Imidazone bicyclic derivatives

Abstract

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

Description

Technical Field

[0001] The present invention relates to a microbicidal activity, particularly a fungicidal activity, more specifically an activity against oomycetes, for example, a microbicidal imidazo bicyclic derivative as an active ingredient. The present invention relates to the preparation of these imidazo bicyclic derivatives, intermediates useful for the preparation of these imidazo bicyclic derivatives, the preparation of these intermediates, pesticidal compositions containing at least one of the imidazo bicyclic derivatives, the preparation of these compositions and the use of imidazo bicyclic derivatives or compositions in agriculture or horticulture for controlling, preventing or preventing ectoparasitism of plants, harvested food crops, seeds or abiotic materials by phytopathogenic microorganisms, particularly fungi, more specifically oomycetes.

Summary of the Invention

Problems to be Solved by the Invention

[0002] Here, surprisingly, it has been found that certain novel imidazo bicyclic derivatives have particularly advantageous fungicidal properties against oomycetes.

Means for Solving the Problems

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

Chemical Formula

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

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

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

[0007] In a fourth aspect, the present invention provides a method for eradicating, preventing or controlling 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 susceptible to damage by the plant pathogen, or plant reproductive material. According to this fourth aspect of the present invention, the method may be limited to methods for treating the body of a human or animal by surgery or treatment.

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

[0009] In a sixth aspect, the present invention provides a method for eradicating, preventing, or controlling plant pathogenic diseases such as plant pathogenic fungi, comprising applying a compound of formula (I) described herein or a composition containing a compound of formula (I) to the plant pathogenic fungi or the habitat of the plant pathogenic fungi (particularly plants susceptible to damage from plant pathogenic fungi, particularly oomycetes) or plant propagation material. According to this sixth aspect of the present invention, the method may be limited to methods for treating the body of a human or animal by surgery or treatment.

[0010] When it is indicated that one group, for example, an alkyl group, is substituted, this includes those groups that are part of the other groups, for example, the alkyl group in alkylthio.

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

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

[0013] - In this specification, the term "alkyl" used 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. A alkyl group having 1 to 4 carbon atoms is preferred, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl.

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

[0015] - The term "alkynyl," either alone or as part of a chemical group, preferably refers to a linear or branched hydrocarbon having 2 to 6 carbon atoms and at least one triple bond, such as 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, and 3-hexynyl This represents 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, and 2,5-hexadinyl. Alkynnyls having 2 to 4 carbon atoms are preferred, for example, ethynnyl, 2-propynyl, or 2-butynyl-2-propenyl.

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

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

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

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

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

[0021] - The term "alkoxy" is derived from the formula -OR a It refers to the base of, and in the formula, R a 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 (as described above) substituted with the aforementioned alkoxy group. Examples include methoxymethyl, methoxyethyl, ethoxymethyl, and propoxymethyl.

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

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

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

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

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

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

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

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

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

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

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

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

[0034] The effective dose can be readily determined by those skilled in the art by observing the results obtained using known techniques and under similar circumstances. Several factors are considered in determining the effective dose, including, but not limited to, the type of plant or derivative product to which it is applied, the pathogen being controlled and its life cycle, the specific compound to which it is applied, the type of application, and other relevant circumstances. [Modes for carrying out the invention]

[0035] Compounds of formula (I) having at least one basic center can form acid addition salts, for example, with strong inorganic acids, such as mineral acids, such as perchloric acid, sulfuric acid, nitric acid, nitrite, phosphoric acid, or hydrohalic acid; with strong organic carboxylic acids, such as unsubstituted or halogenated C1-C4 alkane carboxylic acids, such as acetic acid; with saturated or unsaturated dicarboxylic acids, such as oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, or phthalic acid; with hydroxycarboxylic acids, such as ascorbic acid, lactic acid, malic acid, tartaric acid, or citric acid; or with organic sulfonic acids, such as unsubstituted or halogenated C1-C4 alkanes or aryl sulfonic acids, such as methane or p-toluenesulfonic acid. Compounds of formula (I) having at least one acidic group can form salts with bases, such as mineral salts, such as alkali metal or alkaline earth metal salts, such as sodium, potassium or magnesium salts, or salts with ammonia or organic amines, such as morpholine, piperidine, pyrrolidine, mono, di or tri lower alkylamines, such as ethyl, diethyl, triethyl or dimethylpropylamine, or mono, di or trihydroxy lower alkylamines, such as mono, di or triethanolamine.

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

[0037] The compound of formula (I) according to the present invention also includes a hydrate that may be formed during salt formation.

[0038] In further embodiments, the compound of formula (I) according to the present invention is R 1 However, hydrogen, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected independently of alkoxy, more preferably R 1 However, hydrogen and C 1-6 Compounds are provided that are independently selected from alkyl groups.

[0039] In further embodiments, the compound of formula (I) according to the present invention is R 2 However, hydrogen, hydroxyl, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, and C 1-6 Independently selected from alkylcarbonyls, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, and C 1-6 The alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxyl, and CN; preferably R 2 However, hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6Alkyl, C 1-6 Alkoxycarbonyl and C 1-6 Alkoxy-C 1-6 Selected independently of alkoxy, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl and C 1-6 Alkoxy-C 1-6 Each of the alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; more preferably, R 2 However, hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, and C 1-6 Alkoxy-C 1-6 Compounds are provided that are independently selected from alkyl groups.

[0040] In further embodiments, the compound of formula (I) according to the present invention is R 3 However, 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 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, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, amino, C 1-6 Alkylamino, diC1-6 -Alkylamino and C 3-6 Each of the cycloalkylamino groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; preferably, R 3 A compound is provided in which hydrogen is present.

[0041] 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 is N.

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

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

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

[0045] [ka] but [ka] In a particular embodiment, R 2 This is as defined in the present invention; 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, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 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; more 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, where C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl and C 1-6 Alkoxy-C 1-6 Each of the alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxyl, and CN; more preferably, R 2 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, and C 1-6 Alkoxy-C 1-6 It is selected independently of alkyl.

[0046] In further embodiments, the compound of formula (I) according to the present invention is R 4 However, C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl and C 1-6 Selected from alkoxy, where C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl and C1-6 Each of the alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN; preferably R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy, where C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Each alkoxy group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN; Here, A 3 and R 4 Compounds are provided which, optionally together, form a ring, preferably a 5-8 membered heterocycle, more preferably a 6 membered heterocycle.

[0047] In a further embodiment, the compound of formula (I) according to the present invention is A 3 CR 3 And R 3 and R 4 Together, they form a ring, preferably a 5-8 membered heterocycle, preferably a 6 membered heterocycle, more preferably the ring W1, W2, or W3 described in the compound of formula (I): [ka] A compound is provided that forms one of the following.

[0048] The carbon and / or nitrogen atoms forming the ring (W1, W2, or W3) are, in particular, R 3’ It can be substituted with the base, where R 3’ is hydrogen, C 1-6 Alkyl and C 3-6 Selected from cycloalkyl, C1-6 Alkyl and C 3-6 Each cycloalkyl group may be optionally substituted with one to three substituents independently selected from halogens and CN. For example, the compounds of formula (I-W3) may be as follows: [ka]

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

[0050] The carbon and / or nitrogen atoms forming the ring (W1, W2, or W3) are, in particular, R 3’ It can be substituted with the base, where 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 one to three substituents independently selected from halogens and CN. For example, the compounds of formula (I-W3) may be as follows: [ka]

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

[0052] In certain embodiments, a compound of formula (I) according to the present invention is provided, wherein, Z is O; One A 1 is N, and one A 1 CR 1 and; R 1 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 alkoxy, more preferably, R 1 is hydrogen and C 1-6 Selected independently of alkyl; The four A's 2 CR 2 And here, 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 and C 1-6 Independently selected from alkylsulfonyls, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl and C 1-6 Each alkylsulfonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; preferably, R 2 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Selected independently of alkoxy, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Each of the alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; more preferably, R 2 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl and C 1-6 Alkoxy-C 1-6 Selected independently of alkoxy, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl and C 1-6 Alkoxy-C 1-6 Each alkoxy group may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; A 3 CR 3 And here, R 3 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C1-6 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 independently from cycloalkylaminos, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, amino, C 1-6 Alkylamino, diC 1-6 -Alkylamino and C 3-6 Each of the cycloalkylamino groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; preferably R 3 is hydrogen; A 4 is CH or N, preferably N; 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, where C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Each alkoxy group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN; A 3 and R 4 They may optionally come together to form a ring, preferably a 5- to 8-membered heterocycle, more preferably a 6-membered heterocycle; 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, where each of the groups may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN, preferably R 5 C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl and C 1-6 Alkoxy C 1-6 Selected from alkyl groups, each of which may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN.

[0053] In a preferred embodiment, [ka] but [ka] And in the formula, R 2 This is as defined in the present invention; 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, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, 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 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl and C 1-6 Alkoxy-C 1-6 Selected independently of alkoxy, where C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C1-6 Alkoxycarbonyl and C 1-6 Alkoxy-C 1-6 Each of the alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxyl, and CN; more preferably, R 2 Hydrogen, halogen, CN, C 1-6 Alkyl and C 1-6 It is selected independently of alkoxy.

[0054] In further embodiments, the compound according to the present invention is Methyl N-[5-[6-[(4-fluoro-3-methylphenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-b]pyridazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-(6-fluoro-3,4-dihydro-2H-quinoline-1-carbonyl)-8-methylimidazo[1,2-b]pyridazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-fluorophenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-b]pyridazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-b]pyridazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-(6-fluoro-3,4-dihydro-2H-quinoline-1-carbonyl)imidazo[1,2-b]pyridazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-b]pyridazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-fluoro-3-methylphenyl)-methyl-carbamoyl]imidazo[1,2-b]pyridazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-b]pyridazine-3-yl]-2-pyridyl]carbamate; 3-(4-acetamidophenyl)-N-(4-chlorophenyl)-N-methylimidazo[1,2-a]pyrimidine-6-carboxamide; and 3-(4-acetamidophenyl)-N-(4-chlorophenyl)-N-methyl-imidazo[1,2-b]pyrimidine-6-carboxamide Selected from.

[0055] The methods according to the present invention have advantageous properties for protecting plants from pathogenic attacks or ectoparasites that cause disease and damage to plants, such as plant pathogenic fungi, particularly oomycetes, and in the case of plants in particular, the present invention can control, limit or prevent pathogenic damage to plants, parts of plants, plant propagation materials and / or grown plants.

[0056] The compounds listed in Tables 1.1 to 1.100 and 2.1 to 2.50 below exemplify specific compounds of the present invention.

[0057] Table 1.1 lists compounds E1.1 to E1.952 of formula (Ia). [ka] Provided, in the formula, R 2 H is R 5 It is CH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined in [reference].

[0058] More specifically, see Table Z 1 R 3 and R 4 This also includes compounds in which R forms a ring together. In this case, the ring is R 3 and R 4 Column (Table Z)1 ) shown in R 3 and R 4 The amide atoms are bonded together along the amide atom attached to the bicyclic core of formula (Ia). For example, R in compound E1.103 3 and R 4 Please refer to the column.

[0059] [Table 1-1]

[0060] [Table 1-2]

[0061] [Table 1-3]

[0062] [Table 1-4]

[0063] [Table 1-5]

[0064] [Table 1-6]

[0065] [Table 1-7]

[0066] [Table 1-8]

[0067] [Table 1-9]

[0068] Table 1-10

[0069] Table 1-11

[0070] Table 1-12

[0071] Table 1-13

[0072] Table 1-14

[0073] Table 1-15

[0074] Table 1-16

[0075] Table 1-17

[0076] Table 1-18

[0077] Table 1-19

[0078] Table 1-20

[0079] Table 1-21

[0080] Table 1-22

[0081] Table 1-23

[0082] Table 1-24

[0083] Table 1-25

[0084] Table 1-26

[0085] Table 1-27

[0086] Table 1-28

[0087] Table 1-29

[0088] Table 1-30

[0089] Table 1-31

[0090] Table 1-32

[0091] Table 1-33

[0092] Table 1-34

[0093] Table 1-35

[0094] Table 1-36

[0095] Table 1-37

[0096] Table 1-38

[0097] Table 1-39

[0098] Table 1-40

[0099] Table 1-41

[0100] Table 1-42

[0101] Table 1-43

[0102] Table 1-44

[0103] Table 1-45

[0104] Table 1-46

[0105] Table 1-47

[0106] Table 1-48

[0107] Table 1-49

[0108] Table 1-50

[0109] Table 1-51

[0110] Table 1-52

[0111] Table 1-53

[0112] Table 1-54

[0113] Table 1-55

[0114] Table 1-56

[0115] Table 1-57

[0116] Table 1-58

[0117] Table 1-59

[0118] Table 1-60

[0119] [Table 1-61]

[0120] [Table 1-62]

[0121] [Table 1-63]

[0122] Table 1.2 provides compounds E2.1 to E2.952 of formula (Ia), where R 2 H is R 5 It is CH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined in [reference].

[0123] Table E1.3 provides compounds E3.1 to E3.952 of formula (Ia), where R 2 H is R 5 It is OCH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined in [reference].

[0124] Table 1.4 provides compounds E4.1 to E4.952 of formula (Ia), where R 2 H is R 5 It is OCH3, and A 4 is N, and R 1a , R 3 , R 4 , A2a , A 2b Table Z 1 As defined in [reference].

[0125] Table 1.5 provides compounds E5.1 to E5.952 of formula (Ia), where R 2 H is R 5 It is cyclopropyl, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0126] Table 1.6 provides compounds E6.1 to E6.952 of formula (Ia), where R 2 H is R 5 It is cyclopropyl, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined in [reference].

[0127] Table 1.7 provides compounds E7.1 to E7.952 of formula (Ia), where R 2 H is R 5 It is CH2OCH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0128] Table 1.8 provides compounds E8.1 to E8.952 of formula (Ia), where R 2 H is R 5 It is CH2OCH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2bTable Z 1 As defined in [reference].

[0129] Table 1.9 provides compounds E9.1 to E9.952 of formula (Ia), where R 2 H is R 5 It is NHCH2CH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0130] Table 1.10 provides compounds E10.1 to E10.952 of formula (Ia), where R 2 H is R 5 It is NHCH2CH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined in [reference].

[0131] Table 1.11 provides compounds E11.1 to E11.952 of formula (Ia), where R 2 It is CH3, and R 5 It is CH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0132] Table 1.12 provides compounds E12.1 to E12.952 of formula (Ia), where R 2 It is CH3, and R 5 It is CH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1As defined below.

[0133] Table 1.13 provides compounds E13.1 to E13.952 of formula (Ia), where R 2 It is CH3, and R 5 It is OCH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0134] Table 1.14 provides compounds E14.1 to E14.952 of formula (Ia), where R 2 It is CH3, and R 5 It is OCH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0135] Table 1.15 provides compounds E15.1 to E15.952 of formula (Ia), where R 2 It is CH3, and R 5 It is cyclopropyl, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0136] Table 1.16 provides compounds E16.1 to E16.952 of formula (Ia), where R 2 It is CH3, and R 5 It is cyclopropyl, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0137] Table 1.17 provides compounds E17.1 to E17.952 of formula (Ia), where R 2 It is CH3, and R 5 It is CH2OCH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0138] Table 1.18 provides compounds E18.1 to E18.952 of formula (Ia), where R 2 It is CH3, and R 5 It is CH2OCH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0139] Table 1.19 provides compounds E19.1 to E19.952 of formula (Ia), where R 2 It is CH3, and R 5 It is NHCH2CH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0140] Table 1.20 provides compounds E20.1 to E20.952 of formula (Ia), where R 2 It is CH3, and R 5 It is NHCH2CH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0141] Table 1.21 provides compounds E21.1 to E21.952 of formula (Ia), where R 2 It is CH2CH3, and R 5 It is CH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0142] Table 1.22 provides compounds E22.1 to E22.952 of formula (Ia), where R 2 It is CH2CH3, and R 5 It is CH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0143] Table 1.23 provides compounds E23.1 to E23.952 of formula (Ia), where R 2 It is CH2CH3, and R 5 It is OCH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0144] Table 1.24 provides compounds E24.1 to E24.952 of formula (Ia), where R 2 It is CH2CH3, and R 5 It is OCH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0145] Table 1.25 provides compounds E25.1 to E25.952 of formula (Ia), where R 2 It is CH2CH3, and R 5 It is cyclopropyl, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined in [reference].

[0146] Table 1.26 provides compounds E26.1 to E26.952 of formula (Ia), where R 2 It is CH2CH3, and R 5 It is cyclopropyl, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0147] Table 1.27 provides compounds E27.1 to E27.952 of formula (Ia), where R 2 It is CH2CH3, and R 5 It is CH2OCH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0148] Table 1.28 provides compounds E28.1 to E28.952 of formula (Ia), where R 2 It is CH2CH3, and R 5 It is CH2OCH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0149] Table 1.29 provides compounds E29.1 to E29.952 of formula (Ia), where R 2 It is CH2CH3, and R 5 It is NHCH2CH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0150] Table 1.30 provides compounds E30.1 to E30.952 of formula (Ia), where R 2 It is CH2CH3, and R 5 It is NHCH2CH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0151] Table 1.31 provides compounds E31.1 to E31.952 of formula (Ia), where R 2 F is R 5 It is CH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0152] Table 1.32 provides compounds E32.1 to E32.952 of formula (Ia), where R 2 F is R 5 It is CH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0153] Table 1.33 provides compounds E33.1 to E33.952 of formula (Ia), wherein R 2 is F, R 5 is OCH3, A 4 is CH, R 1a , R 3 , R 4 , A 2a , A 2b are as defined in Table Z 1 as defined.

[0154] Table 1.34 provides compounds E34.1 to E34.952 of formula (Ia), wherein R 2 is F, R 5 is OCH3, A 4 is N, R 1a , R 3 , R 4 , A 2a , A 2b are as defined in Table Z 1 as defined.

[0155] Table 1.35 provides compounds E35.1 to E35.952 of formula (Ia), wherein R 2 is F, R 5 is cyclopropyl, A 4 is CH, R 1a , R 3 , R 4 , A 2a , A 2b are as defined in Table Z 1 as defined.

[0156] Table 1.36 provides compounds E36.1 to E36.952 of formula (Ia), wherein R 2 is F, R 5 is cyclopropyl, A 4 is N, R 1a , R 3 , R 4 , A 2a , A 2b are as defined in Table Z 1 as defined.

[0157] Table 1.37 provides compounds E37.1 to E37.952 of formula (Ia), where R 2 F is R 5 It is CH2OCH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0158] Table 1.38 provides compounds E38.1 to E38.952 of formula (Ia), where R 2 F is R 5 It is CH2OCH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0159] Table 1.39 provides compounds E39.1 to E39.952 of formula (Ia), where R 2 F is R 5 It is NHCH2CH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0160] Table 1.40 provides compounds E40.1 to E40.952 of formula (Ia), where R 2 F is R 5 It is NHCH2CH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0161] Table 1.41 provides compounds E41.1 to E41.952 of formula (Ia), wherein R 2 is Cl, R 5 is CH3, A 4 is CH, R 1a , R 3 , R 4 , A 2a , A 2b are as defined in Table Z 1 .

[0162] Table 1.42 provides compounds E42.1 to E42.952 of formula (Ia), wherein R 2 is Cl, R 5 is CH3, A 4 is N, R 1a , R 3 , R 4 , A 2a , A 2b are as defined in Table Z 1 .

[0163] Table 1.43 provides compounds E43.1 to E43.952 of formula (Ia), wherein R 2 is Cl, R 5 is OCH3, A 4 is CH, R 1a , R 3 , R 4 , A 2a , A 2b are as defined in Table Z 1 .

[0164] Table 1.44 provides compounds E44.1 to E44.952 of formula (Ia), wherein R 2 is Cl, R 5 is OCH3, A 4 is N, R 1a , R 3 , R 4 , A 2a , A 2b are as defined in Table Z 1 .

[0165] Table 1.45 provides compounds E45.1 to E45.952 of formula (Ia), where R 2 is Cl, and R 5 It is cyclopropyl, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0166] Table 1.46 provides compounds E46.1 to E46.952 of formula (Ia), where R 2 is Cl, and R 5 It is cyclopropyl, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0167] Table 1.47 provides compounds E47.1 to E47.952 of formula (Ia), where R 2 is Cl, and R 5 It is CH2OCH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0168] Table 1.48 provides compounds E48.1 to E48.952 of formula (Ia), where R 2 is Cl, and R 5 It is CH2OCH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0169] Table 1.49 provides compounds E49.1 to E49.952 of formula (Ia), where R 2 is Cl, and R 5 It is NHCH2CH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0170] Table 1.50 provides compounds E50.1 to E50.952 of formula (Ia), where R 2 is Cl, and R 5 It is NHCH2CH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0171] Table 1.51 provides compounds E51.1 to E51.952 of formula (Ia), where R 2 is Br, R 5 It is CH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0172] Table 1.52 provides compounds E52.1 to E52.952 of formula (Ia), where R 2 is Br, R 5 It is CH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0173] Table 1.53 provides compounds E53.1 to E53.952 of formula (Ia), where R 2 is Br, R 5 It is OCH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0174] Table 1.54 provides compounds E54.1 to E54.952 of formula (Ia), where R 2 is Br, R 5 It is OCH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0175] Table 1.55 provides compounds E55.1 to E55.952 of formula (Ia), where R 2 is Br, R 5 It is cyclopropyl, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0176] Table 1.56 provides compounds E56.1 to E56.952 of formula (Ia), where R 2 is Br, R 5 It is cyclopropyl, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0177] Table 1.57 provides compounds E57.1 to E57.952 of formula (Ia), where R 2 is Br, R 5 It is CH2OCH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0178] Table 1.58 provides compounds E58.1 to E58.952 of formula (Ia), where R 2 is Br, R 5 It is CH2OCH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0179] Table 1.59 provides compounds E59.1 to E59.952 of formula (Ia), where R 2 is Br, R 5 It is NHCH2CH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0180] Table 1.60 provides compounds E60.1 to E60.952 of formula (Ia), where R 2 is Br, R 5 It is NHCH2CH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0181] Table 1.61 provides compounds E61.1 to E61.952 of formula (Ia), where R 2 is CN, R 5 It is CH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0182] Table 1.62 provides compounds E62.1 to E62.952 of formula (Ia), where R 2 is CN, R 5 It is CH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0183] Table 1.63 provides compounds E63.1 to E63.952 of formula (Ia), where R 2 is CN, R 5 It is OCH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0184] Table 1.64 provides compounds E64.1 to E64.952 of formula (Ia), where R 2 is CN, R 5 It is OCH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0185] Table 1.65 provides compounds E65.1 to E65.952 of formula (Ia), where R 2 is CN, R 5 It is cyclopropyl, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0186] Table 1.66 provides compounds E66.1 to E66.952 of formula (Ia), where R 2 is CN, R 5 It is cyclopropyl, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0187] Table 1.67 provides compounds E67.1 to E67.952 of formula (Ia), where R 2 is CN, R 5 It is CH2OCH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0188] Table 1.68 provides compounds E68.1 to E68.952 of formula (Ia), where R 2 is CN, R 5 It is CH2OCH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0189] Table 1.69 provides compounds E69.1 to E69.952 of formula (Ia), where R 2 is CN, R 5 It is NHCH2CH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0190] Table 1.70 provides compounds E70.1 to E70.952 of formula (Ia), where R 2 is CN, R 5 It is NHCH2CH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0191] Table 1.71 provides compounds E71.1 to E71.952 of formula (Ia), where R 2 It is OCH3, and R 5 CH3, A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0192] Table 1.72 provides compounds E72.1 to E72.952 of formula (Ia), where R 2 It is OCH3, and R 5 It is CH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0193] Table 1.73 provides compounds E73.1 to E73.952 of formula (Ia), where R 2 It is OCH3, and R 5 It is OCH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0194] Table 1.74 provides compounds E74.1 to E74.952 of formula (Ia), where R 2 It is OCH3, and R 5 It is OCH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0195] Table 1.75 provides compounds E75.1 to E75.952 of formula (Ia), where R 2 It is OCH3, and R 5 is cyclopropyl, A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0196] Table 1.76 provides compounds E76.1 to E76.952 of formula (Ia), where R 2 It is OCH3, and R 5 It is cyclopropyl, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0197] Table 1.77 provides compounds E77.1 to E77.952 of formula (Ia), where R 2 It is OCH3, and R 5 It is CH2OCH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0198] Table 1.78 provides compounds E78.1 to E78.952 of formula (Ia), where R 2 It is OCH3, and R 5 It is CH2OCH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0199] Table 1.79 provides compounds E79.1 to E79.952 of formula (Ia), where R 2 It is OCH3, and R 5 It is NHCH2CH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0200] Table 1.80 provides compounds E80.1 to E80.952 of formula (Ia), where R 2 It is OCH3, and R 5 It is NHCH2CH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0201] Table 1.81 provides compounds E81.1 to E81.952 of formula (Ia), where R 2 It is OCH2CH3, and R 5 It is CH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0202] Table 1.82 provides compounds E82.1 to E82.952 of formula (Ia), where R 2 It is OCH2CH3, and R 5 It is CH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0203] Table 1.83 provides compounds E83.1 to E83.952 of formula (Ia), where R 2 It is OCH2CH3, and R 5 It is OCH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0204] Table 1.84 provides compounds E84.1 to E84.952 of formula (Ia), where R 2 It is OCH2CH3, and R 5 It is OCH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0205] Table 1.85 provides compounds E85.1 to E85.952 of formula (Ia), where R 2 It is OCH2CH3, and R 5 It is cyclopropyl, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0206] Table 1.86 provides compounds E86.1 to E86.952 of formula (Ia), where R 2 It is OCH2CH3, and R 5 It is cyclopropyl, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0207] Table 1.87 provides compounds E87.1 to E87.952 of formula (Ia), where R 2 It is OCH2CH3, and R 5 It is CH2OCH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0208] Table 1.88 provides compounds E88.1 to E88.952 of formula (Ia), where R 2 It is OCH2CH3, and R 5 is CH2OCH3, A4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0209] Table 1.89 provides compounds E89.1 to E89.952 of formula (Ia), where R 2 It is OCH2CH3, and R 5 It is NHCH2CH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0210] Table 1.90 provides compounds E90.1 to E90.952 of formula (Ia), where R 2 It is OCH2CH3, and R 5 It is NHCH2CH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0211] Table 1.91 provides compounds E91.1 to E91.952 of formula (Ia), where R 2 It is CO2CH3, and R 5 It is CH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0212] Table 1.92 provides compounds E92.1 to E92.952 of formula (Ia), where R 2 It is CO2CH3, and R 5 It is CH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0213] Table 1.93 provides compounds E93.1 to E93.952 of formula (Ia), where R 2 It is CO2CH3, and R 5 It is OCH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0214] Table 1.94 provides compounds E94.1 to E94.952 of formula (Ia), where R 2 It is CO2CH3, and R 5 It is OCH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0215] Table 1.95 provides compounds E95.1 to E95.952 of formula (Ia), where R 2 It is CO2CH3, and R 5 It is cyclopropyl, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0216] Table 1.96 provides compounds E96.1 to E96.952 of formula (Ia), where R 2 It is CO2CH3, and R 5 It is cyclopropyl, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0217] Table 1.97 provides compounds E97.1 to E97.952 of formula (Ia), where R 2 It is CO2CH3, and R 5 It is CH2OCH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0218] Table 1.98 provides compounds E98.1 to E98.952 of formula (Ia), where R 2 It is CO2CH3, and R 5 It is CH2OCH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0219] Table 1.99 provides compounds E99.1 to E99.952 of formula (Ia), where R 2 It is CO2CH3, and R 5 It is NHCH2CH3, and A 4 CH is, R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0220] Table 1.100 provides compounds E100.1 to E100.952 of formula (Ia), where R 2 It is CO2CH3, and R 5 It is NHCH2CH3, and A 4 is N, and R 1a , R 3 , R 4 , A 2a , A 2b Table Z 1 As defined below.

[0221] Table 2.1 lists compounds F1.1 to F1.288 of formula (Ic). [ka] Provided, in the formula, R 2 H is R 5 It is CH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined in Table Z. More specifically, see Table Z. 2 R 3 and R 4 This also includes compounds in which R forms a ring together. In this case, the ring is R 3 and R 4 Column (Table Z) 2 ) shown, R 3 and R 4 The amide atoms are bonded together along the amide atom attached to the bicyclic core of formula (Ic). For example, R in compound F1.217 3 and R 4 Please refer to the column.

[0222] [Table 2-1]

[0223] [Table 2-2]

[0224] [Table 2-3]

[0225] [Table 2-4]

[0226] [Table 2-5]

[0227] Table 2-6

[0228] Table 2-7

[0229] Table 2-8

[0230] Table 2-9

[0231] Table 2-10

[0232] Table 2-11

[0233] Table 2-12

[0234] Table 2-13

[0235] Table 2-14

[0236] Table 2-15

[0237] [Table 2-16]

[0238] [Table 2-17]

[0239] Table 2.2 provides compounds F2.1 to F2.288 of formula (Ic), where R 2 H is R 5 It is OCH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0240] Table 2.3 provides compounds F3.1 to F3.288 of formula (Ic), where R 2 H is R 5 It is cyclopropyl, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0241] Table 2.4 provides compounds F4.1 to F4.288 of formula (Ic), where R 2 H is R 5 It is CH2OCH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0242] Table 2.5 provides compounds F5.1 to F5.288 of formula (Ic), where R 2 H is R 5 It is NHCH2CH3, and R 3 , R 4 , A 2a, A 2b , A 4 Table Z 2 As defined below.

[0243] Table 2.6 provides compounds F6.1 to F6.288 of formula (Ic), where R 2 It is CH3, and R 5 It is CH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0244] Table 2.7 provides compounds F7.1 to F7.288 of formula (Ia), where R 2 CH 3 And R 5 It is OCH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0245] Table 2.8 provides compounds F8.1 to F8.288 of formula (Ic), where R 2 It is CH3, and R 5 It is cyclopropyl, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0246] Table 2.9 provides compounds F9.1 to F9.288 of formula (Ia), where R 2 It is CH3, and R 5 It is CH2OCH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0247] Table 2.10 provides compounds F10.1 to F10.288 of formula (Ic), where R 2 It is CH3, and R 5 It is NHCH2CH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0248] Table 2.11 provides compounds F11.1 to F11.288 of formula (Ic), where R 2 It is CH2CH3, and R 5 It is CH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0249] Table 2.12 provides compounds F12.1 to F12.288 of formula (Ic), where R 2 It is CH2CH3, and R 5 It is OCH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0250] Table 2.13 provides compounds F13.1 to F13.288 of formula (Ic), where R 2 It is CH2CH3, and R 5 It is cyclopropyl, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0251] Table 2.14 provides compounds F14.1 to F14.288 of formula (Ic), where R 2 It is CH2CH3, and R 5It is CH2OCH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0252] Table 2.15 provides compounds F15.1 to F15.288 of formula (Ic), where R 2 It is CH2CH3, and R 5 It is NHCH2CH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0253] Table 2.16 provides compounds F16.1 to F16.288 of formula (Ic), where R 2 F is R 5 It is CH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0254] Table 2.17 provides compounds F17.1 to F17.288 of formula (Ic), where R 2 F is R 5 It is OCH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0255] Table 2.18 provides compounds F18.1 to F18.288 of formula (Ic), where R 2 F is R 5 It is cyclopropyl, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z2 As defined below.

