema spp.+TX, Steinernematid spp. (Guardian Nematodes(registered trademark))+TX, Stethorus punctillum (Stethorus(registered trademark))+TX, Tamarixia radiate+TX, Tetrastichus setifer+TX, Thripobius semiluteus+TX, Torymus sinensis *Trichogramma sinensis* + TX, *Trichogramma brassicae* (Tricholine b®) + TX, *Trichogramma brassicae* (Tricho-Strip®) + TX, *Trichogramma evanescens* + TX, *Trichogramma minutum* + TX, *Trichogramma ostriniae* + TX, *Trichogramma platneri* + TX, *Trichogramma pretiosum* + TX, *Xanthopimpla stemmator* + TX; Abscisic acid + TX, Aminomite® + TX, BioGain® + TX, bioSea® + TX, CAS number: 2643947-26-4 + TX, Chondrostereum purpureum (Chontrol Paste®) + TX, Colletotrichum gloeosporioides (Collego®) + TX, Copper octanoate (Cueva®) + TX, Delta Trap (Trapline d®) + TX, Erwinia amylovora (Harpin) (ProAct®) + 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-brasonolide+TX, iron phosphate (Lilly Miller Worry Free Ferramol Slug & Snail Bait(registered trademark))+TX, MCP hale trap (Trapline f(registered trademark))+TX, Microctonus hyperodae+TX, Mycoleptodiscus terrestris (Des-X(registered trademark))+TX, Nosema locustae (Semaspore Organic Grasshopper Control(registered trademark))+TX, pheromone trap (Thripline ams(registered trademark)) + TX, potassium bicarbonate (MilStop(registered trademark)) + TX, potassium iodide + potassium thiocyanate (Enzicur(registered trademark)) + TX, potassium salt of fatty acid (Sanova(registered trademark)) + TX, potassium silicate solution (Sil-Matrix(registered trademark)) + TX, spider venom + TX, sticky trap (Trapline YF(registered trademark)) + TX, RebellAmarillo(registered trademark)+TX, SuffOil-X(registered trademark)+TX, Trap(Takitrapline y+b(registered trademark))+TX; Bacillus mojavensis strain R3B (acceptance No. NCAIM(P)B001389) (International Publication No. 2013 / 034938) + TX from Certis USA LLC, Bacillus pumilus, in particular strain BU F-33, with NRRL acceptance No. 50185 (BASF's CARTISSA® registered trademark, EPA registration number 71840-19) + TX, Bacillus subtilis CX-9060 + TX from Certis USA LLC, Bacillus sp., in particular strain D747 (available as DOUBLE NICKEL® from Kumiai Chemical Industry Co., Ltd.), acceptance No. FERM BP-8234, U.S. Patent No. 7,094,592 + TX, Bacillus subtilis strain BU1814, (VELONDIS® PLUS, VELONDIS® FLEX and VELONDIS® EXTRA from BASF SE) + TX, Bacillus subtilis var. amyloliquefaciens strain FZB24, with acceptance no. DSM 10271 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA registration no. 70127-5)) + TX, Bacillus subtilis, in particular strain QST713 / AQ713 (with NRRL acceptance no. B-21661, described in U.S. Patent No. 6,060,051, Bayer Available as SERENADE® OPTI or SERENADE® ASO from CropScience LP, US + TX, Paenibacillus polymyxa, in particular strain AC-1 (e.g., TOPSEED® from Green Biotech Company Ltd.) + TX, a strain of Paenibacillus sp., acceptance No. NRRL B-50972 or acceptance No.Those with NRRL B-67129, International Publication No. 2016 / 154297+TX, Pantoea agglomerans, in particular strain E325 (Acceptance No. NRRL B-21856) (available as BLOOMTIME BIOLOGICAL® FD BIOPESTICIDE from Northwest Agri Products)+TX, Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena)+TX; Aureobasidium pullulans, in particular spores of strain DSM14940, spores of strain DSM14941, or mixtures of spores of strains DSM14940 and DSM14941 (e.g., BOTECTOR® and BLOSSOM PROTECT® from bio-ferm, CH) + TX; Pseudozyma aphidis (as disclosed in International Publication No. 2011 / 151819 by Yissum Research Development Company of the Hebrew University of Jerusalem) + TX; Saccharomyces cerevisiae from Lesaffre et Compagnie cerevisiae), particularly strains 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 strain MBI110) (NRRL acceptance No. B-50768, International Publication No. 2014 / 028521) (STARGUS® from Marrone Bio Innovations) + TX, Bacillus amyloliquefaciens strain FZB42, acceptance No. DSM 23117 (available as RHIZOVITAL® from ABiTEP, DE) + TX, Bacillus amyloliquefaciens, in particular strain D747 (available as Double Nickel® from Kumiai Chemical Industry Co., Ltd., with acceptance number FERM BP-8234, U.S. Patent No. 7,094,592) + TX, Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (QUARTZO® (WG) and PRESENCE® (WP) from FMC Corporation) + TX, Bacillus licheniformis, in particular strain SB3086, acceptance No.ATCC 55406, International Publication No. 2003 / 000051 (available as ECOGUARD® Biofungicide and GREEN RELEAF® by Novozymes) + TX, Bacillus methylotrophicus strain BAC-9912 (from the Chinese Academy of Sciences' Institute of Applied Ecology) + TX, Bacillus mycoides isolate, with acceptance No. B-30890 (available from Certis USA LLC as BMJ TGAI® or WG and LifeGard®) + TX, Bacillus pumilus, in particular strain GB34 (available as Yield Shield® by Bayer AG, DE) + TX, Bacillus pumilus, in particular strain QST2808 (Bayer Available as SONATA®, a registered trademark of CropScience LP, US, with acceptance number [number missing].Bacillus subtilis CX-9060 (NRRL B-30087, as described in U.S. Patent No. 6,245,551) +TX, Bacillus subtilis IAB / BS03 (AVIV (trademark) of STK Bio-Ag Technologies, PORTENTO (registered trademark) of Idai Nature) +TX, Bacillus subtilis KTSB strain (FOLIACTIVE (registered trademark) of Donaghys) +TX, Bacillus subtilis strain BU1814 (available from BASF SE as VELONDIS (registered trademark) PLUS, VELONDIS (registered trademark) FLEX and VELONDIS (registered trademark) EXTRA) +TX, Bacillus subtilis strain GB03 (Bayer (Available as Kodiak® from AG,DE) +TX, Bacillus subtilis strain MBI 600 (Available as SUBTILEX from BASF SE), with acceptance number NRRL B-50595, U.S. Patent No. 5,061,495 +TX, Bacillus subtilis strain Y1336 (Available as BIOBAC® WP from Bion-Tech, Taiwan, registered in Taiwan as a biological fungicide with registration numbers 4764, 5454, 5096 and 5277) +TX, Bacillus subtilis var. amyloliquefaciens strain FZB24, acceptance No. DSM Those containing 10271 (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 as a biological fungicide in Taiwan No.Paenibacillus epiphyticus (registered as 4764, 5454, 5096 and 5277) +TX, BASF SE's Paenibacillus epiphyticus (International Publication No. 2016 / 020371) +TX, BASF SE's Paenibacillus polymyxa ssp. plantarum (International Publication No. 2016 / 020371) +TX, a strain of Paenibacillus sp., having acceptance No. NRRL B-50972 or acceptance No. NRRL B-67129, International Publication No. 2016 / 154297 +TX, Pseudomonas chlororaphis strain AFS009, acceptance No. NRRL Those possessing B-50897, International Publication No. 2017 / 019448 (e.g., HOWLER® and ZIO® of AgBiome Innovations, US) + TX, Pseudomonas chlororaphis, in particular strain MA342 (e.g., CEDOMON®, CERALL®, and CEDRESS® of Bioagri and Koppert) + TX, Pseudomonas fluorescens strain A506 (e.g., BLIGHTBAN® A506 of NuFarm) + TX, Pseudomonas proradix (e.g., PRORADIX® of Sourcon Padena) + TX, Streptomyces glyceobilidis griseoviridis) strain K61 (also known as Streptomyces galbus strain K61) (Acceptance No. DSM 7206) (MYCOSTOP® of Verdera), PREFENCE® of BioWorks, cf.Crop Protection 2006, 25, 468-475) + TX; Streptomyces lydicus strain WYEC108 (also known as Streptomyces lydicus strain WYCD108US) (Novozymes' ACTINO-IRON® and ACTINOVATE® registered trademarks) + TX; Trichoderma atroviride strain T11 (IMI352941 / CECT20498) + TX, Ampelomyces quisqualis strain AQ10 (e.g., AQ 10® from IntrachemBio Italia) + TX with acceptance no. CNCM 1-807, Ampelomyces quisqualis, especially strain AQ 10 (e.g., AQ 10® from IntrachemBio Italia) + TX, Aspergillus flavus strain NRRL 21882 (product known as AFLA-GUARD® from Syngenta / ChemChina) + TX, Aureobasidium pullulans, especially strain DSM 14941 spores + TX, Aureobasidium pullulans, especially strain DSM14940 spores + TX, Aureobasidium pullulans, especially a mixture of spores of strains DSM14940 and DSM 14941 (e.g., Bio-ferm, CH's Botector®) + TX, Chaetomium cupreum (acceptance no. CABI 353812) (e.g., AgriLife's BIOKUPRUM®) + TX, Chaetomium globosum (available as Rivale's RIVADIOM®) + TX, Cladosporium cladospolioides Coniothyrium cladosporioides) strain H39, with acceptance no. CBS122244, U.S. Patent Application Publication No. 2010 / 0291039 (by Stichting Dienst Landbouwkundig Onderzoek) + TX, Coniothyrium minitans, in particular strain CON / M / 91-8 (acceptance no.DSM9660, for example, Contans® (registered trademark) from Bayer CropScience Biologics GmbH + TX, Cryptococcus flavescens strain 3C (NRRL Y-50378) + TX, Dactylaria candida, Dilophosphora alopecuri (available as TWIST FUNGUS®), Fusarium oxysporum strain Fo47 (available as FUSACLEAN® from Natural Plant Protection) + TX, Gliocladium catenulatum (synonym: Clonostachys rosea f. catenulata) Gliocladium roseum (also known as Clonostachys rosea f rosea), strain J1446 (e.g., Prestop® of Lallemand) + TX, Gliocladium roseum (also known as Clonostachys rosea f rosea), strain IK726 (Jensen DF, et al. Development of a biocontrol agent for plant disease control with special emphasis on the near commercial fungal antagonist Clonostachys rosea strain 'IK726', Australasian Plant Pathol. 2007, 36(2):95-101) + TX, Gliocladium roseum (also known as Clonostachys rosea f rosea), strain 321U from Adjuvants Plus, Xue AGStrain ACM941+TX, Metschnikowia fructicola, in particular strain NRRL Y-30752+TX, Microsphaeropsis ochracea, Penicillium steckii (DSM 27859, International Publication No. 2015 / 067800)+TX from BASF SE, and Trichoderma asperellum strain ICC with acceptance No. CABI CC IMI 392716, as disclosed in (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root tot complex of field pea+TX, Can Jour Plant Sci 2003+TX, 83(3):519-524), A mixture of Trichoderma harzianum (also known as ICC012), Trichoderma gamsii (formerly T. viride) strain ICC 080 (e.g., BIO-TAM® from Isagro USA, Inc. or BIODERMA® by Agrobiosol de Mexico, SA de CV) with acceptance no. IMI 392151 + TX, Penicillium vermiculatum + TX, Phlebiopsis gigantea strain VRA 1992 (ROTSTOP® C from Danstar Ferment) + TX, Pseudozyma flocculosa strain PF-A22 UL (Plant Products Co.), available as SPORODEX(registered trademark)L from CA) + TX, cell wall of Saccharomyces cerevisiae strain LAS117 (CEREVISANE(registered trademark) of Lesaffre, ROMEO(registered trademark) of BASF SE) + TX, Saccharomyces cerevisiae strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938, CNCM No. 1-3939 (International Publication No. 2010 / 086790) from Lesaffre et Compagnie, FR + TX, Saccharomyces cerevisiae, especially strain LASO2 (from Agro-Levures et Derives) + TX, Simplicillium lanosonibae lanosoniveum)+TX, strain T34 (e.g., T34 Biocontrol of Biocontrol Technologies SL,ES) or Isagro strain ICC 012+TX, strain WRL-076 (NRRL Y-30842), U.S. Patent No. 7,579,183+TX, Talaromyces flavus strain V117b+TX, Trichoderma asperelloides JM41R (Acceptance No. NRRL B-50759) (TRICHO PLUS® of BASF SE)+TX, Trichoderma asperellum, in particular strain SKT-1, Acceptance No.FERM P-16510-containing strains (e.g., ECO-HOPE® from Kumiai Chemical Industry) + TX, Trichoderma asperellum, particularly strain kd (e.g., T-Gro from Andermatt Biocontrol) + TX, Trichoderma atroviride strain 77B (T77 from Andermatt Biocontrol) + TX, Trichoderma atroviride strain ATCC 20476 (IMI 206040) + TX, Trichoderma atroviride strain LC52 (e.g., Tenet from Agrimm Technologies Limited) + TX, Trichoderma atroviride strain LU132 (e.g., from Agrimm Technologies Limited's Sentinel)+TX, Trichoderma atroviride strain NMI no.V08 / 002388+TX, Trichoderma atroviride strain NMI no.V08 / 002389+TX, Trichoderma atroviride strain NMI no.V08 / 002390+TX, Trichoderma atroviride strain no.V08 / 002387+TX, Trichoderma atroviride strain SKT-1 (FERM P-16510), etc. Japanese Patent Publication No. 11-253151 + TX, Trichoderma atroviride strain SKT-2 (FERM P-16511), Japanese Patent Publication No. 11-253151 + TX, Trichoderma atroviride strain SKT-3 (FERM P-17021), Japanese Patent Publication No. 11-253151 + TX, Trichoderma atroviride, in particular strain SC1 (Acceptance No. CBS 122089, International Publication No. 2009 / 116106 and U.S. Patent No. 8,431,120 (from Bi-PA)) + TX, Trichoderma atroviride strain CNCM 1-1237 (e.g., Esquive® WP from Agrauxine, FR) + TX, Trichoderma fertile (e.g., BASF product TrichoPlus) + TX, Trichoderma gamsii (formerly T. viride) + TX, Trichoderma gamsii (formerly T. viride) strain ICC 080 (IMI CC 392151 CABI) (available as BIODERMA® from AGROBIOSOL DE MEXICO, SADE CV) + TX, Trichoderma gamsii strain ICC080 (IMI CC 392151 CABI, e.g., AGROBIOSOL DE MEXICO + TX, SADE CV)BioDerma)+TX, Trichoderma harmatum+TX, Trichoderma harmatum+TX with acceptance number ATCC 28012, Trichoderma harzianum+TX, Trichoderma harzianum rifai T39 (e.g., Trichodex® from Makhteshim, US)+TX, Trichoderma harzianum strain Cepa SimbT5 (from Simbiose Agro)+TX, Trichoderma harzianum strain DB 103 (available as T-GRO® 7456 by Dagutat Biolab)+TX, Trichoderma harzianum Trichoderma harzianum strain ITEM 908 (e.g., Trianum-P from Koppert) + TX, Trichoderma harzianum strain T-22 (e.g., Trianum-P from Andermatt Biocontrol or Koppert) + TX, Trichoderma harzianum strain TH35 (e.g., Root-Pro by Mycontrol) + TX, Trichoderma polysporum strain IMI 206039 (e.g., BINAB Bio-Innovation AB + TX, Binab TF WP by Sweden) + TX, Acceptance No.Trichoderma stromaticum (e.g., Tricovab by CEPLAC+TX, Brazil) + TX, Trichoderma virens (also known as Gliocladium virens), particularly strain GL-21 (e.g., SoilGard by Certis, US) + TX, Trichoderma virens strain G-41X (acceptance no. ATCC 20906) (e.g., ROOTSHIELD® 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 strain TV1 (e.g., Trianum-P by Koppert)+TX, Ulocladium oudemansii strain U3 with receipt No. NM 99 / 06216 (e.g., BOTRY-ZEN® by Botry-Zen Ltd, New Zealand and BOTRYSTOP® from BioWorks, Inc.)