Imidazo[1,2-a]pyrazine derivatives
Imidazo[1,2-a]pyrazine derivatives provide effective fungicidal solutions against oomycetes, addressing the ineffectiveness of existing fungicides and safeguarding agricultural crops from oomycete damage.
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- SYNGENTA CROP PROTECITON AG
- Filing Date
- 2024-04-11
- Publication Date
- 2026-05-01
AI Technical Summary
Existing fungicides are ineffective against oomycetes, a group of plant pathogenic fungi that cause significant damage to crops and harvested food crops.
Development of imidazo[1,2-a]pyrazine derivatives with specific chemical structures that exhibit potent fungicidal activity against oomycetes, including compounds of formula (I) and their use in pesticide compositions.
The imidazo[1,2-a]pyrazine derivatives effectively eradicate, prevent, or control oomycetes, reducing their pathogenicity on plants and harvested food crops, thereby protecting agricultural yields.
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Figure 2026514063000001_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to microbicidal activity, particularly fungicidal activity, more specifically activity against oomycetes, for example, microbicidal imidazo[1,2-a]pyrazine derivatives as active ingredients. The present invention also relates to the preparation of these imidazo[1,2-a]pyrazine derivatives, intermediates useful for the preparation of these imidazo[1,2-a]pyrazine derivatives, the preparation of these intermediates, pesticidal compositions containing at least one of the imidazo[1,2-a]pyrazine derivatives, the preparation of these compositions, and the use of imidazo[1,2-a]pyrazine derivatives or compositions in agriculture or horticulture for controlling, preventing or eradicating the ectoparasitism of plant pathogenic microorganisms, particularly fungi, more specifically oomycetes, on plants, harvested food crops, seeds or abiotic materials.
Summary of the Invention
Problems to be Solved by the Invention
[0002] Surprisingly, it has now been found that certain novel imidazo[1,2-a]pyrazine derivatives have particularly advantageous fungicidal properties against oomycetes.
Means for Solving the Problems
[0003] Thus, in a first aspect, the present invention provides a compound of formula (I):
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 fungicidal effective amount of a compound of formula (I). The composition may further comprise at least one compound selected from additional active ingredients, suitable inactive 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, to the habitats of plant pathogens, to plants particularly susceptible to attack by plant pathogens, or to the reproductive material of plants.
[0006] Accordingly, in a third aspect, the present invention provides the use of a compound of formula (I), or a composition comprising a compound of formula (I), as described herein, for eradicating, preventing or controlling plant pathogens.
[0007] In a fourth aspect, the present invention provides a method for eradicating, preventing or controlling plant pathogens, comprising applying a compound of formula (I) or a composition containing a compound of formula (I), as described herein, to the plant pathogens, to the habitat of the plant pathogens, particularly to plants susceptible to attack by the plant pathogens, or to the reproductive material of plants.
[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), or compositions containing compounds of formula (I), as described herein, 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 those caused by plant pathogenic fungi, comprising applying a compound of formula (I) or a composition containing a compound of formula (I), as described herein, to the plant pathogenic fungi, or to the habitat of the plant pathogenic fungi, particularly to plants susceptible to attack by plant pathogenic fungi, particularly oomycetes, or to the reproductive material of plants.
[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. [Modes for carrying out the invention]
[0011] Definition: - The terms "halogen" or "halo" refer to fluorine (fluoro or F), chlorine (chloro or Cl), bromine (bromo or Br), or iodine (iod or I), preferably fluorine, chlorine, or bromine. The term "-amino" refers to the -NH2 group. -The term "alkyl" as used herein, either alone or as part of a chemical group, preferably refers to a linear or branched hydrocarbon having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylpropyl, 1,3-dimethylbutyl, 1,4-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl, and 2-ethylbutyl. Alkyl alkyl groups having 1 to 4 carbon atoms are preferred, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl. -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. -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-hexadynyl. Alkynnyls having 2 to 4 carbon atoms are preferred, for example, ethynnyl, 2-propynyl, or 2-butynyl-2-propenyl. - The term "haloalkyl" refers to alkyl groups as generally defined above, substituted with one or more identical or different halogen atoms, such as fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, or 2,2,2-trifluoroethyl. -As used herein, the term "cyanoalkyl" refers to an alkyl group, generally defined above, that is substituted with one or more cyano groups. -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. -As used herein, the term "halocycloalkyl" refers to a cycloalkyl group as generally defined above, which is substituted with one or more identical or different halogen atoms. - The term "cyanocycloalkyl" refers to a cycloalkyl group that is substituted with one or more cyano groups, as generally defined above. - The term "alkoxy" is derived from the formula -OR a It refers to the base of, and in the formula, R a This refers to the alkyl group as generally defined above. Examples of alkoxys include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy, and tert-butoxy. The term "alkoxyalkyl" refers to an alkyl group substituted with the aforementioned alkoxy group (as described above). Examples include methoxymethyl, methoxyethyl, ethoxymethyl, and propoxymethyl. - 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. - 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. - 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. - 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. - 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. - 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. - 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. - 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. - 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. -Hydroxyl or hydroxyl represents the -OH group.
[0012] In relation to the present invention, the terms “to eradicate,” “to prevent,” or “to control,” and their variations thereof, mean reducing pathogenicity, more specifically plant pathogenicity, any undesirable effects, such as oomycetes and other fungi, exocaridians or attacks on plants or plant-derived products, and pathogenic damage, to a level in which improvement is demonstrated.
[0013] 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.
[0014] 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.
[0015] Compounds of formula (I) having at least one basic center can form, for example, acid addition salts with strong inorganic acids, such as mineral acids, such as perchloric acid, sulfuric acid, nitric acid, nitrite, phosphoric acid, or hydrohalic acid; strong organic carboxylic acids, such as unsubstituted or substituted C1-C4 alkane carboxylic acids, such as acetic acid; saturated or unsaturated dicarboxylic acids, such as oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, or phthalic acid; hydroxycarboxylic acids, such as ascorbic acid, lactic acid, malic acid, tartaric acid, or citric acid; or benzoic acid, or organic sulfonic acids, such as unsubstituted or substituted 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 a base, for example, inorganic salts, for example alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or salts with ammonia or organic amines, for example morpholine, piperidine, pyrrolidine, mono-, di- or tri-lower alkylamines, for example ethyl-, diethyl-, triethyl or dimethylpropylamine, or mono-, di- or trihydroxy lower alkylamines, for example mono-, di- or triethanolamine.
[0016] In each case, the compound of formula (I) according to the present invention exists in a free form, an oxidized form as an N-oxide, a covalently hydrated form, or a salt form, for example, an agrochemically usable or agrochemically acceptable salt form. The N-oxide is an oxidized form of a tertiary amine or an oxidized form of a nitrogen-containing heteroaromatic compound. These are described, for example, in the book "Heterocyclic N-oxides" by A. Albini and S. Pietra, CRC Press, Boca Raton 1991. The compound of formula (I) according to the present invention also includes hydrates that may be formed during salt formation.
[0017] The compounds of formula (I) according to the present invention also include hydrates that may be formed during salt formation.
[0018] In further embodiments, the compound of formula (I) according to the present invention is R 1a However, 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 From alkoxy, preferably C 1-6 Compounds selected from alkyl groups are provided.
[0019] In further embodiments, the compound of formula (I) according to the present invention is R 1b and R 1c However, hydrogen, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 A compound is provided that is independently selected from alkoxy and preferably hydrogen.
[0020] In a particular embodiment, the compound of formula (I) according to the present invention is R 1a However, 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 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 1b and R 1c A compound in which hydrogen is present is provided.
[0021] 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 and C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, and C 1-6 Independently selected from alkylcarbonyls, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, and C 1-6 Each alkylcarbonyl group may be optionally selected by 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 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Selected independently from 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 However, hydrogen, halogen, CN, C 1-6 Alkyl and C 1-6Compounds independently selected from alkoxys are provided.
[0022] In further embodiments, the compound of formula (I) according to the present invention is R 3 However, hydrogen, hydroxyl, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, amino, C 1-6 Alkylamino, diC 1-6 -alkylamino and C 3-6 Selected from cycloalkylaminos, 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 Compounds are provided in which each of the cycloalkylamino groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs. In a preferred embodiment, R 3 It could be hydrogen.
[0023] In further embodiments, 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.
[0024] 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.
[0025] 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.
[0026] In further embodiments, the compound of formula (I) according to the present invention comprises four A 2 CR 2 A 3 CR 3 Preferably [ka] but [ka] A compound is provided.
[0027] In a particular embodiment, [ka] but [ka] And R 2This 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 1-6 Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxyl, and CN; preferably, R 2 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Selected independently from alkoxy, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6Each of the alkoxy groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; more preferably, R 2 Hydrogen, halogen, CN, C 1-6 Alkyl and C 1-6 It is selected independently of alkoxy.
[0028] 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 C 1-6 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 1-6Each 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 in which these elements can optionally combine to form a ring, more preferably a 5-8 membered heterocycle, and more preferably a 6 membered heterocycle.
[0029] In further embodiments, a compound of formula (I) according to the present invention, A 3 CR 3 And R 3 and R 4 The compounds of formula (I) are provided, which together form a ring, preferably a 5- to 8-membered heterocycle, preferably a 6-membered heterocycle, and more preferably one of W1, W2, or W3 as described in the following compound of formula (I): [ka]
[0030] 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 1 to 3 substituents independently selected from halogens and CN. For example, the compound of formula (I-W3) may be as follows: [ka]
[0031] In preferred embodiments, the compounds of formulas (I-W1), (I-W2), and (I-W3) may be as described below. [ka]
[0032] 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, where C 1-6 Alkyl and C 3-6 Each cycloalkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN. For example, the compound of formula (I-W3) may be as follows: [ka]
[0033] 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.
[0034] In a particular embodiment, the compound of formula (I) according to the present invention is, Z is O; A 1 N is; R 1a However, 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 From alkoxy, preferably C 1-6 Selected from alkyl groups; R 1b However, hydrogen, C 1-6Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy, preferably hydrogen; R 1c However, hydrogen, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy, preferably hydrogen; The four A's 2 CR 2 And; R 2 However, hydrogen, hydroxyl, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, 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 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6Alkyl 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 However, 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 from 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 However, hydrogen, halogen, CN, C 1-6 Alkyl and C 1-6 Selected independently from alkoxy; A 3 CR 3 And R 3 However, hydrogen, hydroxyl, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkylsulfonyl, amino, C 1-6 Alkylamino, diC 1-6 -alkylamino and C 3-6 Selected independently from cycloalkylaminos, where C 1-6Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkylsulfonyl, amino, C 1-6 Alkylamino, diC 1-6 -Alkylamino and C 3-6 Each of the cycloalkylamino groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; preferably R 3 is hydrogen; R 4 However, C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy, where C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Each alkoxy group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN; A 3 and R 4 They can optionally come together to form a ring, more preferably a 5- to 8-membered complex ring, more preferably a 6-membered complex ring; R 5 However, C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6Cycloalkyl-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 A compound of formula (I) is provided, selected from alkyl groups, where each of the groups may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN.
[0035] In a preferred embodiment, [ka] teeth [ka] And R 2 This is as defined in the present invention, and preferably R 2 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, and C 1-6Independently 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 1-6 Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxyl, and CN; preferably, R 2 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Selected independently from alkoxy, where 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 and C 1-6 It is selected independently of alkoxy.
[0036] In further embodiments, the compounds according to the present invention are selected from the following: Methyl N-[5-[6-[2-cyanoethyl-(4-fluoro-3-methoxyphenyl)carbamoyl]-8-methylimidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[cyanomethyl-(4-fluoro-3-methoxyphenyl)carbamoyl]-8-methylimidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[ethyl-(4-fluoro-3-methoxyphenyl)carbamoyl]-8-methylimidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-(6-fluoro-3,4-dihydro-2H-quinoline-1-carbonyl)-8-methylimidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-fluoro-3-methylphenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-fluorophenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-fluoro-3-methoxyphenyl)-(methoxymethyl)carbamoyl]-8-methylimidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[allyl-(3-fluorophenyl)carbamoyl]-8-methylimidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-methoxy-2-pyridyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[8-methyl-6-[methyl-(3-methylsulfonylphenyl)carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; 3-[6-(cyclopropanecarbonylamino)-3-pyridyl]-N-(3,4-difluorophenyl)-N,8-dimethylimidazo[1,2-a]pyrazine-6-carboxamide; 3-[6-(ethylcarbamoylamino)-3-pyridyl]-N-(4-fluoro-3-methoxyphenyl)-N,8-dimethylimidazo[1,2-a]pyrazine-6-carboxamide; N-(4-fluoro-3-methoxyphenyl)-3-[4-[(2-methoxyacetyl)amino]phenyl]-N,8-dimethylimidazo[1,2-a]pyrazine-6-carboxamide; 3-[4-(cyclopropanecarbonylamino)phenyl]-N-(4-fluoro-3-methoxyphenyl)-N,8-dimethylimidazo[1,2-a]pyrazine-6-carboxamide; 3-[4-(ethylcarbamoylamino)phenyl]-N-(4-fluoro-3-methoxyphenyl)-N,8-dimethylimidazo[1,2-a]pyrazine-6-carboxamide; 3-(4-acetamidophenyl)-N-(4-fluoro-3-methoxyphenyl)-N,8-dimethylimidazo[1,2-a]pyrazine-6-carboxamide; 3-(6-acetamido-3-pyridyl)-N-(4-fluoro-3-methoxyphenyl)-N,8-dimethylimidazo[1,2-a]pyrazine-6-carboxamide; 3-[6-(cyclopropanecarbonylamino)-3-pyridyl]-N-(4-fluoro-3-methoxyphenyl)-N,8-dimethylimidazo[1,2-a]pyrazine-6-carboxamide; 3-(6-acetamido-3-pyridyl)-N-(3,4-difluorophenyl)-N,8-dimethylimidazo[1,2-a]pyrazine-6-carboxamide; Methyl N-[5-[8-acetamido-6-[ethyl-(4-fluoro-3-methoxyphenyl)carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[8-acetamido-6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[8-cyano-6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[8-cyclopropyl-6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[8-bromo-6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[8-ethyl-6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-chlorophenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(3,4-difluorophenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-(6-fluoro-4-methyl-2,3-dihydroquinoxaline-1-carbonyl)-8-methylimidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-(7-fluoro-2,3-dihydro-1,4-benzoxazine-4-carbonyl)-8-methylimidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-cyano-3-methylphenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-(6-cyano-3,4-dihydro-2H-quinoline-1-carbonyl)-8-methylimidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-cyanophenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[5-[6-[(4-cyano-3-methoxyphenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; Methyl N-[4-[6-[(4-cyano-3-methoxyphenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyrazine-3-yl]phenyl]carbamate; Methyl N-[4-[6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyrazine-3-yl]phenyl]carbamate; Methyl N-[5-[6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]-2-methyl-imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate; and Methyl N-[5-[6-[(4-fluoro-3-methoxyphenyl)-methyl-carbamoyl]-2,8-dimethyl-imidazo[1,2-a]pyrazine-3-yl]-2-pyridyl]carbamate.
[0037] The methods according to the present invention have advantageous properties for protecting plants from pathogenic attacks or exoparasites 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.
[0038] The compounds listed in Tables 1.1 to 1.297 below exemplify specific compounds of the present invention.
[0039] Table 1.1 provides compounds E1.1 to E1.418 of formula (Ia). [ka] (In the formula, R 1a It is CH3, and R 2 H is R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 (This is defined in Table Z). More specifically, Table Z is A 3 and R 4 This also includes compounds in which both atoms form a ring. In this case, the ring is formed along the amide atoms linked to the biring core of formula (Ia), and the combined A 3 Column and R 4 This is shown in column (Table Z). For example, compound E1.8 A 3 and R 4 Please refer to the column.