[0256] Table 2.19 provides compounds F19.1 to F19.288 of formula (Ic), where R 2 F is R 5 It is CH2OCH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0257] Table 2.20 provides compounds F20.1 to F20.288 of formula (Ic), where R 2 F is R 5 It is NHCH2CH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0258] Table 2.21 provides compounds F21.1 to F21.288 of formula (Ic), where R 2 is Cl, and R 5 It is CH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0259] Table 2.22 provides compounds F22.1 to F22.288 of formula (Ic), where R 2 is Cl, and R 5 It is OCH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0260] Table 2.23 provides compounds F23.1 to F23.288 of formula (Ic), where R2 is Cl, and R 5 It is cyclopropyl, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0261] Table 2.24 provides compounds F24.1 to F24.288 of formula (Ic), where R 2 is Cl, and R 5 It is CH2OCH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0262] Table 2.25 provides compounds F25.1 to F25.288 of formula (Ic), where R 2 is Cl, and R 5 It is NHCH2CH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0263] Table 2.26 provides compounds F26.1 to F26.288 of formula (Ia), where R 2 is Br, R 5 It is CH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0264] Table 2.27 provides compounds F27.1 to F27.288 of formula (Ia), where R 2 is Br, R 5 It is OCH3, and R 3 , R 4 , A 2a , A2b , A 4 Table Z 2 As defined below.

[0265] Table 2.28 provides compounds F28.1 to F28.288 of formula (Ia), where R 2 is Br, R 5 It is cyclopropyl, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0266] Table 2.29 provides compounds F29.1 to F29.288 of formula (Ia), where R 2 is Br, R 5 It is CH2OCH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0267] Table 2.30 provides compounds F30.1 to F30.288 of formula (Ia), where R 2 is Br, R 5 It is NHCH2CH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0268] Table 2.31 provides compounds F31.1 to F31.288 of formula (Ia), where R 2 is CN, R 5 It is CH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0269] Table 2.32 provides compounds F32.1 to F32.288 of formula (Ia), where R 2 is CN, R 5 It is OCH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0270] Table 2.33 provides compounds F33.1 to F33.288 of formula (Ia), where R 2 is CN, R 5 It is cyclopropyl, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0271] Table 2.34 provides compounds F34.1 to F34.288 of formula (Ia), where R 2 is CN, R 5 It is CH2OCH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0272] Table 2.35 provides compounds F35.1 to F35.288 of formula (Ia), where R 2 is CN, R 5 It is NHCH2CH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0273] Table 2.36 provides compounds F36.1 to F36.288 of formula (Ia), where R 2 It is OCH3, and R 5 It is CH3, and R 3, R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0274] Table 2.37 provides compounds F37.1 to F37.288 of formula (Ia), where R 2 It is OCH3, and R 5 It is OCH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0275] Table 2.38 provides compounds F38.1 to F38.288 of formula (Ic), where R 2 It is OCH3, and R 5 It is cyclopropyl, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0276] Table 2.39 provides compounds F39.1 to F39.288 of formula (Ic), where R 2 It is OCH3, and R 5 It is CH2OCH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0277] Table 2.40 provides compounds F40.1 to F40.288 of formula (Ic), where R 2 It is OCH3, and R 5 It is NHCH2CH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2As defined below.

[0278] Table 2.41 provides compounds F41.1 to F41.288 of formula (Ic), where R 2 It is OCH2CH3, and R 5 It is CH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0279] Table 2.42 provides compounds F42.1 to F42.288 of formula (Ic), where R 2 It is OCH2CH3, and R 5 It is OCH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0280] Table 2.43 provides compounds F43.1 to F43.288 of formula (Ic), where R 2 It is OCH2CH3, and R 5 It is cyclopropyl, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0281] Table 2.44 provides compounds F44.1 to F44.288 of formula (Ic), where R 2 It is OCH2CH3, and R 5 It is CH2OCH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0282] Table 2.45 provides compounds F45.1 to F45.288 of formula (Ic), where R 2 It is OCH2CH3, and R 5 It is NHCH2CH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0283] Table 2.46 provides compounds F46.1 to F46.288 of formula (Ic), where R 2 It is CO2CH3, and R 5 It is CH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0284] Table 2.47 provides compounds F47.1 to F47.288 of formula (Ic), where R 2 It is CO2CH3, and R 5 It is OCH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0285] Table 2.48 provides compounds F48.1 to F48.288 of formula (Ic), where R 2 It is CO2CH3, and R 5 It is cyclopropyl, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0286] Table 2.49 provides compounds F49.1 to F49.288 of formula (Ic), where R 2 It is CO2CH3, and R 5It is CH2OCH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0287] Table 2.50 provides compounds F50.1 to F50.288 of formula (Ic), where R 2 It is CO2CH3, and R 5 It is NHCH2CH3, and R 3 , R 4 , A 2a , A 2b , A 4 Table Z 2 As defined below.

[0288] The compounds according to the present invention may have numerous advantages, including, in particular, advantageous levels of biological activity for protecting plants from fungal diseases, or excellent properties for use as agricultural chemical active ingredients (e.g., high biological activity, advantageous activity spectrum, increased safety profile, improved physicochemical properties, or improved biodegradability). The compounds according to the present invention have particularly advantageous levels of biological activity for protecting plants from oomycetes such as Phytophthora, Plasmopara, and Pythium.

[0289] Compounds of formula (I) where Z is O can be prepared as shown in schemes 1 to 18 below, where, unless otherwise specified, the definition of each variable site is as defined in this invention.

[0290] The compound of formula (I) is mixed with the compound of formula (II) where X is Cl, Br or I, in the presence of a base such as Cs2CO3, K2CO3 or NaOtBu and in the presence of a suitable palladium catalyst such as tetrakistriphenylphosphine palladium, [1,1-bis(diphenylphosphine)ferrocene]dichloropalladium(II), bis(diphenylphosphine)palladium(II) chloride, palladium dichloride or palladium acetate, in a suitable solvent such as dimethylformamide, dioxane, tetrahydrofuran, ethanol or water, and R 6 Either they are hydrogen, C1-C6 alkyl, or two R 6 It can be prepared by Suzuki cross-coupling with a compound of formula (III) that can combine to form a C3-C8 cycloalkyl group. 6 Hydrogen and C are independent of each other. 1-6 Alkyl or two R 6 together become C 3-8 Compounds of formula (III) that can form cycloalkyl groups are prepared by known methods or are commercially available. This transformation is shown in Scheme 1. [ka] Scheme 1

[0291] The compound of formula (II) is a compound of formula (IV) where X is Cl, Br or I. 1 It can be prepared by reacting a reagent of formula (V), in which is a good leaving group such as Cl, Br, I, triflate, tosyl, or mesyl, with a base such as Cs2CO3, K2CO3, NaH, or NaOtBu. 7 The amide nitrogen can be functionalized by using a compound of formula (VI) in which X is an electron-withdrawing group such as a cyano or ester. A compound of formula (IV) in which X is Cl, Br or I activates the carboxylic acid functional group of the compound of formula (VII), where X is Cl, Br or I, and X 2This peptide coupling reaction involves a compound of formula (VII) where is an OH group, and an amine of formula (VIII). By converting the -OH group of the carboxylic acid to a suitable leaving group such as a chloride group, for example by using (COCl)2 or SOCl2, the reaction can be prepared by a process commonly performed in the literature for amide coupling of 1-propanephosphonic acid cyclic anhydride (T3P) in a suitable solvent (e.g., acetonitrile), preferably in the presence of a base such as triethylamine or N,N-diisopropylethylamine, or optionally in the presence of a base (e.g., triethylamine or N,N-diisopropylethylamine), preferably at a temperature of 25°C to 60°C, before treatment with the amine of formula (VIII). See, for example, 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 is X 2 This can be obtained using the above conditions by amide coupling transformation of a compound of formula (VII), where is OH and X is Cl, Br, or I, with an amine of formula (IX). These transformations are shown in Scheme 2. [ka] Scheme 2

[0292] The compound of formula (IX) is commercially available, or it is a compound of formula (VIII) and formula (V) (wherein X 1 The compound of formula (IX) can also be obtained by reacting the compound of formula (VIII) with the compound of formula (VI) (wherein R is a good leaving group such as Cl, Br, I, triflate, tosyl, or mesyl) in the presence of a base such as Cs2CO3, K2CO3, NaH, or NaOtBu. Alternatively, the compound of formula (IX) can also be optionally obtained by reacting the compound of formula (VIII) with the compound of formula (VI) (wherein R is a good leaving group such as Cl, Br, I, triflate, tosyl, or mesyl) in the presence of a base such as triethylamine or 1,8-diazabicyclo[5.4.0]undeca-7-ene. 7The compound of formula (IX) can be synthesized by reacting it with an electron-withdrawing group (such as a cyano or ester). Alternatively, the compound of formula (IX) can be synthesized in a suitable solvent, optionally in the presence of a Brønsted acid or Lewis acid such as acetic acid, for example, in the presence of NaBH(OAc)3 or NaBH3CN, with an aldehyde of formula (X) (wherein R is the electron-withdrawing group). 11 C 1-5 Alkyl, C 1-6 Alkoxy-C 1-5 Alkyl, C 3-5 Cycloalkyl, C3-cycloalkyl-C 1-3 Alkyl, C 2-5 Alkenil, C 2-5 Alkinyl, C 1-5 Alkoxy, C 1-6 Alkylsulfanyl-C 1-5 Alkyl, C 1-6 Alkylsulfinyl-C 1-5 Alkyl, C 1-6 Alkylsulfonyl-C 1-5 Alkyl, C 1-6 Alkoxycarbonyl-C 1-5 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-5 Alkyl, diC 1-6 Alkylaminocarbonyl-C 1-5 It can be obtained from the amine of formula (VIII) by reductive amination with an alkyl or CN group. 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 shown in Scheme 3. [ka] Scheme 3

[0293] Alternatively, the compound of formula (II), where X is Cl, Br, or I, can 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 prepared by activating the carboxylic acid functional group of the compound of formula (XII), thereby reacting with the amine of formula (IX) and X 2 This is an amide coupling conversion with the compound of formula (XII) in which is OH, by converting the -OH of the carboxylic acid to a good leaving group such as a chloride group, for example by using (COCl)2 or SOCl2, before treatment with the amine of formula (IX), preferably in a suitable solvent (e.g., N-methylpyrrolidone, acetonitrile, dimethylacetamide, dichloromethane or tetrahydrofuran), preferably at a temperature of 25°C to 60°C, optionally in the presence of a base such as triethylamine or N,N-diisopropylethylamine, or optionally in the presence of a base (e.g., triethylamine or N,N-diisopropylethylamine), in a suitable solvent (e.g., acetonitrile), under conditions described in the literature for amide coupling with cyclic anhydride of 1-propanephosphonic acid (T3P). Alternatively, the compound of formula (XI) can be obtained by converting the compound of formula (XIII) to the compound of formula (V) (wherein X) in the presence of a base such as Cs2CO3, K2CO3, NaH or NaOtBu. 1 The compound of formula (XI) can also be obtained by alkylating it with a good leaving group such as Cl, Br, I, triflate, tosyl, or mesyl. Alternatively, the compound of formula (XI) can also be optionally obtained by alkylating the compound of formula (XIII) with the compound of formula (VI) (wherein R is present in the presence of a base such as triethylamine or 1,8-diazabicyclo[5.4.0]undeca-7-ene). 7 It can be synthesized by reacting it with an electron-withdrawing group such as a cyano or ester. The compound of formula (XIII) can be synthesized using the above conditions and the amine of formula (VIII) 2Compounds of formula (XII) where the OH group is can be prepared by peptide coupling transformations. These transformations are shown in Scheme 4. [ka] Scheme 4

[0294] Alternatively, the compound of formula (XI) can be synthesized by reacting the compound of formula (XIV) (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. This transformation is shown in Scheme 5. [ka] Scheme 5

[0295] Compound of formula (XIIa) (wherein each R 1 These are, independently of each other, 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, X 2 (where R is OH) is formed by using a base such as lithium hydroxide or sodium hydroxide to form an ester of formula (XVa) (where any R is 1 However, independently of each other, hydrogen, hydroxyl, halogen, CN, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, 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 Selected from alkyl, R 9 is C 1-6 It can be prepared by hydrolysis of the compound of formula (XVa) (wherein any of the R 1 However, independently of each other, hydrogen, hydroxyl, halogen, CN, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Selected from alkyl, R 9 is C 1-6 A compound of formula (XVII) (wherein any R is alkyl) is an alkyl compound of formula (XVII) 6 However, hydrogen and C are independent of each other. 1-6 Alkyl or two R 6 Together, C 3-8The compounds of formula (XVIa) (wherein X is Cl, Br, or I) can be obtained from a compound of formula (XVIa) (wherein X is Cl, Br, or I) by a cross-coupling transformation using a compound of formula (XVIII) (Suzuki cross-coupling), which can form a cycloalkyl group. The Suzuki cross-coupling can be achieved by using 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, in the presence of a base such as Cs2CO3, K2CO3, or NaOtBu. Still coupling can be achieved with a suitable palladium catalyst such as tetrakistriphenylphosphine palladium, tris(dibenzylideneacetone)dipalladium, palladium chloride, or palladium acetate, in the presence of a base such as Cs2CO3 or sodium acetate, and in a suitable solvent such as dimethylformamide, dioxane, or acetonitrile. Compound of formula (XVII) (wherein R 6 These are hydrogen and C, which are independent of each other. 1-6 Alkyl or two R 6 together become C 3-8 Compounds of formula (XVIII) (which can form cycloalkyl groups) are prepared by known methods or are commercially available. These transformations are shown in Scheme 6. [ka] Scheme 6

[0296] Alternatively, the compound of formula (XVa) (wherein each R 1 These are, independently of each other, hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Selected from alkyl, R 9 is C 1-6 (It is alkyl) is a compound of formula (XIXa) (wherein R 9 is C 1-6 From an alkyl group, in the presence of a base such as pyridine or diisopropylethylamine, a compound of formula (XX) (wherein X is Cl or Br, and R 8 is C 1-6 It can be obtained by reacting with an alkyl group. The amine (R) of formula (XIXa) 9 is C 1-6 (It is alkyl) is converted in a protic solvent such as methanol, an acid, typically hydrochloric acid, or sodium acetate and hydroxyamine hydrochloride to form a compound of formula (XXIa) (R 9 is C 1-6 It can be prepared by treating the compound of formula (XXIa) (wherein R 9 is C 1-6 The alkyl compound (wherein X is Cl, Br or I, and R) is formed in the presence of a catalyst such as palladium acetate or tris(dibenzylideneacetone)dipalladium, optionally a ligand such as 1,1'-[1,1'-binaphthalene]-2,2'-diylbis[1,1-diphenylphosphine] or (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine), and a base such as cesium carbonate or sodium tert-butoxide, forming the compound of formula (XVIa) (wherein X is Cl, Br or I, and R 9 is C 1-6 It can be synthesized by the reaction of an alkyl group with diphenylmethaneimine (CAS number 1013-88-3). These transformations are shown in Scheme 7. [ka] Scheme 7

[0297] Compound of formula (XVIa) (wherein X is Cl, Br or I, and R 9 is C1-6 (It is alkyl) is a compound of formula (XXIIa) (wherein X is Cl, Br or I, and R) in a solvent such as water, ethanol, acetone or acetonitrile. 9 is C 1-6 A compound of formula (XXIII) (wherein X is Cl, Br or I), or its corresponding acetal of formula (XXIV) (wherein X is Cl, Br or I, and any R 10 However, C 1-6 Alkyl or two R 10 Together, C 3-8 It can be synthesized by condensation with a compound that can form a cycloalkyl group. The reaction can be improved by using a base such as sodium bicarbonate or potassium carbonate, or by using an acid such as p-toluenesulfonic acid or hydrogen bromide. The compound of formula (XXIIa) (wherein X is Cl, Br, or I, and R) 9 is C 1-6 Compounds of formula (XXIII) (wherein X is Cl, Br or I), and compounds of formula (XXIV) (wherein X is Cl, Br or I, and any R 10 However, C 1-6 Alkyl or two R 10 They came together, C 3-8 These (which can form cycloalkyl groups) are commercially available or prepared using methods known to those skilled in the art. These conversions are shown in Scheme 8. [ka] Scheme 8

[0298] Compound of formula (XIVa) (wherein X is Cl, Br or I, and any of R) 1 However, independently of each other, hydrogen, hydroxyl, halogen, CN, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4Alkyl, 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 A compound (selected from alkyl) is commercially available or, in a solvent such as water, ethanol, acetone or acetonitrile, is mixed with an amine of formula (XXVa) (wherein X is Cl, Br or I) and a compound of formula (XXIII) (wherein X is Cl, Br or I), or its corresponding acetal of formula (XXIV) (wherein X is Cl, Br or I, and any R 10 However, C 1-6 Alkyl or two R 10 They came together, C 3-8 It can be prepared by condensation with a cycloalkyl group (which may form a cycloalkyl group). The reaction outcome can be improved by using a base such as sodium bicarbonate or potassium carbonate, or by using an acid such as p-toluenesulfonic acid or hydrogen bromide. Compounds of formula (XXVa) (wherein X is Cl, Br, or I) are commercially available or prepared using methods known to those skilled in the art. These transformations are shown in Scheme 9. [ka] Scheme 9

[0299] Compound of formula (XVb) (wherein R 9 is C 1-6 The alkyl compound (wherein R) is obtained by heating in a solvent such as toluene and optionally in the presence of an acid such as acetic acid, thereby forming the compound of formula (XXVI) (wherein R 9 is C 1-6 It can be prepared by condensation of a compound of formula (XXVII) (wherein R is alkyl). 9 C 1-6 Compounds of formula (XXVII), which are alkyl, can be commercially available or synthesized using methods known to those skilled in the art. This transformation is shown in Scheme 10. [ka] Scheme 10

[0300] Compound of formula (XVc) (wherein R 9 is C 1-6 (It is alkyl) is commercially available, or in a solvent such as water, ethanol, acetone, or acetonitrile, the amine of formula (XXVIII) (wherein R) 9 is C 1-6 A compound of formula (XXIII) (wherein X is Cl, Br or I), or its corresponding acetal of formula (XXIV) (wherein X is Cl, Br or I, and any R 10 However, C 1-6 Alkyl or two R 10 They came together, C 3-8 It can be prepared by condensation with a cycloalkyl group (which can form a cycloalkyl group). The reaction results can be improved by using a base such as sodium bicarbonate or potassium carbonate, or by using an acid such as p-toluenesulfonic acid or hydrogen bromide. Formula (XXVIII) (wherein R 9 C 1-6 Compounds (which are alkyl) are commercially available or prepared using methods known to those skilled in the art. These conversions are shown in Scheme 11. [ka] Scheme 11

[0301] Compound of formula (VII) (wherein X is Cl, Br or I, X 2 (where is OH) can be formed by using a base such as lithium hydroxide or sodium hydroxide to form an ester of formula (XXIX) (wherein X is Cl, Br or I, and R 9 is C 1-6 It can be prepared by hydrolysis of an alkyl group. Ester of formula (XXIX) (wherein X is Cl, Br or I, and R 9 is C 1-6A compound of formula (XV) (wherein R is alkyl) can be formed by using a halogenating agent such as N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, or bromine in a suitable solvent such as dichloromethane, chloroform, tetrahydrofuran, or acetonitrile. 9 is C 1-6 These can be obtained by halogenation of alkyl groups. These transformations are shown in Scheme 12. [ka] Scheme 12

[0302] Alternatively, the compound of formula (I) activates the carboxylic acid functional group of the compound of formula (XXX), thereby forming the amine of formula (IX) and X 2 This is an amide coupling conversion with a compound of formula (XXX) where is OH, by converting the -OH of the carboxylic acid to a good leaving group such as a chloride group, for example by using (COCl)2 or SOCl2, before treatment with the amine of formula (IX), preferably in a suitable solvent (e.g., N-methylpyrrolidone, acetonitrile, dimethylacetamide, dichloromethane or tetrahydrofuran), preferably at a temperature of 25°C to 60°C, optionally in the presence of a base such as triethylamine or N,N-diisopropylethylamine, or optionally in the presence of a base (e.g., triethylamine or N,N-diisopropylethylamine), in a suitable solvent (e.g., acetonitrile), under conditions described in the literature for amide coupling with cyclic anhydride of 1-propanephosphonic acid (T3P). Alternatively, the compound of formula (I) can be converted to the compound of formula (XXXI) (wherein X) in the presence of a base such as Cs2CO3, K2CO3, NaH or NaOtBu. 1 The compounds of formula (I) can also be prepared by alkylation with a good leaving group such as Cl, Br, I, triflate, tosyl, or mesyl. Alternatively, the compounds of formula (XXXI) can also be optionally prepared by alkylating them with a base such as triethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene.7 It can be synthesized by reacting with a compound of formula (VI) in which X is an electron-withdrawing group such as a cyano or ester. The compound of formula (XXXI) can be synthesized by reacting with a compound of formula (XXX) (wherein X) using the above conditions. 2 It can be synthesized from the amine of formula (VIII) (where is OH) by peptide coupling transformation. These transformations are shown in Scheme 13. [ka] Scheme 13

[0303] Compound of formula (XXX) (wherein X 2 (where R is OH) is a compound of formula (XXXII) (where R is OH) 9 is C 1-6 It can be obtained by hydrolysis of the ester portion (which is alkyl). 9 C 1-6 Compounds of formula (XXXII) that are alkyl are prepared in the presence of a base such as Cs2CO3, K2CO3, or NaOtBu, and in the presence of a suitable palladium catalyst such as 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, where X is Cl, Br, or I, and R 9 C 1-6 Compounds of formula (XXIX) that are alkyl, and R 6 Hydrogen and C are independent of each other. 1-6 Alkyl or two R 6 together become C 3-8 These compounds can be obtained by Suzuki cross-coupling them with compounds of formula (III) that can form cycloalkyl groups. These transformations are shown in Scheme 14. [ka] Scheme 14

[0304] Alternatively, the compound of formula (I) can be synthesized by reacting the compound of formula (XXXIII) (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 (XXXIII) where X is Cl, Br, or I can be synthesized 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, in a suitable solvent such as dimethylformamide, dioxane, tetrahydrofuran, ethanol, or water, where any X is independently reacted with any R from the compound of formula (XXXIV) where any X is Cl, Br, or I. 6 Hydrogen and C are independent of each other. 1-6 Alkyl or two R 6 together become C 3-8 These compounds can be prepared by Suzuki cross-coupling with a compound of formula (III) that can form a cycloalkyl group. These transformations are shown in Scheme 15. [ka] Scheme 15

[0305] Alternatively, the compound of formula (I) can be used in a peptide coupling transformation using the above conditions, with the compound of formula (XXXV) and the compound of formula (XXXVI) (wherein X 2The compound of formula (XXXV) can be prepared by reaction with (where is OH). The compound of formula (XXXV) 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(diphenylphosphino)ferrocene]dichloropalladium(II), bis(diphenylphosphine)palladium(II) chloride, palladium dichloride or palladium acetate, in a suitable solvent such as dimethylformamide, dioxane, tetrahydrofuran, ethanol or water, and R 6 Hydrogen and C are independent of each other. 1-6 Alkyl or two R 6 together become C 3-8 It can be prepared by Suzuki cross-coupling with a compound of formula (XXXVII) that can form a cycloalkyl group. 6 Either they are hydrogen, C1-C6 alkyl, or two R 6 Compounds of formula (XXXVII) that can combine to form C3-C8 cycloalkyl groups are prepared by known methods or are commercially available. These transformations are shown in Scheme 16. [ka] Scheme 16

[0306] Compounds of formula (Ib) where Z is S can be prepared by reacting a compound of formula (I) where Z is O with phosphorus pentasulfide or Lawson's reagent (CAS: 19172-47-5) in a suitable solvent such as toluene, xylene, or dichloromethane. This conversion is shown in Scheme 17. [ka] Scheme 17

[0307] Alternatively, a compound of formula (Ib) where Z is S can be used in a peptide coupling transformation using the above conditions, with a compound of formula (XXXVb) and a compound of formula (XXXVI) (where X is X). 2It can be prepared by reaction with (where is OH). The compound of formula (XXXVb) can be prepared by reacting the compound of formula (XXXV) with phosphorus pentasulfide or Lawson's reagent (CAS: 19172-47-5) in a suitable solvent such as toluene, xylene, or dichloromethane. This conversion is shown in Scheme 18. [ka] Scheme 18

[0308] It will be understood by those skilled in the art that the above amide coupling reactions between acids, amines, and coupling agents can also be carried out using the corresponding acid chlorides and amines. The conversion of acids to their corresponding acid chlorides is well known by those skilled in the art.

[0309] When the term "compound according to the present invention" is used, it refers to the compound according to the present invention.

[0310] Alternatively, the compounds according to the present invention can be obtained by transformations using standard synthetic techniques known to those skilled in the art. Non-exclusive examples include oxidation reactions, reduction reactions, hydrolysis reactions, coupling reactions, aromatic nucleophilic or electrophilic substitution reactions, nucleophilic substitution reactions, nucleophilic addition reactions, olefination reactions, oxime formation, alkylation, and halogenation reactions.

[0311] The compounds according to the present invention can be converted to other compounds according to the present invention in a manner known by means of substituting one or more substituents of the starting compound according to the present invention with other substituents according to the present invention in a conventional manner.

[0312] Depending on the selection of suitable reaction conditions and starting materials in each case, it may be possible, for example, to substitute only one substituent with another substituent according to the present invention in a single reaction step, or to substitute multiple substituents with other substituents according to the present invention in the same reaction step.

[0313] 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.

[0314] The salts of the compounds according to the present invention can be converted to the free compounds by conventional methods, for example, by treating the acid addition salt with a suitable basic compound or a suitable ion exchange reagent, and by treating the salt with a base with a suitable acid or a suitable ion exchange reagent.

[0315] Salts of the compounds according to the present invention can be converted in a manner known in itself to other salts of the compounds according to the present invention (acid addition salts, e.g., other acid addition salts) by treating a salt of an inorganic acid such as hydrochloric acid with a suitable metal salt of the acid such as sodium, barium, or silver salt (e.g., silver acetate) in a suitable solvent (e.g., in which the inorganic salt forming silver chloride is insoluble and therefore precipitates from the reaction mixture).

[0316] Depending on the method or reaction conditions, the compounds according to the present invention that have salt-forming properties can be obtained in free form or salt form.

[0317] The compounds according to the present invention, and optionally their tautomers, may exist in free or salt form, 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 stereoisomers such as enantiomers and / or diastereomers, or as mixtures of enantiomers, such as racemic compounds, diastereomer mixtures, or racemic compound mixtures, in one form of a possible stereoisomer or as a mixture thereof. The present invention relates to pure stereoisomers and to all possible mixtures of stereoisomers, and should be understood in this sense above and below, respectively, even if the details of stereochemistry are not specifically described for each.

[0318] The diastereomer or racemic mixture of compounds according to the present invention, in the free or salt form obtained depending on the selected starting materials and procedure, can be separated into pure diastereomers or racemic compounds based on the physicochemical differences of the components by known methods, such as fractional crystallization, distillation and / or chromatography.

[0319] Enantiomer mixtures such as racemates, which can be obtained by similar methods, can be separated into optical enantiomers by known methods, for example by recrystallization from an optically active solvent, by chromatography on a chiral adsorbent, for example by high-performance liquid chromatography (HPLC) on acetylcellulose with the help of suitable microorganisms, by cleavage with a specific immobilized enzyme, by the formation of an inclusion compound, for example by complexing with only one enantiomer, using a chiral crown ether, or by conversion to a diastereomer salt, for example by reacting a racemate, which is a basic final product, with an optically active acid, for example a carboxylic acid, for example camphor, tartaric acid, or malic acid, or a sulfonic acid, for example 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).

[0320] Pure diastereomers or enantiomers can be obtained according to the present invention not only by separating a suitable mixture of stereoisomers, but also by generally known diastereoselective or enantioselective synthesis methods, such as the method according to the present invention using suitable stereochemical starting materials.

[0321] 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.

[0322] When individual components have different biological activities, it is advantageous to isolate or synthesize the more biologically effective stereoisomers, such as enantiomers or diastereomers, or stereoisomer mixtures, such as enantiomer mixtures or diastereomer mixtures, in each case.

[0323] The compounds according to the present invention and optionally their tautomers may be obtained in free form or salt form, optionally in hydrate form, and / or in other solvents, such as solvents that have been used to crystallize compounds existing in solid form.

[0324] The following examples illustrate, but are not limiting, the present invention.

[0325] The present invention also provides intermediates useful for the preparation of compounds according to the present invention.

[0326] The following intermediates form further embodiments of the present invention.

[0327] Compound of formula (XXX) [ka] (In the formula, each A 1 is either N or one A 1 is N, and one A 1 CR 1 And; preferably, one A 1 is N, and one A 1 CR 1 and; R 1 These are hydrogen, hydroxyl, halogen, CN, and C 1-6Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and -NHC(O)C 1-6 Selected independently of alkyl; preferably R 1 is hydrogen and C 1-6 Selected independently of alkyl; A 4 is either CH or N; R 5 C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, diC 1-6 Alkylamino, C 1-6 Alkoxyaminos and C 1-6 Alkyl C 1-6 Selected from alkoxyaminos, where C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, diC 1-6 Alkylamino, C 1-6 Alkoxyaminos and C 1-6 Alkyl C 1-6 Each alkoxyamino group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN. or its salt or N-oxide.

[0328] Compound of formula (XI) [ka] (In the formula, each A 1 is either N or one A 1 is N, and one A 1 CR 1 And; preferably, one A 1 is N, and one A 1 CR 1 and; R 1 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 sulfonyl, C 1-6 Alkoxy, amino, and -NHC(O)C 1-6 Selected independently of alkyl; preferably R 1 is hydrogen and C 1-6 Selected independently of alkyl; A 2 CR is independent 2 or N, provided there are 3 or fewer A 2 is N, preferably 4 A 2 CR 2 and; R 2 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 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, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, C 1-6 Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents selected from halogen, hydroxyl, and CN; preferably, R 2 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, and C 1-6 Alkoxy-C 1-6 Selected independently of alkyl; A 3 CR 3 or N; R 3 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkylsulfonyl, amino, C 1-6 Alkylamino, diC 1-6 -alkylamino and C 3-6 Selected from cycloalkylaminos, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, 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 selected from halogens, hydroxyls, and CNs; preferably, R 3 is hydrogen; R 4C 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 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl, diC 1-6 Alkylaminocarbonyl-C 1-6 Selected from alkyl and CN, where C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 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 selected from halogens and CN; preferably, R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy, where C 1-6 Alkyl, C 1-6 Alkoxy-C1-6 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; Here, A 3 and R 4 (These elements can optionally come together to form a ring, preferably a six-membered heteroring.) or its salt or N-oxide.