+TX, Verticillium albo-atrum (formerly V. dahliae) strain WCS850 deposited with the Central Bureau for Fungi Cultures (e.g., DUTCH TRIG® by Tree Care Innovations)+TX, Verticillium chlamidosporium chlamydosporium)+TX;. A mixture of Azotobacter vinelandii and Clostridium pasteurianum (available 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 KALO, Inc.) + TX, Azospirillum lipoferum lipoferum) (e.g., VERTEX-IF(trademark) of TerraMax, Inc.) +TX, Azotobacter chroococcum, especially strain H23 +TX, Azotobacter vinelandii, especially strain ATCC 12837 +TX, Bacillus amyloliquefaciens BS27 (acceptance No.NRRL B-5015)+TX, Bacillus amyloliquefaciens, especially strain FZB42 (e.g., RHIZOVITAL® of ABiTEP, DE)+TX, Bacillus amyloliquefaciens, especially strain IN937a+TX, Bacillus amyloliquefaciens pm414 (LOLI-PEPTA® of Biofilm Crop Protection)+TX, Bacillus amyloliquefaciens SB3281 (ATCC#PTA-7542, International Publication No. 2017 / 205258)+TX, Bacillus amyloliquefaciens amyloliquefaciens)TJ1000 (available from Novozymes as QUIKROOTS®)+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 (ATCC 55675, e.g., MEPICHLOR® from Arysta 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., YIELD SHIELD® of Bayer Crop Science, DE)+TX, Bacillus pumilus, especially strain QST2808 (Acceptance No. NRRL No. B-30087)+TX, Bacillus siamensis, especially strain KCTC 13613T+TX, Bacillus subtilis, especially strain AQ30002 (Acceptance No. NRRL No. B-50421, described in U.S. Patent Application No. 13 / 330,576)+TX, Bacillus subtilis, especially strain AQ30004 (NRRL No. B-50455, as described in U.S. Patent Application No. 13 / 330,576) + TX, Bacillus subtilis, particularly strain MBI 600 (e.g., SUBTILEX® from BASF SE) + TX, Bacillus subtilis rm303 (RHIZOMAX® from Biofilm Crop Protection) + TX, Bacillus subtilis strain BU1814 (available from BASF SE as TEQUALIS®) + TX, Bacillus tequilensis, particularly strain NII-0943 + TX, Bacillus thuringiensis BT013A (NRRL), also known as Bacillus thuringiensis 4Q7 No. B-50924) + TX, Bradyrhizobium japonicum (e.g., Novozymes' OPTIMIZE®) + TX, Delftia acidovorans, especially strain RAY209 (e.g., Brett Young Seeds' BIOBOOST®) + TX, Lactobacillus sp.) (e.g., LACTOPLANT® from LactoPAFI) + TX, Mesorhizobium cicer (e.g., NODULATOR from BASF SE) + TX, Paenibacillus polymyxa, especially strain AC-1 (e.g., TOPSEED® from Green Biotech Company Ltd.) + TX, Pseudomonas aeruginosa, especially strain PN1 + TX, Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena) + TX, Rhizobium leguminosarium biovar viciae (e.g., NODULATOR from BASF SE) + TX, Rhizobium leguminosarium * Myrothecium verrucaria strain AARC-0255 (e.g., DiTera® from Valent Biosciences) + TX, Penicillium bilaii strain ATCC 22348 (e.g., JumpStart® from Acceleron BioAg) + TX, Penicillium bilaii strain ATCC ATCC20851 + TX, Purpureocillium lilacinum (formerly known as Paecilomyces lilacinus) strain 251 (AGAL 89 / 030550, e.g., BioAct from Bayer CropScience Biologics GmbH) + TX, Pythium oliligandrum Pythium oligandrum strain DV74 + TX, Pythium oligandrum strain M1 (ATCC 38472, e.g., Polyversum of Bioprepraty, CZ) + TX, Rhizopogon amylopogon (Myco-Sol of Agri-Enterprise, LLC, formerly Helena Chemical Company) + TX, Rhizopogon fulvigleba (Myco-Sol of Agri-Enterprise, LLC, formerly Helena Chemical Company) + TX, Talaromyces flavus strain V117b + TX, Trichoderma asperellum strain (Eco-T of Plant Health Products, ZA) + TX, Trichoderma asperellum Asperellum strain KD (e.g., Andermatt Biocontrol's T-Gro) + TX, Trichoderma atroviride, especially strain No.V08 / 002387+TX, Trichoderma atroviride strain CNCM 1-1237 (e.g., Esquive® WP of Agrauxine, FR)+TX, Trichoderma atroviride strain LC52 (also known as Trichoderma atroviride strain LU132, e.g., Sentinel of Agrimm Technologies Limited)+TX, Trichoderma atroviride strain no. NMI No. V08 / 002388+TX, Trichoderma atroviride strain no. NMI No. V08 / 002389+TX, Trichoderma atroviride strain no. NMI No.V08 / 002390+TX, Trichoderma atroviride strain SC1 (described in International Publication No. 2009 / 116106)+TX, Trichoderma harzianum strain 1295-22+TX, Trichoderma harzianum strain ITEM 908+TX, Trichoderma harzianum strain T-22 (e.g., Andermatt Biocontrol or Koppert's Trianum-P)+TX, Trichoderma harzianum strain TSTh20+TX, Trichoderma virens strain GI-3+TX, Trichoderma virens virens) strain GL-21 (e.g., SoilGard®, Certis, USA) + TX; Trichoderma viride strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161:125-137) + TX; Nauk.AR w Szczecinie 161:125-137)+TK, Verticillium albo-atrum (formerly V. dahliae) strain WCS850 (CBS 276.92, e.g., Dutch Trig of Tree Care Innovations)+TX;. Agrobacterium radiobacter strain K84 (Galltrol from AgBiochem Inc.), +TX; Bacillus amyloliquefaciens, in particular strain PTS-4838 (e.g., AVEO from Valent Biosciences, US), +TX; Bacillus mycoides, isolate J. (e.g., BmJ from Certis USA LLC), +TX; Bacillus sphaericus, in particular serotype H5a5b strain 2362 (strain ABTS-1743) (e.g., VECTOLEX® from Valent BioSciences, US), +TX; Bacillus thuringiensis israelensis strain BMP 144 (e.g., AQUABAC® from Becker Microbial Products IL), +TX, Bacillus thuringiensis subsp. aizawai strain GC-91 +TX, 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. islaerensis Bacillus thuringiensis subsp. (israelensis) (serotype H-14) strain AM65-52 (acceptance no. ATCC 1276) (e.g., VECTOBAC® from Valent BioSciences, US) + TX, Bacillus thuringiensis subsp.Bacillus thuringiensis subsp. kurstaki strain ABTS 351 + TX, Bacillus thuringiensis subsp. kurstaki strain BMP 123 (from Becker Microbial Products, IL, BARITONE from Bayer CropScience) + TX, Bacillus thuringiensis subsp. kurstaki strain EG 2348 (LEPINOX from Certis, US) + TX, Bacillus thuringiensis subsp. kurstaki strain EG 7841 (CRYMAX from Certis, US) + TX, Bacillus thuringiensis subsp. kurstaki strain HD-1 (for example, Valent BioSciences, US DIPEL® ES)+TX, Bacillus thuringiensis subsp. kurstaki strain PB 54+TX, Bacillus thuringiensis subsp. kurstaki strain SA 11 (JAVELIN, Certis, US)+TX, Bacillus thuringiensis subsp. kurstaki strain SA 12 (THURICIDE, Certis, US)+TX, Bacillus thuringiensis subsp. tenebrionis strain NB 176 (SD-5428, e.g., NOVODOR® FC, BioFa DE)+TX, Bacillus thuringiensis variety Colmeli (Bacillus Bacillus thuringiensis var. Colmeri (e.g., TIANBAOBTC at Changzhou Jianghai Chemical Factory) + TX, Bacillus thuringiensis var. japonensisBacillus thuringiensis var. kurstaki strain EVB-113-19 (e.g., BIOPROTEC® from AEF Global) +TX, Brevibacillus laterosporus +TX, Burkholderia spp., especially Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis strain MBI 305) (Acceptance No. NRRL B-50319, International Publication No. 2011 / 106491 and International Publication No. 2013 / 032693, e.g., MBI206 from Marrone Bio Innovations) TGAI and ZELTO (registered trademark) + TX, Chromobacterium subtsugae, especially strain PRAA4-1T (e.g., MBI-203, e.g., GRANDEVO (registered trademark) of Marrone Bio Innovations) + TX, Lecanicillium muscarium Ve6 (MYCOTAL of Koppert) + TX, Paenibacillus popilliae (formerly Bacillus popilliae, e.g., MILKY SPORE POWDER (trademark) or MILKY SPORE GRANULAR (trademark) of St. Gabriel Laboratories) + TX, Serratia entomophila (e.g., INVADE (registered trademark) of Wrightson Seeds) + TX, Serratia marcescens (Serratia marcescens), especially strain SRM (acceptance No.MTCC 8708)+TX, Trichoderma asperellum (TRICHODERMAX from Novozymes)+TX, Wolbachia pipientis ZAP strain (e.g., ZAP MALES® from MosquitoMate)+TX; Beauveria bassiana strain ATCC 74040 (e.g., NATURALIS® from Intrachem Bio Italia) + TX, Beauveria bassiana strain ATP02 (acceptance No. DSM 24665), Apopka 97 (PREFERAL from SePRO) + TX, Beauveria bassiana strain GHA (acceptance No. ATCC74250, e.g., BOTANIGUARD® ES and MYCONTROL-O® from Laverlam International Corporation) + TX, Metarhizium anisopliae 3213-1 (deposited under NRRL acceptance number 67074 disclosed in International Publication No. 2017 / 066094, Pioneer Hi-Bred) International) + TX, Metalhizium robertsii 15013-1 (deposited under NRRL acceptance number 67073) + TX, Metalhizium robertsii 23013-3 (deposited under NRRL acceptance number 67075) + TX, Paecilomyces lilacinus strain 251 (MELOCON, Certis, US) + TX; Cydia pomonella (codling moth) granuloma virus (GV) + TX, Helicoverpa armigera (cotton worm) nuclear polyhedrosis virus (NPV) + TX, Adoxophyes orana (apple tortrix moth) granuloma virus (GV) + TX, Spodoptera exigua (armyworm) mNPV + TX, Spodoptera frugiperda (sea armyworm) mNPV + 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 tinctorius + TX, Pseudomonas spp. + TX, Rhizobium spp., especially Rhizobium trifolii (trifolii)+TX, Rhizopogon spp.+TX, Scleroderma spp.+TX, Streptomyces spp.+TX, Suillus spp.+TX, Agrobacterium spp.+TX, Azorhizobium caulinodans+TX, Azospirillum spp.+TX, Azotobacter spp.+TX, Bradyrhizobium spp.+TX, Gigaspora monosporum+TX;Allium sativum (NEMGUARD from Eco-Spray, BRALIC from ADAMA) + TX, Armour-Zen + TX, Artemisia absinthium + TX, Biokeeper WP + TX, Brassicaceae extract, especially rapeseed 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,CA's Heads Up (quinoa saponin) + TX, Chitin + TX, Dryopteris filix-mas + TX, Equisetum arvense + TX, Fortune Aza + TX, Fungastop + TX, Melaleuca alternifolia extract (STK's TIMOREX GOLD) + TX, naturally occurring Blad polypeptide extracted from lupin seeds (FRACTURE (registered trademark) from FMC) + TX, naturally occurring Blad polypeptide extracted from lupin seeds (PROBLAD (registered trademark) from Certis EU) + TX, Pyrethrins + TX, Quassia amara + TX, Quercus + TX, Quillaja extract (BASF's QL AGRI 35) + TX, Marrone Bio's REGALIA MAXX+TX, Requiem (trademark) insecticide+TX, Reynoutria sachalinensis extract (REGALLIA)+TX, ryania / ryanodine+TX, Symphytum officinale+TX, Tanacetum vulgare+TX, thymol+TX, mixture of thymol and geraniol (Eden Research CEDROZ)+TX, thymol mixed with geraniol and eugenol (Eden Research MEVALONE)+TX, Triact 70+TX, TriCon+TX, Tropaeulum majus+TX, Urtica dioica+TX, veratrine+TX, Viscum album+TX; Mercuric oxide + TX, octylinone + TX, thiophanate-methyl + TX; MGK 264+TX, 2-(2-butoxyethoxy)ethyl piperonylate+TX, 2-isovalerylindan-1,3-dione+TX, 4-(quinoxaline-2-ylamino)benzenesulfonamide+TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohexa-2-enone+TX, acibenzolar+TX, acibenzolar-S-methyl+TX, alpha-bromadiolone+TX, alpha-chlorohydrin+TX, aluminum phosphide+TX, anthraquinone+TX, anthraquinone+TX, anttu+TX, arsenite+TX, barium carbonate+TX, Benoxacol + TX, Bisthiosemi + TX, Brodifacum + TX, Bromadiolon + TX, Bromesaline + TX, Calcium cyanide + TX, Chloralose + TX, Chlorophacinone + TX, Cholecalciferol + TX, Croquintoceto (including Croquintoceto-mexyl) + TX, Copper naphthenate + TX, Copper(I) chloride + TX, Coumaflyryl + TX, Coumatetralyl + TX, Crimidine + TX, Cyprosulfamide + TX, Diazinon + TX, Dichlormid + TX, Dicyclopentadiene + TX, Difenacum + TX, Difeti Aron+TX, Diphacinone+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, Isoxadifen (Containing isoxadiphen-ethyl) + TX, lindane + TX, magnesium phosphide + TX, MB-599 + TX, mefenypr (containing mefenypr-diethyl) + TX, metcamifen + TX, methiocarb + TX, methyl bromide + TX, nerolidol + TX, norbolmid + TX, petroleum products + TX, phosacetim + TX, phosphine + TX, phosphorus + TX, pindone + TX, piperonyl butoxide + TX, piprotal + TX, potassium arsenite + TX, probenazole + TX, propyl isomer + TX, pyridine-4-amine + TX, pyrinulone + TX,Reynoutria sachalinensis extract + TX, ribavirin + TX, S421 + TX, siriloside + TX, sesamex + TX, sesasmorin + TX, sodium arsenite + TX, sodium cyanide + TX, sodium fluoroacetate + TX, strychnine + TX, sulfoxide + TX, thallium sulfate + TX, thyram + TX, trimetacarb + TX, warfarin + TX, zinc naphthenate + TX, zinc phosphide + TX, ziram + TX.