[0040] [Table 1-1]
[0041] [Table 1-2]
[0042] [Table 1-3]
[0043] [Table 1-4]
[0044] [Table 1-5]
[0045] [Table 1-6]
[0046] Table 1-7
[0047] Table 1-8
[0048] Table 1-9
[0049] Table 1-10
[0050] Table 1-11
[0051] Table 1-12
[0052] Table 1-13
[0053] Table 1-14
[0054] Table 1-15
[0055] Table 1-16
[0056] [Table 1-17]
[0057] [Table 1-18]
[0058] [Table 1-19]
[0059] [Table 1-20]
[0060] [Table 1-21]
[0061] [Table 1-22]
[0062] [Table 1-23]
[0063] [Table 1-24]
[0064] Table 1.2 provides 418 compounds E2.1 to E2.418 of formula (Ia), where R 1a It is CH3, and R 2 H is R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R4 This is as defined in Table Z. Table 1.3 provides 418 compounds E3.1 to E3.418 of formula (Ia), where R 1a It is CH3, and R 2 H is R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.4 provides 418 compounds E4.1 to E4.418 of formula (Ia), where R 1a It is CH3, and R 2 H is R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.5 provides 418 compounds E5.1 to E5.418 of formula (Ia), where R 1a It is CH3, and R 2 H is R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.6 provides 418 compounds E6.1 to E6.418 of formula (Ia), where R 1a It is CH3, and R 2 It is CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.7 provides 418 compounds E7.1 to E7.418 of formula (Ia), where R 1a It is CH3, and R 2 It is CH3, and R 5 It is OCH3, and A1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.8 provides 418 compounds E8.1 to E8.418 of formula (Ia), where R 1a It is CH3, and R 2 It is CH3, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.9 provides 418 compounds E9.1 to E9.418 of formula (Ia), where R 1a It is CH3, and R 2 It is CH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.10 provides 418 compounds E10.1 to E10.418 of formula (Ia), where R 1a It is CH3, and R 2 It is CH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.11 provides 418 compounds E11.1 to E11.418 of formula (Ia), where R 1a It is CH3, and R 2 It is CH2CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.12 provides 418 compounds E12.1 to E12.418 of formula (Ia), where R 1a It is CH3, and R 2 It is CH2CH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.13 provides 418 compounds E13.1 to E13.418 of formula (Ia), where R 1a It is CH3, and R 2 It is CH2CH3, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.14 provides 418 compounds E14.1 to E14.418 of formula (Ia), where R 1a It is CH3, and R 2 It is CH2CH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.15 provides 418 compounds E15.1 to E15.418 of formula (Ia), where R 1a It is CH3, and R 2 It is CH2CH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.16 provides 418 compounds E16.1 to E16.418 of formula (Ia), where R 1a It is CH3, and R 2 F is R 5 It is CH3, and A 1 , A2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.17 provides 418 compounds E17.1 to E17.418 of formula (Ia), where R 1a It is CH3, and R 2 F is R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.18 provides 418 compounds E18.1 to E18.418 of formula (Ia), where R 1a It is CH3, and R 2 F is R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.19 provides 418 compounds E19.1 to E19.418 of formula (Ia), where R 1a It is CH3, and R 2 F is R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.20 provides 418 compounds E20.1 to E20.418 of formula (Ia), where R 1a It is CH3, and R 2 F is R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.21 provides 418 compounds E21.1 to E21.418 of formula (Ia), where R 1aIt is CH3, and R 2 is Cl, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.22 provides 418 compounds E22.1 to E22.418 of formula (Ia), where R 1a It is CH3, and R 2 is Cl, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.23 provides 418 compounds E23.1 to E23.418 of formula (Ia), where R 1a It is CH3, and R 2 is Cl, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.24 provides 418 compounds E24.1 to E24.418 of formula (Ia), where R 1a It is CH3, and R 2 is Cl, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.25 provides 418 compounds E25.1 to E25.418 of formula (Ia), where R 1a It is CH3, and R 2 is Cl, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.26 provides 418 compounds E26.1 to E26.418 of formula (Ia), where R 1a It is CH3, and R 2 is Br, R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.27 provides 418 compounds E27.1 to E27.418 of formula (Ia), where R 1a It is CH3, and R 2 is Br, R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.28 provides 418 compounds E28.1 to E28.418 of formula (Ia), where R 1a It is CH3, and R 2 is Br, R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.29 provides 418 compounds E29.1 to E29.418 of formula (Ia), where R 1a It is CH3, and R 2 is Br, R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.30 provides 418 compounds E30.1 to E30.418 of formula (Ia), where R 1a It is CH3, and R 2 is Br, R 5 It is NHCH2CH3, and A 1 , A2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.31 provides 418 compounds E31.1 to E31.418 of formula (Ia), where R 1a It is CH3, and R 2 is CN, R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.32 provides 418 compounds E32.1 to E32.418 of formula (Ia), where R 1a It is CH3, and R 2 is CN, R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.33 provides 418 compounds E33.1 to E33.418 of formula (Ia), where R 1a It is CH3, and R 2 is CN, R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.34 provides 418 compounds E34.1 to E34.418 of formula (Ia), where R 1a It is CH3, and R 2 is CN, R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.35 provides 418 compounds E35.1 to E35.418 of formula (Ia), where R 1ais CH3, R 2 is CN, R 5 is NHCH2CH3, A 1 A 2a A 2b A 3 R 4 is as defined in Table Z. Table 1.36 provides 418 compounds E36.1 to E36.418 of formula (Ia), where R 1a is CH3, R 2 is OCH3, R 5 is CH3, A 1 A 2a A 2b A 3 R 4 is as defined in Table Z. Table 1.37 provides 418 compounds E37.1 to E37.418 of formula (Ia), where R 1a is CH3, R 2 is OCH3, R 5 is OCH3, A 1 A 2a A 2b A 3 R 4 is as defined in Table Z. Table 1.38 provides 418 compounds E38.1 to E38.418 of formula (Ia), where R 1a is CH3, R 2 is OCH3, R 5 is cyclopropyl, A 1 A 2a A 2b A<9000898>R 4 is as defined in Table Z. Table 1.39 provides 418 compounds E39.1 to E39.418 of formula (Ia), where R 1a is CH3, R 2 is OCH3, R 5 is CH2OCH3, A 1 A 2a A 2b A 3 R 4This is as defined in Table Z. Table 1.40 provides 418 compounds E40.1 to E40.418 of formula (Ia), where R 1a It is CH3, and R 2 It is OCH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.41 provides 418 compounds E41.1 to E41.418 of formula (Ia), where R 1a It is CH3, and R 2 It is OCH2CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.42 provides 418 compounds E42.1 to E42.418 of formula (Ia), where R 1a It is CH3, and R 2 It is OCH2CH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.43 provides 418 compounds E43.1 to E43.418 of formula (Ia), where R 1a It is CH3, and R 2 It is OCH2CH3, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.44 provides 418 compounds E44.1 to E44.418 of formula (Ia), where R 1a It is CH3, and R 2 It is OCH2CH3, and R5 is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 is as defined in Table Z. Table 1.45 provides 418 compounds E45.1 to E45.418 of formula (Ia), where R 1a is CH3, R 2 is OCH2CH3, R 5 is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 is as defined in Table Z. Table 1.46 provides 418 compounds E46.1 to E46.418 of formula (Ia), where R 1a is CH2CH3, R 2 is H, R 5 is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 is as defined in Table Z. Table 1.47 provides 418 compounds E47.1 to E4e7.418 of formula (Ia), where R 1a is CH2CH3, R 2 is H, R 5 is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 is as defined in Table Z. Table 1.48 provides 418 compounds E48.1 to E48.418 of formula (Ia), where R 1a is CH2CH3, R 2 is H, R 5 is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 is as defined in Table Z. Table 1.49 provides 418 compounds E49.1 to E49.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 H is R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.50 provides 418 compounds E50.1 to E50.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 H is R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.51 provides 418 compounds E51.1 to E51.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 It is CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.52 provides 418 compounds E52.1 to E52.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 It is CH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.53 provides 418 compounds E53.1 to E53.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 It is CH3, and R 5 It is cyclopropyl, and A 1 , A2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.54 provides 418 compounds E54.1 to E54.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 It is CH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.55 provides 418 compounds E55.1 to E55.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 It is CH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.56 provides 418 compounds E56.1 to E56.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 It is CH2CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.57 provides 418 compounds E57.1 to E57.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 It is CH2CH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.58 provides 418 compounds E58.1 to E58.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 It is CH2CH3, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.59 provides 418 compounds E59.1 to E59.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 It is CH2CH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.60 provides 418 compounds E60.1 to E60.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 It is CH2CH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.61 provides 418 compounds E61.1 to E61.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 F is R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.62 provides 418 compounds E62.1 to E62.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 F is R 5 It is OCH3, and A1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.63 provides 418 compounds E63.1 to E63.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 F is R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.64 provides 418 compounds E64.1 to E64.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 F is R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.65 provides 418 compounds E65.1 to E65.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 F is R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.66 provides 418 compounds E66.1 to E66.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 is Cl, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.67 provides 418 compounds E67.1 to E67.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 is Cl, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.68 provides 418 compounds E68.1 to E68.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 is Cl, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.69 provides 418 compounds E69.1 to E69.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 is Cl, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.70 provides 418 compounds E70.1 to E70.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 is Cl, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.71 provides 418 compounds E71.1 to E71.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 is Br, R 5 It is CH3, and A 1 , A2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.72 provides 418 compounds E72.1 to E72.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 is Br, R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.73 provides 418 compounds E73.1 to E73.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 is Br, R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.74 provides 418 compounds E74.1 to E74.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 is Br, R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.75 provides 418 compounds E75.1 to E75.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 is Br, R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.76 provides 418 compounds E76.1 to E76.418 of formula (Ia), where R1a It is CH2CH3, and R 2 is CN, R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.77 provides 418 compounds E77.1 to E77.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 is CN, R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.78 provides 418 compounds E78.1 to E78.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 is CN, R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.79 provides 418 compounds E79.1 to E79.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 is CN, R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.80 provides 418 compounds E80.1 to E80.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 is CN, R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R4 This is as defined in Table Z. Table 1.81 provides 418 compounds E81.1 to E81.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 It is OCH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.82 provides 418 compounds E82.1 to E82.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 It is OCH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.83 provides 418 compounds E83.1 to E83.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 It is OCH3, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.84 provides 418 compounds E84.1 to E84.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 It is OCH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.85 provides 418 compounds E85.1 to E85.418 of formula (Ia), where R 1a It is CH2CH3, and R 2It is OCH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.86 provides 418 compounds E86.1 to E86.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 It is OCH2CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.87 provides 418 compounds E87.1 to E87.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 It is OCH2CH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.88 provides 418 compounds E88.1 to E88.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 It is OCH2CH3, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.89 provides 418 compounds E89.1 to E89.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 It is OCH2CH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4This is as defined in Table Z. Table 1.90 provides 418 compounds E90.1 to E90.418 of formula (Ia), where R 1a It is CH2CH3, and R 2 It is OCH2CH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.91 provides 418 compounds E91.1 to E91.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 H is R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.92 provides 418 compounds E92.1 to E92.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 H is R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.93 provides 418 compounds E93.1 to E93.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 H is R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.94 provides 418 compounds E94.1 to E94.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 H is R 5It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.95 provides 418 compounds E95.1 to E95.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 H is R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.96 provides 418 compounds E96.1 to E96.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 It is CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.97 provides 418 compounds E97.1 to E97.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 It is CH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.98 provides 418 compounds E98.1 to E98.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 It is CH3, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.99 provides 418 compounds E99.1 to E99.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 It is CH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.100 provides 418 compounds E100.1 to E100.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 It is CH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.101 provides 418 compounds E101.1 to E101.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 It is CH2CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.102 provides 418 compounds E102.1 to E102.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 It is CH2CH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.103 provides 418 compounds E103.1 to E103.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 It is CH2CH3, and R 5It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.104 provides 418 compounds E104.1 to E104.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 It is CH2CH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.105 provides 418 compounds E105.1 to E105.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 It is CH2CH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.106 provides 418 compounds E106.1 to E106.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 F is R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.107 provides 418 compounds E107.1 to E107.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 F is R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.108 provides 418 compounds E108.1 to E108.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 F is R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.109 provides 418 compounds E109.1 to E109.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 F is R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.110 provides 418 compounds E110.1 to E110.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 F is R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.111 provides 418 compounds E111.1 to E111.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 is Cl, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.112 provides 418 compounds E112.1 to E112.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 is Cl, and R 5 It is OCH3, and A1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.113 provides 418 compounds E113.1 to E113.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 is Cl, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.114 provides 418 compounds E114.1 to E114.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 is Cl, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.115 provides 418 compounds E115.1 to E115.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 is Cl, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.116 provides 418 compounds E116.1 to E116.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 is Br, R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.117 provides 418 compounds E117.1 to E117.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 is Br, R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.118 provides 418 compounds E118.1 to E118.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 is Br, R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.119 provides 418 compounds E119.1 to E119.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 is Br, R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.120 provides 418 compounds E120.1 to E120.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 is Br, R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.121 provides 418 compounds E121.1 to E121.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 is CN, R 5It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.122 provides 418 compounds E122.1 to E122.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 is CN, R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.123 provides 418 compounds E123.1 to E123.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 is CN, R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.124 provides 418 compounds E124.1 to E124.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 is CN, R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.125 provides 418 compounds E125.1 to E125.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 is CN, R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.126 provides 418 compounds E126.1 to E126.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 It is OCH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.127 provides 418 compounds E127.1 to E127.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 It is OCH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.128 provides 418 compounds E128.1 to E128.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 It is OCH3, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.129 provides 418 compounds E129.1 to E129.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 It is OCH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.130 provides 418 compounds E130.1 to E130.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 It is OCH3, and R 5It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.131 provides 418 compounds E131.1 to E131.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 It is OCH2CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.132 provides 418 compounds E132.1 to E132.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 It is OCH2CH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.133 provides 418 compounds E133.1 to E133.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 It is OCH2CH3, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.134 provides 418 compounds E134.1 to E134.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 It is OCH2CH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4This is as defined in Table Z. Table 1.135 provides 418 compounds E135.1 to E135.418 of formula (Ia), where R 1a It is CH2OCH3, and R 2 It is OCH2CH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.136 provides 418 compounds E136.1 to E136.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 H is R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.137 provides 418 compounds E137.1 to E137.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 H is R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.138 provides 418 compounds E138.1 to E138.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 H is R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.139 provides 418 compounds E139.1 to E139.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2H is R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.140 provides 418 compounds E140.1 to E140.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 It is CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.141 provides 418 compounds E141.1 to E141.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 It is CH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.142 provides 418 compounds E142.1 to E142.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 It is CH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.143 provides 418 compounds E143.1 to E143.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 It is CH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4This is as defined in Table Z. Table 1.144 provides 418 compounds E144.1 to E144.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 It is CH2CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.145 provides 418 compounds E145.1 to E145.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 It is CH2CH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.146 provides 418 compounds E146.1 to E146.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 It is CH2CH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.147 provides 418 compounds E147.1 to E147.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 It is CH2CH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.148 provides 418 compounds E148.1 to E148.418 of formula (Ia), where R 1a It is cyclopropyl, and R2 F is R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.149 provides 418 compounds E149.1 to E149.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 F is R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.150 provides 418 compounds E150.1 to E150.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 F is R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.151 provides 418 compounds E151.1 to E151.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 F is R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.152 provides 418 compounds E152.1 to E152.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 is Cl, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4This is as defined in Table Z. Table 1.153 provides 418 compounds E153.1 to E153.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 is Cl, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.154 provides 418 compounds E154.1 to E154.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 is Cl, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.155 provides 418 compounds E155.1 to E155.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 is Cl, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.156 provides 418 compounds E156.1 to E156.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 is Br, R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.157 provides 418 compounds E157.1 to E157.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2is Br, R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.158 provides 418 compounds E158.1 to E158.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 is Br, R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.159 provides 418 compounds E159.1 to E159.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 is Br, R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.160 provides 418 compounds E160.1 to E160.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 is CN, R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.161 provides 418 compounds E161.1 to E161.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 is CN, R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4This is as defined in Table Z. Table 1.162 provides 418 compounds E162.1 to E162.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 is CN, R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.163 provides 418 compounds E163.1 to E163.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 is CN, R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.164 provides 418 compounds E164.1 to E164.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 It is OCH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.165 provides 418 compounds E165.1 to E165.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 It is OCH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.166 provides 418 compounds E166.1 to E166.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2It is OCH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.167 provides 418 compounds E167.1 to E167.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 It is OCH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.168 provides 418 compounds E168.1 to E168.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 It is OCH2CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.169 provides 418 compounds E169.1 to E169.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 It is OCH2CH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.170 provides 418 compounds E170.1 to E170.