[0329] Compound of formula (II) [ka] (In the formula, each A 1 is either N or one A 1 is N, and one A 1 CR 1 And; preferably, one A 1 is N, and one A 1 CR 1 and; R 1 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 sulfonyl, C 1-6 Alkoxy, amino, and -NHC(O)C 1-6 Selected independently of alkyl; preferably R 1 is hydrogen and C 1-6 Selected independently of alkyl; A 2 CR is independent 2 or N, provided there are 3 or fewer A 2 is N, preferably 4 A 2 CR 2 and; R 2Hydrogen, hydroxyl, halogen, CN, C1-6 alkyl, C1-6 alkoxy, C1-6 alkoxy-C1-6 alkyl, C1-6 alkoxy-C1-6 alkoxy, C 3-6 A cycloalkyl group is independently selected from C1-6 alkylsulfonyl groups, C1-6 alkoxycarbonyl groups, C1-6 alkylaminocarbonyl groups, diC1-6 alkylaminocarbonyl groups, and C1-6 alkylcarbonyl groups, where C1-6 alkyl, C1-6 alkoxy, C1-6 alkoxy-C1-6 alkyl, C1-6 alkoxy-C1-6 alkoxy, C 3-6 Each of the cycloalkyl, C1-6 alkylsulfonyl, C1-6 alkoxycarbonyl, C1-6 alkylaminocarbonyl, diC1-6 alkylaminocarbonyl, and C1-6 alkylcarbonyl groups may be optionally substituted with 1 to 3 substituents selected from halogen, hydroxyl, and CN; preferably, R 2 This is independently selected from hydrogen, halogen, CN, C1-6 alkyl, C1-6 alkoxy, and C1-6 alkoxy-C1-6 alkyl; A 3 CR 3 or N; R 3 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkylsulfonyl, amino, C 1-6 Alkylamino, diC 1-6 -alkylamino and C 3-6 Selected from cycloalkylaminos, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkylsulfonyl, amino, C 1-6 Alkylamino, diC 1-6 -alkylamino and C 3-6Each of the cycloalkylamino groups may be optionally substituted with 1 to 3 substituents selected from halogens, hydroxyls, and CNs; preferably, R 3 is hydrogen; R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl, diC 1-6 Alkylaminocarbonyl-C 1-6 Selected from alkyl and CN, where C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 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 selected from halogens and CN; preferably, R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy, where C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Each alkoxy group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN; Here, A 3 and R 4 They can optionally come together to form a ring, preferably a six-membered heteroring; X is Cl, Br, or I. or its salt or N-oxide.

[0330] 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 a large number of cultivated plants. The compounds of formula (I) as defined in this invention can also be used to suppress or eradicate pathogens appearing on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of different crops of useful plants, while simultaneously protecting those parts of the plant that will grow later from plant pathogenic microorganisms.

[0331] Compounds of formula (I) as defined in the present invention may also be used as mycicides. As used herein, the term “mycicide” means a compound that controls, modifies, or prevents the growth of fungi. The term “mycicidal amount” means the amount of such compound or combination of such compounds that can produce an effect against the growth of fungi. Controlling or modifying effects include all deviations from natural occurrence, such as death or delay, and prevention includes the formation of barriers or other defenses in or on plants to prevent fungal infection.

[0332] For protection against fungal infections and plant pathogenic fungi occurring 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, fruits, tubers, or grains, or plant cuttings (e.g., rice). The propagation material may be treated with a composition containing the compound of formula (I) as defined in this invention before planting, for example, seeds may be coated before sowing. The 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 methods for treating such plant propagation materials and to plant propagation materials thus treated.

[0333] Furthermore, the compounds of formula (I) as defined in the present invention can be used to control fungi in related fields, for example, in the protection of industrial materials including wood and wood-related industrial products, food storage, and hygiene management.

[0334] Furthermore, the present invention can also be used to protect non-biological materials, such as sawn timber, wall coverings, and paints, from fungal attacks.

[0335] The compounds of formula (I) as defined in this invention, and fungicidal compositions containing them, can be used to control plant diseases caused by broad-spectrum fungal plant pathogens. They are effective in controlling a wide range of plant diseases, including leaf pathogens of ornamental plants, turfgrasses, vegetables, crops, grains, and fruit crops.

[0336] The fungi and fungal vectors, as well as plant pathogenic bacteria and viruses, that can be controlled for these diseases include, for example, the following: This includes species such as Absidia corymbifera, Alternaria spp., Aphanomyces spp., Ascochyta spp., Aspergillus spp. (including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus), Aureobasidium spp. (including A. pullulans), Blastomyces dermatitidis, Blumeria graminis, and Bremia lactucaea. Species of the genus Botryosphaeria, including B. lactucae, B. dothidea, and B. obtusa; species of the genus Botrytis, including B. cinerea; species of Candida, including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, and C. tropicalis; species of Cephaloascus fragrans and Ceratocystis. Species of the genus Cercospora (spp.), including C. arachidicola, Cercosporidium personatum, species of the genus Cladosporium (spp.), Claviceps purpurea, Coccidioides immitis, species of the genus Cochliobolus (spp.), and species of the genus Colletotrichum (spp.), including C. musae. Cryptococcus neoformans, species of the genus Diaporthe, species of Didymella, species of Drechslera, species of Elsinoe, Species of the genus Epidermophyton (spp.), Erwinia amylovora, and Erysiphe species (spp.), including E. cichoracearum. Fusarium spp., including species of the genus Fusarium such as Eutypa lata, F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, and F. solani, as well as Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, and Glomerella singlet. * cingulate*, * Guignardia bidwellii*, * Gymnosporangium juniperi-virginianae*, species of the genus * Helminthosporium*, species of the genus * Hemileia*, species of the genus * Histoplasma* including * H. capsulatum*, * Laetisaria fuciformis*, * Leptographium lindbergi*, * Leveillula taurica*, * Lophodermium seditiosum*, wheat mold fungus (* Microdochium nivale*), species of the genus * Microsporum* This includes species of the genus Monilinia (spp.), species of the genus Mucor (spp.), wheat leaf spot fungus (M. graminicola), and species of the genus Mycosphaerella (spp.), including M. pomi.), Oncobasidium theobromaeon, Ophiostoma piceae, species of the genus Paracoccidioides spp., species of the genus Penicillium including P. digitatum and P. italicum, species of the genus Petriellidium spp., species of the genus Peronosclerospora including P. maydis, P. philippinensis and P. sorghi, species of the genus Peronospora spp., species of Peronospora, wheat blight fungus (Phaeosphaeria) Species of the genera *Phakopsora nodorum*, *Phakopsora pachyrhizi*, *Phellinus igniarus*, *Phialophora spp.*, *Phoma spp.*, *Phytophthora spp.* including *Phomopsis viticola* and *P. infestans*, *Plasmopara spp.* including *P. halstedii* and *P. viticola*, *Pleospora spp.*, and *Podosphaera spp.* including apple powdery mildew fungus (*P. leucotricha*). spp.), Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, species of the genus Pseudomonas (Pseudomonas spp.), species of the genus Pseudoperonospora including P. cubensis, P. humuli (Pseudoperonospora spp.), Pseudopeziza tracheiphila, P. hordei (P.Puccinia spp., including P. hordei, P. recondita, P. striiformis, P. triticina; Pyrenopeziza spp., Pyrenophora spp., Pyricularia spp., including P. oryzae; Pythium spp., including P. ultimum; Ramularia spp.; Rhizoctonia spp.; Rhizomucor pusillus; Rhizopus arizus This includes species of the genus Rhynchosporium (including *arrhizus*), species of the genus Sedosporium (including *S. apiospermum* and *S. prolificans*), and *Schizothyrium pomi*. Species of the genera Sclerotinia, Sclerotium, Septoria (including S. nodorum and S. tritici), Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix, Stagonospora nodorum, Stemphylium, Stereum hirsutum, and Thanatephorus ccumeris. This includes species of the genus *Tilletia* (including *Tilletia cucumeris*), *Tilletia basicola*, *Tilletia spp.*, *Tilletia harzianum*, *Tilletia pseudokoningii*, and *Tilletia viride*, as well as species of the genus *Trichoderma* (including *Tilletia viride*). Species of the genera Trichophyton, Typhula, Uncinula necator, Urocystis, Ustilago, Venturia (including V. inaequalis), Verticillium, and Xanthomonas.

[0337] In particular, compounds of formula (I) as defined in the present invention, and fungicidal compositions containing them, can be used to control plant diseases caused by broad-spectrum fungal plant pathogens in basidiomycetes, ascomycetes, oomycetes and / or deuteromycetes, blasocladiomycetes, chytridiomycetes, glomeromycetes and / or mucoromycetes. More specifically, compounds of formula (I) as defined in the present invention can be used to control oomycetes.

[0338] These pathogens may include the following: Diseases of the genus Phytophthora, including those caused by the Oomycete class, such as Phytophthora capsici, Phytophthora infestans, Phytophthora sojae, Phytophthora fragariae, Phytophthora nicotianae, Phytophthora cinnamomi, Phytophthora citricola, Phytophthora citrophthora, and Phytophthora erythroseptica; and Pythium aphanidermatum. Pythium diseases, such as those caused by Pythium aphanidermatum, Pythium arrhenomanes, Pythium graminicola, Pythium irregulare, Pythium sylvaticum, and Pythium ultimum; Peronospora destructor, Peronospora parasitica, Plasmopara viticola, Plasmopara halstedii, Pseudoperonospora cubensis, and Albugo candida. Diseases caused by Peronosporales species such as *Candida*, *Sclerophthora macrospora*, and *Bremia lactucae*;Also, other species such as Aphanomyces cochlioides, Labyrinthula zosterae, Peronosclerospora sorghi, and Sclerospora graminicola.

[0339] The class Ascomycetes includes the following: for example, Stemphylium solani, Stagonospora tainanensis, Spirocaea oleaginea, Setosphaeria turcica, Pyrenochaeta lycoperisici, Pleospora herbarum, Phoma destructiva, Phaeosphaeria herpotrichoides, Phaeocryptocus gaeumannii, Ophiosphaerella graminicola, and Ophiobolus graminis. graminis), Leptosphaeria maculans, Hendersonia creberrima, Helminthosporium triticirepentis, Setosphaeria turcica, Drechslera glycines, Didymella bryoniae, Cycloconium oleagineum, Corynespora cassiicola, Cochliobolus sativus, Bipolaris cactivora, Apple scab fungus (Venturia inaequalis), Pyrenophora teres), wheat yellow spot disease fungus (Pyrenophora tritici-repentis), Alternaria alternata, Alternaria brassisicola (AlternariaPleosporales species such as brassicicola, Alternaria solani, and Alternaria tomatophila; Septoria tritici, Septoria nodorum, Septoria glycines, Cercospora arachidicola, Cercospora sojina, Cercospora zeae-maydis, Cercosporella capsellae, and Cercosporella herpotrichoides, Cladosporium carpophilum, and Cladosporium efsum effusum), Passalora fulva, Cladosporium oxysporum, Dothistroma septosporum, Isariopsis clavispora, Mycosphaerella fijiensis, Mycosphaerella graminicola, Mycovellosiella koepkeii, Phaeoisariopsis bataticola, Pseudocercospora vitis, Pseudocercosporella herpotrichoides, Ramularia veticola Capnodiales, including beticola and Ramularia collo-cygni; Gaeumannomyces graminis.Magnaporthales species such as graminis, Magnaporthe grisea, and Pyricularia oryzae (rice blast fungus); Anisogramma anomala, Apiognomonia errabunda, Cytospora platani, Diaporthe phaseolorum, Discula destructiva, Gnomonia fructicola, Greeneria uvicola, Melanconium juglandinum, Phomopsis viticola, and Sirococcus clavigignenti juglandacearum. Diaporthales species such as clavigignenti-juglandacearum, Tubakia dryina, Dicarpella spp., and Valsa ceratosperma; as well as Actinothyrium graminis, Ascochyta pisi, Aspergillus flavus, Aspergillus fumigatus, Aspergillus nidulans, Asperisporium caricae, Blumeriella jaapii, Candida spp., and Capnodium ramosum. ramosum), species of the genus Cephaloascus (Cephaloascus spp.), Cephalosporium gramineum, Ceratocystis paradoxa, species of the genus Chaetomium (Chaetomium)spp.), Hymenoscyphus pseudoalbidus, species of the genus Coccidioides, Cylindrosporium padi, Diplocarpon malae, Drepanopeziza campestris, Elsinoe ampelina, Epicoccum nigrum, species of the genus Epidermophyton, Eutypa lata, Geotrichum candidum, Gibellina cerealis, Gloeocercospora sorghum Others include Gloeodes pomigena, Gloeosporium perennans, Gloeotinia temulenta, Griphospaeria corticola, Kabatiella lini, Leptographium microsporum, Leptosphaerulinia crassiasca, Lophodermium seditiosum, Marssonina graminicola, Microdochium nivale, Monilinia fructicola, and Monographella albecens. albescens), Monosporascus cannonballus, species of the genus Naemacyclus, Ophiostomanovo-ulmi, Paracoccidioides brasiliensis, Penicillium expansum, Pestalotia rhododendri, species of the genus Petriellidium, species of the genus Pezicula, Phialophora gregata, Phyllachora pomigena, Phymatotrichum omnivora, Physalospora abdita, Plectosporium tabacinum, Polyscytalum pustulans, Pseudopeziza medicaginis (medicaginis), Pyrenopeziza brassicae, Ramulispora sorghi, Rhabdocline pseudotsugae, Rhynchosporium secalis, Sacrocladium oryzae, species of the genus Scedosporium, Schizothyrium pomi, Sclerotinia sclerotiorum, Sclerotinia minor, species of the genus Sclerotium, Typhula ishikariensis, Seimatosporium marie Lepteutypa cupressi, Septocyta ruborum, Sphaceloma perseae, Sporonema phacidioides, Stigmina palmiboraDiseases such as spot, leaf spot, blast, or canker and / or rot caused by palmivora, Tapesia yallundae, Taphrina bullata, Thielviopsis basicola, Trichoseptoria fructigena, Zygophiala jamaicensis; for example, Blumeria graminis, Erysiphe polygoni, Uncinula necator, Sphaerotheca fuligena, apple powdery mildew (Podosphaera leucotricha), and Podospaera maculalis. Powdery mildew diseases caused by Erysiphales, such as those caused by species like macularis, Golovinomyces cichoracearum, Leveillula taurica, Microsphaera diffusa, Oidiopsis gossypii, Phyllactinia guttata, and Oidium arachidis; for example, Dothiorella aromatica, Diplodia seriata, Guignardia bidwellii, Botrytis cinerea, and Botryotinia arii. allii), Botryotinia fabae, Fusicoccum amygdali, Lasiodiplodia theobromae, Macrophoma theicola, Macrophomina phaseolinaFungi such as those caused by Botryosphaeriales, such as Phaseolina and Phyllosticta cucurbitacearum; anthracnose caused by the genus Glommerelales, such as Colletotrichum gloeosporioides, Colletotrichum lagenarium, Colletotrichum gossypii, Glomerella cingulata and Colletotrichum graminicola; and fungi such as Acremonium strictum, Claviceps purpurea, and Fusarium curmorum. Fusarium culmorum, Fusarium graminearum, Fusarium virguliforme, Fusarium oxysporum, Fusarium subglutinans, Fusarium oxysporum f.sp.cubense, Gerlachia nivale, Gibberella fujikuroi, Gibberella zeae, species of the genus Gliocladium, Myrothecium verrucaria, Nectria ramulariae, Trichoderma viride Wilt or canker disease, such as those caused by Hypocreales, including Trichothecium roseum and Verticillium theobromae.

[0340] Basidiomycete, which includes the following: smut fungi such as those caused by the order Ustilaginales, such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, and Ustilago zeae; and Puccinia arachidis, Puccinia cacabata, and Puccinia graminis. Puccinia graminis), Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia striiformis f.sp. Hordei, Puccinia striiformis f.sp.Pucciniales, including species such as Secalis, Pucciniastrum coryli, or Cronartium ribicola, Gymnosporangium juniperi-viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor, and Uromyces vizie-fabie. Rust fungi such as those caused by the order Uredinales (viciae-fabae), as well as species of the genus Cryptococcus, Exobasidium vexans, Marasmiellus inoderma, Mycena, Sphacelotheca reiliana, Typhula ishikariensis, Urocystis agropyri, Itersonilia perplexans, Corticium invisum, Laetisaria fuciformis, and Waitea cylinata. Other rot and disease-causing fungi, such as those caused by *Tilletiia circinata*, *Rhizoctonia solani* (rice sheath blight), *Thanetephorus cucurmeris* (sugar beet root rot), *Entyloma dahliae*, *Entylomella microspora*, *Neovossia moliniae*, and *Tilletiia caries*.

[0341] Blastocladiomycetes, such as Physoderma maydis.

[0342] Choanephora cucurbitarum; species of the genus Mucor; and Mucoromycete species such as Rhizopus arrhizus.

[0343] Furthermore, diseases caused by other species and genera closely related to those listed above.

[0344] In addition to their fungicidal activity, compositions comprising the compounds defined in the present invention and the compound of formula (I) may also be active against bacteria such as Erwinia amylovora, Erwinia caratovora, Xanthomonas campestris, Pseudomonas syringae, Streptomyces scabies, and other related species, as well as certain protozoa.

[0345] Within the scope of the present invention, target crops and / or useful plants to be protected are typically berry plants, e.g., blackberries, blueberries, cranberries, raspberries and strawberries; cereals, e.g., barley, corn, millet, oats, rice, rye, sorghum, rye and wheat; fiber plants, e.g., cotton, flax, hemp, jute and sisal; crops, e.g., sugar and fodder beets, coffee, hops, mustard, rapeseed (canola), poppies, sugarcane, sunflowers, tea and tobacco; fruit trees, e.g., apples, apricots, avocados, bananas, cherries, citrus fruits, nectarines, peaches, pears and plums; grasses, e.g., Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St. Augustine grass and zoysia grass Herbs, such as basil, borage, chives, coriander, lavender, lavender, mint, oregano, parsley, rosemary, sage, and thyme; legumes, such as kidney beans, lentils, peas, and soybeans; nuts, such as almonds, cashews, peanuts, hazelnuts, peanuts, pecans, pistachios, and walnuts; palms, such as oil palms; ornamental plants, such as flowers, shrubs, and trees; other trees, such as cocoa, coconuts, olives, and rubber trees; vegetables, such as asparagus, eggplant, broccoli, cabbage, carrots, cucumbers, garlic, lettuce, mallow, melon, okra, onions, peppers, potatoes, pumpkins, rhubarb, spinach, and tomatoes; and climbing plants, such as grapes and other perennial and annual crops.

[0346] Useful plants and / or target crops according to the present invention include conventional varieties such as insect-resistant (e.g., Bt. and VIP varieties), disease-resistant, herbicide-resistant (e.g., glyphosate- and glufosinate-resistant maize varieties, commercially available under trade names RoundupReady® and LibertyLink®), and nematode-resistant varieties, as well as genetically enhanced or genetically modified varieties. As an example, suitable genetically enhanced or genetically modified crop varieties include Stoneville 5599BR cotton and Stoneville 4892BR cotton varieties.

[0347] The terms “useful plants” and / or “target crops” should be understood to also include useful plants that have been given resistance to herbicides such as bromoxynil or certain classifications of herbicides (e.g., HPPD inhibitors, ALS inhibitors such as primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovir-sikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors, or PPO (protoporphyrinogen-oxidase) inhibitors) by conventional crossbreeding or genetic engineering methods. An example of a crop that has been given resistance to imidazolinones, such as imazamox, by conventional breeding (mutation) methods is Clearfield® summer rapeseed (canola). Examples of crops in which resistance to herbicides or certain classes of herbicides has been induced through genetic engineering include glyphosate- and glufosinate-resistant maize varieties marketed under trade names RoundupReady®, Herculex I®, and LibertyLink®.

[0348] 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 using recombinant DNA technology to enable, for example, the synthesis of one or more selectively acting toxins, such as those known to be derived from toxin-producing bacteria. Examples of toxins that may be expressed include δ-endotoxin, vegetative insecticidal protein (Vip), insecticidal proteins from nematode-symbiotic bacteria, and toxins produced by scorpions, spiders, wasps, and fungi. An example of a crop modified to express Bacillus thuringiensis toxin is Bt maize KnockOut® (Syngenta Seeds). An example of a crop containing two or more genes encoding insecticide resistance and therefore expressing two or more toxins is VipCot® (Syngenta Seeds). Crops or their seed materials can also be resistant to multiple types of pests (so-called superimposed transgenic events when genetically modified). For example, plants can have the ability to express insecticidal proteins and be resistant to herbicides, such as Herculex I® (registered trademark) (Dow AgroSciences, Pioneer Hi-Bred International).

[0349] The terms “useful plants” and / or “target crops” should be understood to also include useful plants transformed using recombinant DNA technology to enable the synthesis of selectively acting antipathogenic substances, such as so-called “infection-specific proteins” (PRPs, see, e.g., European Patent Application Publication No. 0 392 225). Examples of such antipathogenic substances and transgenic plants capable of synthesizing such antipathogenic substances are known, for example, from European Patent Application Publication No. 0 392 225, International Publication No. 95 / 33818 and European Patent Application Publication No. 0 353 191. Methods for producing such transgenic plants are generally known to those skilled in the art and are described, for example, in the aforementioned publications.

[0350] Toxins that can be expressed by transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis such as δ-endotoxins like Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C; or vegetative insecticidal proteins (Vip) such as Vip1, Vip2, Vip3 or Vip3A; or species of the genus Photorhabdus, such as Photorhabdus luminescens or Xenorhabdus nematophilus, for example Photorhabdus spp. or Xenorhabdus Insecticidal proteins of nematode-symbiotic bacteria such as spp.; toxins produced by animals such as scorpion toxin, spider toxin, large wasp (wasp) toxin and other insect-specific neurotoxins; toxins produced by fungi such as Streptomycete toxin, plant lectins such as pea lectin, barley lectin or snowdrop lectin; aglutinin; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patain, cystatin, and papain inhibitors; lysine, Examples include ribosome-inactivating proteins (RIPs) such as corn-RIP, abrin, rufin, saporin, or briodin; steroid metabolic enzymes such as 3-hydroxysteroid xidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, and HMG-COA-reductase; ion channel blockers such as sodium or calcium blockers; juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase, and glucanase.

[0351] Furthermore, it should be understood that in connection with the present invention, there exist δ-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or plant insecticidal proteins (Vip), such as Vip1, Vip2, Vip3, or Vip3A, as well as explicitly hybrid toxins, cleavage toxins, and modified toxins. Hybrid toxins are produced by recombination through novel combinations of different domains of these proteins (see, for example, International Publication No. 02 / 15701). For example, cleavage toxins such as cleavage Cry1Ab are known. In the case of modified toxins, one or more amino acids of the natural toxin are substituted. In such amino acid substitutions, preferably, a protease recognition sequence that does not exist naturally is inserted into the toxin. For example, in the case of Cry3A055, a cathepsin-G recognition sequence is inserted into the Cry3A toxin (see International Publication No. 03 / 018810).

[0352] Further examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in European Patent Publication No. 0374753, International Publication No. 93 / 07278, International Publication No. 95 / 34656, European Patent Publication No. 0427529, European Patent Publication No. 451878, and International Publication No. 03 / 052073.

[0353] The preparation processes for such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparations are known, for example, from International Publication No. 95 / 34656, European Patent Application Publication No. 0367474, European Patent Application Publication No. 0401979, and International Publication No. 90 / 13651.

[0354] The toxins contained in transgenic plants confer resistance to harmful insects. Such insects may belong to any of the insect taxa, but are typically found among beetles (Coleoptera), diptera (Diptera), and butterflies (Lepidoptera).

[0355] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known, and some are commercially available. Examples of such plants include: YieldGard® (maize variety expressing Cry1Ab toxin); YieldGard Rootworm® (maize variety expressing Cry3Bb1 toxin); YieldGard Plus® (maize variety expressing Cry1Ab and Cry3Bb1 toxins); Starlink® (maize variety expressing Cry9C toxin); Herculex I® (maize variety expressing Cry1Fa2 toxin and the enzyme phosphinothrysin N-acetyltransferase (PAT) for resistance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety expressing Cry1Ac toxin); Bollgard I® (cotton variety expressing Cry1Ac toxin); Bollgard These include II (registered trademark) (cotton varieties expressing Cry1Ac and Cry2Ab toxins); VipCot (registered trademark) (cotton varieties expressing Vip3A and Cry1Ab toxins); NewLeaf (registered trademark) (potato varieties expressing Cry3A toxin); NatureGard (registered trademark), Agrisure (registered trademark) GT Advantage (GA21 glyphosate resistance trait), Agrisure (registered trademark) CB Advantage (Bt11 corn borer (CB) trait), and Protecta (registered trademark).

[0356] Further examples of such transgenic crops are as follows: 1. Bt11 maize, registered under registration number C / FR / 96 / 05 / 10, from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31, 790 St. Sauveur, France. This is a genetically modified maize (Zea mays) conferred resistance to attacks by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of the cleavage-type Cry1Ab toxin. Bt11 maize has also acquired resistance to the herbicide glufosinate ammonium by transgenic expression of the enzyme PAT.

[0357] 2. Bt176 maize, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize (Zea mays) conferred resistance to attacks by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of the cleavage-type Cry1Ab toxin. Bt176 maize has also acquired resistance to the herbicide glufosinate ammonium by transgenic expression of the enzyme PAT.

[0358] 3. Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, MIR604 maize, registration number C / FR / 96 / 05 / 10. Maize conferred insect resistance by transgenic expression of modified Cry3A toxin. This toxin is Cry3A055, modified by insertion of a cathepsin-G protease recognition sequence. The preparation of such transgenic maize plants is described in International Publication No. 03 / 018810.

[0359] 4. Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. MON 863 maize, registration number C / DE / 02 / 9. MON 863 expresses the Cry3Bb1 toxin and is resistant to certain Coleoptera insects.

[0360] 5. Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium-made IPC 531 cotton, registration number C / ES / 96 / 02.

[0361] 6. 1507 maize, registration number C / NL / 00 / 10, manufactured by Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium. Genetically modified maize to express the protein Cry1F to achieve resistance to certain lepidopteran insects and the PAT protein to achieve resistance to the herbicide glufosinate ammonium.

[0362] 7. Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. NK603×MON810 corn, registration number C / GB / 02 / M3 / 03. This is a conventional hybrid corn variety created by crossing the genetically modified varieties NK603 and MON 810. NK603×MON 810 corn transgenically expresses the CP4 EPSPS protein, derived from the Agrobacterium sp. strain CP4, which confers resistance to Roundup® (glyphosate-containing) herbicide, as well as the Cry1Ab toxin, derived from Bacillus thuringiensis subsp. kurstaki, which confers resistance to certain lepidopteran insects such as the European corn borer.

[0363] As used herein, the term “habitat” means a field where plants are growing, or where the seeds of a cultivated plant have been sown, or where the seeds will be sown in the soil. This includes the soil, seeds and seedlings, and established vegetation.

[0364] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves, and fruits.

[0365] The term “plant propagation material” is understood to refer to the reproductive parts of a plant, such as seeds, and its vegetative parts, such as cuttings or tubers, which can be used for propagation, such as potatoes. Examples include seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, and parts of the plant body. Germinated plants and seedlings that will be transplanted after germination or after emerging from the soil may also be included. These seedlings can be protected by complete or partial immersion treatment before transplanting. Preferably, “plant propagation material” is understood to refer to seeds.

[0366] Pest control agents referred to herein by their common names are publicly known, for example, from “The Pesticide Manual”, 19th Ed., British Crop Protection Council 2021.

[0367] The compounds of formula (I) as defined in the present invention may be used in their original form or, preferably, in combination with auxiliaries conventionally used in the art of formulation. For this purpose, they may be appropriately incorporated in known forms into emulsifiable concentrates, coating pastes, ready-to-spray or dilutable solutions or suspensions, diluted emulsions, wettable powders, soluble powders, powders, granules, as well as encapsulations in polymeric substances. As with the types of compositions, methods of application such as spraying, misting, powdering, granulation, coating, or pouring are selected according to the intended purpose and general circumstances. The compositions 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.

[0368] Suitable carriers and / or auxiliary materials, for example, carriers and auxiliary materials for agricultural use, may be solids or liquids and are substances useful in compounding techniques, such as natural or recycled inorganic substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders, or fertilizers. Such carriers are described, for example, in International Publication No. 97 / 33890.

[0369] 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, as well as defoaming agents and crystal growth inhibitors to enhance activity. When used, these concentrates are diluted in water and typically applied as a spray to the area to be treated. The amount of the active ingredient may range from 0.5% to 95% of the concentrate.

[0370] 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.

[0371] Emulsifying concentrates are homogeneous liquid compositions that are dispersible in water or other liquids and may consist solely of an active compound and a liquid or solid emulsifier, or they may also contain liquid carriers such as xylene, high-boiling aromatic naphtha, isophorone, and other non-volatile organic solvents. When used, these concentrates are dispersed in water or other liquids and typically applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.

[0372] Granular formulations include both extruded materials and relatively coarse particles and are typically applied undiluted to the area requiring treatment. Typical carriers for granular formulations include sand, fuller's soil, attapulgite clay, bentonite clay, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, gypsum, wood flour, crushed corn cobs, crushed peanut shells, sugars, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate, and other organic or inorganic materials that can absorb or be coated with the active compound. Granular formulations typically contain 5% to 25% active ingredients, which may include surfactants such as high-boiling aromatic naphtha, kerosene, and other petroleum fractions or vegetable oils; and / or adhesives such as dextrin, glue, or synthetic resins.

[0373] The powder is a fluid mixture of the active ingredient and finely ground solids such as talc, clay, powder, and other organic and inorganic solids that act as a dispersant and carrier.

[0374] Microcapsules are typically droplets or granules of an active ingredient encapsulated in an inert, porous shell that allows the encapsulated material to be released 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 contain 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 pores of the granules. 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 are naturally occurring. Examples of such materials include vermiculite, calcined clay, kaolin, attapulgite clay, sawdust, and granular carbon. The shell or membrane material includes natural and synthetic rubber, cellulosic materials, styrene-butadiene copolymers, polyacrylonitrile, polyacrylates, polyesters, polyamides, polyureas, polyurethanes, and starch xanthetes.

[0375] Other useful formulations for agricultural chemical applications include simple solutions of the active ingredient in a solvent that completely dissolves it 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 powdered form as a result of evaporation of a low-boiling point dispersant solvent carrier.

[0376] Suitable agricultural additives and / or carriers useful for formulating the above-described composition of the present invention are well known to those skilled in the art.

