Pyrazolo[1,5-a]pyridine derivatives

Abstract

The present invention relates to formula (I) [Formula 1] JPEG2026514064000113.jpg58160 (wherein the formula, the substituents are as defined in claim 1) The present invention relates to a compound of formula (I), a process and method for preparing a compound of formula (I), a pesticide composition comprising a compound of formula (I) as defined in claim 1, the preparation of these compositions, and the use of the compound or composition in agriculture or horticulture for controlling, preventing or controlling ectoparasitism of plants, harvested food crops, seeds or non-biological materials by plant pathogenic microorganisms, particularly fungi.

Description

Technical Field

[0001] The present invention relates to microbicidal activity, particularly fungicidal activity, more specifically activity against oomycetes, for example to microbicidal pyrazolo[1,5-a]pyridine derivatives as active ingredients. The invention relates to the preparation of these pyrazolo[1,5-a]pyridine derivatives, intermediates useful for the preparation of these pyrazolo[1,5-a]pyridine derivatives, the preparation of these intermediates, pesticidal compositions comprising at least one of the pyrazolo[1,5-a]pyridine derivatives, the preparation of these compositions and the use of the pyrazolo[1,5-a]pyridine derivatives or compositions in agriculture or horticulture for controlling, preventing or protecting plants, harvested food crops, seeds or abiotic materials from ectoparasitism by phytopathogenic microorganisms, particularly fungi, more specifically oomycetes.

Background Art

[0002] Surprisingly, it has now been found that certain novel pyrazolo[1,5-a]pyridine derivatives have particularly advantageous fungicidal properties against oomycetes.

Summary of the Invention

Means for Solving the Problems

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

Chemical Formula

[0004] In a particular embodiment of this first aspect, the present invention relates to a fungicide of 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 , R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Independently selected from alkyl groups, preferably R 1a , R 1b and R 1c It 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 The condition is that, R 2 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Independently selected from alkylcarbonyls, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxyl, and CN, preferably R 2 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 Alkoxycarbonyl and C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Independently selected from alkylcarbonyls, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxyl, and CN, preferably R 2 Hydrogen, halogen, CN, C 1-6Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl and C 1-6 Alkoxy-C 1-6 Selected independently of alkoxy, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl 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 R 2 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxycarbonyl and C 1-6 Selected independently of 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 1-6Alkyl, 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 halogen, hydroxyl, and CN, preferably R 3 It 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, C2-6 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 Together, they arbitrarily form a ring, preferably a 5-8 membered heterocycle, more preferably a 6-membered heterocycle, and R 5 C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, diC 1-6 Alkylamino 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. This may relate to the use of the compound or its salt or N-oxide.

[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) A1 is CH or N, preferably N. R 1a , R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Independently selected from alkyl groups, preferably R 1a , R 1b and R 1c It 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 The condition is that, R 2 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Independently selected from alkylcarbonyls, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, 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. However, at least two R 2 This is provided that it is not hydrogen, and 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 of the alkoxy groups is independently selected from halogen, hydroxyl, and CN, more preferably halogen, CN, and C 1-6 Alkyl and C 1-6 It may be optionally substituted with 1 to 3 substituents selected from alkoxys. A3 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, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkylsulfonyl, amino, C 1-6 Alkylamino, diC 1-6 -Alkylamino and C 3-6 Each of the cycloalkylamino groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxyl, and CN, preferably R 3 It is hydrogen, R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6Alkyl, 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. A 3 and R 4 Together, they arbitrarily form a ring, preferably a 5-8 membered heterocycle, more preferably a 6-membered heterocycle, and R 5 C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, diC 1-6 Alkylamino 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. This may relate to compounds of the same, or their salts or N-oxides.

[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 formulation inert ingredients, carriers, auxiliaries, and any mixtures thereof.

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

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

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

[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) described herein or compositions comprising compounds of formula (I) for the control of 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) 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 plant reproductive material. According to this sixth aspect of the present invention, this method may exclude methods of treating the body of a human or animal by surgery or treatment.

[0012] When it is indicated that one group is substituted (e.g., alkyl), this includes these groups being part of the other groups (e.g., alkyl in alkylthio). [Modes for carrying out the invention]

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

[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 represents a linear or branched hydrocarbon having 2 to 6 carbon atoms and at least one triple bond, such as 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl This represents 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, and 2,5-hexadinyl. Alkynnyls having 2 to 4 carbon atoms are preferred, for example, ethinyl, 2-propynyl, or 2-butynyl-2-propenyl.

[0018] - The term "haloalkyl" refers to the alkyl groups as generally defined above, such as fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, or 2,2,2-trifluoroethyl, which are substituted by one or more of the same or different halogen atoms.

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

[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, as generally defined above, that is substituted by one or more of the same or different halogen atoms.

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

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

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

[0028] - The term "alkoxycarbonyl" is derived from the formula R a It refers to the OC(O)- group, R a This is an alkyl group as generally defined above.

[0029] - The term "alkylamino" is derived from the formula R a It refers to the NH- group, R a This is an alkyl group as generally defined above.

[0030] - The term "cycloalkylamino" is derived from the formula R a It refers to the NH- group, R a This is a cycloalkyl group as generally defined above.

[0031] - The term "alkoxyamino" is derived from the formula R a It refers to the NH- group, R a This is an alkoxy group as generally defined above.

[0032] - The term "alkylaminocarbonyl" is derived from the formula R a It refers to the NHC(O)- group, R a This is an alkyl group as generally defined above.

[0033] - Hydroxyl or hydroxy represents the -OH group.

[0034] In relation to the present invention, the terms “to eradicate,” “to prevent,” or “to control,” and their variations thereof, mean reducing pathogenicity, more specifically any undesirable effects of plant pathogens, particularly fungi such as oomycetes, exocytosis or attack on plants or plant-derived products, and pathogenic damage, to a level in which improvement is demonstrated.

[0035] As used herein, the term "effective amount" refers to the amount of a compound, its salt, or N-oxide that produces the desired effect through one or more applications.

[0036] The effective dose can be readily determined by those skilled in the art by using known techniques and observing the results obtained under similar circumstances. In determining the effective dose, many factors are considered, including but not limited to, the type of plant or derivative product to be applied, the pathogen being controlled and its life cycle, the specific compound to be applied, the type of application, and other relevant circumstances.

[0037] 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; strong organic carboxylic acids, such as unsubstituted or substituted C1-C4 alkanecarboxylic acids, such as acetic acid; saturated or unsaturated dicarboxylic acids, such as oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, or phthalic acid; hydroxycarboxylic acids, such as ascorbic acid, lactic acid, malic acid, tartaric acid, or citric acid; or benzoic acid; or organic sulfonic acids, such as unsubstituted or substituted C1-C4 alkane- or leelesulfonic acids, such as methane- or p-toluenesulfonic acid. Compounds of formula (I) having at least one acidic group may form salts with a base, for example, mineral salts, for example alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or salts with ammonia or organic amines, for example morpholine, piperidine, pyrrolidine, mono-, di- or tri-lower alkylamines, for example ethyl-, diethyl-, triethyl or dimethylpropylamine, or mono-, di or trihydroxy lower alkylamines, for example mono-, di- or triethanolamine.

[0038] In each case, the compound of formula (I) according to the present invention is in the form of 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.

[0039] The compound of formula (I) according to the present invention also includes a hydrate, which may be formed during salt formation.

[0040] In further embodiments, the compound of formula (I) according to the present invention is R 1a , R 1b and R 1c is hydrogen, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected independently of alkoxys, preferably R 1a , R 1b and R 1c A compound is provided, which is hydrogen.

[0041] In further embodiments, the compound of formula (I) according to the present invention is 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 3-6Compounds are provided in which each of the cycloalkylamino groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs. In a preferred embodiment, R 3 It could be hydrogen.

[0042] In a further embodiment, the compound of formula (I) according to the present invention comprises four A 2 CR 2 A 3 A compound is provided in which N is present.

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

[0044] In further embodiments, the compound of formula (I) according to the present invention is: [ka] teeth, [ka] Preferably, three A 2 CR 2 A 3 CR 3 A compound is provided.

[0045] In a further embodiment, the compound of formula (I) according to the present invention comprises four A 2 CR 2 A 3 CR 3 Preferably, [ka] teeth, [ka] A compound is provided.

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

[0047] In further embodiments, the compound of formula (I) according to the present invention is R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl and C 1-6 Selected from alkoxy, C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl and C 1-6Each 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. A 3 and R 4 The compounds provided are those which together form a ring, more preferably a 5-8 membered heterocycle, and more preferably a 6 membered heterocycle.

[0048] In a further embodiment, the compound of formula (I) according to the present invention is A 3 CR 3 And R 3 and R 4 Together, they form a ring, preferably a 5-8 membered heterocycle, preferably a 6 membered heterocycle, more preferably a ring W1, W2, or W3 as described in the compound of formula (I) below: [ka] A compound, which is one of them, is provided.

[0049] The carbon and / or nitrogen atoms forming the ring (W1, W2, or W3) are, in particular, R 3’ It can be substituted by the group R 3’ is hydrogen, C 1-6 Alkyl and C 3-6 Selected from cycloalkyl, C 1-6 Alkyl and C3-6 Each cycloalkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN. For example, the compound of formula (I-W3) may be as follows: [ka]

[0050] In preferred embodiments, the compounds of formulas (I-W1), (I-W2), and (I-W3) may be as described below. [ka]

[0051] The carbon and / or nitrogen atoms forming the ring (W1, W2, or W3) are, in particular, R 3’ It can be substituted by the group 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 compound of formula (I-W3) may be as follows: [ka]

[0052] In further embodiments, the compound of formula (I) according to the present invention is R 5 C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl and C 1-6 Alkoxy C 1-6 Compounds are provided, selected from alkyl groups, each of which may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN.

[0053] In a particular embodiment, the compound of formula (I) according to the present invention is, Z is O, A 1 N is, 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 It is hydrogen, R 1b These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 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 It is hydrogen, R 1c These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6Alkoxy, amino, and NHC(O)C 1-6 Selected from alkyl groups, preferably R 1c It is hydrogen, The four A's 2 CR 2 And R 2 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Independently selected from alkylcarbonyls, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 The alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxyl, and CN, preferably R 2 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl and C 1-6 Alkoxy-C 1-6 Selected independently of alkoxy, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl and C 1-6 Alkoxy-C 1-6Each alkoxy group may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxyl, and CN, more preferably R 2 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxycarbonyl and C 1-6 Selected independently of alkoxy, A 3 CR 3 R is 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 independently 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 halogen, hydroxyl, and CN, preferably R 3 It is hydrogen, R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C1-4 Alkyl and C 1-6 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 combine to arbitrarily form a ring, more preferably a 5-8 membered heteroring, more preferably a 6 membered heteroring. 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 Compounds are provided, selected from alkyl groups, each of which may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN.

[0054] In a preferred embodiment, [ka] teeth, [ka] And R 2 This is as defined in the present invention, and preferably R 2 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy C 1-6 Alkyl, 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 Independently selected from alkylcarbonyls, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 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 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl and C 1-6 Alkoxy-C 1-6 Selected independently of alkoxy, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C1-6 Alkyl, C 1-6 Alkoxycarbonyl 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, and more preferably R 2 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxycarbonyl and C 1-6 It is selected independently of alkoxy.

[0055] In further embodiments, the compound according to the present invention is Methyl N-[5-[5-[(4-fluoro-3-methoxyphenyl)-(methoxymethyl)carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[5-[(4-chloro-3-methoxyphenyl)-(cyanomethyl)carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[5-[cyanomethyl-(4-fluoro-3-methoxyphenyl)carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate, Methyl N-[5-[5-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate, Methyl N-[4-[5-[(4-chlorophenyl)-methyl-carbamoyl]pyrazolo[1,5-a]pyridine-3-yl]phenyl]carbamate, 3-(4-acetamidophenyl)-N-(4-chlorophenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, Methyl N-[5-[5-[(6-methoxy-3-pyridyl)-methyl-carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate, 3-(6-acetamido-3-pyridyl)-N-(6-methoxy-3-pyridyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, 3-(4-acetamidophenyl)-N-(6-methoxy-3-pyridyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, 3-[4-[(2-methoxyacetyl)amino]phenyl]-N-(6-methoxy-3-pyridyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, 3-[6-(ethylcarbamoylamino)-3-pyridyl]-N-(6-methoxy-3-pyridyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, Methyl N-[5-[5-[(4-cyanophenyl)-methyl-carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate, 3-(6-acetamido-3-pyridyl)-N-(4-cyanophenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, 3-(4-acetamidophenyl)-N-(4-cyanophenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, N-(4-cyanophenyl)-3-[4-[(2-methoxyacetyl)amino]phenyl]-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, N-(4-cyanophenyl)-3-[6-(ethylcarbamoylamino)-3-pyridyl]-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, Methyl N-[5-[5-[(2-methoxy-4-pyridyl)-methyl-carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate, 3-(6-acetamido-3-pyridyl)-N-(2-methoxy-4-pyridyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, 3-(4-acetamidophenyl)-N-(2-methoxy-4-pyridyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, 3-[4-[(2-methoxyacetyl)amino]phenyl]-N-(2-methoxy-4-pyridyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, 3-[6-(ethylcarbamoylamino)-3-pyridyl]-N-(2-methoxy-4-pyridyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, Methyl N-[5-[5-[(3-fluorophenyl)-methyl-carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate, 3-(6-acetamido-3-pyridyl)-N-(3-fluorophenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, 3-(4-acetamidophenyl)-N-(3-fluorophenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, N-(3-fluorophenyl)-3-[4-[(2-methoxyacetyl)amino]phenyl]-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, 3-[6-(ethylcarbamoylamino)-3-pyridyl]-N-(3-fluorophenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, Methyl N-[5-[5-[(4-methoxy-2-pyridyl)-methyl-carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate, 3-(6-acetamido-3-pyridyl)-N-(4-methoxy-2-pyridyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, 3-(4-acetamidophenyl)-N-(4-methoxy-2-pyridyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, 3-[4-[(2-methoxyacetyl)amino]phenyl]-N-(4-methoxy-2-pyridyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, 3-[6-(ethylcarbamoylamino)-3-pyridyl]-N-(4-methoxy-2-pyridyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, Methyl N-[5-[5-[(6-cyano-3-pyridyl)-methyl-carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate, 3-(6-acetamido-3-pyridyl)-N-(6-cyano-3-pyridyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, 3-(4-acetamidophenyl)-N-(6-cyano-3-pyridyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, N-(6-cyano-3-pyridyl)-3-[4-[(2-methoxyacetyl)amino]phenyl]-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, N-(6-cyano-3-pyridyl)-3-[6-(ethylcarbamoylamino)-3-pyridyl]-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, Methyl N-[5-[5-[(6-chloro-3-pyridyl)-methyl-carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate, 3-(4-acetamidophenyl)-N-(6-chloro-3-pyridyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, N-(6-chloro-3-pyridyl)-3-[4-[(2-methoxyacetyl)amino]phenyl]-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, N-(6-chloro-3-pyridyl)-3-[6-(ethylcarbamoylamino)-3-pyridyl]-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, 3-(6-acetamido-3-pyridyl)-N-(4-cyano-3-methoxyphenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide, Methyl N-[5-[5-[(4-cyano-3-methyl-phenyl)-methyl-carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate, 3-(6-Acetamido-3-pyridyl)-N-(4-cyano-3-methyl-phenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, 3-(4-Acetamidophenyl)-N-(4-cyano-3-methyl-phenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, N-(4-Cyano-3-methyl-phenyl)-3-[4-[(2-methoxyacetyl)amino]phenyl]-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, N-(4-Cyano-3-methyl-phenyl)-3-[6-(ethylcarbamoylamino)-3-pyridyl]-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide, and 3-(6-Acetamido-3-pyridyl)-N-(4-fluoro-3-methoxy-phenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide is selected from.

[0056] The method according to the invention has advantageous properties for protecting plants from attacks or ectoparasites which cause diseases and damage to plants, such as pathogenic, for example fungal, especially oomycetes, plant pathogens, and in particular in the case of plants, the invention can control, limit or prevent pathogenic damage to plants, parts of plants, plant propagation material and / or grown plants.

[0057] The compounds in Tables 1.1 to 1.45 below illustrate specific compounds of the invention.

[0058] Table 1.1 shows formula (Ia)

Chemical formula

[0059] More specifically, Table Z includes compounds in which A 3 and R 4 together form a ring. In this case, the ring is along the amide atom linked to the bicyclic core of formula (Ia) and together with A 3 and R 4 is shown in the column (Table Z) of. For example, refer to the column of A 3 and R 4 of compound E1.36

[0060]

Table 1-1

[0061]

Table 1-2

[0062]

Table 1-3

[0063]

Table 1-4

[0064]

Table 1-5

[0065]

Table 1-6

[0066]

Table 1-7

[0067] Table 1-8

[0068] Table 1-9

[0069] Table 1-10

[0070] Table 1-11

[0071] Table 1-12

[0072] Table 1-13

[0073] Table 1-14

[0074] Table 1-15

[0075] Table 1-16

[0076] Table 1-17

[0077] Table 1-18

[0078] Table 1-19

[0079] Table 1-20

[0080] Table 1-21

[0081] Table 1-22

[0082] Table 1-23

[0083] Table 1-24

[0084] Table 1-25

[0085] Table 1-26

[0086] Table 1-27

[0087] [Table 1-28]

[0088] Table 1.2 provides 483 compounds E2.1 to E2.483 of formula (Ia), and A 2a N is R 5 It is OCH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0089] Table 1.3 provides 483 compounds E3.1 to E3.483 of formula (Ia), and A 2a N is R 5 It is cyclopropyl, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0090] Table 1.4 provides 483 compounds E4.1 to E4.483 of formula (Ia), and A 2a N is R 5 It is CH2OCH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0091] Table 1.5 provides 483 compounds E5.1 to E5.483 of formula (Ia), and A 2a N is R 5 It is NHCH2CH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0092] Table 1.6 provides 483 compounds E6.1 to E6.483 of formula (Ia), and A2a is CH, and R 5 is CH3, and R 2 , A 3 , R 4 , A 1 , A 2b is as defined in Table Z.

[0093] Table 1.7 provides 483 compounds E7.1 - E7.483 of formula (Ia), and A 2a is CH, and R 5 is OCH3, and R 2 , A 3 , R 4 , A 1 , A 2b is as defined in Table Z.

[0094] <s Table 1.8 provides 483 compounds E8.1 - E8.483 of formula (Ia), and A 2a is CH, and R 5 is cyclopropyl, and R 2 , A 3 , R 4 , A 1 , A 2b is as defined in Table Z.

[0095] Table 1.9 provides 483 compounds E9.1 - E9.483 of formula (Ia), and A 2a is CH, and R 5 is CH2OCH3, and R 2 , A 3 , R 4 , A 1 , A 2b is as defined in Table Z.

[0096] Table 1.10 provides 483 compounds E10.1 - E10.483 of formula (Ia), and A 2a is CH, and R 5 is NHCH2CH3, and R 2 , A 3 , R 4 , A 1 , A 2b is as defined in Table Z.

[0097] Table 1.11 provides 483 compounds E11.1 to E11.483 of formula (Ia), and A 2a is CF, R 5 It is CH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0098] Table 1.12 provides 483 compounds E12.1 to E12.483 of formula (Ia), and A 2a is CF, R 5 It is OCH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0099] Table 1.13 provides 483 compounds E13.1 to E13.483 of formula (Ia), and A 2a is CF, R 5 It is cyclopropyl, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0100] Table 1.14 provides 483 compounds E14.1 to E14.483 of formula (Ia), and A 2a is CF, R 5 It is CH2OCH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0101] Table 1.15 provides 483 compounds E15.1 to E15.483 of formula (Ia), and A 2a is CF, R 5 It is NHCH2CH3, and R2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0102] Table 1.16 provides 483 compounds E16.1 to E16.483 of formula (Ia), and A 2a is CCl, and R 5 It is CH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0103] Table 1.17 provides 483 compounds E17.1 to E17.483 of formula (Ia), and A 2a is CCl, and R 5 It is OCH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0104] Table 1.18 provides 483 compounds E18.1 to E18.483 of formula (Ia), and A 2a is CCl, and R 5 It is cyclopropyl, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0105] Table 1.19 provides 483 compounds E19.1 to E19.483 of formula (Ia), and A 2a is CCl, and R 5 It is CH2OCH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0106] Table 1.20 provides 483 compounds E20.1 to E20.483 of formula (Ia), and A 2a is CCl, and R 5 It is NHCH2CH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0107] Table 1.21 provides 483 compounds E21.1 to E21.483 of formula (Ia), and A 2a It is CBr, and R 5 It is CH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0108] Table 1.22 provides 483 compounds E22.1 to E22.483 of formula (Ia), and A 2a It is CBr, and R 5 It is OCH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0109] Table 1.23 provides 483 compounds E23.1 to E23.483 of formula (Ia), and A 2a It is CBr, and R 5 It is cyclopropyl, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0110] Table 1.24 provides 483 compounds E24.1 to E24.483 of formula (Ia), and A 2a It is CBr, and R 5 It is CH2OCH3, and R 2 , A 3 , R 4, A 1 , A 2b This is defined in Table Z.

[0111] Table 1.25 provides 483 compounds E25.1 to E25.483 of formula (Ia), and A 2a It is CBr, and R 5 It is NHCH2CH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0112] Table 1.26 provides 483 compounds E26.1 to E26.483 of formula (Ia), and A 2a It is CCH3, and R 5 It is CH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0113] Table 1.27 provides 483 compounds E27.1 to E27.483 of formula (Ia), and A 2a It is CCH3, and R 5 It is OCH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0114] Table 1.28 provides 483 compounds E28.1 to E28.483 of formula (Ia), and A 2a It is CCH3, and R 5 It is cyclopropyl, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0115] Table 1.29 provides 483 compounds E29.1 to E29.483 of formula (Ia), and A2a It is CCH3, and R 5 It is CH2OCH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0116] Table 1.30 provides 483 compounds E30.1 to E30.483 of formula (Ia), and A 2a It is CCH3, and R 5 It is NHCH2CH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0117] Table 1.31 provides 483 compounds E31.1 to E31.483 of formula (Ia), and A 2a It is CCH2CH3, and R 5 It is CH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0118] Table 1.32 provides 483 compounds E32.1 to E32.483 of formula (Ia), and A 2a It is CCH2CH3, and R 5 It is OCH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0119] Table 1.33 provides 483 compounds E33.1 to E33.483 of formula (Ia), and A 2a It is CCH2CH3, and R 5 It is cyclopropyl, and R 2 , A 3 , R 4 , A 1 , A2b This is defined in Table Z.

[0120] Table 1.34 provides 483 compounds E34.1 to E34.483 of formula (Ia), and A 2a It is CCH2CH3, and R 5 It is CH2OCH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0121] Table 1.35 provides 483 compounds E35.1 to E35.483 of formula (Ia), and A 2a It is CCH2CH3, and R 5 It is NHCH2CH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0122] Table 1.36 provides 483 compounds E36.1 to E36.483 of formula (Ia), and A 2a It is CCN, and R 5 It is CH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0123] Table 1.37 provides 483 compounds E37.1 to E37.483 of formula (Ia), and A 2a It is CCN, and R 5 It is OCH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0124] Table 1.38 provides 483 compounds E38.1 to E38.483 of formula (Ia), and A 2aIt is CCN, and R 5 It is cyclopropyl, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0125] Table 1.39 provides 483 compounds E39.1 to E39.483 of formula (Ia), and A 2a It is CCN, and R 5 It is CH2OCH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0126] Table 1.40 provides 483 compounds E40.1 to E40.483 of formula (Ia), and A 2a It is CCN, and R 5 It is NHCH2CH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0127] Table 1.41 provides 483 compounds E41.1 to E41.483 of formula (Ia), and A 2a It is COCH3, and R 5 It is CH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0128] Table 1.42 provides 483 compounds E42.1 to E42.483 of formula (Ia), and A 2a It is COCH3, and R 5 It is OCH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0129] Table 1.43 provides 483 compounds E43.1 to E43.483 of formula (Ia), and A 2a It is COCH3, and R 5 It is cyclopropyl, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0130] Table 1.44 provides 483 compounds E44.1 to E44.483 of formula (Ia), and A 2a It is COCH3, and R 5 It is CH2OCH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0131] Table 1.45 provides 483 compounds E45.1 to E45.483 of formula (Ia), and A 2a It is COCH3, and R 5 It is NHCH2CH3, and R 2 , A 3 , R 4 , A 1 , A 2b This is defined in Table Z.

[0132] The compounds according to the present invention may have many advantages, including, in particular, favorable levels of biological activity for protecting plants from fungal diseases or excellent properties for use as agricultural chemical active ingredients (e.g., higher biological activity, favorable activity spectrum, improved safety profile, improved physicochemical properties, or improved biodegradability). The compounds according to the present invention have particularly favorable levels of biological activity for protecting plants from oomycetes such as Phytophthora, Plasmopara, and Pythium.

[0133] Compounds of formula (I) where Z is O can be prepared as shown in schemes 1 to 13 below, in which, unless otherwise specified, the definition of each variable part is as defined in the present invention.