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 It is OCH2CH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R4 This is as defined in Table Z. Table 1.171 provides 418 compounds E171.1 to E171.418 of formula (Ia), where R 1a It is cyclopropyl, and R 2 It is OCH2CH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.172 provides 418 compounds E172.1 to E172.418 of formula (Ia), where R 1a teeth [ka] [ka] And R 2 H is R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.173 provides 418 compounds E173.1 to E173.418 of formula (Ia), where R 1a teeth [ka] And R 2 H is R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.174 provides 418 compounds E174.1 to E174.418 of formula (Ia), where R 1a teeth [ka] And R 2 H is R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.175 provides 418 compounds E175.1 to E175.418 of formula (Ia), where R 1a teeth [ka] And R 2 H is R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.176 provides 418 compounds E176.1 to E176.418 of formula (Ia), where R 1a teeth [ka] And R 2 It is CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.177 provides 418 compounds E177.1 to E177.418 of formula (Ia), where R 1a teeth [ka] And R 2 It is CH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.178 provides 418 compounds E178.1 to E178.418 of formula (Ia), where R 1a teeth [ka] And R 2 It is CH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.179 provides 418 compounds E179.1 to E179.418 of formula (Ia), where R 1a teeth [ka] And R 2 It is CH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.180 provides 418 compounds E180.1 to E180.418 of formula (Ia), where R 1a teeth [ka] And R 2 It is CH2CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.181 provides 418 compounds E181.1 to E181.418 of formula (Ia), where R 1a teeth [ka] And R2 It is CH2CH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.182 provides 418 compounds E182.1 to E182.418 of formula (Ia), where R 1a teeth [ka] And R 2 It is CH2CH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.183 provides 418 compounds E183.1 to E183.418 of formula (Ia), where R 1a teeth [ka] And R 2 It is CH2CH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.184 provides 418 compounds E184.1 to E184.418 of formula (Ia), where R 1a teeth [ka] And R 2 F is R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.185 provides 418 compounds E185.1 to E185.418 of formula (Ia), where R 1a teeth [ka] And R 2 F is R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.186 provides 418 compounds E186.1 to E186.418 of formula (Ia), where R 1a teeth [ka] And R 2 F is R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.187 provides 418 compounds E187.1 to E187.418 of formula (Ia), where R 1a teeth [ka] And R 2 F is R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.188 provides 418 compounds E188.1 to E188.418 of formula (Ia), where R 1a teeth [ka] And R 2 is Cl, and R5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.189 provides 418 compounds E189.1 to E189.418 of formula (Ia), where R 1a teeth [ka] And R 2 is Cl, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.190 provides 418 compounds E190.1 to E190.418 of formula (Ia), where R 1a teeth [ka] And R 2 is Cl, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.191 provides 418 compounds E191.1 to E191.418 of formula (Ia), where R 1a teeth [ka] And R 2 is Cl, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.192 provides 418 compounds E192.1 to E192.418 of formula (Ia), where R 1a teeth [ka] And R 2 is Br, R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.193 provides 418 compounds E193.1 to E193.418 of formula (Ia), where R 1a teeth [ka] And R 2 is Br, R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.194 provides 418 compounds E194.1 to E194.418 of formula (Ia), where R 1a teeth [ka] And R 2 is Br, R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.195 provides 418 compounds E195.1 to E195.418 of formula (Ia), where R 1a teeth [ka] And R 2 is Br, R5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.196 provides 418 compounds E196.1 to E196.418 of formula (Ia), where R 1a teeth [ka] And R 2 is CN, R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.197 provides 418 compounds E197.1 to E197.418 of formula (Ia), where R 1a teeth [ka] And R 2 is CN, R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.198 provides 418 compounds E198.1 to E198.418 of formula (Ia), where R 1a teeth [ka] And R 2 is CN, R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.199 provides 418 compounds E199.1 to E199.418 of formula (Ia), where R 1a teeth [ka] And R 2 is CN, R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.200 provides 418 compounds E200.1 to E200.418 of formula (Ia), where R 1a teeth [ka] And R 2 It is OCH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.201 provides 418 compounds E201.1 to E201.418 of formula (Ia), where R 1a teeth [ka] And R 2 It is OCH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.202 provides 418 compounds E202.1 to E202.418 of formula (Ia), where R 1a teeth [ka] And R 2 It is OCH3, and R5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.203 provides 418 compounds E203.1 to E203.418 of formula (Ia), where R 1a teeth [ka] And R 2 It is OCH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.204 provides 418 compounds E204.1 to E204.418 of formula (Ia), where R 1a teeth [ka] And R 2 It is OCH2CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.205 provides 418 compounds E205.1 to E205.418 of formula (Ia), where R 1a teeth [ka] And R 2 It is OCH2CH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.206 provides 418 compounds E206.1 to E206.418 of formula (Ia), where R 1a teeth [ka] And R 2 It is OCH2CH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.207 provides 418 compounds E207.1 to E207.418 of formula (Ia), where R 1a teeth [ka] And R 2 It is OCH2CH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is as defined in Table Z. Table 1.208 provides 418 compounds E208.1 to E208.418 of formula (Ia), where R 1a NHAc is R 2 H is R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.209 provides 418 compounds E209.1 to E209.418 of formula (Ia), where R 1a NHAc is R 2 H is R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.210 provides 418 compounds E210.1 to E210.418 of formula (Ia), where R 1a NHAc is R 2 H is R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.211 provides 418 compounds E211.1 to E211.418 of formula (Ia), where R 1a NHAc is R 2 H is R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.212 provides 418 compounds E212.1 to E212.418 of formula (Ia), where R 1a NHAc is R 2 H is R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.213 provides 418 compounds E213.1 to E213.418 of formula (Ia), where R 1a NHAc is R 2 It is CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.214 provides 418 compounds E214.1 to E214.418 of formula (Ia), where R 1a NHAc is R 2 It is CH3, and R 5 It is OCH3, and A1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.215 provides 418 compounds E215.1 to E215.418 of formula (Ia), where R 1a NHAc is R 2 It is CH3, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.216 provides 418 compounds E216.1 to E216.418 of formula (Ia), where R 1a NHAc is R 2 It is CH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.217 provides 418 compounds E217.1 to E217.418 of formula (Ia), where R 1a NHAc is R 2 It is CH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.218 provides 418 compounds E218.1 to E218.418 of formula (Ia), where R 1a NHAc is R 2 It is CH2CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.219 provides 418 compounds E219.1 to E219.418 of formula (Ia), where R 1a NHAc is R 2 It is CH2CH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.220 provides 418 compounds E220.1 to E220.418 of formula (Ia), where R 1a NHAc is R 2 It is CH2CH3, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.221 provides 418 compounds E221.1 to E221.418 of formula (Ia), where R 1a NHAc is R 2 It is CH2CH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.222 provides 418 compounds E222.1 to E222.418 of formula (Ia), where R 1a NHAc is R 2 It is CH2CH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.223 provides 418 compounds E223.1 to E223.418 of formula (Ia), where R 1a NHAc is R 2 F is R 5 It is CH3, and A1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.224 provides 418 compounds E224.1 to E224.418 of formula (Ia), where R 1a NHAc is R 2 F is R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.225 provides 418 compounds E225.1 to E225.418 of formula (Ia), where R 1a NHAc is R 2 F is R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.226 provides 418 compounds E226.1 to E226.418 of formula (Ia), where R 1a NHAc is R 2 F is R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.227 provides 418 compounds E227.1 to E227.418 of formula (Ia), where R 1a NHAc is R 2 F is R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.228 provides 418 compounds E228.1 to E228.418 of formula (Ia), where R 1a NHAc is R 2 is Cl, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.229 provides 418 compounds E229.1 to E229.418 of formula (Ia), where R 1a NHAc is R 2 is Cl, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.230 provides 418 compounds E230.1 to E230.418 of formula (Ia), where R 1a NHAc is R 2 is Cl, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.231 provides 418 compounds E231.1 to E231.418 of formula (Ia), where R 1a NHAc is R 2 is Cl, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.232 provides 418 compounds E232.1 to E232.418 of formula (Ia), where R 1a NHAc is R 2 is Cl, and R 5 It is NHCH2CH3, and A 1 , A2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.233 provides 418 compounds E233.1 to E233.418 of formula (Ia), where R 1a NHAc is R 2 is Br, R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.234 provides 418 compounds E234.1 to E234.418 of formula (Ia), where R 1a NHAc is R 2 is Br, R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.235 provides 418 compounds E235.1 to E235.418 of formula (Ia), where R 1a NHAc is R 2 is Br, R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.236 provides 418 compounds E236.1 to E236.418 of formula (Ia), where R 1a NHAc is R 2 is Br, R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.237 provides 418 compounds E237.1 to E237.418 of formula (Ia), where R1a NHAc is R 2 is Br, R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.238 provides 418 compounds E238.1 to E238.418 of formula (Ia), where R 1a NHAc is R 2 is CN, R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.239 provides 418 compounds E239.1 to E239.418 of formula (Ia), where R 1a NHAc is R 2 is CN, R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.240 provides 418 compounds E240.1 to E240.418 of formula (Ia), where R 1a NHAc is R 2 is CN, R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.241 provides 418 compounds E241.1 to E241.418 of formula (Ia), where R 1a NHAc is R 2 is CN, R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R4 This is defined in Table Z. Table 1.242 provides 418 compounds E242.1 to E242.418 of formula (Ia), where R 1a NHAc is R 2 is CN, R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.243 provides 418 compounds E243.1 to E243.418 of formula (Ia), where R 1a NHAc is R 2 It is OCH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.244 provides 418 compounds E244.1 to E244.418 of formula (Ia), where R 1a NHAc is R 2 It is OCH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.245 provides 418 compounds E245.1 to E245.418 of formula (Ia), where R 1a NHAc is R 2 It is OCH3, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.246 provides 418 compounds E246.1 to E246.418 of formula (Ia), where R 1a NHAc is R 2It is OCH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.247 provides 418 compounds E247.1 to E247.418 of formula (Ia), where R 1a NHAc is R 2 It is OCH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.248 provides 418 compounds E248.1 to E248.418 of formula (Ia), where R 1a NHAc is R 2 It is OCH2CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.249 provides 418 compounds E249.1 to E249.418 of formula (Ia), where R 1a NHAc is R 2 It is OCH2CH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.250 provides 418 compounds E250.1 to E250.418 of formula (Ia), where R 1a NHAc is R 2 It is OCH2CH3, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4This is defined in Table Z. Table 1.251 provides 418 compounds E251.1 to E251.418 of formula (Ia), where R 1a NHAc is R 2 It is OCH2CH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.252 provides 418 compounds E252.1 to E252.418 of formula (Ia), where R 1a NHAc is R 2 It is OCH2CH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.253 provides 418 compounds E253.1 to E253.418 of formula (Ia), where R 1a is CN, R 2 H is R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.254 provides 418 compounds E254.1 to E254.418 of formula (Ia), where R 1a is CN, R 2 H is R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.255 provides 418 compounds E255.1 to E255.418 of formula (Ia), where R 1a is CN, R 2 H is R 5It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.256 provides 418 compounds E256.1 to E256.418 of formula (Ia), where R 1a is CN, R 2 H is R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.257 provides 418 compounds E257.1 to E257.418 of formula (Ia), where R 1a is CN, R 2 H is R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.258 provides 418 compounds E258.1 to E258.418 of formula (Ia), where R 1a is CN, R 2 It is CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.259 provides 418 compounds E259.1 to E259.418 of formula (Ia), where R 1a is CN, R 2 It is CH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.260 provides 418 compounds E260.1 to E260.418 of formula (Ia), where R 1a is CN, R 2 It is CH3, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.261 provides 418 compounds E261.1 to E261.418 of formula (Ia), where R 1a is CN, R 2 It is CH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.262 provides 418 compounds E262.1 to E262.418 of formula (Ia), where R 1a is CN, R 2 It is CH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.263 provides 418 compounds E263.1 to E263.418 of formula (Ia), where R 1a is CN, R 2 It is CH2CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.264 provides 418 compounds E264.1 to E264.418 of formula (Ia), where R 1a is CN, R 2 It is CH2CH3, and R 5 It is OCH3, and A 1 , A2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.265 provides 418 compounds E265.1 to E265.418 of formula (Ia), where R 1a is CN, R 2 It is CH2CH3, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.266 provides 418 compounds E266.1 to E266.418 of formula (Ia), where R 1a is CN, R 2 It is CH2CH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.267 provides 418 compounds E267.1 to E267.418 of formula (Ia), where R 1a is CN, R 2 It is CH2CH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.268 provides 418 compounds E268.1 to E268.418 of formula (Ia), where R 1a is CN, R 2 F is R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.269 provides 418 compounds E269.1 to E269.418 of formula (Ia), where R 1a is CN, R 2 F is R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.270 provides 418 compounds E270.1 to E270.418 of formula (Ia), where R 1a is CN, R 2 F is R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.271 provides 418 compounds E271.1 to E271.418 of formula (Ia), where R 1a is CN, R 2 F is R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.272 provides 418 compounds E272.1 to E272.418 of formula (Ia), where R 1a is CN, R 2 F is R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.273 provides 418 compounds E273.1 to E273.418 of formula (Ia), where R 1a is CN, R 2 is Cl, and R 5 It is CH3, and A 1 , A 2a , A2b , A 3 , R 4 This is defined in Table Z. Table 1.274 provides 418 compounds E274.1 to E274.418 of formula (Ia), where R 1a is CN, R 2 is Cl, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.275 provides 418 compounds E275.1 to E275.418 of formula (Ia), where R 1a is CN, R 2 is Cl, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.276 provides 418 compounds E276.1 to E276.418 of formula (Ia), where R 1a is CN, R 2 is Cl, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.277 provides 418 compounds E277.1 to E277.418 of formula (Ia), where R 1a is CN, R 2 is Cl, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.278 provides 418 compounds E278.1 to E278.418 of formula (Ia), where R 1a is CN, R2 is Br, R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.279 provides 418 compounds E279.1 to E279.418 of formula (Ia), where R 1a is CN, R 2 is Br, R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.280 provides 418 compounds E280.1 to E280.418 of formula (Ia), where R 1a is CN, R 2 is Br, R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.281 provides 418 compounds E281.1 to E281.418 of formula (Ia), where R 1a is CN, R 2 is Br, R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.282 provides 418 compounds E282.1 to E282.418 of formula (Ia), where R 1a is CN, R 2 is Br, R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.283 provides 418 compounds E283.1 to E283.418 of formula (Ia), where R 1a is CN, R 2 is CN, R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.284 provides 418 compounds E284.1 to E284.418 of formula (Ia), where R 1a is CN, R 2 is CN, R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.285 provides 418 compounds E285.1 to E285.418 of formula (Ia), where R 1a is CN, R 2 is CN, R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.286 provides 418 compounds E286.1 to E286.418 of formula (Ia), where R 1a is CN, R 2 is CN, R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.287 provides 418 compounds E287.1 to E287.418 of formula (Ia), where R 1a is CN, R 2 is CN, R 5 It is NHCH2CH3, and A 1 , A2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.288 provides 418 compounds E288.1 to E288.418 of formula (Ia), where R 1a is CN, R 2 It is OCH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.289 provides 418 compounds E289.1 to E289.418 of formula (Ia), where R 1a is CN, R 2 It is OCH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.290 provides 418 compounds E290.1 to E290.418 of formula (Ia), where R 1a is CN, R 2 It is OCH3, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.291 provides 418 compounds E291.1 to E291.418 of formula (Ia), where R 1a is CN, R 2 It is OCH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.292 provides 418 compounds E292.1 to E292.418 of formula (Ia), where R1a is CN, R 2 It is OCH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.293 provides 418 compounds E293.1 to E293.418 of formula (Ia), where R 1a is CN, R 2 It is OCH2CH3, and R 5 It is CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.294 provides 418 compounds E294.1 to E294.418 of formula (Ia), where R 1a is CN, R 2 It is OCH2CH3, and R 5 It is OCH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.295 provides 418 compounds E295.1 to E295.418 of formula (Ia), where R 1a is CN, R 2 It is OCH2CH3, and R 5 It is cyclopropyl, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z. Table 1.296 provides 418 compounds E296.1 to E296.418 of formula (Ia), where R 1a is CN, R 2 It is OCH2CH3, and R 5 It is CH2OCH3, and A 1 , A 2a , A 2b , A3 , R 4 This is defined in Table Z. Table 1.297 provides 418 compounds E297.1 to E297.418 of formula (Ia), where R 1a is CN, R 2 It is OCH2CH3, and R 5 It is NHCH2CH3, and A 1 , A 2a , A 2b , A 3 , R 4 This is defined in Table Z.
[0065] The compounds according to the present invention may have several advantages, including, in particular, a favorable level of biological activity for protecting plants from fungal diseases, or excellent properties for use as agricultural chemical active ingredients (e.g., higher biological activity, favorable activity spectrum, increased safety profile, improved physicochemical properties, or increased biodegradability). The compounds according to the present invention have a particularly favorable level of biological activity for protecting plants from oomycetes such as Phytophthora, Plasmopara, and Pythium.
[0066] Compounds of formula (I) where Z is O can be prepared as shown in schemes 1 to 18 below, in which case, unless otherwise specified, the definition of each variable site is as defined in the present invention.
[0067] The compound of formula (I) is mixed with a base such as Cs2CO3, K2CO3, or NaOtBu and a suitable palladium catalyst such as tetrakistriphenylphosphine palladium, [1,1-bis(diphenylphosphine)ferrocene]dichloropalladium(II), bis(diphenylphosphine)palladium(II) chloride, palladium chloride, or palladium acetate, in a suitable solvent such as dimethylformamide, dioxane, tetrahydrofuran, ethanol, or water, with the compound of formula (II) where X is Cl, Br, or I, 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 (III) that can form a 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
[0068] Alternatively, the compound of formula (I) can be prepared by directly arylating the compound of formula (IV) with the compound of formula (V) (wherein X is Cl, Br, or I) in the presence of a catalyst such as palladium diacetate, a ligand such as triphenylphosphine or (dicyclohexylphosphino)biphenyl, and a base such as cesium carbonate or potassium carbonate. The compound of formula (V) where X is Cl, Br, or I can be prepared by known methods or is commercially available. This coupling reaction is shown in Scheme 2. [ka] Scheme 2
[0069] The compound of formula (II) (wherein X is Cl, Br or I) is used with the compound of formula (VI) (wherein X is Cl, Br or I) and the reagent of formula (VII) (wherein X 1 It can be prepared by reacting a good leaving group (such as Cl, Br, I, triflate, tosyl, or mesyl) with a base such as Cs2CO3, K2CO3, NaH, or NaOtBu. 7Compounds of formula (VIII) in which X is an electron-withdrawing group such as a cyano or ester can alternatively be used to functionalize the amide nitrogen in the presence of a base such as triethylamine or 1,8-diazabicyclo[5.4.0]undeca-7-ene. Compounds of formula (VI) in which X is Cl, Br or I, and X 2 This can be prepared by a peptide coupling reaction between a compound of formula (IX) having an OH group and an amine of formula (X), and by activating the carboxylic acid functional group of the compound of formula (IX), which is a process usually carried out by converting the -OH group of the carboxylic acid to a good leaving group such as a chloride group by using (COCl)2 or SOCl2, for example, 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 such as cyclic anhydride of 1-propanephosphonic acid (T3P). For example, see Chem.Soc.Rev.2009,38,606 and Chem.Soc.Rev.2011,40,5084. Alternatively, a compound of formula (II) where X is Cl, Br or I is a compound where X is Cl, Br or I, and X 2 This can be obtained using the above conditions by amide coupling transformation of the compound of formula (IX), in which the OH group is, with the amine of formula (XI). These transformations are shown in Scheme 3. [ka] Scheme 3
[0070] The compound of formula (XI) is commercially available, or the compound of formula (X) and the compound of formula (VII) (wherein X 1The compound of formula (XI) can be obtained by the reaction of the compound of formula (X) with the compound of formula (VIII) (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 (XI) can be obtained by the reaction of the compound of formula (X) with the compound of formula (VIII) (wherein R is a good leaving group such as Cl, Br, I, triflate, tosyl or mesyl). 7 The compound of formula (XI) can also be synthesized by reacting it with an electron-withdrawing group (such as a cyano or ester) in the presence of a base, optionally triethylamine or 1,8-diazabicyclo[5.4.0]undeca-7-ene. Alternatively, the compound of formula (XI) can be synthesized in a suitable solvent, optionally in the presence of a Brønsted or Lewis acid such as acetic acid, for example, in the presence of NaBH(OAc)3 or NaBH3CN, with the aldehyde of formula (XII) (wherein R is an electron-withdrawing group such as a cyano or ester). 8 C 1-5 Alkyl, C 1-6 Alkoxy-C 1-5 Alkyl, C 3-6 Cycloalkyl-C 1-3 Alkyl, C 1-5 Alkenil, C 1-5 Alkinyl, C 1-5 Alkoxy, C 1-6 Alkylsulfanyl-C 1-5 Alkyl, C 1-6 Alkylsulfanyl-C 1-5 Alkyl, C 1-6 Alkylsulfonyl-C 1-5 Alkyl, C 1-6 Alkoxycarbonyl-C 1-5 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-5 Alkyl, diC 1-6 Alkylaminocarbonyl-C 1-5 It can be obtained from the amine of formula (X) by reductive amination with an alkyl group (selected from alkyl groups). Alternatively, another reagent system for reductive amination uses a combination of titanium isopropoxide and NaBH4. The synthesis of the compound of formula (XI) from the amine of formula (X) is described in Scheme 4. [ka] Scheme 4
[0071] Alternatively, the compound of formula (II), where X is Cl, Br, or I, can be prepared by reacting the compound of formula (IV) with a halogenating agent such as N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, or bromine in a suitable solvent such as dichloromethane, chloroform, tetrahydrofuran, or acetonitrile. The compound of formula (IV) is made by reacting the amine of formula (XI) with the compound of formula (XIII) (wherein X is Cl, Br, or I). 2 This can be obtained by amide coupling conversion with (wherein XIII is OH), and by activating the carboxylic acid functional group of the compound of formula (XIII), which is a process usually carried out by converting the -OH of the carboxylic acid to a good leaving group such as a chloride group by using (COCl)2 or SOCl2 in a suitable solvent (e.g., acetonitrile) in the presence of a base such as triethylamine or N,N-diisopropylethylamine, preferably in the presence of a base such as triethylamine or N,N-diisopropylethylamine, preferably in the presence of a base (e.g., triethylamine or N,N-diisopropylethylamine), preferably in a suitable solvent (e.g., acetonitrile), under conditions described in the literature for amide coupling such as cyclic anhydride of 1-propanephosphonic acid (T3P), for example, by using (COCl)2 or SOCl2, before treatment with the amine of formula (XI). Alternatively, the compound of formula (IV) can be obtained by converting the compound of formula (XIV) to the compound of formula (VII) (wherein X is OH). 1 The compound of formula (IV) can be obtained by alkylating the compound of formula (VIII) (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 (IV) can be obtained by alkylating the compound of formula (XIV) with the compound of formula (VIII) (wherein R is a good leaving group such as Cl, Br, I, triflate, tosyl, or mesyl). 7 The compound of formula (XIV) can also be synthesized by reacting it with an electron-withdrawing group (such as a cyano or ester) in the presence of a base, optionally triethylamine or 1,8-diazabicyclo[5.4.0]undeca-7-ene. The compound of formula (XIV) can be synthesized using the above conditions to form formula (XIII) (wherein X 2It can be prepared from a compound (where is OH) by peptide coupling conversion with the amine of formula (X). These conversions are shown in Scheme 5. [ka] Scheme 5
[0072] Alternatively, the compound of formula (IV) can be synthesized by reacting the compound of formula (XV) (wherein X is Cl, Br, or I) with the amine of formula (XI) and carbon monoxide in the presence of a catalyst such as [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) and optionally a base such as triethylamine. This transformation is shown in Scheme 6. [ka] Scheme 6
[0073] Alternatively, the compound of formula (IV) is derived from the compound of formula (XVI) where X is Cl, Br, or I, R 6 Hydrogen and C are independent of each other. 1-6 Alkyl or two R 6 together become C 3-8The compounds can be obtained by cross-coupling transformation with a compound of formula (XVII) that forms a cycloalkyl group (Suzuki cross-coupling) or a compound of formula (XVIII) (Still coupling), or by a palladium-catalyzed cyanation reaction. Suzuki cross-coupling can be achieved by using a suitable palladium catalyst such as tetrakistriphenylphosphine palladium, [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II), bis(diphenylphosphine)palladium(II) chloride, palladium chloride, 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 by using a suitable palladium catalyst such as tetrakistriphenylphosphine palladium, tris(dibenzylideneacetone)dipalladium, palladium chloride, or palladium acetate in a suitable solvent such as dimethylformamide, dioxane, or acetonitrile in the presence of a base such as Cs2CO3 or sodium acetate. Palladium-catalyzed cyanation can be achieved by using a suitable catalyst such as tris(dibenzylideneacetone)dipalladium(0), palladium acetate, or [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II), along with a suitable ligand such as 5-diphenylphosphanyl-9,9-dimethylxanthene-4-yl)-diphenylphosphan (xanthophos), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (Xphos), and a cyanidating agent such as zinc cyanide, potassium cyanide, or potassium hexacyanoferrate(II), in the presence of a base such as potassium acetate or cesium carbonate, in a suitable solvent such as dimethylformamide, dioxane, or tetrahydrofuran, with or without water as a cosolvent. 6 Hydrogen and C are independent of each other. 1-6 Alkyl or two R 6 together become C 3-8Compounds of formula (XVII) and (XVIII) that can form cycloalkyl groups are prepared by known methods or are commercially available. These transformations are shown in Scheme 7. [ka] Scheme 7
[0074] Alternatively, the compound of formula (IV) is formed in the presence of a base such as pyridine or diisopropylethylamine, and the compound of formula (XX) (wherein X is Cl or Br, and R 9 is C 1-6 The compound of formula (XIX) can be obtained from the compound of formula (XIX) by reaction with an alkyl group. The amine of formula (XIX) can be prepared by treating the compound of formula (XXI) in a protic solvent such as methanol with an acid, typically hydrochloric acid, or with sodium acetate and hydroxyamine hydrochloride. The compound of formula (XXI) can be synthesized by reacting the compound of formula (XVI) (wherein X is Cl, Br, or I) with diphenylmethaneimine (CAS number 1013-88-3) in the presence of a catalyst such as palladium acetate or tris(dibenzylideneacetone)dipalladium, and 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), in the presence of a base such as cesium carbonate or sodium tert-butoxide. Alternatively, the compound of formula (IV) is the compound of formula (XVI) and the compound of formula (XXII) (wherein R 9 is C 1-6It can be directly obtained by reacting an alkyl group with a palladium-catalyzed coupling reaction (Buchwald-Hartwig reaction). This reaction can be achieved using a suitable catalyst such as xanthophos-Pd-G2 (CAS 1375325-77-1), xanthophos-Pd G3 (CAS 1445085-97-1), or [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) in a suitable solvent such as dioxane, tetrahydrofuran, or toluene, in the presence of a base such as cesium carbonate, sodium tert-butoxide, or potassium phosphate. These transformations are shown in Scheme 8. [ka] Scheme 8