[0377] 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, α-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, Octadecane Examples include acids, 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 alcohols, tetrahydrofurfuryl alcohol, hexanol, octanol and other high molecular weight alcohols, ethylene glycol, propylene glycol, glycerin and N-methyl-2-pyrrolidinone. Water is generally the optimal carrier for diluting concentrates.

[0378] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselgool, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, fuller's earth, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, walnut husk powder, and lignin.

[0379] 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 weight of the formulation. They can be anionic, cationic, nonionic, or polymeric and can be used as emulsifiers, wetting agents, suspending agents, or for other purposes. Typical surfactants include alkyl sulfates such as diethanolammonium lauryl sulfate; alkylaryl sulfonates, e.g., calcium dodecylbenzenesulfonate; and alkylphenol-alkylene oxide addition products, e.g., nonylphenol-C 18 Alkylphenol-alkylene oxide adducts such as ethoxylates; tridecyl alcohol-C 16 Examples include alcohol-alkylene oxide adducts such as ethoxylates; soaps such as sodium stearate; alkylnaphthalene sulfonates such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinates such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters such as sorbitol oleate; quaternary amines such as lauryltrimethylammonium chloride; polyethylene glycol esters of fatty acids such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono and dialkyl phosphate esters.

[0380] 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.

[0381] 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, either simultaneously with or sequentially with the composition of the present invention. When applied simultaneously, these further active ingredients may be compounded together with the composition of the present invention or mixed, for example, in a spray tank. These further biocides may be fungicides, herbicides, insecticides, fungicides, acaricides, nematicides, plant growth regulators, and / or biological formulations.