[0134] The compound of formula (I) is mixed with the compound of formula (II) (where X is Cl, Br, or I) and the compound of formula (III) (R) in the presence of a base such as Cs2CO3, K2CO3, or NaOtBu and 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. 6 These are, independently of each other, hydrogen and C 1-6 Alkyl or two R 6 together become C 3-8 It can be prepared by Suzuki cross-coupling with a compound of formula (III) (R 6 These are, independently of each other, hydrogen and C 1-6 Alkyl or two R 6 These (either of which can combine to form a C3-C8 cycloalkyl group) are prepared by known methods or are commercially available. This transformation is shown in Scheme 1. [ka] Scheme 1

[0135] Compound (II) (where X is Cl, Br, or I) reacts with compound (IV) (where X is Cl, Br, or I) in the presence of a base such as Cs2CO3, K2CO3, NaH, or NaOtBu, and reagent (V) (where X 1 It can be prepared by reacting with a good leaving group such as Cl, Br, I, triflate, tosyl or mesyl. Compound (R) of formula (VI) 7(where X is an electron-withdrawing group such as a cyano or ester) can instead be used to functionalize the amide nitrogen in the presence of a base such as triethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene, optionally. The compound of formula (IV) (where X is Cl, Br or I) is used to functionalize the compound of formula (VII) (X 2 The compound can be prepared by a peptide coupling reaction between the amine of formula (VIII) and the compound of formula (VII), which is usually carried out in a preferably suitable solvent (e.g., N-methylpyrrolidone, acetonitrile, dimethylacetamide, dichloromethane, or tetrahydrofuran), preferably at a temperature of 25°C to 60°C, and optionally in the presence of a base such as triethylamine or N,N-diisopropylethylamine, or alternatively in a preferably suitable solvent (e.g., acetonitrile), optionally in the presence of a base (e.g., triethylamine or N,N-diisopropylethylamine), under the 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 before treatment with the amine of formula (VIII), for example by using (COCl)2 or SOCl2. For example, see Chem.Soc.Rev.2009,38,606 and Chem.Soc.Rev.2011,40,5084. Alternatively, a compound of formula (II) (where X is Cl, Br, or I) can be used to form a compound of formula (VII) (X 2 This can be obtained by amide coupling transformations between the OH group and the amine of formula (IX). These transformations are shown in Scheme 2. [ka] Scheme 2

[0136] The compound of formula (IX) is commercially available, or, in the presence of a base such as Cs2CO3, K2CO3, NaH, or NaOtBu, the compound of formula (VIII) and the compound of formula (V) (X 1The compound of formula (IX) can be obtained by reaction with a good leaving group such as Cl, Br, I, triflate, tosyl, or mesyl. Alternatively, the compound of formula (IX) can be obtained by reacting the compound of formula (VIII) with the compound of formula (VI) (R) in the presence of a base such as triethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene, optionally. 7 The compound of formula (IX) can also be synthesized by reacting it with an electron-withdrawing group (such as a cyano or ester). Alternatively, the compound of formula (IX) can be reacted with an aldehyde (R) of formula (X) 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 or diC 1-6 Alkylaminocarbonyl-C 1-5 It can be obtained from the amine of formula (VIII) 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 (IX) from the amine of formula (VIII) is described in Scheme 3. [ka] Scheme 3

[0137] Alternatively, the compound of formula (II) (where X is Cl, Br, or I) may be prepared by reacting the compound of formula (XI) 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 (XI) is obtained by reacting the compound of formula (XII) (X 2 This can be obtained by amide coupling conversion of the carboxylic acid (which is OH) with the amine of formula (IX) and activation of the carboxylic acid functional group of the compound of formula (XII), which is usually carried out by converting the -OH of the carboxylic acid to a good leaving group such as a chloride group in a preferably suitable solvent (e.g., N-methylpyrrolidone, acetonitrile, dimethylacetamide, dichloromethane, or tetrahydrofuran), preferably at a temperature of 25°C to 60°C and optionally in the presence of a base such as triethylamine or N,N-diisopropylethylamine, or alternatively in a preferably 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), for example by using (COCl)2 or SOCl2. Instead, the compound of formula (XI) transforms the compound of formula (XIII) into the compound of formula (V) in the presence of a base such as Cs2CO3, K2CO3, NaH, or NaOtBu. 1 It can be obtained by alkylating with a good leaving group such as Cl, Br, I, triflate, tosyl or mesyl. Alternatively, the compound of formula (XI) can be obtained by alkylating the compound of formula (XIII) with the compound of formula (VI) (R 7 The compound of formula (XIII) can also be synthesized by reacting it with an electron-withdrawing group (such as a cyano or ester) in the presence of a base such as triethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene, which is optionally a base. 2Since (where is OH), it can be prepared by peptide coupling transformation using the amine of formula (VIII) using the above conditions. These transformations are shown in Scheme 4. [ka] Scheme 4

[0138] Alternatively, the compound of formula (XI) can be synthesized by reacting the compound of formula (XIV) (where X is Cl, Br, or I) with the amine of formula (IX) 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 5. [ka] Scheme 5

[0139] Compound (XII) of formula (X 2 (where is OH) is commercially available or obtained by hydrolyzing the ester moiety under conventional acidic or basic conditions and heating the diacitic acid, resulting in a compound of formula (XV) (R 9 C 1-6 It can be obtained by decarboxylation of the alkyl compound (R 9 C 1-6 The alkyl compound (R) of formula (XVI) is found in a polar organic solvent such as dimethyl sulfoxide, N-methylpyrrolidine, or N,N-dimethylformamide, in the presence of a base such as Na2CO3 or K2CO3. 10 (R is an aryl)sulfonyl, (hetero)arylsulfonyl, or sulfonic acid group, for example, a sulfonic acid, tosylate, or 2,4,6-trimethylbenzenesulfonyl group) and an alkyne of formula (XVII) 9 C 1-6 It can be synthesized by reaction with alkyl. Compounds of formula (XVII) are commercially available or can be readily prepared by those skilled in the art according to the methods described. Compounds of formula (XVI) (R 10(R is an aryl)sulfonyl, (hetero)arylsulfonyl, or sulfonic acid group, for example, sulfonic acid, tosylate, or 2,4,6-trimethylbenzenesulfonyl group) in a polar aproton solvent such as dimethyl sulfoxide, N-methylpyrrolidine, or N,N-dimethylformamide, the compound of formula (XVIII) and the compound of formula (XIX) (R 10 Compounds of formula (XVIII) can be formed by reacting them with (aryl)sulfonyl, (hetero)arylsulfonyl, or sulfonic acid groups (e.g., sulfonic acid, tosylate, or 2,4,6-trimethylbenzenesulfonyl group). Compounds of formula (XVIII) are commercially available or can be prepared using methods known to those skilled in the art. Compounds of formula (XII) (X 2 (is OH) to C 1-6 Further reaction with alkyl alcohol yields an ester of formula (XX) (wherein R, R 11 C 1-6 We can obtain alkyl groups. These transformations are shown in Scheme 6. [ka] Scheme 6

[0140] Instead, the compound of formula (I) is the compound of formula (XXI) (where X is Cl, Br or I, and X 2The compound can be prepared by amide coupling conversion of the compound (XXI) with the amine of formula (IX) and activation of the carboxylic acid functional group of the compound of formula (XXI). This process is usually carried out by converting the -OH of the carboxylic acid to a good leaving group such as a chloride group, for example, by using (COCl)2 or SOCl2, in a preferably 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 preferably 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 cyclic anhydride of 1-propanephosphonic acid (T3P). Instead, the compound of formula (I) transforms the compound of formula (XXII) into the compound of formula (V) in the presence of a base such as Cs2CO3, K2CO3, NaH, or NaOtBu. 1 It can be prepared by alkylating with Cl, Br, I, triflate, tosyl or mesyl (which are good leaving groups). Alternatively, the compound of formula (I) can be converted to the compound of formula (XXII) (R 7 The compound of formula (XXII) can also be synthesized by reacting it with an electron-withdrawing group (such as a cyano or ester) in the presence of a base such as triethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene, optionally. The compound of formula (XXII) can be synthesized using the above conditions to form the compound of formula (XXI)(X 2 It can be synthesized from compounds of formula (VIII) and amines of formula (VIII) by peptide coupling transformations. These transformations are shown in Scheme 7. [ka] Scheme 13

[0141] Compound (X) of formula (XXI) 2 (is OH) is the compound (R) of formula (XXIII). 11 C1-6 It can be obtained by hydrolysis of the ester portion of the alkyl compound (R) of formula (XXIII). 11 C 1-6 The alkyl compound (where X is Cl, Br or I, and R) is prepared in the presence of a base such as Cs2CO3, K2CO3 or NaOtBu and 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, to form a compound of formula (XXIV) (where X is Cl, Br or I, and R 10 C 1-6 (It is alkyl) and the compound of formula (III) (R 6 These are, independently of each other, hydrogen, C1-6 alkyl, or two R 6 together become C 3-8 It can result from a Suzuki cross-coupling reaction with any of the compounds that can form a cycloalkyl group. The compound of formula (XXIV) (where X is Cl, Br or I, and R 11 (where is C1-C6 alkyl) is a compound of formula (XX) (R) in a suitable solvent such as dichloromethane, chloroform, tetrahydrofuran or acetonitrile. 11 C 1-6 It can be synthesized by the reaction of an alkyl group with a halogenating agent such as N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, or bromine. These transformations are shown in Scheme 8. [ka] Scheme 8

[0142] Alternatively, the compound of formula (I) can be synthesized by reacting the compound of formula (XXV) (wherein X is Cl, Br, or I) with the amine of formula (IX) 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 (XXV) (wherein X is Cl, Br, or I) can be synthesized 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, with the compound of formula (III) (wherein R 6 These are, independently of each other, hydrogen and C 1-6 Alkyl or two R 6 together become C 3-8 Compounds of formula (XXVI) (where X is independently Cl, Br, or I) can be prepared through Suzuki cross-coupling with a cycloalkyl group (which can form a cycloalkyl group). These transformations are shown in Scheme 9. [ka] Scheme 9

[0143] Compound of formula (XXIII) (wherein R 11 C 1-6 (It is alkyl) is found in polar organic solvents such as dimethyl sulfoxide, N-methylpyrrolidine, or N,N-dimethylformamide, in the presence of a base such as Na2CO3 or K2CO3, forming a compound of formula (XXVII) (where X is Cl, Br, or I, and R 11 C 1-6 It is alkyl, R 10The compounds of formula (XXVIII) can be synthesized by the reaction of an alkyne of formula (XXVIII) with a (aryl)sulfonyl, (hetero)arylsulfonyl, or sulfonic acid group, such as a sulfonic acid, tosylate, or 2,4,6-trimethylbenzenesulfonyl group. Compounds of formula (XXVIII) are commercially available or can be readily prepared by those skilled in the art according to the methods described. Compounds of formula (XXVII) (where X is Cl, Br, or I, and R) 11 C 1-6 It is alkyl, R 10 (wherein X is Cl, Br or I, and R is R) is a compound of formula (XXIX) in a polar aprotic solvent such as dimethyl sulfoxide, N-methylpyrrolidine or N,N-dimethylformamide. 11 C 1-6 Compound (R) of formula (XIX) (which is alkyl) 10 These compounds can be formed by reacting them with (aryl)sulfonyl, (hetero)arylsulfonyl, or sulfonic acid groups (e.g., sulfonic acid, tosylate, or 2,4,6-trimethylbenzenesulfonyl group). Compounds of formula (XXIX) are commercially available or can be prepared by methods known to those skilled in the art. These transformations are shown in Scheme 10. [ka] Scheme 10

[0144] Instead, the compound of formula (I) is used in the peptide coupling transformation with the compound of formula (XXX) and formula (XXXI)(X) using the above conditions. 2Compounds of formula (XXXI) can be prepared by reaction with compounds of formula (I) (where R is OH). Compounds of formula (XXXI) are prepared in a suitable solvent such as dimethylformamide, dioxane, tetrahydrofuran, ethanol, or water, in the presence of a base such as Cs2CO3, K2CO3, or NaOtBu, and 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, by reaction with compound of formula (II) and compound of formula (XXII) (where R is OH). 6 These are, independently of each other, hydrogen and C 1-6 Alkyl or two R 6 together become C 3-8 It can be prepared via Suzuki cross-coupling of a compound of formula (XXXII) (wherein R is one of the compounds that can form a cycloalkyl group). 6 These are, independently of each other, hydrogen and C 1-6 Alkyl or two R 6 together become C 3-8 These (which can form cycloalkyl groups) are prepared by known methods or are commercially available. These conversions are shown in Scheme 11. [ka] Scheme 11

[0145] The compound of formula (Ib) (where Z is S) can be prepared by the reaction of the compound of formula (I) (where Z is O) with phosphorus pentasulfide or Lawson's reagent (CAS: 19172-47-5) in a suitable solvent such as toluene, xylene, or dichloromethane. This transformation is shown in Scheme 12. [ka] Scheme 12

[0146] Instead, the compound of formula (Ib) (where Z is S) is the compound of formula (XXXb) and the compound of formula (XXXI) (X) in the peptide coupling transformation using the above conditions. 2 The compound of formula (XXXb) can be prepared by reaction with (OH). The compound of formula (XXXb) can be prepared by reacting the compound of formula (XXX) with phosphorus pentasulfide or Lawson's reagent (CAS: 19172-47-5) in a suitable solvent such as toluene, xylene, or dichloromethane. This transformation is shown in Scheme 13. [ka] Scheme 13

[0147] 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 to those skilled in the art.

[0148] When the term "compound / multiple compounds according to the present invention" is used, it refers to the compound according to the present invention.

[0149] 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.

[0150] The compounds according to the present invention can be converted to other compounds according to the present invention in a manner known by means of 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.

[0151] Depending on the selection of suitable reaction conditions and starting materials in each case, for example, only one substituent may be substituted with another substituent according to the present invention in one reaction step, or multiple substituents may be substituted with other substituents according to the present invention in the same reaction step.

[0152] 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.

[0153] Salts of the compounds according to the present invention can be converted to the free compounds by conventional methods, acid addition salts can be converted, for example, by treatment with a suitable basic compound or a suitable ion exchange reagent, and salts with a base can be converted, for example, by treatment with a suitable acid or a suitable ion exchange reagent.

[0154] 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, such as other acid addition salts, by treatment in a suitable solvent (for example, an inorganic salt that forms silver chloride insoluble therein and therefore precipitates from the reaction mixture), for example, by treatment of a suitable metal salt of the acid, such as a sodium, barium, or silver salt of the acid, or a salt of an inorganic acid, such as a hydrochloride of silver acetate.

[0155] Depending on the procedure or reaction conditions, the compounds according to the present invention that have salt-forming properties can be obtained in free form or in salt form.

[0156] In each case, the compounds of the present invention in free or salt form, and optionally their tautomers, may exist in one form of possible stereoisomers or as mixtures thereof, depending on the number, absolute and relative configuration of chiral carbon atoms present in the molecule and / or the configuration of non-aromatic double bonds present in the molecule, in the form of pure isomers such as anticellar and / or diastereomers, or as enantiomer mixtures such as racemic compounds, diastereomer mixtures, or racemic compound mixtures. The present invention relates to pure stereoisomers and to all possible stereoisomer mixtures, and in either case, where stereochemical details are not specifically described, the above and below of this specification should be understood in this sense.

[0157] Depending on which starting materials and procedure are selected, the diastereomer mixtures or racemic compounds of the compounds according to the present invention, in free or salt form, can be obtained and separated into pure diastereomers or racemic compounds based on physicochemical differences of the components by known methods, for example, fractional crystallization, distillation and / or chromatography.

[0158] Enantiomer mixtures such as racemates, which can be obtained by similar methods, can be separated into optical counterparts by known methods, for example by recrystallization from an optically active solvent, by chromatography on a chiral adsorbent, for example by using suitable microorganisms, by high-performance liquid chromatography (HPLC) on acetylcellulose, by cleavage with a specific immobilized enzyme or conversion to a diastereomer salt, for example by using a chiral crown ether, where only one enantiomer is complexed, for example by the formation of an inclusion compound, for example, by reacting the racemate, which is a basic final product, with an optically active acid, for example by a carboxylic acid, for example by camphor, tartaric acid or malic acid or a sulfonic acid, for example by camphorsulfonic acid, and the diastereomer mixture thus obtained can be separated, for example by fractional crystallization based on their different solubility to obtain diastereomers (from which the desired enantiomer can be released by the action of a suitable reagent, for example a basic reagent).

[0159] Pure diastereomers or enantiomers can be obtained not only by separating suitable stereoisomer mixtures, but also by generally known methods of diastereoselective or enantioselective synthesis, for example, by carrying out the process according to the present invention using suitable stereochemical starting materials.

[0160] N-oxides can be prepared by reacting the compounds according to the present invention with a suitable oxidizing agent, such as an H2O2 / urea adduct, in the presence of an acid anhydride, such as trifluoroacetic anhydride. Such oxidation is known from the literature, e.g., J.Med.Chem., 32(12), 2561-73, 1989 or International Publication No. 00 / 15615.

[0161] When individual components possess different biological activities, it is advantageous to isolate or synthesize the biologically more effective stereoisomers in each case, such as enantiomers or diastereomers, or stereoisomer mixtures, such as enantiomer mixtures or diastereomer mixtures.

[0162] The compounds according to the present invention and optionally their tautomers may each 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.

[0163] The following examples illustrate, but are not limiting, the present invention.

[0164] The present invention also provides intermediates useful for preparing the compounds according to the present invention.

[0165] The following intermediates form further embodiments of the present invention.

[0166] Formula (XI) [ka] (In the formula, Z is O or S, preferably Z is O) R 1a , R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Independently selected from alkyl groups, preferably R 1a , R 1b and R 1c It 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 The condition is that, R 2 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Independently selected from alkylcarbonyls, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6Each alkylcarbonyl group may be optionally substituted with one substituent independently selected from halogen, hydroxyl, and CN, preferably R 2 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxycarbonyl and C 1-6 Selected independently of alkoxy, but with at least two R 2 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 3-6 Cycloalkyl, 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 3-6 Cycloalkyl, 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 substituent independently selected from halogen, hydroxyl, and CN, preferably R 3 It is hydrogen, R 4 C 1-6 Alkyl, C1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, 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. A 3 and R 4(Together, they arbitrarily form a ring, preferably a 5-8 membered heterocycle, more preferably a 6-membered heterocycle.) A compound of the same, or its salt or N-oxide.

[0167] The compounds of formula (I) as defined in this invention may be used, for example, as active ingredients for controlling plant pathogens, or as non-living substances for controlling potentially harmful microorganisms or organisms to humans in the agricultural sector and related fields of use. Novel compounds are distinguished by their excellent activity at low application rates, the sufficient tolerance exhibited by plants, and their environmental safety. They possess highly useful curative, preventive, and systemic properties and can be used to protect many cultivated plants. The compounds of formula (I) as defined in this invention may also be used to suppress or eradicate pathogens appearing on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of different crops of useful plants, while simultaneously protecting those parts of the plant that will grow later from plant pathogenic microorganisms.

[0168] Compounds of formula (I) as defined herein 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 “fungicidal effective amount” means an amount of a compound or combination of such compounds that is capable of producing an effect on the growth of fungi. Controlling or modifying effects include all deviations from natural occurrence, such as death or delay, and prevention includes the formation of barriers or other defenses in or on plants to prevent fungal infection.

[0169] For protection against fungal infections and plant pathogenic fungi in the soil, the compound of formula (I) as defined in this invention may also be used as a coating agent for treating plant propagation materials, such as seeds, tubers, or grains of fruits, or plant cuttings (e.g., rice). The propagation material may be treated with a composition containing the compound of formula (I) as defined in this invention before planting. For example, seeds may be coated before sowing. The compound of formula (I) as defined in this invention may also be applied (coated) to grains by impregnating the seeds in a liquid formulation or by coating the seeds with a solid formulation. The composition may also be applied to the planting site when the propagation material is planted, for example, in the sowing furrow during sowing. This invention also relates to such methods for treating plant propagation materials and to plant propagation materials thus treated.

[0170] Furthermore, the compounds of formula (I) as defined in the present invention may be used to control fungi in related fields, such as the protection of industrial materials including wood and wood-related industrial products, food storage, and hygiene management.

[0171] In addition, the present invention can also be used to protect non-biological materials, such as sawn timber, wall coverings, and paints, from fungal attacks.

[0172] The compounds of formula (I) as defined in this invention and fungicidal compositions containing them can be used to control plant diseases caused by broad-spectrum fungal plant pathogens. They are effective in controlling broad-spectrum plant diseases such as leaf pathogens of ornamental plants, turfgrasses, vegetables, fields, grains, and fruit crops.

[0173] Examples of disease-causing fungi and fungal vectors, as well as plant pathogenic bacteria and viruses, include the following: This includes species such as Absidia corymbifera, Alternaria spp., Aphanomyces spp., Ascochyta spp., Aspergillus spp. (A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus), Aureobasidium spp. (A. pullulans), Blastomyces dermatidis, Blumeria graminis, and Bremia lactucae. Botryosphaeria spp. such as B. lactucae, B. dothidea, B. obtusa; Botrytis spp. such as B. cinerea; Candida spp. such as C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis; Cephaloascus fragrans; Ceratocystis Cercospora spp. (including C. arachidicola), Cercosporidium personatum, Cladosporium spp., Claviceps purpurea, Coccidioides immitis, Cochliobolus spp., Colletotrichum spp. such as C. musae, Cryptococcus neoformans, Diaporthe spp., Didymella spp., Drecxlera spp., Elsinoe spp. Epidermophyton spp., Erwinia amylovora, Erysiphe spp. such as 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. * seditiosum), Microdochium nivale, Microsporum spp, Monilinia spp, Mucor spp, M. graminicola, M. pomi (M.Mycosphaerella species (such as pomi), Oncobasidium theobromaeon, Ophiostoma piceae, Paracoccidioides spp., Penicillium spp. such as P. digitatum and P. italicum, Petriellidium spp., Peronosclerospora spp. such as P. maydis, P. philippinensis and P. sorghi, Peronospora species (Peronospora Phytophthora spp. such as Phaeosphaeria nodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp., Phoma spp., Phomopsis viticola, P. infestans, Plasmopara spp. such as P. halstedii, P. viticola, Pleospora spp., and Podosphaera spp. such as P. leucotricha. (spp.), Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas species (spp.), P. cubensis, P. humli (P.Pseudoperonospora species (such as Pseudoperonospora humuli), Pseudopeziza tracheiphila, P. hordei, P. recondita, P. striiformis, P. triticina, and other Puccinia species (Puccinia spp.), Pyrenopeziza species (Pyrenopeziza spp.), Pyrenophora species (Pyrenopeziza spp.), Pyrenophora species (Pyrenopeziza spp.), Pyricularia species (such as P. oryzae), Pythium species (such as P. ultimum), Ramularia species (Ramularia spp.), and Rhizoctonia species (Rhizoctonia). This includes species such as Rhizomucor pusillus, Rhizopus arrhizus, Rhynchosporium spp., S. apiospermum and S. prolificans, and other species of Scedosporium spp., as well as Schizothyrium pomi. Sclerotinia spp., Sclerotium spp., Septoria spp. (including S. nodorum and S. tritici), Sphaerotheca macularis, Sphaerotheca fusca (Sphaerothorix fuliginea), Sporothorix spp., Stagonospora nodorum, Stemphylium spp., Stereum hirsutum, Thanatephorus cucumeris Trichoderma species such as *Trichoderma cucumeris*, *Tielaviopsis basicola*, *Tilletia* spp., *T. harzianum*, *T. pseudokoningii*, and *T. viride*, Trichophyton spp., Typhula spp., Uncinula necator, Urocystis spp., Ustilago spp., Venturia spp. including V. inaequalis, Verticillium spp., and Xanthomonas spp..

[0174] In particular, the compounds of formula (I) as defined in the present invention and fungicidal compositions containing them may be used to control plant diseases caused by broad-spectrum fungal plant pathogens in basidiomycetes, ascomycetes, oomycetes and / or deuteromycetes, blasocladiomycetes, chytridiomycetes, glomeromycetes and / or mucoromycetes. More specifically, the compounds of formula (I) as defined in the present invention may be used to control oomycetes.