[0075] Compound of formula (XIV) (wherein X 2 (where R is OH) is a compound of formula (XXIII) (where R is OH) 9 is C 1-6 Since it is alkyl, it can be synthesized by treatment with an acid or base. This conversion is well known to those skilled in the art. 10 C 1-6 The alkyl compound of formula (XXIII) can be converted to the compound of formula (XXIV) (where X is Cl, Br, or I, and R) by cross-coupling transformation with the compound of formula (XVII) (Suzuki cross-coupling) or the compound of formula (XVIII) (Still coupling) using the above conditions. 10 is C 1-6 It can be obtained from (which is alkyl). These transformations are shown in Scheme 9. [ka] Scheme 9
[0076] Alternatively, R 10 C 1-6 A compound of formula (XXIII) that is alkyl, in the presence of a base such as pyridine or diisopropylethylamine, is a compound of formula (XX) (wherein X is Cl or Br, and R 9 is C 1-6The reaction with alkyl compounds results in the compound of formula (XXV) (wherein R is R). 10 is C 1-6 It can be obtained from (which is alkyl). 10 C 1-6 Alkyl amines of formula (XXV) can be converted to compounds of formula (XXVI) (R) in a protic solvent such as methanol using an acid, typically hydrochloric acid, or sodium acetate and hydroxyamine hydrochloride. 10 teeth 1-6 It can be prepared by treating (which is alkyl). 10 C 1-6 The alkyl compound of formula (XXVI) can be converted into the compound of formula (XXIV) (wherein X is Cl, Br or I, and R) in the presence of a catalyst such as palladium acetate or tris(dibenzylideneacetone)dipalladium, optionally in the presence of 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), in the presence of a base such as cesium carbonate or sodium tert-butoxide. 10 is C 1-6 It can be synthesized by reacting an alkyl group with diphenylmethaneimine (CAS number 1013-88-3). These transformations are shown in Scheme 10. [ka] Scheme 10
[0077] The compound of formula (XV) (wherein X is Cl, Br or I) is a hydrazone of formula (XXVII) (wherein X is Cl, Br or I) in the presence of a base such as Cs2CO3, K2CO3 or 1,8-diazabicyclo[5.4.0]undeca-3-7ene, and the compound of formula (XXVIII) (wherein R 6 These are, independently of each other, hydrogen and C 1-6 Alkyl or two R 6 Both are C 3-8 It can form a cycloalkyl group, R 11 C 1-5 Alkyl, C 1-6Alkoxy-C 1-5 Alkyl and C 3-6 Cycloalkyl-C 1-3 It can be prepared by cross-coupling with a compound of formula (selected from alkyl). Such conversions are described in the literature, e.g., Org. Lett. 2020, 22, 2271. Alternatively, a compound of formula (XV) (wherein X is Cl, Br or I) can be converted to a hydrazone of formula (XXVII) (wherein X is Cl, Br or I) to an alkoxide of formula (XXIX) (wherein R 12 is C 1-5 It can be obtained by reacting an alkyl group with a protic solvent such as methanol or tert-butanol. Compound of formula (XXVIII) (wherein R 6 These are, independently of each other, hydrogen and C 1-6 Alkyl or two R 6 They are together C 3-8 It can form a cycloalkyl group, R 11 C 1-5 Alkyl, C 1-6 Alkoxy-C 1-5 Alkyl and C 3-6 Cycloalkyl-C 1-3 (selected from alkyl), and formula (XXIX) (wherein R 12 is C 1-5 Compounds of formula (which is alkyl) are commercially available or can be prepared by known methods. Hydrazone of formula (XXVII) (wherein X is Cl, Br, or I) can be prepared by condensation of p-toluenesulfone hydrazide (CAS 1576-35-8) and aldehyde of formula (XXX) (wherein X is Cl, Br, or I). Aldehydes of formula (XXX) (wherein X is Cl, Br, or I) are commercially available or can be prepared by condensation of compound (XXXI) (wherein X is Cl, Br, or I) and compound (XXXII) (wherein X is Cl, Br, or I) or its corresponding acetal of formula (XXXIII) (wherein X is Cl, Br, or I) in a solvent such as water, ethanol, acetone, or acetonitrile. 13 These are, independently of each other, C 1-6 Alkyl or two R13 Both are C 3-8 It can be prepared by condensation with 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. The compounds of formula (XXXI) (wherein X is Cl, Br, or I), formula (XXXII) (wherein X is Cl, Br, or I), and formula (XXXIII) (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 11. [ka] Scheme 11
[0078] The compound of formula (XVI) (wherein X is Cl, Br or I) is a compound of the amine of formula (XI) and the compound of formula (XXXIV) (wherein X is Cl, Br or I, X 2 This can be obtained by amide coupling conversion of the compound of formula (XXXIV) (wherein X is OH), and by activation of the carboxylic acid functional group of the compound of formula (XXXIV), which is a process usually carried out by converting the -OH of the carboxylic acid to a good leaving group such as a chloride group by using, for example (COCl)2 or SOCl2, in a suitable solvent (e.g., acetonitrile), preferably at a temperature of 25°C to 60°C, preferably in the presence of a base such as triethylamine or N,N-diisopropylethylamine, before treatment with the amine of formula (XI); 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 such as cyclic anhydride of 1-propanephosphonic acid (T3P), for example (COCl)2 or SOCl2. 2 (wherein X is OH) is a compound of formula (XXIV) (wherein X is Cl, Br or I, and R 10 is C1-6 It can be prepared by hydrolysis of the ester functional group of alkyl, which is obtained by using the above conditions to form a compound of formula (XXXV) (wherein X is Cl, Br or I, and R 10 is C 1-6 A compound of formula (XXXII) (wherein X is Cl, Br or I) or the corresponding acetal of formula (XXXIII) (wherein X is Cl, Br or I, and R 13 These are, independently of each other, C 1-6 Alkyl or two R 13 Both are C 3-8 It can be synthesized by condensation with a compound of formula (XXXV) (wherein X is Cl, Br or I, and R 10 C 1-6 The alkyl groups are commercially available or prepared using methods known to those skilled in the art. These conversions are shown in Scheme 12. [ka] Scheme 12
[0079] Alternatively, the compound of formula (I) is the amine of formula (XI) and the compound of formula (XXXVI) (wherein X is Cl, Br, or I, and X 2This can be prepared by amide coupling conversion of (where is OH), and by activating the carboxylic acid functional group of the compound of formula (XXXVI), which is a process usually carried out by converting the -OH of the carboxylic acid to a good leaving group such as a chloride group by using (COCl)2 or SOCl2, for example, 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 such as cyclic anhydride of 1-propanephosphonic acid (T3P). Alternatively, the compound of formula (I) can be converted into the compound of formula (XXXVII) in the presence of a base such as Cs2CO3, K2CO3, NaH, or NaOtBu. 1 It can be prepared by alkylating with Cl, Br, I, triflate, tosyl or mesyl (which are good leaving groups). Alternatively, the compound of formula (I) can be prepared by alkylating the compound of formula (XXXVII) with R 7 The compound of formula (VIII), in which is an electron-withdrawing group such as a cyano or ester, can also be synthesized by reacting it with a base such as triethylamine or 1,8-diazabicyclo[5.4.0]undeca-7-ene, optionally in the presence of such a base. The compound of formula (XXXVII) can be synthesized using the above conditions by reacting it with the compound of formula (XXXVI) (wherein X 2 It can be synthesized from the amine of formula (X) (where is OH) by peptide coupling transformation. These transformations are shown in Scheme 13. [ka] Scheme 13
[0080] Compound of formula (XXXVI) (wherein X 2 (where R is OH) is a compound of formula (XXXVIII) (where R is in the formula)10 is C 1-6 It can be obtained by hydrolysis of the ester portion of the alkyl group. Compound of formula (XXXVIII) (wherein R 10 is C 1-6 A compound of formula (XXIII) (wherein R is alkyl) is formed in the presence of a catalyst such as palladium diacetate, a ligand such as triphenylphosphine or (dicyclohexylphosphine)biphenyl, and a base such as cesium carbonate or calcium carbonate. 10 is C 1-6 It can be prepared by direct arylation of an alkyl compound with a compound of formula (V) (wherein X is Cl, Br, or I). Alternatively, a compound of formula (XXXVIII) (wherein R 10 is C 1-6 A compound of formula (XXXIX) (wherein X is Cl, Br or I, and R) is formed in the presence of a base such as Cs2CO3, K2CO3 or NaOtBu and a suitable palladium catalyst such as tetrakistriphenylphosphine palladium, [1,1-bis(diphenylphosphine)ferrocene]dichloropalladium(II), bis(diphenylphosphine)palladium(II) chloride, palladium chloride or palladium acetate, in a suitable solvent such as dimethylformamide, dioxane, tetrahydrofuran, ethanol or water. 10 is C 1-6 (It is alkyl) and the compound of formula (III) (wherein R 6 These are, independently of each other, hydrogen and C 1-6 Alkyl or two R 6 Both are C 3-8 It can be generated from a Suzuki coupling reaction with a compound of formula (XXXIX) (where X is Cl, Br or I, and R 10 is C 1-6 A compound of formula (XXIII) (wherein R is alkyl) is dissolved in a suitable solvent such as dichloromethane, chloroform, tetrahydrofuran, or acetonitrile. 10 is C 1-6It can be synthesized by reacting an alkyl group with a halogenating agent such as N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, or bromine. These transformations are shown in Scheme 14. [ka] Scheme 14
[0081] Alternatively, the compound of formula (I) can be synthesized by reacting the compound of formula (XL) (wherein X is Cl, Br, or I) with the amine of formula (XI) and carbon monoxide in the presence of a catalyst such as [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) and optionally a base such as triethylamine. Compounds of formula (XL) (wherein X is Cl, Br, or I) are obtained from compounds of formula (XLI) (wherein X is independently Cl, Br, or I) in the presence of a base such as Cs2CO3, K2CO3, or NaOtBu and a suitable palladium catalyst such as tetrakistriphenylphosphine palladium, [1,1-bis(diphenylphosphineno)ferrocene]dichloropalladium(II), bis(diphenylphosphine)palladium(II) chloride, palladium chloride, or palladium acetate, in a suitable solvent such as dimethylformamide, dioxane, tetrahydrofuran, ethanol, or water, from compounds of formula (XLI) (wherein X is independently Cl, Br, or I) to compounds of formula (III) (wherein R 6 These are, independently of each other, hydrogen and C 1-6 Alkyl or two R 6 Both are C 3-8 It can be prepared by Suzuki cross-coupling with a cycloalkyl group (which can form a cycloalkyl group). These transformations are shown in Scheme 15. [ka] Scheme 15
[0082] Alternatively, the compound of formula (I) can be used in a peptide coupling transformation using the above conditions, with the compound of formula (XLII) and the compound of formula (XLIII) (wherein X 2The compound of formula (XLII) can be prepared by reaction with a base such as Cs2CO3, K2CO3, or NaOtBu and a suitable palladium catalyst such as tetrakistriphenylphosphine palladium, [1,1-bis(diphenylphosphine)ferrocene]dichloropalladium(II), bis(diphenylphosphine)palladium(II) chloride, palladium chloride, or palladium acetate, in a suitable solvent such as dimethylformamide, dioxane, tetrahydrofuran, ethanol, or water, reacting with the compound of formula (II) (wherein X is Cl, Br, or I) and the compound of formula (XLIV) (wherein R 6 These are, independently of each other, hydrogen and C 1-6 Alkyl or two R 6 Both are C 3-8 It can be prepared by Suzuki cross-coupling of a compound of formula (XLIV) (wherein R is capable of forming a cycloalkyl group). 6 They are hydrogen and C, independently of each other. 1-6 Alkyl or two R 6 Both are C 3-8 Compounds capable of forming cycloalkyl groups are prepared by known methods or are commercially available. These conversions are shown in Scheme 16. [ka] Scheme 16
[0083] 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
[0084] Alternatively, the compound of formula (Ib) where Z is S can be used in a peptide coupling transformation using the above conditions, with the compound of formula (XLIIb) and the compound of formula (XLIII) (wherein X 2It can be prepared by reaction with (where is OH). The compound of formula (XLIIb) can be prepared by reacting the compound of formula (XLII) 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
[0085] It will be understood by those skilled in the art that the amide coupling reactions described above between acids, amines, and coupling agents can also be carried out using the corresponding acid chlorides and amines. The conversion of acids to their corresponding acid chlorides is well known to those skilled in the art.
[0086] When the term "compound according to the present invention" is used, it refers to the compound according to the present invention.
[0087] Alternatively, the compounds according to the present invention can be obtained by using standard synthesis 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.
[0088] 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.
[0089] 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.
[0090] Salts of the compounds according to the present invention can be prepared by known methods. For example, acid addition salts of the compounds according to the present invention can be obtained by treatment with a suitable acid or a suitable ion exchange reagent, and salts with a base can be obtained by treatment with a suitable base or a suitable ion exchange reagent.
[0091] Salts of the compounds according to the present invention can be converted to the free compound by conventional methods, acid addition salts can be converted, for example, by treatment with a suitable basic compound or a suitable ion exchange reagent, and salts with a base can be converted, for example, by treatment with a suitable acid or a suitable ion exchange reagent.
[0092] Salts of the compounds according to the present invention can be converted to other salts of the compounds according to the present invention, acid addition salts, for example, other acid addition salts, by methods known to the present invention, for example, by treatment of an inorganic acid salt, such as a silver acetate hydrochloride, with a suitable metal salt of the acid, such as a sodium, barium, or silver salt of the acid, in a suitable solvent (for example, an inorganic salt that forms silver chloride insoluble therein and therefore precipitates from the reaction mixture).
[0093] Depending on the procedure or reaction conditions, the compounds according to the present invention, which have salt-forming properties, can be obtained in free form or in salt form.
[0094] In each case, the compounds according to the present invention, in free form or salt form, and, where appropriate, their tautomers, may exist in one form of possible isomers or as mixtures thereof, depending on the number, absolute and relative configuration of chiral carbon atoms present in the molecule, and / or the stereoconfiguration of non-aromatic double bonds present in the molecule, in the form of pure isomers, such as anticarpone and / or diastereomers, or as stereoisomer mixtures, such as enantiomer mixtures, such as racemic compounds, diastereomer mixtures or racemic compound mixtures; the present invention relates to pure stereoisomers and to all possible isomer mixtures, and in all cases above and below it should be understood in this sense, even when stereochemical details are not specifically described in any case.
[0095] 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.
[0096] Enantiomer mixtures such as racemates obtained by a similar method can be separated into optical enantiomers by known methods, for example by recrystallization from an optically active solvent, by chromatography in a chiral adsorbent, for example by high-performance liquid chromatography (HPLC) in acetylcellulose using a suitable microorganism, by cleavage by a specific immobilized enzyme via the formation of an inclusion compound, for example by using a chiral crown ether into which only one enantiomer is combined, or by conversion to a diastereomer salt, for example by reacting the basic final product racemate with an optically active acid such as a carboxylic acid, for example camphoric acid, tartaric acid, or malic acid, or a sulfonic acid, for example camphor sulfonic acid, and the diastereomer mixture thus obtained can be separated, for example by fractional crystallization based on different solubility, and by the action of a suitable agent, for example a basic agent, to obtain a diastereomer from which the desired enantiomer can be released.
[0097] 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.
[0098] 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.
[0099] 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.
[0100] The compounds according to the present invention and, optionally, their tautomers may be obtained in free form or salt form, and optionally in hydrate form, and / or may contain other solvents, such as solvents that may have been used to crystallize compounds that exist in solid form.
[0101] The following examples illustrate, but are not limiting, the present invention.
[0102] The present invention also provides intermediates useful for the preparation of compounds according to the present invention.
[0103] The following intermediates form further embodiments of the present invention.
[0104] Formula (IV) [ka] (In the formula, Z is O or S, preferably Z is O; R 1a These are hydroxy, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Selected from alkyl groups, preferably R 1a C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy; R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Selected independently of alkyl; preferably, R 1b and R 1c is hydrogen; A 2 CR is independent. 2 or N, provided there are 3 or fewer A 2 is N, preferably two or fewer A 2 is N, preferably one or less A 2N is more preferably four A 2 CR 2 On the condition 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 1 to 3 substituents independently selected from halogen, hydroxyl, and CN; preferably, R 2Hydrogen, 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 from alkoxy, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, 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 is independent. 3 or N; R 3 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkylsulfonyl, amino, C 1-6 Alkylamino, diC 1-6 -alkylamino and C 3-6 Selected from cycloalkylaminos, 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, C 1-6 Alkylsulfonyl, amino, C 1-6 Alkylamino, diC 1-6 -alkylamino and C 3-6 Each of the cycloalkylamino groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; preferably, R 3 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, and C 1-6 Alkoxy-C 1-6 Selected from alkyl, where C 1-6 Alkyl, C 1-6 Alkoxy, and C 1-6 Alkoxy-C 1-6 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl, diC 1-6 Alkylaminocarbonyl-C 1-6 Selected from alkyl and CN, where C1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl and diC 1-6 Alkylaminocarbonyl-C 1-6 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN; preferably, R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy, where C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Each alkoxy group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN; and A 3 and R 4 They can optionally come together to form a ring, more preferably a 5- to 8-membered heteroring, more preferably a 6-membered heteroring. A compound of the same, or its salt or N-oxide.
[0105] Formula (II) [ka] (In the formula, Z is O or S, preferably Z is O; R 1a These are hydroxy, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Selected from alkyl groups; preferably, R 1a is C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy; R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Selected independently of alkyl; preferably, R 1b and R 1c is hydrogen; A 2 CR is independent. 2or N, provided there are 3 or fewer A 2 is N, preferably two or fewer A 2 is N, preferably one or less A 2 N is more preferably four A 2 CR 2 On the condition 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 1-6Each alkylcarbonyl group may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxyl, and CN, preferably R 2 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Selected independently from 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 alkoxy group may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; A 3 CR is independent. 3 or N; R 3 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkylsulfonyl, amino, C 1-6 Alkylamino, diC 1-6 -alkylamino and C 3-6 Selected from cycloalkylamino, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkylsulfonyl, amino, C 1-6 Alkylamino, diC 1-6 -alkylamino and C 3-6 Each of the cycloalkylamino groups may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs, preferably R 3 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, and C 1-6 Alkoxy-C 1-6 Selected from alkyl, where C 1-6 Alkyl, C 1-6 Alkoxy, and C 1-6 Alkoxy-C 1-6 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6Alkylaminocarbonyl-C 1-6 Alkyl, diC 1-6 Alkylaminocarbonyl-C 1-6 Selected from alkyl and CN, where C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl and diC 1-6 Alkylaminocarbonyl-C 1-6 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens and 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; A 3 and R4 They may optionally combine to form a ring, more preferably a 5- to 8-membered complex ring, more preferably a 6-membered complex ring; and X is Cl, Br, or I; A compound of the same, or its salt or N-oxide.
[0106] Formula(XXXVI) [ka] (In the formula, A 1 is CH or N, preferably N; R 1a These are hydroxy, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Selected from alkyl groups, preferably R 1a C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy; R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C1-6 Alkoxy, amino, and NHC(O)C 1-6 Selected independently of alkyl; preferably, R 1b and R 1c is hydrogen; and R 5 C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, diC 1-6 Alkylamino, and C 1-6 Alkyl C 1-6 Selected from alkoxyaminos, where each of the groups may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN); A compound of the same, or its salt or N-oxide.
[0107] Formula (XXXVIII) [ka] (In the formula, A 1 is CH or N, preferably N; R 1a These are hydroxy, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Selected from alkyl groups; preferably, R 1a C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy; R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Selected independently of alkyl; preferably, R 1b and R 1c is hydrogen; R 5 C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, diC 1-6 Alkylamino, and C 1-6 Alkyl C 1-6 Selected from alkoxyaminos, where each of the groups may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN; and R 10 is C 1-6 (It is alkyl.) A compound of the same, or its salt or N-oxide.
[0108] Formula (XL) [ka] (In the formula, A 1 is CH or N, preferably N; R 1a These are hydroxy, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Selected from alkyl groups; preferably, R 1a C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy; R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Selected independently of alkyl; preferably, R 1b and R 1c is hydrogen; R 5 C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6Alkylamino, 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; X is Cl, Br, or I; A compound of the same, or its salt or N-oxide.
[0109] Formula (XVI) [ka] (In the formula, Z is O or S, preferably Z is O; R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Selected independently of alkyl; preferably, R 1b and R 1c is hydrogen; A 2 CR is independent. 2 or N, provided there are 3 or fewer A 2 is N, preferably two or fewer A 2 is N, preferably one or less A 2 N is more preferably four A 2 CR 2 On the condition that; R 2 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C1-6 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 1 to 3 substituents independently selected from halogen, hydroxyl, and CN; preferably, R 2 Hydrogen, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Selected independently from alkoxy, where C 1-6 Alkyl, C1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Each alkoxy group may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; A 3 CR is independent. 3 or N; R 3 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkylsulfonyl, amino, C 1-6 Alkylamino, diC 1-6 -alkylamino and C 3-6 Selected from cycloalkylaminos, 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 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 independently selected from halogens, hydroxyls, and CNs; preferably, R 3 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, and C 1-6 Alkoxy-C 1-6 Selected from alkyl, where C 1-6 Alkyl, C 1-6 Alkoxy, and C 1-6 Alkoxy-C 1-6 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens, hydroxyls, and CNs; R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl, diC 1-6 Alkylaminocarbonyl-C 1-6 Selected from alkyl and CN, where C 1-6 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 1-6Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl and diC 1-6 Alkylaminocarbonyl-C 1-6 Each alkyl group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN; preferably, R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy, where C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Each alkoxy group may be optionally substituted with 1 to 3 substituents independently selected from halogens and CN; Here, A 3 and R 4 They may optionally combine to form a ring, more preferably a 5- to 8-membered complex ring, more preferably a 6-membered complex ring; and X is Cl, Br, or I; A compound of the same, or its salt or N-oxide.
[0110] 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 putrefactive microorganisms or organisms in the agricultural sector and related fields of use. Novel compounds are distinguished by their excellent activity at low application rates, the fact that plants exhibit sufficient tolerance, and their environmental safety. They possess highly useful 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 be used, for example, to suppress or eradicate pathogens appearing on plants or parts of plants (fruits, flowers, leaves, stems, tubers, roots) of different crops of useful plants from plant pathogenic microorganisms, while simultaneously protecting those parts of the plants that will grow later.
[0111] Compounds of formula (I) as defined in the present invention may also be used as fungicides. The term “fungicide” as used herein means a compound that controls, modifies, or prevents the growth of fungi. The term “fungicidal effective amount” means the amount of such compound or combination of such compounds that can produce an effect on the growth of fungi. Controlling or modifying effects include all deviations from natural occurrence, such as death or delay, and prevention includes the formation of barriers or other defenses in or on plants to prevent fungal infection.
[0112] For protection against fungal infections and plant pathogenic fungi occurring in the soil, a mixture of formula (I) as defined in the present invention may also be used as a coating agent for treating plant propagation materials, such as seeds, tubers or grains, or plant cuttings (e.g., rice), such as fruits. The propagation material may be treated with a composition containing a compound of formula (I) as defined in the present invention before planting: for example, seeds may be coated before sowing. The compound of formula (I) as defined in the present invention may also be applied (coated) to grains, either by impregnating the seeds with a liquid formulation or by coating the seeds with a solid formulation. The composition may also be applied to the planting site when the propagation material is planted, for example, in the sowing furrow during sowing. The present invention also relates to such methods for treating plant propagation materials and to plant propagation materials treated in this manner.
[0113] Furthermore, compounds of formula (I) as defined in the present invention can be used in related fields, for example, to control fungi in the protection of industrial materials, including wood and wood-related industrial products, in food storage, and in hygiene management.
[0114] In addition, the present invention may also be used to protect non-biological materials, such as sawn timber, wall coverings, and paints, from fungal attacks.
[0115] Compounds of formula (I) as defined in the present invention, and fungicidal compositions containing them, can be used to control plant diseases caused by broad-spectrum fungal plant pathogens. They are effective in controlling broad-spectrum plant diseases such as those caused by leaf pathogens of ornamental plants, lawns, vegetables, fields, grains, and fruit crops.