[0382] The following combinations of a compound of formula I and another active substance in a 1:1 weight ratio are preferred (where the abbreviation "TX" means "one compound selected from the compounds defined in Tables 1.1-1.100, 2.1-2.50, and Table A"): (7E,9Z)-Dodeca-7,9-diene-1-ylacetate+TX, (9Z,11E)-Tetradeca-9,11-diene-1-ylacetate+TX, (9Z,12E)-Tetradeca-9,12-diene-1-ylacetate+TX, (E)-6-methylhepta-2-en-4-ol+TX, (E)-Deca-5-en-1-ylacetate and (E)-Deca-5-en-1-ol+TX, (E)-Trideca-4-en-1-ylacetate+TX, (E,Z)-Tetradeca-4,10-diene-1 -Illacetate+TX, (Z)-Dodeca-7-En-1-Illacetate+TX, (Z)-Hexadeca-11-En-1-Illacetate+TX, (Z)-Hexadeca-11-Enal+TX, (Z)-Hexadeca-13-En-11-In-1-Illacetate+TX, (Z)-Icosa-13-En-10-On+TX, (Z)-Tetradeca-7-En-1-R+TX, (Z)-Tetradeca-9-En-1-All+TX, (Z)-Tetradeca-9-En-1-Illacetate+TX, 1,2-J Bromo-3-chloropropane + TX, 1,2-dichloropropane + TX, 1,2-dichloropropane and 1,3-dichloropropene + TX, 1,3-dichloropropene + TX, 14-methyloctadeca-1-ene + TX, 1-hydroxy-1H-pyridine-2-thione + TX, 2-(octylthio)ethanol + TX, 2-chlorophenyl N-methylcarbamate (CPMC) + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxy Sid + 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, acinonapyr + TX, Adoxophyes orana GV + TX, afidopiropene + TX, afoxolaner + TX, Agrobacterium radiobacterRadiobacter)+TX, AKD-3088+TX, Aranicarb+TX, Aldicarb+TX, Aldoxycarb+TX, Allethrin+TX, α-Cypermethrin+TX, α-Methrin+TX, α-Multistriatin+TX, Amblyseius spp. species+TX, Amidoflumet+TX, Amino Acids+TX, Aminocarb+TX, Anagrapha falcifera NPV+TX, Anagrus atomus+TX, Aphelinus abdominalis+TX, Aphidius colemani+TX, Aphidoletefs aphidimyza+TX, Apholate+TX, Autographa californica NPV+TX, AZ 60541+TX, Azadirachtin+TX, Azocyclotin+TX, Bacillus aizawai+TX, Bacillus chitinosporus AQ746 (NRRL acceptance number B-21 618)+TX, Bacillus firmus+TX, Bacillus kurstaki+TX, Bacillus mycoides AQ726 (NRRL acceptance number B-21664)+TX, Bacillus pumilus (NRRL acceptance number B-30087)+TX, Bacillus pumilus AQ717 (NRRL acceptance number B-21662)+TX, Bacillus genus sp.)AQ175 (ATCC acceptance number 55608) + TX, Bacillus sp. AQ177 (ATCC acceptance number 55609) + TX, Bacillus sp. AQ178 (ATCC acceptance number 53522) + TX, Bacillus sphaericus Neide + TX, Bacillus subtilis AQ153 (ATCC acceptance number 55614) + TX, BacillusBacillus subtilis AQ30002 (NRRL acceptance number B-50421) + TX, Bacillus subtilis AQ30004 (NRRL acceptance number B-50455) + TX, Bacillus subtilis AQ713 (NRRL acceptance number B-21661) + TX, Bacillus subtilis AQ743 (NRRL acceptance number B-21665) + TX, Unspecified Bacillus subtilis + TX, Bacillus thuringiensis AQ52 (NRRL acceptance number B-21619) + TX, Bacillus thuringiensis BD#32 (NRRL acceptance number B-21530) + TX, Bacillus thuringiensis 'Berliner' Bacillus thuringiensis Berliner)+TX, Bacillus thuringiensis subsp. aizawai+TX, Bacillus thuringiensis subsp. israelensis+TX, Bacillus thuringiensis subsp. japonensis+TX, Bacillus thuringiensis subsp. kurstaki+TX, Bacillus thuringiensis subsp. tenebrionis+TX, Bacillus thuringiensis subspec. kurstaki BMP 123+TX, Beauveria basiana bassiana) + TX, Beauveria blongniartiibrongniartii)+TX, bencrotiaz+TX, benomyl+TX, bensultap+TX, benzoximate+TX, benzpyrimoxane+TX, β-cyfluthrin+TX, β-cypermethrin+TX, bethoxazine+TX, bifenazate+TX, bifenthrin+TX, binapacril+TX, biorethrin+TX, biorethmetrin+TX, bis(tributyltin)oxide+TX, bisadil+TX, bistriflurone+TX, bisulfurfen+TX, Brevicomin+TX, Brofuranilide+TX, Broflutrinate+TX, Bromoacetamide+TX, Bromophos-ethyl+TX, Bronopol+TX, Busulfan+TX, Butocarboxim+TX, Butopyronoxyl+TX, Butoxy(polypropylene glycol)+TX, Butylpyridaben+TX, Kazsaphos+TX, Calcium arsenate+TX, Carbaryl+TX, Carbofuran+TX, Carbon disulfide+TX, Carbosulfan+TX, Cartape+TX, CAS number: 1594624-87-9+TX, CAS number:1922957-47-8+TX, CAS number: 1255091-74-7+TX, CAS number: 1365070-72-9+TX, CAS number: 1445683-71-5+TX, CAS number: 1445684 -82-1+TX, CAS number:1594626-19-3+TX, CAS number:1594637-65-6+TX, CAS number:1632218-00-8+TX, CAS number:1808115-49-2+T X, CAS number: 1922957-46-7+TX, CAS number: 1922957-48-9+TX, CAS number: 1956329-03-5+TX, CAS number: 1990457-52-7+TX, CAS number :1990457-55-0+TX, CAS number:1990457-57-2+TX, CAS number:1990457-66-3+TX, CAS number:1990457-77-6+TX, CAS number:199045 7-85-6+TX, CAS number:2032403-97-5+TX, CAS number:2044701-44-0+TX, CAS number:2095470-94-1+TX, CAS number:2128706-04-5+ TX, CAS number:2128706-05-6+TX, CAS number:2133042-31-4+TX, CAS number:2133042-44-9+TX, CAS number:2171099-09-3+TX, CAS number Product code: 2220132-55-6+TX, CAS number: 2396747-83-2+TX, CAS number: 2408220-91-5+TX, CAS number: 2408220-94-8+TX, CAS number: 2415706-16-8+TX, Piperfuranilide (CAS number: 2615135-05-0)+TX, CAS number: 2719848-60-7+TX, CAS number: RNA (Colorado leaf beetle (Leptinotarsa ​​decemLineata) specific recombinant double-strand interference GS2)+TX, Chlorantraniliprole+TX, Chlordan+TX, Chlorfenapyr+TX, Chloropicrin+TX, Chloroprallethrin+TX, Chlorpyrifos+TX, Chromafenozide+TX, Yamato lacewing (Chrysoperla)Carnea) + TX, Clempyrin + TX, Chloetocarb + TX, Clothianidin + TX, Chodrelua + TX, Codlememon + TX, Copper acetoarsenite + TX, Copper dioctanoate + TX, Copper hydroxide + TX, Copper sulfate + TX, Cresol + TX, Culfomate + TX, Cryptolaemus montrouzieri + TX, Cryptolaemus + TX, Cyanophenphos + TX, Cyantraniliprole + TX, Sibutrin + TX, Cyclaniliprole + TX, Cyclobtriflurum + TX, Cycloprotrin + TX, Cycloxapride + TX, Codlinga (Cydia) Pomonella GV+TX, cyenopyrafen+TX, cyetopyrafen+TX, cyflumetofen+TX, cyfluthrin+TX, cyhalodiamid+TX, cyhalothrin+TX, cypermethrin+TX, cyphenothrin+TX, cyprofuranilide+TX, cyromazine+TX, cytokinin+TX, Dacnusa sibirica+TX, dazomet+TX, DBCP+TX, DCIP+TX, deltamethrin+TX, diafenthiuron+TX, dialiphos+TX, diamidaphos+TX, dibrom+TX, dibutyl adipate+TX, dibutyl phthalate+TX, dibutyl succinate+TX, Diclofenthion + TX, Diclofen + TX, Diclofen + TX, Dicliphos + TX, Dichloromezothiaz + TX, Diethyltoluamide + TX, Diflubenzuron + TX, Diglyphus (Isaea dwarf wasp) isaea)+TX, dimatif+TX, dimethoate+TX, dimethylcalvert+TX, dimethyl phthalate+TX, dimepropyridaz+TX, dinactin+TX, dinocap+TX, dinotefuran+TX, dioxabenzophos+TX, dipirithione+TX, disparla+TX, D-limonene+TX, dodeca-8-en-1-ylacetate+TX, dodeca-9-en-1-ylacetate+TX, dodeca-8,10-dien-1-ylacetate+TX, dodicine+TX, dominicalla+TX, doramectin+TX, emamectin+TX, emamectin benzoate+TX, empenthrin+TX, Encarsia formosa)+TX, endotal+TX, endrin+TX, eprinomectin+TX, ε-monfluorothrin+TX, ε-metofluthrin+TX, desert gall wasp (Eretmocerus eremicus)+TX, esfenvalerate+TX, ethion+TX, ethiprole+TX, etoprophos+TX, 4-methyloctanoate ethyl+TX, ethylhexanediol+TX, dibromylene+TX, etofenprox+TX, etoxazole+TX, etopyrafen+TX, eugenol+TX, seaweed extract and fermented products derived from melasse+TX, seaweed extract and fermented products derived from melasse containing urea+TX, seaweed extract and fermented plant products+TX, seaweed extract and fermented plant products containing plant hormones, vitamins, EDTA chelated copper, zinc, and iron+TX, f Fanfar+TX, Phenaminosulf+TX, Phenamiphos+TX, Phenazaquin+TX, Fenfluthrin+TX, Fenitrothion+TX, Fenmezoditiaz+TX, Phenobucarb+TX, Phenothiocarb+TX, Phenoxycarb+TX, Fenpropathrin+TX, Fenpyrad+TX, Fenpyroximate+TX, Fensulfothion+TX, Fenthion+TX, Fentin+TX, Triphenyltin acetate+TX, Fenvalerate+TX, Ferric phosphate+TX, Fipronil+TX, Flomethoquin+TX, Flonicamide+TX, Fluacrypyrim+TX,Fluazanididine + 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, Flupyrimine + TX, Flupyroxystrobin + TX, Flularaner + TX, Fluvalinate + TX, Fluxamethamide + TX, Formaldehyde Do+TX, Fostiazate+TX, Fostiethane+TX, Frontalin+TX, Furfural+TX, γ-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 Heliothis punctigera (Nuclear Polyhedrosis Virus) + TX, Helicoverpa zea (Nuclear Polyhedrosis Virus) + TX, Helicoverpa zea (Nuclear Polyhedrosis Virus) + TX, Heliothis punctigera (Nuclear Polyhedrosis Virus) + TX, Heliothis virescens (Nuclear Polyhedrosis Virus) + TX, Hemel + TX, Hempa + TX, Heptafluthrin + TX, Heterophos + TX, Heterorhabditis bacteriophora and H. megidis + TX, Hexarua + TX, Hexaamide + TX, Hexithiazox + TX, Hippodamia (concentrates) + TX, hydramethylnon + TX, hydralgafen + TX, slaked lime + TX, imiciaphos + TX, imidacloprid + TX, imiprothrin + TX,Indazapiroxameth + TX, Indoxacarb + TX, Iodomethane + TX, Iprodione + TX, Ipsdienol + TX, Ipsenol + TX, Isamidophos + TX, Isazofos + TX, Isocycloseram + TX, Isoflualanum (CAS number: 2892524-05-7) + TX, Isothioate + TX, Ivermectin + TX, Japonilua + TX, κ-Bifenthrin + TX, κ-Tefluthrin + TX, Kasugamycin + TX, Kasugamycin hydrochloride hydrate + TX, Kinetin + TX, λ-Cyhalotorin + TX, Redoprona + TX, Lepimectin + TX, Leptomastix dactylopii)+TX, lineatin+TX, liturua+TX, lupurua+TX, rotillaner+TX, lufenuron+TX, Macrolophus caliginosus+TX, Mamestra brassicae NPV+TX, mecarphone+TX, medolua+TX, megatomoic acid+TX, metaflumizone+TX, metaldehyde+TX, metam+TX, metam-potassium+TX, metam-sodium+TX, Metaphycus helvolus+TX, Metarhizium anisopliae var. acridum+TX, Metarhizium anisopliae var. anisopliae+TX, Metarhizium genus spp.)+TX, Metepa+TX, Methiocarb+TX, Methiotepa+TX, Methomyl+TX, Methquin-butyl+TX, Methoxyphenozide+TX, Methylaphorate+TX, Methylbromide+TX, Methyleugenol+TX, Methylisothiocyanate+TX, Methylneodecanamide+TX, Metofluthrin+TX, Metolcarb+TX, Mexacalbate+TX, Milbemectin+TX, Milbemycin oxime+TX, Monfluorothrin+TX, Morzide+TX, Moxidectin+TX, Muscarua+TX, Muscodor albus 620 (NRRL acceptance number 30547)+TX,Muscodor roseus A3-5 (NRRL acceptance number 30548) + TX, Mulberry dark spot disease fungus (Myrothecium verrucaria) composition + TX, Naabam + TX, NC-184 + TX, Neem tree-derived product + TX, Pine sawfly (Neodiprion) N. 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-diene-1-ylacetate + TX, Octadeca-3,13-diene-1-ylacetate + TX, Octylinone + TX, Omethoate + TX, Orflurua + TX, Orius spp. + TX, Orictalua + TX, Ostramon + TX, Oxamate + TX, Oxamyl + TX, Oxazosulfyl + TX, Oxolinic acid + TX, Oxytetracycline + TX, Paecilomyces humosoroseus fumosoroseus)+TX, Paecilomyces lilacinus+TX, parathion-ethyl+TX, Pasteuria nishizawae+TX, Pasteuria penetrans+TX, Pasteuria ramosa+TX, Pasteuria thornei+TX, Pasteuria usgae+TX, P-cymene+TX, penfluron+TX, pentachlorophenol+TX, permethrin+TX, phenothrin+TX, phorate+TX, phosphamidone+TX, phosphocarb+TX, Chilean predatory mite (Phytoseiulus) persimilis)+TX, picaridin+TX, bioxaniliprol+TX, piperazine+TX, piperonyl butoxide+TX, pyrimicarb+TX, pyrimiphos-ethyl+TX, pyrimiphos-methyl+TX, diamondback moth (Plutella xylostella) granulosis virus+TX,Plutella xylostella nuclear polyhedrosis virus + TX, polyhedrosis virus + TX, potassium and molybdenum and EDTA-chelated manganese + TX, potassium ethylxanthogenic acid + TX, potassium hydroxyquinoline sulfate + TX, prallethrin + TX, probenazole + TX, profenofos + TX, profluthrin + TX, Propargit + TX, Propetamphos + TX, Propoxar + TX, Prothiophos + TX, Protrefen Bute + TX, Piflubmid + TX, Pymetrozine + TX, Pyraclopos + TX, Pyrafluprole + TX, Pyridaben + TX, Pyridaryl + TX, Pyridine-4-amine + TX, Pyrifluquinazone + TX, Pyrimidifen + TX, Pyriminostrobin + TX, Pyriprole [394730-71-3] + TX, Pyriprole + TX, Pyriproxyfen + TX, QRD 420 (Terpenoid Blend) + TX, QRD 452 (Terpenoid Blend) + TX, QRD 460 (Terpenoid Blend) + TX, Soap Tree (Quillaja saponaria) + TX, Quinoclamine + TX, Quinonamide + TX, Resmethrin + TX, Rhodococcus globulus globerulus)AQ719 (NRRL acceptance number B-21663)+TX, sarolaner+TX, S-biorethrin+TX, cebuphos+TX, selamectin+TX, sigrua+TX, silafluofen+TX, simazine+TX, sodium pentachlorophenoxide+TX, sordidine+TX, spidoxamato+TX, spinetoram+TX, spinosad+TX, spirobudifen+TX, spirodiclofen+TX, spiromesifen+TX, spiropidione+TX, spirotetramato+TX, Spodoptera exigua polycapsidone polyhedrosis virus+TX, Spodoptera frugiperda polyhedrosis virus+TX, Steinernema viviones bibionis)+TX, Steinernema carpocapsae+TX, Steinernema feltiae+TX, Steinernema glaseri+TX, Steinernema riobrave+TX, Steinernema riobravis+TX, Steinernema scapterisci+TX, Steinernema spp.)+TX, Streptomyces galbus (NRRL acceptance number 30232)+TX, Streptomyces genus sp.) (NRRL acceptance number B-30145) + TX, streptomycin + TX, streptomycin sesquisulfate + TX, strychnine + TX, sulcatol + TX, sulfiflumin (CAS number: 2377084-09-6) + TX, sulfoxaflor + TX, tadimucarb + TX, tebufenozide + TX, tebufenpyrad + TX, tebupirimiphos + TX, tecrophthalam + TX, tefluthrin + TX, temephos + TX, tepa + TX, terbam + TX, terbuphos + TX, terpenoid blend + TX, tetrachlorantraniliprole + TX, tetrachlorothiophene + TX, tetradeca-11-en-1-yl acetate + TX, tetradiphon + TX, tetramethrin + TX, tetramethylfluthrin + TX, tetranactin + TX, tetranilip Roll + TX, θ-cypermethrin + TX, thiacloprid + TX, thiaphenox + TX, thiamethoxam + TX, thiocyclam + TX, thiodicarb + TX, thiophanox + TX, thiohempa + TX, thiomelsar + TX, thiometon + TX, thionazine + 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, 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, Trunkcol+TX, Cyclopyrazoflor+TX, Typhlodromus occidentalis+TX, Uredepa+TX, Verticillium lecanii+TX, Verticillium spp.+TX, Xylenol+TX, YI-5302+TX, Zeatin+TX, ζ-Cypermethrin+TX;. N-[(1R)-1-benzyl-3-chloro-1-methylbuta-3-enyl]-8-fluoroquinoline-3-carboxamide+TX, N-[(1S)-1-benzyl-3-chloro-1-methylbuta-3-enyl]-8-fluoroquinoline-3-carboxamide+TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine (these compounds (These compounds may be prepared by the method described in International Publication No. 2019 / 110427) + TX, (3',4',5'-trifluorobiphenyl-2-yl)-amide + TX, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone (These compounds may be prepared by the method described in International Publication No. 2017 / 220485) + TX, (4-phenoxyphenyl) Tyl 2-amino-6-methylpyridine-3-carboxylate (this compound can be prepared by the method described in International Publication No. 2014 / 006945) + TX, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone + TX, (7E,9Z)-dodeca-7,9-diene-1-ylacetate + TX, (9Z,11E)-tetradeca-9,11-diene-1-ylacetate TX, (9Z,12E)-tetradeca-9,12-diene-1-ylacetate + TX, (E)-6-methylhepta-2-en-4-ol + TX, (E)-deca-5-en-1-ylacetate and (E)-deca-5-en-1-ol + TX, (E)-trideca-4-en-1-ylacetate + TX, (E,Z)-tetradeca-4,10-diene-1-ylacetate, + TX, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, (Z)-dodeca-7-en-1-ylacetate + TX, (Z)-hexadeca-11-en-1-ylacetate + TX, (Z)-hexadeca-11-enal + TX, (Z)-hexadeca-13-en-11-in-1-ylacetate + TX, (Z)-icosa-13-en-10-one + TX, (Z)-tetradeca-7-en-1-al + TX, (Z)-tetradeca-9-en-1-ol + TX, (Z)-tetradeca-9-en-1-ylacetate + TX, (Z (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazole-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide (this compound can be prepared by the method described in International Publication No. 2018 / 153707) + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazole-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide + TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazole-1-yl]acetyl]-4-piperidyl]thiazole [-4-yl]-4,5-dihydroisoxazole-5-yl]-3-chlorophenyl]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 by the method described in International Publication No. 2017 / 025510) + TX, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane + TX, 1,2-dibromo-3-chloropropane + TX, 1,2-Dichloropropane and 1,3-Dichloropropene + TX, 1,3-Dichloropropene + TX, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]urea + TX, 1-[2-[[1-(4-chlorophenyl)pyrazole-3-yl]oxymethyl]-3-methylphenyl]-4-methyltetrazol-5-one + TX, 10-diene-1-yl acetate + TX, 14-methyloctadeca-1-ene + TX, 1-bromo-2-chloroethane + TX, 1-dichloro-1-nitroethane + TX, 1-hydroxy-1H-pyridine-2-thione + TX, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea + TX, 1-methyl -4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazole-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(1,3-dithiolan-2-yl)phenyldimethylcarbamate + TX, 2-(2-butoxyethoxy)ethyl Piperonilate + 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)-N-(3-ethyl-1,1-dimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethylindan-4-yl]pyridine-3-carboxamide + TX, 2-(difluoromethyl )-N-[(3S)-3-ethyl-1,1-dimethylindan-4-yl]pyridine-3-carboxamide (this compound can be prepared by the method described in International Publication No. 2014 / 095675) + TX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethylindan-4-yl]pyridine-3-carboxamide + TX, 2-(octylthio)ethanol + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate + TX, 2,2-dichlorovinyl 2-ethylsulfinylethylmethyl phosphate + TX, 2,2-Difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide + TX, 2,4-dichlorophenylbenzenesulfonate + TX, 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetron (this compound can be prepared by the method described in International Publication No. 2011 / 138281) + TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propane 2-2-ol + TX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazole-1-yl)propan-2-ol (This compound may be prepared by the method described in International Publication No. 2017 / 029179) + TX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazole-1-yl)propan-2-ol (This compound may be prepared by the method described in International Publication No. 2017 / 029179) + TX, 2-chlorovinyl Diethyl phosphate + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide + TX, 2-imidazolidone + TX, 2-isovalerylindan-1,3-dione + TX, 2-methyl(propa-2-inyl)aminophenylmethylcarbamate + TX, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide (this compound can be prepared by the method described in International Publication No. 2018 / 065414) + TX, 2-thiocyanatoethyl laurate + TX, 3 -(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole (these compounds can be prepared by the method described in International Publication No. 2016 / 156085) + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinoline-1-yl)quinolone + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 3,4-Dichlorotetrahydrothiophene 1,1-dioxide + TX, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (This compound may be prepared by the method described in International Publication No. 2016 / 156290) + TX, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (This compound may be prepared by the method described in International Publication No. 2016 / 156290) (obtained) + TX, 3-bromo-1-chloropropane + 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-dimethylisoquinoli +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(propane-2-inyl)amino-3,5-xylylmethylcarbamate + TX, 4-methylnonan-5-ol and 4-methylnonanan-5-one + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohexa-2-enone + TX, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole -3-yl]phenyl]methyl]isoxazolidine-3-one + TX, 5,5-dimethyl-3-oxocyclohexa-1-enyldimethylcarbamate + TX, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid + TX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide (International Publication No. 202) (May be prepared by the method described in International Publication No. 0 / 109391) + TX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methylpyridazine-4-carboxamide (May be prepared by the method described in International Publication No. 2020 / 109391) + TX, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazole-1-yl)isoquinoline + TX, 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-Difluoro-ethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide (which can be prepared by the method described in International Publication No. 2020 / 109391) + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile + TX, 6-isopentenylaminopurine + TX, 8-fluoro-N-[(1R)-1-[(3-fluoro [Phenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, 8-hydroxyquinoline sulfate + TX, acetylone + TX, acetoprole + TX, acibenzolar + TX, acibenzolar-S-methyl + TX, acrylonitrile + TX, Adoxophyes orana) GV+TX, Agrobacterium radiobacter+TX, Aldoxycarb+TX, Aldrin+TX, Allosamidin+TX, Alixicarb+TX, α-Chlorohydrin+TX, α-Ecdysone+TX, α-Multistriatin+TX, Aluminum phosphide+TX, Amblyseius 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, Ants + TX, Aphelinus abdominalis + TX, Aphidius colemani + TX, Aphidoletes aphidimyza + TX, Apholate + TX, Aramite + TX, Arsenic trioxide + TX, Atidathion + TX, Autographa californica NPV + TX, Azaconazole + TX, Azamethiphos + TX, Azobenzene + TX, Azothoate + TX, Azoxystrobin + TX, Bacillus sphaericus Neide + TX, Bacillus thuringiensis (Bacillus (thuringiensis) Delta Endotoxin + TX, Barium Carbonate + TX, Barium Hexafluorosilicate + TX, Barium Polysulfide + TX, Bartholin + TX, Bayer 22 / 190 + TX, Bayer 22408 + TX, Beauveria brongniartii + TX, Benalaxyl + TX, Bencrotiaz + TX, Benomyl + TX, Benoxaphos + TX, Bentiavaricarb + TX, Benzothiostrobin + TX, Benzovindiflupir + TX, Benzyl Benzoate + TX, β-Cyfluthrin + TX, β-Cypermethrin + TX, Bethoxazine + TX, Bioetanomethrin + TX, Biopermethrin + TX, Bis(2-chloroethyl) ether + TX, Bis(tributyltin) oxide + TX, Bisadyl + TX, Bisthiosemi + TX, Vitertanol + TX, Biki Safen+TX, Blastocidine-S+TX, Borax+TX, Bordeaux mixture+TX, Boscalid+TX, Brevicomin+TX, Brodifacum+TX, Brofenvalerate+TX, Bromadiolon+TX, Bromethalin+TX, Bromfenbinphos+TX, Bromoacetamide+TX, Bromocyclene+TX, Bromo-DDT+TX, Bromophos+TX, Bromopropylate+TX, Bromuconazole+TX, Bronopol+TX, Bufencarb+TX, Bupirimate+TX, Buprofezin+TX, Busulfan+TX,Buta-3-inyl N-[6-[[(Z)-[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate+TX, Butacarb+TX, Butathiophos+TX, Butocarboxim+TX, Butonate+TX, Butopyronoxyl+TX, Butoxy(polypropylene glycol)+TX, Butoxycarboxim+TX, Butylpyridaben+TX, Calcium arsenate+TX, Calcium cyanide+TX, Calcium polysulfide+TX, Campechlor+TX, Captahol+TX, Captan+TX, Carbanolate+TX, Carbendazim+TX, Carbon disulfide+TX, Carbon tetrachloride+TX, Carbophenothion+TX, Carboxine+TX, Cartap hydrochloride+TX, CAS number: 2132414-04-9+TX, CAS number: 23 44721-61-3+TX, Sebadin+TX, Quinomethionat+TX, Chloralose+TX, Chlorbenside+TX, Chlorbicurene+TX, Chlordan+TX, Chlordecone+TX, Chlordimeform+TX, Chlordimeform hydrochloride+TX, Chlorphenetol+TX, Chlorfensone+TX, Chlorfensulfide+TX, Chlorobenzylate+TX, Chloroform+TX, Chloroinconazide+TX, Chloromebform+TX, Chloromethion+TX, Chloroneb+TX, Chlorophacinone+TX, Chloropicrin+TX, Chloropropylate+TX, Chlorthalonil+TX, Chlorphoxime+TX, Chlorprazophos+TX, Chlorthiophos+TX, Clozolinate+TX, Cholecalciferol+TX, Chrysoperla carnea)+TX, Synerin I+TX, Synerin II+TX, Synerin+TX, cismethrin+TX, cis-resmethrin+TX, crocitrin+TX, closantel+TX, chodrelua+TX, chodremon+TX, copper acetoarsenite+TX, copper arsenate+TX, copper dioctanoate+TX, copper hydroxide+TX, copper naphthenate+TX, copper oleate+TX, copper oxide+TX, copper oxychloride+TX, copper sulfate+TX, coumarol+TX, coumafuryl+TX, coumaphos+TX, coumatetralyl+TX, coumethoxystrobin (jiaxiangjunzhi)+TX, coumitoate+TX, coumoxystrobin+TX, cresol+TX, crimidine+TX,Crotamiton + TX, Clothoxyphos + TX, Culfomate + TX, Cryolite + TX, Ladybug (Cryptolaemus montrouzieri) + TX, CS 708 + TX, Culua + TX, Cufraneb + ​​TX, Cyanophenphos + TX, Cyanophos + TX, Cyanthoate + TX, Cyazofamide + TX, Sibutrin + TX, Cicrethrin + TX, Cyclobtrifluram + TX, Codlinga (Cydia pomonella) GV + TX, Cyflufenamid + TX, Simiazole + TX, Cymoxanil + TX, Cyproconazole + TX, Cyprodinil + TX, Sathioate + TX, Cytokinin + TX, Dacnusa sibirica)+TX, DAEP+TX, dazomet+TX, DCIP+TX, DCPM+TX, DDT+TX, debacarb+TX, decarbofuran+TX, demefion+TX, demefion-O+TX, demefion-S+TX, demeton-methyl+TX, demeton-O+TX, demeton-O-methyl+TX, demeton-S+TX, demeton-S-methyl+TX, demeton-S-methylsulfone+TX, diamidaphos+TX, dibutyl adipate+TX, dibutyl phthalate+TX, dibutyl succinate+TX, dicapton+TX, diclobentiazox+TX, diclofenthion+ TX, Diclofluanide + TX, Diclon + TX, Dichlorofen + TX, Dichlorvos + TX, Diclozoline + TX, Dicliphos + TX, Diclosimet + TX, Diclomedin + TX, Dichloran + TX, Diclesil + TX, Dicyclanil + TX, Dicyclopentadiene + TX, Dierdrin + TX, Dienochlor + TX, Dietofencarb + TX, Diethyl 5-methylpyrazole-3-yl phosphate + TX, Diethyltoluamide + TX, Diphenacome + TX, Difenoconazole + TX, Difethiaron + TX, Diflovidazine + TX, Diglyphus (Isaea dwarf wasp) isaea)+TX, dirol+TX, dimatif+TX, dimefluthrin+TX, dimehox+TX, dimethane+TX, dimethirimol+TX, dimethomorph+TX, dimethrin+TX, dimethylcarbate+TX, dimethyl phthalate+TX, dimethylvinphos+TX, dimethilane+TX, dimoxystrobin+TX, dynex+TX,Dynex-Dicrexin+TX, Diniconazole+TX, Dinocap-4+TX, Dinocap-6+TX, Dinoctone+TX, Dinopenton+TX, Dinoprop+TX, Dinosam+TX, Dinoseb+TX, Dinosulfone+TX, Dinotervon+TX, Diofenolan+TX, Dioxabenzophos+TX, Dioxathion+TX, Difacinone+TX, Diphenylsulfone+TX, Dipimethitron+TX, Dipirithione+TX, Dispa Lua + TX, Disulfiram + TX, Dithianone + TX, Diticlophos + TX, DNOC + TX, Dodeca-8-en-1-ylacetate + TX, Dodeca-9-en-1-ylacetate + TX, Dodeca-8 + TX, Dodemorph + TX, Dodicin + TX, Dozin + TX, Dofenapine + TX, Dominicalua + TX, Doramectin + TX, DSP + TX, d-Tetramethrin + TX, Ecdysterone + TX, Edifenphos + TX, EI 1642 + TX, EMPC + TX, Encarsia formosa + TX, Endotar + TX, Endothion + TX, Enesterobrine + TX, Enoxastrobin + TX, EPBP + TX, Epoxyconazole + TX, Eprinomectin + TX, Eretmocerus eremicus)+TX, ergocalciferol+TX, ethafos+TX, etaboxam+TX, ethiofencarb+TX, etyrimol+TX, ethoate-methyl+TX, ethyl 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoropropa-1-enoxy]phenyl]methyl]pyrazole-3-carboxylate (which can be prepared by the method described in International Publication No. 2020 / 056090)+TX, ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolane -2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate (can be prepared by the method described in International Publication No. 2020 / 056090) + TX, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate + TX, ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate (this compound,(Can be prepared by the method described in International Publication No. 2018 / 158365) + TX, ethyl 4-methyl octanoate + TX, ethyl formate + TX, ethyl hexanediol + TX, ethylene dibromide + TX, ethylene dichloride + TX, ethylene oxide + TX, etridiazole + TX, etrimphos + T, X, Eugenol + TX, EXD + TX, Famoxadone + TX, Farnesol + TX, Farnesol and Nerolidol + TX, Phenamidon + TX, Phenaminosulf + TX, Phenaminestrobin + TX, Phenalimol + TX, Phenazaflor + TX, Fenbuconazole + TX, Fenbutatin oxide + TX, Fenchlorfos + TX, Phenetacarb + TX, Fenflam + TX, Fenhexamide + TX, Fenitrothion + TX, Phenothio Carb+TX, phenoxacrim+TX, phenoxanil+TX, fenpiclonil+TX, fenpicoxamide+TX, fenpyritrin+TX, fenpropidine+TX, fenpropimorph+TX, fenpyrad+TX, fenpyrazamine+TX, fenpyroximate+TX, fenson+TX, fensulfothione+TX, fenthion+TX, fenthion-ethyl+TX, fentin+TX, fentriphanil+TX, Ferbam+TX, Felimzone + TX, Ferric phosphate + TX, Furocumafen + TX, Floryl picoxamide + TX, Fluazinam + TX, Flubeneteram + TX, Flubendimine + TX, Flucoflon + TX, Flucycloxurone + TX, Fludioxonil + TX, Fluenetil + TX, Fluphenoxadiazam + TX, Fluphenoxystrobin + TX, Fluindapyr + TX, Flumethylsulfolimon + TX, Flumorph + TX, Fluopicolide + TX, Fluopimomi Do+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, flutriafole+TX, fluxapiroxad+TX, FMC 1137+TX, Holpet+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,γ-HCH+TX, Gliodin+TX, Grandlure+TX, Grandlure I+TX, Grandlure II+TX, Grandlure III+TX, Grandlure IV+TX, Guazatine+TX, Guazatine acetate+TX, Halfenprox+TX, HCH+TX, Hemel+TX, Hempa+TX, HEOD+TX, Heptachlor+TX, Heterophos+TX, Heterorhabditis bacteriophora and H. megidis+TX, Hexaconazole+TX, Hexadecylcyclopropanecarboxylate+TX, Hexarua+TX, Hexaamide+TX, HHDN+TX, Hippodamia (concentrates) + TX, hydralgafen + TX, slaked lime + TX, hydrogen cyanide + TX, himexazole + TX, hikincarb + TX, imanin + TX, imazalil + TX, imibenconazole + TX, iminoctadine + TX, impflufluxam + TX, ipconazole + TX, ipfentrifluconazole + TX, ipflufenoquin + TX, iprobenphos + TX, iprodione + TX, iprovalicarb + TX, ipsdienol + TX, ipsenol + TX, IPSP + TX, isamidophos + TX, isazofos + TX, isobenzan + TX, isocarbophos + TX, isodrine + TX, Isophenphos + TX, Isofetamide + TX, Isoflucipram + TX, Isolan + TX, Isoprothiolan + TX, Isopyrazam + TX, Isothianil + TX, Isoxathion + TX, 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)+TX, leptophos+TX, lindan+TX, lineatin+TX, lilimphos+TX, litorua+TX, lupulua+TX, rubenmixianan+TX, lithidathione+TX,Macrolophus caliginosus + TX, Magnesium phosphide + TX, Malonoben + TX, Mamestra brassicae NPV + TX, Mankapper + TX, Mancozeb + TX, Mandestrobin + TX, Mandipropamide + TX, Maneb + ​​TX, Magidox + TX, m-Cumenyl methylcarbamate + TX, Mecarbam + TX, Mecarfon + TX, Medrua + TX, Mefentrifluconazole + TX, Megatomoic acid + TX, Menazone + TX, Mepanipyrim + TX, Meperfluthrin + TX, Mephosphoran + TX, Mepronil + TX, Mercuric oxide + TX, Mercurous chloride + TX, Mesulfen + TX, Mesulfenphos + TX, Metalaxyl + TX, Metam + TX, Metam-potassium + TX, Metam-sodium + TX, Metaphycus herborus helvolus)+TX, Metarhizium anisopliae var. acridum+TX, Metarhizium anisopliae var. anisopliae+TX, metallyl picoxamide+TX, metconazole+TX, metepa+TX, methacryphos+TX, methanesulfonyl fluoride+TX, metasulfocarb+TX, methiotepa+TX, metoclotophos+TX, methoprene+TX, metoquin-butyl+TX, methotrin+TX, methoxychlor+TX, methyl(Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxypropa-2-enoate+TX, methyl(Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxypropa-2 -Enoates (These compounds can be prepared by the method described in International Publication No. 2020 / 193387) + TX, Methyl(Z)-2-[5-(3-isopropylpyrazole-1-yl)-2-methylphenoxy]-3-methoxypropa-2-enoate + TX, Methyl(Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazole-1-yl)phenoxy]propa-2-enoate + TX, Methyl(Z)-3-methoxy-2-[2-methyl-5-(4-propyltriazole-2-yl)phenoxy]propa-2-enoate + TX,Methyl(Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazole-1-yl]phenoxy]propa-2-enoate (These compounds can be prepared by the method described in International Publication No. 2020 / 079111) + TX, Methyl(Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazole-2-yl]phenoxy]propa-2-enoate + TX, Methyl aphorate + TX, Methyl bromide + TX, Methyl eugenol + TX, Methyl isothiocyanate + TX, Methyl N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazole-4-yl]-2-methylphenyl]methyl]carbamate (International Publication No. 2 (May be prepared by the method described in International Publication No. 020 / 097012) + TX, Methyl N-[[4-[1-(4-cyclopropyl-2,6-difluorophenyl)pyrazole-4-yl]-2-methylphenyl]methyl]carbamate (May be prepared by 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, Methyl chloroform + TX, Methylene chloride + TX, Methyl neodecanamide + TX, Methylram + TX, Methylcarb + TX, Metminostrobin + TX, Methoxadiazone + TX, Metraphenone + TX, Methyltetraprole + TX, MGK 264+TX, Milbemycin oxime+TX, Mipahox+TX, Mirex+TX, Monoclotophos+TX, Morphothion+TX, Morzide+TX, Moxidectin+TX, Muscarua+TX, Mycrobutanil+TX, Microzolin+TX, Mulberry dark spot disease fungus (Myrothecium verrucaria) composition+TX, N-((1R)-1-benzyl-3-chloro-1-methylbuta-3-enyl)-8-fluoroquinoline-3-carboxamide (these compounds can be prepared by the method described in International Publication No. 2017 / 153380)+TX, N-((1S)-1-benzyl-3-chloro-1-methylbuta-3-enyl)-8-fluoroquinoline-3-carboxamide (these compounds can be prepared by the method described in International Publication No. 2017 / 153380)+TX,N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine + TX, N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine + TX, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide + TX, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-1,2,4- Riazole-3-amine (These compounds can be prepared by the methods described in International Publication Nos. 2017 / 055473, 2017 / 055469, 2017 / 093348 and 2017 / 118689) + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-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-methylphenyl]-N-ethyl-N-methylformamidine (this compound may be prepared by the method described in International Publication No. 2016 / 202742) + TX, N'-[4-(4,5-dichlorothiazole-2-yl)oxy-2,5-dimethylphenyl]-N -Ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine (These compounds can be prepared by the method described in International Publication No. 2015 / 155075) + TX, N'-[5-bromo-2-methyl -6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared by the method described in IPCOM000249876D) + TX, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N- Methyl-formamidine + TX, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N-[N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide (These compounds can be prepared by the method described in International Publication No. 2018 / 202428) + TX, N'-[4-(1-cyclopropyl-2,2,2-Trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methylphenyl]-N-isopropyl-N-methyl-formamidine (These compounds can be prepared by the method described in International Publication No. 2018 / 228896) + TX, Narbam + TX, Naphthalophos + TX, Nared + TX, Naphthalene + TX, NC-170 + TX, Pine sawfly (Neodiprion) N. sertifer) NPV and N. lecontei NPV + TX, nerolidol + TX, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide + TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetane-2-yl]phenyl]-N-methyl-formamidine + TX, nickel bis(dimethyldithiocarbamate) + TX, niclosamide-olamine + TX, nicotine + TX, nicotine sulfate + TX, niflulidide + TX, nicomycin + TX, N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl- Lumuamidine + 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-Diene-1-yl acetate + TX, Octylinone + TX, Oflace + TX, Oleic acid + TX, Omethoate + TX, Orflurua + TX, Orius spp. + TX, Orictalua + TX, Oryzastrobin + TX, Ostramon + TX, Oxadixyl + TX, Oxamate + TX, Oxatiapiproline + TX, Oxolinic acid + TX, Oxocarboxyne + TX, Oxideprophos + TX, Oxydisulfon + TX, Oxytetracycline + TX, Paclobutrazol + TX, Paecilomyces fumosoroseus (Phytoseiulus)+TX, para-dichlorobenzene+TX, parathion+TX, parathion-methyl+TX, pefurazoate+TX, penconazole+TX, pencyclon+TX, penflufen+TX, penflulon+TX, pentachlorophenol+TX, pentachlorophenyl laurate+TX, penthiopyrad+TX, permethrin+TX, PH 60-38+TX, phenamacryl+TX, fencapton+TX, fosacetim+TX, fosalon+TX, phosdiphen+TX, phospholan+TX, phosglycine+TX, fosnicrol+TX, phosphamidone+TX, phosphine+TX, phosphorus+TX, phoxim-methyl+TX, phthalide+TX, Chilean predatory mite (Phytoseiulus)persimilis)+TX, picarbtrazox+TX, picaridin+TX, picoxystrobin+TX, pindone+TX, piperazine+TX, piperonyl butoxide+TX, piprotal+TX, pyrimetaphos+TX, polychlorodicyclopentadiene isomer+TX, polychloroterpene+TX, polynactin+TX, polyoxin+TX, potassium arsenite+TX, potassium ethylxanthogenicate+TX, potassium hydroxyquinoline sulfate+TX, potassium thiocyanate Um+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, Propoxar+TX, Propropyl isomer+TX, Proquinazide+TX, Protidathion+TX, Prothioconazole Lu+TX, Prothiophos+TX, Protoate+TX, Pidiflumetofen+TX, Pyraclostrobin+TX, Pyramethrostrobin+TX, Pyraoxystrobin+TX, Pyrapropoin+TX, Pyraziflumid+TX, Pyrazophos+TX, Pyrethmetrin+TX, Pyrethrin I+TX, Pyrethrin II+TX, Pyrethrin+TX, Pyribencarb+TX, Pyridaclomethyl+TX, Pyridafenthion+TX, Pyridine-4-amine+TX, Pyriphenox+TX, Pyri Methanil + TX, Pyrimitate + TX, Pyrimorph + TX, Pyrinulone + TX, Pyriophenone + TX, Pyrisoxazole + TX, Pyrroquilon + TX, Quassia + TX, Quinalphos + TX, Quinalphos-methyl + TX, Quinoclamine + TX, Quinofumeline + TX, Quinonamide + TX, Quinotion + TX, Quinoxyfen + TX, Quinthiokiss + TX, Quintozene + TX, R-1492 + TX, Rahoxanide + TX, Resmethrin + TX, Japanese knotweed (Reynoutria japonica)Sachalinensis extract + TX, Ribavirin + TX, Metalaxyl (Rmetalaxyl) + TX, Rotenone + TX, Lianya + TX, Lianodine + TX, S421 + TX, Sabajira + TX, Shuladan + TX, Siriloside + TX, Seboctilamine + TX, Cebuphos + TX, Sedaxane + TX, Selamectin + TX, Sesamex + TX, Sesamolin + TX, SI-0009 + TX, Siglua + TX, Simazine + TX, Simeconazole + TX X, Sodium arsenite + TX, Sodium cyanide + TX, Sodium fluoride + TX, Sodium fluoroacetate + TX, Sodium hexafluorosilicate + TX, Sodium pentachlorophenoxide + TX, Sodium selenite + TX, Sodium tetrathiocarbonate + TX, Sodium thiocyanate + TX, Sofamide + TX, Solzidine + TX, Spiroxamine + TX, SSI-121 + TX, Steinernema viviones Steinernema bibionis)+TX, Steinernema carpocapsae+TX, Steinernema feltiae+TX, Steinernema glaseri+TX, Steinernema riobrave+TX, Steinernema riobravis+TX, Steinernema scapterisci+TX, Steinernema genus (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, τ-Fulvalinate + TX, Tadimucarb + TX, TDE + TX, Tebuconazole + TX, Tebuflofol Kin+TX, Tebupyrimphos+TX, Tecrophthalam+TX, Temephos+TX, Tepa+TX, TEPP+TX, Terarethrin+TX, Terbam+TX, tert-butyl N-[6-[[[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate+TX, Tetrachloroethane+TX, Tetrachlorothiophene+TX, Tetraconazole+TX, Tetradeca-11-en-1-ylacetate+TX, Tetra Difon+TX, Tetramethylfluthrin+TX, Tetrasul+TX, Thallium sulfate+TX, Thiabendazole+TX, Thiafenox+TX, Thiapronil+TX, Cyclophos+TX, Tifluzamide+TX, Thiocarboxyme+TX, Thiocyclam+TX, Thiocyclam hydrogen oxalate+TX, Thiodiazole copper+TX, Thiofanox+TX, Thiohempa+TX, Thiomersal+TX, Thiometon+TX, Thionadin+TX, Thiophanate+TX, Thiophanate-methyl+TX, Thioquinox+TX, Thiosultap+TX, Thiosultap-sodium +TX, Thiotepa+TX, Thyram+TX, Turingiencin+TX, Thiazinyl+TX, Tolcrophos-methyl+TX, Tolprocarb+TX, Trilfluanide+TX, Tralomethrin+TX, Transpermethrin+TX, Tretamine+TX, Triadimephon+TX, Triadimenol+TX, Triamiphos+TX, Triatene+TX, Triazamate+TX, Triazophos+TX, Triazoxide+TX, Triazurone+TX, Tributyltin oxide+TX, Trichlormetaphos-3+TX, Trichloronate+TX, Tricogramma spp.)+TX, Triclopyricarb+TX, Tricyclazole+TX, Tridemorph+TX, Triphenmorph+TX, Triphenofos+TX, Trifloxystrobin+TX, Triflumizole+TX, Triforine+TX, Trimedrua+TX, Trimedrua A+TX, Trimedrua B1+TX, Trimedrua B2+TX, Trimedrua C+TX, Trimetacarb+TX, Trinactin+TX, Trinexapac+TX, Triphenyltin acetate+TX, Triphenyltin hydroxide+TX, Triplene+TX, Triticonazole+TX, Trunkcol+TX, Typhlodromus osidentalis Occidentalis + TX, Uredepa + TX, Validamycin + TX, Valifenarate + TX, Bamidthion + TX, Vaniliprole + TX, Veratridine + TX, Veratrin + TX, Berbutin + TX, Verticillium lecanii + TX, Vinclozoline + TX, Warfarin + TX, XMC + TX, Xylenol + TX, Zeatin + TX, Zetametrin + TX, Zhongshengmycin + TX, Zinc naphthenate + TX, Zinc phosphide + TX, Zinc thiazole + TX, Zineb + ​​TX, Ziram + TX, Zolaprofos + TX; Acinetobacter lwoffii + TX, Acremonium alternatum + TX + TX, Acremonium cephalosporium + TX + 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®)+TX, Aspergillus flavus AF36 (AF36®)+TX, Aspergillus flavus NRRL 21882 (Aflaguard®)+TX, Aspergillus spp.)+TX, Aureobasidium pullulans+TX, Azospirillum (MicroAZ(registered trademark), TAZO B(registered trademark))+TX, Azotobacter+TX, Azotobacter chroocuccum (Azotomeal(registered trademark))+TX, Azotobacter cysts (Bionatural Blooming Blossoms(registered trademark))+TX, Bacillus amyloliquefaciens+TX, Bacillus cereus+TX, Bacillus chitinosporus strain AQ746+TX, Bacillus chitinosporus (Bacillus Bacillus chitinosporus strain CM-1 + TX, Bacillus circulans + TX, Bacillus firmus (BioSafe®, BioNem-WP®), especially strain CNMC 1-1582 (e.g., VOTIVO® from BASF SE) + TX, Bacillus licheniformis strain 3086 (EcoGuard®, Green Releaf®) + TX, Bacillus licheniformis strain HB-2 (Biostart®). ), (formerly known as Rhizoboost®) +TX, Bacillus macerans +TX, Bacillus marismortui +TX, Bacillus megaterium +TX, Bacillus mycoides strain AQ726 +TX, Bacillus papillae (Milky Spore Powder®) +TX, Bacillus pumilus spp. +TX, Bacillus pumilus strain AQ717 +TX, Bacillus pumilus strain GB34 (Yield Shield®) +TX, Bacillus pumilus strain QST 2808 (Sonata®, Ballad Plus®) + TX, Bacillus sphaericus (VectoLex®) + TX, Bacillus spp. + TX, Bacillus spp. strain AQ175 + TX, Bacillus spp. strain AQ177 + TX, Bacillus spp. strain AQ178 + TX, Bacillus subtilis strain AQ153 + TX, Bacillus subtilis strain AQ743 + TX, Bacillus subtilis strain QST 713 (CEASE®, Serenade®, Rhapsody®) + TX, Bacillus Bacillus subtilis strain QST 714 (JAZZ®)+TX, Bacillus subtilis strain QST3002+TX, Bacillus subtilis strain QST3004+TX, Bacillus subtilis var. amyloliquefaciens.amyloliquefaciens) strain FZB24 (Taegro®, Rhizopro®) + TX, Bacillus thuringiensis aizawai GC 91 (Agree®) + TX, Bacillus thuringiensis Cry 2Ae + TX, Bacillus thuringiensis Cry1Ab + TX, Bacillus thuringiensis israelensis (BMP123®, Aquabac®, VectoBac®) + TX, Bacillus thuringiensis crustaki (Bacillus thuringiensis Bacillus thuringiensis kurstaki (Javelin®, Deliver®, CryMax®, Bondide®, Scutella WP®, Turilav WP®, Astuto®, Dipel WP®, Biobit®, Foray®) + TX, Bacillus thuringiensis kurstaki BMP 123 (Baritone®) + TX, Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF / 3P®) + TX, Bacillus thuringiensis strain AQ52 + TX, Bacillus thuringiensis Bacillus thuringiensis) strain BD#32+TX, Bacillus thuringiensis tenebrionis (Novodor®, BtBooster)+TX, Bacillus thuringiensis var. aizawai (XenTari®, DiPel®)+TX, Bacteria spp.)(GROWMEND(registered trademark), GROWSWEET(registered trademark), Shootup(registered trademark))+TX, Clavipacter michiganensis bacteriophage (AgriPhage(registered trademark), Bakflor(registered trademark))+TX, Beauveria bassiana (Beaugenic(registered trademark), Brocaril WP(registered trademark))+TX, Beauveria bassiana GHA (Mycotrol ES(registered trademark), Mycotrol O(registered trademark), BotaniGuard(registered trademark))+TX, Beauveria brongniartii (Engerlingspilz(registered trademark), Schweizer Beauveria(registered trademark), Melocont(registered trademark))+TX, Beauveria spp.+TX, Botrytis cineria cineria)+TX, soybean rhizobia (Bradyrhizobium japonicum) (TerraMax®)+TX, Brevibacillus brevis+TX, Burkholderia cepacia (Deny®, Intercept®, Blue Circle®)+TX, Burkholderia gladii+TX, Burkholderia gladioli+TX, Burkholderia spp.)