[0175] 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;Diseases caused by Peronosporales, such as Peronospora destructor, Peronospora parasitica, Plasmopara viticola, Plasmopara halstedii, Pseudoperonospora cubensis, Albugo candida, Sclerophthora macrospora, and Bremia lactucae, as well as Aphanomyces cochlioides, Labyrinthula zosterae, and Peronosclerospora sorghii Oomycetes, including *Sorghi* and others such as *Sclerospora graminicola*. Ascomycetes, including the following, are susceptible to spotting, leaf spot, blast, canker, and / or rot, such as the Pleosporales order, such as Stemphylium solani, Stagonospora tainanensis, Spirocaea oleaginea, Setosphaeria turcica, Pyrenochaeta lycoperisici, Pleospora herbarum, Phoma destructiva, Phaeosphaeria herpotrichoides, and Phaeocryptocus gaeumannii. Ophiosphaerella graminicola, Ophiobolus graminis, Leptosphaeria maculans, Hendersonia creberrima, Helminthosporium triticirepentis, Setosphaeria turcica, Drechslera glycines, Didymella bryoniae, Cycloconium oleagineum, Corynespora cassiicola, Cochliobolus satibus Pyrenophora sativus, Bipolaris cactivora, Venturia inaequalis, Pyrenophora teres, Pyrenophora triticisi-lepentisCercosporella species include *Trici-repentis*, *Alternaria alternata*, *Alternaria brassicola*, *Alternaria solani*, and *Alternaria tomatophila*, as well as other species in the Capnodiales order, such as *Septoria tritici*, *Septoria nodorum*, *Septoria glycines*, *Cercospora arachidicola*, *Cercospora sojina*, *Cercospora zeae-maydis*, and *Cercosporella capsuleae*. This includes species such as capsellae and Cercosporella herpotrichoides, Cladosporium carpophilum, Cladosporium effusum, Passalora fulva, Cladosporium oxysporum, Dothistroma septosporum, Isariopsis clavispora, Mycosphaerella fijiensis, Mycosphaerella graminicola, and Mycovellosiella coepkeii. Pseudocercosporella koepkeii, Phaeoisariopsis bataticola, Pseudocercospora vitis, Pseudocercosporella herpotrichoidesHerpotrichoides), Ramularia beticola, Ramularia collo-cygni, etc. Magnaporthales, for example Gaeumannomyces graminis, Magnaporthe grisea, Pyricularia oryzae, etc. Diaporthales, for example Anisogramma anomala, Apiognomonia errabunda, Cytospora platani, Diaporthe phaseolorum, Discula destructiva, Gnomonia fructicola fructicola), Greeneria uvicola, Melanconium juglandinum, Phomopsis viticola, Sirococcus clavigignenti-juglandacearum, Tubakia dryina, Dicarpella spp., Valsa ceratosperma, and others, such as Actinothyrium graminis, Ascochyta pisi, Aspergillus flavus, Aspergillus fumigatus Candida species (fumigatus), Aspergillus nidulans, Asperisporium caricae, Blumerierella jaapii, Candidaspp.), Capnodium ramosum, Cephaloascus spp., Cephalosporium gramineum, Ceratocystis paradoxa, Chaetomium spp., Hymenoscyphus pseudoalbidus, Coccidioides spp., Cylindrosporium padi, Diplocarpon malae, Drepanopeziza campestris, Elsinoe ampelina, Epicoccum nigram nigrum), Epidermophyton spp., Eutypa lata, Geotrichum candidum, Gibellina cerealis, Gloeocercospora sorghi, Gloeodes pomigena, Gloeosporium perennans; Gloeotinia temulenta, Griphospaeria corticola, Kabatiella lini, Leptographium microsporum, Leptosphaerulinia crassica crassiasca), Lophodermium seditiosum, Marssonina graminicola, Microdochium nivale, Monilinia fructicolafructicola, Monographella albescens, Monosporascus cannonballus, Naemacyclus spp., Ophiostomanovo-ulmi, Paracoccidioides brasiliensis, Penicillium expansum, Pestalotia rhododendri, Petriellidium spp., Pezicula spp., Phialophora gregata, Phyllachora pomigena pomigena), Phymatotrichum omnivora, Physalospora abdita, Plectosporium tabacinum, Polyscytalum pustulans, Pseudopeziza medicaginis, Pyrenopeziza brassicae, Ramulispora sorghi, Rhabdocline pseudotsugae, Rhynchosporium secalis, Sacrocladium oryzae, Scedosporium species Sclerotium spp.), Schizothyrium pomi, Sclerotinia sclerotiorum, Sclerotinia minor; Sclerotium spp., Typhula ishikariensisishikariensis), Seimatosporium mariae, Lepteutypa cupressi, Septocyta ruborum, Sphaceloma perseae, Sporonema phacidioides, Stigmina palmivora, Tapesia jarunde (T Powdery mildew, such as that caused by Apesia yallundae, Taphrina bullata, Thielviopsis basicola, Trichoseptoria fructigena, Zygophiala jamaicensis, etc.; Erysiphales, such as Blumeria graminis, Erysiphe polygoni, Uncinula necator, Sphaerotheca fuligena, Podosphaera leucotricha, Podospaera maculalis Caused by plants such as *Pterococcus macularis*, *Golovinomyces cichoracearum*, *Leveillula taurica*, *Microsphaera diffusa*, *Oidiopsis gossypii*, *Phyllactinia guttata*, and *Oidium arachidis*;Caused by fungi, such as those of the Botryosphaeriales order, including Dothiorella aromatica, Diplodia seriata, Guignardia bidwellii, Botrytis cinerea, Botryotinia allii, Botryotinia fabae, Fusicoccum amygdali, Lasiodiplodia theobromae, Macrophoma theicola, Macrophomina phaseolina, and Phyllosticta cucurbitacearum;Anthracnose, for example, caused by the genus Glommerelales, such as Colletotrichum gloeosporioides, Colletotrichum lagenarium, Colletotrichum gossypii, Glomerella cingulata, and Colletotrichum graminicola, and wilt or canker, for example, the order Hypocreales, such as Acremonium strictum, Claviceps purpurea, Fusarium culmorum, and Fusarium graminicola. *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* Caused by plants such as *Trichothecium roseum* and *Verticillium theobromae* (viride). The Basidiomycete class includes the following: smut, caused by species such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, and Ustilago zeae (all belonging to the Ustilaginales order); rust, caused by species such as Cerotelium fici, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, and Puccinia graminis. Puccinia graminis), Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia striiformis f.sp. Hordei, Puccinia striiformis f.sp. cecalisPucciniales (including Secalis), Pucciniastrum coryli, Cronartium ribicola, Gymnosporangium juniperi-viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor, and Uromyces viciae-fabee. This includes diseases caused by Uredinales, such as viciae-fabae, as well as other rot and disease, such as Cryptococcus spp., Exobasidium vexans, Marasmiellus inoderma, and Mycena spp.), Sphacelotheca reiliana, Typhula ishikariensis, Urocystis agropyri, Itersonilia perplexans, Corticium invisum, Laetisaria fuciformis, Waitea circinata, Rhizoctonia solani, Thanetephorus cucurmeris, Entyloma dahliae, Entylomella microspora, Neovossia molliniae This includes those caused by *Tilletia moliniae* and *Tilletia caries*. Blastocladiomycetes, such as Physoderma maydis. Mucoromycete species such as Choanephora cucurbitarum, Mucor spp., and Rhizopus arrhizus, as well as Diseases caused by other species and genera closely related to those listed above.

[0176] In addition to their fungicidal activity, compositions comprising the present compound and the compound of formula (I) as defined herein may also have activity against bacteria such as Erwinia amylovora, Erwinia caratovora, Xanthomonas campestris, Pseudomonas syringae, Streptomyces scabies and other related species, as well as certain protozoa.

[0177] Within the scope of the present invention, the protected target crops and / or useful plants are typically berry plants, e.g., blackberries, blueberries, cranberries, raspberries and strawberries; cereals, e.g., barley, corn, millet, oats, rice, rye, sorghum, rye and wheat; fiber plants, e.g., cotton, flax, hemp, jute and sisal; crops, e.g., sugar and fodder beets, coffee, hops, mustard, rapeseed (canola), poppies, sugarcane, sunflowers, tea and tobacco; fruit trees, e.g., apples, apricots, avocados, bananas, cherries, citrus fruits, nectarines, peaches, pears and plums; grasses, e.g., Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St. Augustine grass and zoysia grass Herbs, such as basil, borage, chives, coriander, lavender, lavender, mint, oregano, parsley, rosemary, sage, and thyme; legumes, such as kidney beans, lentils, peas, and soybeans; nuts, such as almonds, cashews, peanuts, hazelnuts, peanuts, pecans, pistachios, and walnuts; palms, such as oil palms; ornamental plants, such as flowers, shrubs, and trees; other trees, such as cocoa, coconuts, olives, and rubber trees; vegetables, such as asparagus, eggplant, broccoli, cabbage, carrots, cucumbers, garlic, lettuce, mallow, melon, okra, onions, peppers, potatoes, pumpkins, rhubarb, spinach, and tomatoes, as well as climbing plants, including perennial and annual crops such as grapes.

[0178] Useful plants and / or target crops according to the present invention include conventional varieties such as insect-resistant (e.g., Bt. and VIP varieties), disease-resistant, herbicide-resistant (e.g., glyphosate and glufosinate-resistant maize varieties, commercially available under trade names RoundupReady® and LibertyLink®), and nematode-resistant varieties, as well as genetically enhanced or genetically modified varieties. Examples of suitably genetically enhanced or genetically modified varieties include the Stoneville 5599BR cotton and Stoneville 4892BR cotton varieties.

[0179] It should be understood that the terms “useful plants” and / or “target crops” also include useful plants that have been conferred resistance to herbicides such as bromoxynil or certain classes of herbicides (e.g., HPPD inhibitors, ALS inhibitors, e.g., primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovir-sikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors, or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional breeding methods or genetic engineering. An example of a crop conferred resistance to imidazolinones, e.g., imazamox, by conventional breeding methods (mutation) is Clearfield® summer rapeseed (canola). Examples of crops that have been genetically modified to be resistant to herbicides or a certain class of herbicides include glyphosate- and glufosinate-resistant maize varieties that are commercially available under the trade names RoundupReady®, Herculex I®, and LibertyLink®.

[0180] 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, which can, for example, synthesize one or more selectively acting toxins, such as those known from toxin-producing bacteria. Examples of toxins that can be expressed include δ-endotoxin, vegetative insecticidal proteins (Vip), insecticidal proteins from nematode-symbiotic bacteria, and toxins produced by scorpions, arachnids, wasps, and fungi. An example of a crop modified to express Bacillus thuringiensis toxin is Bt maize KnockOut® (Syngenta Seeds). An example of a crop containing two or more genes encoding insecticidal resistance and therefore expressing two or more toxins is VipCot® (Syngenta Seeds). Crops or their seed materials may possess resistance to multiple pests (so-called superimposed transgenic events resulting from genetic modification). For example, a plant, such as Herculex I® (Dow AgroSciences, Pioneer Hi-Bred International), may be both herbicide-resistant and capable of expressing insecticidal proteins.

[0181] It should be understood that the terms “useful plants” and / or “target crops” 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.

[0182] 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 from species such as Photorhabdus luminescens, Xenorhabdus nematophilus, etc., such as Photorhabdus spp. or Xenorhabdus Insecticidal proteins of nematode-symbiotic bacteria such as spp.; toxins produced by animals such as scorpion venom, spider venom, large wasp (wasp) venom and other insect-specific neurotoxins; toxins produced by fungi such as Streptomycete venom, 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, maize-RIP, Examples include ribosomal inactivating proteins (RIPs) such as 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 channel blockers; juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase, and glucanase.

[0183] Furthermore, it should be understood that in connection with the present invention, there exist δ-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or plant insecticidal proteins (Vip), such as Vip1, Vip2, Vip3, or Vip3A, as well as explicitly hybrid toxins, cleavage toxins, and modified toxins. Hybrid toxins are recombinantly produced by 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 naturally occurring toxins are substituted. In such amino acid substitutions, a protease recognition sequence that is not naturally present is preferably inserted into the toxin, for example, in the case of Cry3A055, and a cathepsin-G recognition sequence is inserted into the Cry3A toxin (see International Publication No. 03 / 018810).

[0184] 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.

[0185] The processes for preparing such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparations are known, for example, from International Publication No. 95 / 34656, European Patent Application Publication No. 0367474, European Patent Application Publication No. 0401979, and International Publication No. 90 / 13651.

[0186] The toxins contained in transgenic plants confer resistance to harmful insects. Such insects can exist in any insect taxonomy, but are commonly found in beetles (Coleoptera), diptera, and butterflies (Lepidoptera).

[0187] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known, and some of them are commercially available. Examples of such plants include: YieldGard® (maize variety expressing Cry1Ab toxin); YieldGard Rootworm® (maize variety expressing Cry3Bb1 toxin); YieldGard Plus® (maize variety expressing Cry1Ab and Cry3Bb1 toxins); Starlink® (maize variety expressing Cry9C toxin); Herculex I® (maize variety expressing Cry1Fa2 toxin and the enzyme phosphinothrysin N-acetyltransferase (PAT) to achieve resistance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety expressing Cry1Ac toxin); Bollgard I® (cotton variety expressing Cry1Ac toxin); Bollgard These include II (registered trademark) (cotton varieties expressing Cry1Ac and Cry2Ab toxins); VipCot (registered trademark) (cotton varieties expressing Vip3A and Cry1Ab toxins); NewLeaf (registered trademark) (potato varieties expressing Cry3A toxin); NatureGard (registered trademark), Agrisure (registered trademark) GT Advantage (GA21 glyphosate resistance trait), Agrisure (registered trademark) CB Advantage (Bt11 corn borer (CB) trait), and Protecta (registered trademark).

[0188] Further examples of such transgenic crops include: 1. Bt11 maize, Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31, 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize (Zea mays) conferring resistance to attacks by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of cleavage-type Cry1Ab toxin. Bt11 maize has also acquired resistance to the herbicide glufosinate ammonium by transgenic expression of the enzyme PAT. 2. Bt176 maize, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize (Zea mays) conferred resistance to attacks by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of Cry1Ab toxin. Bt176 maize has also acquired resistance to the herbicide glufosinate ammonium by transgenic expression of the enzyme PAT. 3. MIR604 maize, Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Maize conferred insect resistance by transgenic expression of modified Cry3A toxin. This toxin is Cry3A055, modified by insertion of a cathepsin-G protease recognition sequence. Preparation of such transgenic maize plants is described in International Publication No. 03 / 018810. 4. MON 863 maize, manufactured by Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON863 expresses the Cry3Bb1 toxin and is resistant to certain Coleoptera insects. 5. IPC 531 cotton, manufactured by Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02. 6.1507 Maize, manufactured by Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Genetically modified maize for the expression of the protein Cry1F to acquire resistance to certain Lepidoptera insects and the PAT protein to acquire resistance to the herbicide glufosinate ammonium. 7. NK603 X MON810 maize, manufactured by Monsanto Europe, SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. This is a conventional hybrid maize variety resulting from the cross between the genetically modified varieties NK603 and MON 810. NK603 X MON 810 maize transgenically expresses the protein CP4 EPSPS, obtained from the Agrobacterium sp. strain CP4, which confers resistance to the herbicide Roundup® (which contains glyphosate), and the Cry1Ab toxin, obtained from Bacillus thuringiensis subsp. kurstaki, which provides resistance to certain Lepidoptera, including the European corn borer.

[0189] As used herein, the term “habitat” means cultivated land where plants grow or where the seeds of cultivated plants are sown or where seeds will be planted in the soil. It includes soil, seeds and seedlings, and established vegetation.

[0190] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves, and fruits.

[0191] The term “plant propagation material” is understood to refer to plant reproductive parts such as seeds and plant materials such 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 after sprouting 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.

[0192] The pesticides referred to herein by their common names are publicly known, for example, from "The Pesticide Manual," 19th Ed., British Crop Protection Council 2021.

[0193] The compounds of formula (I) as defined in this invention may be used in their unmodified form or, preferably, in combination with auxiliaries conventionally used in the art of formulation. For this purpose, they may be appropriately formulated in known methods into emulsifiable concentrates, coating pastes, ready-to-spray or dilutable solutions or suspensions, diluted emulsions, wettable powders, soluble powders, powders for spraying, granules, and also, for example, encapsulations in polymeric substances. As with the type of composition, the method of application, such as spraying, misting, powdering, granulation, coating, or pouring, may be selected according to the intended purpose and the circumstances at hand. The composition may also contain further auxiliaries such as stabilizers, defoamers, viscosity modifiers, binders, or tackifiers, as well as fertilizers, micronutrient donors, or other formulations for obtaining special effects.

[0194] For example, suitable carriers and / or auxiliaries for agricultural applications may be solids or liquids and are substances useful in formulation techniques, such as natural or recycled inorganic substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders, or fertilizers. Such carriers are described, for example, in International Publication No. 97 / 33890.

[0195] 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 usually 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.

[0196] 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.

[0197] Emulsifying concentrates are homogeneous liquid compositions that are dispersible in water or other liquids, and may consist solely of the active compound and a liquid or solid emulsifier, or they may also contain liquid carriers such as xylene, high-boiling aromatic naphtha, isophorone, and other non-volatile organic solvents. When used, these concentrates are dispersed in water or other liquids and are typically applied as a spray to the area to be treated. The amount of the active ingredient may range from 0.5% to 95% of the concentrate.

[0198] Granular formulations include both extruded and relatively coarse particles and are typically applied undiluted to the area requiring treatment. Typical carriers for granular formulations include sand, fuller's soil, attapulgite clay, bentonite clay, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, gypsum, wood flour, crushed corn cobs, crushed peanut shells, sugar, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate, and other organic or inorganic materials that can absorb or be coated with the active compound. Granular formulations typically contain 5% to 25% active ingredients, which may include surfactants such as heavy aromatic naphtha, kerosene, and other petroleum fractions, or stickers such as vegetable oils and / or dextrin, glue, or synthetic resins.

[0199] Powder for scattering is a free-flowing mixture of an active ingredient and finely ground solids such as talc, clay, powder, and other organic and inorganic solids that act as a dispersant and carrier.

[0200] 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.

[0201] 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.

[0202] Suitable agricultural additives and / or carriers useful for formulating the composition of the present invention in the above formulation types are well known to those skilled in the art.

[0203] Examples of liquid carriers that can be used include water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetate, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidinone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-Trichloroethane, 2-Heptanone, Alpha-pinene, d-Limonene, Ethylene glycol, Ethylene glycol butyl ether, Ethylene glycol methyl ether, γ-Butyrolactone, Glycerol, Glycerol diacetate, Glycerol monoacetate, Glycerol triacetate, Hexadecane, Hexylene glycol, Isoamyl acetate, Isobornyl acetate, Isooctane, Isophorone, Isopropylbenzene, Isopropyl myristate, Lactic acid, Laurylamine, Mesityl oxide, Methoxypropanol, Methyl isoamyl ketone, Methyl isobutyl ketone, Methyl laurate, Methyl octanoate, Methyl oleate, Methylene chloride, m-Xylene, n-Hexane, n-Octylamine, Octadeca Examples include nic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol and amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol and other high molecular weight alcohols, ethylene glycol, propylene glycol, glycerin and N-methyl-2-pyrrolidinone. Water is generally a preferred carrier for diluting concentrates.

[0204] Suitable solid carriers include, for example, talc, titanium dioxide, pyroferrite clay, silica, attapulgite clay, diatomaceous earth (kieselguhr), white pigment, diatomaceous earth (diatomaxeous earth), lime, calcium carbonate, bentonite clay, fuller's earth, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, and lignin.

[0205] A wide range of surfactants are advantageously used in both 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 have anionic, cationic, nonionic, or polymeric properties and may be used as emulsifiers, wetting agents, suspending agents, or for other purposes. Typical surfactants include alkyl sulfate salts, e.g., diethanolammonium lauryl sulfate; alkylaryl sulfonate salts, 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.

[0206] 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.

[0207] 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 formulated together with the composition of the present invention or mixed, for example, in a spray tank. These further biocides may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides, plant growth regulators and / or biological formulations.