[0116] Examples of disease-causing fungi and fungal vectors, as well as plant pathogenic bacteria and viruses, that can be controlled include the following:
[0117] This includes species such as Absidia corymbifera, Alternaria spp., Aphanomyces spp., Ascochyta spp., Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A. niger, and A. terrus, Aureobasidium spp. including A. pullulans, Blastomyces dermatidis, Blumeria graminis, and Bremia lactucaea. Botryosphaeria species such as B. lactucae, B. dothidea, B. obtusa, Botrytis species such as B. cinerea, Candida species such as C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis, Cephaloascus fragrans, Ceratocystis species Cercospora spp., such as C. arachidicola, Cercosporidium personatum, Cladosporium spp., Claviceps purpurea, Coccidioides immitis, Cochliobolus species, Colletotrichum species such as C. musae, Cryptococcus neoformans, Diaporthe spp., Didymella spp., Drecxlera spp., Elsinoe spp. Species of the genus Epidermophyton, species of the genus Erysiphe such as Erwinia amylovora and E. cichoracearum, Fusarium spp., including Eutypa lata, F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, F. solani, Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, and Gloeosporium musarum. musarum), Glomerella cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Helminthosporium spp, Hemileia spp, Histoplasma spp such as H. capsulatum, Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium sedithiosum Mycosphaerella species such as *Mycosphaerella spp.*, *Mycosphaerella spp.*, *Mycosphaerella spp.*, *Mycosphaerella spp.*, *Mycosphaerella spp.*, *Mycosphaerella spp.*, *Mycosphaerella spp.*, *Mycosphaerella spp.*, *Mycosphaerella spp.*, *Mycosphaerella spp.*, *Mycosphaerella spp.*, *Mycosphaerella spp.*), Oncobasidium theobromaeon, Ophiostoma piceae, species of the genus Paracoccidioides, species of the genus Penicillium such as P. digitatum and P. italicum, species of the genus Petriellidium, species of Peronosclerospora such as P. maydis, P. philippinensis and P. sorghi, species of Peronospora, species of Peronospora, Phaeosphaeria nodorum Phytophthora spp. such as Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp., Phoma spp., Phhomopsis viticola, P. infestans, Plasmopara spp. such as P. halstedii, P. viticola, Pleospora spp., Podosphaera spp. such as P. leucotricha, and Polymyxa graminis Pseudomonas species (Pseudomonas spp.), P. cubensis, P. humuli, and other Pseudoperonospora species, Pseudopeziza tracheiphila, P. hordei, P.Puccinia species such as P. recondita, P. striiformis, and P. triticina; Pyrenopeziza species, Pyrenophora species; Pyricularia species such as P. oryzae; Pythium species such as P. ultimum; Ramularia species; Rhizoctonia species; Rhizomucor pusillus; Rhizopus arrhizus; and Rhynchosporium species. Species of the genus *Scedosporium*, such as *S. apiospermum* and *S. prolificans*, and *Schizothyrium pomi*, are included. Species of the genera Sclerotinia, Sclerotium, Septoria (including S. nodorum and S. tritici), Sphaerotheca macularis, Sphaerotheca fusca (Sphaerothorix fuliginea), Sporothorix, Stagonospora nodorum, Stemphylium, Stereum hirsutum, and Thanatephorus cucumeris. *Trichoderma spp.*, including *T. cucumeris*, *Tielaviopsis basicola*, *Tilletia* species, *T. harzianum*, *T. pseudokoningii*, and *T. viride*. Species belonging to the genera Trichophyton, Typhula, Uncinula necator, Urocystis, Ustilago, Venturia (including V. inaequalis), Verticillium, and Xanthomonas.
[0118] 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.
[0119] These pathogens may include the following:
[0120] Phytophthora diseases, such as those caused by Phytophthora capsici, Phytophthora infestans, Phytophthora sojae, Phytophthora fragariae, Phytophthora nicotianae, Phytophthora cinnamomi, Phytophthora citricola, Phytophthora citrophthora, and Phytophthora erythroseptica; and Pythium aphanidermatum and Pythium arenomanes. Pythium diseases, such as those caused by *Pythium arrhenomanes*, *Pythium graminicola*, *Pythium irregulare*, *Pythium sylvaticum*, and *Pythium ultimum*; *Peronospora destructor*, *Peronospora parasitica*, *Plasmopara viticola*, *Plasmopara halstedii*, *Pseudoperonospora cubensis*, *Albugo candida*, and *Sclerophthora macrospora*. Diseases caused by Peronosporales, such as macrospora and Bremia lactucae;Oomycetes, including other species such as Aphanomyces cochlioides, Labyrinthula zosterae, Peronosclerospora sorghi, and Sclerospora graminicola; Ascomycetes, for example; Pleosporales, for example; Stemphylium solani, Stagonospora tainanensis, Spirocaea oleaginea, Setosphaeria turcica, Pyrenochaeta lycoperisici, Pleospora herbarum, Phoma destructiva, Phaeosphaeria herpotrichoides, Phaeocryptocus gaeumannii Ophiosphaerella graminicola, Ophiobolus graminis, Leptosphaeria maculans, Hendersonia creberrima, Helminthosporium triticirepentis, Setosphaeria turcica, Drecxlera glycines, Didymella bryoniae, Cycloconium oleagineum, Corynespora cassiicola, Cochliobolus satibus Pyrenophora sativus, Bipolaris cactivora, Venturia inaequalis, Pyrenophora teres, Pyrenophora tritisi repentisThe Capnodiales order includes species such as Septoria tritici, Septoria nodorum, Septoria glycines, Cercospora arachidicola, Cercospora sojina, Cercospora zeae-maydis, and Cercosporella capsuleae. This includes species such as capsellae and Cercosporella herpotrichoides, Cladosporium carpophilum, Cladosporium effusum, Passalora fulva, Cladosporium oxysporum, Dothistroma septosporum, Isariopsis clavispora, Mycosphaerella fijiensis, Mycosphaerella graminicola, and Mycovellosiella coepkeii. Pseudocercosporella koepkeii, Phaeoisariopsis bataticola, Pseudocercospora vitis, Pseudocercosporella herpotricoidherpotrichoides), Ramularia beticola, Ramularia collo-cygni, Magnaporthales, e.g., Gaeumannomyces graminis, Magnaporthe grisea, Pyricularia oryzae, etc., Diaporthales, e.g., Anisogramma anomala, Apiognomonia errabunda, Cytospora platani, Diaporthe phaseoloru, Discula destructiva, Gnomonia fructicola fructicola), Greeneria uvicola, Melanconium juglandinum, Phomopsis viticola, Sirococcus clavigignenti-juglandacearum, Tubakia dryina, Dicarpella spp., Valsa ceratosperma, and others, such as Actinothyrium graminis, Ascochyta pisi, Aspergillus flavus, Aspergillus fumigatus fumigatus), Aspergillus nidulans, Asperisporium caricae, Blumerierella jaapii, Candida speciesspp.), Capnodium ramosum, Cephaloascus spp., Cephalosporium gramineum, Ceratocystis paradoxa, Chaetomium spp., Hymenoscyphus pseudoalbidus, Coccidioides spp., Cylindrosporium padi, Diplocarpon malae, Drepanopeziza campestris, Elsinoe ampelina, Epicoccum nigrum Brown spot, leaf spot, blast, or canker and / or rot caused by species such as Gloeochinia nigrum, Epidermophyton spp., Eutypa lata, Geotrichum candidum, Gibellina cerealis, Gloeocercospora sorghi, Gloeodes pomigena, and Gloeosporium perennans; Gloeochinia nigrum. Gloeotinia temulenta, Griphospaeria corticola, Kabatiella lini, Leptographium Microsporum, Leptosphaerulinia crassiasca, Lophodermium seditiosum, Marssonina graminicola, Microdochium nivale, Monilinia fructicola, Monographella albescens, Monosporascus cannonballus, Naemacyclus species spp.), Ophiostoma novo-ulmi, Paracoccidioides brasiliensis, Penicillium expansum, Pestalotia rhododendri, Petriellidium spp., Pezicula spp., Phialophora gregata, Phyllachora pomigena, Phymatotrichum omnivora, Physalospora abdita, Plectosporium tabasinum tabacinum), Polyscytalum pustulans, Pseudopeziza medicaginis, Pyrenopeziza brassicae, Ramulisporasorghi), Rhabdocline pseudotsugae, Rhynchosporium secalis, Sacrocladium oryzae, Scedosporium spp., Schizothyrium pomi, Sclerotinia sclerotiorum, Sclerotinia minor; Sclerotium spp., Typhula ishikariensis, Seimatosporium mariae, Lepteutypa cupressi, Septocyta ruborum Ruborum), Sphaceloma perseae, Sporonema phacidioides, Stigmina palmivora, Tapesia yallundae, Taphrina bullata, Thielviopsis basicola, Trichoseptoria fructigena, Zygophiala jamaicensis; Powdery mildews (Erysiphales), for example, Blumeria graminis, Erysiphe polygoni, Uncinula necator, Sphaerotheca frigena fuligena), Podosphaera leucotricha, Podospaera macularis, Golovinomyces cichoracearum, Leveillula tauricaPowdery mildew caused by plants such as *Tetramorium taurica*, *Microsphaera diffusa*, *Oidiopsis gossypii*, *Phyllactinia guttata*, and *Oidium arachidis*; and plants of the order Botryosphaeriales, such as *Dothiorella aromatica*, *Diplodia seriata*, *Guignardia bidwellii*, *Botrytis cinerea*, *Botryotinia allii*, *Botryotinia fabae*, and *Fusicoccum amygdali*. Molds caused by amygdali, Lasiodiplodia theobromae, Macrophoma theicola, Macrophomina phaseolina, Phyllosticta cucurbitacearum, etc.; Glommerelales, for example, Colletotrichum gloeosporioides, Colletotrichum lagenarium, Colletotrichum gossypii, Glomerella cingulata, and Colletotrichum gramincola Anthracnose caused by species such as graminicola; and Hypocreales, such as Acremonium strictum, Claviceps purpurea, and Fusarium curmorum.Fusarium culmorum, Fusarium graminearum, Fusarium virguliforme, Fusarium oxysporum, Fusarium subglutinans, Panama disease bacterium (Fusarium oxysporum f.sp.cubense), Gerlachia nivale, Gibberella fujikuroi, Gibberella zeae, Gliocladium spp., Myrothecium verrucaria, Nectria ramulariae, Trichoderma viride Wilt disease or canker disease caused by plants such as viride, Trichothecium roseum, and Verticillium theobromae. smut fungi, including those caused by the Basidiomycete class, such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, Ustilago zeae, and other species of the Ustilaginales order; for example, Cerotelium fici, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, and Puccinia graminis. Puccinia graminis), Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia striiformis f.sp. Hordei, Puccinia striiformis f.sp. cecalisPucciniales, including species such as Secalis, Pucciniastrum coryli, Cronartium ribicola, Gymnosporangium juniperi-viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor, and Uromyces viciae-fabee. Caused by species of the order Uredinales, such as viciae-fabae; as well as species of the genera Cryptococcus, Exobasidium vexans, Marasmiellus inoderma, and Mycena.), Sphacelotheca reiliana, Typhula ishikariensis, Urocystis agropyri, Itersonilia perplexans, Corticium invisum, Laetisaria fuciformis, Waitea circinata, Rhizoctonia solani (rice sheath blight fungus), Thanetephorus cucurmeris (sugar beet root rot fungus), Entyloma dahliae, Entylomella microspora, Neovossia molliniae Other rot and disease, such as those caused by *Tilletia moliniae* and *Tilletia caries*. Blastocladiomycetes, such as Physoderma maydis. Mucoromycete species, such as Choanephora cucurbitarum, Mucor spp., and Rhizopus arrhizus. Furthermore, diseases caused by other species and genera closely related to those listed above.
[0121] In addition to their fungicidal activity, the compounds and compositions comprising the compound of formula (I) as defined in this invention may also be active against bacteria such as Erwinia amylovora, Erwinia caratovora, Xanthomonas campestris, Pseudomonas syringae, Streptomyces scabies and other related species, as well as certain protozoa.
[0122] Within the scope of the present invention, target crops and / or useful plants to be protected are typically berry plants, e.g., blackberries, blueberries, cranberries, raspberries and strawberries; cereals, e.g., barley, corn, millet, oats, rice, rye, sorghum, rye and wheat; fiber plants, e.g., cotton, flax, hemp, jute and sisal; crops, e.g., sugar and fodder beets, coffee, hops, mustard, rapeseed (canola), poppies, sugarcane, sunflowers, tea and tobacco; fruit trees, e.g., apples, apricots, avocados, bananas, cherries, citrus fruits, nectarines, peaches, pears and plums; grasses, e.g., Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St. Augustine grass and zoysia grass; herbs, e.g., basil, borage, chives, coriander, lavender, lavage, mint, oregano, parsley and rosemary , sage and thyme; legumes, e.g., kidney beans, lentils, peas and soybeans; nuts, e.g., almonds, cashews, peanuts, hazelnuts, peanuts, pecans, pistachios and walnuts; palms, e.g., oil palm; ornamental plants, e.g., flowers, shrubs and trees; other trees, e.g., cocoa, coconut, olive and rubber; vegetables, e.g., asparagus, eggplant, broccoli, cabbage, carrots, cucumbers, garlic, lettuce, mallow, melon, okra, onions, pepper, potatoes, pumpkins, rhubarb, spinach and tomatoes; and climbing plants, e.g., grapes, including perennial and annual crops.
[0123] Useful plants and / or target crops according to the present invention include conventional varieties as well as genetically enhanced or genetically modified varieties, such as those with insect resistance (e.g., Bt. and VIP varieties), disease resistance, herbicide tolerance (e.g., glyphosate and glufosinate-tolerant maize varieties, commercially available under trade names RoundupReady® and LibertyLink®), and nematode resistance. Examples of suitably genetically enhanced or genetically modified varieties include the Stoneville 5599BR cotton and Stoneville 4892BR cotton varieties.
[0124] The terms “useful plants” and / or “target crops” should be understood to also include useful plants that have been conferred resistance to herbicides such as bromoxynil or several herbicides (e.g., HPPD inhibitors, ALS inhibitors such as primisulfuron, prosulfuron, and trifloxysulfuron, EPSPS (5-enol-pyruvir-sikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors, or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional breeding methods or genetic engineering. An example of a crop conferred resistance to imidazolinones, such as imazamox, by conventional breeding (muta introduction) methods is Clearfield® summer rapeseed (canola). Examples of crops that have been genetically modified to be resistant to herbicides or several herbicides include glyphosate- and glufosinate-resistant maize varieties that are commercially available under the trade names RoundupReady®, Herculex I®, and LibertyLink®.
[0125] The terms “useful plants” and / or “target crops” should be understood to include those that naturally exhibit or are conferred resistance to harmful insects. This includes plants transformed by the use of recombinant DNA technology to enable the synthesis, for example, one or more selectively acting toxins, such as those known from toxin-producing bacteria. Examples of toxins that can be expressed include δ-endotoxin, vegetative insecticidal protein (Vip), insecticidal protein from nematode-symbiotic bacteria, and toxins produced by scorpions, arachnids, wasps, and fungi. An example of a crop modified to express Bacillus thuringiensis toxin is Bt maize KnockOut® (Syngenta Seeds). An example of a crop containing two or more genes encoding insecticidal resistance and thus expressing two or more toxins is VipCot® (Syngenta Seeds). Crops or their seed materials can also possess resistance to multiple types of pests (so-called superimposed transgenic events when genetically modified). For example, plants can be herbicide resistant and express insecticidal proteins at the same time, such as Herculex I® (Dow AgroSciences, Pioneer Hi-Bred International).
[0126] 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. 0392225). Examples of such antipathogenic substances and transgenic plants capable of synthesizing such antipathogenic substances are known, for example, from European Patent Application Publication No. 0392225, International Publication No. 95 / 33818 and European Patent Application Publication No. 0353191. Methods for producing such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above.
[0127] 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 (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, corn Examples include ribosomal inactivating proteins (RIPs) such as locosin-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 channel blockers; juvenile hormone esterase, diuretic hormone receptor, stilbenzyl synthase, bibenzyl synthase, chitinase, and glucanase.
[0128] Furthermore, it should be understood that in connection with the present invention, there exist δ-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or plant insecticidal proteins (Vip), such as Vip1, Vip2, Vip3, or Vip3A, as well as explicitly hybrid toxins, cleavage toxins, and modified toxins. Hybrid toxins are produced by recombinant synthesis through novel combinations of different domains of these proteins (see, for example, International Publication No. 02 / 15701). Cleavage toxins, such as cleavage Cry1Ab, are known. In the case of modified toxins, one or more amino acids of a naturally occurring toxin are replaced. In such amino acid substitutions, preferably, a protease recognition sequence that does not naturally exist is inserted into the toxin; for example, in the case of Cry3A055, a cathepsin-G recognition sequence is inserted into the Cry3A toxin (see International Publication No. 03 / 018810).
[0129] Additional 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.
[0130] The processes for preparing such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparations are known, for example, from International Publication No. 95 / 34656, European Patent Application Publication No. 0367474, European Patent Application Publication No. 0401979, and International Publication No. 90 / 13651.
[0131] Toxins contained in transgenic plants confer resistance to harmful insects. Such insects can exist in any insect taxonomy, but are typically found in beetles (Coleoptera), diptera, and butterflies (Lepidoptera).
[0132] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known, and some of them are commercially available. Examples of such plants include: YieldGard® (maize variety expressing Cry1Ab toxin); YieldGard Rootworm® (maize variety expressing Cry3Bb1 toxin); YieldGard Plus® (maize variety expressing Cry1Ab and Cry3Bb1 toxins); Starlink® (maize variety expressing Cry9C toxin); Herculex I® (maize variety expressing Cry1Fa2 toxin and the enzyme phosphinothrysin N-acetyltransferase (PAT) to achieve resistance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety expressing Cry1Ac toxin); Bollgard I® (cotton variety expressing Cry1Ac toxin); Bollgard These include II (registered trademark) (cotton varieties expressing Cry1Ac and Cry2Ab toxins); VipCot (registered trademark) (cotton varieties expressing Vip3A and Cry1Ab toxins); NewLeaf (registered trademark) (potato varieties expressing Cry3A toxin); NatureGard (registered trademark), Agrisure (registered trademark) GT Advantage (GA21 glyphosate-tolerant trait), Agrisure (registered trademark) CB Advantage (Bt11 corn borer (CB) trait), and Protecta (registered trademark).
[0133] Further examples of such transgenic crops are as follows: 1. Bt11 maize, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31, 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. This is genetically modified maize (Zea mays) conferring resistance to attacks by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of the cleavage-type Cry1Ab toxin. Bt11 maize has also acquired resistance to the herbicide glufosinate ammonium by transgenic expression of the enzyme PAT. 2. Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. Bt176 maize, registration number C / FR / 96 / 05 / 10. Genetically modified maize (Zea mays) conferred resistance to attacks by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of Cry1Ab toxin. Bt176 maize has also acquired resistance to the herbicide glufosinate ammonium through transgenic expression of the enzyme PAT. 3. Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, MIR604 maize, registration number C / FR / 96 / 05 / 10. Maize conferred insect resistance by transgenic expression of modified Cry3A toxin. This toxin is Cry3A055, modified by insertion of a cathepsin-G-protease recognition sequence. Preparation of such transgenic maize plants is described in International Publication No. 03 / 018810. 4. Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. MON 863 maize, registration number C / DE / 02 / 9. MON 863 expresses the Cry3Bb1 toxin and is resistant to certain Coleoptera insects. 5. Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. IPC 531 cotton, registration number C / ES / 96 / 02. 6. 1507 maize, registration number C / NL / 00 / 10, manufactured by Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium. Genetically modified maize for the expression of the protein Cry1F to acquire resistance to certain Lepidoptera insects and the PAT protein to acquire resistance to the herbicide glufosinate ammonium. 7. NK603×MON810 maize, registered under registration number C / GB / 02 / M3 / 03, manufactured by Monsanto Europe, SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. This is a conventional hybrid maize variety resulting from the cross between the genetically modified variety NK603 and MON 810. NK603×MON 810 maize genetically modifies and expresses the protein CP4 EPSPS, obtained from the Agrobacterium sp. strain CP4, which confers resistance to the herbicide Roundup® (which contains glyphosate), and the Cry1Ab toxin, obtained from Bacillus thuringiensis subsp. kurstaki, which provides resistance to certain Lepidoptera, including the European corn borer.
[0134] As used herein, the term “habitat” means cultivated land on which plants grow, or on which seeds of cultivated plants are sown, or on which seeds will be sown in the soil. It includes soil, seeds and seedlings, and established vegetation.
[0135] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves, and fruits.