+TX, Canadian thistle fungus (CBH Canadian Bioherbicide®)+TX, Candida butyri+TX, Candida famata+TX, Candida fructus+TX, Candida glabrata+TX, Candida guilliermondii+TX, Candida melibiosica+TX, Candida oleophila strain O+TX, Candida parapsilosis+TX, Candida pelliculosa+TX, Candida pulcherrima(Candida) Candida pulcherrima)+TX, Candida reukaufii+TX, Candida saitoana (Bio-Coat®, Biocure®)+TX, Candida sake+TX, Candida spp.+TX, Candida tenius+TX, . Cedecea davisae + TX, Cellulomonas flavigena + TX, Chaetomium cochliodes (Nova-Cide®) + TX, Chaetomium globosum (Nova-Cide®) + TX, Chromobacterium subtsugae strain PRAA4-1T (Grandevo®) + TX, Cladosporium chlorocephalum + TX, Cladosporium cladosporioides + TX, Cladosporium oxysporum + TX, Cladosporium genus spp.)+TX, Cladosporium tenuissimum+TX, Clonostachys rosea (EndoFine®)+TX, Colletotrichum acutatum+TX, Coniothyrium minitans (Cotans WG®)+TX, Coniothyrium genus (Coniothyrium spp.)+TX, Cryptococcus albidus (YIELDPLUS(registered trademark))+TX, Cryptococcus humicola+TX, Cryptococcus infirmo-miniatus+TX, Cryptococcus laurentii+TX, Cryptophlebia leucotreta granulovirus (Cryptex(registered trademark))+TX, Cupriavidus campinensis+TX, Codlinga granulosis virus (Cydia pomonella granulovirus) (CYD-X(registered trademark), Madex(registered trademark), Madex(registered trademark)Plus, Madex Max, Carpovirusine® + TX, Cylindrobasidium laeve (Stumpout®) + TX, Cylindrocladium + TX, Debaryomyces hansenii + TX, Drechslera hawaiinensis + TX, Enterobacter cloacae + TX, Enterobacteriaceae + TX, Entomophtora virulenta (Vektor®) + TX, Epicoccum nigrum + TX, Epicoccum purpurascens + TX, Epicoccum spp.)+TX, Filobasidium floriforme+TX, Fusarium acuminatum+TX, Fusarium chlamydosporum+TX, Fusarium oxysporum (Fusaclean®, Biofox C®)+TX, Fusarium proliferatum+TX, Fusarium spp.+TX, Galactomyces geotrichum+TX, Gliocladium catenulatum (Primastop®, Prestop®)+TX, Gliocladium roseum roseum)+TX, Gliocladium spp. (SoilGard®)+TX, Gliocladium virens (Soilgard®)+TX, Granulovirus (Granupom®)+TX, Halobacillus halophilus+TX, Halobacillus litoralis+TX, Halobacillus trueperi+TX, Halomonas spp.)+TX, Halomonas subglaciescola+TX, Halovibrio variabilis+TX, Hanseniaspora uvarum+TX, Helicoverpa armigera nuclear polyhedra virus (Helicovex®)+TX, Helicoverpa zea nuclear polyhedra virus (Gemstar®)+TX, Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus strain, PFR-97®, PreFeRal®)+TX, isoflavone formononetin (Myconate®)+TX, Kloeckera apiculata apiculata)+TX, Kloeckera spp.)+TX, Lagenidium giganteum (Laginex®)+TX, Lecanicillium lecanii strain KV01 (formerly known as Verticillium lecanii) (Mycotal®) conidia (e.g., Vertalec® from Koppert / Arysta)+TX, greenhouse whitefly (Lecanicillium longisporum) (Vertiblast®)+TX, Lecanicillium muscarium (Vertikil®)+TX, gypsy moth (Lymantria dispar) nuclear polyhedron virus (Disparvirus®)+TX, Marinococcus halophilus+TX, Meira geuraconigii geulakonigii)+TX, Metarhizium anisopliae (Destruxin WP(registered trademark))+TX, Metarhizium anisopliae (Met52(registered trademark))+TX, Metschnikowia fruticola (Shemer(registered trademark))+TX, Metschnikowia pulcherrima+TX, Microdochium dimerum (Antibot(registered trademark))+TX, Micromonospora coerulea+TX, Microsphaeropsis ochracea+TX, Muscodor albus albus)620(Muscudor(registered trademark))+TX, Muscodor roseus, especially strain A3-5 (acceptance number NRRL 30548)+TX, Mycorrhizae spp.)(AMykor(registered trademark), Root Maximizer(registered trademark))+TX, Mulberry dark spot disease fungus (Myrothecium verrucaria) strain AARC-0255 (DiTera(registered trademark), BROS PLUS(registered trademark))+TX, Ophiostoma piliferum strain D97 (Sylvanex(registered trademark))+TX, Paecilomyces farinosus+TX, Paecilomyces lilacinus strain 251 (MeloCon WG(registered trademark))+TX, Paecilomyces linacinus (Biostat WP(registered trademark))+TX, Paenibacillus polymixa polymyxa)+TX, Pantoea agglomerans (BlightBan C9-1(registered trademark))+TX, 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, Phosphollytic bacteria (Phosphomeal®)+TX, Phytophthora cryptogea+TX, Phytophthora palmivora (Devine®)+TX, Pichia anomala+TX, Pichia guilliermondii+TX, Pichia membranaefaciens+TX, Pichia onychis+TX, Pichia stipites+TX, Pseudomonas aeruginosa) + TX, Pseudomonas aureofasciens (Spot-Less Biofungicide®) + TX, . Pseudomonas cepacia + TX, Pseudomonas chlororaphis (AtEze®) + TX, Pseudomonas corrugate + TX, Pseudomonas fluorescens (Zequanox®) + TX, Pseudomonas fluorescens strain A506 (BlightBan A506®) + TX, Pseudomonas putida + TX, Pseudomonas reactans + TX, Pseudomonas spp. + TX, Pseudomonas syringae (Bio-Save®) + TX, Pseudomonas viridiflava viridiflava)+TX, Pseudozyma flocculosa strain PF-A22 UL (Sporodex L(registered trademark))+TX, Puccinia canaliculata+TX, Puccinia thlaspeos (Wood Warrior(registered trademark))+TX, Pythium paroecandrum+TX, Pythium oligandrum (Polygandron(registered trademark), Polyversum(registered trademark))+TX, Pythium periplocum+TX, Rhanella aquatilis+TX, Rhanella spp.)+TX, Rhizobia (Dormal®, Vault®)+TX, Rhizoctonia+TX, Rhodococcus globerulus strain AQ719+TX, Rhodosporidium diobovatum+TX, Rhodosporidium toruloides+TX, Rhodotorula spp.+TX, Rhodotorula glutinis+TX, Rhodotorula graminis+TX, Rhodotorula mucilagnosa+TX, Rhodotorula rubra+TX, Rhodotorula spp.)+TX, Saccharomyces cerevisiae+TX, Salinococcus roseus+TX, Sclerotinia minor (SARRITOR®)+TX, Sclerotinia minor+TX, Scytalidium spp.+TX, Scytalidium 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+TX, Streptomyces albaduncus+TX, Streptomyces exfoliates+TX, Streptomyces galbus+TX, Streptomyces glyceoplanus (Streptomyces griseoplanus)+TX, Streptomyces griseoviridis (Mycostop®)+TX, Streptomyces hygroscopicus+TX, Streptomyces lydicus (Actinovate®)+TX, Streptomyces lydicus WYEC-108 (ActinoGrow®)+TX, Streptomyces violaceus+TX, Tilletiopsis minor+TX, Tilletiopsis spp.)+TX, Trichoderma asperellum (T34 Biocontrol®)+TX, Trichoderma atroviride (Plantmate®)+TX, Trichoderma gamsii (Tenet®)+TX, Trichoderma hamatum TH 382+TX, Trichoderma harzianum rifai (Mycostar®)+TX, Trichoderma harzianum T-22 (Trianum-P®, PlantShield HC®, RootShield®, 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 genus (Trichoderma spp.)LC 52 (Sentinel (registered trademark)) + TX, Trichoderma taxi + TX, Trichoderma virens (formerly known as Gliocladium virens GL-21) (SoilGuard (registered trademark)) + TX, Trichoderma virens + TX, Trichoderma viride + TX, Trichoderma viride strain ICC 080 (Remedier (registered trademark)) + TX, Trichosporon pullulans + TX, Trichosporon spp. + TX, Trichothecium roseum + TX, Trichothecium genus spp.)+TX, Typhula phacorrhiza strain 94670+TX, Typhula phacorrhiza strain 94671+TX, Ulocladium atrum+TX, Ulocladium oudemansii (Botry-Zen®)+TX, Ustilago maydis+TX, various bacteria and auxiliary micronutrients (Natural II®)+TX, various fungi (Millennium Microbes®)+TX, Verticillium chlamydosporium Chlamydosporium)+TX, Vip3Aa20 (VIPtera(registered trademark))+TX, Virgibaclillus marismortui+TX, Xanthomonas campestris pv. Poae (Camperico(registered trademark))+TX, Xenorhabdfus bovienii+TX, Xenorhabdus nematophilus+TX;. AGNIQUE® MMF + TX, Azadirachtin (Plasma Neem Oil®, AzaGuard®, MeemAzal®, Molt-X®, e.g., AZATIN XL from Certis, USA) + TX, Botanical Insect Growth Regulators (Botanical IGRs) (Neemazad®, Neemix®) + TX, BugOil® + TX, Rapeseed Oil (Lilly Miller Vegol®) + TX, American Antwort (Chenopodium ambrosioides near ambrosioides) (Requiem®) + TX, Chrysanthemum Extract (Crisant®) + TX, Lamiaceae Essential Oil (Botania®) + TX, Neem Oil Extract (Trilogy®) + TX, Clove, Rosemary, Peppermint and Thyme Oil Extract (Garden insect Killer® + TX, Garlic + TX, Glycine Betaine (Greenstim®) + TX, Kaolin (Screen®) + TX, Lemongrass Oil (GreenMatch®) + TX, Tea Tree (Melaleuca alternifolia) Extract (also known as Tea Tree Oil) (Timorex Gold®) + TX, Clove Peppermint Garlic Oil and Mint Mixture (Soil Shot®) + TX, Clove Rosemary and Peppermint Extract Mixture (EF 400®) + TX, Rosemary Sesame Peppermint Thyme and Cinnamon Extract Mixture (EF 300®) + TX, Neem Oil + TX, Catnip (Nepeta cataria) (Catnip Oil) + TX, Catnip (Nepeta Catarina) + TX, Nicotine + TX, Oregano oil (MossBuster®) + TX, Pedaliaceae oil (Nematon®) + TX, Pine oil (Retenol®) + TX, Pyrethrum + TX, Soap tree (Quillaja saponaria) (NemaQ®) + TX, Japanese knotweed (Reynoutria)sachalinensis (Regalia®, Sakalia®) + TX, rotenone (Eco Roten®) + TX, Rutaceae plant extract (Soleo®) + TX, soybean oil (Ortho ecosense®) + TX, brown algae storage glucan (Laminarin®) + TX, thyme oil + TX; (E,Z)-7,9-Dodecadiene-1-yl acetate + TX, (E,Z,Z)-3,8,11-Tetradecatrienylate + TX, (Z,Z,E)-7,11,13-Hexadecatrienal + TX, 2-Methyl-1-butanol + TX, Biolure® + TX, Blackheaded Fireworm Pheromone (3M Sprayable Blackheaded Fireworm Pheromone®) + TX, Calcium Acetate + TX, Check-Mate® + TX, Codling Moth Pheromone (Paramount dispenser-(CM) / Isomate C-Plus®) + TX, Entostat Powder (Exosex CM®) (Exosex extract from palm trees) + TX, Grape Berry Moth Pheromone (3M MEC-GBM Sprayable Pheromone(registered trademark) + TX, Lavanzuryl senecioate + TX, Leafroller pheromone (3M MEC-LR Sprayable Pheromone(registered trademark)) + TX, Muscamone (Snip7 Fly Bait(registered trademark)) + TX, Oriental Fruit Moth pheromone (3M oriental fruit moth sprayable pheromone(registered trademark)) + TX, Peachtree Borer pheromone (Isomate-P(registered trademark)) + TX, Scenturion(registered trademark) + TX, Starbar Premium Fly Bait(registered trademark)) + TX, Tomato pinworm pheromone (3M Sprayable pheromone(registered trademark)) + TX; Acerophagus papaya + TX, Adalia bipunctata (Adalia-System®) + TX, Adalia bipunctata (Adaline®) + TX, Adalia bipunctata (Aphidalia®) + TX, Ageniaspis citricola + TX, Ageniaspis fuscicollis + TX, Amblyseius andersoni (Anderline®, Andersoni-System®) + TX, Amblyseius californicus (Amblyline®, Spical®) + TX, Amblyseius cucumeris cucumeris) (Thripex®, Bugline cucumeris®) + TX, Amblyseius fallacis (Fallacis®) + TX, Amblyseius swirskii (Bugline swirskii®, Swirskii-Mite®) + TX, Amblyseius womersleyi (WomerMite®) + TX, Amitus hesperidum + TX, Anagrus atomus + TX, Anagyrus fusciventris + TX, Anagyrus kamali + TX, Anagyrus loecki+TX, Anagyrus pseudococci (Citripar®)+TX, Anicetus benefices+TX, Anisopteromalus calandrae+TX, Anthocoris nemoralisnemoralis)(Anthocoris-System(registered trademark))+TX, Aphelinus abdominalis (Apheline(registered trademark)), Aphiline(registered trademark))+TX, Aphelinus asychis+TX, Aphidius colemani (Aphipar(registered trademark))+TX, Aphidius ervi (Aphelinus-System(registered trademark))+TX, Aphidius ervi (Ervipar(registered trademark))+TX, Aphidius gifuensis+TX, Aphidius matricariae (Aphipar-M(registered trademark))+TX, Aphidoletes aphidimyza (Aphidend(registered trademark), Aphidoline(registered trademark))+TX, Aphytis lingnanensis (Aphytis lingnanensis)+TX, Aphytis melinus+TX, Aprostocetus hagenowii+TX, Atheta coriaria (Staphyline®)+TX, Bombus spp.)+TX, European bumblebee (Bombus terrestris) (Beeline®, Tripol®)+TX, European bumblebee (Bombus terrestris) (Natupol Beehive®)+TX, Cephalonomia stephanoderis+TX, Chilocorus nigritus+TX, Japanese lacewing (Chrysoperla carnea) (Chrysoline®, Chrysopa®)+TX, Chrysoperla rufilabris+TX, Cirrospilus ingenuus+TX, Cirrospilus quadristriatus (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+TX, Cryptolaemus montrouzieri (Cryptobug®, Cryptoline®)+TX, Cybocephalus nipponicus+TX, Dacnusa sibirica)(Minusa(registered trademark), DacDigline(registered trademark), Minex(registered trademark))+TX, Delphastus catalinae(Delphastus(registered trademark))+TX, Delphastus pusillus+TX, Diachasmimorpha krausii+TX, Diachasmimorpha longicaudata+TX, Diaparsis jucunda+TX, Diaphorencyrtus aligarhensis+TX, Diglyphus isaea) (Diminex(registered trademark), Miglyphus(registered trademark), Digline(registered trademark)) + TX, Diversinervus genus (Diversinervus spp.))+TX, Encarsia citrina+TX, Encarsia formosa (Encarsia max(registered trademark), Encarline(registered trademark), En-Strip(registered trademark))+TX, Encarsia guadeloupae+TX, Encarsia haitiensis+TX, Episyrphus balteatus (Syrphidend(registered trademark))+TX, Eretmoceris siphonini+TX, Eretmocerus californicus+TX, desert. Eretmocerus eremicus (Enermix®, Ercal®, Eretline e®, Bemimix®) + TX, Eretmocerus hayati + TX, Eretmocerus mundus (Bemipar®, Eretline m®) + TX, Eretmocerus siphonini + TX, Exochomus quadripustulatus + TX, Feltiella acarisuga (Feltiline®) + TX, Feltiella acarisuga (Spidend®) + TX, Phopius alisanus arisanus)+TX, Fopius ceratitivorus+TX, Hormononetin (Wirless Beehome®)+TX, Franklinothrips vespiformis (Vespop®)+TX, Galendromus occidentalis+TX, Goniozus legneri+TX, Habrobracon hebetor+TX, Harmonia axyridis (HarmoBeetle®)+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), Exhibitlinehm(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 errabundus+TX, Leptomastidea abnormis abnormis)+TX, Leptomastix dactylopii (Leptopar®)+TX, Leptomastix epona+TX, Lindorus lophanthae+TX, Lipolexis oregmae+TX, Lucilia caesar (Natufly®)+TX, Lysiphlebus testaceipes+TX, Macrolophus caliginosus (Mirical-N®, Macroline c®, Mirical®)+TX, Mesoseiulus longipes longipes)+TX, Metaphycus flavus+TX, Metaphycus lounsburyi+TX, Micromus angulatus (Milacewing(registered trademark))+TX, Microterys flavusflavus)+TX, Muscidifurax raptorellus and Spalangia cameroni (Biopar®)+TX, Neodryinus typhlocybae+TX, Neoseiulus californicus+TX, Neoseiulus cucumeris (THRYPEX®)+TX, Neoseiulus fallacis+TX, Nesideocoris tenuis (NesidioBug®, Nesibug®)+TX, Ophyra aenecens aenescens)(Biofly(registered trademark))+TX, Shinobihana-kamemushi (Orius insidiosus)(Thripor-I(registered trademark), Oriline i(registered trademark))+TX, Elhimehana-kamemushi (Orius laevigatus)(Thripor-L(registered trademark), Oriline l(registered trademark))+TX, Orius majusculus (Orius majusculus)(Oriline m(registered trademark))+TX, Tairikuhimehana-kamemushi (Orius strigicollis)(Thripor-S(registered trademark))+TX, Pauesia juniperorum+TX, Pediobius foveolatus+TX, Phasmarhabditis hermaphrodita hermaphrodita) (Nemaslug®) + TX, Phymastichus coffea + TX, Phytoseiulus macropilus + TX, Phytoseiulus persimilis (Spidex®, Phytoline p®) + TX, Podisus maculiventris (Podisus®) + TX, Pseudacteon curvatus + TX, Pseudacteon obtusus + TX, Pseudacteon tricuspis + TX, Pseudaphycus maculipennis + TX, Pseudleptomastix mexicana + TX, Psyllaephagus pilosus + TX, Psyttalia concolor (complex) + TX, Quadrastichus spp.)+TX, Rhyzobius lophanthae+TX, Rodolia cardinalis+TX, Rumina decollate+TX, Semielacher petiolatus+TX, Sitobion avenae (Ervibank®)+TX, Steinernema carpocapsae (Nematac C®, Millennium®, BioNem C®, NemAttack®, Nemastar®, Capsanem®)+TX, Steinernema feltiae (NemaShield®, Nemasys F®, BioNem F (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. (genus Steinernema) + TX, Steinernematid spp. (genus Steinernematid))(Guardian Nematodes(registered trademark))+TX, Stethorus punctillum(Stethorus(registered trademark))+TX, Tamarixia radiate+TX, Tetrastichus setifer+TX, Thripobius semiluteus+TX, Torymus sinensis+TX, Trichogramma brassicae(Tricholine b(registered trademark))+TX, Trichogramma brassicae(Tricho-Strip(registered trademark))+TX, Trichogramma evanescens+TX, Trichogramma minutum+TX, Trichogramma * ostriniae* + TX, * Trichogramma platneri* + TX, * Trichogramma pretiosum* + TX, * Xanthopimpla stemmator*; Abscisic acid + TX, Aminomite® + TX, BioGain® + TX, bioSea® + TX, CAS number: 2643947-26-4 + TX, Chondrostereum purpureum (Chontrol Paste®) + TX, Colletotrichum gloeosporioides (Collego®) + TX, Copper octanoate (Cueva®) + TX, Delta Trap (Trapline d®) + TX, Erwinia amylovora (Harpin) (ProAct®), Ni-HIBIT Gold CST(registered trademark))+TX, fatty acids derived from natural by-products of extra virgin olive oil (FLIPPER(registered trademark))+TX, ferric phosphate (Ferramol(registered trademark))+TX, funnel trap (Trapline y(registered trademark))+TX, Gallex(registered trademark)+TX, Grower's Secret(registered trademark)+TX, homo-brassonolide+TX, iron phosphate (Lilly Miller Worry Free Ferramol Slug & Snail Bait(registered trademark))+TX, MCP hail trap (Trapline f(registered trademark))+TX, Microctonus hyperodae+TX, Mycoleptodiscus terrestris (Des-X(registered trademark))+TX, Nosema locustae (Semaspore Organic Grasshopper) Control(registered trademark)) + TX, Pheromone Trap (Thripline)ams(registered trademark))+TX, potassium bicarbonate (MilStop(registered trademark))+TX, potassium iodide + potassium thiocyanate (Enzicur(registered trademark))+TX, potassium salt of fatty acid (Sanova(registered trademark))+TX, potassium silicate solution (Sil-Matrix(registered trademark))+TX, spider venom+TX, sticky trap (Trapline YF(registered trademark), Rebell Amarillo(registered trademark))+TX, SuffOil-X(registered trademark)+TX, trap (Takitrapline y+b(registered trademark))+TX; Bacillus mojavensis strain R3B (acceptance number NCAIM(P)B001389) (International Publication No. 2013 / 034938) + TX manufactured by Certis USA LLC; Bacillus pumilus, in particular strain BU F-33 (CARTISSA® manufactured by BASF, EPA registration number 71840-19) with NRRL acceptance number 50185 + TX; Bacillus subtilis CX-9060 + TX manufactured by Certis USA LLC; Bacillus sp., in particular strain D747 (available as DOUBLE NICKEL® manufactured by Kumiai Chemical Industry Co., Ltd.), with acceptance number FERM BP-8234, U.S. Patent No. 7,094,592 + TX; Bacillus subtilis Bacillus subtilis var. amyloliquefaciens strain FZB24 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5)) +TX, with strain BU1814 (VELONDIS® PLUS, VELONDIS® FLEX, and VELONDIS® EXTRA manufactured by BASF SE, acceptance number DSM 10271), Bacillus subtilis, particularly strain QST713 / AQ713 (NRRL acceptance number B-21661, described in U.S. Patent No. 6,060,051, Bayer CropScience) Paenibacillus polymyxa, particularly strain AC-1 (e.g., TOPSEED® from Green Biotech Company Ltd.) +TX, with acceptance number NRRL B-50972 or acceptance number NRRL B-67129, is a member of the Paenibacillus genus.) strain, International Publication No. 2016 / 154297 + TX, Pantoea agglomerans, in particular strain E325 (acceptance number NRRL B-21856) (available as BLOOMTIME BIOLOGICAL® FD BIOPESTICIDE from Northwest Agri Products) + TX, Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena) + TX; Aureobasidium pullulans, particularly spores of strain DSM14940, spores of strain DSM14941, or mixtures of spores of strains DSM14940 and DSM14941 (e.g., BOTECTOR® and BLOSSOM PROTECT® from bio-ferm, CH) + TX; Pseudozyma aphidis (disclosed in International Publication No. 2011 / 151819 by Yissum Research Development Company of the Hebrew University of Jerusalem) + TX; Saccharomyces cerevisiae from Lesaffre et Compagnie, FR cerevisiae), particularly strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938 or CNCM No. 1-3939 (International Publication No. 2010 / 086790) + TX; Agrobacterium radiobacter strain K84 (e.g., GALLTROL-A® from AgBioChem, CA) + TX, Bacillus amyloliquefaciens isolate B246 (e.g., AVOGREEN® from University of Pretoria) + TX, Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL acceptance number B-50768, International Publication No. 2014 / 028521) (STARGUS® from Marrone Bio Innovations) + TX, Bacillus amyloliquefaciens strain FZB42, acceptance number DSM 23117 (available as RHIZOVITAL® from ABiTEP, DE) + TX, Bacillus amyloliquefaciens, especially strain D747 (acceptance number FERM BP-8234, available as Double Nickel® from Kumiai Chemical Industry Co., Ltd., U.S. 7,094,(Specification No. 592) +TX, Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (QUARTZO® (WG) and PRESENCE® (WP) manufactured by FMC Corporation) +TX, Bacillus licheniformis having acceptance number ATCC 55406, in particular strain SB3086, International Publication No. 2003 / 000051 (available as ECOGUARD® Biofungicide and GREEN RELEAF® manufactured by Novozymes) +TX, Bacillus methylotrophicus strain BAC-9912 (Chinese Academy of Sciences' Institute of Applied Bacillus mycoides (manufactured by Ecology) +TX, acceptance number B-30890, isolate (available as BMJ TGAI® or WG and LifeGard® from Certis USA LLC) +TX, Bacillus pumilus, in particular strain GB34 (available as Yield Shield® from Bayer AG, DE) +TX, Bacillus pumilus, in particular strain QST2808 (with acceptance number NRRL B-30087, described in U.S. Patent No. 6,245,551, Bayer CropScience LP,(Available as SONATA® from the US) +TX, Bacillus subtilis CX-9060 +TX from Certis USA LLC, Bacillus subtilis IAB / BS03 (AVIV® from STK Bio-Ag Technologies, PORTENTO® from Idai Nature) +TX, Bacillus subtilis KTSB strain (FOLIACTIVE® from Donaghys) +TX, Bacillus subtilis strain BU1814 (Available as VELONDIS® PLUS, VELONDIS® FLEX and VELONDIS® EXTRA from BASF SE) +TX, Bacillus subtilis strain GB03 (Available as Kodiak® from Bayer AG, DE) +TX, Bacillus subtilis with acceptance number NRRL B-50595 Bacillus subtilis) strain MBI 600 (available as SUBTILEX from BASF SE), U.S. Patent No. 5,061,495 + TX, Bacillus subtilis strain Y1336 (registered in Taiwan as a biological fungicide and mycicide under registration numbers 4764, 5454, 5096 and 5277, available as BIOBAC® WP from Bion-Tech, Taiwan) + TX, Bacillus subtilis var. amyloliquefaciens strain FZB24 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5)) + TX, Bacillus subtilis (subtilis) Y1336 (Registered in Taiwan as a biological fungicide and mycicide under registration numbers 4764, 5454, 5096 and 5277, Bion-Tech,Available as BIOBAC(registered trademark)WP from Taiwan +TX, Paenibacillus epiphyticus (International Publication No. 2016 / 020371) from BASF SE +TX, Paenibacillus polymyxa ssp. plantarum (International Publication No. 2016 / 020371) from BASF SE +TX, Paenibacillus sp. strains with acceptance number NRRL B-50972 or acceptance number NRRL B-67129, Pseudomonas chlororaffis (International Publication No. 2016 / 154297 +TX) with acceptance number NRRL B-50897 Chloraphis strain AFS009, International Publication No. 2017 / 019448 (e.g., AgBiome Innovations,US-made HOWLER (trademark) and ZIO (registered trademark) + TX, Pseudomonas chlororaphis, especially strain MA342 (e.g., CEDOMON (registered trademark), CERALL (registered trademark), and CEDRESS (registered trademark) from Bioagri and Koppert) + TX, fluorescent bacterium (Pseudomonas fluorescens) strain A506 (e.g., BLIGHTBAN (registered trademark) A506 from NuFarm) + TX, Pseudomonas proradix (e.g., PRORADIX (registered trademark) from Sourcon Padena) + TX, Streptomyces griseoviridis strain K61 (also known as Streptomyces galbus strain K61) (acceptance number DSM) 7206) (MYCOSTOP® manufactured by Verdera, PREFENCE® manufactured by BioWorks, cf. Crop Protection 2006, 25, 468-475) + TX, Streptomyces lydicus strain WYEC108 (also known as Streptomyces lydicus strain WYCD108US) (ACTINO-IRON® and ACTINOVATE® manufactured by Novozymes) + TX; Trichoderma atroviride strain T11 (IMI352941 / CECT20498) + TX, Ampelomyces quisqualis strain AQ10 (e.g., AQ 10® from IntrachemBio Italia) + TX with acceptance number CNCM 1-807, Ampelomyces quisqualis, especially strain AQ 10 (e.g., AQ 10® from IntrachemBio Italia) + TX, Aspergillus flavus strain NRRL 21882 (product known as AFLA-GUARD® from Syngenta / ChemChina) + TX, Aureobasidium pullulans, especially strain DSM Spores of 14941 + TX, Aureobasidium pullulans, especially spores of strain DSM14940 + TX, Aureobasidium pullulans, especially a mixture of spores of strains DSM14940 and DSM 14941 (e.g., bio-ferm,Botector® (registered trademark) from CH + TX, Chaetomium cupreum (acceptance number CABI 353812) (e.g., BIOKUPRUM® from AgriLife) + TX, Chaetomium globosum (available as RIVADIOM® from Rivale) + TX, Cladosporium cladosporioides, strain H39, U.S. Patent Application Publication No. 2010 / 0291039 (by Stichting Dienst Landbouwkundig Onderzoek) + TX, Coniothyrium minitans, particularly strain CON / M / 91-8 (acceptance number DSM9660, e.g., Bayer CropScience Biologics) Contans(registered trademark) +TX from GmbH, Cryptococcus flavescens, strain 3C (NRRL Y-50378), +TX, Dactylaria candida, Dilophosphora alopecuri (available as TWIST FUNGUS(registered trademark)), Fusarium oxysporum, strain Fo47 (available as FUSACLEAN(registered trademark) from Natural Plant Protection) +TX, Gliocladium catenulatum (synonym: Clonostachys rosea f. catenulate), strain J1446 (e.g., Prestop from Lallemand) (Registered Trademark) +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), particularly strain 321U from Adjuvants Plus, strain ACM941+TX as disclosed in Xue AG (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root tot complex of field pea, Can Jour Plant Sci 2003, 83(3):519-524), Metschnikowia fructicola, particularly strain NRRL Y-30752+TX, Microsphaeropsis ochracea, Penicillium steckii (DSM 27859, International Publication No. 2015 / 067800)+TX from BASF SE, Trichoderma asperellum strain ICC 012 (also known as Trichoderma harzianum ICC012) with acceptance number CABI CC IMI 392716, and Trichoderma gamsii (formerly known as T. viride strain ICC 080) with acceptance number IMI 392151 (e.g., BIO-TAM (trademark) from Isagro USA, Inc. or Agrobiosol de Mexico,Mixture of BIODERMA® by SAde CV + TX, Penicillium vermiculatum + TX, Phlebiopsis gigantea strain VRA 1992 (ROTSTOP® C from Danstar Ferment) + TX, Pseudozyma flocculosa strain PF-A22 UL (available as SPORODEX® L from Plant Products Co., CA) + TX, Saccharomyces cerevisiae strain LAS117 cell wall (CEREVISANE® from Lesaffre, ROMEO® from BASF SE) + TX, Saccharomyces cerevisiae from Lesaffre et Compagnie, FR Saccharomyces cerevisiae strains CNCM numbers 1-3936, 1-3937, 1-3938, 1-3939 (International Publication No. 2010 / 086790) + TX, Saccharomyces cerevisiae, especially strain LASO2 (manufactured by Agro-Levures et Derives) + TX, Simplicillium lanosoniveum + TX, strain T34 (e.g., T34 Biocontrol from Biocontrol Technologies SL,ES) or strain ICC 012 from Isagro + TX, Strain WRL-076 (NRRL Y-30842), U.S. Patent No. 7,579,183 + TX, Talaromyces flavus, strain V117b + TX, Trichoderma asperelloides JM41R (acceptance number NRRL B-50759) (TRICHO PLUS® manufactured by BASF SE) + TX, Trichoderma asperellum having acceptance number FERM P-16510, especially strain SKT-1 (e.g., ECO-HOPE® manufactured by Kumiai Chemical Industry) + TX, Trichoderma asperellum, especially strain kd (e.g., T-Gro manufactured by Andermatt Biocontrol) + TX, Trichoderma atroviride Trichoderma atroviride strain 77B (T77 from Andermatt Biocontrol) + TX, Trichoderma atroviride strain ATCC 20476 (IMI 206040) + TX, Trichoderma atroviride strain LC52 (e.g., Tenet from Agrimm Technologies Limited) + TX, Trichoderma atroviride strain LU132 (e.g., Sentinel from Agrimm Technologies Limited) + TX, Trichoderma atroviride strain NMI number V08 / 002388 + TX, Trichoderma atroviride strain NMI number V08 / 002389 + TX, Trichoderma atroviride Trichoderma atroviride strain NMI number V08 / 002390+TX, Trichoderma atroviride strain number V08 / 002387+TX, Trichoderma atroviride strain SKT-1 (FERMP-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, particularly strain SC1 (acceptance number CBS 122089, International Publication No. 2009 / 116106 and U.S. Patent No. 8,431,120 (from Bi-PA)) + TX, Trichoderma atroviride strain CNCM 1-1237 (e.g., Esquive® WP from Agrauxine, FR) + TX, Trichoderma fertile (e.g., TrichoPlus 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® from AGROBIOSOL DE MEXICO, SADE CV), + TX, Trichoderma gamsii strain ICC080 (IMI CC 392151 CABI, e.g., AGROBIOSOL DE MEXICO, SADE BioDerma (manufactured by CV), +TX, Trichoderma harmatum +TX, Trichoderma harmatum +TX with acceptance number ATCC 28012, Trichoderma harzianum +TX, Trichoderma harzianum Refine (Trichoderma harzianumrifai)T39 (e.g., Trichoderma harzianum strain Cepa SimbT5 (Simbiose Agro), +TX, Trichoderma harzianum strain DB 103 (Dagutat Available as Biolab's T-GRO® 7456 + TX, Trichoderma harzianum strain ITEM 908 (e.g., Trianum-P from Koppert) + TX, Trichoderma harzianum strain T-22 (e.g., Trianum-P from Andermatt Biocontrol or Koppert) + TX, Trichoderma harzianum strain TH35 (e.g., Root-Pro from Mycontrol) + TX, Trichoderma polysporum strain IMI 206039 (e.g., Binab TF WP from BINAB Bio-Innovation AB, Sweden) + TX, Trichoderma stromaticum with acceptance number Ts3550 * Trichoderma stromaticum* (e.g., Tricovab from CEPLAC, Brazil) + TX, *Trichoderma virens* (also known as *Gliocladium virens*), especially strain GL-21 (e.g., SoilGard from Certis, US) + TX, *Trichoderma virens* strain G-41 (formerly known as *Gliocladium virens*) (acceptance number ATCC 20906) (e.g., ROOTSHIELD® PLUS WP and TURFSHIELD® PLUS WP from BioWorks, US) + 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 from Koppert)+TX, Ulocladium oudemansii strain U3 (e.g., Botry-Zen Ltd, New) with acceptance number NM 99 / 06216.BOTRY-ZEN® from Zealand and BOTRYSTOP® from BioWorks, Inc. + TX; Verticillium albo-atrum (formerly V. dahliae) strain WCS850 deposited at the Central Bureau for Fungi Cultures with acceptance number WCS850 (e.g., DUTCH TRIG® from Tree Care Innovations) + TX; Verticillium chlamydosporium + TX; a mixture of Azotobacter vinelandii and Clostridium pasteurianum (available as INVIGORATE® from Agrinos) + TX; Bacillus licheniformis A mixture of Azorhizobium 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 (e.g., VERTEX-IF® from TerraMax, Inc.) + TX, Azotobacter chroococcum, especially strain H23 + TX, Azotobacter vineranzii vinelandii), especially strain ATCC 12837+TX, Bacillus amyloliquefaciens BS27 (acceptance number NRRL B-5015)+TX, Bacillus amyloliquefaciensBacillus amyloliquefaciens), especially strain FZB42 (e.g., RHIZOVITAL® manufactured by ABiTEP, DE) + TX, Bacillus amyloliquefaciens, especially strain IN937a + TX, Bacillus amyloliquefaciens pm414 (LOLI-PEPTA® manufactured by Biofilm Crop Protection) + TX, Bacillus amyloliquefaciens SB3281 (ATCC # PTA-7542, International Publication No. 2017 / 205258) + TX, Bacillus amyloliquefaciens amyloliquefaciens) TJ1000 (available as QUIKROOTS® from Novozymes) + TX, Bacillus cereus family member EE128 (NRRL number B-50917) + TX, Bacillus cereus family member EE349 (NRRL number B-50928) + TX, Bacillus cereus, especially strain BP01 (ATCC 55675, e.g., MEPICHLOR® from Arysta Lifescience, US) + TX, Bacillus mycoides BT155 (NRRL number B-50921) + TX, Bacillus mycoides BT46-3 (NRRL number B-50922) + TX, Bacillus mycoides Bacillus mycoides EE118 (NRRL number B-50918) + TX, Bacillus mycoides EE141 (NRRL number B-50916) + TX, Bacillus pumilus, especially strain GB34 (e.g., YIELD SHIELD (registered trademark) from Bayer Crop Science, DE), + TX, Bacillus pumilus, especially strain QST2808 (acceptance number NRRL number B-30087) + TX, Bacillus siamensisBacillus subtilis, particularly strain KCTC 13613T+TX, Bacillus subtilis, particularly strain AQ30002 (acceptance number NRRL number B-50421, described in US Patent Application No. 13 / 330,576)+TX, Bacillus subtilis, particularly strain AQ30004 (NRRL number B-50455, described in US Patent Application No. 13 / 330,576)+TX, Bacillus subtilis, particularly strain MBI 600 (e.g., SUBTILEX® manufactured by BASF SE)+TX, Bacillus subtilis rm303 (RHIZOMAX® manufactured by Biofilm Crop Protection)+TX, Bacillus subtilis strain BU1814 (BASF Bacillus tequilensis (available as TEQUALIS® from SE) +TX, Bacillus thuringiensis, especially strain NII-0943 +TX, Bacillus thuringiensis BT013A (NRRL number B-50924), also known as Bacillus thuringiensis 4Q7 +TX, Bradyrhizobium japonicum (e.g., OPTIMIZE® from Novozymes) +TX, Delftia acidovorans, especially strain RAY209 (e.g., BIOBOOST® from Brett Young Seeds) +TX, Lactobacillus sp.) (e.g., LACTOPLANT® from LactoPAFI) + TX, Mesorhizobium cicer (e.g., NODULATOR from BASF SE) + TX, Paenibacillus polymyxa, especially strain AC-1 (e.g., TOPSEED® from Green Biotech Company Ltd.) + TX, Pseudomonas* aeruginosa*, especially strain PN1+TX; *Pseudomonas proradix* (e.g., PRORADIX® from Sourcon Padena)+TX; *Rhizobium leguminosarium biovar viciae* (e.g., NODULATOR from BASF SE)+TX; *Rhizobium leguminosarum*, especially bv. viciae strain Z25 (acceptance number CECT 4585)+TX; *Serratia marcescens*, especially strain SRM (acceptance number MTCC 8708),+TX; *Sinorhizobium meliloti* strain NRG-185-1 (Bayer) NITRAGIN® GOLD + TX manufactured by CropScience, and Thiobacillus sp. (e.g., CROPAID® manufactured by Cropaid Ltd UK) + TX; Mulberry dark spot disease fungus (Myrothecium verrucaria) strain AARC-0255 (e.g., DiTera® from Valent Biosciences) + TX, Penicillium bilaii strain ATCC 22348 (e.g., JumpStart® from Acceleron BioAg) + TX, Penicillium bilaii strain ATCC ATCC20851 + TX, Purpureocillium lilacinum (formerly known as Paecilomyces lilacinus) strain 251 (AGAL 89 / 030550, e.g., BioAct from Bayer CropScience Biologics GmbH) + TX, Pythium oligodendrum Pythium oligandrum strain DV74+TX, Pythium oligandrum strain M1 (ATCC 38472, e.g., Polyversum manufactured by Bioprepraty, CZ)+TX, Rhizopogon amylopogon (Myco-Sol manufactured by Agri-Enterprise, LLC, formerly Helena Chemical Company)+TX, Rhizopogon fulvigleba (Myco-Sol manufactured by Agri-Enterprise, LLC, formerly Helena Chemical Company)+TX, Talaromyces flavus strain V117b+TX, Trichoderma asperellum strain (Plant Health Products,Eco-T)+TX from ZA, Trichoderma asperellum strain kd (e.g., T-Gro from Andermatt Biocontrol)+TX, Trichoderma atroviride, particularly strain number V08 / 002387+TX, Trichoderma atroviride strain CNCM 1-1237 (e.g., Esquive® WP from Agrauxine, FR)+TX, Trichoderma atroviride strain LC52 (also known as Trichoderma atroviride strain LU132, e.g., Sentinel from Agrimm Technologies Limited)+TX, Trichoderma atroviride Trichoderma atroviride strain number NMI number V08 / 002388+TX, Trichoderma atroviride strain number NMI number V08 / 002389+TX, Trichoderma atroviride strain number NMI number V08 / 002390+TX, Trichoderma atroviride strain SC1 (described in International Publication No. 2009 / 116106)+TX, Trichoderma harzianum strain 1295-22+TX, Trichoderma harzianum strain ITEM 908+TX, Trichoderma harzianum strain T-22 (e.g., Andermatt Biocontrol or Koppert's Trianum-P)+TX, Trichoderma harzianum strain TSTh20, +TX, Trichoderma virens strain GI-3+TX, Trichoderma virens strain GL-21 (e.g., Certis,SoilGard® (USA-made) +TX, Trichoderma viride strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161:125-137) +TX, Verticillium albo-atrum (formerly V. dahliae) strain WCS850 (CBS 276.92, e.g., Dutch Trig from Tree Care Innovations) +TX; Agrobacterium radiobacter strain K84 (Galltrol, manufactured by AgBiochem Inc.), +TX; Bacillus amyloliquefaciens, especially strain PTS-4838 (e.g., AVEO, manufactured by Valent Biosciences, US), +TX; Bacillus mycoides, isolate J. (e.g., BmJ, manufactured by Certis USA LLC), +TX; Bacillus sphaericus, especially serotype H5a5b strain 2362 (strain ABTS-1743) (e.g., VECTOLEX®, manufactured by Valent BioSciences, US), +TX; Bacillus thuringiensis israelensis strain BMP 144 (e.g., AQUABAC® from Becker Microbial Products IL) + TX, Bacillus thuringiensis subsp. aizawai strain GC-91 + TX, Bacillus thuringiensis subsp. aizawai, especially serotype H-7 (e.g., FLORBAC® WG from Valent BioSciences, US) + TX, Bacillus thuringiensis subsp. aizawai, especially strain ABTS-1857 (SD-1372, e.g., XENTARI® from Valent BioSciences) + TX, Bacillus thuringiensis subsp. islaerensis Bacillus thuringiensis subsp. israelensis) (serotype H-14) strain AM65-52 (acceptance number ATCC 1276) (e.g., VECTOBAC® manufactured by Valent BioSciences, US) + TX, Bacillus thuringiensis subsp.Bacillus thuringiensis subsp. kurstaki strain ABTS 351 + TX, Bacillus thuringiensis subsp. kurstaki strain BMP 123 (BARITONE from Becker Microbial Products, IL and Bayer CropScience) + TX, Bacillus thuringiensis subsp. kurstaki strain EG 2348 (LEPINOX from Certis, US) + TX, Bacillus thuringiensis subsp. kurstaki strain EG 7841 (CRYMAX from Certis, US) + TX, Bacillus thuringiensis subsp. kurstaki strain HD-1 (for example, Valent BioSciences, US-made DIPEL(registered trademark) ES)+TX, Bacillus thuringiensis subsp. kurstaki strain PB 54+TX, Bacillus thuringiensis subsp. kurstaki strain SA 11 (Certis, US-made JAVELIN)+TX, Bacillus thuringiensis subsp. kurstaki strain SA 12 (Certis, US-made THURICIDE)+TX, Bacillus thuringiensis subsp. tenebrionis strain NB 176 (SD-5428, for example, BioFa NOVODOR(registered trademark)FC)+TX manufactured by DE, Bacillus thuringiensis var. Colmeri (for example, TIANBAOBTC manufactured by Changzhou Jianghai Chemical Factory)+TX, Bacillus thuringiensis var. japonensis(japonensis) strain Buibui + TX, Bacillus thuringiensis var. kurstaki strain EVB-113-19 (e.g., BIOPROTEC® from AEF Global) + TX, Brevibacillus laterosporus + TX, Burkholderia spp., especially Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis strain MBI 305) (acceptance number NRRL B-50319, international publications 2011 / 106491 and 2013 / 032693, e.g., Marrone Bio) MBI206 TGAI and ZELTO(registered trademark) from Marrone Bio Innovations, +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.MILKY SPORE POWDER (trademark) or MILKY SPORE GRANULAR (trademark) manufactured by Gabriel Laboratories + TX; Serratia entomophila (e.g., INVADE (registered trademark) manufactured by Wrightson Seeds) + TX; Serratia marcescens, especially strain SRM (acceptance number MTCC 8708) + TX; Trichoderma asperellum (TRICHODERMAX manufactured by Novozymes) + TX; Wolbachia pipientis ZAP strain (e.g., ZAP MALES (registered trademark) manufactured by MosquitoMate) + TX; Beauveria bassiana strain ATCC 74040 (e.g., NATURALIS® from Intrachem Bio Italia) + TX, Beauveria bassiana strain ATP02 (acceptance number DSM 24665), Apopka 97 (PREFERAL from SePRO) + TX, Beauveria bassiana strain GHA (acceptance number ATCC74250, e.g., BOTANIGUARD® ES and MYCONTROL-O® from Laverlam International Corporation) + TX, Metarhizium anisopliae 3213-1 (deposited under NRRL acceptance number 67074, disclosed in International Publication No. 2017 / 066094, Pioneer Hi-Bred) International) +TX, Metarhizium robertsii 15013-1 (deposited under NRRL acceptance number 67073) +TX, Metarhizium robertsii 23013-3 (deposited under NRRL acceptance number 67075) +TX, Paecilomyces lilacinus strain 251 (MELOCON, Certis, US) +TX; Cydia pomonella (codlinga) granuloma virus (GV) + TX, Helicoverpa armigera (tobacco budworm) nuclear polyhedra virus (NPV) + TX, Adoxophyes orana (apple tortrix moth) granuloma virus (GV) + TX, Spodoptera exigua (white fall armyworm) mNPV + TX, Spodoptera frugiperda (white fall 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 + TX, Rhizopogon spp.)+TX, Scleroderma spp.+TX, Streptomyces spp.+TX, Suillus spp.+TX, Agrobacterium spp.+TX, Azorhizobium caulinodans+TX, Azospirillum spp.+TX, Azotobacter spp.+TX, Bradyrhizobium spp.+TX, Gigaspora monosporum+TX; Allium sativum (NEMGUARD by Eco-Spray, BRALIC by ADAMA) + TX, Armour-Zen + TX, Artemisia absinthium + TX, Biokeeper WP + TX, Brassicaceae plant extracts, especially rapeseed powder or mustard powder + TX, Cassia nigricans + TX, Celastrus angulatus + TX, Chenopodium anthelminticum + TX, Chenopodium quinoa saponin extract derived from quinoa seeds (e.g., Heads Up plant Protectants,Heads Up® (Saponins of Quinoa) + TX (manufactured by CA), Chitin + TX, Dryopteris filix-mas + TX, Equisetum arvense + TX, Fortune Aza + TX, Fungastop + TX, Melaleuca alternifolia extract (TIMOREX GOLD, manufactured by STK) + TX, Natural Blad polypeptide extracted from lupine seeds (FRACTURE®, manufactured by FMC) + TX, Natural Blad polypeptide extracted from lupine seeds (PROBLAD®, manufactured by Certis EU) + TX, Pyrethrin + TX, Quassia amara + TX, Quercus + TX, Quillaja extract (QL AGRI 35, manufactured by BASF) + TX, REGALIA, manufactured by Marrone Bio MAXX)+TX, Requiem® insecticide+TX, Japanese knotweed (Reynoutria sachalinensis) extract (REGALLIA+TX, liania / lianodine+TX, comfrey (Symphytum officinale)+TX, tansy (Tanacetum vulgare)+TX, thymol+TX, thymol mixed with geraniol (CEDROZ, manufactured by Eden Research)+TX, thymol mixed with geraniol and eugenol (MEVALONE, manufactured by Eden Research)+TX, Triact 70+TX, TriCon+TX, nasturtium (Tropaeulum majus)+TX, stinging nettle (Urtica dioica)+TX, veratrin+TX, mistletoe (Viscum album)+TX; Mercuric oxide + TX, octylinone + TX, thiophanate-methyl + TX; MGK 264+TX, 2-(2-butoxyethoxy)ethylpiperonylate+TX, 2-isovalerylindan-1,3-dione+TX, 4-(quinoxaline-2-ylamino)benzenesulfonamide+TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohexa-2-enone+TX, acibenzolar+TX, acibenzolar-S-methyl+TX, α-bromadiolone+TX, α-chlorohydrin+TX, aluminum phosphide+TX, anthraquinone+TX, antz+TX, arsenic trioxide+TX, barium carbonate+TX, benoxacor Lu+TX, Bisthiosemi+TX, Brodifacum+TX, Bromadiolon+TX, Bromethalin+TX, Calcium cyanide+TX, Chloralose+TX, Chlorophacinone+TX, Cholecalciferol+TX, Chloquintoset (including Chloquintoset-Mexyl)+TX, Copper naphthenate+TX, Copper oxychloride+TX, Coumacrol+TX, Coumafuryl+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, γ-HCH + TX, Guazatine + TX, Guazatine acetate + TX, HCH + TX, Hydrogen cyanide + TX, Imanin + TX, Iodomethane + TX, Isoxadife N (containing isoxadiphen-ethyl) + TX, Lindan + TX, Magnesium phosphide + TX, MB-599 + TX, Mefenypr (containing mefenypr-diethyl) + TX, Metocamifen + TX, Methiocarb + TX, Methyl bromide + TX, Nerolidol + TX, Norbolmid + TX, Petroleum + TX, 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,Japanese knotweed (Reynoutria sachalinensis) extract + TX, ribavirin + TX, S421 + TX, siriloside + TX, sesamex + TX, sesamolin + TX, sodium arsenite + TX, sodium cyanide + TX, sodium fluoroacetate + TX, strychnine + TX, sulfoxide + TX, thallium sulfate + TX, thyram + TX, trimetacarb + TX, warfarin + TX, zinc naphthenate + TX, zinc phosphide + TX, thyram + TX.