[0208] The following combinations of the compound of formula I and another active substance in a 1:1 weight ratio are preferred (where the abbreviation "TX" means "one compound selected from the compounds defined in Tables 1.1 to 1.45 and Table A"): (7E,9Z)-Dodeca-7,9-Diene-1-Ilacetate+TX, (9Z,11E)-Tetradeca-9,11-Diene-1-Ilacetate+TX, (9Z,12E)-Tetradeca-9,12-Diene-1-Ilacetate+TX, (E)-6-Methylhepto-2-Ene-4-ol+TX, (E)-Dec-5-Ene-1-Ilacetate and (E)-Dec-5-Ene-1-ol+TX, (E)-Tridec-4-Ene-1-Ilacetate+TX, (E,Z)-Tetradeca-4,10-Diene-1-I Luacetate + TX, (Z)-Dodec-7-en-1-Illacetate + TX, (Z)-Hexadec-11-en-1-Illacetate + TX, (Z)-Hexadec-11-enal + TX, (Z)-Hexadec-13-en-11-in-1-Illacetate + TX, (Z)-Ikos-13-en-10-on + TX, (Z)-Tetradec-7-en-1-al + TX, (Z)-Tetradec-9-en-1-ol + TX, (Z)-Tetradec-9-en-1-Illacetate + TX, 1,2-Dibromo- 3-Chloropropane + TX, 1,2-Dichloropropane + TX, 1,2-Dichloropropane and 1,3-Dichloropropene + TX, 1,3-Dichloropropene + TX, 14-Methyloctadec-1-ene + TX, 1-H-Pyridine-2-Thione + TX, 2-(Octylthio)ethanol + TX, 2-Chlorophenyl N-methylcarbamate (CPMC) + TX, 3-(4-Chlorophenyl)-5-Methylrhodanine + TX, 3,4-Dichlorotetrahydrothiophene 1,1-Dioxide + TX, 4-(Quinoxaline-2-ylamino)benzenesulfonamide + TX, 4-methylnonan-5-ol and 4-methylnonan-5-one + TX, 5-methyl-6-thioxo-1,3,5-thiadiadinane-3-ylacetate + TX, 6-isopentenylaminopurine + TX, 8-hydroxyquinoline sulfate + TX, abamectin + TX, acequinosyl + TX, acetamiprid + TX, acetoprol + TX, acrinatrin + TX, acinonapir + TX, Adoxophyes orana GV + TX, afidopiropen + 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, Anaprapha 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+TX, Bacillus chitinosporus AQ746 (NRRL accession number B-21 618)+TX, Bacillus firmus+TX, Bacillus kurstaki+TX, Bacillus mycoides AQ726 (NRRL accession number B-21664)+TX, Bacillus pumilus (NRRL accession number B-30087)+TX, Bacillus pumilus Bacillus pumilus AQ717 (NRRL accession number B-21662) + TX, Bacillus sp. AQ175 (ATCC accession number 55608) + TX, Bacillus sp. AQ177 (ATCC accession number 55609) + TX, Bacillus sp. AQ178 (ATCC accession number 53522) + TX, Bacillus sphaericus Neide + TX, Bacillus subtilis AQ153 (ATCC accession number 55614) + TX,Bacillus subtilis AQ30002 (NRRL accession number 50421) + TX, Bacillus subtilis AQ30004 (NRRL accession number B-50455) + TX, Bacillus subtilis AQ713 (NRRL accession number B-21661) + TX, Bacillus subtilis AQ743 (NRRL accession number B-21665) + TX, Bacillus subtilis (unspecified) + TX, Bacillus thuringiensis AQ52 (NRRL accession number 21619) + TX, Bacillus thuringiensis (Bacillus Bacillus thuringiensis)BD#32 (NRRL accession number 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 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, Bioalethrin + TX, Biorethmetrin + TX, Bis(tributyltin) oxide + TX, Bisagil + TX, Bistriflurone + TX, Bisulfurfen + TX, Brevicomin + TX, Broflanilide + TX, Broflutrinate + TX, Bromoacetamide + TX, Bromophos-ethyl + TX, Bronopol + TX, Busulfan + TX, Butocarboxyme + TX, Butopyronoxyl + TX, Butoxy(polypropylene glycol) + TX, Butylpyridan Ben+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. 1594626-19-3+TX, CAS No. 1594637-65-6+TX, CAS No. 1632218-00-8+TX, CAS number 1808115-49-2+TX, CAS number 1922957-46-7+TX, CAS number 1922957-48-9+TX, CAS number 1956329-03-5+TX, CAS number 1990457-52-7+TX, CAS No. 1990457-55-0+TX, CAS No. 1990457-57-2+TX, CAS No. 1990457-66-3+TX, CAS No. 1990457-77-6+TX, CAS No. 1990457-85-6+TX, CAS No. 2032403-97-5+TX, CA S number 2044701-44-0+TX, CAS number 2095470-94-1+TX, CAS number 2128706-04-5+TX, CAS number 2128706-05-6+TX, CAS number 2133042-31-4+TX, CAS number 2133042-44-9+TX, C AS 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 No. 2615135-05-0) + TX, CAS No. 2719848-60-7 + TX, CAS No. RNA (Leptinotarsa ​​decemlineata-specific recombinant double-strand interference GS2) + TX, Chlorantraniliprole + TX, Chlordan + TX, Chlorfenapyr + TX, Chloropicrin + TX, Chloroprallethrin + TX, Chlorpyrifos + TX, Chromafenozide + TX, Chrysoperla carnea carnea)+TX, clenpyrine+TX, chloetocarb+TX, clothianidin+TX, chodollerua+TX, chodolmon+TX, copper acetoarsenate+TX, copper dioctanoate+TX, copper hydroxide+TX, copper sulfate+TX, cresol+TX, clufomate+TX, Cryptolaemus montrouzieri+TX, kyurua+TX, cyanophenphos+TX, cyantraniliprole+TX, sibutrin+TX, cyclaniliprole+TX, cyclobutriflurum+TX, cycloprothrin+TX, cycloxapride+TX, Cydia pomonera Pomonella GV+TX, cyenopyrafen+TX, cyetopyrafen+TX, cyflumetofen+TX, cyfluthrin+TX, cyhalodimide+TX, cyclohalothrin+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, Diclofenthion + TX, Dichlorophene + TX, Dicliphos + TX, Dichloromezothiaz + TX, Diethyltoluamide + TX, Diflubenzuron + TX, Diglyphus isaea + TX, Dimatif + TX, Dimethoate + TX, Dimethyl carbonate + TX, Dimethyl phthalate + TX, Zinpropyridaz + TX, Dinactin + TX, Dinocap + TX, Dinotefuran + TX, Dioxabenzophos + TX,Dipirithione + TX, Disparure + TX, D-Limonene + TX, Dodec-8-en-1-ylacetate + TX, Dodec-9-en-1-ylacetate + TX, Dodeca-8,10-dien-1-ylacetate + TX, Dodecine + TX, Dominicalua + TX, Doramectin + TX, Emamectin + TX, Emamectin, Ethifen salt + TX, Empenthrin + TX, Encarsia formosa + TX, Endotar + TX, Endrin + TX, Eprinomectin + TX, Epsilon-monfluorothrin + TX, Epsilon-metofluthrin + TX, Eretmocerus eremicus + TX, Esfenvalerate + TX, Ethion + TX, Ethiprole + TX, Etoprophos + TX, Ethyl 4-methyloctanoate + TX, Ethylhexanediol + TX, Ethylenedibromide + TX, Etofenprox + TX, Ethoxazole + TX, Etopyrafen + TX, Eugenol + TX, Extracts of fermented products derived from seaweed and molasses + TX, Extracts of fermented products derived from seaweed and molasses containing urea + TX, Extracts of fermented plant products derived from seaweed + TX, Extracts of seaweed and fermented plant products containing plant hormones, vitamins, EDTA-chelated copper, zinc and iron + TX, Famfur + TX, Phenaminosulf + TX, Phenamiphos + TX, Phenazaquin + TX, Fenfluthrin + TX, Fenitrothion + TX, Fenmezodithiaz + TX, Phenobucarb + TX, Phenothiocarb + TX, Phenoxycarb + TX, Fenpropathrin + TX, Fenpyrad + TX, Fenpyroximate + TX, Fensulfothion + TX, Fenthione + TX, Fentin + TX, Fentin acetate + TX, Fenvalerate + TX, Ferric phosphate + TX, Fipronil + TX, Flomethoxine + TX, Flunicamide + 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, Flularaner+TX, Fluvalinate+TX, Fluxamethamide+TX, Formaldehyde+TX, Fostiazate+TX, Fostiethane+TX, Frontalin+TX, Furfural+TX,Gamma-cyhalotrin + TX, Gossyplure (registered trademark) (1:1 mixture of (Z,E) and (Z,Z) isomers of hexadeca-7,11-dien-1-yl acetate) + TX, Grandlua + TX, Grandlua I + TX, Grandlua II + TX, Grandlua III + TX, Grandlua IV + TX, Granulovirus + TX, Guadipyr + TX, GY-81 + TX, Halfenprox + TX, Halofenozide + TX, Harpin + TX, Helicoverpa armigera nuclear polyhedron disease virus + TX, Helicoverpa zea NPV + TX, Helicoverpa zea nuclear polyhedron disease virus + TX, Heliothis Heliothis virescens (nuclear polyhedrosis virus) + TX, Heliothis virescens (nuclear polyhedrosis virus) + TX, Hemel + TX, Hempa + TX, Heptafluthrin + TX, Heterophos + TX, Heterorhabditis bacteriophora and H. megidis + TX, Hexalua + TX, Hexamide + TX, Hexithiazox + TX, Hypodamia convergence (Condens) + TX, Hydramethylnon + TX, Hydralgafen + TX, Slaked lime + TX, Imisiaphos + TX, Imidacloprid + TX, Imiprothrin + TX, Indazapiroxamet + TX, Indoxacarb + TX, Iodomethane + TX, Iprodione + TX, Ipsdienol + TX, Ipsenol + TX, Isamidophos + TX, Isazofos + TX, Isocycloserum + TX, Isoflu Alanam (CAS number 2892524-05-7) + TX, Isothioate + TX, Ivermectin + TX, Japonilua + TX, Kappa-bifenthrin + TX, Kappa-tefluthrin + TX, Kasugamycin + TX, Kasugamycin hydrochloride hydrate + TX, Kinetin + TX, Lambda-cyhalothrin + TX, Redoprona + TX, Lepimectin + TX, Leptomastix dactylopii + TX, Lineatin + TX, Littlea + TX, Lupulua + TX,Rotilaner + TX, Lufenuron + TX, Macrolophus caliginosus + TX, Mamestra brassicae NPV + TX, Mecarfon + TX, Medrua + 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, Methyl aphorate+TX, Methyl bromide+TX, Methyl eugenol+TX, Methyl isothiocyanate+TX, Methylneodecanamide+TX, Metofluthrin+TX, Metolcarb+TX, Mexacalbate+TX, Milbemectin+TX, Milbemycin oxime+TX, Monfluorothrin+TX, Morzide+TX, Moxidectin+TX, Mascalua+TX, Muscodor albus 620 (NRRL accession number 30547)+TX, Muscodor roseus A3-5 (NRRL accession number 30548)+TX, Myrothecium vercaria Verrucaria composition + TX, Nabam + TX, NC-184 + TX, Neem tree-based products + TX, Neodiprion sertifer NPV and N. lecontei NPV + TX, Nickel bis(dimethyldithiocarbamate) + TX, Niclosamide + TX, Niclosamide-olamine + TX, Nicofluprole + TX, Nitenpyram + TX, Nichiazine + TX, Nitrapyrine + TX, Octadeca-2,13-dien-1-yl acetate + TX,Octadeca-3,13-diene-1-ylacetate + TX, Octylinone + TX, Omethoate + TX, Orfuralua + TX, Orius spp. + TX, Orictalua + TX, Ostramon + TX, Oxamate + TX, Oxamyl + TX, Oxazosulfyl + TX, Oxolinic acid + TX, Oxtetracycline + TX, Paecilomyces fumosoroseus + TX, Paecilomyces lilacinus + TX, Parathion-ethyl + TX, Pasteuria nisizawae + TX, Pasteuria penetrans + TX, Pasteuria ramosa (Pasteuria ramosa)+TX, Pasteuria thornei+TX, Pasteuria usgae+TX, P-cymene+TX, Penflurone+TX, Pentachlorophenol+TX, Permethrin+TX, Phenothrin+TX, Folate+TX, Phosphamidone+TX, Phosphocarb+TX, Phytoseiulus persimilis+TX, Picalidine+TX, Pioxaniliprole+TX, Piperazine+TX, Piperonylbutoxide+TX, Pyrimicarb+TX, Pyrimiphos-ethyl+TX, Pyrimiphos-methyl+TX, Plutella xylostella granulosis virus+TX, Plutella xylostella (Plutella Xylostella) Nuclear Polyhedra Disease Virus + TX, Polyhedrosis Virus + TX, Potassium and Molybdenum and EDTA Chelated Manganese + TX, Potassium Ethyl Xanthanate + TX, Hydroxyquinoline Sulfate Potassium + TX, Prallethrin + TX, Probenazole + TX, Profenofos + TX, Profluthrin + TX, Propargit + TX, Propetamfos + TX, Propoxur + TX, Prothiofos + TX, Protrefenbute + TX, Piflubmid + TX, Pymetrozine + TX, Piraclofos + 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, QRD420 (terpenoid blend) + TX, QRD452 (terpenoid blend) + TX, QRD460 (terpenoid blend) + TX, Quillaja saponaria + TX, Quinoclamine + TX, Quinonamide + TX, Resmethrin + TX, Rhodococcus globulus globerulus)AQ719 (NRRL accession number B-21663)+TX, sarolaner+TX, S-biorethrin+TX, cebuphos+TX, selamectin+TX, siglur+TX, silafluofen+TX, simazine+TX, sodium pentachlorophenoxide+TX, sordidine+TX, spidoxamato+TX, spinetoram+TX, spinosad+TX, spirobudifen+TX, spirodiclofen+TX, spiromesifen+TX, spirovidion+TX, spirotetramato+TX, Spodoptera exigua polycapsidoneurocyte virus+TX, Spodoptera frugiperda polycapsidoneurocyte 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 accession number 30232)+TX, Streptomyces sp. (NRRL accession number B-30145)+TX, Streptomycin+TX,Streptomycin sesquisulfate + TX, Strychnine + TX, Sulcatol + TX, Sulfiflumin (CAS number 2377084-09-6) + TX, Sulfoxaflor + TX, Tadimucarb + TX, Tebufenozide + TX, Tebufenpyrad + TX, Tebupirimifos + TX, Tecrophthalam + TX, Tefluthrin + TX, Temefos + TX, Tepa + TX, Terbam + TX, Terbufos, +TX, Terpenoid Blend +TX, Tetrachlorantraniliprole +TX, Tetrachlorothiophene +TX, Tetradec-11-en-1-yl acetate +TX, Tetradiphon +TX, Tetramethrin +TX, Tetramethylfluthrin +TX, Tetranactin +TX, Tetraniliprole +TX, Theta-cypermethrin +TX, Thiacloprid +TX, Thiafenox +TX, Thiamethoxam +TX, Thiocyclam +TX, Thiodicarb +TX, Thiofanox +TX, Thiohempa +TX, Thiomersal +TX, Ometon + TX, Thionadin + TX, Thiophanate + TX, Thiosultap + TX, Thiotepa + TX, Tigolaner + TX, Thiolantraniliprole + TX, Thioxazafen + TX, Tolfenpyrad + TX, Toxafen + TX, Tralomethrin + TX, Transfluthrin + TX, Tretamine + TX, Triazamate + TX, Triazophos + TX, Triazurone + TX, Tributyltin oxide + TX, Trichlorfon + TX, Trichloronate + TX, Trichlorfon + TX, Tricogramma species (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, Xylenol+TX, YI-5302+TX, Zeatin+TX, Zeta-cypermethrin+TX, N-[(1R)-1-benzyl-3-chloro-1-methyl-buto-3-enyl]-8-fluoroquinoline-3-carboxamide+TX, N-[(1S)-1-benzyl-3-chloro-1-methyl-buto-3-enyl]-8-fluoroquinoline-3-carboxamide+TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine (these compounds (These compounds may be prepared from 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 from the method described in International Publication No. 2017 / 220485) + TX, (4-phenoxyphenyl)methyl 2-amino-6-methylpyridine-3-carboxylate (this compound can be prepared from the method described in International Publication No. 2014 / 006945) + TX, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone + TX, (7E,9Z)-dodeca-7,9-diene-1-ylacetate + TX, (9Z,11E)-tetradeca-9,11-diene-1-ylacetate (E)-(3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, (Z)-dodec-7-en-1-ylacetate + TX, (Z)-hexadec-11-en-1-ylacetate + TX, (Z)-hexadec-11-enal + TX, (Z)-hexadec-13-en-11-in-1-ylacetate + TX, (Z)-icos-13-en-10-one + TX, (Z)-tetradec-7-en-1-al + TX, (Z)-tetradec-9-en-1-ol + TX, (Z)-tetradec-9-en-1-ylacetate + TX, (Z (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazole-3-yl]oxy-2-methoxyimino-N,3-dimethylpent-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-dimethylpent-3-enamide + TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazole-1-yl]acetyl]-4-piperidyl]thiazole- 4-yl]-4,5-dihydroisoxazole-5-yl]-3-chlorophenyl]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-methyl-pyrazolo[1,5-a]pyridine-3-yl)-4,4-difluoro-3,3-dimethylisoquinoline (these compounds may 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 and 1,3-Dichloropropene + TX, 1,3-Dichloropropene + TX, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea + TX, 1-[2-[[1-(4-chlorophenyl)pyrazole-3-yl]oxymethyl]-3-methylphenyl]-4-methyltetrazole-5-one + TX, 10-Diene-1-ylacetate + TX, 14-Methyloctadec-1-ene + TX, 1-Bromo-2-chloroethane + TX, 1-Di Chloro-1-nitroethane + TX, 1-hydroxy-1H-pyridine-2-thione + TX, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea + TX, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazole-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carb Xazamide + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(1,3-dithiolan2-yl)phenyldimethylcarbamate + TX, 2-(2-butoxyethoxy)ethylpiperonilate + TX, 2-(2-butoxyethoxy)ethylthiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenylmethylcarbamate + TX, 2-(4-chloro-3,5-xylyloxy)ethanol + TX, 2-(difluoromethyl) (Tyl)-N-(3-ethyl-1,1-dimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethylindan-4-yl]pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethylindan-4-yl]pyridine-3-carboxamide (This compound can be prepared 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 phosphate + TX, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide + TX, 2,4-dichlorophenylbenzenesulfonate + TX, 2,6-dimethyl-1H,5H-[1,4]di Thiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetron (this compound can be prepared from 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 from the method described in International Publication No. 2017 / 029179) (This compound can be prepared from the method described in International Publication No. 2017 / 029179) + TX, 2-chlorovinyl diethyl phosphate + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide + TX, 2-imidazolidone + TX, 2-isovalerylindan-1,3-dione + TX, 2-methyl(prop-2-inyl)aminophenylmethylcarbamate + TX, 2 -Oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide (This compound may be prepared from 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 from 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-hydroxypropyl]imidazole-4-carbonitrile (This compound is described in International Publication No. 2016 / 156290) (Can be prepared by the method described below) + TX, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitride (This compound can be prepared by the method described in International Publication No. 2016 / 156290) + TX, 3-bromo-1-chloroprop-1-ene + TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid + TX, 3-ethyl-1- Methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea + TX, 3-methyl-1-phenylpyrazole-5-yldimethylcarbamate + TX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine-3-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-chlorophenylphenyl sulfone + TX, 4-methyl(prop-2-inyl)amino-3,5-xylylmethylcarbamate + TX, 4-methylnonan-5-ol and 4-methylnonan-5-one + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-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-oxocyclohexy-1-enyldimethylcarbamate + TX, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid + TX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxami TX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methylpyridazine-4-carboxamide ((can 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-methyl-phenyl [(Nyl)-2,2-difluoro-ethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide (which can be prepared from the method described in International Publication No. 2020 / 109391) + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile + TX, 6-isopentenylaminopurine + TX, 8-fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethylbutyl]quinoline-3-carboxamide + TX,8-Fluoro-N-[(1S)-1-[(3-Fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, 8-Hydroxyquinoline sulfate + TX, Acethione + TX, Acetoprole + TX, Acibenzol + TX, Acibenzol-S-methyl + TX, Acrylonitrile + TX, Adoxophyes orana GV + TX, Agrobacterium radiobacter + TX, Aldoxycarb + TX, Aldrin + TX, Allosamidin + TX, Alixicarb + TX, α-Chlorohydrin + TX, α-Ecdysone + TX, α-Multistratotin + TX, Aluminum phosphide + TX, Amblyseius bacteria spp.)+TX, amectotrazine+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, antz+TX, Aphelinus abdominalis+TX, Aphidius colemani+TX, Aphidoletes aphidimiza aphidimyza)+TX, ahorate+TX, aramite+TX, arsenite+TX, athidathion+TX, Autographa californica NPV+TX, azaconazole+TX, azamethiphos+TX, azobenzene+TX, azothoate+TX, azoxystrobin+TX, Bacillus sphaericus Neide+TX, Bacillus thuringiensis delta-endotoxin+TX, barium carbonate+TX, barium 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, β-cyfluthrin + TX, β-cypermethrin + TX, Bethoxazine + TX, Bioetanomethrin + TX, Biopermethrin + TX, Bis(2-chloroethyl) ether + TX, Bis(tributyltin) oxide + TX, Bisagil + TX, Bisthiosemi + TX, Vitertanol + TX, Bixafen + TX, Blastocydin-S + TX, Borax + TX, Bordeaux mixture + TX, Boscalid + TX, Brevicomin + TX, Brosifacum + TX, Brofenvalerate + TX, Bromadiolon + TX, Bromethalin + TX, Bromfenbinphos + TX, Bromoacetamide + TX, Bromocyclene + TX, Bromo-DDT + TX, Bromophos + TX, Bromopropirate + TX, Bromuconazole + TX, Bronopol + TX, Bufencarb + TX, Viprimate + T X, Buprofezin + TX, Busulfan + TX, Buto-3-inyl N-[6-[[(Z)-[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxytyl]-2-pyridyl]carbamate + TX, Butacarb + TX, Butathiophos + TX, Butocarboxyme + TX, Butonate + TX, Butopyronoxyl + TX, Butoxy(polypropylene glycol) + TX, Butoxycarboxyme + TX, Butylpyridaben + TX, Calcium arsenate + TX, Calcium cyanide + TX, Calcium Polysulfide + TX, Camfechlor + TX, Captahol + TX, Captan + TX, Carbanolate + TX, Carbendazim + TX, Carbon disulfide + TX, Carbon tetrachloride + TX, Carbophenothion + TX, Carboxine + TX, Cartap hydrochloride + TX, CAS No. 2132414-04-9 + TX, CAS No. 2344721-61-3 + TX, Sebadin + TX, Quinomethionat + TX, Chloralose + TX, Chlorbenside + TX, Chlorbicyclene + TX, Chlordan + 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, Chlorfoxime + TX, Chlorprazofos + TX, Chlorthiofos + TX, Clozolinate + TX, Cholecalciferol + TX, Chrysoperla carnea carnea)+TX, Synerin I+TX, Synerin II+TX, Synerin+TX, Sysmethrin+TX, Cis-resmethrin+TX, Crocitrin+TX, Closantel+TX, Chodrelua+TX, Chodremon+TX, Copper acetarsenite+TX, Copper arsenate+TX, Copper dioctanoate+TX, Copper hydroxide+TX, Copper naphthenate+TX, Copper oleate+TX, Copper oxide+TX, Copper oxychloride+TX, Copper sulfate+TX, Coumocrol+TX, Coumafuryl+TX, Coumaphos+TX, Coumatetralyl+TX, Cryptomethocorbin+TX, Cumitoate+TX, Comoxystrobin+TX, Cresol+TX, Crimidine+TX, Crotamiton+TX, Clotoxyphos+TX, Cluthomate+TX, Cryolite+TX, Cryptolaemus montorgiensis Montrouzieri + TX, CS708 + TX, Kyurua + TX, Cufraneb + ​​TX, Cyanophenphos + TX, Cyanophos + TX, Cyanthoate + TX, Cyazofamide + TX, Sibutrin + TX, Cicletorin + TX, Cyclobtrifluram + TX, Cydia pomonella GV + TX, Cyflufenaamide + TX, Simiazole + TX, Cymoxanil + TX, Cyproconazole + TX, Cyprodinil + TX, Cithioate + TX, Cytokinin + 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, Dichlorobunthiazox+TX, Diclofenthion+TX, Diclofluanide+TX, Diclon+TX, Dichlorophene+TX, Dichlorvos+TX, Diclozoline+TX, Dicliphos +TX, Diclocimet +TX, Diclomezin +TX, Dichloran +TX, Dicresyl +TX, Dicyclanil +TX, Dicyclopentadiene +TX, Dierdrin +TX, Dienochlor +TX, Dietofencarb +TX, Diethyl 5-methylpyrazole 3-yl phosphate +TX, Diethyltoluamide +TX, Difenacum +TX, Difenoconazole +TX, Difethiaron +TX, Diflovidazine +TX, Diglyphus isaea isaea)+TX, Dirol+TX, Dimatif+TX, Dimefluthrin+TX, Dimefox+TX, Dimethane+TX, Dimethilimol+TX, Dimethomorph+TX, Dimetrin+TX, Dimethylcalvert+TX, Dimethylphthalate+TX, Dimethylvinphos+TX, Dimethilane+TX, Dimoxystrobin+TX, Dinex+TX, Dinex-Dikrexin+TX, Diniconasol+TX, Dinocap4+TX, Dinocap6+TX, Dinocton+TX, Dinopenton+TX, Dinoprop+TX, Dinosam+TX, Dinoseb+TX, Dinosulfone+TX, Dinoterbone+TX, Geophenolane+ TX, Dioxabenzophos+TX, Dioxathion+TX, Difacinone+TX, Diphenylsulfone+TX, Dipimethitron+TX, Dipirithione+TX, Disparure+TX, Disulfiram+TX, Dithianone+TX, Diticlophos+TX, DNOC+TX, Dodec-8-en-1-ylacetate+TX, Dodec-9-en-1-ylacetate+TX, Dodeca-8+TX, Dodemorph+TX, Dodicine+TX, Dodyne+TX, Dofenapine+TX, Dominicalu+TX, Doramectin+TX, DSP+TX, d-Tetramethrin+TX, Ecdysterone+TX, Edifenphos+TX, EI 1642+TX, EMPC+TX,Encarsia formosa + TX, Endotar + TX, Endothion + TX, Enestrobrin + TX, Enoxastrobin + TX, EPBP + TX, Epoxyconazole + TX, Eprinomectin + TX, Eretmocerus eremicus + TX, Ergocalciferol + TX, Etaphos + TX, E, Taboxam + TX, Ethiofencarb + TX, Ethyrimol + TX, Ethoatemethyl + TX, Ethyl 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoroprop-1-enoxy]phenyl]methyl]pyrazole-3-carboxylate (may be prepared from the method described in International Publication No. 2020 / 056090) + TX, Ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate (may be prepared from the method described in International Publication No. 2020 / 056090) (This compound can be prepared from the method described in International Publication No. 2018 / 158365) + TX, ethyl 1-[[4-[[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate + TX, ethyl 1-[[5-[[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate (This compound can be prepared from the method described in International Publication No. 2018 / 158365) + TX, ethyl 4-methyl octanoate + TX, ethyl formate + TX, ethyl hexanediol + TX, ethyl Ndibromide + TX, Ethylene dichloride + TX, Ethylene oxide + TX, Etridiazole + TX, Etrimophos + TX, Eugenol + TX, EXD + TX, Famoxadone + TX, Farnesol + TX, Farnesol and nerolidol + TX, Phenamidon + TX, Phenaminosulf + TX, Phenaminestrobin + TX, Phenarimol + TX, Phenazaflor + TX, Fenbuconazole + TX, Fenbutatin oxide + TX, Fenchlorphos + TX, Phenetacarb + TX, Fenflam + TX, Fenhexamide + TX, Fenitro Thione + TX, phenothiocarb + TX, phenoxacrim + TX, phenoxanil + TX, fenpiclonil + TX, fenpicoxamide + TX, fenpyritrin + TX, fenpropidine + TX, fenpropimorph + TX, fenpyrad + TX, fenpyrazamine + TX, fenpyroximate + TX, fenson + TX, phensulfothione + TX, fenthion + TX, fenthion-ethyl + TX, fentin + TX, fentriphanil + TX, ferrubam + TX, ferrimzon + TX, ferric phosphate + TX, furocumafen + TX,Floryl picoxamide + TX, fluazinam + TX, flubenteram + 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, fluoroimide + TX, fluoxapiproline + TX, fluoxastrobin + TX, fluoxythioconazole + TX, flupropazine + TX, flupropazine hydrochloride + TX, fluquinconazole + TX, flusilazole + TX, flusulfamide + TX, fluthianil + TX, flutolanil + TX, flutriafoll + TX, fluxapiroxad + TX, FM C1137+TX, Forpet+TX, Formaldehyde+TX, Formetanate+TX, Formetanate Hydrochloride+TX, Formparanate+TX, Fosetil-Aluminum+TX, Fosmethilan+TX, Fosspire+TX, Fosthietan+TX, Frontalin+TX, Fuberidazole+TX, Flalaxil+TX, Flamethopyr+TX, Flathiocarb+TX, Fretolin+TX, Furfural+TX, Gamma-HCH+TX, Gliodin+TX, Grandlua+TX, Grandlua I+TX, Grandlua II+TX, Grandlua III+TX, Grandlua IV+TX, Guazatine+TX, Guazatine Acetate+TX, Halfenprox+TX, HCH+TX, Hemel+TX, Hempa+TX, HEOD+TX, Heptachlor+TX, Heterophos+TX, Heterorhabditis bacteriophora bacteriophora) and H. megidis + TX, hexaconazole + TX, hexadecylcyclopropane carboxylate + TX, hexalua + TX, hexamide + TX, HHDN + TX, Hippodamia convergens + TX, hydralgafen + TX, slaked lime + TX, hydrogen cyanide + TX, himexazole + TX, hikincarb + TX, imanin + TX, imazalil + TX, imibenconazole + TX, iminoctadine + TX,Impilfluxam + TX, Ipconazole + TX, Ipfentrifluconazole + TX, Ipflufenoquin + TX, Iprobenphos + TX, Iprodione + TX, Iprovalicarb + TX, Ipsdienol + TX, Ipsenol + TX, IPSP + TX, Isamidophos + TX, Isazofos + TX, Isobenzane + TX, Isocarbophos + TX, Isodrine + TX, Isofenphos + TX, Isofetamide + TX, Isoflucipram + TX, Isolan + TX, Isoprothiolan + TX, Isopyrazam + TX, Isothianil + TX, Isoxathion + TX, Japonila + TX, Jasmolin