[0206] 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 salicylates and the commercially available SAR inducer acibenzolar-S-methyl.

[0207] The compounds of formula (I) as defined in the present invention are typically used in the form of compositions and can be applied to a field or plant to be treated simultaneously with or in succession to further compounds. These further compounds may be, for example, fertilizers or micronutrient donors or other preparations that affect plant growth. They may also be selective or non-selective herbicides, as well as insecticides, fungicides, bactericidal agents, nematicides, molluscicides, or mixtures of these preparations, along with further carriers, surfactants, or application enhancers commonly used in the art of formulation, as needed.

[0208] 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 auxiliary agents.

[0209] Accordingly, the present invention provides a composition, preferably a fungicidal composition, comprising at least one compound of formula (I) as defined in the present invention, an agriculturally acceptable carrier, and optionally an auxiliary agent. The agriculturally acceptable carrier is, for example, a carrier suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, in addition to the compound of formula (I) as defined in the present invention, the composition may also contain at least one or more pesticide compounds, such as additional fungicidal active ingredients.

[0210] Further aspects of the present invention relate to a method for controlling or preventing ectoparasitism by plant pathogenic or putrefactive microorganisms or organisms, particularly fungi, that are potentially harmful to humans, of plants, for example, useful plants, for example, crop plants, their reproductive materials, for example, seeds, harvested crops, for example, harvested food crops, or non-biological materials, the method comprising applying a compound of formula (I) as defined in the present invention or any of the preferred individual compounds defined above as an active ingredient to any part of a plant, a part of a plant or its habitat, its reproductive material, or non-biological material.

[0211] 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.

[0212] Preferred methods for controlling or preventing ectoparasitism of crop plants by plant pathogenic microorganisms, particularly fungi, include the application of a pesticide composition containing a compound of formula (I) as defined in the present invention, or at least one of the said compounds, as a foliar treatment. The frequency and amount of application will depend on the risk of ectoparasitism by the corresponding pathogen or insect. However, compounds 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. Compounds of formula (I) as defined in any part of the present invention can also be applied to seeds (coating) by impregnating the seeds or tubers with a liquid formulation of the fungicide or by coating them with a solid formulation.

[0213] Compositions containing formulations, for example, a compound of formula (I) as defined in the present invention, and, if desired, 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.

[0214] Methods of application for this composition, i.e., spraying, atomizing, scattering, brushing, powdering, diffusion, or pouring (these should be selected according to the intended purpose in general situations), methods for controlling the above-mentioned types of pathogens, and the use of the composition for controlling the above-mentioned types of pathogens are also subjects of the present invention. 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.