[0136] The term "plant propagation material" is understood to refer to plant materials, such as seeds and other reproductive parts, as well as cuttings or tubers, that can be used for plant propagation, such as potatoes. Examples include plant seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, and parts. Germinated plants and seedlings that will be transplanted after germination or emergence from the soil may also be included. These seedlings may be protected before transplantation by full or partial treatment by immersion. Preferably, "plant propagation material" is understood to mean seeds.
[0137] The pesticides referred to herein by their common names are publicly known, for example, from "The Pesticide Manual," 19th Ed., British Crop Protection Council 2021.
[0138] Compounds of formula (I) as defined in this invention may be used in their unmodified form or, preferably, in combination with auxiliaries conventionally used in the art of formulation. For this purpose, they may be appropriately formulated by known methods into emulsifiable concentrates, coating pastes, ready-to-spray or dilutable solutions or suspensions, diluted emulsions, wettable powders, soluble powders, powders for spraying, granules, and also, for example, encapsulations in polymeric substances. As with the type of composition, the method of application, such as spraying, misting, powdering, granulation, coating or pouring, is selected according to the intended purpose and the circumstances at hand. The composition may also contain further auxiliaries such as stabilizers, defoamers, viscosity modifiers, binders or tackifiers, as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.
[0139] For example, suitable carriers and / or auxiliaries for agricultural applications may be solids or liquids and are substances useful in formulation techniques, such as natural or recycled inorganic substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders, or fertilizers. Such carriers are described, for example, in International Publication No. 97 / 33890.
[0140] A suspension concentrate is an aqueous formulation in which finely ground solid particles of an active compound are suspended. Such formulations contain anti-settling agents and dispersants, and may further contain wetting agents, defoaming agents, and crystal growth inhibitors to enhance activity. When used, these concentrates are diluted with water and typically applied as a spray to the area to be treated. The amount of the active ingredient may range from 0.5% to 95% of the concentrate.
[0141] 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.
[0142] Emulsifying concentrates are homogeneous liquid compositions that are dispersible in water or other liquids and may consist solely of an active compound and a liquid or solid emulsifier, or they may also contain liquid carriers such as xylene, high-boiling aromatic naphtha, isophorone, and other non-volatile organic solvents. When used, these concentrates are dispersed in water or other liquids and are typically applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.
[0143] 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 dioxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate, and other organic or inorganic materials that can absorb or be coated with the active compound. Granular formulations typically contain 5% to 25% active ingredients, which may include surfactants such as heavy aromatic naphtha, kerosene and other petroleum fractions, or vegetable oils; and / or stickers such as dextrin, glue or synthetic resins.
[0144] Powder for scattering is a free-flowing mixture of an active ingredient and finely ground solids such as talc, clay, powder, and other organic and inorganic solids that act as a dispersant and carrier.
[0145] Microcapsules are typically droplets or granules of an active ingredient encapsulated in an inert, porous shell that allows for the release of the encapsulated material into the surroundings at a controlled rate. Encapsulated droplets are typically 1 to 50 microns in diameter. The encapsulated liquid typically constitutes 50 to 95% of the capsule's weight and may include a solvent in addition to the active compound. Encapsulated granules are generally porous granules having a porous membrane that seals the pore openings of the granules, retaining the active species in liquid form within the granular pores. Granules are typically in the range of 1 millimeter to 1 centimeter in diameter, preferably 1 to 2 millimeters. Granules are formed by extrusion, agglomeration, or prilling, or they exist naturally. Examples of such materials include vermiculite, calcined clay, kaolin, attapulgite clay, sawdust, and granular carbon. Shell or membrane materials include natural and synthetic rubber, cellulosic materials, styrene-butadiene copolymers, polyacrylonitrile, polyacrylates, polyesters, polyamides, polyureas, polyurethanes, and starch xanthetes.
[0146] Other useful formulations for agricultural applications include simple solutions of the active ingredient in a solvent in which the active ingredient is completely dissolved at the desired concentration, such as acetone, alkylated naphthalene, xylene, and other organic solvents. Pressurized sprayers may also be used, in which the active ingredient is dispersed in a finely pulverized form as a result of evaporation of a low-boiling point dispersible solvent carrier.
[0147] Suitable agricultural additives and / or carriers useful for formulating the compositions of the present invention in the above-mentioned formulation types are well known to those skilled in the art.
[0148] Examples of liquid carriers that can be used include water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetate, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidinone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-Trichloroethane, 2-Heptanone, Alpha-pinene, d-Limonene, Ethylene glycol, Ethylene glycol butyl ether, Ethylene glycol methyl ether, γ-Butyrolactone, Glycerol, Glycerol diacetate, Glycerol monoacetate, Glycerol triacetate, Hexadecane, Hexylene glycol, Isoamyl acetate, Isobornyl acetate, Isooctane, Isophorone, Isopropylbenzene, Isopropyl myristate, Lactic acid, Laurylamine, Mesityl oxide, Methoxypropanol, Methyl isoamyl ketone, Methyl isobutyl ketone, Methyl laurate, Methyl octanoate, Methyl oleate, Methylene chloride, m-Xylene, n-Hexane, n-Octylamine, Octadeca Examples include sodium phosphate, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol and amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol and other high molecular weight alcohols, ethylene glycol, propylene glycol, glycerin and N-methyl-2-pyrrolidinone. Water is generally the optimal carrier for diluting concentrates.
[0149] Suitable solid carriers include, for example, talc, titanium dioxide, pyroferrite clay, silica, attapulgite clay, diatomaceous earth (kieselguhr), white pigment, diatomaceous earth (diatomaxeous earth), lime, calcium carbonate, bentonite clay, fuller's earth, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, and lignin.
[0150] A wide range of surfactants are advantageously used in both the liquid and solid compositions, particularly those designed to be diluted with a carrier before application. These agents, when used, typically constitute 0.1% to 15% by mass of the formulation. They may be anionic, cationic, nonionic, or polymeric in nature, and can be used as emulsifiers, wetting agents, suspending agents, or for other purposes. Typical surfactants include alkyl sulfate salts, e.g., diethanolammonium lauryl sulfate; alkylaryl sulfonates, e.g., calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, e.g., nonylphenol-C.sub.18 ethoxylate; alcohol-alkylene oxide addition products, e.g., tridecyl alcohol-C.sub.16 ethoxylate; soaps, e.g., sodium stearate; alkylnaphthalene sulfonate salts, e.g., sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, e.g., sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, e.g., sorbitol oleate; quaternary amines, e.g., lauryltrimethylammonium chloride; polyethylene glycol esters of fatty acids, e.g., polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono and dialkyl phosphate esters.
[0151] 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.
[0152] In addition, other biocides or compositions may be combined with the composition of the present invention and used in the method of the present invention, and may be applied simultaneously with or sequentially to the composition of the present invention. When applied simultaneously, these further active ingredients may be compounded together with the composition of the present invention or mixed, for example, in a spray tank. These further biocides may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides, plant growth regulators, and / or biological formulations.
[0153] The following combinations of the compound of formula I and another active substance in a 1:1 weight ratio are preferred (where the abbreviation "TX" means "one compound selected from the compounds defined in Tables 1.1 to 1.297 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-Jib Romo-3-chloropropane + TX, 1,2-dichloropropane + TX, 1,2-dichloropropane and 1,3-dichloropropane + TX, 1,3-dichloropropane + TX, 14-methyloctadeca-1-ene + TX, 1-hydroxy-1H-pyridine-2-thione + TX, 2-(octylthio)ethanol + TX, 2-chlorophenyl N-methylcarbamate (CPMC) + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide + 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-ylacetic acid + TX, 6-isopentenylaminopurine + TX, 8-hydroxyquinoline sulfate + TX, abamectin + TX, acequinosyl + TX, acetamiprid + TX, acetoprole + TX, acrinatrin + TX, acinonapyr + TX, Adoxophyes orana GV + TX, afidopiropene + TX, afoxolaner + TX, Agrobacterium radiobacter + TX,AKD-3088+TX, Aranicarb+TX, Aldicarb+TX, Aldoxycarb+TX, Allethrin+TX, α-Cypermethrin+TX, Alphamethrin+TX, Alpha-Multistriatin+TX, Amblyseius spp.+TX, Amidoflumet+TX, Amino Acids+TX, Aminocarb+TX, Anagrapha falcifera NPV+TX, Anagrus atomus+TX, Aphelinus abdominalis+TX, Aphidius colemani+TX, Aphidoletes Aphidimyza+TX, Apholate+TX, Autographa californica NPV+TX, AZ 60541+TX, Azadirachtin+TX, Azocyclotin+TX, Bacillus aizawai+TX, Bacillus chitinosporus AQ746 (NRRL accession number B-21 618)+TX, Bacillus firmus+TX, Bacillus kurstaki+TX, Bacillus mycoides AQ726 (NRRL accession number B-21664)+TX, Bacillus pumilus (NRRL accession number B-30087)+TX, Bacillus pumilus AQ717 (NRRL accession number B-21662)+TX, Bacillus sp. AQ175 (ATCC accession number 55608)+TX, Bacillus sp. AQ177 (ATCC accession number 55609)+TX, Bacillus sp. AQ178 (ATCC accession number 53522)+TX, Bacillus sphaericus Neide+TX,Bacillus subtilis AQ153 (ATCC accession number 55614) + TX, Bacillus subtilis AQ30002 (NRRL accession number B-50421) + TX, Bacillus subtilis AQ30004 (NRRL accession number B-50455) + TX, Bacillus subtilis AQ713 (NRRL accession number B-21661) + TX, Bacillus subtilis AQ743 (NRRL accession number B-21665) + TX, Bacillus subtilis (details unknown) + TX, Bacillus thuringiensis AQ52 (NRRL Accession number B-21619)+TX, Bacillus thuringiensis BD#32 (NRRL Accession number B-21530)+TX, Bacillus thuringiensis Berliner+TX, Bacillus thuringiensis subsp. Aizawai+TX, Bacillus thuringiensis subsp. Israelensis+TX, Bacillus thuringiensis subsp. Japonensis+TX, Bacillus thuringiensis subsp. kurstaki+TX, Bacillus thuringiensis subsp. tenebrionis (Bacillus Bacillus thuringiensis subsp. Tenebrionis) + TX, Bacillus thuringiensis subspec. kurstaki BMP 123 + TX, Beauveria bassiana + TX,Beauveria brongniartii + TX, Bencrotiaz + TX, Benomyl + TX, Bensultap + TX, Benzoximate + TX, Benzpyrimoxane + TX, Beta-cyfluthrin + TX, Beta-cypermethrin + TX, Betoxazine + TX, Bifenazet + TX, Bifenthrin + TX, Binapacril + TX, Biorethrin + TX, Biorethmethrin + TX, Bis(tributyltin) oxide + TX, Bisagil + TX, Bistriflurone + TX, Bisulfurfen + TX, Brevicomin + TX, Proflanilide + TX, Broflusli Nate + TX, Bromoacetamide + TX, Bromophos-ethyl + TX, Bronopol + TX, Busulfan + TX, Butocarboxime + 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: 16 32218-00-8+TX, CAS number: 1808115-49-2+TX, CAS number: 1922957-46-7+TX, CAS number: 1922957-48-9+TX, CAS number: 1956329-03-5+TX, CAS number: 1990457-52-7+T X, CAS number: 1990457-55-0+TX, CAS number: 1990457-57-2+TX, CAS number: 1990457-66-3+TX, CAS number: 1990457-77-6+TX, CAS number: 1990457-85-6+TX, CAS number: 2032 403-97-5+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 No.: 2133042-44-9+TX, CAS No.: 2171099- 09-3+TX, CAS number: 2220132-55-6+TX, CAS number: 2396747-83-2+TX, CAS number: 2408220-91-5+TX, CAS number: 2408220-94-8+TX, CAS number: 2415706:16-8+TX, piperfuranilide (CAS number: 2615135-05-0)+TX, CAS number: 2719848-60-7+TX, CAS number: RNA (Leptinotarsa desemlineata (Leptinotarsa (Decemlineata)-Specific Recombinant Double-Strand Interference GS2)+TX, Chlorantraniliprole+TX, Chlordane+TX, Chlorfenapyr+TX, Chloropicrin+TX, Chloroprallethrin+TX, Chlorpyrifos+TX, Chromafenozide+TX, Chrysoperla carnea+TX, Clempyrin+TX, Chloetocarb+TX, Clothianidin+TX, Codrelle+TX, Codremon+TX, Copper Acetoarsenite+TX, Copper Dioctanoate+TX, Copper Hydroxide+TX, Copper Sulfate+TX, Cresol+TX, Clufomate+TX, Cryptolaemus montorgiensis montrouzieri)+TX, Kyurua+TX, Cyanophenphos+TX, Cyantraniliprole+TX, Sibutrin+TX, Cyclaniliprole+TX, Cyclobtriflurum+TX, Cycloprotrin+TX, Cycloxapride+TX, Cydia pomonella GV+TX, Cyenopyrafen+TX, Cietopyrafen+TX, Cyflumetofen+TX, Cyfluthrin+TX, Cyhalodiamide+TX, Cylohalothrin+TX, Cypermethrin+TX, Cyphenothrin+TX, Cypuprofuranilide+TX, Cyromazine+TX, Cytokinin+TX, Dacnusa sibirica sibirica)+TX, dazomet+TX, DBCP+TX, DCIP+TX, deltamethrin+TX, diafenthiuron+TX, dialiphos+TX, diamidaphos+TX, dibrom+TX, dibutyl adipate+TX, dibutyl phthalate+TX, dibutyl succinate+TX, diclofenthion+TX, diclofenthion+TX, diclofenthion+TX, dichlorophene+TX, dicliphos+TX, dichloromesothiaz+TX,Diethyltoluamide + TX, Diflubenzuron + TX, Diglyphus isaea + TX, Dimatif + TX, Dimethoate + TX, Dimethylcalvert + TX, Dimethyl phthalate + TX, Zinpropyridaz + TX, Dinactin + TX, Dinocap + TX, Dinotefuran + TX, Dioxabenzophos + TX, Dipirithione + TX, Disparure + TX, D-Limonene + TX, Dodeca-8-en-1-ylacetate + TX, Dodeca-9-en-1-ylacetate + TX, Dodeca-8,10-dien-1-ylacetate + TX, Dodicine + TX, Dominicalle + TX, Doramectin + TX, Emamectin + TX, Emamectin benzoate + TX, Empenthrin + TX, Encarsia formosa Formosa + TX, Endotar + TX, Endrin + TX, Eprinomectin + TX, Epsilon-Monfluorothrin + TX, Epsilon-Metofluthrin + TX, Eretmocerus eremicus + TX, Esfenvalerate + TX, Ethion + TX, Ethiprole + TX, Etoprophos + TX, Ethyl 4-Methyloctanoate + TX, Ethylhexanediol + TX, Dibromethylene + TX, Etofenprox + TX, Ethoxazole + TX, Etopylafen + TX, Eugenol + TX, Seaweed extract and molasses-derived fermented product + TX, Seaweed extract and molasses-derived fermented product containing urea + TX, Seaweed extract and fermented plant product + TX, Seaweed extract and fermented plant product containing plant hormones, vitamins, EDTA-chelated copper, zinc, and iron + TX, Famfu Lu+TX, Phenaminosulf+TX, Phenamiphos+TX, Phenazaquin+TX, Fenflusrin+TX, Fenitrothion+TX, Fenmezoditiaz+TX, Phenobucarb+TX, Phenothiocarb+TX, Phenoxycarb+TX, Fenpropathrin+TX, Fenpyrad+TX, Fenpyroximate+TX, Fensulfothion+TX, Fenthion+TX, Fentin+TX, Fentin acetate+TX, Fenvalerate+TX, Iron(III) phosphate+TX, Fipronil+TX, Flomethoquin+TX, Flonicamide+TX, Fluacrypyrim+TX, Fluazaindridin+TX,Fluazuron + TX, Flubendiamide + TX, Flubendimine + TX, Fluchlordiniliprole + TX, Flucitrinate + TX, Flucycloxuron + TX, Flucythrinate + TX, Fluensulfone [318290-98-1] + TX, Fluensulfone + TX, Fluphenelim + TX, Flufenprox + TX, Flufiprole + TX, Fluhexaphon + TX, Flumethrin + TX, Fluopyram + TX, Flupyradiflon + TX, Flupyrimine + TX, Flupyroxytribin + TX, Fluralaner + TX, Fluvalinate + TX, Fluxametham Do+TX, Formaldehyde+TX, Fostiazate+TX, Fostiethane+TX, Frontalin+TX, Furfural+TX, Gamma-cyhalotrin+TX, Gossyplure(registered trademark) (1:1 mixture of (Z,E) and (Z,Z) isomers of hexadeca-7,11-dien-1-yl acetate)+TX, Grandolure+TX, Grandolure I+TX, Grandolure II+TX, Grandolure III+TX, Grandolure IV+TX, Granulosis virus+TX, Guadipyr+TX, GY-81+TX, Halfenprox+TX, Halofenozide+TX, Harpin+TX, Helicoverpa almigera Heliothis punctigera (Nuclear Polyhedrosis Virus) + TX, Helicoverpa zea (NPV) + TX, Helicoverpa zea (Nuclear Polyhedrosis Virus) + TX, Heliothis punctigera (Nuclear Polyhedrosis Virus) + TX, Heliothis virescens (Nuclear Polyhedrosis Virus) + TX, Hemel + TX, Hempa + TX, Heptafluthrin + TX, Heterophos + TX, Heterorhabditis bacteriophora and H. megidis + TX, Hexalua + TX, Hexamide + TX, Hexithiazox + TX, Hippodamia conbergensis (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, Iposenol + TX, Isamidophos + TX, Isazofos + TX, Isocycloseram + TX, Isoflualanum (CAS number: 2892524-05-7) + TX, Isothioate + TX, Ivermectin + TX, Japonilua + TX, Kappa-bifenthrin + TX, Kappa-tefluthrin + TX, Kasugamycin + TX, Kasugamycin hydrochloride hydrate + TX, Kinetin + TX, Lambda-cyhalotrin + TX, Redoprona + TX, Lepimectin + TX, Leptomastix Dactylopia dactylopii)+TX, lineatin+TX, liturua+TX, lupurua+TX, rotilaner+TX, lufenuron+TX, Macrolophus caliginosus+TX, Mamestra brassicae NPV+TX, mecarfone+TX, medolua+TX, megatomoic acid+TX, metaflumizone+TX, metaldehyde+TX, metam+TX, metam-potassium+TX, metam-sodium+TX, Metaphycus helvolus+TX, Metarhizium anisopliae var. acridum+TX, Metarhizium anisopliae var. anisopliae var. anisoopliae)+TX, Metarhizium spp.