I + TX, Jasmolin II + TX, Iodophenphos + TX, Juvenile Hormone I + TX, Juvenile Hormone II + TX, Juvenile Hormone III + TX, Cadetrin + TX, Kasugamycin + TX, Kasugamycin Hydrochloride Hydrate + TX, Kereban + TX, Kinetin + TX, Quinoprene + TX, Kresoxim-Methyl + TX, Lead Arsenate + TX, Leptomastix Dactylopii dactylopii)+TX, leptophos+TX, lindan+TX, lineatin+TX, lilimphos+TX, litorua+TX, lupulua+TX, rubenmixianan+TX, lithidathione+TX, Macrolophus caliginosus+TX, magnesium phosphide+TX, maronoben+TX, Mamestra brassicae brassicae) NPV+TX, mancapper+TX, mancozeb+TX, mandestrobin+TX, mandipropamide+TX, maneb+TX, mazidox+TX, m-cumenylmethylcarbamate+TX, mecarbam+TX, mecarfon+TX, medolua+TX, mefentrifluconazole+TX, megatomoic acid+TX, menazone+TX, mepanipyrim+TX, meperfluthrin+TX, mephosphorane+TX, mepronil+TX, mercury oxide+TX, mercury 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, Metaril picoxamide + TX, Metconazole + TX, Metepa + TX, Methacryphos + TX, Methanesulfonyl fluoride + TX, Metasulfocarb + TX, Methiotepa + TX, Metoclotophos + TX, Methoprene + TX, Methquin-butyl + TX, Methotrin + TX, Methoxychlor + TX, Methyl(Z)2(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate + TX, Methyl(Z)2-(5-cyclopentyl-2-methylphenoxy)- 3-Methoxy-prop-2-enoate (These compounds can be prepared from the method described in International Publication No. 2020 / 193387) + TX, Methyl(Z)-2-[5-(3-isopropylpyrazole-1-yl)-2-methylphenoxy]-3-Methoxy-prop-2-enoate + TX, Methyl(Z)3-Methoxy-2-[2-methyl-5-(3-propylpyrazole-1-yl)phenoxy]prop-2-enoate + TX, Methyl(Z)-3-Methoxy-2-[2-methyl-5-(4-propyltriazole-2- [(Iyl)phenoxy]prop-2-enoate + TX, methyl(Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazole-1-yl]phenoxy]prop-2-enoate (these compounds can be prepared from the method described in International Publication No. 2020 / 079111) + TX, methyl(Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazole-2-yl]phenoxy]prop-2-enoate + TX, methyl ahorate + TX, methyl bromide + TX, methyl eugeno 6-L + TX, methyl isothiocyanate + TX, methyl N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazole-4-yl]-2-methyl-phenyl]methyl]carbamate (may be prepared from the method described in International Publication No. 2020 / 097012) + TX, methyl N-[[4-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazole-4-yl]-2-methyl-phenyl]methyl]carbamate (may be prepared from the method described in International Publication No. 2020 / 097012) + TX,Methyl N-[[5-[4-(2,4-dimethylphenyl)triazole-2-yl]-2-methylphenyl]methyl]carbamate + TX, methylchloroform + TX, methylene chloride + TX, methylneodecanamide + TX, methylram + TX, methylcarb + TX, metminostrobin + TX, methoxadiazone + TX, metraphenone + TX, methyltetraprole + TX, MGK264 + TX, milbemycin oxime + TX, mipafox + TX, mirex + TX, monoclotophos + TX, morphothion + TX, molzide + TX, moxidectin + TX, muscarua + TX, mycrobutanil + TX, microzoline + TX, Myrothecium bergaria verrucaria) composition + TX, N-((1R)-1-benzyl-3-chloro-1-methyl-buto-3-enyl)-8-fluoroquinoline-3-carboxamide (These compounds may be prepared from the method described in International Publication No. 2017 / 153380) + TX, N-((1S)-1-benzyl-3-chloro-1-methyl-buto-3-enyl)-8-fluoroquinoline-3-carboxamide (These compounds may 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-phenoxyphenyl)-N-ethyl-N-methyl-formamidine + TX, N,2-dimethoxy-N -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide + TX, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]1,2,4-triazole-3-amine (These compounds are described in International Publication No. 2017 / 055473, and No. 20 (Can be prepared by the methods described in Nos. 17 / 055469, Nos. 2017 / 093348 and Nos. 2017 / 118689) + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoroquinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoroquinoline-3-carboxamide + TX,N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoroquinoline-3-carboxamide+TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoroquinoline-3-, Carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoroquinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoroquinoline-3-carboxamide + TX, N-[(E)-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-methyl-phenyl [Nyl]-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'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (these compounds may be prepared from the method described in International Publication No. 2015 / 155075) + TX, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX,N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine+TX, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine+TX, N-[N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide (These compounds are internationally disclosed.) (These compounds may be prepared from the method described in International Publication No. 2018 / 202428) + TX, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine (These compounds may be prepared from the method described in International Publication No. 2018 / 228896) + TX, Nabam + TX, Naphthalophos + TX, Nared + TX, Naphthalene + TX, NC170 + TX, Neodiprion Celltifer N. sertifer) NPV and N. lecontei NPV + TX, nerolidol + TX, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide + TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetane-2-yl]phenyl]-N-methyl-formamidine + TX, nickel bis(dimethyldithiocarbamate) + TX, niclosamide-olamine + TX, nicotine + TX, nicotine sulfate +TX, Niflulidide +TX, Nikcomycin +TX, N-Isopropyl-N'-[5-Methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine +TX, Nichiazine +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 acetate+TX, octylinone+TX, oflas+TX, oleic acid+TX, omethoate+TX, orflurua+TX, Orius bacteria spp.)+TX, Orictalua+TX, Orysastrobin+TX, Ostramon+TX, Oxadixyl+TX, Oxamate+TX, Oxathiapiproline+TX, Oxine-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, phenakapton+TX, fosacetim+TX, phosalon+TX, phosdiphen+TX, phosphorane+TX, phosglycine+TX, fosniclor+TX, phosphamidone+TX, phosphine+TX, phosphorus+TX, phoxim-methyl+TX, phthalide+TX, Phytoseiulus persimilis+TX, picarbutrazox+TX, picaridin+TX, picoxystrobin+TX, pindone+TX, piperazine+TX, piperonyl butoxide+TX, piprotal+TX, pyrimetaphos+TX, polychlorodicyclopentadiene isomer+TX, polychloroterpene+TX, polynactin+TX, polyoxin+TX, potassium arsenate+TX, potassium 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, Prothiophos + TX, Protoate + TX, Pidiflumetofen + TX, Pyrachilostrobin + TX, Pyramethostrobin + TX, Pyraoxystrobin + TX, Pyrapropoin + TX, Pyraziflumid + TX, Pyrazophos + TX, Pyrethmetrin+TX, Pyrethrin I+TX, Pyrethrin II+TX, Pyrethrin+TX, Pyribencarb+TX, Pyridaclomethyl+TX, Pyridafenthion+TX, Pyridine-4amine+TX, Pyriphenox+TX, Pyrimethanil+TX, Pyrimite+TX, Pyrimorph+TX, Pyrinulone+TX, Pyriophenone+TX, Pyrisoxazole+TX, Pyrroquilon+TX, Quassia+TX, Quinalphos+TX, Quinalphos-methyl+TX, Quinoclamine+TX, Quinofumelin+TX, Quinonamide+TX, Quinothione+TX, Quinoxyfen+TX, Quinthiophos+TX, Quintozen+TX, R-1492+TX, Lafoxanide+TX, Resmethrin+TX, Reynoutria saccharinensis Sachalinensis extract + TX, Ribavirin + TX, 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, SI0009 + TX, Siguru + TX, Simazine + TX, Simeconazole + TX, Sodium arsenite + 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,Solzidine + TX, Spiroxamine + TX, SSI-121 + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema feltiae + TX, Steinernema glaseri + TX, Steinernema riobrave + TX, Steinernema riobravis + TX, Steinernema scapterisci + TX, Steinernema species (Steinernema) 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, Tebufloquine+TX, Tebupyrimphos+TX, Tecrophthalam+TX, Temephos+TX, Tepa+TX, TEPP+TX, Terarethrin+TX, Terbam+TX, tert-butyl N-[6-[[[(1-methyltetrazole-5yl)-phenyl-methylene]amino]oxyme [Tyl]-2-pyridyl]carbamate + TX, tetrachloroethane + TX, tetrachlorothiophene + TX, tetraconazole + TX, tetradec-11-en-1-yl acetate + TX, tetradiphon + TX, tetramethylfluthrin + TX, tetrasul + TX, thallium sulfate + TX, thiabendazole + TX, thiaphenox + TX, thiapronil + TX, ticlophos + TX, tifluzamide + TX, thiocarboxyme + TX, thiocyclam + TX, thiocyclam hydrogen oxalate + TX, thiodiazole copper + TX, thiophanox + TX, thiohempa + TX, thiomelsal + TX, thiometon + TX, thionazine + TX, thiophanate + TX, thiophanate-methyl + TX, thioquinox + TX, thiosultap + TX,Thiosultap-sodium + TX, Thiotepa + TX, Thyramine + TX, Thuringensine + TX, Thiazinyl + TX, Tolcrophos-methyl + TX, Tolprocarb + TX, Trilfluanide + TX, Tralomethrin + TX, Transpermethrin + TX, Tretamine + TX, Triadimephone + TX, Triadimenol + TX, Triamiphos + TX, Triatene + TX, Triazamate + TX, Triazophos + TX, Triazooxide + TX, Triazlon + TX, Tributyltin oxide + TX, Trichlormetaphos 3 + TX, Trichloronat + TX, Trichogramma spp. + TX, Triclopyricarb + TX, Tricyclazole + TX, Tridemorph + TX, Triphenmorph + TX, Triphenophos + TX, Trifloxystrobin + TX, Triflumizole + TX, Triforin + TX, Trimedrua + TX, Trimedrua A + TX, Trimedrua B1 + TX, Trimedrua B2 + TX, Trimedrua C + TX, Trimetacarb + TX, Trinactin + TX, Trinexapac + TX, Triphenyltin acetate + TX, Triphenyltin hydroxide + TX, Triplen + TX, Triticonazole + TX, Trunkcol + TX, Typhlodromus occidentalis Occidentalis) + TX, Uredepa + TX, Validamycin + TX, Valifenarate + TX, Bamidthion + TX, Vaniliprole + TX, Veratridine + TX, Veratrin + TX, Berbutin + TX, Verticillium lecanii + TX, Vinclozoline + TX, Warfarin + TX, XMC + TX, Xylenol + TX, Zeatin + TX, Zetamethrine + TX, Zonchenmycin + TX, Zinc naphthenate + TX, Zinc phosphide + TX, Thiazole zinc + TX, Zineb + ​​TX, Ziram + TX, Zolaprofos + TX, Acinetobacter lwoffii + TX, Acremonium alternatum + TX, Acremonium cephalosporium + TX, Acremonium diospyri + TX, Acremonium obclavatum + TX, Adoxophyes orana granulovirus (AdoxGV) (Capex®) + TX, Agrobacterium radiobacter strain K84 (Galltrol-A®) + TX, Alternaria alternate + TX, Alternaria cassia (Alternaria Cassia) + TX, Alternaria destruens (Smolder®) + TX, Ampelomyces quisqualis (AQ10®), Aspergillus flavus F36 (AF36®) + TX, Aspergillus flavus NRRL 21882 (Aflaguard®) + TX, Aspergillus spp. + TX, Aureobasidium pullulans + TX, Azospirillum (MicroAZ®, TAZO B®) + TX, Azotobacter + TX, Azotobacter croocuccum Bacillus chroocuccum (Azotomeal®) + TX, Azotobacter cysts (Bionatural Blooming Blossoms®) + TX, Bacillus amyloliquefaciens + TX, Bacillus cereus (Bacilluscereus)+TX, Bacillus chitinosporus strain AQ746+TX, Bacillus chitinosporus strain CM-1+TX, Bacillus circulans+TX, Bacillus firmus (BioSafe®, BioNem-WP®)+TX in specific strains CNMC 1-1582 (e.g., VOTIVO from BASF SE), Bacillus licheniformis strain 3086 (EcoGuard®, Green Releaf®)+TX, Bacillus licheniformis (Bacillus Bacillus licheniformis) strain HB-2 (Biostart (trademark), formerly Rhizoboost (registered trademark)) + TX, Bacillus macerans + TX, Bacillus marismortui + TX, Bacillus megaterium + TX, Bacillus mycoides strain AQ726 + TX, Bacillus papillae (Milky Spore Powder (registered trademark)) + 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, Bacillusspp.) strain AQ178+TX, Bacillus subtilis strain AQ153+TX, Bacillus subtilis strain AQ743+TX, Bacillus subtilis strain QST713 (CEASE®, Serenade®, Rhapsody®)+TX, Bacillus subtilis strain QST714 (JAZZ®)+TX, Bacillus subtilis strain QST3002+TX, Bacillus subtilis strain QST3004+TX, Bacillus subtilis var amyloricephasiens Bacillus amyloliquefaciens) strain FZB24 (Taegro®, Rhizopro®) + TX, Bacillus thuringiensis aizawai GC91 (Agree®), Bacillus thuringiensis Cry 2Ae + TX, Bacillus thuringiensis Cry1Ab + TX, Bacillus thuringiensis israelensis (BMP123®, Aquabac®, VectoBac®) + TX, Bacillus thuringiensis kurstaki (Javelin®, Deliver®, CryMax®, Bondide®, Scutella) WP (registered trademark), Turilav WP (registered trademark), Astuto (registered trademark), Dipel WP (registered trademark), Biobit (registered trademark), Foray (registered trademark)) + TX, Bacillus thuringiensis kurstaki (BMP)123 (Baritone®) + TX, Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF / 3P®) + TX, Bacillus thuringiensis strain AQ52 + TX, 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 species (Beauveria spp.)+TX, Botrytis cineria+TX, Bradyrhizobium japonicum (TerraMax®)+TX, Brevibacillus brevis+TX, Burkholderia cepaciaCandida 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 meribiosica (Candida Candida melibiosica)+TX, Candida oleophila strain O+TX, Candida parapsilosis+TX, Candida pelliculosa+TX, 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 flavigena)+TX, Chaetomium cochliodes (Nova-Cide®)+TX, Chaetomium globosum (Nova-Cide®)+TX, Chromobacterium subtsugaesubtsugae) strain PRAA4-1T (Grandevo(registered trademark)) + TX, Cladosporium chlorocephalum + TX, Cladosporium cladosporioides + TX, Cladosporium oxysporum + TX, Cladosporium spp. + TX, Cladosporium tenuissimum (Clados Porium 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, Dreshlera hawaiinensis + TX, Enterobacter cloacae + TX, Enterobacteriaceae + TX, Entomophtora virulenta (Vektor®) + TX, Epicoccum nigrum + TX, Epicoccum purpurascens + TX, Epicoccum spp.)+TX, Filobasidium floriforme+TX, Fusarium acuminatum+TX, Fusarium chlamydosporum+TX, Fusarium oxysporum (Fusaclean®, Biofox C®)+TX, Fusarium proliferatum+TX, Fusarium spp.+TX, Galactomyces geotrichum+TX, Gliocladium catenulatum (Primastop®, Prestop®)+TX, Gliocladium roseum roseum)+TX, Gliocladium spp. (SoilGard®)+TX, Gliocladium virens (Soilgard®)+TX, Granulovirus (Granupom®)+TX, Halobacillus halophilus+TX, Halobacillus litoralis+TX, Halobacillus trueperi+TX, Halomonas spp.)+TX, Halomonas subglaciescola+TX, Halovibrio variabilis+TX, Hanseniaspora uvarum+TX, Helicoverpa armigera nuclear polyhedron virus (Helicovex®)+TX, Helicoverpa zea nuclear polyhedron virus (Gemstar®)+TX, Isaria fumosorosea (Paecilomyces fumosoroseus strain, PFR-97®, formerly known as PreFeRal®)+TX, Isoflavone formononetin (Isoflavone 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® by Koppert / Arysta)+TX, Lecanicillium longisporum (Vertiblast®)+TX, Lecanicillium muscariuporus (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 ochracea ochracea)+TX, Muscodor albus 620 (Muscudor(registered trademark))+TX, Muscodor roseus, especially strain A3-5 (accession number NRRL30548)+TX, Mycorrhizae spp.)(AMykor(registered trademark), Root Maximizer(registered trademark))+TX, Myrothecium verrucaria strain AARC-0255(DiTera(registered trademark), BROS PLUS(registered trademark))+TX, Ophiostoma piliferum strain D97(Sylvanex(registered trademark))+TX, Paecilomyces farinosus+TX, Paecilomyces lilacinus strain 251(MeloCon WG(registered trademark))+TX, Paecilomyces linacinus(Biostat WP(registered trademark))+TX, Paenibacillus polymyxa polymyxa)+TX, Pantoea agglomerans (BlightBan C9-1(registered trademark))+TX, Pantoea species (Pantoea spp.)+TX, Pasteuria nishizawae, especially strain Pn1 (CLARIVA from Syngenta / ChemChina);+TX, Pasteuria spp. (Econem(registered trademark))+TX, Penicillium aurantiogriseum+TX, Penicillium billai (Jumpstart(registered trademark), TagTeam(registered trademark))+TX, Penicillium brevicompactum+TX, Penicillium phlequentans (Penicillium Penicillium frequentans) + TX, Penicillium griseofulvum + TX, Penicillium purpurogenum + TX, Penicillium spp.)+TX, Penicillium viridicatum+TX, Phlebiopsis gigantean (Rotstop®)+TX, Phosphate-soluble bacteria (Phosphomeal®)+TX, Phytophthora cryptogea+TX, Phytophthora palmivora (Devine®)+TX, Pichia anomala+TX, Pichia guilliermondii+TX, Pichia membranaefaciens+TX, Pichia onychis+TX, Pichia stipites (Pichia Pseudomonas stipites)+TX, Pseudomonas aeruginosa+TX, Pseudomonas aureofasciens (Spot-Less Biofungicide®)+TX, Pseudomonas cepacia+TX, Pseudomonas chlororaphis (AtEze®)+TX, Pseudomonas corrugate+TX, Pseudomonas fluorescens (Zequanox®)+TX, Pseudomonas fluorescens strain A506 (BlightBan A506®)+TX, Pseudomonas ptida (Pseudomonas Pseudomonas putida)+TX, Pseudomonas reactans+TX, Pseudomonas spp.+TX, Pseudomonas syringae (Bio-Save®)+TX, Pseudomonas viridiflava+TX, Pseudozai.Pseudozyma flocculosa strain PF-A22UL (Sporodex L®) + TX, Puccinia canaliculata + TX, Puccinia thlaspeos (Wood Warrior®) + TX, Pythium paroecandrum + TX, Pythium oligandrum (Polygandron®, Polyversum®) + TX, Pythium periplocum + TX, Rhanella aquatilis + TX, Ranella species (Rhanella spp.)+TX, Rhizobia (Dormal®, Vault®)+TX, Rhizoctonia+TX, Rhodococcus globerulus strain AQ719+TX, Rhodosporidium diobovatum+TX, Rhodosporidium toruloides, Rhodotorula glutinis+TX, Rhodotorula graminis+TX, Rhodotorula mucilagnosa+TX, Rhodotorula rubra+TX, Rhodotorula species (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 polyhedrosis virus (Spod-X®, Spexit®) + TX, Spodoptera littoralis nuclear polyhedrosis virus (Littovir®) + TX, Sporobolomyces roseus + TX, Stenotrophomonas maltophilia Streptomyces maltophilia) + TX, Streptomyces albaduncus + TX, Streptomyces exfoliates + TX, Streptomyces galbus + TX, 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 gammushi (Tenet®)+TX, Trichoderma hamatum TH 382+TX, Trichoderma harzianum rifai (Mycostar®)+TX, Trichoderma harzianum T-22 (Trianum-P®, PlantShield HC®, RootShield®, Trianum-G®)+TX, Trichoderma harzianum (Trichoderma harzianum)T-39(Trichodex(registered trademark))+TX, Trichoderma inhamatum+TX, Trichoderma koningii+TX, Trichoderma lignorum+TX, Trichoderma longibrachiatum+TX, Trichoderma polysporum(Binab T(registered trademark))+TX, Trichoderma spp.)LC52 (Sentinel (registered trademark)) + TX, Trichoderma taxi + TX, Trichoderma virens (formerly Gliocladium virens GL-21) (SoilGuard (registered trademark)) + TX, Trichoderma virens + TX, Trichoderma viride + TX, Trichoderma viride strain ICC080 (Remedier (registered trademark)) + TX, Trichosporon pullulans + TX, Trichosporon spp. + TX, Trichothecium roseum + TX, Trichothecium spp.)+TX, Typhula phacorrhiza strain 94670+TX, Typhula phacorrhiza strain 94671+TX, Ulocladium atrum+TX, Ulocladium oudemansii (Botry-Zen®)+TX, Ustilago maydis+TX), various bacteria and auxiliary micronutrients (Natural II®)+TX, various fungi (Millennium Microbes®)+TX, Verticillium chlamydosporium+TX, Vip3Aa20 (VIPtera®)+TX, Virgibaclillus marismortzii marismortui)+TX, Xanthomonas campestris pv. Poae (Camperico®)+TX, Xenorhabdus bovienii+TX, Xenorhabdus nematophilus+TX, . AGNIQUE® MMF + TX, Azadirachtin (Plasma Neem Oil®, AzaGuard®, MeemAzal®, Molt-X®, e.g., Certis, US-made AZATIN XL) + TX, Plant 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, Glycinebetaine (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 (EF400®) + TX, Rosemary Sesame Peppermint Thyme and Cinnamon Extract Mixture (EF300®) + TX, Neem Oil + TX, Nepeta cataria (Catnip Oil) + TX, Nepeta catalina (Nepeta catarina) + TX, nicotine + TX, oregano oil (MossBuster®) + TX, Pedaliaceae oil (Nematon®) + TX, pine oil (Retenol®) + TX, pyretorum + TX, Quillaja saponaria (QuillajaSaponaria) (NemaQ®) + TX, Reynoutria sachalinensis (Regalia®, Sakalia®) + TX, Rotenone (Eco Roten®) + TX, Rutaceae plant extract (Soleo®) + TX, Soybean oil (Ortho ecosense®) + TX, Brown algae storage glucum (Laminarin®) + TX, Thyme oil + TX, (E,Z)-7,9-Dodecadiene-1-yl acetate + TX, (E,Z,Z)-3,8,11-Tetradecatrienylate + TX, (Z,Z,E)-7,11,13-Hexadecatrienal + TX, 2-Methyl-1-butanol + TX, Biolure® + TX, Blackheaded Fireworm Pheromone (3M Sprayable Blackheaded Fireworm Pheromone®) + TX, Calcium Acetate + TX, Check-Mate® + TX, Codling Moth Pheromone (Paramount dispenser-(CM) / Isomate C-Plus®) + TX, Entostat Powder (Exosex CM®) (Exosex extract from palm trees) + TX, Grape Berry Moth Pheromone (3M MEC-GBM Sprayable Pheromone(registered trademark))+TX, Lavanzuryl senecioate+TX, Leafroller pheromone (3M MEC-LR Sprayable Pheromone(registered trademark))+TX, Muscamone (Snip7 Fly Bait(registered trademark))+TX, Oriental Fruit Moth pheromone (3M oriental fruit moth sprayable pheromone(registered trademark))+TX, Peachtree Borer pheromone (Isomate-P(registered trademark))+TX, Scenturion(registered trademark)+TX, Starbar Premium Fly Bait(registered trademark))+TX, Tomato pinworm pheromone (3M Sprayable pheromone(registered trademark))+TX, Acerophagus papaya + TX, Adalia bipunctata (Adalia-System®) + TX, Adalia bipunctata (Adaline®) + TX, Adalia bipunctata (Aphidalia®) + TX, Ageniaspis citricola + TX, Ageniaspis fuscicollis + TX, Amblyseius andersoni (Anderline®, Andersoni-System®) + TX), Amblyseius californicus californicus) (Amblyline(registered trademark), Spical(registered trademark)) + TX, Amblyseius cucumeris (Thripex(registered trademark), Bugline cucumeris(registered trademark)) + TX, Amblyseius fallacis (Fallacis(registered trademark)) + TX, Amblyseius swirskii (Bugline swirskii(registered trademark), Swirskii-Mite(registered trademark)) + TX, Amblyseius womersleyi (WomerMite(registered trademark)) + TX, Amitus hesperidum + TX, Anagrus atomus + TX, Anagyrus fussiventris fusciventris)+TX, Anagyrus kamali+TX, Anagyrus loecki+TX, Anagyrus pseudococci (Citripar(registered trademark))+TX, Anicetus benefices+TX, Anisopteromalus karanduraecalandrae)+TX, Anthocoris nemoralis (Anthocoris-System(registered trademark))+TX, Aphelinus abdominalis (Apheline(registered trademark), Aphiline(registered trademark)),+TX, Aphidius asychis+TX, Aphidius colemani (Aphipar(registered trademark))+TX, Aphidius ervi (Aphelinus-System(registered trademark))+TX, Aphidius ervi (Ervipar(registered trademark))+TX, Aphidius gifuensis+TX, Aphidius matricariae (Aphidius Matricariae) (Aphipar-M(registered trademark)) + TX, Aphidoletes aphidimyza (Aphidend(registered trademark), Aphidoline(registered trademark)) + TX, Aphytis lingnanensis + TX, Aphytis melinus + TX, Aprostocetus hagenowii + TX, Atheta coriaria (Staphyline(registered trademark)) + TX, Bombus spp. + TX, Bombus terrestris (Beeline(registered trademark), Tripol(registered trademark)) + TX, Bombus terrestris (Natupol Beehive (registered trademark) + TX, Cephalonomia stephanoderis + TX, Chilocorus nigritus + TX, Chrysoperla carnea (Chrysoline (registered trademark), Chrysopa (registered trademark)) + TX, Chrysoperla rufirabris (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 longicauda longicaudata)+TX, Diaparsis jucunda+TX, Diaphorencyrtus aligarhensis+TX, Diglyphus isaeaeisaea) (Diminex®, Miglyphus®, Digline®) + TX, Diversinervus spp. + TX, Encarsia citrina + TX, Encarsia formosa (Encarsia max®, Encarline®, En-Strip®) + TX, Encarsia guadeloupae + TX, Encarsia haitiensis + TX, Episyrphus balteatus (Syrphidend®) + 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 (Fopius arisanus)+TX, Fopius ceratitivorus+TX, formononetin (Wirless Beehome®)+TX, Franklinothrips bespiformisvespiformis)(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, Lbalia leucospoides + TX, Lecanoideus floccissimus + TX, Lemophagus elabunnus Leptomastix errabundus) + TX, Leptomastidea abnormis + TX, Leptomastix dactylopii (Leptopar®) + TX, Leptomastix epona (Leptomastixepona)+TX, Lindorus lophanthae+TX, Lipolexis oregmae+TX, Lucilia caesar (Natufly(registered trademark))+TX, Lysiphlebus testaceipes+TX, Microlophus caliginosus (Mirical-N(registered trademark), Macroline c(registered trademark) (Trademark), Mirical (Registered Trademark)) + TX, Mesoseiulus longipes + TX, Metaphycus flavus + TX, Metaphycus lounsburyi + TX, Micromus angulatus (Milacewing (Registered Trademark)) + TX, Microterys flavus + TX, Muscidifurax raptorellus and Spalangia cameroni (Biopar (Registered Trademark)) + TX, Neodryinus typhlocybae + TX, Neoseiulus californicus + TX, Neoseiulus cucumeris (Neoseiulus cucumeris)(THRYPEX(registered trademark)), Neoseiulus fallacis+TX, Nesideocoris tenuis(NesidioBug(registered trademark), Nesibug(registered trademark))+TX, Ophyra aenescens(Biofly(registered trademark))+TX, Orius insidiosus(Thripor-I(registered trademark), Oriline I(registered trademark))+TX, Orius laevigatus(Thripor-L(registered trademark), Oriline I(registered trademark))+TX, Orius majusculus(Oriline m(registered trademark))+TX, Orius strigikolis(Orius *Strigicollis* (Thripor-S®) + TX, *Pauesia juniperorum* + TX, *Pediobius foveolatus* + TX, *Phasmarhabditis*hermaphrodita) (Nemaslug®) + TX, Phymastichus coffea + TX, Phytoseiulus macropilus + TX, Phytoseiulus persimilis (Spidex®, Phytoline p®) + TX, Podisus maculiventris (Podisus®) + TX, Pseudacteon curvatus + TX, Pseudacteon obtusus + TX, Pseudacteon tricuspis + TX, Pseudaphycus maculipennis + TX, Pseudleptomastix mexicana mexicana)+TX, Psyllaephagus pilosus+TX, Psyttalia concolor (complex)+TX, Quadrastichus spp.