[0215] When the combination of the present invention is used for seed treatment, it is generally sufficient to use a ratio of the compound of formula (I) of 0.001 to 50 g per kg of seed, preferably 0.01 to 10 g per kg of seed.

[0216] Preferably, a composition comprising a compound of formula (I) as defined in the present invention is administered either prophylactically (meaning before the onset of the disease) or therapeutically (meaning after the onset of the disease).

[0217] The compositions of the present invention may be any of the conventional forms, for example, two-component systems, dry seed treatment powder (DS), seed treatment emulsion (ES), seed treatment fluid concentrate (FS), seed treatment solution (LS), seed treatment water-dispersible powder (WS), seed treatment capsule suspension (CF), seed treatment gel (GF), emulsion concentrate (EC), suspension concentrate (SC), suspension emulsion (SE), capsule suspension (CS), water-dispersible granules (WG), emulsifying granules It can be employed in the form of granules (EG), water-in-oil (EO) emulsions, oil-in-water (EW) emulsions, microemulsions (ME), oil dispersions (OD), oil-miscible flowables (OF), oil-miscible liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), industrial concentrates (TK), dispersible concentrates (DC), wettable powders (WP), or any technically feasible formulation combined with agriculturally acceptable adjuvants.

[0218] Such compositions can be produced by conventional methods, for example, by mixing an active ingredient with a suitable formulation deactivator (diluent, solvent, filler, and optionally other formulation components such as surfactants, biocides, antifreezes, spreading agents, thickeners, and compounds that provide auxiliary effects). Conventional sustained-release formulations can also be used when sustained effectiveness over a long period is desired. In particular, formulations applied in spray form, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules, may contain surfactants, such as wetting agents and dispersants, and other compounds that provide auxiliary effects, such as formaldehyde, and condensation products of naphthalene sulfonates, alkylaryl sulfonates, lignin sulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0219] The seed coating formulation is applied to seeds in a manner known to the present invention, using the combination and diluent of the present invention, for example, in a preferred seed coating formulation form, such as an aqueous suspension or a dry powder form having good adhesion to seeds. Such seed coating formulations are known in the art. The seed coating formulation may contain a single active ingredient or a combination of active ingredients in encapsulated form, for example, as sustained-release capsules or microcapsules.

[0220] Generally, a formulation comprises 0.01 to 90% by weight of an active agent, 0 to 20% of an agrochemically acceptable surfactant, and 10 to 99.99% of a solid or liquid inert formulation and auxiliary agent, wherein the active agent consists of at least a compound of formula (I) as defined in this invention, together with components (B) and (C), and optionally other active agents such as particularly microbial agents or preservatives. The concentrated form of the composition generally contains about 2 to 80%, preferably about 5 to 70% by weight of the active agent. 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 active agent. Commercial products are preferably formulated as concentrates, but end users will typically use diluted formulations.

[0221] While it is preferable to incorporate commercially available products as concentrates, end users typically utilize diluted formulations. [Examples]

[0222] The following examples illustrate the present invention. Certain compounds of the present invention can be distinguished from known compounds by their greater potency at lower doses, which can be verified by those skilled in the art using the experimental procedures outlined in the examples.

[0223] Combination example

[0224] [Table 2]

[0225] By thoroughly mixing the active ingredient with an auxiliary agent and grinding the mixture thoroughly in a suitable mill, a wettable powder can be obtained that can be diluted with water to form a suspension of the desired concentration.

[0226] [Table 3]

[0227] 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.

[0228] emulsifiable concentrate Active ingredient [compound of formula (I)] 10% Octylphenol polyethylene glycol ether 3% (4-5 mol of ethylene oxide) Calcium dodecylbenzenesulfonate 3% Castor oil polyglycol ether (35 mol ethylene oxide) 4% Cyclohexanone 30% Xylene mixture 50%

[0229] Emulsions of any required dilution suitable for plant protection can be obtained from this concentrate by dilution with water.

[0230] [Table 4]

[0231] Ready-to-use powders are obtained by mixing the active ingredient with a carrier and grinding the mixture in a suitable mill. Such powders can also be used for drying and coating seeds.

[0232] Extruded granules Active ingredient [compound of formula (I)] 15% Sodium lignin sulfonate 2% Carboxymethylcellulose 1% Kaolin 82%

[0233] The active ingredient is mixed with an auxiliary agent and ground, and the mixture is moistened with water. The mixture is then extruded and subsequently dried in an airflow.

[0234] Coated granules Active ingredient [compound of formula (I)] 8% Polyethylene glycol (molecular weight 200) 3% Kaolin 89%

[0235] The finely ground active ingredient is uniformly coated onto kaolin moistened with polyethylene glycol in a mixer. A non-dusting coated granule is thus obtained.

[0236] Suspension concentrate Active ingredient [compound of formula (I)] 40% Propylene glycol 10% Nonylphenol polyethylene glycol ether (15 mol ethylene oxide) 6% Sodium lignin sulfonate 10% Carboxymethylcellulose 1% Silicone oil (in the form of an emulsion at 75% in water) 1% water 32%

[0237] The finely ground active ingredient is tightly mixed with an auxiliary agent to obtain a suspension concentrate. By diluting this with water, a suspension of the desired dilution can be obtained. Using such dilutions, not only growing plants but also plant propagation materials can be treated by spraying, pouring, or immersion to protect them from microbial ectoparasitism.

[0238] 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 an emulsion making up 75% of the water) 0.2% Water 45.3%

[0239] The finely ground active ingredient is tightly mixed with an auxiliary agent to obtain a suspension concentrate. By diluting this with water, a suspension of the desired dilution can be obtained. Using such dilutions, not only growing plants but also plant propagation materials can be treated by spraying, pouring, or immersion to protect them from microbial ectoparasitism.

[0240] 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 median capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension using an apparatus suitable for this purpose.

[0241] 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.

[0242] Method A: Equipment: Shimadzu LCMS 2020 mass spectrometer; Column: HALOC 182.7 μm, 3.0 mm × 30 mm; Mobile phase: MeCN (containing either 0.05% HCOOH or 0.05% TFA) - Water (containing either 0.05% HCOOH or 0.05% TFA); Gradient: 5% to 95% MeCN 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 and 254 nm PDA.

[0243] Method B: Spectra were recorded using a mass spectrometer from Agilent with multimode electrospray and APCI (single quadrupole mass spectrometer) (polarity: cations and anions), capillary: 4.00kV, corona current: 4.0μA, charging voltage: 2.00kV, nitrogen gas flow rate: 12.0L / min, nebulizer pressure: 40psi, mass range: 100~1000m / z), dry gas temperature: 250℃, vaporizer temperature: 200℃, and a Waters UPLC: quaternary pump, heated column compartment, and tunable wavelength detector. Column: X-Bridge BEH C18, 2.5μm (2.1*50mm), column temperature: ambient, wavelength (nm): 215nm, gradient: A=0.05% TFA in water, B=0.05% TFA in acetonitrile. Gradient: Time / %B: 0 / 5, 1 / 5, 5 / 70, 7 / 95, 8.5 / 95, 8.6 / 5, 10 / 5; Flow rate: 0.6 mL / min.

[0244] 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: cations and anions), capillary voltage: 0.8–3.00kV, cone voltage: 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 homogeneous concentration (0.2 min), followed by 10~100% B (1.0 min), 100% B homogeneous concentration (0.2 min), 100~10% B (0.05 min), 10% B homogeneous concentration (0.05 min).

[0245] Method D: Spectra were recorded using an ACQUITY mass spectrometer (SQD or SQDII single quadrupole mass spectrometer) from Waters Corporation equipped with an electrospray source (polarity: cation or anion, capillary: 3.0kV, cone voltage: 30V, extractor voltage: 3.00V, source temperature: 150°C, desolvation temperature: 400°C, cone gas flow rate: 60L / hour, desolvation gas flow rate: 700L / hour, mass range: 140~800Da), as well as an ACQUITY UPLC from Waters Corporation equipped with a solvent degasser, binary pump, heated column compartment, and diode array detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm, Temperature: 60°C, DAD wavelength range (nm): 210~400, Solvent gradient: A = Water / Methanol 9:1 + 0.1% Formic Acid, B = Acetonitrile + 0.1% Formic Acid, Gradient: 0~100% B over 2.5 minutes, Flow rate (mL / min) 0.75.

[0246] Table A below summarizes the compounds of formula (I): - Retention time (RT), [M+H] + LC-MS data such as, - Type of method, and / or - Melting point (mp).

[0247] [Table 5-1]

[0248] [Table 5-2]

[0249] [Table 5-3]

[0250] [Table 5-4]

[0251] [Table 5-5]

[0252] [Table 5-6]

[0253] [Table 5-7]

[0254] [Table 5-8]

[0255] [Table 5-9]

[0256] [Table 5-10]

[0257] [Table 5-11]

[0258] [Table 5-12]

[0259] Example 1: Preparation of N-[5-[6-[(4-fluoro-3-methoxyphenyl)-(methoxymethyl)carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate (Compound 1) [ka] Step A: Preparation of ethyl imidazo[1,2-a]pyrazine-6-carboxylate [ka] A suspension of ethyl 5-aminopyrazine-2-carboxylate (0.500 g, 2.90 mmol, 1.00 equivalent) in water (15 mL) was mixed with sodium acetate (0.480 g, 5.80 mmol, 2.00 equivalent), followed by the addition of chloroacetaldehyde (0.68 g, 0.55 mL, 1.50 equivalent). The reaction mixture was stirred at 40°C for 16 hours. The reaction mixture was quenched with saturated Na2CO3 solution, extracted with ethyl acetate, washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude residue was purified on a silica gel cartridge (cyclohexane / ethyl acetate) to obtain imidazo[1,2-a]pyrazine-6-carboxylate ethyl as a beige solid. LC-MS (Method A): Rt 0.48 min, m / z=192(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=1.39-1.59(m,3H),4.43-4.66(m,2H),7.75-7.87(m,1H),7.90-8.01(m,1H),8.96-9.07(m,1H),9.11-9.24(m,1H).