[0383] 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, for example, described in U.S. Patent No. 6,919,298, and include, for example, salicylates and the commercially available SAR inducer acibenzolar-S-methyl.

[0384] The compounds of formula (I) as defined in the present invention are typically used in the form of compositions and can be applied to a planted area or plants to be treated simultaneously with or in succession to 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.

[0385] The compounds of formula (I) as defined in the present invention can be used in the form of a (fungicidal) composition for the control or protection of plant pathogenic microorganisms, comprising, as an active ingredient, at least one compound of formula (I) as defined in the present invention or at least one preferred individual compound defined in free form or in agrochemically usable salt form, and at least one of the above-mentioned auxiliary agents.

[0386] Accordingly, the present invention provides a composition, preferably a fungicidal composition, comprising at least one compound of formula (I) as defined in the present invention, an agriculturally acceptable carrier, and optionally an auxiliary agent. The agriculturally acceptable carrier is, for example, a carrier suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, in addition to the compound of formula (I) as defined in the present invention, the composition may also contain at least one or more pesticide compounds, such as additional fungicidal active ingredients.

[0387] Further aspects of the present invention relate to a method for controlling or preventing ectoparasitism by plant pathogenic or putrefactive microorganisms or organisms, particularly fungi, that are potentially harmful to humans, of plants, for example, useful plants, for example, crop plants, their reproductive materials, for example, seeds, harvested crops, for example, harvested food crops, or non-biological materials, the method comprising applying a compound of formula (I) as defined in the present invention or any of the preferred individual compounds defined above as an active ingredient to any part of a plant, a part of a plant or its habitat, its reproductive material, or non-biological material.

[0388] Control or prevention means reducing damage caused by plant pathogenic microorganisms or organisms, such as insects or especially fungi, or by putrefactive microorganisms or organisms that are potentially harmful to humans, to a level where improvement is demonstrated.

[0389] Preferred methods for controlling or preventing ectoparasitism of crop plants by plant pathogenic microorganisms, particularly fungi, include the application of a compound of formula (I) as defined in the present invention, or a pesticide composition containing at least one of the said compounds, as a foliar treatment. The frequency and amount of application will depend on the risk of infestation by the corresponding pathogen or insect. However, the compounds of formula (I) as defined in the present invention can also be introduced into the plant from the roots through the soil (osmotic translocation) by drenching the plant habitat with a liquid formulation or by applying the compound to the soil in a solid form, such as granular form (soil application). In rice cultivation, such granules can be applied to flooded paddy fields. Any compound of formula (I) as defined in the present invention can also be applied to seeds (coated) by impregnating the seeds or tubers with a liquid formulation of the fungicide or by coating them with a solid formulation.

[0390] Formulations such as compositions containing the compound of formula (I) as defined in the present invention, and optionally a solid or liquid additive or a monomer that encapsulates the compound of formula (I) as defined in the present invention, can typically be prepared by known methods by closely mixing and / or grinding the compound together with an expander, such as a solvent, a solid carrier, and optionally a surface-active compound (surfactant).

[0391] Methods of application for this composition, i.e., spraying, atomizing, scattering, brushing, powdering, diffusion, or pouring (these should be selected according to the intended purpose in general situations), methods for controlling the above-mentioned types of pathogens, and the use of the composition for controlling the above-mentioned types of pathogens are also subjects of the present invention. Typical concentration ratios are 0.1 to 1000 ppm, preferably 0.1 to 500 ppm of the active ingredient. The application rate per hectare is preferably 1 g to 2000 g of the active ingredient per hectare, more preferably 10 to 1000 g / ha, and most preferably 10 to 600 g / ha. When used as a seed drenching agent, a convenient dosage is 10 mg to 1 g of the active substance per 1 kg of seeds.

[0392] 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.

[0393] Preferably, a composition comprising a compound of formula (I) according to the present invention as defined herein is applied either preventively (meaning before the onset of disease) or therapeutically (meaning after the onset of disease).

[0394] The compositions of the present invention may be any of the conventional forms, for example, two-component systems, dry seed treatment powder (DS), seed treatment emulsion (ES), seed treatment fluid concentrate (FS), seed treatment solution (LS), seed treatment water-dispersible powder (WS), seed treatment capsule suspension (CF), seed treatment gel (GF), emulsion concentrate (EC), suspension concentrate (SC), suspension emulsion (SE), capsule suspension (CS), water-dispersible granules (WG), emulsifying granules It can be employed in the form of granules (EG), water-in-oil (EO) emulsions, oil-in-water (EW) emulsions, microemulsions (ME), oil dispersions (OD), oil-miscible flowables (OF), oil-miscible liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), industrial concentrates (TK), dispersible concentrates (DC), wettable powders (WP), or any technically feasible formulation combined with agriculturally acceptable adjuvants.

[0395] Such compositions can be produced by conventional methods, for example, by mixing an active ingredient with a suitable formulation deactivator (diluent, solvent, filler, and optionally other formulation components such as surfactants, biocides, antifreezes, spreading agents, thickeners, and compounds that provide auxiliary effects). Conventional sustained-release formulations may also be employed when sustained effectiveness over a long period is desired. In particular, formulations applied in spray form, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules, may contain surfactants, such as wetting agents and dispersants, 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.

[0396] The seed coating formulation is applied to seeds in a manner known to the present invention, utilizing the combination and diluent of the present invention in a preferred seed coating formulation form, such as an aqueous suspension or a dry powder form having good adhesion to seeds. Such seed coating formulations are known in the art. The seed coating formulation may contain a single active ingredient or a combination of active ingredients in encapsulated form, such as slow-release capsules or microcapsules.

[0397] Generally, a formulation comprises 0.01 to 90% by weight of an active agent, 0 to 20% of an agrochemically acceptable surfactant, and 10 to 99.99% of a solid or liquid inert formulation and auxiliary agents, wherein the active agent consists of at least a compound of formula (I) as defined in this invention, together with components (B) and (C), and optionally other active agents such as particularly microbial agents or preservatives. The concentrated form of the composition generally contains about 2 to 80%, preferably about 5 to 70% by weight, of the activator. The application form of the formulation may contain, for example, 0.01 to 20% by weight, preferably 0.01 to 5% by weight, of the activator. Commercial products are preferably formulated as concentrates, but end users will typically use diluted formulations.

[0398] Commercial products are preferably formulated as a concentrate, but end users typically use a diluted formulation. [Examples]

[0399] The following examples are helpful in illustrating the present invention. Certain compounds of the present invention can be distinguished from known compounds by exhibiting higher potency at lower doses, which can be confirmed by those skilled in the art using the experimental procedures outlined in the examples.

[0400] Combination example

[0401] [Table 3]

[0402] By thoroughly mixing the active ingredient with an auxiliary agent and grinding the mixture thoroughly in a suitable mill, a wettable powder can be obtained that can be diluted with water to form a suspension of the desired concentration.

[0403] [Table 4]

[0404] By thoroughly mixing the active ingredient with an auxiliary agent and then grinding the mixture thoroughly in a suitable mill, a powder can be obtained that can be used directly for seed treatment.

[0405] emulsifiable concentrate Active ingredient [compound of formula (I)] 10% Octylphenol polyethylene glycol ether 3% (4-5 mol of ethylene oxide) Calcium dodecylbenzenesulfonate 3% Castor oil polyglycol ether (ethylene oxide 35 mol) 4% Cyclohexanone 30% Xylene mixture 50%

[0406] Any desired dilution of emulsion that can be used for plant protection can be obtained from this concentrate by dilution with water.

[0407] [Table 5]

[0408] Ready-to-use powders are obtained by mixing the active ingredient with a carrier and grinding the mixture in a suitable mill. Such powders can also be used for drying and coating seeds.

[0409] Extruded granules Active ingredient [compound of formula (I)] 15% Sodium lignin sulfonate 2% Carboxymethylcellulose 1% Kaolin 82%

[0410] The active ingredient is mixed with an auxiliary agent and ground, and the mixture is moistened with water. This mixture is then extruded and dried with an airflow.

[0411] Coated granules Active ingredient [compound of formula (I)] 8% Polyethylene glycol (molecular weight 200) 3% Kaolin 89%

[0412] The finely ground active ingredient is uniformly applied to kaolin moistened with polyethylene glycol in a mixer. In this way, a dust-free coated granule is obtained.

[0413] 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%

[0414] A suspension concentrate is obtained by tightly mixing the finely ground active ingredient with an auxiliary agent. By diluting this with water, a suspension of the desired dilution can be obtained. Using such dilutions, living plants and plant propagation materials can be treated and protected from microbial ectoparasitism by spraying, pouring, or immersion.

[0415] 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%

[0416] A suspension concentrate is obtained by tightly mixing the finely ground active ingredient with an auxiliary agent. By diluting this with water, a suspension of the desired dilution can be obtained. Using such dilutions, living plants and plant propagation materials can be treated and protected from microbial ectoparasitism by spraying, pouring, or immersion.

[0417] 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 achieved. 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.

[0418] The resulting capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersant. This capsule suspension formulation contains 28% of the active ingredient. The median capsule diameter is 8-15 microns.

[0419] The resulting formulation is applied to seeds as an aqueous suspension using equipment suitable for the purpose.

[0420] Analysis method: Throughout this specification, temperatures are expressed in degrees Celsius (°C), and "mp" indicates the melting point. LC / MS stands for liquid chromatography-mass spectrometry, and the apparatus and method are described below.

[0421] Method A: Spectra were recorded using a Waters mass spectrometer with an electrospray source (Acquity QDa mass spectrometer) (polarity: positive and negative polarity switch, capillary: 0.8kV, cone range: 25V, extractor: V (no extraction voltage for QDa detector), source temperature: 120°C, desolvation temperature: 600°C, cone gas flow rate: 50L / h, desolvation gas flow rate: 1000L / h, mass range: 110~850Da) and a Waters Acquity UPLC: quaternary solvent vent manager, heated column compartment, and diode array detector. Column: Acquity UPLC HSS T3 C18, 1.8 μm, 30 × 2.1 mm, Temperature: 40°C, DAD wavelength range (nm): 200~400, Solvent gradient: A = Water + 5% Acetonitrile + 0.1% HCOOH, B = Acetonitrile + 0.05% HCOOH: Gradient: 10% B for 0 min; 10~50% B for 0~0.2 min; 50~100% B for 0.2~0.6 min; 100% B for 0.6~1.3 min; 100~10% B for 1.3~1.4 min; 10% B for 1.4~1.6 min; Flow rate (mL / min): 0.6.

[0422] Method B: Spectra were recorded using a Waters Corporation mass spectrometer (SQD, SQDII, or QDA single quadrupole mass spectrometer) equipped with an electrospray source (polarity: cations and anions), capillary voltage: 0.8~3.00kV, cone voltage: 5~30V, source temperature: 120~150°C, desolvation temperature: 350~600°C, cone gas flow rate: 50~150 l / h, desolvation gas flow rate: 650~1000 l / h, mass range: 110~950 Da, and a Waters Corporation Acquity UPLC: binary pump, heated column compartment, diode array detector, and ELSD. Column: Waters ULC 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 at constant composition for 0.2 min, then 10~100% B for 1.0 min, 100% B at constant composition for 0.2 min, 100~10% B for 0.05 min, 10% B at constant composition for 0.05 min.

[0423] Method C: Spectra were recorded using a mass spectrometer from Agilent with multimode electrospray and APCI (single quadrupole mass spectrometer) (polarity: cations and anions), capillary: 4.00kV, corona current: 4.0μA, charging voltage: 2.00kV, nitrogen gas flow rate: 12.0L / min, nebulizer pressure: 40psig, mass range: 100~1000m / z), dry gas temperature: 250℃, vaporizer temperature: 200℃, and a Waters UPLC: quaternary pump, heated column compartment, and tunable wavelength detector. Column: X-Bridge BEH C18, 2.5μm (2.1×50mm), column temperature: ambient, wavelength (nm): 215nm, gradient: A = 0.05% TFA in water, 0.05% TFA in acetonitrile. Gradient: Time / %B: 0 / 5, 1 / 5, 5 / 70, 7 / 95, 8.5 / 95, 8.6 / 5, 10 / 5; Flow rate: 0.6 mL / min.

[0424] Table A below summarizes the compounds of formula (I): - LC-MS data, e.g., retention time (RT), [M+H] + , - Type of method, and / or - Melting point (mp).

[0425] [Table 6-1]

[0426] [Table 6-2]

[0427] [Table 6-3]

[0428] [Table 6-4]

[0429] [Table 6-5]

[0430] Example 1: Preparation of methyl N-[5-[6-[(4-fluoro-3-methylphenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-b]pyridazin-3-yl]-2-pyridyl]carbamate (Compound 1) [ka] (Compound 1) Step A: Preparation of 6-chloro-8-methylimidazo[1,2-b]pyridazine (compound X-1) [ka] (Compound X-1) To a solution of 6-chloro-4-methylpyridazine-3-amine (5.00 g, 34.1 mmol, 1.00 equivalent) in isopropanol (100 mL), bromoacetaldehyde diethyl acetal (14.7 mL, 92.2 mmol, 2.70 equivalents) was added. The reaction mixture was stirred under reflux for 3 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 to obtain 6-chloro-8-methylimidazo[1,2-b]pyridazine. LC-MS (Method A): Rt 0.35 min, m / z=168 / 170(M+H) + . 1 H-NMR(400MHz,CDCl3,ppm)δ=7.81-7.84(m,1H),7.63-7.67(m,1H),6.81-6.84(m,1H),2.57-2.61(m,3H)

[0431] Step B: Preparation of N-(4-fluoro-3-methylphenyl)-N,8-dimethylimidazo[1,2-b]pyridazine-6-carboxamide [ka] A mixture of 6-chloro-8-methylimidazo[1,2-b]pyridazine (compound X-1, 0.700 g, 4.17 mmol, 1.00 equivalent), 4-fluoro-N,3-dimethylaniline (0.58 g, 4.2 mmol, 1.0 equivalent), triethylamine (0.88 mL, 16 mmol, 1.1 equivalent), bis(benzonitrile)palladium chloride (0.246 g, 0.420 mmol, 0.100 equivalent), and 4,5-bis(diphenylphosphin)-9,9-dimethylxanthene (0.168 g, 0.420 mmol, 0.100 equivalent) in toluene (10.4 mL) in a high-pressure vessel was flushed with nitrogen. The vial was pressurized with nitrogen, and then with CO gas. The reaction mixture was stirred at 110°C for 12 hours. The reaction mixture was filtered through Celite and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain N-(4-fluoro-3-methylphenyl)-N,8-dimethylimidazo[1,2-b]pyridazine-6-carboxamide. LC-MS (Method A): Rt 1.13 min, m / z=297(M+H) + . 1 H-NMR(400MHz,CDCl3,ppm)δ=7.68(br s,2H),7.04(br s,2H),6.81-6.91(m,2H),3.48(s,3H),2.61(s,3H),2.15-2.20(m,3H).

[0432] Step C: Preparation of 3-bromo-N-(4-fluoro-3-methylphenyl)-N,8-dimethylimidazo[1,2-b]pyridazine-6-carboxamide [ka] A solution of N-(4-fluoro-3-methyl-phenyl)-N,8-dimethyl-imidazo[1,2-b]pyridazine-6-carboxamide (0.400 g, 1.34 mmol, 1.00 equivalent) and N-bromosuccinimide (0.268 g, 1.47 mmol, 1.10 equivalent) in acetonitrile (5.36 mL) was stirred at room temperature for 16 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over 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-fluoro-3-methyl-phenyl)-N,8-dimethyl-imidazo[1,2-b]pyridazine-6-carboxamide. LC-MS (Method A): Rt 1.13 min, m / z=377 / 379(M+H) + . 1 H-NMR(400MHz,CDCl3,ppm)δ=7.55-7.65(m,1H),7.13-7.27(m,1H),7.04(br d,J=4.75Hz,1H),6.81-6.85(m,1H),6.78(br d,J=8.88Hz,1H),3.42(s,3H),2.57(s,3H),2.14(s,3H)

[0433] Step D: Preparation of methyl N-[5-[6-[(4-fluoro-3-methylphenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-b]pyridazin-3-yl]-2-pyridyl]carbamate (compound 1) 3-bromo-N-(4-fluoro-3-methylphenyl)-N,8-dimethylimidazo[1,2-b]pyridazine-6-carboxamide (0.200 g, 0.42 mmol, 1.00 equivalent) and methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (0.1) in acetonitrile (3.39 mL) To a mixture of 6 g, 0.55 mmol, 1.30 equivalents of (2-(2'-amino-1,1'-biphenyl)) and sodium carbonate (0.13 g, 1.27 mmol, 3.00 equivalents), chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) (0.034 g, 0.042 mmol, 0.10 equivalents) was added. The reaction mixture was degassed with argon and then stirred in a microwave at 80°C for 2 hours. After cooling to room temperature, the reaction mixture was filtered through a Celite pad and washed with methanol. The filtrate was concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain methyl N-[5-[6-[(4-fluoro-3-methylphenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-b]pyridazin-3-yl]-2-pyridyl]carbamate. LC-MS (Method A): Rt 1.07 min, m / z=449(M+H) + . 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=10.41(s,1H),8.63(s,1H),8.20(s,1H),7.94-7.96(m,2H),7.41-7.43 (m,2H),6.92-6.97(m,2H),3.72(s,3H),3.44(s,3H),2.61(s,3H),2.12(m,3H).

[0434] Example 2: Preparation of methyl N-[5-[6-(6-fluoro-3,4-dihydro-2H-quinoline-1-carbonyl)-8-methylimidazo[1,2-b]pyridazine-3-yl]-2-pyridyl]carbamate (Compound 2) [ka] (Compound 2) Step A: Preparation of (6-fluoro-3,4-dihydro-2H-quinoline-1-yl)-(8-methylimidazo[1,2-b]pyridazine-6-yl)methanone [ka] A mixture of 6-chloro-8-methylimidazo[1,2-b]pyridazine (compound X-1) (0.500 g, 2.98 mmol, 1.00 equivalent), 6-fluoro-1,2,3,4-tetrahydroquinoline (0.47 g, 3.1 mmol, 1.1 equivalent), triethylamine (0.624 mL, 4.47 mmol, 1.50 equivalent), bis(benzonitrile)palladium chloride (0.120 g, 0.298 mmol, 0.100 equivalent), and 4,5-bis(diphenylphosphin)-9,9-dimethylxanthene (0.176 g, 0.300 mmol, 0.100 equivalent) in toluene (7.45 mL) in a high-pressure vessel was flushed with nitrogen. The vial was pressurized with nitrogen and then with CO gas. The reaction mixture was stirred at 110°C for 6 hours. The reaction mixture was filtered through Celite and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain (6-fluoro-3,4-dihydro-2H-quinoline-1-yl)-(8-methylimidazo[1,2-b]pyridazine-6-yl)methanone. LC-MS (Method A): Rt 1.06 min, m / z=311(M+H) + .

[0435] Step B: Preparation of (3-bromo-8-methylimidazo[1,2-b]pyridazin-6-yl)-(6-fluoro-3,4-dihydro-2H-quinoline-1-yl)methanone [ka] A solution of (6-fluoro-3,4-dihydro-2H-quinoline-1-yl)-(8-methylimidazo[1,2-b]pyridazin-6-yl)methanone (0.450 g, 1.23 mmol) and N-bromosuccinimide (0.246 g, 1.36 mmol, 1.10 equivalents) in acetonitrile (4.93 mL) was stirred at room temperature for 1 hour. The reaction mixture was poured into 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-bromo-8-methylimidazo[1,2-b]pyridazin-6-yl)-(6-fluoro-3,4-dihydro-2H-quinoline-1-yl)methanone. LC-MS (Method A): Rt 1.18 min, m / z=389 (M+H) + .