+TX, Rhyzobius lophanthae+TX, Rodolia cardinalis+TX, Rumina decollate+TX, Semielacher petiolatus+TX, Sitobion avenae (Ervibank®)+TX, Steinernema carpocapsae (Nematac C®, Millennium®, BioNem C (Registered Trademark), NemAttack (Registered Trademark), Nemastar (Registered Trademark), Capsanem (Registered Trademark)) + TX, Steinernema feltiae (NemaShield (Registered Trademark), Nemasys F (Registered Trademark), BioNemF (registered trademark), Steinernema-System (registered trademark), NemAttack (registered trademark), Nemaplus (registered trademark), Exhibitline sf (registered trademark), Scia-rid (registered trademark), Entonem (registered trademark)) + TX, Steinernema kraussei (Nemasys L (registered trademark), BioNem L (registered trademark), Exhibitline srb (registered trademark)) + TX, Steinernema riobrave (BioVector (registered trademark), BioVektor (registered trademark)) + TX, Steinernema scapterisci (Nematac S (registered trademark)) + TX, Steinernema spp. (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 + TX, Trichogramma brassicae (Tricholine b (registered trademark)) + TX, Trichogramma brassicae (Tricho-Strip (registered trademark)) + TX, Trichogramma evanescens + TX, Trichogramma minutum + TX, Trichogramma ostriniae (Trichogramma ostriniae)+TX, Trichogramma platneri+TX, Trichogramma plethiosumpretiosum) + TX, Xanthopimpla Stemmator + TX, Abscisic acid + TX, Aminomite® + TX, BioGain® + TX, bioSea® + TX, CAS No. 2643947-26-4 + TX, Chondrostereum purpureum (Chontrol Paste®) + TX, Colletotrichum gloeosporioides (Collego®) + TX, Copper octanoate (Cueva®) + TX, Delta Trap (Trapline d®) + TX, Erwinia amylovora (Harpin) (ProAct®), Ni-HIBIT Gold CST(registered trademark))+TX, fatty acids derived from natural by-products of extra virgin olive oil (FLIPPER(registered trademark))+TX, ferric phosphate (Ferramol(registered trademark))+TX, funnel trap (Trapline y(registered trademark))+TX, Gallex(registered trademark)+TX, Grower's Secret(registered trademark)+TX, 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), RebellAmarillo(registered trademark))+TX, SuffOil-X(registered trademark)+TX, Trap (Takitrapline y+b(registered trademark))+TX, Bacillus mojavensis strain R3B (accession number NCAIM(P)B001389) (International Publication No. 2013 / 034938) +TX from Certis USA LLC+TX, Bacillus pumilus strain BU F-33 (CARTISSA® from BASF, EPA Reg 71840-19) +TX with NRRL accession number 50185, Bacillus subtilis CX-9060 from Certis USA LLC, Bacillus sp. strain D747 (DOUBLE from Kumiai Chemical Industry Co.,Ltd.) with accession number FERM BP-8234 (Available as NICKEL®), U.S. Patent No. 7094592 + TX, Bacillus subtilis strain BU1814 (VELONDIS® PLUS, VELONDIS® FLEX and VELONDIS® EXTRA from BASF SE) + TX, Bacillus subtilis var. Amyloliquefaciens strain FZB24 (Available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5) with accession number DSM 10271) + TX, Bacillus subtilis, in particular strain QST713 / AQ713 (NRRL accession number B-21661, described in U.S. Patent No. 6060051, Bayer CropScience Available from LP, US as SERENADE® OPTI or SERENADE® ASO + TX, Paenibacillus polymyxa, especially strain AC-1 (e.g., Green Biotech Company Ltd.)Paenibacillus sp. strains with accession numbers NRRL B-50972 or NRRL B-67129, International Publication No. 2016 / 154297, Pantoea agglomerans, particularly strain E325 (accession number NRRL21856) (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 a mixture 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, in particular Lesaffre et Strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938 or CNCM No. 1-3939 (International Publication No. 2010 / 086790) + TX from Compagnie, FR. Agrobacterium radiobacter strain K84 (e.g., GALLTROL-A® from AgBioChem, CA) + TX, Bacillus amyloliquefaciens isolate B246 (e.g., AVOGREEN® from University of Pretoria) + TX, Bacillus amyloliquefaciens strain F727 (also known as MBI110) (NRRL accession number B-50768, International Publication No. 2014 028521) (STARGUS® from Marrone Bio Innovations) + TX, Bacillus amyloliquefaciens strain FZB42, accession number DSM 23117 (ABiTEP, available from DE as RHIZOVITAL®) + TX, Bacillus amyloliquefaciens, in particular strain D747 (accession number FERM BP-8234, available from Kumiai Chemical Industry Co., Ltd. as Double Nickel®, with U.S. Patent No. 7094592) + TX, Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (QUARTZO® (WG) and PRESENCE® (WP) from FMC Corporation) + TX, Bacillus licheniformis, in particular accession number ATCC 55406, strain SB3086 (available from Novozymes as ECOGUARD® Biofungicide and GREEN RELEAF®, with international publication no. 2003 / 000051) + TX, Bacillus methylotrophicus strain BAC-9912 (Chinese Academy of Sciences' Institute of Applied(From Ecology) +TX, Bacillus mycoides, isolated strain with accession number B-30890 (available from Certis USA LLC as BMJ TGAI® or WG and LifeGard®) +TX, Bacillus pumilus, in particular strain GB34 (available from Bayer AG, DE as Yield Shield®) +TX, Bacillus pumilus, in particular strain QST2808 (with accession number NRRL B-30087, described in U.S. Patent No. 6,245551, available from Bayer CropScience LP, US as SONATA®) +TX, Bacillus subtilis CX-9060 +TX from Certis USA LLC, Bacillus subtilis (Bacillus Bacillus subtilis) IAB / BS03 (AVIV (trademark) from STK Bio-Ag Technologies, PORTENTO (registered trademark) from Idai Nature) + TX, Bacillus subtilis strain KTSB (FOLIACTIVE (registered trademark) from Donaghys) + TX, Bacillus subtilis strain BU1814 (available as VELONDIS (registered trademark) PLUS, VELONDIS (registered trademark) FLEX and VELONDIS (registered trademark) EXTRA from BASF SE) + TX, Bacillus subtilis strain GB03 (available as Kodiak (registered trademark) from Bayer AG, DE) + TX, Bacillus subtilis strain MBI 600 (BASF SE), accession number NRRL B-50595, U.S. Patent No. 5,061,495 (Available as SE SUBTILEX) + TX, Bacillus subtilisBacillus subtilis) strain Y1336 (registered as a biological fungicide in Taiwan under registration numbers 4764, 5454, 5096 and 5277, available as BIOBAC® WP from Bion-Tech, Taiwan) + TX, Bacillus subtilis var. amyloliquefaciens strain FZB24 (available as TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5) from Novozymes) + TX, Bacillus subtilis Y1336 (registered as a biological fungicide in Taiwan under registration numbers 4764, 5454, 5096 and 5277, available as BIOBAC® WP from Bion-Tech, Taiwan) + TX, BASF Paenibacillus epiphyticus (International Publication No. 2016 / 020371) + TX from SE, Paenibacillus polymyxa ssp. plantarum (International Publication No. 2016 / 020371) + TX from BASF SE, Paenibacillus sp. strains with accession numbers NRRL B-50972 or NRRL B-67129, International Publication No. 2016 / 154297 + TX, Pseudomonas chlororaphis strain AFS009 (e.g., AgBiome) with accession number NRRL B-50897, International Publication No. 2017 / 019448 HOWLER (trademark) and ZIO (registered trademark) from Innovations, US) + TX, Pseudomonas chlororaphis, especially strain MA342 (e.g., CEDOMON (registered trademark), CERALL (registered trademark), and CEDRESS (registered trademark) by Bioagri and Koppert) + TX, Pseudomonas fluorescein (PseudomonasFluorescens) strain A506 (e.g., BLIGHTBAN® A506 by NuFarm) + TX, Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena) + TX, Streptomyces griseoviridis strain K61 (also known as Streptomyces galbus strain K61) (accession number DSM 7206) (MYCOSTOP® from Verdera, PREFENCE® from BioWorks, cf. Crop Protection 2006, 25, 468-475) + TX, Streptomyces lydicus strain WYEC108 (Streptomyces lydicus Lydicus (also known as strain WYCD108US) (ACTINO-IRON® and ACTINOVATE® from Novozymes) + TX, Trichoderma atroviride strain T11 (IMI352941 / CECT20498) + TX, Ampelomyces quisqualis strain AQ10 with accession number CNCM 1-807 (e.g., AQ 10® by IntrachemBio Italia) + TX, Ampelomyces quisqualis, especially strain AQ10 (e.g., AQ 10® by IntrachemBio Italia) + TX, Aspergillus flavus strain NRRL21882 (product known as AFLA-GUARD® from Syngenta / ChemChina) + TX, Aureobasidium pullulans Aureobasidium pullulans, especially budding spores of strain DSM14941 + TX, Aureobasidium pullulans, especially budding spores of strain DSM14940 + TX, Aureobasidium pullulans, especially a mixture of budding spores of strains DSM14940 and DSM14941 (e.g., Botector® by bio-ferm, CH) + TX, Chaetomium cupreum (accession number CABI353812) (e.g., BIOKUPRUM® by AgriLife) + TX, Chaetomium globosum Cladosporium cladosporioides strain H39 (by Stichting Dienst Landbouwkundig Onderzoek) +TX, accession number CBS122244, U.S. Patent Application Publication No. 2010 / 0291039, Coniothyrium minitans, in particular strain CON / M / 91-8 (accession number DSM9660, e.g. Bayer CropScience Biologics)Contans(registered trademark) from GmbH +TX, Cryptococcus flavescens, strain 3C (NRRL Y-50378) +TX, Dactylaria candida, Dilophosphora alopecuri (available as TWIST FUNGUS(registered trademark)), Fusarium oxysporum strain Fo47 (available as FUSACLEAN(registered trademark) from Natural Plant Protection) +TX, Gliocladium catenulatum (synonym: Clonostachys rosea f. catenulate) f. catenulate)) strain J1446 (e.g., Prestop® by 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), especially strain 321U from Adjuvants Plus, Xue AG (Efficacy of Clonostachys rosea strain ACM941) and fungicide seed treatments for controlling the root tot complex of field pea,Can Jour Plant SciThe strains disclosed in 2003, 83(3):519-524, Metschnikowia fructicola, in particular strain NRRLY-30752+TX, Microsphaeropsis ochracea, Penicillium steckii (DSM 27859, International Publication No. 2015 / 067800)+TX from BASF SE, Trichoderma asperellum strain ICC012 (also known as Trichoderma harzianum ICC012) with accession number CABI CC IMI 392716, and accession number IMI Trichoderma gamsii (formerly known as T. viride) strain ICC080 (e.g., BIO-TAM® from Isagro USA Inc. or BIODERMA® by Agrobiosol de Mexico, SA de CV) containing 392151 + TX, Penicillium vermiculatum + TX, Phlebiopsis gigantea strain VRA1992 (ROTSTOP® C from Danstar Ferment) + TX, Pseudozyma flocculosa strain PF-A22UL (available as SPORODEX® L from Plant Products Co., CA) + TX, Saccharomyces cerevisiae Saccharomyces cerevisiae) strain LAS117 cell wall (CEREVISANE® from Lesaffre, ROMEO® from BASF SE) + TX, Saccharomyces cerevisiae from Lesaffre et Compagnie, FRSaccharomyces cerevisiae strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938, CNCM No. 1-3939 (International Publication No. 2010 / 086790) + TX, Saccharomyces cerevisiae, especially strain LASO2 (from Agro-Levures et Derives) + TX, Simplicillium lanosoniveum + TX, strain T34 (e.g., T34 Biocontrol by Biocontrol Technologies SL,ES) or strain ICC 012 from Isagro + TX, strain WRL-076 (NRRL Y-30842), U.S. Patent No. 7,579,183 + TX, Talaromyces flavus Trichoderma flavus), strain V117b+TX, Trichoderma asperelloides JM41R (accession number NRRL B-50759) (TRICHO PLUS® from BASF SE)+TX, Trichoderma asperellum, in particular strain SKT-1 with accession number FERM P-16510 (e.g., ECO-HOPE® from Kumiai Chemical Industry)+TX, Trichoderma asperellum, in particular strain kd (e.g., T-Gro from Andermatt Biocontrol)+TX, Trichoderma atroviride strain 77B (T77 from Andermatt Biocontrol)+TX, Trichoderma atroviride (Trichoderma Trichoderma atroviride strain ATCC20476 (IMI206040) + TX, Trichoderma atroviride strain LC52 (e.g., Tenet by Agrimm Technologies Limited) + TX, Trichoderma atroviride strain LU132 (e.g., Agrimm TechnologiesSentinel (from Limited) +TX, Trichoderma atroviride strain NMI number V08 / 002388 +TX, Trichoderma atroviride strain NMI number V08 / 002389 +TX, Trichoderma atroviride strain NMI number V08 / 002390 +TX, Trichoderma atroviride strain number V08 / 002387 +TX, Trichoderma atroviride strain SKT-1 (FERM P-16510), 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 (accession number CBS 122089, International Publication No. 2009 / 116106 and U.S. Patent No. 8,431,120 (from Bi-PA)) + TX, Trichoderma atroviride, strain CNCM 1-1237 (e.g., Esquive® WP from Agrauxine, FR) + TX, Trichoderma fertil fertile) (e.g., TrichoPlus product from BASF) + TX, Trichoderma gamsii (formerly known as T. viride) + TX, Trichoderma gamsii (formerly known as T. viride) strain ICC 080 (IMI CC 392151 CABI) (available as BIODERMA® by AGROBIOSOL DE MEXICO, SADE CV) + TX, Trichoderma gamsii strain ICC080 (IMI CC 392151CABI, e.g., BioDerma)+TX by AGROBIOSOL DE MEXICO, SADE CV, Trichoderma harmatum+TX, Trichoderma harmatum+TX with accession number ATCC 28012, Trichoderma harzianum+TX, Trichoderma harzianum rifai T39 (e.g., Makhteshim Trichoderma harzianum strain Cepa SimbT5 (from Simbiose Agro) +TX, Trichoderma harzianum strain DB103 (available as T-GRO® 7456 by Dagutat Biolab) +TX, Trichoderma harzianum strain ITEM 908 (e.g., Trianum-P from Koppert) +TX, Trichoderma harzianum strain T-22 (e.g., Trianum-P from Andermatt Biocontrol or Koppert) +TX, Trichoderma harzianum Trichoderma harzianum) strain TH35 (e.g., Root-Pro by Mycontrol) + TX, Trichoderma polysporum strain IMI 206039 (e.g., Binab TF WP by BINAB Bio-Innovation AB, Sweden) + TX, Trichoderma stromaticum with accession number Ts3550 (e.g., Tricovab by CEPLAC, Brazil) + TX, Trichoderma virens (also known as Gliocladium virens), particularly strain GL-21 (e.g., SoilGard by Certis, US) + TX, Trichoderma virens strain G-41, formerly known as Gliocladium virens Also known as *Trichoderma viride* (accession number ATCC 20906) (e.g., ROOTSHIELD® PLUS WP and TURFSHIELD® PLUS WP from BioWorks, US) + TX, *Trichoderma viride*, especially 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 accession number NM99 / 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 with accession number WCS850 (e.g., DUTCH by Tree Care Innovations) TRIG(registered trademark))+TX, Verticillium chlamydosporium+TX. A mixture of Azotobacter vinelandii and Clostridium pasteurianum (available as INVIGORATE® from Agrinos) + TX, a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available as QUARTZO® (WG) and PRESENCE® (WP) from FMC Corporation) + TX, Azorhizobium caulinodans, especially strain ZB-SK-5 + TX, Azospirillum brasilense (e.g., VIGOR® from KALO, Inc.) + TX, Azospirillum lipoferum Bacillus lipoferum (e.g., VERTEX-IF® from TerraMax, Inc.) + TX, Azotobacter chroococcum, especially strain H23 + TX, Azotobacter vinelandii, especially strain ATCC12837 + TX, Bacillus amyloliquefaciens BS27 (accession number NRRL B-5015) + TX, Bacillus amyloliquefaciens, especially strain FZB42 (e.g., RHIZOVITAL® from ABiTEP, DE) + TX, Bacillus amyloliquefaciens Bacillus amyloliquefaciens), especially strain IN937a+TX, Bacillus amyloliquefaciens pm414 (LOLI-PEPTA® from Biofilm Crop Protection)+TX, Bacillus amyloliquefaciensBacillus amyloliquefaciens)SB3281 (ATCC#PTA-7542, International Publication No. 2017 / 205258) + TX, Bacillus amyloliquefaciens TJ1000 (available as QUIKROOTS® from Novozymes) + TX, Bacillus cereus family member EE128 (NRRL No. B-50917) + TX, Bacillus cereus family member EE349 (NRRL No. B-50928) + TX, Bacillus cereus, in particular strain BP01 (ATCC55675, e.g., MEPICHLOR® from Arysta Lifescience, US) + TX, Bacillus mycoides Bacillus mycoides BT155 (NRRL number B-50921) + TX, Bacillus mycoides BT46-3 (NRRL number B-50922) + TX, Bacillus mycoides EE118 (NRRL number B-50918) + TX, Bacillus mycoides EE141 (NRRL number B-50916) + TX, Bacillus pumilus, especially strain GB34 (e.g., YIELD SHIELD® from Bayer Crop Science, DE) + TX, Bacillus pumilus, especially strain QST2808 (accession number NRRL number B-30087) + TX, Bacillus siamensis Bacillus subtilis, particularly strain KCTC 13613T+TX, Bacillus subtilis, particularly strain AQ30002 (accession number B-50421 and U.S. Patent Publication No. 13 / 330,576)+TX, Bacillus subtilis, particularly strain AQ30004 (NRRL number B-50455 and U.S. Patent Publication No. 13 / 330,576)+TX, Bacillus subtilis, particularly strain MBI600 (e.g., SUBTILEX® from BASF SE) + TX, Bacillus subtilis rm303 (RHIZOMAX® from Biofilm Crop Protection) + TX, Bacillus subtilis strain BU1814 (available as TEQUALIS® from BASF SE) + TX, Bacillus tequilensis, especially strain NII-0943 + TX, Bacillus thuringiensis BT013A (NRRL number B-50924), also known as Bacillus thuringiensis 4Q7 + TX, Bradyrhizobium japonica japonicum) (e.g., OPTIMIZE® from Novozymes) + TX, Delftia acidovorans, especially strain RAY209 (e.g., BIOBOOST® from Brett Young Seeds) + TX, Lactobacillus sp. (e.g., LACTOPLANT® from LactoPAFI) + TX, Mesorhizobium cicer (e.g., NODULATOR from BASF SE) + TX, Paenibacillus polymyxa, especially strain AC-1 (e.g., TOPSEED® from Green Biotech Company Ltd.) + TX, Pseudomonas aeruginosa, especially strain PN1 + TX, Pseudomonas proradicus proradix) (e.g., PRORADIX® from Sourcon Padena) + TX, Rhizobium leguminosarium biovar viciae (e.g., NODULATOR from BASF SE) + TX, Rhizobium leguminosariumLeguminosarum), especially bv. viceae strain Z25 (accession number CECT 4585) + TX, Serratia marcescens, especially strain SRM (accession number MTCC 8708), + TX, Sinorhizobium meliloti strain NRG-185-1 (NITRAGIN® GOLD from Bayer CropScience) + TX, Thiobacillus sp. (e.g., CROPAID® from Cropaid Ltd UK) + TX, Myrothecium verrucaria strain AARC-0255 (e.g., DiTera® from Valent Biosciences) + TX, Penicillium bilaii strain ATCC22348 (e.g., JumpStart® from Acceleron BioAg) + TX, Penicillium bilaii strain ATCC ATCC20851 + TX, Purpureocillium lilacinum (formerly known as Paecilomyces lilacinus) strain 251 (AGAL89 / 030550, e.g., BioAct from Bayer CropScience Biologics GmbH) + TX, Pythium origandrum Pythium oligandrum strain DV74+TX, Pythium oligandrum strain M1 (ATCC 38472, e.g., Polyversum from Bioprepraty, CZ)+TX, Rhizopogon amylopogon (Myco-Sol from Agri-Enterprise, LLC, formerly Helena Chemical Company)+TX, Rhizopogon fulvigleba (Myco-Sol from Agri-Enterprise, LLC, formerly Helena Chemical Company)+TX, Talaromyces flavus strain V117b+TX, Trichoderma asperellum strain (Plant Health Products,Eco-T)+TX from ZA, Trichoderma asperellum strain kd (e.g., T-Gro from Andermatt Biocontrol)+TX, Trichoderma atroviride, specifically strain number V08 / 002387+TX, Trichoderma atroviride strain CNCM1-1237 (e.g., Esquive® WP from Agrauxine, FR)+TX, Trichoderma atroviride strain LC52 (also known as Trichoderma atroviride strain LU132, e.g., Sentinel from Agrimm Technologies Limited)+TX, Trichoderma atroviride Trichoderma atroviride strain number NMI number V08 / 002388+TX, Trichoderma atroviride strain number NMI number V08 / 002389+TX, Trichoderma atroviride strain number NMI number V08 / 002390+TX, Trichoderma atroviride strain SC1 (described in International Publication No. 2009 / 116106)+TX, Trichoderma harzianum strain 1295-22+TX, Trichoderma harzianum strain ITEM 908+TX, Trichoderma harzianum strain T-22 (e.g., Andermatt Biocontrol or Koppert's Trianum-P)+TX, Trichoderma harzianum strain TSTh20,+TX, Trichoderma virens strain GI-3+TX, Trichoderma virens strain GL-21 (e.g., Certis,SoilGard® (registered trademark) + TX from the USA, Trichoderma viride strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161:125-137) + TX, Verticillium albo-atrum (formerly V. dahliae) strain WCS850 (CBS276.92, e.g., Dutch Trig from 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 islaerensis Bacillus thuringiensis subsp. aizawai strain BMP144 (e.g., AQUABAC® by 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. aizawai Bacillus thuringiensis subsp. (israelensis) (serotype H-14) strain AM65-52 (accession number ATCC 1276) (e.g., VECTOBAC® by Valent BioSciences, US) + TX, Bacillus thuringiensis subsp.Bacillus thuringiensis subsp. kurstaki strain ABTS 351 + TX, Bacillus thuringiensis subsp. kurstaki strain BMP123 (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 (e.g., Valent From BioSciences, US: DIPEL(registered trademark) ES) + TX, Bacillus thuringiensis subsp. kurstaki strain PB 54 + TX, Bacillus thuringiensis subsp. kurstaki strain SA11 (JAVELIN from Certis, US) + TX, Bacillus thuringiensis subsp. kurstaki strain SA 12 (THURICIDE from Certis, US) + TX, Bacillus thuringiensis subsp. tenebrionis strain NB176 (SD-5428, e.g., NOVODOR(registered trademark) FC from BioFa DE) + TX, Bacillus thuringiensis variety Colmeli (Bacillus Bacillus thuringiensis var. Colmeri) (e.g., TIANBAOBTC by Changzhou Jianghai Chemical Factory) + TX, Bacillus thuringiensis var. japonensisBacillus thuringiensis var. kurstaki strain EVB-113-19 (e.g., BIOPROTEC® from AEF Global) +TX, Brevibacillus laterosporus +TX, Burkholderia spp., especially Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis strain MBI305) (accession number NRRL B-50319, international publications 2011 / 106491 and 2013 / 032693, e.g., MBI206 from Marrone Bio Innovations) TGAI and ZELTO (registered trademarks), +TX, Chromobacterium subtsugae, especially strain PRAA4-1T (e.g., MBI-203, e.g., GRANDEVO (registered trademark) from Marrone Bio Innovations) +TX, Lecanicillium muscarium Ve6 (MYCOTAL from Koppert) +TX, Paenibacillus popilliae (formerly known as Bacillus popilliae, e.g., St.From Gabriel Laboratories: MILKY SPORE POWDER (trademark) or MILKY SPORE GRANULAR (trademark) + TX, Serratia entomophila (e.g., INVADE (registered trademark) by Wrightson Seeds) + TX, Serratia marcescens, especially strain SRM (accession number MTCC8708) + TX, Trichoderma asperellum (TRICHODERMAX from Novozymes) + TX, Wolbachia pipientis ZAP strain (e.g., ZAP MALES (registered trademark) from MosquitoMate) + TX, etc. Beauveria bassiana strain ATCC 74040 (e.g., NATURALIS® from Intrachem Bio Italia) + TX, Beauveria bassiana strain ATP02 (accession number DSM24665), Apopka 97 (PREFERAL from SePRO) + TX, Beauveria bassiana strain GHA (accession number ATCC74250, e.g., BOTANIGUARD® ES and MYCONTROL-O® from Laverlam International Corporation) + TX, Metarhizium anisopliae 3213-1 (deposited under NRRL accession number 67074 disclosed in International Publication No. 2017 / 066094, Pioneer Hi-Bred International) +TX, Metarhizium robertsii 15013-1 (deposited under NRRL accession number 67073) +TX, Metarhizium robertsii 23013-3 (deposited under NRRL accession number 67075) +TX, Paecilomyces lilacinus strain 251 (MELOCON from Certis, US) +TX, Cydia pomonella (codlinga) granuloma virus (GV) + TX, Helicoverpa armigera (tobacco budworm) nuclear polyhedra disease virus (NPV) + TX, Adoxophyes orana (apple tortrix moth) granuloma virus (GV) + TX, Spodoptera exigua (white-striped armyworm) mNPV + TX, Spodoptera frugiperda (white-striped 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 tinctorus + TX, Pseudomonas spp. + TX, Rhizobium spp., especially Rhizobium trifolii trifolii)+TX, Rhizopogon spp.+TX, Scleoderma spp.+TX, Streptomyces spp.+TX, Suillus spp.+TX, Agrobacterium spp.+TX, Azorhizobium caulinodans+TX, Azospirillum spp.+TX, Azotobacter spp.+TX, Bradyrhizobium spp.+TX, Gigaspora monosporum+TX, Allium sativum (NEMGUARD from Eco-Spray, BRALIC from ADAMA) + TX, 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,Heads Up (quinoa saponin) + TX from CA, Chitin + TX, Dryopteris filix-mas + TX, Equisetum arvense + TX, Fortune Aza + TX, Fungastop + TX, Melaleuca alternifolia extract (TIMOREX GOLD from STK) + TX, Natural Blad polypeptide extracted from Japanese bean seeds (FRACTURE (registered trademark) from FMC) + TX, Natural Blad polypeptide extracted from Japanese bean seeds (PROBLAD (registered trademark) from Certis EU) + TX, Pyrethrin + TX, Quassia amara + TX, Quercus + TX, Quillaja extract (QL AGRI 35 from BASF) + TX, REGALIA from Marrone Bio MAXX)+TX, Requiem(trademark) insecticide+TX, Reynoutria sachalinensis extract (REGALLIA+TX, liany / lianodine+TX, Symphytum officinale+TX, Tanacetum vulgare+TX, Thymol+TX, Thymol mixed with geraniol (CEDROZ from Eden Research)+TX, Thymol mixed with geraniol and eugenol (MEVALONE from Eden Research)+TX, Triact 70+TX, TriCon+TX, Tropaeulum majus+TX, Urtica dioica+TX, Veratrin+TX, Viscum album+TX, Mercuric oxide + TX, Octylinone + TX, Thiophanate-methyl + TX, MGK 264+TX, 2-(2-butoxyethoxy)ethylpiperonilate+TX, 2-isovalerylindan-1,3-dione+TX, 4-(quinoxaline-2-ylamino)benzenesulfonamide+TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohexy-2-enone+TX, acibenzolar+TX, acibenzolar-S-methyl+TX, alpha-bromadiolone+TX, alpha-chlorohydrin+TX, aluminum phosphide+TX, anthraquinone+TX, antz+TX, arsenous acid+TX, barium carbonate+TX, benox Sacol + TX, Bisthiosemi + TX, Brodiphacum + TX, Bromadiolon + TX, Bromethalin + TX, Calcium cyanide + TX, Chloralose + TX, Chlorophacinone + TX, Cholecalciferol + TX, Croquintocet (including Croquintocet-Mexyl) + TX, Copper naphthenate + TX, Copper oxychloride + TX, Coumaflyryl + TX, Coumatetralyl + TX, Crimidine + TX, Cyprosulfamide + TX, Diazinon + TX, Dichlormid + TX, Dicyclopentadiene + TX, Diphenacum + TX, Dife Thiaron + TX, Difacinone + TX, Ergocalciferol + TX, Farnesol + TX, Farnesol and Nerolidol + TX, Fenchlorazole (including fenchlorazole-ethyl) + TX, Fenchlorim + TX, Furocumafen + TX, Fluoroacetamide + TX, Flupropazine + TX, Flupropazine hydrochloride + TX, Fluxofenim + TX, Frillazole + TX, Gamma-HCH + TX, Guazatine + TX, Guazatine acetate + TX, HCH + TX, Hydrogen cyanide + TX, Imanin + TX, Iodomethane + TX, Isoxadi Fen (containing isoxadiphen-ethyl) + TX, Lindan + TX, Magnesium phosphide + TX, MB599 + TX, Mefenyphen (containing mefenyphen-diethyl) + TX, Metocamifen + TX, Methiocarb + TX, Methyl bromide + TX, Nerolidol + TX, Norbolmid + TX, Petroleum + TX, Fosacetim + TX, Phosphine + TX, Phosphate + TX, Phosphate + TX, Pindone + TX, Piperonyl butoxide + TX, Piprotal + TX, Potassium arsenite + TX, Probenazole + TX, Propyl isomer + TX, Pyridine-4-amine + TX, Pyrynulone + TX,Reynoutria sachalinensis extract + TX, ribavirin + TX, S421 + TX, siriloside + TX, sesamex + TX, 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.