[0260] Step B: Preparation of N-(4-fluoro-3-methoxyphenyl)imidazo[1,2-a]pyrazine-6-carboxamide [ka] To a stirred solution of ethyl imidazo[1,2-a]pyrazine-6-carboxylate (1.00 g, 4.97 mmol, 1.00 equivalent) and 4-fluoro-3-methoxyaniline (1.05 g, 7.45 mmol, 1.50 equivalent) in dry toluene (25.0 mL), trimethylaluminum (6.21 mL, 12.4 mmol, 2.50 equivalent) in toluene was added. The resulting reaction mixture was stirred at 90°C for 2 hours under a nitrogen atmosphere. The reaction mixture was cooled to 0°C, quenched with aqueous Rochelle salt, and diluted with ethyl acetate. The reaction mixture was filtered through a Celite pad and washed with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude residue was purified on a silica gel cartridge (dichloromethane / ethyl acetate) to obtain N-(4-fluoro-3-methoxyphenyl)imidazo[1,2-a]pyrazine-6-carboxamide as a yellow solid. 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=3.85(s,3H),7.17-7.22(m,1H),7.55-7.59(m,1H),7.79-7.82(dd,J=2.4,8.0Hz,1H),7. 96(d,J=1.2Hz,1H),8.35(s,1H),9.16(dd,J=0.8,1.6Hz,1H),9.41(d,J=1.2Hz,1H),10.59(s,1H)

[0261] Step C: Preparation of N-(4-fluoro-3-methoxyphenyl)-N-(methoxymethyl)imidazo[1,2-a]pyrazine-6-carboxamide [ka] To an ice-cold solution of N-(4-fluoro-3-methoxyphenyl)imidazo[1,2-a]pyrazine-6-carboxamide (500 mg, 1.48 mmol, 1.00 equivalent) in THF (10.0 mL), potassium; 2-methylpropane-2-olate (250 mg, 2.23 mmol, 1.50 equivalent) and tetrabutylammonium bisulfate (151 mg, 0.445 mmol, 0.30 equivalent) were added, followed by the addition of chloro(methoxy)methane (179 mg, 2.23 mmol, 1.50 equivalent). The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was cooled to 0°C, quenched with water, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The crude residue was purified on a silica gel cartridge (dichloromethane / methanol) to obtain N-(4-fluoro-3-methoxyphenyl)-N-(methoxymethyl)imidazo[1,2-a]pyrazine-6-carboxamide as a yellow solid. 1 H-NMR(400MHz,CDCl3,ppm)δ=3.47(s,3H),3.84(s,3H),5.30(s,2H),6.68(brs,1H),6.90 -6.95(m,2H),7.74(s,1H),7.85(s,1H),8.68(s,1H),8.76(brs,1H)

[0262] Step D: Preparation of N-(4-fluoro-3-methoxyphenyl)-3-iodo-N-(methoxymethyl)imidazo[1,2-a]pyrazine-6-carboxamide [ka] To a solution of N-(4-fluoro-3-methoxyphenyl)-N-(methoxymethyl)imidazo[1,2-a]pyrazine-6-carboxamide (80.0 mg, 0.206 mmol, 1.00 equivalent) in DMF (3.00 mL), N-iodosuccinimide (60.2 mg, 0.268 mmol, 1.30 equivalent) was added. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The crude residue was purified on a silica gel cartridge (dichloromethane / methanol) to obtain N-(4-fluoro-3-methoxyphenyl)-3-iodo-N-(methoxymethyl)imidazo[1,2-a]pyrazine-6-carboxamide as a grayish-white solid. 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=3.37(s,3H),3.74(s,3H),5.23(s,2H),6.79(brs,1H),7.03-7.08(m,1 H),7.21-7.24(dd,J=2.8,8.0Hz,1H),8.01(s,1H),8.64(s,1H),8.76(brs,1H).

[0263] Step E: Preparation of N-[5-[6-[(4-fluoro-3-methoxyphenyl)-(methoxymethyl)carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate (compound 1) To a stirred solution of N-(4-fluoro-3-methoxyphenyl)-3-iodo-N-(methoxymethyl)imidazo[1,2-a]pyrazine-6-carboxamide (250 mg, 0.521 mmol, 1.00 equivalent) and N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate methyl (185 mg, 0.651 mmol, 1.25 equivalents) in 1,4-dioxane / water (3:1) (7.0 mL), cesium carbonate (339 mg, 1.04 mmol, 2.00 equivalents) was added, and the mixture was purged with an argon stream for 2 minutes. CataCXium® A Pd G3 (CAS 1651823-59-4) (19.0 mg, 0.0260 mmol, 0.05 equivalents) was added to the reaction mixture under an N2 atmosphere. The resulting mixture was irradiated in microwaves at 100°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, followed by brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified on reversed-phase combiflash (acetonitrile / water) to obtain N-[5-[6-[(4-fluoro-3-methoxyphenyl)-(methoxymethyl)carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate methyl as a grayish-white solid. LC-MS (Method F): Rt 0.15 min, m / z=481(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=3.34(s,3H),3.70(s,3H),3.73(s,3H),5.22(s,2H),6.80(brs,1H),7.05-7.09(t,J=19.2Hz,1H),7.20- 7.22(dd,J=2.4,8.0Hz,1H),8.04-8.12(m,3H),8.59(d,J=1.2Hz,1H),8.80(s,1H),8.90(brs,1H),10.54(s,1H).

[0264] Example 2: Preparation of N-[5-[6-[(4-chloro-3-methoxyphenyl)-(cyanomethyl)carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate (compound 3) [ka] Step A: Preparation of 2-(4-chloro-3-methoxy-anilino)acetonitrile [ka] To a solution of 4-chloro-3-methoxyaniline (1.50 g, 9.50 mmol, 1.00 equivalent) in acetonitrile (19 mL), 2-bromoacetonitrile (1.40 mL, 20.0 mmol, 2.05 equivalent), sodium iodide (0.710 g, 4.80 mmol, 0.50 equivalent), and potassium carbonate (1.60 g, 11.0 mmol, 1.20 equivalent) were added. The reaction mixture was stirred under reflux at room temperature for 16 hours, followed by 6 hours. The reaction mixture was filtered, diluted with 2 M NaOH, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The crude residue was purified on a silica gel cartridge (cyclohexane / ethyl acetate) to obtain 2-(4-chloro-3-methoxyanilino)acetonitrile as a brown oil. LC-MS (Method C): Rt 0.80 min, m / z=197 / 199(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=3.87-3.92(m,3H),3.96-4.05(m,1H),4.09-4.14(m,2H),6.23-6.31(m,2H),7.21-7.26(m,1H).

[0265] Step B: Preparation of 3-bromoimidazo[1,2-a]pyrazine-6-carboxylic acid (compound X-1) [ka] To a stirred solution of imidazo[1,2-a]pyrazine-6-carboxylic acid (50 mg, 0.30 mmol, 1.0 equivalent) in DMF (10 mL), N-bromosuccinimide (60 mg, 0.34 mmol, 1.1 equivalents) was added at room temperature and the mixture was stirred for 16 hours. The reaction mixture was quenched with a saturated aqueous solution of Na2S2O3, and the precipitate was collected by filtration. The filtrate was washed with water and dried overnight at 40°C under vacuum to obtain 3-bromoimidazo[1,2-a]pyrazine-6-carboxylic acid. LC-MS (B method): Rt 0.88 min, m / z=242 / 244 (M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=1.00(s,1H),1.02(s,1H),8.09(s,1H)

[0266] Step C: Preparation of 3-bromo-N-(4-chloro-3-methoxyphenyl)-N-(cyanomethyl)imidazo[1,2-a]pyrazine-6-carboxamide [ka] To a solution of 2-(4-chloro-3-methoxyanilino)acetonitrile (0.150 g, 0.763 mmol, 1.00 equivalent) in ethyl acetate (3.05 mL), 1-propanephosphonic anhydride (50% in ethyl acetate) (0.500 mL, 0.839 mmol, 1.10 equivalent), 3-bromoimidazo[1,2-a]pyrazine-6-carboxylic acid (compound X-1) (0.203 g, 0.839 mmol, 1.10 equivalent), and N-ethyl-N-isopropyl-propan-2-amine (0.522 mL, 3.05 mmol, 4.00 equivalent) were added. The reaction mixture was stirred at 85°C for 16 hours. The reaction mixture was quenched with water and diluted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The crude residue was purified on a silica gel cartridge (cyclohexane / ethyl acetate) to obtain 3-bromo-N-(4-chloro-3-methoxyphenyl)-N-(cyanomethyl)imidazo[1,2-a]pyrazine-6-carboxamide as a gum. LC-MS (Method C): Rt 0.87 min, m / z=420(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=3.90(s,3H),4.81(br s,2H),6.74(br d,J=7.63Hz,1H),6.92(d,J=2.18Hz,1H),7.31(br d,J=7.63Hz,1H),7.86(s,1H),8.56-8.73(m,1H),8.80(s,1H)

[0267] Step D: Preparation of N-[5-[6-[(4-chloro-3-methoxyphenyl)-(cyanomethyl)carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate (compound 3) A mixture of 3-bromo-N-(4-chloro-3-methoxyphenyl)-N-(cyanomethyl)imidazo[1,2-a]pyrazine-6-carboxamide (0.060 g, 0.14 mmol, 1.00 equivalent), N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate methyl (0.056 g, 0.20 mmol, 1.40 equivalent), and cesium carbonate (0.070 g, 0.21 mmol, 1.50 equivalent) in water (0.29 mL) and 2-methyltetrahydrofuran (1.60 mL) was flushed with argon for 5 minutes. Next, tetrakis(triphenylphosphine)palladium(0) (0.0085 g, 0.0071 mmol, 0.05 equivalents) was added, and the reaction mixture was heated at 100°C under microwave irradiation and stirred for 1 hour. 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 Na2SO4, filtered, and concentrated under reduced pressure. The crude residue was diluted in the minimum amount of dichloromethane, heated, cooled again, and diisopropyl ether was added. The beige solid was filtered and dried at 60°C under vacuum to obtain N-[5-[6-[(4-chloro-3-methoxyphenyl)-(cyanomethyl)carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate methyl as a beige solid. LC-MS (Method C): Rt 0.85 min, m / z=492(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=3.90(s,3H),3.90(s,3H),4.79(br s,2H),6.74(br d,J=7.63Hz,1H),6.92(d,J=2.18Hz,1H),7.33(br d,J=8.36Hz,1H),7.83-7.91(m,2H),7.94(s,1H),8.25(d,J=8.36Hz,1H),8.47(d,J=1.82Hz,1H),8.77(br s,1H),8.81(br s,1H).

[0268] Example 3: Preparation of N-[5-[6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate (compound 4) [ka] Step A: Preparation of 3-bromo-N-(4-fluoro-3-methoxyphenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide (compound X-2) [ka] To a solution of 4-fluoro-3-methoxy-N-methylaniline (0.134 mL, 0.930 mmol, 1.50 equivalents) in N,N-dimethylacetamide (3.75 mL), 1-propanephosphonic anhydride (50% in ethyl acetate) (0.922 mL, 1.55 mmol, 2.50 equivalents), 3-bromoimidazo[1,2-a]pyrazine-6-carboxylic acid (compound X-1) (0.203 g, 0.839 mmol, 1.00 equivalent), and N-ethyl-N-isopropyl-propan-2-amine (0.530 mL, 3.10 mmol, 5.00 equivalents) were added. The reaction mixture was stirred at 55°C for 35 minutes. The reaction mixture was quenched with a saturated solution of NaHCO3 and diluted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The crude residue was purified on a silica gel cartridge (cyclohexane / ethyl acetate) to obtain 3-bromo-N-(4-fluoro-3-methoxyphenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide as a yellow solid. LC-MS (Method C): Rt 0.79 min, m / z=379 / 381(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=3.47-3.59(m,3H),3.73-3.89(m,3H),6.45-6.71(m ,1H),6.77-6.99(m,2H),7.73-7.87(m,1H),8.53-8.62(m,1H),8.62-8.76(m,1H).