[0436] Step C: Preparation of methyl N-[5-[6-(6-fluoro-3,4-dihydro-2H-quinoline-1-carbonyl)-8-methylimidazo[1,2-b]pyridazin-3-yl]-2-pyridyl]carbamate (compound 2) (3-bromo-8-methylimidazo[1,2-b]pyridazin-6-yl)-(6-fluoro-3,4-dihydro-2H-quinoline-1-yl)methanone (0.118 g, 0.300 mmol, 1.00 equivalent) in acetonitrile (2.42 mL), methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate ( To a mixture of 0.116 g, 0.390 mmol, 1.30 equivalents of chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) (0.024 g, 0.03 mmol, 0.10 equivalents) and sodium carbonate (0.096 g, 0.91 mmol, 3.00 equivalents), chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) (0.024 g, 0.03 mmol, 0.10 equivalents) was added. The reaction mixture was degassed with argon and then stirred in a microwave at 80°C for 2.5 hours. After cooling to room temperature, the reaction mixture was filtered through a Celite pad and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (cyclohexane / ethyl acetate) to obtain methyl N-[5-[6-(6-fluoro-3,4-dihydro-2H-quinoline-1-carbonyl)-8-methylimidazo[1,2-b]pyridazine-3-yl]-2-pyridyl]carbamate as a yellow solid. LC-MS (Method A): Rt 1.12 min, m / z=461(M+H) + . 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=10.38(s,1H),8.60-8.70(m,1H),8.26(s,1H),7.85(br d,J=8.44Hz,2H),7.44-7.46(m,1H),7.11-7.17(m,2H),6.74-6.87(m,1H),3.86(br t,J=6.24Hz,2H),3.71(s,3H),2.87(t,J=6.54Hz,2H),2.66(s,3H),1.95-2.05(m,2H).

[0437] Example 3: Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-b]pyridazin-3-yl]-2-pyridyl]carbamate (compound 4) [ka] (Compound 4) Step A: Preparation of N-(4-fluoro-3-methoxyphenyl)-N,8-dimethylimidazo[1,2-b]pyridazine-6-carboxamide [ka] A mixture of 6-chloro-8-methylimidazo[1,2-b]pyridazine (compound X-1, 0.500 g, 2.98 mmol, 1.00 equivalent), 4-fluoro-3-methoxy-N-methylaniline (0.486 g, 3.13 mmol, 1.05 equivalent), triethylamine (0.627 mL, 4.47 mmol, 1.50 equivalent), bis(benzonitrile)palladium chloride (0.120 g, 0.30 mmol, 0.10 equivalent), and 4,5-bis(diphenylphosphin)-9,9-dimethylxanthene (0.176 g, 0.30 mmol, 0.10 equivalent) in toluene (7.45 mL) in a high-pressure vessel was flushed with nitrogen. The vial was pressurized with nitrogen, and then with CO gas. The reaction mixture was stirred at 110°C for 6 hours. The reaction mixture was filtered through Celite 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,8-dimethylimidazo[1,2-b]pyridazine-6-carboxamide. LC-MS (Method A): Rt 0.96 min, m / z=315(M+H) + . 1 H-NMR(400MHz,CDCl3,ppm)δ=7.68(br s,2H),7.01(br s,1H),6.85-6.94(m,1H),6.75-6.84(m,1H),6.64(br s,1H),3.78(br s,3H),3.50(s,3H),2.60(br s,3H).

[0438] Step B: Preparation of 3-bromo-N-(4-fluoro-3-methoxyphenyl)-N,8-dimethylimidazo[1,2-b]pyridazine-6-carboxamide [ka] A solution of N-(4-fluoro-3-methoxyphenyl)-N,8-dimethylimidazo[1,2-b]pyridazine-6-carboxamide (0.662 g, 2.11 mmol, 1.00 equivalent) and N-bromosuccinimide (0.412 g, 2.32 mmol, 1.10 equivalent) in acetonitrile (8.42 mL) was stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to obtain 3-bromo-N-(4-fluoro-3-methoxyphenyl)-N,8-dimethylimidazo[1,2-b]pyridazine-6-carboxamide. LC-MS (Method A): Rt 1.08 min, m / z=393 / 395(M+H) + .

[0439] Step C: Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-b]pyridazin-3-yl]-2-pyridyl]carbamate (compound 4) 3-bromo-N-(4-fluoro-3-methoxyphenyl)-N,8-dimethylimidazo[1,2-b]pyridazine-6-carboxamide (0.62 g, 1.6 mmol, 1.00 equivalent) and methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (0.60) in acetonitrile (12.6 mL) To a mixture of 6 g, 2.05 mmol, 1.30 equivalents of (2-(2'-amino-1,1'-biphenyl)) and sodium carbonate (0.501 g, 4.73 mmol, 3.00 equivalents), chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) (0.13 g, 0.15 mmol, 0.10 equivalents) was added. The reaction mixture was degassed with argon and then stirred in a microwave at 80°C for 2.5 hours. After cooling to room temperature, the reaction mixture was filtered through a Celite pad and washed with methanol. The filtrate was washed with water and then 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-[6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-b]pyridazin-3-yl]-2-pyridyl]carbamate as a yellow solid. LC-MS (Method A): Rt 1.05 min, m / z=465(M+H) + . 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=10.39(s,1H),8.71-8.60(s,1H),8.21(s,1H),7.94(br s,2H),7.42(s,1H)7.32(br d,J=7.20Hz,1H),6.95-7.05(m,1H),6.75-6.60(m,1H),3.68-3.80(m,6H),3.48(s,3H),2.54-2.68(m,3H).

[0440] Example 4: Preparation of methyl N-[5-[6-[(4-fluoro-3-methylphenyl)-methyl-carbamoyl]imidazo[1,2-b]pyridazin-3-yl]-2-pyridyl]carbamate (compound 7) [ka] (Compound 7) Chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) (0.089 g, 0.11 mmol, 0.10 equivalent) was added to a mixture of 3-bromo-N-(4-fluoro-3-methyl-phenyl)-N-methyl-imidazo[1,2-b]pyridazine-6-carboxamide (0.400 g, 1.10 mmol, 1.00 equivalent), 2-methoxycarbonylaminopyridine-5-boronic acid pinacol ester (0.419 g, 1.43 mmol, 1.30 equivalent), and sodium carbonate (0.350 g, 3.30 mmol, 3.00 equivalent) in acetonitrile (8.81 mL). The reaction mixture was degassed with argon and then stirred in microwaves at 100°C for 2 hours. After cooling to room temperature, the reaction mixture was filtered through a Celite pad and washed with methanol. The filtrate was concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (ethyl acetate / methanol) to obtain methyl N-[5-[6-[(4-fluoro-3-methylphenyl)-methyl-carbamoyl]imidazo[1,2-b]pyridazin-3-yl]-2-pyridyl]carbamate as a yellow solid. LC-MS (Method A): Rt 1.02 min, m / z=435(M+H) + . 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=2.11(br s,3H),3.34(s,3H),3.72(s,3H),6.80-7.02(m,2H),7.49(d,J=9.38Hz,1H),7.50(d,1H),7.96(br s,2H),8.27(br s,2H),8.66(s,1H),10.41(s,1H)

[0441] Example 5: Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-b]pyridazin-3-yl]-2-pyridyl]carbamate (compound 8) [ka] (Compound 8) Step A: Preparation of methyl 3-bromoimidazo[1,2-b]pyridazine-6-carboxylate [ka] A solution of methylimidazo[1,2-b]pyridazine-6-carboxylate (0.500 g, 2.76 mmol, 1.00 equivalent) and N-bromosuccinimide (0.547 g, 3.04 mmol, 1.10 equivalent) in acetonitrile (7 mL) was stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to obtain methyl 3-bromoimidazo[1,2-b]pyridazine-6-carboxylate. LC-MS (Method A): Rt 0.96 min, m / z=256 / 258(M+H) + . 1 H-NMR(400MHz,CDCl3,ppm)δ=4.08(s,3H),7.83(d,J=9.41Hz,1H),7.93(s,1H),8.06(d,J=9.41Hz,1H)

[0442] Step B: Preparation of 3-bromoimidazo[1,2-b]pyridazine-6-carboxylic acid [ka] To a solution of methyl 3-bromoimidazo[1,2-b]pyridazine-6-carboxylate (0.700 g, 2.00 mmol, 1.00 equivalent) in water (4 mL) and methanol (10 mL), lithium hydroxide (0.100 g, 3.00 mmol, 1.10 equivalent) was added. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure and adjusted to pH 4 with citric acid. The resulting solid was filtered off and dried under reduced pressure to obtain 3-bromoimidazo[1,2-b]pyridazine-6-carboxylic acid. LC-MS (B method): Rt 0.27 min, m / z=242 / 244 (M+H) + . 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=7.78(d,J=9.51Hz,1H),8.07(br s,1H),8.30(d,J=9.51Hz,1H),13.98 -14.27(m,1H)

[0443] Step C: Preparation of 3-bromo-N-(4-fluoro-3-methoxyphenyl)-N-methylimidazo[1,2-b]pyridazine-6-carboxamide [ka] To a solution of 3-bromoimidazo[1,2-b]pyridazine-6-carboxylic acid (0.540 g, 2.12 mmol, 1.00 equivalent), 4-fluoro-3-methoxy-N-methylaniline (0.450 g, 2.75 mmol, 1.30 equivalent), and N-ethyl-N-isopropyl-propan-2-amine (1.146 mL, 3.00 mmol, 6.36 equivalents) in acetonitrile (10.6 mL), 50% 1-propanephosphonic anhydride (1.33 mL, 4.24 mmol, 2.00 equivalent) in ethyl acetate was added. The reaction mixture was stirred at room temperature 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-fluoro-3-methoxyphenyl)-N-methylimidazo[1,2-b]pyridazine-6-carboxamide as a pale yellow solid. LC-MS (B method): Rt 1.06 min, m / z=379 / 381(M+H) + . 1 H-NMR(400MHz,CDCl3,ppm)δ=8.16(br d,J=9.51Hz,1H),7.92(s,1H),7.45(br d,J=9.26Hz,1H),7.27(br d,J=6.88Hz,1H),7.04(br t,J=10.07Hz,1H),6.71-6.83(m,1H),3.74(s,3H),3.44(s,3H)

[0444] Step D: Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-b]pyridazin-3-yl]-2-pyridyl]carbamate (compound 8) 3-bromo-N-(4-fluoro-3-methoxyphenyl)-N-methylimidazo[1,2-b]pyridazine-6-carboxamide (0.200 g, 0.527 mmol, 1.00 equivalent), methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate in acetonitrile (4.22 mL) and water (2.11 mL) To a mixture of 0.220 g, 0.791 mmol, 1.500 equivalents of chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) (0.043 g, 0.052 mmol, 0.10 equivalents) and sodium carbonate (0.167 g, 1.58 mmol, 3.00 equivalents), chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) (0.043 g, 0.052 mmol, 0.10 equivalents) was added. The reaction mixture was degassed with argon and then stirred in a microwave at 100°C for 1 hour. After cooling to room temperature, the reaction mixture was filtered through a Celite pad and washed with methanol. The filtrate was concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (ethyl acetate / methanol) to obtain methyl N-[5-[6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-b]pyridazin-3-yl]-2-pyridyl]carbamate as a yellow solid. LC-MS (Method A): Rt 1.06 min, m / z=451(M+H) + . 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=3.45-3.52(m,3H),3.74(br s,6H),6.76(br s,1H),6.88-7.14(m,1H),7.33(br d,J=6.24Hz,1H),7.51(br d,J=9.05Hz,1H),7.87-8.07(m,2H),8.18-8.35(m,2H),8.70(br s,1H),10.31-10.52(m,1H). 19 F NMR (377MHz, DMSO-d 6 δ = -136.91 (s, 1 F) (ppm)

[0445] Example 6: Preparation of 3-(4-acetamidophenyl)-N-(4-chlorophenyl)-N-methylimidazo[1,2-a]pyrimidine-6-carboxamide (compound 9) [ka] (Compound 9) Step A: Preparation of ethylimidazo[1,2-a]pyrimidine-6-carboxylate [ka] To a solution of ethyl 2-aminopyrimidine-5-carboxylate (2.00 g, 12.0 mmol) in ethanol (15.0 mL) under argon, 2-chloroacetaldehyde (4.70 g, 59.8 mmol, 5.00 equivalents) was added. The mixture was stirred at 80°C for 16 hours. The reaction mixture was concentrated under reduced pressure, then diluted with aqueous sodium bicarbonate solution, and then extracted with 10% methanol in dichloromethane. The organic layer was washed with water, then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified using a silica gel cartridge (dichloromethane / methanol) to obtain ethylimidazo[1,2-a]pyrimidine-6-carboxylate as an off-white solid. 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=1.35(d,3H),4.39(q,2H),7.83(s,1H),8.05(s,1H),8.90(s,1H),9.68(s,1H).

[0446] Step B: Preparation of ethyl 3-bromoimidazo[1,2-a]pyrimidine-6-carboxylate [ka] To a stirred solution of ethylimidazo[1,2-a]pyrimidine-6-carboxylate (20.0 mg, 0.105 mmol) in dichloromethane (2 mL), N-bromosuccinimide (27.9 mg, 0.157 mmol, 1.5 equivalents) was added at room temperature. The resulting reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure and then purified using a silica gel cartridge (hexane / ethyl acetate) to obtain ethyl 3-bromoimidazo[1,2-a]pyrimidine-6-carboxylate as an off-white solid. 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=1.37(d,3H),4.41(q,2H),8.05(s,1H),8.95(d,1H),9.05(d,1H).

[0447] Step C: Preparation of ethyl 3-(4-acetamidophenyl)imidazo[1,2-a]pyrimidine-6-carboxylate [ka] To a stirred solution of ethyl 3-bromoimidazo[1,2-a]pyrimidine-6-carboxylate (300 mg, 1.09 mmol) in toluene (2.0 mL) and ethanol (1.0 mL), (4-acetamidophenyl)boronic acid (390 mg, 2.18 mmol, 2 equivalents), tris(o-tolyl)phosphine (36.4 mg, 0.120 mmol, 0.11 equivalents), and a solution of potassium fluoride (158 mg, 2.72 mmol, 2.50 equivalents) in water (0.50 mL) were added at room temperature. The mixture was degassed with argon for 2 minutes. Then, tris(dibenzylideneacetone)dipalladium(0) (62.6 mg, 0.109 mmol, 0.10 equivalents) was added. The mixture was further degassed with argon for 1 minute and irradiated in microwaves at 100°C for 20 minutes. The reaction mixture was cooled to room temperature and filtered through a Celite pad. The filtrate was diluted with ethyl acetate and washed with water. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude mixture was purified using a silica gel cartridge (hexane / ethyl acetate) to obtain ethyl 3-(4-acetamidophenyl)imidazo[1,2-a]pyrimidine-6-carboxylate as a pale yellow solid. 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=1.35(t,3H),2.07(s,3H),4.39(q,2H),7.70(m,2H),7.92(m,2H),8.38(s,1H),8.87(s,1H),9.58(m,1H),10.1(s,1H)

[0448] Step D: Preparation of 3-(4-acetamidophenyl)imidazo[1,2-a]pyrimidine-6-carboxylic acid [ka] Lithium hydroxide hydrate (13.6 mg, 0.323 mmol, 3 equivalents) was added to a stirred solution of ethyl 3-(4-acetamidophenyl)imidazo[1,2-a]pyrimidine-6-carboxylate (40.0 mg, 0.108 mmol) in tetrahydrofuran (1.0 mL) and water (1.0 mL). The mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure and then diluted with ethyl acetate and water. The aqueous layer was acidified with 2N HCl solution. The aqueous layer was extracted with dichloromethane. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to obtain 3-(4-acetamidophenyl)imidazo[1,2-a]pyrimidine-6-carboxylic acid as a pale yellow solid. 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=2.03(s,3H),7.10-7.30(m,1H),7.60-7.70(m,2H),7.85-7.95(m,2H),8.27(s,1H),8.88(s,1H),9.12(s,1H)

[0449] Step E: Preparation of 3-(4-acetamidophenyl)-N-(4-chlorophenyl)-N-methylimidazo[1,2-a]pyrimidine-6-carboxamide (compound 9) To a stirred solution of 3-(4-acetamidophenyl)imidazo[1,2-a]pyrimidine-6-carboxylic acid (30.0 mg, 0.0810 mmol) in N,N-dimethylformamide (4.00 mL), 4-chloro-N-methylaniline (11.5 mg, 0.0810 mmol, 1.00 equivalent) and [dimethylamino(triazolo[4,5-b]pyridine-3-yloxy)methylene]-dimethyl-ammonium hexafluorophosphate (46.2 mg, 0.122 mmol, 1.50 equivalent), followed by N,N-diisopropylethylamine (0.0282 mL, 0.162 mmol, 2.00 equivalent), were added at room temperature. The mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure and then purified by reverse-phase combiflash chromatography (water / acetonitrile) to obtain 3-(4-acetamidophenyl)-N-(4-chlorophenyl)-N-methylimidazo[1,2-a]pyrimidine-6-carboxamide as a yellow solid. LC-MS (Method C): Rt 6.51 min, m / z=420(M+H) + . 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=2.05(s,3H),3.42(s,3H),7.33-7.42(m,4H),7.65-7.70(m,2H) ,7.85-7.92(m,2H),8.18(m,1H),8.29(s,1H),8.88(s,1H),9.12(m,1H)

[0450] Example 7: Preparation of 3-(4-acetamidophenyl)-N-(4-chlorophenyl)-N-methylimidazo[1,2-b]pyridazine-6-carboxamide (compound 10) [ka] (Compound 10) Step A: Preparation of ethylimidazo[1,2-b]pyridazine-6-carboxylate [ka] To a solution of ethyl 6-aminopyridazine-3-carboxylate (CAS 98548-01-7, 1.20 g, 7.18 mmol) in ethanol (20.0 mL), 50.0% chloroacetaldehyde in water (7.50 mL, 35.9 mmol, 5.00 equivalents) was added. The reaction mixture was stirred at 80°C for 16 hours. The reaction mixture was concentrated under reduced pressure, and the crude residue was purified using a silica gel cartridge (dichloromethane / methanol) to obtain ethylimidazo[1,2-b]pyridazine-6-carboxylate as an off-white solid. 1 H-NMR(400MHz,CDCl3,ppm)δ=1.48(t,3H),4.54(q,2H),7.79(d,1H),7.92(s,1H),8.08(d,1H),8.16(s,1H)

[0451] Step B: Preparation of ethyl 3-bromoimidazo[1,2-b]pyridazine-6-carboxylate [ka] To an ice-cold solution of ethylimidazo[1,2-b]pyridazine-6-carboxylate (0.300 g, 1.57 mmol) in dimethylformamide (5.00 mL), N-bromosuccinimide (0.307 g, 1.73 mmol, 1.10 equivalents) was added. The reaction mixture was stirred at 0°C for 30 minutes. The reaction mixture was poured into 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 (dichloromethane / methanol) to obtain ethyl 3-bromoimidazo[1,2-b]pyridazine-6-carboxylate as an off-white solid. 1 H-NMR(400MHz,CDCl3,ppm)δ=1.49(t,3H),4.54(q,2H),7.80(d,1H),7.91(s,1H),8.07(d,1H)

[0452] Step C: Preparation of ethyl 3-(4-acetamidophenyl)imidazo[1,2-b]pyridazine-6-carboxylate [ka] To a solution of ethyl 3-bromoimidazo[1,2-b]pyridazine-6-carboxylate (0.210 g, 0.778 mmol) in toluene (6.00 mL) and ethanol (4.00 mL), 4-acetamidophenylboronic acid (0.278 g, 1.56 mmol, 2.00 equivalents), tris(o-tolyl)phosphine (0.047 mg, 0.16 mmol, 0.20 equivalents), potassium fluoride (2.0 M in water, 2.5 mL, 1.94 mmol, 2.50 equivalents), and tris(dibenzylideneacetone)dipalladium(0) (71.2 mg, 0.0778 mmol, 0.10 equivalents) were added. The reaction mixture was stirred in a microwave at 110°C for 15 minutes. The reaction mixture was filtered through a Celite pad and washed with methanol. The filtrate was washed with water, then brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by reverse-phase combiflash chromatography (10-100% acetonitrile in water) to obtain ethyl 3-(4-acetamidophenyl)imidazo[1,2-b]pyridazine-6-carboxylate as a pale yellow solid. 1 H-NMR(400MHz,CDCl3,ppm)δ=1.48(t,3H),2.11(s,3H),4.52(q,2H),7.70(d,2H),7.78(d,1H),8.09(d,1H),8.15-8.21(m,3H)

[0453] Step D: Preparation of 3-(4-acetamidophenyl)imidazo[1,2-b]pyridazine-6-carboxylic acid [ka] To a solution of ethyl 3-(4-acetamidophenyl)imidazo[1,2-b]pyridazine-6-carboxylate (0.02 g, 0.0617 mmol, 1.00 equivalent) in tetrahydrofuran (0.50 mL), water (0.50 mL), and methanol (0.20 mL), lithium hydroxide hydrate (0.0077 g, 0.19 mmol, 3.0 equivalent) was added. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, dissolved in water, and the pH was adjusted to pH 2 using a 1.0 N hydrogen chloride solution. The resulting precipitate was washed with cold water and dried under reduced pressure to obtain 3-(4-acetamidophenyl)imidazo[1,2-b]pyridazine-6-carboxylic acid as an off-white solid. 1 H-NMR (400MHz, DMSO-d 6 ,ppm)δ=2.09(s,3H),7.71-7.78(m,3H),8.18(s,2H),8.31(d,1H),8.41(s,1H)

[0454] Step E: Preparation of 3-(4-acetamidophenyl)-N-(4-chlorophenyl)-N-methylimidazo[1,2-b]pyridazine-6-carboxamide (compound 10) To a solution of 3-(4-acetamidophenyl)imidazo[1,2-b]pyridazine-6-carboxylic acid (0.030 g, 0.10 mmol), 4-chloro-N-methylaniline (0.0143 g, 0.101 mmol, 1.00 equivalent), and triethylamine (0.030 g, 0.304 mmol, 3.00 equivalent) in dichloromethane (3.00 mL), 1-propanephosphonic acid cyclic anhydride (50% in ethyl acetate, 0.193 g, 0.304 mmol, 3.00 equivalent) was added. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by reverse-phase combiflash chromatography (10-100% acetonitrile in water) to obtain 3-(4-acetamidophenyl)-N-(4-chlorophenyl)-N-methyl-1,8a-dihydroimidazo[1,2-b]pyridazine-6-carboxamide as a pale yellow solid. 1 H-NMR(400MHz,CDCl3,ppm)δ=2.25(s,3H),3.52(s,3H),7.01-7.08(m,2H),7.15- 7.20(m,2H),7.22-7.33(m,2H),7.40-7.49(m,2H),7.55-7.61(m,2H),8.00(d,2H)

[0455] Biological examples: The fungicidal activity of the compound of the present invention was tested as follows.

[0456] Phytophthora infestans / Tomato / Leaf blight prevention agent (leaf blight) Tomato leaf fragments are placed on agar in a multi-well plate (24-well type), and a test compound diluted with water is sprayed onto them. One day after application, a suspension of fungal spores is inoculated onto the leaf fragments. The inoculated leaf fragments are incubated in a climate cabinet at 16°C and 75% rh under a light environment of 24 hours in darkness, followed by 12 hours of light / 12 hours of darkness. The activity of the compound is evaluated as the disease control rate compared to the untreated leaf fragments when an appropriate level of disease damage appears on the untreated test leaf fragments (5-7 days after application).

[0457] The following compounds, at 200 ppm, provided at least 80% control of Phytophthora infestans, which exhibited widespread disease development, compared to an untreated control under identical conditions: 2, 3, 4, 8.

[0458] Plasmopara viticola / Grape / Leaf blight preventative (leaf blight) Grapevine leaflets are placed on agar in a multi-well plate (24-well type), and a test compound diluted with water is sprayed onto them. One day after application, a fungal spore suspension is inoculated onto the leaflets. The inoculated leaflets are incubated in a climate cabinet under a 12-hour light / 12-hour darkness environment at 19°C and 80% rh. The activity of the compound is evaluated as the disease control rate compared to the untreated leaflets when an appropriate level of disease damage appears on the untreated test leaflets (6-8 days after application).

[0459] The following compounds, at 200 ppm, provided at least 80% control of Plasmopara viticola compared to an untreated control that showed widespread disease development under identical conditions: 1, 3, 4, 8.

[0460] Pythium ultimum / Liquid culture (Seedling blight) Newly grown fungal mycelial fragments and oospores from liquid culture are directly mixed into a nutrient medium (PDB potato dextrose medium). After adding a (DMSO) solution of the test compound to a microtiter plate (96-well type), the nutrient medium containing the fungal mycelial / 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.

[0461] The following compounds, at 20 ppm, provided at least 80% control of Pythium ultimum when compared to an untreated control that exhibited widespread disease development under identical conditions. 4,8.

Claims

1. Compound of formula (I) 【Chemistry 1】 (wherein Z is O or S, preferably Z is O; Each A 1 is N, or one A 1 is N and one A 1 CR 1 And; preferably, one A 1 is N and one A 1 CR 1 And; R 1 is independently selected from hydrogen, hydroxy, halogen, CN, C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 alkoxy-C 1-6 alkyl, C 3-6 cycloalkyl-C 1-4 alkyl, C 1-6 alkylsulfanyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 alkoxy, amino, and -NHC(O)C 1-6 alkyl; A 2 CR is independent 2 or N, provided there are three or fewer A's. 2 is N, preferably two or fewer A 2 is N, preferably one or less A 2 is N, and more preferably four A 2 CR 2 Provided that; R 2 These are 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, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, 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 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, wherein each of the C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkoxy, C 2-6 alkenyl, C 2-6 alkynyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 alkyl, C 1-6 alkylsulfanyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, amino, C 1-6 alkylamino, diC 1-6 -alkylamino, and C 3-6 each of the cycloalkylamino groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxy, and CN; A 4 is CH or N; R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl, diC 1-6 Alkylaminocarbonyl-C 1-6 Selected from alkyl and CN, where C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 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; Here, A 3 and R 4 They may optionally come together to form a ring, preferably a 5- to 8-membered heterocycle, more preferably a 6-membered heterocycle; R 5 C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, diC 1-6 Alkylamino, C 1-6 Alkoxyaminos and C 1-6 Alkyl C 1-6 Selected from alkoxyaminos, where C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, diC 1-6 Alkylamino, C 1-6 Alkoxyaminos and C 1-6 Alkyl C 1-6 Each alkoxyamino group may be optionally substituted with one to three substituents independently selected from halogens and CNs. or its salt or N-oxide.

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

3. R 1 is hydrogen and C 1-6 A compound according to claim 1 or 2, independently selected from alkyl groups.

4. R 2 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, and C 1-6 Independently selected from alkylcarbonyls, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, and C 1-6 The compound according to any one of claims 1 to 3, wherein each alkylcarbonyl group may be optionally substituted with one to three substituents independently selected from halogen, hydroxyl, and CN.

5. R 3 is hydroxy, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 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 cycloalkylamino, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 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 A 3 The compound according to any one of claims 1 to 5, wherein is N. 【Request Item 7】 【Chemistry 2】 teeth 【Transformation 3】 Preferably three A 2 CR 2 A 3 CR 3 The compound according to any one of claims 1 to 5. 【Request Item 8】 【Chemistry 4】 teeth 【Transformation 5】 Preferably three A 2 CR 2 A 3 CR 3 The compound according to any one of claims 1 to 5.

9. The four A's 2 CR 2 A 3 CR 3 The compound according to any one of claims 1 to 5. 【Request Item 10】 【Chemistry 6】 teeth 【Transformation 7】 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, selected from alkyl groups, wherein each of the groups may be optionally substituted with one to three substituents independently selected from halogens and CNs.

13. A composition comprising the compound according to any one of claims 1 to 12 in an effective amount for killing fungi.

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

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

16. Compound of formula (XXX) 【Transformation 8】 (In the formula, each A 1 is either N or one A 1 is N and one A 1 CR 1 And; preferably, one A 1 is N and one A 1 CR 1 And; R 1 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 sulfonyl, C 1-6 Alkoxy, amino, and -NHC(O)C 1-6 Selected independently of alkyl groups; preferably R 1 is hydrogen and C 1-6 Selected independently of alkyl; A 4 is CH or N; R 5 C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, diC 1-6 Alkylamino, C 1-6 Alkoxyaminos and C 1-6 Alkyl C 1-6 Selected from alkoxyaminos, where C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, diC 1-6 Alkylamino, C 1-6 Alkoxyaminos and C 1-6 Alkyl C 1-6 Each alkoxyamino group may be optionally substituted with one to three substituents independently selected from halogens and CNs. or its salt or N-oxide.

17. Compound of formula (XI) 【Chemistry 9】 (In the formula, each A 1 is either N or one A 1 is N and one A 1 CR 1 And; preferably, one A 1 is N and one A 1 CR 1 And; R 1 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 sulfonyl, C 1-6 Alkoxy, amino, and -NHC(O)C 1-6 Selected independently of alkyl groups; preferably R 1 is hydrogen and 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 four A 2 CR 2 And; R 2 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 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, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 1-6 Alkyl 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 selected from halogens, hydroxyls, and CNs; preferably, R 2 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, and C 1-6 Alkoxy-C 1-6 Selected independently of alkyl; A 3 CR 3 or N; R 3 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkyl sulfonyl, amino, C 1-6 Alkylamino, diC 1-6 - Alkylamino, and C 3-6 Selected from cycloalkylamino, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkyl sulfonyl, amino, C 1-6 Alkylamino, diC 1-6 - Alkylamino, and C 3-6 Each of the cycloalkylamino groups may be optionally substituted with one to three substituents selected from halogens, hydroxyls, and CNs; preferably, R 3 is hydrogen; R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl, diC 1-6 Alkylaminocarbonyl-C 1-6 Selected from alkyl and CN, where C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 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 selected from halogens and CNs; preferably, R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy, where C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Each alkoxy group may be optionally substituted with one to three substituents independently selected from halogens and CNs; Here, A 3 and R 4 (These elements can optionally come together to form a ring, preferably a six-membered heteroring.) or its salt or N-oxide; or Compound of formula (II) 【Chemistry 10】 (In the formula, each A 1 is either N or one A 1 is N and one A 1 CR 1 And; preferably, one A 1 is N and one A 1 CR 1 And; R 1 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 sulfonyl, C 1-6 Alkoxy, amino, and -NHC(O)C 1-6 Selected independently of alkyl groups; preferably R 1 is hydrogen and 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 four A 2 CR 2 And; R 2 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 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, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 1-6 Alkyl 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 selected from halogens, hydroxyls, and CNs; preferably, R 2 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, and C 1-6 Alkoxy-C 1-6 Selected independently of alkyl; A 3 CR 3 or N; R 3 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkyl sulfonyl, amino, C 1-6 Alkylamino, diC 1-6 - Alkylamino, and C 3-6 Selected from cycloalkylamino, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkyl sulfonyl, amino, C 1-6 Alkylamino, diC 1-6 - Alkylamino, and C 3-6 Each of the cycloalkylamino groups may be optionally substituted with one to three substituents selected from halogens, hydroxyls, and CNs; preferably, R 3 is hydrogen; R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl, diC 1-6 Alkylaminocarbonyl-C 1-6 Selected from alkyl and CN, where C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 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 selected from halogens and CNs; preferably, R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy, where C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Each alkoxy group may be optionally substituted with one to three substituents independently selected from halogens and CNs; Here, A 3 and R 4 They may optionally come together to form a ring, preferably a six-membered heteroring; X is Cl, Br, or I); or its salt or N-oxide.

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