[0209] In addition, the compositions of the present invention may be administered together with one or more systemic acquired resistance inducers ("SAR" inducers). SAR inducers are known and described, for example, in U.S. Patent No. 6,919,298, and include, for example, salicylates and the commercially available SAR inducer acibenzolar-S-methyl.

[0210] The compounds of formula (I) as defined in this invention are typically used in the form of compositions and may be applied simultaneously with or consecutively to a planted area or treated plant with further compounds. These further compounds may be, for example, fertilizers or sources of trace elements or other preparations that affect plant growth. These may also be selective or non-selective herbicides, as well as insecticides, fungicides, bactericidal agents, nematicides, molluskicides, or mixtures thereof, and may include, as necessary, further carriers, surfactants, or application enhancers commonly used in the art of formulations.

[0211] The compounds of formula (I) as defined in the present invention may be used in the form of (fungicidal) compositions for the control or protection of plant pathogenic microorganisms, comprising as an active ingredient at least one of the compounds of formula (I) as defined in the present invention or at least one of the preferred individual compounds defined above and at least one of the above-mentioned auxiliary agents in free form or in agrochemically usable salt form.

[0212] Accordingly, the present invention provides a composition, preferably a fungicidal composition, comprising at least one compound of formula (I) as defined in the present invention, an agriculturally acceptable carrier, and optionally an auxiliary agent. The agriculturally acceptable carrier is, for example, a carrier suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, the composition may, in addition to the compound of formula (I) as defined in the present invention, comprise at least one or more pesticide compounds, such as additional fungicidal active ingredients.

[0213] Further aspects of the present invention relate to methods for controlling or preventing ectoparasitism of plants, such as useful plants, such as crop plants, their reproductive materials, such as seeds, harvested crops, such as harvested food crops, or non-biological materials, by plant pathogenic or putrefactive microorganisms or organisms, particularly fungi, which may be harmful to humans, and the methods include the application of a compound of formula (I) as defined in the present invention or any part of the preferred individual compounds as defined above, as an active ingredient for plants, to a plant, a part of a plant or its habitat, its reproductive material, or non-biological material.

[0214] Control or prevention means reducing ectopic parasitism by insects, plant pathogenic or putrefactive microorganisms, or organisms potentially harmful to humans, particularly fungi, to a level where improvement is demonstrated.

[0215] A preferred method for controlling or preventing ectoparasitism of crop plants by plant pathogenic microorganisms, particularly fungi, is foliar application, which involves the application of a pesticide composition containing a compound of formula (I) as defined in the present invention or at least one of said compounds. The frequency and amount of application will depend on the risk of ectoparasitism by the corresponding pathogen or insect. However, the compound of formula (I) as defined in the present invention can also be introduced into plants through the soil via the roots (osmotic action) by drenching the plant habitat with a liquid formulation or by applying the compound to the soil in solid form, such as granular form (soil application). In rice crops, such granular material can be applied to flooded paddy fields. The compound of formula (I) as defined in the present invention can be applied to seeds (coating) by either impregnating the seeds or tubers with a liquid formulation of the fungicide or coating them with a solid formulation.

[0216] Formulations, such as compositions containing a compound of formula (I) as defined in the present invention and, optionally, a solid or liquid additive or a monomer for encapsulating the compound of formula (I) as defined in the present invention, can be prepared by known methods, typically by closely mixing and / or grinding the compound with an expander, such as a solvent, a solid carrier, and optionally a surfactant.

[0217] Methods of application for this composition, i.e., spraying, misting, dusting, brushing, powdering, diffusion, or pouring (these should be selected according to the intended purpose of the general situation), methods for controlling the above-mentioned types of pathogens, and the use of the composition for controlling the above-mentioned types of pathogens are other 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.

[0218] When the combination of the present invention is used for seed treatment, an amount of 0.001 to 50 g of the compound of formula (I) per 1 kg of seed, preferably 0.01 to 10 g per 1 kg of seed, is generally considered sufficient.

[0219] Preferably, a composition comprising the compound of formula (I) according to the present invention as defined herein is administered either preventively (meaning before the onset of disease) or therapeutically (meaning after the onset of disease).

[0220] The compositions of the present invention may be any of the conventional forms, for example, a two-component system, a dry seed treatment powder (DS), a seed treatment emulsion (ES), a seed treatment fluid concentrate (FS), a seed treatment solution (LS), a seed treatment water-dispersible powder (WS), a seed treatment capsule suspension (CF), a seed treatment gel (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspension emulsion (SE), a capsule suspension (CS), water-dispersible granules (WG), or emulsifying granules. It 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 in combination with agriculturally acceptable adjuvants.

[0221] Such compositions can be produced by conventional methods, for example, by mixing an active ingredient with a suitable formulation inert component (diluent, solvent, filler, and optionally other formulation components such as surfactants, biocides, antifreezes, spreading agents, thickeners, and compounds that provide auxiliary effects). Conventional sustained-release formulations can also be used when sustained efficacy over a long period is desired. In particular, formulations intended for application in spray form, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules, may contain surfactants such as wetting agents and dispersants, as well as other compounds that provide auxiliary effects, such as formaldehyde, and condensation products of naphthalene sulfonates, alkylaryl sulfonates, lignin sulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0222] The seed coating formulation is applied to seeds in a manner known in itself, using the combination and diluent of the present invention, in a preferred seed coating formulation form, for example, as an aqueous suspension or in a dry powder form having good adhesion to seeds. Such seed coating formulations are known in the art. The seed coating formulation may contain a single active ingredient or a combination of active ingredients in encapsulated form, for example, as a slow-release capsule or microcapsule.

[0223] Generally, the formulations contain 0.01 to 90% by weight of an activator, 0 to 20% of an agriculturally acceptable surfactant, and 10 to 99.99% of solid or liquid formulation inert components and auxiliary agents, components (B) and (C), along with an activator consisting of at least one compound of formula (I) as defined in the present invention and optionally other activators, particularly microbiotacitists or preservatives. The concentrate form of the composition generally contains about 2 to 80%, preferably about 5 to 70% by weight of the activator. The application form of the formulation may contain, for example, 0.01 to 20% by weight, preferably 0.01 to 5% by weight of the activator. Commercial products are preferably formulated as concentrates, but end users typically use diluted formulations.

[0224] While it is preferable to formulate commercially available products as concentrates, end users typically utilize dilute formulations. [Examples]

[0225] The following examples illustrate the present invention. Certain compounds of the present invention may be distinguished from known compounds by their greater potency at lower doses, which can be verified by those skilled in the art using the experimental procedures outlined in the examples.

[0226] [Table 2]

[0227] By thoroughly mixing the active ingredient with an auxiliary agent and thoroughly grinding the mixture in a suitable pulverizer, a wettable powder can be obtained that can be diluted with water to form a suspension of the desired concentration.

[0228] [Table 3]

[0229] The active ingredient is thoroughly mixed with an auxiliary agent, and the mixture is thoroughly ground in a suitable grinder to obtain a powder that can be used directly for seed treatment.

[0230] emulsifiable concentrate Active ingredient [compound of formula (I)] 10% Octylphenol polyethylene glycol ether (ethylene oxide 4-5 mol) 3% Calcium dodecylbenzenesulfonate 3% Castor oil polyglycol ether (ethylene oxide 35 mol) 4% Cyclohexanone 30% Xylene mixture 50%

[0231] Any required dilution of emulsion that can be used for plant protection can be obtained by diluting this concentrate with water.

[0232] [Table 4]

[0233] Ready-to-use powders are obtained by mixing the active ingredient with a carrier and grinding the mixture in a suitable pulverizer. Such powders can also be used for drying and coating seeds.

[0234] Extruded granules Active ingredient [compound of formula (I)] 15% Sodium lignin sulfonate 2% Carboxymethylcellulose 1% Kaolin 82%

[0235] The active ingredient is mixed with an auxiliary agent and ground, and the mixture is moistened with water. The mixture is then extruded and dried in an airflow.

[0236] Coated granules Active ingredient [compound of formula (I)] 8% Polyethylene glycol (molecular weight 200) 3% Kaolin 89%

[0237] The finely ground active ingredient is uniformly applied in a mixer to kaolin moistened with polyethylene glycol. A non-dusting coated granule is thus obtained.

[0238] Suspension concentrate Active ingredient [compound of formula (I)] 40% Propylene glycol 10% Nonylphenol polyethylene glycol ether (ethylene oxide 15 mol) 6% Sodium lignin sulfonate 10% Carboxymethylcellulose 1% Silicone oil (in the form of a 75% emulsion in water) 1% water 32%

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

[0240] Flowable formulation for seed treatment Active ingredient [compound of formula (I)] 40% Propylene glycol 5% Copolymer Butanol PO / EO 2% Tristyrenephenol 2% with 10-20 moles of EO 1,2-Benzisothiazolin-3-one (20% aqueous solution) 0.5% Monoazo pigment calcium salt 5% Silicone oil (in the form of a 75% emulsion in water) 0.2% Water 45.3%

[0241] By thoroughly mixing the finely ground active ingredient with an auxiliary agent, a suspension concentrate can be obtained, which can then be diluted with water to obtain a suspension of any desired dilution. Using such dilutions, not only growing plants but also plant propagation materials can be treated by spraying, pouring, or immersion to protect them from microbial ectoparasitism.

[0242] 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.

[0243] The resulting capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersant. The capsule suspension formulation contains 28% of the active ingredient. The diameter of the capsules is 8 to 15 microns.

[0244] The resulting formulation is applied to seeds as an aqueous suspension using equipment suitable for the purpose.

[0245] Analysis method Throughout this specification, temperatures are expressed in degrees Celsius (°C), and "mp" indicates the melting point. LC / MS refers to liquid chromatography-mass spectrometry, and the apparatus and method are described below.

[0246] Method A: Spectra were recorded using the following: a mass spectrometer from Waters Corporation (SQD, SQDII, or QDA single quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive and negative ions), capillary voltage: 0.8–3.00kV, cone voltage: 5–30V, source temperature: 120–150°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 an Acquity UPLC from Waters Corporation: 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 uniform concentration 0.2 min, then 10 to 100% B 1.0 min, 100% B uniform concentration 0.2 min, 100 to 10% B 0.05 min, 10% B uniform concentration 0.05 min.

[0247] Method B: Spectra were recorded using the following: an ACQUITY mass spectrometer (SQD or SQDII single quadrupole mass spectrometer) from Waters Corporation equipped with an electrospray source (polarity: positive or negative ions, capillary voltage: 3.0kV, cone voltage: 30V, extractor voltage: 3.00V, source temperature: 150°C, desolvation temperature: 400°C, cone gas flow rate: 60L / hr, 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.

[0248] Method C: Spectra were recorded using the following equipment: Agilent mass spectrometer with electrospray (single quadrupole mass spectrometer) (polarity: cations and anions), capillary: 4.00kV, charging voltage: 2.00kV, nitrogen gas flow rate: 12.0L / min, nebulizer pressure: 40psig, mass range: 100~1000m / z, dry gas temperature: 250℃, vaporizer temperature: 200℃, and Waters UPLC: quaternary pump, heated column compartment, tunable wavelength detector. Column: Kinetex Evo_50mm, 1.7μm (2.1*50mm), column temperature: ambient, wavelength (nm): 200~400nm, gradient: A=acetonitrile, B=10mM ammonium formate in water. Gradient time / %A: 0 / 2, 0.2 / 2, 1.5 / 45, 2.4 / 95, 3.3 / 2, 3.5 / 2; Flow rate: 0.5 mL / min.

[0249] Table A below summarizes the compounds of formula (I): - LC / MS data, e.g., retention time (RT), [M+H] + etc. - Type of method, and / or - Melting point (mp).

[0250] [Table 5-1]

[0251] [Table 5-2]

[0252] [Table 5-3]

[0253] [Table 5-4]

[0254] [Table 5-5]

[0255] [Table 5-6]

[0256] [Table 5-7]

[0257] [Table 5-8]

[0258] [Table 5-9]

[0259] [Table 5-10]

[0260] [Table 5-11]

[0261] Example 1: Preparation of methyl N-[5-[5-[(4-fluoro-3-methoxyphenyl)-(methoxymethyl)carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate (Compound 1) [ka] Step A: Preparation of N-(4-fluoro-3-methoxyphenyl)pyrazolo[1,5-a]pyridine-5-carboxamide [ka] Triethylamine (3.43 mL, 24.6 mmol, 3.00 equivalents), followed by 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (4.68 g, 12.3 mmol, 1.50 equivalents), was added to an ice-cold solution of pyrazolo[1,5-a]pyridinium-5-carboxylic acid (CAS 104468-87-3, 1.40 g, 8.20 mmol) and 4-fluoro-3-methoxyaniline (1.74 g, 12.3 mmol, 1.50 equivalents) in dimethylformamide (15.0 mL). 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 dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain N-(4-fluoro-3-methoxyphenyl)pyrazolo[1,5-a]pyridine-5-carboxamide as a grayish-white, cottony solid. 1 H-NMR (400MHz, DMSO-d 6,ppm)δ=3.84(s,3H),6.88(dd,1H),7.19-7.22(m,1H),7.31-7.40(m,2H),7. 62-7.71(dd,1H),8.13(s,1H),8.39(s,1H),8.80-8.83(m,1H),10.45(s,1H)

[0262] Step B: Preparation of N-(4-fluoro-3-methoxyphenyl)-N-(methoxymethyl)pyrazolo[1,5-a]pyridine-5-carboxamide [ka] To an ice-cold solution of N-(4-fluoro-3-methoxyphenyl)pyrazolo[1,5-a]pyridine-5-carboxamide (0.500 g, 1.58 mmol) in dried tetrahydrofuran (10.0 mL), 60% sodium hydride in oil (0.189 g, 7.89 mmol, 5.00 equivalents) was added under nitrogen. After stirring for 30 minutes, chloro(methoxy)methane (0.254 g, 3.15 mmol, 2.00 equivalents) was added, and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was cooled to 0°C, quenched with crushed ice, and diluted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain N-(4-fluoro-3-methoxyphenyl)-N-(methoxymethyl)pyrazolo[1,5-a]pyridine-5-carboxamide as a grayish-white, rubbery solid. LC-MS (Method C): Rt 3.32min, m / z=330(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=3.36(s,3H),3.75(s,3H),5.15(2H),6.68(dd,1H),6.72-6.82(m,2H),7.0 8-7.13(m,1H),7.20-7.24(dd,1H),7.79(s,1H),8.01(dd,1H),8.56-8.61(dd,1H)

[0263] Step C: Preparation of N-(4-fluoro-3-methoxyphenyl)-3-iodo-N-(methoxymethyl)pyrazolo[1,5-a]pyridine-5-carboxamide [ka] N-iodosuccinimide (0.122 g, 0.541 mmol, 1.10 equivalents) was added to a solution of N-(4-fluoro-3-methoxy-phenyl)-N-(methoxymethyl)pyrazolo[1,5-a]pyridine-5-carboxamide (0.180 g, 0.492 mmol) in dimethylformamide (2.00 mL). 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 dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain N-(4-fluoro-3-methoxy-phenyl)-3-iodo-N-(methoxymethyl)pyrazolo[1,5-a]pyridine-5-carboxamide as a grayish-white, rubbery solid. LC-MS (Method C): Rt 4.00min, m / z=456(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=3.38(s,3H),3.78(s,3H),5.18(s,2H),6.80-6.90(m,2H),7.05-7.15( m,1H),7.30-7.33(dd,1H),7.50-7.60(s,1H),8.13(s,1H),8.60-8.70(dd,1H)

[0264] Step D: Preparation of methyl N-[5-[5-[(4-fluoro-3-methoxyphenyl)-(methoxymethyl)carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate (compound 1) To a solution of N-(4-fluoro-3-methoxyphenyl)-3-iodo-N-(methoxymethyl)pyrazolo[1,5-a]pyridine-5-carboxamide (0.400 g, 0.835 mmol.) and methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (0.284 g, 1.00 mmol, 1.20 equivalents) in 1,4-dioxane:water (3:1, 5.00 mL), cesium carbonate (0.544 g, 1.67 mmol, 2.00 equivalents) was added, and the mixture was purged with an argon stream for 2 minutes. Under an N2 atmosphere, cataCXium® A Pd G3 (CAS 1651823-59-4) (0.0304 g, 0.0417 mmol, 0.05 equivalents) was added to the reaction mixture. The resulting reaction mixture was microwaved 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, then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified on a silica gel cartridge (dichloromethane / methanol) to obtain methyl N-[5-[5-[(4-fluoro-3-methoxyphenyl)-(methoxymethyl)carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate as a yellow solid. LC-MS (Method C): Rt 3.31min, m / z=480(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=3.38(s,3H),3.70(s,3H),3.78(s,3H),5.19(s,2H),6.80-6.87(m,1H),6.88-6.93(m,1H),7.07-7.13(m,1H) ,7.31-7.40(m,1H),7.83-7.90(m,1H),7.90-7.97(m,2H),8.42(s,1H),8.51(s,1H),8.60-8.70(m,1H),10.25(s,1H)

[0265] Example 2: Preparation of methyl N-[5-[5-[(4-chloro-3-methoxyphenyl)-(cyanomethyl)carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate (Compound 2) [ka] Step A: Preparation of methylpyrazolo[1,5-a]pyridine-5-carboxylate [ka] A solution of pyrazolo[1,5-a]pyridine-5-carboxylic acid (CAS104468-87-3, 3.50 g, 22.0 mmol) in methanol (88 mL) was mixed with concentrated sulfuric acid (0.12 mL, 2.2 mmol, 0.10 equivalents). The reaction mixture was stirred under reflux temperature for 16 hours. The reaction mixture was diluted in water and ethyl acetate and basicized to pH 8 with sodium bicarbonate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to obtain a beige solid of methylpyrazolo[1,5-a]pyridine-5-carboxylate. LC-MS (Method C): Rt 0.74min, m / z=177(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=3.93-4.02(m,3H),6.68-6.80(m,1H),7.30-7.37(m,1H),7.99-8.08(m,1H),8.31-8.37(m,1H),8.46-8.54(m,1H)

[0266] Step B: Preparation of methyl 3-bromopyrazolo[1,5-a]pyridine-5-carboxylate [ka] N-bromosuccinimide (3.1 g, 18 mmol, 1.0 equivalent) was added in fractions to a solution of methylpyrazolo[1,5-a]pyridine-5-carboxylate (3.50 g, 14.0 mmol) in acetonitrile (85 mL). The reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was quenched with sodium thiosulfate solution and then extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (dichloromethane / methanol) to obtain a white solid of methyl 3-bromopyrazolo[1,5-a]pyridine-5-carboxylate. LC-MS (Method C): Rt 0.93min, m / z=255 / 257(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=3.94-4.05(m,3H),7.35-7.43(m,1H),7.96-8.08(m,1H),8.24-8.34(m,1H),8.39-8.50(m,1H)

[0267] Step C: Preparation of 3-bromopyrazolo[1,5-a]pyridine-5-carboxylic acid (compound X-1) [ka] Lithium hydroxide (0.293 g, 11.8 mmol, 2.00 equivalents) was added to a solution of methyl 3-bromopyrazolo[1,5-a]pyridine-5-carboxylate (1.50 g, 5.88 mmol) in water (5.88 mL) and tetrahydrofuran (17.6 mL). The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was adjusted to pH 4 with 1N hydrochloric acid, diluted with water, and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to obtain 3-bromopyrazolo[1,5-a]pyridine-5-carboxylic acid. LC-MS (Method C): Rt 0.74min, m / z=241 / 243(M+H) + 1 H-NMR (400MHz, DMSO-d 6,ppm)δ=7.17-7.46(m,1H),7.98-8.20(m,1H),8.26-8.37(m,1H),8.72-8.88(m,1H),13.38-13.70(m,1H)

[0268] Step D: Preparation of 2-(4-chloro-3-methoxy-anilino)acetonitrile [ka] To a solution of 4-chloro-3-methoxyaniline (10.5 g, 10 mmol) in acetonitrile (19 mL), 2-bromoacetonitrile (1.40 mL, 20.0 mmol, 2.00 equivalents), sodium iodide (0.710 g, 4.80 mmol, 0.50 equivalents), and potassium carbonate (1.600 g, 11.00 mmol, 1.20 equivalents) were added. The reaction mixture was stirred at room temperature for 16 hours, then stirred under reflux for 6 hours. The reaction mixture was filtered, diluted with 2 M sodium hydroxide, and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain 2-(4-chloro-3-methoxyanilino)acetonitrile as a brown oily substance. LC-MS (Method C): Rt 0.80min, 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),7.22-7.26(m,1H)

[0269] Step E: Preparation of 3-bromo-N-(4-chloro-3-methoxyphenyl)-N-(cyanomethyl)pyrazolo[1,5-a]pyridine-5-carboxamide [ka] A solution of 2-(4-chloro-3-methoxyanilino)acetonitrile (0.150 g, 0.763 mmol), 3-bromopyrazolo[1,5-a]pyridine-5-carboxylic acid (compound X-1) (0.209 g, 0.839 mmol, 1.10 equivalents), and N-ethyl-N-isopropyl-propan-2-amine (0.522 mL, 3.05 mmol, 4.00 equivalents) in ethyl acetate was prepared by adding 50% 1-propanephosphonic anhydride (0.500 mL, 0.839 mmol, 1.10 equivalents) in ethyl acetate. The reaction mixture was stirred at 85°C for 16 hours. The reaction mixture was diluted with ethyl acetate and quenched with water. The combined organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain 3-bromo-N-(4-chloro-3-methoxyphenyl)-N-(cyanomethyl)pyrazolo[1,5-a]pyridine-5-carboxamide as a yellow, rubbery substance. LC-MS (Method C): Rt 0.98min, m / z=419(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=3.85(s,3H),4.78(s,2H),6.73(dd,J=7.27,1.82Hz,1H),6.78-6.83(m ,2H),7.35-7.42(m,1H),7.71(dd,J=1.82,0.73Hz,1H),7.96(s,1H),8.26(dd,J=7.27,0.73Hz,1H).