[0269] Step B: Preparation of N-[5-[6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate methyl (compound 4) A mixture of 3-bromo-N-(4-fluoro-3-methoxyphenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide (0.180 g, 0.475 mmol, 1.00 equivalent), 2-methoxycarbonylaminopyridine-5-boronic acid pinacol ester (0.195 g, 0.665 mmol, 1.40 equivalent), and cesium carbonate (0.232 g, 0.712 mmol, 1.50 equivalent) in water (0.94 mL) and 2-methyltetrahydrofuran (2.84 mL) was flushed with argon for 5 minutes. Next, tetrakis(triphenylphosphine)palladium(0) (0.0283 g, 0.0237 mmol, 0.05 equivalent) was added, and the reaction mixture was heated at 100°C under microwave irradiation and stirred for 1 hour. 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 Na2SO4, and concentrated under reduced pressure. The crude residue was purified on a silica gel cartridge (cyclohexane / ethyl acetate) to obtain methyl N-[5-[6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate as a solid. LC-MS (Method C): Rt 1.10 min, m / z=451(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=3.43-3.57(m,3H),3.74-3.97(m,6H),6.50-6.65(m,1H),6.79-6.89(m,1H),6.89-7.02(m ,1H),7.77-7.86(m,1H),7.86-7.98(m,1H),8.13-8.28(m,2H),8.38-8.47(m,1H),8.52-8.64(m,1H),8.69-8.89(m,1H).

[0270] Example 4: Preparation of N-(4-chlorophenyl)-N-methyl-3-[4-(methylcarbamoylamino)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide (compound 6) [ka] Step A: Preparation of 3-bromo-N-(4-chlorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide (compound X-3) [ka] To a solution of 3-bromoimidazo[1,2-a]pyrazine-6-carboxylic acid (compound X-1) (0.950 g, 3.93 mmol, 1.00 equivalent) in dichloromethane (27.5 mL), 4-chloro-N-methylaniline (0.686 mL, 5.50 mmol, 1.40 equivalent), triethylamine (1.66 mL, 11.8 mmol, 3.00 equivalent), and 1-propanephosphonic anhydride (50% in ethyl acetate) (5.84 mL, 9.81 mmol, 2.50 equivalent) were added. The reaction mixture was stirred overnight at room temperature, followed by the addition of water, and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified on a silica gel cartridge (cyclohexane / ethyl acetate) to obtain 3-bromo-N-(4-chlorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide as a white solid. LC-MS (Method C): Rt 0.88 min, m / z=365(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=3.55(s,3H),7.09(br d,J=8.1Hz,2H),7.26(br d,J=8.4Hz,2H),7.82(s,1H),8.63-8.66(m,1H),8.67(d,J=1.5Hz,1H).

[0271] Step B: Preparation of 3-(4-aminophenyl)-N-(4-chlorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide [ka] To a solution of 3-bromo-N-(4-chlorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide (compound X-3) (1.23 g, 3.36 mmol, 1.00 equivalent) in 1,2-dimethoxyethane (60.6 mL) and water (13.5 mL), 4-aminophenylboronate (0.875 g, 5.05 mmol, 1.50 equivalent), tetrakis(triphenylphosphine)palladium (0) (0.390 g, 0.336 mmol, 0.100 equivalent), and sodium carbonate (1.07 g, 10.1 mmol, 3.00 equivalent) were added. The reaction mixture was stirred overnight at 80°C, then quenched with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified on a silica gel cartridge (cyclodichloromethane / methanol) to obtain 3-(4-aminophenyl)-N-(4-chlorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide as a yellow solid. LC-MS (Method C): Rt 0.82 min, m / z=378(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=3.53(s,3H),6.81-6.87(m,1H),7.09(br d,J=8.4Hz,2H),7.22-7.34(m,5H),7.80(s,1H),8.71(s,1H),8.73-8.76(s,1H),

[0272] Step C: Preparation of N-(4-chlorophenyl)-N-methyl-3-[4-(methylcarbamoylamino)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide (compound 6) To a solution of 3-(4-aminophenyl)-N-(4-chlorophenyl)-N-methyl-imidazo[1,2-a]pyrazine-6-carboxamide (50.0 mg, 0.130 mmol, 1.00 equivalent) in dichloromethane (1.30 mL), methylaminoformylchloride (15.0 mg, 0.160 mmol, 1.20 equivalent) was added, and the resulting solution was stirred at room temperature for 3 hours. Triethylamine (0.0180 mL, 0.130 mmol, 1.00 equivalent) was added, and stirring continued overnight at room temperature. Methylaminoformylchloride (15.0 mg, 0.160 mmol, 1.20 equivalent) and another portion of triethylamine (0.0180 mL, 0.130 mmol, 1.00 equivalent) were added, and stirring continued at room temperature for 3 hours. The reaction mixture was quenched with a saturated aqueous solution of NaHCO3 and extracted by passing it through a chromabond pts phase separation cartridge along with the NaHCO3 solution and dichloromethane. The organic layer was concentrated under reduced pressure and purified on a silica gel cartridge (dichloromethane / methanol) to obtain N-(4-chlorophenyl)-N-methyl-3-[4-(methylcarbamoylamino)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide as a yellow gum-like substance. LC-MS (Method C): Rt 0.80 min, m / z=435(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=2.87(s,3H),3.53(s,3H),5.80(br s,1H),7.03-7.18(m,2H),7.21-7.35(m,4H),7.54(d,J=8.4Hz,2H),7.80(s,1H),8.04(s,1H),8.56(br s,1H),8.66-8.88(br s,1H).

[0273] Example 5: Preparation of N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]phenyl]carbamate methyl (compound 28) [ka] To a solution of methyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (prepared, e.g., as described in Tet. Lett., 2015, 56, 4790) (0.110 g, 0.378 mmol, 1.50 equivalents) and 3-bromo-N-(4-chlorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide (compound X-3) (0.100 g, 0.252 mmol, 1.00 equivalent), cesium carbonate (0.166 g, 0.503 mmol, 2.00 equivalents) was added, and the mixture was purged with argon for 5 minutes. Next, tetrakis(triphenylphosphine)palladium(0) (14.7 mg, 0.0126 mmol, 0.0500 equivalents) was added and irradiated in a microwave oven at 100°C for 45 minutes. The mixture was diluted with ethyl acetate, quenched with saturated aqueous solution of NaHCO3, and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by reverse-phase chromatography (water / acetonitrile) to obtain N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]phenyl]carbamate methyl as white crystals. LC-MS (Method C): Rt 0.88 min, m / z=436(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=3.41(s,3H),3.72(s,3H),7.28-7.33(m,4H),7.61(s,2H),7.67-7 .73(m,2H),8.03(s,1H),8.72(d,J=1.5Hz,1H),8.82(s,1H),9.95(s,1H).

[0274] Example 6: Preparation of N-[4-[6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]phenyl]methyl carbamate (compound 58) [ka] To a solution of 3-bromo-N-(4-fluoro-3-methoxyphenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide (compound X-2) (0.150 g, 0.396 mmol) in dioxane / H2O (4:1, 2.5 mL), N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl carbamate (CAS 844500-75-0) (0.274 g, 0.989 mmol), potassium carbonate (0.137 g, 0.989 mmol), and [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.0289 g, 0.0396 mmol) were added. The mixture was stirred at 55°C for 1.5 hours under an N2 atmosphere. Next, the resulting mixture was concentrated under vacuum. The crude product was purified by flash chromatography using a dichloromethane / MeOH gradient. The desired product was further purified by trituration with methyl tert-butyl ether / acetonitrile (1:1) to obtain N-[4-[6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]phenyl]carbamate methyl as a white solid. LC-MS (Method A): Rt 1.13 min, m / z=450(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=9.95(s,1H),8.85(s,1H),8.66(s,1H),8.01(s,1H),7.69(d,J=8.6Hz,2H),7.56(d,J=8.4Hz,2 H),7.23(dd,J=7.8,2.4Hz,1H),7.05(t,J=9.8Hz,1H),6.75(s,1H),3.71(d,J=2.8Hz,6H),3.41(s,3H).

[0275] Example 7: Preparation of N-[4-[6-[(4-cyano-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]phenyl]methyl carbamate (compound 59) [ka] Step A: Preparation of 3-bromo-N-(4-cyano-3-methoxyphenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide (compound X-4) [ka] To a solution of 2-methoxy-4-(methylamino)benzonitrile (0.210 g, 1.29 mmol) and 3-bromoimidazo[1,2-a]pyrazine-6-carboxylic acid (compound X-1) (0.407 g, 1.68 mmol) in pyridine (4.00 mL), 1-propanephosphonic anhydride (50% in ethyl acetate) (2.47 g, 3.88 mmol) was added dropwise at 65°C. The reaction mixture was stirred at 65°C for 2 hours. The reaction mixture was quenched with a saturated solution of NaHCO3 and diluted with ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The crude residue was purified on a silica gel cartridge (cyclohexane / methanol) to obtain 3-bromo-N-(4-cyano-3-methoxyphenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide as a yellow solid. LC-MS (Method A): Rt 1.07 min, m / z=386(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=8.80(d,J=1.2Hz,1H),8.69(d,J=1.4Hz,1H),8.06(s,1H),7.56(d,J=8.2Hz ,1H),7.22(d,J=1.8Hz,1H),6.89(dd,J=8.2,1.8Hz,1H),3.78(s,3H),3.49(s,3H).

[0276] Step B: Preparation of N-[4-[6-[(4-cyano-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]phenyl]methyl carbamate (compound 59) To a solution of 3-bromo-N-(4-cyano-3-methoxyphenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide (compound X-4) (0.150 g, 0.388 mmol) in dioxane / H2O (4:1, 2.5 mL), methyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (0.269 g, 0.971 mmol), potassium carbonate (0.134 g, 0.971 mmol), and [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.0284 g, 0.0388 mmol) were added. The mixture was stirred at 55°C for 1.5 hours under a nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluting with dichloromethane / methanol) to obtain the desired compound, which was further purified by trituration with methyl tert-butyl ether / acetonitrile (1:1) to obtain N-[4-[6-[(4-cyano-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]phenyl]carbamate methyl as a white solid. LC-MS (Method A): Rt 1.11 min, m / z=457(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=9.96(s,1H),8.82(s,1H),8.77(s,1H),8.04(s,1H),7.70(d,J=8.4Hz,2H),7.61(d,J=8.6Hz,2H) ,7.57(d,J=8.2Hz,1H),7.25(d,J=1.2Hz,1H),6.93-6.88(m,1H),3.77(s,3H),3.72(s,3H),3.48(s,3H).

[0277] Example 8: Preparation of 3-[6-(cyclopropanecarbonylamino)-3-pyridyl]-N-(4-fluoro-3-methoxyphenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide (compound 50) [ka] Under an argon atmosphere, N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]cyclopropanecarboxamide (CAS 1201644-41-8) (0.052 mmol) and XPhos Pd G3 (CAS 1445085-55-1) (3.455 mg, 0.00408 mmol) were placed in vials. Next, a solution of 3-bromo-N-(4-fluoro-3-methoxyphenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide (compound X-2) (0.0408 mmol) in 1,4-dioxane (0.40 mL, degassed with argon) was added, followed by a solution of sodium carbonate (12.9 mg, 0.12 mmol) in water (0.10 mL, degassed with argon). The reaction mixture was stirred under argon at 100°C for 16 hours. The solvent was then evaporated. The residue was dissolved in dimethylacetamide (0.4 mL) and methanol (0.4 mL). The resulting suspension was filtered, and the filtrate was purified by reverse-phase chromatography to obtain 3-[6-(cyclopropanecarbonylamino)-3-pyridyl]-N-(4-fluoro-3-methoxyphenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide. LC-MS (Method D): Rt 1.16 min, m / z=461(M+H) +

[0278] Example 9: Preparation of N-[5-[6-[cyanomethyl-(4-fluoro-3-methoxyphenyl)carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate (compound 2) [ka] Step A: Preparation of 3-bromo-N-(cyanomethyl)-N-(4-fluoro-3-methoxyphenyl)imidazo[1,2-a]pyrazine-6-carboxamide [ka] Under an argon atmosphere, a solution of 3-bromoimidazo[1,2-a]pyrazine-6-carboxylic acid (compound X-1) (0.230 g, 0.92 mmol) in ethyl acetate (3.3 mL) was mixed with 2-(4-fluoro-3-methoxyanilino)acetonitrile (CAS 1600967-16-5) (0.150 g, 0.83 mmol), N,N-diisopropylethylamine (0.58 mL, 3.3 mmol), and 1-propanephosphonic anhydride (50% in ethyl acetate) (0.58 g, 0.92 mmol) at 85°C. The reaction mixture was stirred at 85°C for 17 hours. The mixture was then cooled to room temperature and diluted with ethyl acetate, followed by water. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography using a cyclohexane / acetic acid gradient to obtain 3-bromo-N-(cyanomethyl)-N-(4-fluoro-3-methoxyphenyl)imidazo[1,2-a]pyrazine-6-carboxamide as a beige solid. LC-MS (Method C): Rt 0.81 min, m / z=406(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=3.85-3.94(m,3H),4.79(br s,2H),6.68-6.81(m,1H),6.92-7.06(m,2H),7.85(s,1H,)8.56-8.70(m,1H),8.78(br s,1H).

[0279] Step B: Preparation of N-[5-[6-[cyanomethyl-(4-fluoro-3-methoxyphenyl)carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate methyl (compound 2) To a solution of 3-bromo-N-(cyanomethyl)-N-(4-fluoro-3-methoxyphenyl)imidazo[1,2-a]pyrazine-6-carboxamide (0.22 g, 0.54 mmol) in 2-methyltetrahydrofuran (3.3 mL), methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (0.21 g, 0.76 mmol), water (1.1 mL), and cesium carbonate (0.27 g, 0.82 mmol) were added. The reaction mixture was degassed with argon, followed by the addition of tetrakis(triphenylphosphine)palladium(0) (0.032 g, 0.027 mmol). The mixture was heated in a microwave at 100°C for 30 minutes. The reaction mixture was then cooled to room temperature and diluted with water. The resulting suspension was extracted with ethyl acetate. The organic layer was washed with water, followed by brine, dried over sodium sulfate, filtered, and evaporated. The crude product was purified by flash chromatography using a cyclohexane / HCl gradient to obtain methyl N-[5-[6-[cyanomethyl-(4-fluoro-3-methoxyphenyl)carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate as a beige solid. LC-MS (Method C): Rt 0.79 min, m / z=476(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=3.88-3.91(m,6H),4.76(br s,2H),6.74(br d,J=5.45Hz,1H),6.90-7.14(m,2H),7.78(s,1H),7.87(dd,J=8.72,2.18Hz,1H) ,7.94(s,1H),8.25(d,J=8.72Hz,1H),8.46(d,J=2.18Hz,1H),8.69-8.93(m,2H).

[0280] Example 10: Preparation of N-[5-[6-(6-fluoro-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate methyl (compound 42) [ka] Step A: Preparation of N-[5-(6-bromoimidazo[1,2-a]pyrazine-3-yl)-2-pyridyl]methyl carbamate [ka] To a solution of 6-bromo-3-iodoimidazo[1,2-a]pyrazine (2.00 g, 6.17 mmol) in dioxane / H2O (4:1, 45 mL), N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]methyl carbamate (2.58 g, 9.26 mmol), potassium carbonate (2.13 g, 15.4 mmol), and [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.452 g, 0.617 mmol) were added. The mixture was stirred at 40°C for 4 hours under a nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluting with dichloromethane / methanol) to obtain the desired compound, which was further purified by trituration with acetonitrile to obtain methyl N-[5-(6-bromoimidazo[1,2-a]pyrazine-3-yl)-2-pyridyl]carbamate as a grayish-white solid. LC-MS (Method A): Rt 1.032 min, m / z=348(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=10.49(s,1H),9.02(d,J=1.0Hz,1H),8.81(d,J=1.0Hz,1H),8.63(d,J=2.0H z,1H),8.19(dd,J=8.6,2.4Hz,1H),8.13(s,1H),8.02(d,J=8.6Hz,1H),3.72(s,3H).

[0281] Step B: Preparation of N-[5-[6-(6-fluoro-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate methyl (compound 42) Under inert conditions in a glove box, the reactor was packed with XantPhos Pd G3 (CAS 1445085-97-1) (4.99 mg, 0.00526 mmol), sodium carbonate (16.1 mg, 0.150 mmol), and 6-fluoro-1,2,3,4-tetrahydroquinoline (CAS 59611-52-8) (12.8 mg, 0.075 mmol). Next, methyl N-[5-(6-bromoimidazo[1,2-a]pyrazine-3-yl)-2-pyridyl]carbamate (17.41 mg, 0.05003 mmol) in 1,4-dioxane (0.20 mL) was added. The reactor was flushed with argon and then pressurized to 10 bar with carbon monoxide. The reaction mixture was stirred at 80°C for 16 hours. Next, the solvent was evaporated, and dimethylacetamide (0.40 mL) and methanol (0.40 mL) were added to the residue. The resulting suspension was filtered. The residue was purified by reverse-phase preparative chromatography to obtain N-[5-[6-(6-fluoro-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate methyl (compound 42). LC-MS (Method D): Rt 1.21 min, m / z=447(M+H) +

[0282] Example 11: Preparation of N-[5-[6-(6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-carbonyl)imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate methyl (compound 53) [ka] Step A: Preparation of (3-bromoimidazo[1,2-a]pyrazine-6-yl)-(6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-yl)methanone [ka] To a solution of 3-bromoimidazo[1,2-a]pyrazine-6-carboxylic acid (compound X-1) (100 mg, 0.413 mmol) and 6-fluoro-4-methyl-2,3-dihydro-1H-quinoxaline (0.0696 g, 0.454 mmol) in pyridine (2.0 mL), 1-propanephosphonic anhydride (50% in ethyl acetate) (0.789 g, 1.24 mmol) was added dropwise at 65°C under a nitrogen atmosphere. The mixture was heated at 65°C for 2 hours. The reaction mixture was diluted with saturated aqueous solution of NaHCO3 and extracted with ethyl acetate. The combined organic layers were washed with water, dried over sodium sulfate, filtered, and concentrated under vacuum. The residue was purified by silica gel column chromatography (eluting with dichloromethane / methanol) to obtain (3-bromoimidazo[1,2-a]pyrazine-6-yl)-(6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-yl)methanone as a green solid. LC-MS (Method A): Rt 1.20 min, m / z=390(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=9.00(s,1H),8.67(d,J=1.0Hz,1H),8.08(s,1H),7.19(s,1H),6.53( dd,J=12.0,2.4Hz,1H),6.19(s,1H),3.89(s,2H),3.43(s,2H),2.94(s,3H).

[0283] Step B: Preparation of N-[5-[6-(6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-carbonyl)imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate methyl (compound 53) To a solution of (3-bromoimidazo[1,2-a]pyrazine-6-yl)-(6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-yl)methanone (0.150 g, 0.384 mmol) in dioxane / H2O (4:1, 2.5 mL), N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]methyl carbamate (0.160 g, 0.577 mmol), potassium carbonate (0.133 g, 0.961 mmol), and [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.0281 g, 0.0384 mmol) were added. The mixture was stirred at 50°C for 1.5 hours under a nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluted with dichloromethane / methanol) to obtain the desired compound, which was further purified by trituration with acetonitrile to obtain methyl N-[5-[6-(6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-carbonyl)imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate as a yellow solid. LC-MS (Method A): Rt 1.14 min, m / z=462(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=10.10(s,1H),9.00(s,1H),8.71(s,1H),8.59(d,J=1.0Hz,1H),8.10-8.06(m,2H),7.99(d,J=8.6Hz,1H),7.07(s,1H) ,6.49(dd,J=12.0,2.4Hz,1H),6.18(t,J=7.2Hz,1H),3.89(t,J=5.2Hz,2H),3.73(s,3H),3.42(t,J=5.2Hz,2H),2.93(s,3H).

[0284] Example 12: Preparation of 3-(4-acetamidophenyl)-N-(4-fluorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide (compound 38) [ka] Step A: Preparation of 3-bromo-N-(4-fluorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide [ka] To a solution of 3-bromoimidazo[1,2-a]pyrazine-6-carboxylic acid (compound X-1) (0.200 g, 0.83 mmol, 1.00 equivalent) in dichloromethane (5.8 mL), 4-fluoro-N-methylaniline (0.139 mL, 1.16 mmol, 1.40 equivalent), triethylamine (0.35 mL, 2.48 mmol, 3.00 equivalent), and 1-propanephosphonic anhydride (50% in ethyl acetate) (1.23 mL, 2.07 mmol, 2.50 equivalent) were added. The reaction mixture was stirred overnight at room temperature, followed by the addition of water, and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified on a silica gel cartridge (cyclohexane / ethyl acetate) to obtain 3-bromo-N-(4-fluorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide as a white solid. LC-MS (Method C): Rt 0.77 min, m / z=351(M+H) +

[0285] Step B: Preparation of 3-(4-acetamidophenyl)-N-(4-fluorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide (compound 38) A mixture of 3-bromo-N-(4-fluorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide (0.210 g, 0.601 mmol) and 4-acetamidophenylboronic acid (0.224 g, 1.20 mmol, 2.00 equivalents) in 1,2-dimethoxyethane (0.69 mL) was flushed with nitrogen for 5 minutes. Next, tetrakis(triphenylphosphine)palladium(0) (0.0035 g, 0.0030 mmol, 0.05 equivalents) was added, followed by a solution of potassium fluoride (0.0699 g, 1.20 mmol, 2.00 equivalents) in water (1.20 mL). The reaction mixture was heated at 100°C under microwave irradiation and stirred for 1 hour. The reaction mixture was cooled to room temperature, and then saturated aqueous solution of sodium bicarbonate was added. The aqueous layer was extracted with ethyl acetate, the combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluted with dichloromethane / methanol) to obtain 3-(4-acetamidophenyl)-N-(4-fluorophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide as a beige solid. LC-MS (Method C): Rt 0.75 min, m / z=404(M+H) +

[0286] Example 13: Preparation of N-[5-[6-[(4-cyano-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]methyl carbamate (compound 60) [ka] To a solution of 3-bromo-N-(4-cyano-3-methoxyphenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide (0.150 g, 0.388 mmol) in dioxane / H2O (4:1, 2.5 mL), N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate methyl (0.270 g, 0.971 mmol), potassium carbonate (0.134 g, 0.971 mmol), and [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.0284 g, 0.0388 mmol) were added. The mixture was stirred at 55°C for 1.5 hours under a nitrogen atmosphere. The reaction mixture was then concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluted with dichloromethane / methanol) to obtain the desired compound, which was further purified by trituration with methyl tert-butyl ether / acetonitrile (1:1) to obtain methyl N-[5-[6-[(4-cyano-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate as a white solid. LC-MS (Method A): Rt 1.01 min, m / z=458(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=10.53(s,1H),8.85(d,J=1.2Hz,1H),8.80(d,J=1.2Hz,1H),8.62(d,J=1.8Hz,1H),8.16-8.09(m,2H),8.05(d,J=8. 6Hz,1H),7.57(d,J=8.2Hz,1H),7.24(d,J=1.8Hz,1H),6.91(dd,J=8.2,1.8Hz,1H),3.77(s,3H),3.73(s,3H),3.48(s,3H).