[0270] Step F: Preparation of methyl N-[5-[5-[(4-chloro-3-methoxyphenyl)-(cyanomethyl)carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate (compound 2) A mixture of 3-bromo-N-(4-chloro-3-methoxyphenyl)-N-(cyanomethyl)pyrazolo[1,5-a]pyridine-5-carboxamide (0.074 g, 0.18 mmol), methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (0.069 g, 0.25 mmol, 1.4 equivalents), and cesium carbonate (0.086 g, 0.26 mmol, 1.50 eq.) in 2-methyltetrahydrofuran (1.1 mL) was flushed with argon for 5 minutes. Next, tetrakis(triphenylphosphine)palladium(0) (0.011 g, 0.0088 mmol, 0.050 eq.) was added, and the reaction mixture was heated at 100°C under microwave irradiation for 30 minutes. The reaction mixture was cooled to room temperature, and then water was added. The aqueous layer was extracted with ethyl acetate, the combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified in a silica gel cartridge (cyclohexane / ethyl acetate) to obtain methyl N-[5-[5-[(4-chloro-3-methoxyphenyl)-(cyanomethyl)carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate as a beige solid. LC-MS (Method C): Rt 0.91min, m / z=491(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=3.86(s,3H),3.88(s,3H),4.78(s,2H),6.78-6.88(m,3H),7.42(d,J=8.36Hz,1H),7.61(dd,J=8.72,2.54Hz,1H),7.67(br d,J=1.45Hz,1H),7.77-7.86(m,1H),8.09(d,J=8.72Hz,1H),8.14(s,1H),8.32(d,J=1.00Hz,1H),8.37(d,J=7.27Hz,1H)

[0271] Example 3: Preparation of methyl N-[5-[5-[cyanomethyl-(4-fluoro-3-methoxyphenyl)carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate (compound 3) [ka] Step A: Preparation of 2-(4-fluoro-3-methoxy-anilino)acetonitrile [ka] To a solution of 4-fluoro-3-methoxy-aniline (1.5 g, 11 mmol) in acetonitrile (21 mL), 2-bromoacetonitrile (0.78 mL, 11 mmol, 1.1 equivalents), sodium iodide (0.800 g, 5.30 mmol, 0.50 equivalents), and potassium carbonate (1.80 g, 13.0 mmol, 1.20 equivalents) were added. The reaction mixture was stirred at reflux temperature for 16 hours. The reaction mixture was filtered, diluted with ethyl acetate, and quenched with a saturated solution of sodium bicarbonate. The combined organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain 2-(4-fluoro-3-methoxy-anilino)acetonitrile as a grayish-white solid. LC-MS (Method C): Rt 0.71min, m / z=181(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=3.79-3.85(m,1H),3.86(s,3H),4.07(d,J=6.90Hz,2H),6.40-6.49(m,1H),6.51-6.60(m,1H),6.87-6.98(m,1H).

[0272] Step B: Preparation of 3-bromo-N-(cyanomethyl)-N-(4-fluoro-3-methoxyphenyl)pyrazolo[1,5-a]pyridine-5-carboxamide [ka] To a solution of 2-(4-fluoro-3-methoxy-anilino)acetonitrile (0.150 g, 0.833 mmol), 3-bromopyrazolo[1,5-a]pyridine-5-carboxylic acid (compound X-1) (0.228 g, 0.916 mmol, 1.10 equivalents), and N-ethyl-N-isopropyl-propan-2-amine (0.570 mL, 3.33 mmol, 4.00 equivalents) in ethyl acetate, 50% 1-propanephosphonic anhydride (0.546 mL, 0.916 mmol, 1.10 equivalents) was added. The reaction mixture was stirred at 85°C for 16 hours. The reaction mixture was diluted with ethyl acetate and quenched with water. The combined organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain 3-bromo-N-(cyanomethyl)-N-(4-fluoro-3-methoxyphenyl)pyrazolo[1,5-a]pyridine-5-carboxamide as a yellow, rubbery substance. LC-MS (Method C): Rt 0.94min, m / z=403(M+H) + 1H-NMR (400MHz, CDCl3, ppm) δ=3.85(s,3H),4.77(s,2H),6.73-6.90(m,3H),7.09(dd,J=10 .54,8.36Hz,1H),7.67(dd,J=1.82,1.09Hz,1H),7.96(s,1H),8.26(dd,J=7.27,1.09Hz,1H)

[0273] Step F: Preparation of methyl N-[5-[5-[cyanomethyl-(4-fluoro-3-methoxyphenyl)carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate (compound 3) A mixture of 3-bromo-N-(cyanomethyl)-N-(4-fluoro-3-methoxyphenyl)pyrazolo[1,5-a]pyridine-5-carboxamide (0.23 g, 0.57 mmol), methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (0.22 g, 0.80 mmol, 1.4 equivalents), and cesium carbonate (0.28 g, 0.86 mmol, 1.5 equivalents) in 2-methyltetrahydrofuran (3.4 mL) was flashed with argon for 5 minutes. Next, tetrakis(triphenylphosphine)palladium(0) (0.034 g, 0.029 mmol, 0.05 equivalents) was added, and the reaction mixture was heated at 100°C under microwave irradiation for 30 minutes. The reaction mixture was cooled to room temperature, and then water was added. The aqueous layer was extracted with ethyl acetate, the combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified in a silica gel cartridge (cyclohexane / ethyl acetate) to obtain methyl N-[5-[5-[cyanomethyl-(4-fluoro-3-methoxyphenyl)carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate as a yellow solid. LC-MS (Method C): Rt 0.87min, m / z=474(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=3.73-3.91(m,6H),4.68-4.82(m,2H),6.74-6.81(m,1H),6.81-6.86(m,1H),6.86-6.93(m,1H),7.0 4-7.16(m,1H),7.42-7.74(m,2H),7.78-7.83(m,1H),8.04-8.11(m,1H),8.11-8.16(m,1H),8.28-8.33(m,1H),8.33-8.38(m,1H)

[0274] Example 4: Preparation of methyl N-[5-[5-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate (compound 4) [ka] Step A: Preparation of 3-bromo-N-(4-fluoro-3-methoxyphenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide [ka] To a solution of 3-bromopyrazolo[1,5-a]pyridine-5-carboxylic acid (compound X-1) (0.702 g, 2.77 mmol), 4-fluoro-3-methoxy-N-methylaniline (0.599 mL, 4.15 mmol, 1.50 equivalents), and N-ethyl-N-isopropyl-propan-2-amine (2.37 mL, 13.8 mmol, 5.00 equivalents) in N,N-dimethylacetamide (17.6 mL), 50% 1-propanephosphonic anhydride in ethyl acetate (4.12 mL, 6.92 mmol, 2.50 equivalents) was added. The reaction mixture was stirred at 55°C for 35 minutes. The reaction mixture was diluted with ethyl acetate and quenched with a saturated solution of sodium carbonate. The combined organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate:ethanol, 3:1) to obtain 3-bromo-N-(4-fluoro-3-methoxyphenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide. LC-MS (Method C): Rt 0.83min, m / z=378 / 380(M+H) + 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=3.36-3.48(m,3H),3.70-3.81(m,3H),6.73-6.86(m,1H),7.02-7.14(m,1H),7.15 -7.23(m,1H),7.29-7.36(m,1H),7.46-7.55(m,1H),7.67-7.79(m,1H),8.17-8.35(m,1H)

[0275] Step B: Preparation of methyl N-[5-[5-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate (compound 4) A mixture of 3-bromo-N-(4-fluoro-3-methoxyphenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide (0.20 g, 0.53 mmol), 2-methoxycarbonylaminopyridine-5-boronic acid pinacol ester (0.216 g, 0.740 mmol, 1.40 equivalents), and cesium carbonate (0.26 g, 0.79 mmol, 1.5 equivalents) in 2-methyltetrahydrofuran (3.2 mL) was flushed with argon for 5 minutes. Next, tetrakis(triphenylphosphine)palladium(0) (0.032 g, 0.026 mmol, 0.050 eq.) was added, and the reaction mixture was heated at 100 °C under microwave irradiation 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 sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain methyl N-[5-[5-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]pyrazolo[1,5-a]pyridine-3-yl]-2-pyridyl]carbamate. LC-MS (Method C): Rt 0.87min, m / z=450(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=3.45-3.55(m,3H),3.75-3.83(m,3H),3.83-3.91(m,3H),6.60-6.72(m,1H),6.72-6.83(m,2H),6.96-7.06(m ,1H),7.62-7.71(m,1H),7.71-7.79(m,1H),8.03-8.10(m,1H),8.10- 8.14(m,1H),8.19-8.28(m,1H),8.28-8.35(m,1H),8.35-8.40(m,1H)

[0276] Example 5: Preparation of 3-(4-acetamidophenyl)-N-(4-chlorophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide (compound 6) [ka] Step A: Preparation of N-(4-chlorophenyl)pyrazolo[1,5-a]pyridine-5-carboxamide [ka] A solution of pyrazolo[1,5-a]pyridine-5-carboxylic acid (CAS104468-87-3) (2.00 g, 12.3 mmol), 4-chloroaniline (1.97 g, 14.8 mmol, 1.20 equivalents), and diisopropylamine (6.46 mL, 37.0 mmol, 3.00 equivalents) in dimethylformamide (37.0 mL) was divided and added to 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxidehexafluorophosphate (4.79 g, 12.3 mmol, 1.00 equivalent). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with an aqueous solution of sodium carbonate and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain N-(4-chlorophenyl)pyrazolo[1,5-a]pyridine-5-carboxamide as a white solid. LC-MS (Method C): Rt 0.91min, m / z=272 / 274(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=6.70-6.78(m,1H),7.16-7.23(m,1H),7.33-7.40(m,2H),7.5 8-7.65(m,2H),7.77-7.87(m,1H),8.04-8.10(m,1H),8.10-8.14(m,1H),8.52-8.60(m,1H)

[0277] Step B: Preparation of N-(4-chlorophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide [ka] To an ice-cold solution of N-(4-chlorophenyl)pyrazolo[1,5-a]pyridine-5-carboxamide (1.50 g, 5.52 mmol) in tetrahydrofuran (13.8 mL), sodium hydride (0.265 g, 6.07 mmol, 1.10 equivalents) was added in fractions. After 10 minutes at 0°C, iodomethane (0.526 mL, 8.28 mmol, 1.50 equivalents) was added dropwise. The reaction mixture was stirred at room temperature for 4 hours. Water was carefully added, and the reaction mixture was diluted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain N-(4-chlorophenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide as a yellow oily substance. LC-MS (Method C): Rt 0.88min, m / z=286 / 288(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=3.46-3.54(m,3H),6.50-6.55(m,1H),6.55-6.63(m,1H),7.0 1-7.12(m,2H),7.20-7.30(m,2H),7.51-7.65(m,1H),7.89-7.99(m,1H),8.20-8.29(m,1H).

[0278] Step C: Preparation of 3-bromo-N-(4-chlorophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide [ka] N-bromosuccinimide (0.706 g, 3.97 mmol, 1.03 equivalents) was added in fractions to a solution of N-(4-chlorophenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide (1.10 g, 3.85 mmol) in acetonitrile (19.3 mL). The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched with sodium sulfate solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain 3-bromo-N-(4-chlorophenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide as a solid. LC-MS (Method C): Rt 1.00min, m / z=364 / 366(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=3.42-3.54(m,3H),6.53-6.67(m,1H),7.03-7.12(m ,2H),7.27-7.32(m,2H),7.53-7.64(m,1H),7.84-7.96(m,1H),8.13-8.25(m,1H).

[0279] Step D: Preparation of 3-(4-aminophenyl)-N-(4-chlorophenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide [ka] Tetrakis(triphenylphosphine)palladium(0) (0) (0.305 g, 0.263 mmol) was added to a mixture of 3-bromo-N-(4-chlorophenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide (1.20 g, 3.29 mmol), 4-aminophenylboronate (0.685 g, 3.95 mmol, 1.20 equivalents), and sodium carbonate (1.05 g, 9.87 mmol, 3.00 equivalents) in 1,2-dimethoxyethane (26.3 mL) and water (6.58 mL). The reaction mixture was stirred at 85°C for 19 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain 3-(4-aminophenyl)-N-(4-chlorophenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide as a yellow solid. LC-MS (Method C): Rt 0.84min, m / z=377 / 379(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=3.47-3.55(m,3H),3.70-3.84(m,2H),6.67-6.81(m,3H),7.0 5-7.13(m,4H),7.30-7.37(m,2H),7.63-7.69(m,1H),7.97-8.05(m,1H),8.22-8.29(m,1H)

[0280] Step E: Preparation of 3-(4-acetamidophenyl)-N-(4-chlorophenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide (compound 6) A solution of 3-(4-aminophenyl)-N-(4-chlorophenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide (0.12 g, 0.32 mmol, 1.0 equivalent) and triethylamine (0.0673 mL, 0.478 mmol, 1.50 equivalents) in dichloromethane (2.5 mL) was added dropwise with acetyl chloride (0.026 mL, 0.35 mmol, 1.1 equivalents). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with dichloromethane and washed with a saturated solution of sodium carbonate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain 3-(4-acetamidophenyl)-N-(4-chlorophenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide. LC-MS (Method C): Rt 0.89min, m / z=419(M+H) + 1 H-NMR(400MHz,CDCl3,ppm)δ=2.20-2.31(m,3H),3.47-3.55(m,3H),6.72-6.80(m,1H),7.05-7.13(m,2H),7.16-7.23(m ,1H),7.26-7.27(m,2H),7.31-7.37(m,2H),7.52-7.61(m,2H),7.65-7.72(m,1H),8.03-8.11(m,1H),8.25-8.35(m,1H)

[0281] Example 6: Preparation of methyl N-[5-[5-[(2-methoxy-4-pyridyl)-methyl-carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate (compound 17) [ka] Step A: Preparation of 3-bromo-N-(2-methoxy-4-pyridyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide [ka] POCl3 (0.088 mL, 0.96 mmol, 3.0 equivalents) was added to a solution of 3-bromopyrazolo[1,5-a]pyridine-5-carboxylic acid (compound X-1) (77.1 mg, 0.320 mmol) and 2-methoxy-N-methylpyridine-4-amine (52.5 mg, 0.380 mmol, 1.19 equivalents) in pyridine (1.00 mL) cooled to 10°C. The reaction mixture was stirred at 10°C for 2 hours. The reaction was quenched with water, and the mixture was concentrated under reduced pressure. The residue was dissolved in dimethylacetamide and filtered through silica gel. The crude residue was used in the next step without purification.

[0282] Step B: Preparation of methyl N-[5-[5-[(2-methoxy-4-pyridyl)-methyl-carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate (compound 17) A solution of Na2CO3 (12.85 mg, 0.1200 mmol, 3.00 equivalents) in water (0.20 mL) was degassed and added to a solution of methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (14.5 mg, 0.0521 mmol, 1.30 equivalents), 3-bromo-N-(2-methoxy-4-pyridyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide (14.4 mg, 0.0401 mmol), and XPhos Pd G2 (3.31 mg, 0.00421 mmol, 0.010 equivalents) in acetonitrile (0.30 mL) that had been degassed inside a glove box. The reaction mixture was then stirred at 100°C for 16 hours. The solvent was then removed. The residue was absorbed in dimethylacetamide / methanol (1:1, 0.800 mL), filtered over silica gel, and then purified by reverse-phase chromatography (eluting with water / acetonitrile containing 0.1% formic acid) to obtain methyl N-[5-[5-[(2-methoxy-4-pyridyl)-methyl-carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-2-pyridyl]carbamate. LC-MS (Method B): Rt 1.16min, m / z=433(M+H) +

[0283] Example 7: Preparation of 3-[6-(ethylcarbamoylamino)-3-pyridyl]-N-(3-fluorophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide (compound 26) [ka] Step A: Preparation of 3-bromo-N-(3-fluorophenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide [ka] To a solution of 3-bromopyrazolo[1,5-a]pyridine-5-carboxylic acid (compound X-1) (77.1 mg, 0.320 mmol) and 3-fluoro-N-methylaniline (48.6 mg, 0.389 mmol, 1.22 equivalents) in pyridine (1.00 mL) cooled to 10°C, POCl3 (0.088 mL, 0.96 mmol, 3.0 equivalents) was added. The reaction mixture was stirred at 10°C for 2 hours. The reaction was quenched with water, and the mixture was concentrated under reduced pressure. The residue was dissolved in dimethylacetamide and filtered over silica gel. The crude residue was used in the next step without purification.

[0284] Step B: Preparation of 3-[6-(ethylcarbamoylamino)-3-pyridyl]-N-(3-fluorophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide (compound 26) A solution of Na2CO3 (12.85 mg, 0.1200 mmol, 3.00 equivalents) in water (0.20 mL) was degassed and added to a solution of 3-ethyl-1-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-yl]urea (15.0 mg, 0.051 mmol, 1.28 equivalents), 3-bromo-N-(3-fluorophenyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide (13.9 mg, 0.0401 mmol), and XPhos Pd G2 (3.31 mg, 0.00421 mmol, 0.010 equivalents) in acetonitrile (0.30 mL) that had been degassed inside a glove box. The reaction mixture was then stirred at 100°C for 16 hours. The solvent was then removed. The residue was absorbed in dimethylacetamide / methanol (1:1, 0.800 mL), filtered over silica gel, and then purified by reverse-phase chromatography (eluting with water / acetonitrile containing 0.1% formic acid) to obtain 3-[6-(ethylcarbamoylamino)-3-pyridyl]-N-(3-fluorophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide. LC-MS (Method B): Rt 1.25min, m / z=433(M+H) +

[0285] Example 8: Preparation of 3-(6-acetamido-3-pyridyl)-N-(4-cyano-3-methoxyphenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide (compound 41) [ka] Step A: Preparation of 3-bromo-N-(4-cyano-3-methoxyphenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide [ka] POCl3 (0.088 mL, 0.96 mmol, 3.0 equivalents) was added to a solution of 3-bromopyrazolo[1,5-a]pyridine-5-carboxylic acid (compound X-1) (77.1 mg, 0.320 mmol) and 2-methoxy-4-(methylamino)benzonitrile (58.1 mg, 0.358 mmol, 1.12 equivalents) in pyridine (1.00 mL) cooled to 10°C. The reaction mixture was stirred at 10°C for 2 hours. The reaction was quenched with water, and the mixture was concentrated under reduced pressure. The residue was dissolved in dimethylacetamide and filtered over silica gel. The crude residue was used in the next step without purification.

[0286] Step B: Preparation of 3-(6-acetamido-3-pyridyl)-N-(4-cyano-3-methoxyphenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide (compound 41) A solution of Na2CO3 (12.85 mg, 0.1200 mmol, 3.00 equivalents) in water (0.20 mL) was degassed and added to a solution of 2-acetamidopyridine-5-boronic acid pinacol ester (13.6 mg, 0.052 mmol, 1.30 equivalents), 3-bromo-N-(4-cyano-3-methoxyphenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide (15.4 mg, 0.0401 mmol), and XPhos Pd G2 (3.31 mg, 0.00421 mmol, 0.010 equivalents) in acetonitrile (0.30 mL) that had been degassed inside a glove box. The reaction mixture was then stirred at 100°C for 16 hours. The solvent was then removed. The residue was absorbed in dimethylacetamide / methanol (1:1, 0.800 mL), filtered over silica gel, and then purified by reverse-phase chromatography (eluting with water / acetonitrile containing 0.1% formic acid) to obtain 3-(6-acetamido-3-pyridyl)-N-(4-cyano-3-methoxyphenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide. LC-MS (Method B): Rt 1.16min, m / z=441(M+H) +

[0287] Example 9: Preparation of N-(4-cyano-3-methyl-phenyl)-3-[4-[(2-methoxyacetyl)amino]phenyl]-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide (compound 45) [ka] Step A: Preparation of 3-bromo-N-(4-cyano-3-methylphenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide [ka] POCl3 (0.088 mL, 0.96 mmol, 3.0 equivalents) was added to a solution of 3-bromopyrazolo[1,5-a]pyridine-5-carboxylic acid (compound X-1) (77.1 mg, 0.320 mmol) and 2-methyl-4-(methylamino)benzonitrile (52.3 mg, 0.358 mmol, 1.12 equivalents) in pyridine (1.00 mL) cooled to 10°C. The reaction mixture was stirred at 10°C for 2 hours. The reaction was quenched with water, and the mixture was concentrated under reduced pressure. The residue was dissolved in dimethylacetamide and filtered over silica gel. The crude residue was used in the next step without purification.

[0288] Step B: Preparation of N-(4-cyano-3-methyl-phenyl)-3-[4-[(2-methoxyacetyl)amino]phenyl]-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide (compound 45) A solution of Na2CO3 (12.85 mg, 0.1200 mmol, 3.00 equivalents) in water (0.20 mL) was degassed and added to a solution of 2-methoxy-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamide (15.6 mg, 0.054 mmol, 1.33 equivalents), 3-bromo-N-(2-methoxy-4-pyridyl)-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide (14.8 mg, 0.0401 mmol), and XPhos Pd G2 (3.31 mg, 0.00421 mmol, 0.010 equivalents) in acetonitrile (0.30 mL) that had been degassed inside a glove box. The reaction mixture was then stirred at 100°C for 16 hours. The solvent was then removed. The residue was absorbed in dimethylacetamide / methanol (1:1, 0.800 mL), filtered over silica gel, and then purified by reverse-phase chromatography (eluting with water / acetonitrile containing 0.1% formic acid) to obtain N-(4-cyano-3-methyl-phenyl)-3-[4-[(2-methoxyacetyl)amino]phenyl]-N-methyl-pyrazolo[1,5-a]pyridine-5-carboxamide. LC-MS (Method B): Rt 1.29min, m / z=454(M+H) +

[0289] Biological examples: The fungicidal activity of the compound of the present invention was tested as follows.

[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 percentage compared to untreated leaf fragments when an appropriate level of disease appears on untreated test leaf fragments (5-7 days after application).

[0291] The following compounds, at 200 ppm, resulted in at least 80% control of Phytophthora infestans, which exhibited widespread disease development, compared to untreated controls under identical conditions: 1, 2, 3, 4.

[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 formulated 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, and the activity of the compound is evaluated as the disease control rate compared to untreated leaflets when an appropriate level of disease appears on untreated check leaflets (6-8 days after application).

[0293] The following compounds, at 200 ppm, resulted in at least 80% control of Plasmopara viticola, which exhibited widespread disease development, compared to untreated controls under the same conditions: 1, 3, 4.

[0294] Pythium ultimum / Liquid culture (Seedling blight) Mycelial fragments and oospores from a newly grown liquid culture of fungi 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, resulted in at least 80% control of Pythium ultimum, compared to an untreated control under the same conditions, exhibiting widespread disease development: 1, 2, 4, 5, 6.

Claims

1. Equation (I) 【Chemistry 1】 (In the formula, Z is O or S, preferably Z is O) A 1 is CH or N, preferably N. R 1a , R 1b and R 1c are independently selected from hydrogen, hydroxy, halogen, CN, C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 alkoxy-C 1-6 alkyl, C 3-6 cycloalkyl-C 1-4 alkyl, C 1-6 alkylsulfanyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 alkoxy, amino and NHC(O)C 1-6 alkyl, and are independently selected from A 2 CR is independent 2 or N, provided there are three or fewer A's. 2 is N, preferably two or fewer A 2 is N, preferably one or less A 2 is N, and more preferably the four A 2 CR 2 The condition is that, R 2 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Independently selected from alkylcarbonyls, the C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Each alkylcarbonyl group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs. A 3 CR is independent 3 or N, R 3 is selected from 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 each 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 selected from alkyl and CN, and said C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 alkoxy, C 1-6 alkylsulfanyl-C 1-6 alkyl, C 1-6 alkylsulfinyl-C 1-6 alkyl, C 1-6 alkylsulfonyl-C 1-6 alkyl, C 1-6 alkoxycarbonyl-C 1-6 alkyl, C 1-6 alkylaminocarbonyl-C 1-6 alkyl and di-C 1-6 alkylaminocarbonyl-C 1-6 each of the alkyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen and CN, A 3 and R 4 Together, they arbitrarily form a ring, preferably a 5-8 membered heterocycle, more preferably a 6-membered heterocycle, and R 5 C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, diC 1-6 Alkylamino and C 1-6 Alkyl C 1-6 Selected from alkoxyaminos, each of the groups may be optionally substituted with one to three substituents independently selected from halogens and CNs. A compound or a salt or N-oxide thereof, wherein the compound of formula (I) is used as a fungicide.

2. Equation (I) 【Chemistry 2】 (In the formula, Z is O or S, preferably Z is O) A 1 is CH or N, preferably N. R 1a , R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 Selected independently of 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 the four A 2 CR 2 The condition is that, R 2 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Independently selected from alkylcarbonyls, the C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Each alkylcarbonyl group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs, provided that at least two R groups are present. 2 This is conditional on it not being 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 Together, they arbitrarily form a ring, preferably a 5-8 membered heterocycle, more preferably a 6-membered heterocycle, and R 5 C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, diC 1-6 Alkylamino and C 1-6 Alkyl C 1-6 Selected from alkoxyaminos, each of the groups may be optionally substituted with one to three substituents independently selected from halogens and CNs. A compound of the same, or its salt or N-oxide.

3. R 1a , R 1b and R 1c is hydrogen, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 A compound according to claim 1 or 2, independently selected from alkoxys.

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

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

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

9. The four A's 2 CR 2 and A 3 CR 3 The compound according to any one of claims 1 to 5. 【Request Item 10】 【Chemistry 7】 teeth, 【Transformation 8】 The compound according to claim 9.

11. R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl and C 1-6 Selected from alkoxy, the C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl and C 1-6 The compound according to any one of claims 1 to 10, wherein each alkoxy group may be optionally substituted with one to three substituents independently selected from halogens and CNs.

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

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

14. The composition according to claim 13, further comprising at least one compound selected from additional active ingredients, suitable formulation inactive ingredients, carriers, auxiliaries, and any mixture thereof.

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

16. Formula (XI) 【Chemistry 9】 (In the formula, Z is O or S, preferably Z is O) R 1a , R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 Independently selected from alkyl groups, preferably R 1a , R 1b and R 1c It 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 the four A 2 CR 2 The condition is that, R 2 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl and C 1-6 Independently selected from alkylcarbonyls, the C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, 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 substituent independently selected from halogen, hydroxyl, and CN, provided that at least two R groups are present. 2 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 3-6 Cycloalkyl, 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 3-6 Cycloalkyl, 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 substituent independently selected from halogen, hydroxyl, and CN, preferably R 3 It 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, 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 combine to form a ring, preferably a 5-8 membered heterocycle, more preferably a 6-membered heterocycle. A compound of the same, or its salt or N-oxide.

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