[0287] Biological examples: The fungicidal activity of the compound of the present invention was tested as follows.

[0288] Monographella nivalis (Microdochium nivale) / Liquid culture (grass affected by hemlock) Fungal conidia stored at low temperatures were directly mixed into a nutrient solution medium (PDB potato dextrose broth). After adding a (DMSO) solution of the test compound to a microtiter plate (96-well type), the nutrient solution medium containing fungal spores was added. The test plates were incubated at 24°C, and growth inhibition was measured by photometric analysis 4-5 days after application.

[0289] The following compounds, at 20 ppm, provided at least 80% control of Monographella nivalis when compared to an untreated control that showed widespread disease development under identical conditions: 5, 6, 8, 28, 34.

[0290] Phytophthora infestans / Tomato / Leaf blight preventative (leaf blight) Tomato leaf fragments are placed on agar plates in a multi-well plate (24-well type), and the formulated test compound, diluted in water, is sprayed onto them. One day after application, a suspension of fungal spores is inoculated onto the leaf fragments. The inoculated leaf fragments are incubated in a climate cabinet at 16°C and 75% rh under a light environment of 24 hours in darkness, followed by 12 hours of light / 12 hours of darkness. The activity of the compound is evaluated as the disease control rate compared to the untreated leaf fragments when an appropriate level of disease damage appears on the untreated test leaf fragments (5-7 days after application).

[0291] The following compounds, at 200 ppm, provided at least 80% control of Phytophthora infestans, which exhibited widespread disease development, compared to an untreated control under identical conditions: 1, 2, 3, 4, 37, 42, 46, 50, 51, 58, 59

[0292] Plasmopara viticola / Grape / Leaf blight preventative (leaf blight) Grapevine leaflets are placed on agar plates in a multi-well plate (24-well type), and the test compound, diluted with water, is sprayed onto them. One day after application, a suspension of fungal spores is inoculated onto the leaflets. The inoculated leaflets are incubated in a climate cabinet under a 12-hour light / 12-hour darkness environment at 19°C and 80% rh. The activity of the compound is evaluated as the disease control rate compared to untreated leaflets when an appropriate level of disease damage appears on untreated test leaflets (6-8 days after application).

[0293] The following compounds, at 200 ppm, provided at least 80% control of Plasmopara viticola compared to an untreated control that showed widespread disease development under identical conditions: 1, 6, 8, 28, 36, 37, 55, 58, 59

[0294] Pythium ultimum / Liquid culture (Seedling blight) Newly grown fungal mycelial fragments and oospores from liquid culture are directly mixed into a nutrient medium (PDB potato dextrose medium). After placing a (DMSO) solution of the test compound into a microtiter plate (96-well type), the nutrient medium containing the fungal mycelium / spore mixture is added. The test plate is incubated at 24°C, and the inhibition of growth is measured by photometry 2-3 days after application.

[0295] The following compounds, at 20 ppm, provided at least 80% control of Pythium ultimum when compared to an untreated control that exhibited widespread disease development under identical conditions. 1, 2, 3, 4, 9, 27, 28, 34, 38, 53, 55, 58, 59

Claims

1. Equation (I) 【Chemistry 1】 (wherein Z is O or S, preferably Z is O; A 1 is CH or N, preferably N; R 1a and R 1b are each 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; 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 four A 2 CR 2 Provided that; R 2 These are independently 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 Selected from alkylcarbonyl, 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 hydrogen, 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 alkylsulfanyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, amino, C 1-6 alkylamino, diC 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 alkylsulfanyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, amino, C 1-6 alkylamino, diC 1-6 -alkylamino, and C 3-6 cycloalkylamino group may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxy, and CN; 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, di-C 1-6 alkylaminocarbonyl-C 1-6 alkyl, and CN, and is selected from; the C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 alkoxy, C 1-6 alkylsulfanyl-C 1-6 alkyl, C[[ID=6⑦]] 1-6 alkylsulfinyl-C 1-6 [[ID=7⑩]]alkyl, C 1-6 alkylsulfonyl-C 1-6 alkyl, C 1-6 alkoxycarbonyl-C 1-6 alkyl, C 1-6 alkylaminocarbonyl-C 1-6 alkyl and di-C 1-6 alkylaminocarbonyl-C 1-6 each of the alkyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen and CN; A 3 and R 4 They may optionally come together to 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, 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 CNs.) A compound of, The compound of formula (I) is a compound used as a fungicide; or its salt or N-oxide.

2. Equation (I) 【Chemistry 2】 (wherein Z is O or S, preferably Z is O; A 1 is CH or N, preferably N; R 1a and R 1b These are independently 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 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 four A 2 CR 2 Provided that; R 2 These are independently 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 Selected from alkylcarbonyl, 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 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; at least two R 2 Provided that it is not hydrogen; A 3 CR is independent 3 or N; R 3 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, 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 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 cycloalkylamino group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs; R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl, diC 1-6 Alkylaminocarbonyl-C 1-6 Selected from alkyl and CN, 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 They may optionally come together to 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, 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 CNs.) Compounds of the same; or salts or N-oxides thereof.

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

4. R 1a and R 1b The compound according to any one of claims 1 to 3, wherein the compound is hydrogen.

5. R 2 However, independently, hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Selected from alkoxy, the C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 The compound according to any one of claims 1 to 4, wherein each alkoxy group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs.

6. R 3 However, hydrogen, hydroxyl, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 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 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 5, wherein each cycloalkylamino group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs.

7. The four A's 2 However, CR 2 A 3 The compound according to any one of claims 1 to 6, wherein the compound is N. 【Request Item 8】 【Chemistry 3】 but, 【Chemistry 4】 Preferably, three A 2 However, CR 2 A 3 However, CR 3 The compound according to any one of claims 1 to 6. 【Request Item 9】 【Chemistry 5】 but, 【Transformation 6】 Preferably, three A 2 However, CR 2 A 3 However, CR 3 The compound according to any one of claims 1 to 6.

10. The four A's 2 However, CR 2 A 3 However, CR 3 Preferably, 【Transformation 7】 but, 【Transformation 8】 The compound according to any one of claims 1 to 6.

11. R 4 However, C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, 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 10, wherein each alkoxy group may be optionally substituted with one to three substituents independently selected from halogens and CNs.

12. R 5 However, C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl and C 1-6 Alkoxy C 1-6 The compound according to any one of claims 1 to 11, wherein each of the groups is selected from alkyl groups and each of the groups is optionally substituted with one to three substituents independently selected from halogens and CNs.

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

14. The composition according to claim 13, wherein the composition further comprises at least one compound selected from additional active ingredients, suitable 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, 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 (XXIII) 【Chemistry 9】 (wherein Z is O or S, preferably Z is O; A 1 is CH or N, preferably N; R 1a and R 1b These are independently 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 from alkyl groups; preferably R 1a and R 1b is hydrogen; 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 four A 2 CR 2 Provided that; R 2 These are independently 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 Selected from alkylcarbonyl, 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 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; at least two R 2 Provided that it is preferably not hydrogen; A 3 CR is independent 3 or N; R 3 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, 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 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 cycloalkylamino group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs; R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl, diC 1-6 Alkylaminocarbonyl-C 1-6 Selected from alkyl and CN, 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 1 to 3 substituents independently selected from halogens and CNs; and A 3 and R 4 (These elements can optionally combine to form a ring, more preferably a 5- to 8-membered heteroring, or more preferably a 6-membered heteroring.) Compounds of the same; or salts or N-oxides thereof.

17. Formula (IV) 【Chemistry 10】 (wherein Z is O or S, preferably Z is O; R 1a and R 1b These are independently 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 from alkyl groups; preferably R 1a and R 1b is hydrogen; 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 four A 2 CR 2 Provided that; R 2 These are independently 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 Selected from alkylcarbonyl, 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 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; at least two R 2 Provided that it is preferably not hydrogen; R 3 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, 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 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 cycloalkylamino group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs; R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl, diC 1-6 Alkylaminocarbonyl-C 1-6 Selected from alkyl and CN, 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 1 to 3 substituents independently selected from halogens and CNs; and A 3 and R 4 (These elements can optionally combine to form a ring, more preferably a 5- to 8-membered heteroring, or more preferably a 6-membered heteroring.) Compounds of the same; or salts or N-oxides thereof; Or Formula (II) 【Chemistry 11】 (wherein Z is O or S, preferably Z is O; R 1a and R 1b These are independently 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 from alkyl groups; preferably R 1a and R 1b is hydrogen; 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 four A 2 CR 2 Provided that; R 2 These are independently 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 Selected from alkylcarbonyl, 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 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; at least two R 2 Provided that it is preferably not hydrogen; A 3 CR is independent 3 or N; R 3 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, 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 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 cycloalkylamino group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs; R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl, diC 1-6 Alkylaminocarbonyl-C 1-6 Selected from alkyl and CN, 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 They may optionally combine to form a ring, more preferably a 5- to 8-membered heteroring, more preferably a 6-membered heteroring; and X is Cl, Br, or I); Compounds of the same; or salts or N-oxides thereof.

18. Formula (XVIII) 【Chemistry 12】 (In the formula, A 1 is CH or N, preferably N; R 1a and R 1b These are independently 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 from alkyl groups; preferably R 1a and R 1b is hydrogen; 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, 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 CNs.) Compounds of the same; or salts or N-oxides thereof; Or Formula (XX) 【Chemistry 13】 (In the formula, A 1 is CH or N, preferably N; R 1a and R 1b These are independently 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 from alkyl groups; preferably R 1a and R 1b is hydrogen; 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 CNs; and R 9 C 1-6 (It is alkyl.) Compounds of the same; or salts or N-oxides thereof; Or Formula (XXI) 【Chemistry 14】 (In the formula, A 1 is CH or N, preferably N; R 1a and R 1b These are independently 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 from alkyl groups; preferably R 1a and R 1b is hydrogen; R 5 is C 1-6 alkyl, C 1-6 alkoxy, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkylamino, di-C 1-6 alkylamino, and C 1-6 alkyl-C 1-6 alkoxyamino, and each of the above groups may be optionally substituted with 1 to 3 substituents independently selected from halogen and CN; and X is Cl, Br, or I); Compounds of the same; or salts or N-oxides thereof.

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