+TX, Metepa+TX, Methiocarb+TX, Methiotepa+TX, Methomyl+TX, Methquin-butyl+TX, Methoxyphenozide+TX, Methylphorate+TX, Methyl bromide+TX, Methyl eugenol+TX, Methyl isothiocyanate+TX, Methylneodecanamide+TX, Metofluthrin+TX, Metocarb+TX, Mexacalbate+TX, Milbemectin+TX, Milbemycin oxime+TX, Monfluorothrin+TX, Morzide+TX, Moxidectin+TX, Muscarle+TX,Muscodor albus 620 (NRRL accession number 30547) + TX, Muscodor roseus A3-5 (NRRL accession number 30548) + TX, Myrothecium verrucaria composition + TX, Naabam + TX, NC-184 + TX, Neem tree-based products + TX, Neodiprion certifer 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, Oryctalure + TX, Ostramonone + TX, Oxamate + TX, Oxamyl + TX, Oxazosulfyl + TX, Oxolinic acid + TX, Oxytetracycline + TX, Paecilomyces fumosoroseus fumosoroseus)+TX, Paecilomyces lilacinus+TX, parathion-ethyl+TX, Pasteuria nishizawae+TX, Pasteuria penetrans+TX, Pasteuria ramosa+TX, Pasteuria thornei+TX, Pasteuria usgae+TX, P-cymene+TX, penflurone+TX, pentachlorophenol+TX, permethrin+TX, phenothrin+TX, phorate+TX, phosphamidone+TX, phosphocarb+TX, Phytoseiulus persimilis persimilis) + TX, picaridin + TX, pioxaniliprole + TX, piperazine + TX, piperonyl butoxide + TX,Pyrimicalb + TX, Pyrimifos-ethyl + TX, Pyrimifos-methyl + TX, Plutella xylostella granuloma virus + TX, Plutella xylostella nuclear polyhedrosis virus + TX, nuclear polyhedrosis virus + TX, potassium and molybdenum and EDTA-chelated manganese + TX, Potassium ethylxanthogenic acid + TX, potassium hydroxyquinoline sulfate + TX, prallethrin + TX, probenazole + TX, profenofos + TX, profluthrin + TX, propargit + TX, propethamphos + TX, propoxul + TX, prothiofos + TX, protrefene bute + TX, piflubmid + TX, pymetrozine + TX, pyraclofos + 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 mixture) + TX, QRD 452 (terpenoid mixture) + TX, QRD 460 (terpenoid mixture) + TX, Quillaya saponaria + TX, Quinoclamine + TX, Quinonamide + TX, Resmethrin + TX, Rhodococcus globerulus AQ719 (NRRL accession number B-21663) + TX, Saloraner + TX, S-Biorethrin + TX, Cebuphos + TX, Selamectin + TX, Siguru + TX, Silafluofen + TX, Simazine + TX, Sodium pentachlorophenoxide + TX, Solzidine + TX, Spidoxamato + TX, Spinetoram + TX, Spinosad + TX, Spirobudiphen + TX, Spirodiclofen + TX, Spiromesifen + TX, Spiropidione + TX, Spirotetramato + TX, Spodoptera exigua exigua) multicapsid polyhedrosis virus + TX, Spodoptera frugiperda polyhedrosis virus + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema feltiae + TX, Steinernema glaseri + TX, Steinernema riobrave (Steinernemariobrave)+TX, Steinernema riobravis+TX, Steinernema scapterisci+TX, Steinernema spp.+TX, Streptomyces galbus (NRRL accession number 30232)+TX, Streptomyces sp. (NRRL accession number B-30145)+TX, Streptomycin+TX, Streptomycin sesquisulfate+TX, Strychnine+TX, Sulcatol+TX, Sulfiflumin (CAS number: 2377084-09-6)+TX, Sulfoxaflor+TX, Tadimucarb+TX, Tebufenozide+TX, Tebufenpyrad+TX, Tebupirimiphos+TX, Tecrophthalam+TX, Tefluthrin+TX, Temephos+TX, Tepa+TX, Turbam+TX, Terbuphos+TX, Terpenoid mixture+TX, Tetrachlorolantraniliprole+TX, Tetrachlorothiophene+TX, Tetradeca-11-en-1-yl acetate+TX, Tetradiphon+TX, Tetramethrin+TX, Tetramethylfluthrin+TX, Tetranactin+TX, Tetraniliprole+TX, Theta-Sipel Metrine + TX, Thiacloprid + TX, Thiafenox + TX, Thiamethoxam + TX, Thiocyclam + TX, Thiodicarb + TX, Thiofanox + TX, Thiohempa + TX, Thiomersal + TX, Thiometon + TX, Thionadin + TX, Thiophanate + TX, Thiosultap + TX, Thiotepa + TX, Tigolaner + TX, Thiolantraniliprole + TX, Thioxazafen + TX, Tolfenpyrad + TX, Toxafen + TX, Tralomethrine + TX, Transfluthrin + TX, Tretamine + TX, Triazamate + TX, Triazophos + TX, Triazurone + TX, Tributyltin oxide + TX, Trichlorfon + TX, Trichloronate + TX, Trichlorfon + TX, Tricogramma species(spp.) + TX, Triphenmorph + TX, Trifluenfronate + TX, Triflumezopyrim + TX, Trimedrua + TX, Trimedrua A + TX, Trimedrua B1 + TX, Trimedrua B2 + TX, Trimedrua C + TX, Trimetacarb + TX, Triphenyltin acetate + TX, Triphenyltin hydroxide + TX, Tranquol + TX, Cyclopyrazoflor + TX, Typhlodromus occidentalis + TX, Uredepa + TX, Verticillium lecanii + TX, Verticillium spp. + TX, Xylenol + TX, YI-5302 + TX, Zeatin + TX, Zeta-cypermethrin + TX; N-[(1R)-1-benzyl-3-chloro-1-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 from the method described in International Publication No. 2019 / 110427) + TX, (3',4',5'-trifluorobiphenyl-2-yl)-amide + TX, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone (These compounds may be prepared from the method described in International Publication No. 2017 / 220485) + TX, (4-phenoxyphenyl)methyl 2-amino-6-methylpyridine-3-carboxylate (this compound can be prepared from the method described in International Publication No. 2014 / 006945) + TX, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone + TX, (7E,9Z)-dodeca-7,9-diene-1-ylacetate + TX, (9Z,11E)-tetradeca-9,11-diene-1-ylacetate (E)-(3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, (Z)-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 from the method described in International Publication No. 2018 / 153707) + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazole-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide + TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazole-1-yl]acetyl]-4-piperidyl]thiazole- 4-yl]-4,5-dihydroisoxazole-5-yl]-3-chlorophenyl]methanesulfonate + TX, 1-(4,5-dimethylbenzimidazole-1-yl)-4,4,5-trifluoro-3,3-dimethylisoquinoline + TX, 1-(4,5-dimethylbenzimidazole-1-yl)-4,4-difluoro-3,3-dimethylisoquinoline + TX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridine-3-yl)-4,4,5-trifluoro-3,3-dimethylisoquinoline + TX, 1-(6,7-dimethylpyrazolo [1,5-a]pyridine-3-yl)-4,4,6-trifluoro-3,3-dimethylisoquinoline + TX, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridine-3-yl)-4,4-difluoro-3,3-dimethylisoquinoline (these compounds may be prepared from the method described in International Publication No. 2017 / 025510) + TX, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane + TX, 1,2-dibromo-3-chloropropane + TX, 1,2-Dichloropropane and 1,3-Dichloropropane + TX, 1,3-Dichloropropane + TX, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea + TX, 1-[2-[[1-(4-chlorophenyl)pyrazole-3-yl]oxymethyl]-3-methylphenyl]-4-methyltetrazole-5-one + TX, 10-Diene-1-ylacetate + TX, 14-Methyloctadeca-1-ene + TX, 1-Bromo-2-chloroethane + TX, 1-Di Chloro-1-nitroethane + TX, 1-hydroxy-1H-pyridine-2-thione + TX, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea + TX, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazole-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxy Samide + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(1,3-dithiolan-2-yl)phenyldimethylcarbamate + TX, 2-(2-butoxyethoxy)ethylpiperonylate + 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-(difluoro Methyl)-N-(3-ethyl-1,1-dimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethylindan-4-yl]pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethylindan-4-yl]pyridine-3-carboxamide (this compound can be prepared from the method described in International Publication No. 2014 / 095675) + TX, 2-(difluoromethyl)-N-[3-ethyl-1,1-Dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, 2-(octylthio)ethanol + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate + TX, 2,2-dichlorovinyl 2-ethylsulfinylethylmethyl phosphate + TX, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide + TX, 2,4-dichlorophenylbenzenesulfonate + TX, 2,6-dimethyl-1H,5H-[1,4]di Thiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetron (this compound can be prepared from the method described in International Publication No. 2011 / 138281) + TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol + TX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazole-1-yl)propan-2-ol (this compound can be prepared from the method described in International Publication No. 2017 / 029179) (This compound can be prepared from the method described in International Publication No. 2017 / 029179) + TX, 2-chlorovinyl diethyl phosphate + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide + TX, 2-imidazolidone + TX, 2-isovalerylindan-1,3-dione + TX, 2-methyl(propane-2-inyl)aminophenylmethylcarbamate + TX, 2 -Oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide (This compound may be prepared from the method described in International Publication No. 2018 / 065414) + TX, 2-thiocyanatoethyl laurate + TX, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole (These compounds may be prepared from the method described in International Publication No. 2016 / 156085) + TX, 3-(4,4-difluoro-3,4-Dihydro-3,3-dimethylisoquinoline-1-yl)quinolone + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide + TX, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carboninitrile (this compound can be prepared from the method described in International Publication No. 2016 / 156290) + TX, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carboninitrile (this compound can be prepared from the method described in International Publication No. 2016 / 156290) (Can be prepared from the method described in No. 6290) + 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-phenyl Lupyrazole-5-yldimethylcarbamate + TX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine-3-carbonitrile + TX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-2,5-dimethylpyrazole-3-amine + TX, 4-(quinoxaline-2-ylamino)benzenesulfonamide + TX, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazole-1-yl)-3,3-dimethylisoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridine-3-yl)isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridine-3-yl)isoquinoline + TX, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-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-methyl Tirnonan-5-one + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohexa-2-eneone + 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-thiolZinc salt (2:1) + TX, 5-methyl-6-thioxo-1,3,5-thiadiadinane-3-ylacetic acid + TX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methylpyridazine-4-carboxamide (may be prepared from the method described in International Publication No. 2020 / 109391) + TX, 6-chloro-3-(3-cyclopropyl-2-fluoro- Phenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide (which can be prepared from the method described in International Publication No. 2020 / 109391) + TX, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazole-1-yl)isoquinoline + TX, 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl ]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide (which can be prepared from the method described in International Publication No. 2020 / 109391) + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitride + TX, 6-isopentenylaminopurine + TX, 8-fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]- 1,3-dimethyl-butyl]quinoline-3-carboxamide +TX, 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide +TX, 8-hydroxyquinoline sulfate +TX, acetylone +TX, acetoprole +TX, acibenzol +TX, acibenzol-S-methyl +TX, acrylonitrile +TX, Adoxophyes orana GV +TX, Agrobacterium radiobacter +TX, aldoxycarb +TX, aldrin +TX, allosamidin +TX, alixicarb +TX, α-chlorohydrin +TX, α-ecdysone +TX, α-multistriatin +TX, aluminum phosphide +TX, Amblyseius speciesspp.)+TX, amectotractin+TX, ametoctrazine+TX, amidithione+TX, amidothioate+TX, aminocarb+TX, aminopyriphen+TX, amisulbrom+TX, amiton+TX, amiton hydrogen oxalate+TX, amitraz+TX, anabacin+TX, Anagrapha falcifera NPV+TX, Anagrus atomus+TX, ancimidor+TX, anilazine+TX, anisifuruprin+TX, anthraquinone+TX, antu+TX, Aphelinus abdominalis+TX, Aphidius colemani+TX, Aphidoletes aphidemizer Aphidimyza)+TX, Aphorate+TX, Aramite+TX, Arsenous Acid+TX, Atidathion+TX, Autographa californica NPV+TX, Azaconazole+TX, Azamethiphos+TX, Azobenzene+TX, Azothoate+TX, Azoxystrobin+TX, Bacillus sphaericus Neide+TX, Bacillus thuringiensis Delta Endotoxin+TX, Barium Carbonate+TX, Barium Hexafluoridosilicate+TX, Barium Polysulfide+TX, Bartholin+TX, Bayer 22 / 190+TX, Bayer 22408+TX, Beauveria bronchiniatiibrongniartii)+TX, Benalaxyl+TX, Bencrotiaz+TX, Benomyl+TX, Benoxaphos+TX, Bentiavaricarb+TX, Benzothiostrobin+TX, Benzovindiflupir+TX, Benzyl benzoate+TX, Beta-cyfluthrin+TX, Beta-cypermethrin+TX, Betoxazine+TX, Bioetanomethrin+TX, Biopermethrin+TX, Bis(2-chloroethyl) ether+TX, Bis(tributyltin) oxide+TX, Bisazil+TX, Bisthiosemi+TX, Vitertanol+TX, Bixa Fen+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-inylN-[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, Camfechlor+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: 2344721 -61-3+TX, Sebadin+TX, Quinomethionate+TX, Chloralose+TX, Chlorbenside+TX, Chlorbicurene+TX, Chlordane+TX, Chlordecone+TX, Chlorodimeform+TX, Chlorodimeform hydrochloride+TX, Chlorphenetol+TX, Chlorfensone+TX, Chlorfensulfide+TX, Chlorobenzylate+TX, Chloroform+TX, Chloroinconazide+TX, Chloromebform+TX, Chloromethionone+TX, Chloroneb+TX, Chlorophacinone+TX, Chloropicrin+TX, Chloropropylate+TX, Chlorthalonil+TX, Chlorphoxime+TX, Chlorprazofos+TX, Chlorthiofos+TX, Clozolinate+TX, Cholecalciferol+TX, Chrysoperlacarnea)+TX, Synerin I+TX, Synerin II+TX, Synerin+TX, cismethrin+TX, cis-resmethrin+TX, clocythrin+TX, closantel+TX, kodrelle+TX, kodremon+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 Coumacrol + TX, Coumafuryl + TX, Coumaphos + TX, Coumatetralyl + TX, Cumethoxystrobin (Diaxiangjunzhi) + TX, Cumitoate + TX, Comoxystrobin + TX, Cresol + TX, Crimidine + TX, Crotamiton + TX, Clotoxyphos + TX, Clufomate + TX, Cryolite + TX, Cryptolaemus montorgiensis Montrouzieri) + TX, CS 708 + TX, Kyurua + TX, Cufraneb + TX, Cyanophenphos + TX, Cyanophos + TX, Cyanthoate + TX, Cyazofamide + TX, Sibutrin + TX, Cycloresrin + TX, Cyclobtrifluram + TX, Cydia pomonella GV + TX, Cyflufenaamide + TX, Simiazole + TX, Cymoxanil + TX, Cyproconazole + TX, Cyprodinil + TX, Cithioate + TX, Cytokinin + TX, Dacnusa sibiricasibirica+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 X, Diclofluanide + TX, Diclon + TX, Dichlorofen + TX, Dichlorvos + TX, Diclozoline + TX, Dicliphos + TX, Diclosimet + TX, Diclomezin + TX, Dichloran + TX, Dicrezyl + TX, Dicyclanil + TX, Dicyclopentadiene + TX, Dieldrin + TX, Dienochlor + TX, Dietofencarb + TX, Diethyl 5-methylpyrazole-3-yl phosphate + TX, Diethyltoluamide + TX, Diphenacome + TX, Difenoconazole + TX, Difethiaron + TX, Diflovidazine + TX, Diglyphus isaeaisaea)+TX, dilor+TX, dimatif+TX, dimefluthrin+TX, dimefox+TX, dimethane+TX, dimethirimol+TX, dimethomorph+TX, dimethrin+TX, dimethylcalvert+TX, dimethyl phthalate+TX, dimethylvinphos+TX, dimethilan+TX, dimoxystrobin+TX, dinex+TX, dinex-dicrexin+TX, diniconazole+TX, dinocup-4+TX, dinocup-6+TX, dinocton+TX, dinopenton+TX, dinopprop+TX, dinosaum+TX, dinocton Cebu+TX, Dinosulfone+TX, Dinoterbone+TX, Diofenolan+TX, Dioxabenzophos+TX, Dioxathion+TX, Diphacinone+TX, Diphenylsulfone+TX, Dipimethitron+TX, Dipirithione+TX, Disparure+TX, Disulfiram+TX, Dithianone+TX, Diticlophos+TX, DNOC+TX, Dodeca-8-en-1-ylacetate+TX, Dodeca-9-en-1-ylacetate+TX, Dodeca-8+TX, Dodemorph+TX, Dodicine+TX, Dozin+TX, Dofenapine+TX, Dominicalle +TX, Doramectin+TX, DSP+TX, d-Tetramethrin+TX, Ecdysterone+TX, Edifenphos+TX, EI 1642+TX, EMPC+TX, Encarsia formosa+TX, Endotar+TX, Endothion+TX, Enestrobrin+TX, Enoxastrobin+TX, EPBP+TX, Epoxyconazole+TX, Eprinomectin+TX, Eretmocerus eremicus+TX, Ergocalciferol+TX, Etaphos+TX, Etaboxam+TX, Ethiofencarb+TX, Ethyrimol+TX, Ethoate-methyl+TX, Ethyl 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoropropane-1-enoxy]phenyl]methyl]pyrazole-3-carboxylate (may be prepared from the method described in International Publication No. 2020 / 056090) + TX, ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate (may be prepared from the method described in International Publication No. 2020 / 056090) + TX, ethyl 1-[[4-[[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate + TX, ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate (this compound can be prepared from the method described in International Publication No. 2018 / 158365) + TX, ethyl 4-methyloctanoate + TX, ethyl formate + TX, ethyl hexanediol + TX, ethylene dibromide + TX, ethylene dichloride + TX, ethylene oxide + TX, etridiazole + TX Etrimphos + TX, Eugenol + TX, EXD + TX, Famoxadone + TX, Farnesol + TX, Farnesol and Nerolidol + TX, Fenamidom + TX, Phenaminosulf + TX, Phenaminestrobin + TX, Phenalimol + TX, Phenazaflor + TX, Fenbuconazole + TX, Fenbutatine oxide + TX, Fenchlorphos + TX, Phenetacarb + TX, Fenflam + TX, Fenhexamide + TX,Fenitrothion + TX, phenothiocarb + TX, phenoxacrim + TX, phenoxanil + TX, fenpiclonil + TX, fenpicoxamide + TX, fenpyritrin + TX, fenpropidine + TX, fenpropimorph + TX, fenpyrad + TX, fenpyrazamine + TX, fenpyroximate + TX, fenson + TX, fensulfothione + TX, fenthion + TX, fenthion-ethyl + TX, fentin + TX, fentripanil + TX, ferubam + TX, ferimzon + TX, iron(III) phosphate + TX, furocumafen + TX, florylpicoxamide + TX, fluazinam + TX, flubeneteram + TX, flubendimine + TX, flucoflon + TX, flusic Roxulon + TX, Fludioxonil + TX, Fluenetil + TX, Fluphenoxadiazam + TX, Fluphenoxystrobin + TX, Fluindapir + TX, Flumethylsulfolimu + TX, Flumorph + TX, Fluopicolide + TX, Fluopimomid + TX, Fluopyram + TX, Fluolbenside + TX, Fluoroacetamide + TX, Fluoroimide + TX, Fluoxapiproline + TX, Fluoxastrobin + TX, Fluoxythioconazole + TX, Flupropazine + TX, Flupropazine hydrochloride + TX, Fluquinconazole + TX, Flusilazole + TX, Flusulfamide + TX, Fluthianil + TX, Flutolanil + TX, Flutriafor + TX, Fluxapiroxad + TX, FMC 1137+TX, Forpet+TX, Formaldehyde+TX, Formetanate+TX, Formetanate hydrochloride+TX, Formparanate+TX, Fosetil-aluminum+TX, Fosmethilan+TX, Fosspire+TX, Fosthitane+TX, Frontalin+TX, Fuberidazole+TX, Flalaxil+TX, Flamethopyr+TX, Flathiocarb+TX, Furethrin+TX, Furfural+TX, Gamma-HCH+TX, Gliodin+TX, Grandolure+TX, Grandolure I+TX, Grandolure II+TX, Grandolure III+TX, Grandolure IV+TX, Guazatine+TX, Guazatine acetate+TX, Halfenprox+TX, HCH+TX, Hemel+TX, Hempa+TX, HEOD+TX, Heptachlor+TX, Heterophos+TX,Heterorhabditis bacteriophora and H. megidis + TX, hexaconazole + TX, hexadecylcyclopropane carboxylate + TX, hexarua + TX, hexamide + TX, HHDN + TX, Hippodamia conbergensis (Condens) + 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, Iposenol + TX, IPSP + TX, Isamidophos + TX, Isazofos + TX, Isobenzane + TX, Isocarbophos + TX, Isodrine + TX X, 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, Cadeslin + TX, Kasugamycin + TX, Kasugamycin Hydrochloride Hydrate + TX, Kereban + TX, Kinetin + TX, Quinoprene + TX, Kresoxim-Methyl + TX, Lead Arsenate + TX, Leptomastix Dactylopia dactylopii)+TX, leptophos+TX, linden+TX, lineatin+TX, lilimphos+TX, liturua+TX, lupulua+TX, rubenmixianan+TX, lithidathione+TX, Macrolophus caliginosus+TX, magnesium phosphide+TX, malonoben+TX, Mamestra brassicae NPV+TX, mancozeb+TX, mancozeb+TX, mandestrobin+TX, mandipropamide+TX, maneb+TX, majidox+TX,m-Cumenylmethylcarbamate + TX, Mecarbam + TX, Mecarbhon + TX, Medrua + TX, Mefentrifluconazole + TX, Megatomoic acid + TX, Menazone + TX, Mepanipyrim + TX, Meperfluthrin + TX, Mephosphorane + TX, Mepronil + TX, Mercury(II) oxide + TX, Mercury chloride + TX, Mesulfen + TX, Mesulfenphos + TX, Metalaxyl + TX, Metam + TX, Metam-potassium + TX, Metam-sodium + TX, Metaphycus helvolus + TX, Metarhizium anisopliae var. acridum + TX, Metarhizium anisopliae var. anisopliae var. anisoopliae) + TX, methallyl picoxamide + TX, metconazole + TX, metepa + TX, methacryphos + TX, methanesulfonyl fluoride + TX, metasulfocarb + TX, methiotepa + TX, metoclotophos + TX, methoprene + TX, metoquin-butyl + TX, metotrin + TX, methoxychlor + TX, methyl(Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxypropa-2-enoate + TX, methyl(Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxypropa-2-enoate (these compounds can be prepared from the methods 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 may be prepared from the methods described in International Publication No. 2020 / 079111) + TX,Methyl(Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazole-2-yl]phenoxy]propane-2-enoate + TX, methyl aphorate + TX, methyl bromide + TX, methyl eugenol + TX, methyl isothiocyanate + TX, methyl N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazole-4-yl]-2-methyl-phenyl]methyl]carbamate (may be prepared from the method described in International Publication No. 2020 / 097012) + TX, methyl N-[[4-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazole-4-yl]-2-methyl-phenyl]methyl]carbamate (may be prepared from the method described in International Publication No. 2020 / 097012) + TX, methyl N-[[5-[4-(2,4-dimethylphenyl)triazole-2-yl]-2-methylphenyl]methyl]carbamate + TX, methylchloroform + TX, methylene chloride + TX, methylneodecanamide + TX, methylram + TX, methylcarb + TX, metminostrobin + TX, methoxadiazone + TX, metraphenone + TX, methyltetraprole + TX, MGK 264 + TX, milbemycin oxime + TX, mipahox + TX, myrex + TX, monoclotophos + TX, morphothion + TX, molzide + TX, moxidectin + TX, muscarle + TX, mycrobutanil + TX, microzoline + TX, Myrothecium bergaria verrucaria) composition + TX, N-((1R)-1-benzyl-3-chloro-1-methyl-buta-3-enyl)-8-fluoro-quinoline-3-carboxamide (these compounds may be prepared from the method described in International Publication No. 2017 / 153380) + TX, N-((1S)-1-benzyl-3-chloro-1-methyl-buta-3-enyl)-8-fluoro-quinoline-3-carboxamide (these compounds may be prepared from the method described in International Publication No. 2017 / 153380) + TX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine + TX, N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine + TX,N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide + TX, N,N-Dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]1,2,4-triazole-3-amine (These compounds are described in International Publication No. 2017 / 055473, International Publication No. 2017 / 055469, International Publication No. 2017 / 093348, (Can be prepared from the method described in International Publication No. 2017 / 118689) + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl] N-[(1S)-1-benzyl-1,3-dimethylbutyl]-8-fluoroquinoline-3-carboxamide+TX, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methylpropyl]-8-fluoroquinoline-3-carboxamide+TX, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide+TX, N-[(Z)-methoxyiminomethyl]-4-[5- (trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide + TX, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide + TX, N-[2-[2,4-dichlorophenoxy]phenyl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide + TX, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide + T X, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared from the method described in International Publication No. 2016 / 202742) + TX, N'-[4-(4,5-dichlorothiazol-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 from 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 is from IPCOM (Can be prepared from the method described in 000249876D) + 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-methylformamidine+TX, N-[N-methoxy-C-methylcarbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide (these compounds may be prepared from the method described in International Publication No. 2018 / 202428)+TX, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methylphenyl]-N-isopropyl-N-methylformamidine (these compounds may be prepared from the method described in International Publication No. 2018 / 228896)+TX, Narbam+TX, Naphthalophos+TX, Nared+TX, Naphthalene+TX, NC-170+TX, Neodiprion Certifel 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, Nifluridide + TX, Nikkomycin + TX, N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine + TX, Nichiazine + TX, Nitrapyrine + TX, Nitrilacarb + TX, Nitrilacarb 1:1 zinc chloride complex + TX, Nitrotar-isopropyl + TX, N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide + TX, N-methyl-4-[5 -(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide+TX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzenecarbothioamide+TX, norbolmid+TX, nualimol+TX, O,O,O',O'-tetrapropyldithiopyrophosphate+TX, octadeca-2,13-dien-1-yl acetate+TX, octadeca-3,13-dien-1-yl acetate+TX, octylinone+TX, oflace+TX, oleic acid+TX, omethoate+TX, orflurua+TX, Orius species spp.)+TX, Orictalua+TX, Orysastrobin+TX, Ostramon+TX, Oxadixyl+TX, Oxamate+TX, Oxathiapiproline+TX, Oxycopper+TX, Oxolinic acid+TX, Oxocarboxyne+TX, Oxideprophos+TX, Oxydisulfon+TX, Oxytetracycline+TX, Paclobutrazol+TX, Paecilomyces fumosoroseus+TX, Para-dichlorobenzene+TX, Parathion+TX, Parathion-methyl+TX, Pefurazoate+TX, Penconazole+TX, Pencyclon+TX, Penflufen+TX, Penflulon+TX, Pentachlorophenol+TX, Pentachlorophenyl laurate+TX, Penthiopyrad+TX, Permethrin+TX, PH 60-38+TX, phenamacryl+TX, fencapton+TX, fosacetim+TX, phosalon+TX, phosdiphen+TX, phospholan+TX, phosglycine+TX, fosniclor+TX, phosphamidone+TX,Phosphine + TX, Phosphate + TX, Phoxime-methyl + TX, Phthalide + TX, Phytoseiulus persimilis + TX, Picarbutrazox + TX, Picalidine + TX, Picoxystrobin + TX, Pindone + TX, Piperazine + TX, Piperonyl butoxide + TX, Piprotal + TX, Pyrimethaphos + TX, Polychlorodicyclopentadiene isomer + TX, Polychloroterpene + TX, Polynactin + TX, Polyoxin + TX, Potassium arsenite + TX, Potassium ethylxanthogenicate + TX, Hydroxyquinoline sulfate potassium + TX, Potassium thiocyanate + TX, pp'-DDT+TX, Precosen I+TX, Precosen II+TX, Precosen III+TX, Primidophos+TX, Probenazole+TX, Prochloraz+TX, Proclonol+TX, Procymidone+TX, Profluthrin+TX, Promacil+TX, Promecarb+TX, Propamocarb+TX, Propiconazole+TX, Propineb+TX, Propoxul+TX, Propropyl isomer+TX, Proquinazide+TX, Protidathion+TX, Prothioconazole+TX, Prothiofos + TX, Protoate + TX, Pidiflumetofen + TX, Pyraclostrobin + TX, Pyramethostrobin + TX, Pyraoxystrobin + TX, Pyrapropoin + TX, Pyraziflumid + TX, Pyrazofos + TX, Pyrethmetrin + TX, Pyrethrin I + TX, Pyrethrin II + TX, Pyrethrin + TX, Pyribencarb + TX, Pyridaclomethyl + TX, Pyridafenthion + TX, Pyridine-4-amine + TX, Pyriphenox + TX, Pyrimethanil + TX , Pyrimite+TX, Pyrimorph+TX, Pyrinulone+TX, Pyriophenone+TX, Pyrisoxazole+TX, Pyrroquilon+TX, Quasia+TX, Quinalphos+TX, Quinalphos-methyl+TX, Quinoclamine+TX, Quinofumeline+TX, Quinonamide+TX, Quinotion+TX, Quinoxyfen+TX, Quinthiophos+TX, Quintozen+TX, R-1492+TX, Lafoxanide+TX, Resmethrin+TX, Reynoutria sachalinensis extract+TX, Ribavirin+TX, R-metalaxyl+TX, Rotenone+TX, Lianya+TX, Lianodine+TX,S421+TX, Sabajira+TX, Shuladan+TX, Siriloside+TX, Seboctilamine+TX, Sebufos+TX, Sedaxane+TX, Selamectin+TX, Sesamex+TX, Sesasmolin+TX, SI-0009+TX, Siguru+TX, Simazine+TX, Simeconazole+TX, Sodium arsenite+TX, Sodium cyanide+TX, Sodium fluoride+TX, Sodium fluoroacetate+TX, Sodium hexafluorosilicate+TX, Sodium pentachlorophenoxide+TX, Sodium selenate+TX, Sodium tetrathiocarbonate+TX, Sodium thiocyanate+TX, Sofamide+TX, Solzidine+TX, Spiroxamine+TX, SSI-121+TX, Steinernema viviones bibionis)+TX, Steinernema carpocapsae+TX, Steinernema feltiae+TX, Steinernema glaseri+TX, Steinernema riobrave+TX, Steinernema riobravis+TX, Steinernema scapterisci+TX, Steinernema species spp.)+TX, streptomycin+TX, streptomycin sesquisulfate+TX, strychnine+TX, sulcatol+TX, sulcoflon+TX, sulcoflon-sodium+TX, sulfiram+TX, sulfuramide+TX, sulfotep+TX, sulfoxide+TX, sulfur+TX, sulfuryl fluoride+TX, sulprophos+TX, tar oil+TX, tau-fluvalinate+TX, tadimucarb+TX, TDE+TX, tebuconazole+TX, tebufloxin+TX, tebupyrimphos+TX, 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-yl acetate + TX, Tetradiphon + TX, Tetramethylfluthrin + TX, Tetrasul + TX, Thallium sulfate + TX, Thiabendazole + TX, Thiafenox + TX, Thiapronil + TX, Cyclophos + TX, Tifluzamide + TX, Thiocarboxyme + TX, Thiocic, Ram + 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, Torcrophos-methyl + TX, Tol Procarb + 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 species 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, Tranquol+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, Zetamethrin + TX, Zhongshengmycin + TX, Zinc naphthenate + TX, Zinc phosphide + TX, Thiazole zinc + TX, Zineb + TX, Ziram + TX, Zolaprofos + TX; Acinetobacter lwoffii + TX, Acremonium alternatum + TX, Acremonium cephalosporium + TX, Acremonium diospyri + TX, Acremonium obclavatum + TX, Adoxophyes orana granulosis virus (AdoxGV) (Capex®) + TX, Agrobacterium radiobacter strain K84 (Galltrol-A®) + TX, Alternaria alternate + TX, Alternaria cassia + TX, Alternaria destoluene (Alternaria destruens) (Smolder(registered trademark)) + TX, Ampelomyces quisqualis (AQ10(registered trademark)) + TX, Aspergillus flavus AF36 (AF36(registered trademark)) + TX, Aspergillus flavus NRRL 21882 (Aflaguard(registered trademark)) + TX, Aspergillus spp. + TX, Aureobasidium pullulans + TX, Azospirillum (MicroAZ(registered trademark), TAZO B(registered trademark)) + TX, Azotobacter + TX, Azotobacter crooccum (Azotobacter Bacillus chroocuccum (Azotomeal®) + TX, Azotobacter cysts (Bionatural Blooming Blossoms®) + TX, Bacillus amyloliquefaciens + TX, Bacillus cereuscereus)+TX, Bacillus chitinosporus strain AQ746+TX, Bacillus chitinosporus strain CM-1+TX, Bacillus circulans+TX, Bacillus firmus (BioSafe®, BioNem-WP®) especially strain CNMC1-1582 (e.g., VOTIVO® manufactured by BASF SE)+TX, Bacillus licheniformis strain 3086 (EcoGuard®, Green Releaf®)+TX, Bacillus licheniformis (Bacillus Bacillus licheniformis) strain HB-2 (Biostart (trademark), formerly Rhizoboost (registered trademark)) + TX, Bacillus macerans + TX, Bacillus marismortui + TX, Bacillus megaterium + TX, Bacillus mycoides strain AQ726 + TX, Bacillus papillae (Milky Spore Powder (registered trademark)) + TX, Bacillus pumilus species + TX, Bacillus pumilus strain AQ717 + TX, Bacillus pumilus strain GB34 (Yield Shield (registered trademark)) + TX, Bacillus pumilus 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 (BacillusBacillus subtilis strain AQ153+TX, Bacillus subtilis strain AQ743+TX, Bacillus subtilis strain QST 713 (CEASE®, Serenade®, Rhapsody®)+TX, Bacillus subtilis strain QST 714 (JAZZ®)+TX, Bacillus subtilis strain QST3002+TX, Bacillus subtilis strain QST3004+TX, Bacillus subtilis variety amyloricephasiensis (Bacillus subtilis var. 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 krustaki (Bacillus thuringiensis kurstaki)(Javelin(registered trademark), Deliver(registered trademark), CryMax(registered trademark), Bondide(registered trademark), Scutella WP(registered trademark), Turilav WP(registered trademark), Astuto(registered trademark), Dipel WP(registered trademark), Biobit(registered trademark), Foray(registered trademark))+TX, Bacillus thuringiensis kurstaki BMP 123(Baritone(registered trademark))+TX, Bacillus thuringiensis kurstakikurstaki)HD-1 (Bioprotec-CAF / 3P(registered trademark))+TX, Bacillus thuringiensis strain AQ52+TX, Bacillus thuringiensis strain BD#32+TX, Bacillus thuringiensis tenebrionis (Novodor(registered trademark), BtBooster)+TX, Bacillus thuringiensis var. aizawai (XenTari(registered trademark), DiPel(registered trademark))+TX, Bacteria spp. (GROWMEND(registered trademark), GROWSWEET(registered trademark), Shootup(registered trademark))+TX, Clavipacter misiganensis Bacteriophage of michiganensis (AgriPhage®, Bakflor®) + TX, Beauveria bassiana (Beaugenic®, Brocaril WP®) + TX, Beauveria bassiana GHA (Mycotrol ES®, Mycotrol O®, BotaniGuard®) + TX, Beauveria brongniartii (Engerlingspilz®, Schweizer Beauveria®, Melocont®) + TX, Beauveria spp. + TX, Botrytis cineria + TX, Bradyrhizobium japonica japonicum) (TerraMax®) + TX, Brevibacillus brevis + TX, Burkholderia cepacia (Deny®, Intercept®, BlueCircle (registered trademark) + TX, Burkholderia gladii + TX, Burkholderia gladioli + TX, Burkholderia spp. + TX, Canadian thistle fungus (CBH Canadian Bioherbicide (registered trademark)) + TX, Candida butyri + TX, Candida famata + TX, Candida fructus + TX, Candida glabrata + TX, Candida guilliermondii + TX, Candida melibiosica + TX, Candida oreophylla (Candida Candida oleophila strain O + TX, Candida parapsilosis + TX, Candida pelliculosa + TX, Candida pulcherrima + TX, Candida reukaufii + TX, Candida saitoana (Bio-Coat®, Biocure®) + TX, Candida sake + TX, Candida spp. + TX, Candida tenius + TX, Cedecea davisae + TX, Cellulomonas flavigena + TX, Chaetomium cochloides Cochliodes) (Nova-Cide®) + TX, Chaetomium globosum (Nova-Cide®) + TX, Chromobacterium subtsugaesubtsugae) strain PRAA4-1T (Grandevo(registered trademark)) + TX, Cladosporium chlorocephalum + TX, Cladosporium cladosporioides + TX, Cladosporium oxysporum + TX, Cladosporium spp. + TX, Cladosporium tenuissimum nuissimum)+TX, Clonostachys rosea (EndoFine®)+TX, Colletotrichum acutatum+TX, Coniothyrium minitans (Cotans WG®)+TX, Coniothyrium spp.)+TX, Cryptococcus albidus (YIELDPLUS(registered trademark))+TX, Cryptococcus humicola+TX, Cryptococcus infirmo-miniatus+TX, Cryptococcus laurentii+TX, Cryptophlebia leucotreta granulosis virus (Cryptex(registered trademark))+TX, Cupriavidus campinensis+TX, Cydia pomonella granulosis virus (CYD-X(registered trademark), Madex(registered trademark), Madex(registered trademark)Plus, Madex Max, Carpovirusine (registered trademark) + TX, Cylindrobasidium laeve (Stumpout (registered trademark)) + TX, Cylindrocladium + TX, Debaryomyces hansenii + TX, Drecslera hawaiinensis + TX, Enterobacter cloacae + TX, Enterobacteriaceae + TX, Entomophtora virulenta (Vektor (registered trademark)) + 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, Granulopathy virus (Granupom®)+TX, Halobacillus halophilus+TX, Halobacillus litoralis+TX, Halobacillus trueperi+TX, Halomonas spp.)+TX, Halomonas subglaciescola+TX, Halovibrio variabilis+TX, Hanseniaspora uvarum+TX, Helicoverpa armigera nuclear polyhedron virus (Helicovex®)+TX, Helicoverpa zea nuclear polyhedron virus (Gemstar®)+TX, Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus strain, PFR-97®, PreFeRal®)+TX, isoflavone Formononetin (Myconate®) + TX, Kloeckera apiculata + TX, Kloeckera spp.)+TX, Lagenidium giganteum (Laginex®)+TX, Lecanicillium lecanii (formerly known as Verticillium lecanii) (Mycotal®) conidia of strain KV01 (e.g., Vertalec® by Koppert / Arysta)+TX, Lecanicillium longisporum (Vertiblast®)+TX, Lecanicillium muscarium (Vertikil®)+TX, Lymantria Dispar nuclear polyhedron disease virus (Disparvirus®)+TX, Marinococcus halophilus halophilus)+TX, Meira geulakonigii+TX, Metarhizium anisopliae (Destruxin WP(registered trademark))+TX, Metarhizium anisopliae (Met52(registered trademark))+TX, Metschnikowia fruticola (Shemer(registered trademark))+TX, Metschnikowia pulcherrima+TX, Microdochium dimerum (Antibot(registered trademark))+TX, Micromonospora coerulea+TX, Microsphaeropsis ochracea+TX, Muscodor albus albus)620(Muscudor(registered trademark))+TX, Muscodor roseus, especially strain A3-5 (accession number NRRL 30548)+TX, Mycorrhizae spp.)(AMykor(registered trademark), Root Maximizer(registered trademark))+TX, Myrothecium verrucaria strain AARC-0255 (DiTera(registered trademark), BROS PLUS(registered trademark))+TX, Ophiostoma piliferum strain D97 (Sylvanex(registered trademark))+TX, Paecilomyces farinosus+TX, Paecilomyces lilacinus strain 251 (MeloCon WG(registered trademark))+TX, Paecilomyces linacinus (Biostat WP(registered trademark))+TX, Paenibacillus polymixa polymyxa)+TX, Pantoea agglomerans (BlightBan C9-1(registered trademark))+TX, Pantoea spp. +TX, Pasteuria nishizawae, especially strain Pn1 (CLARIVA of Syngenta / ChemChina);+TX, Pasteuria spp. (Econem(registered trademark))+TX, Penicillium aurantiogriseum +TX, Penicillium billai (Jumpstart(registered trademark), TagTeam(registered trademark))+TX, Penicillium brevicompactum +TX, Penicillium phlequentans (Penicillium Penicillium frequentans) + TX, Penicillium griseofulvum + TX, Penicillium purpurogenum + TX, Penicillium spp.)+TX, Penicillium viridicatum+TX, Phlebiopsis gigantean (Rotstop®)+TX, Phosphating bacteria (Phosphomeal®)+TX, Phytophthora cryptogea+TX, Phytophthora palmivora (Devine®)+TX, Pichia anomala+TX, Pichia guilliermondii+TX, Pichia membranaefaciens+TX, Pichia onychis+TX, Pichia stipites (Pichia Pseudomonas stipites) + TX, Pseudomonas aeruginosa + TX, Pseudomonas aureofasciens (Spot-Less Biofungicide®) + TX, Pseudomonas cepacia + TX, Pseudomonas chlororaphis (AtEze®) + TX, Pseudomonas corrugate + TX, Pseudomonas fluorescens (Zequanox®) + TX, Pseudomonas fluorescens strain A506 (BlightBan A506®) + TX, Pseudomonas petida (Pseudomonas putida)+TX, Pseudomonas reactans+TX, Pseudomonas spp.)+TX, Pseudomonas syringae (Bio-Save®)+TX, Pseudomonas viridiflava+TX, Pseudozyma flocculosa strain PF-A22 UL (Sporodex L®)+TX, Puccinia canaliculata+T. X, Puccinia thlaspeos (Wood Warrior®) + TX, Pythium paroecandrum + TX, Pythium oligandrum (Polygandron®, Polyversum®) + TX, Pythium periplocum + TX, Rhanella aquatilis + TX, Rhanella spp. + TX, Rhizobia (Dormal®, Vault®) + TX, Rhizoctonia + TX, Rhodococcus globerulus strain AQ719 + TX, Rhodosporidium diovovatum diobovatum)+TX, Rhodosporidium toruloides+TX, Rhodotorula glutinis+TX, Rhodotorula graminis+TX, Rhodotorula mucilagnosa+TX, Rhodotorula rubra+TX, Rhodotorula spp.+TX, Saccharomyces cerevisiae+TX, Salinococcus roseus+TX, Sclerotinia minor (SARRITOR(registered trademark))+TX, Sclerotinia minor (Sclerotinia minor)+TX, Scytalidium spp.+TX, Scytalidium uredinicola+TX, Serratia marcescens+TX, Serratia plymuthica+TX, Serratia spp.)+TX, Sordaria fimicola+TX, Spodoptera exigua nuclear polyhedron virus (Spod-X®, Spexit®)+TX, Spodoptera littoralis nuclear polyhedron virus (Littovir®)+TX, Sporobolomyces roseus+TX, Stenotrophomonas maltophilia+TX, Streptomyces albaduncus+TX, Streptomyces exfoliates+TX, Streptomyces galbus+TX, Streptomyces glyceoplanus (Streptomyces griseoplanus)+TX, Streptomyces griseoviridis (Mycostop®)+TX, Streptomyces hygroscopicus+TX, Streptomyces lydicus (Actinovate®)+TX, Streptomyces lydicus WYEC-108 (ActinoGrow®)+TX, Streptomyces violaceus+TX, Tilletiopsis minor+TX, Tilletiopsis spp.)+TX, Trichoderma asperellum (T34 Biocontrol®)+TX, Trichoderma atroviride (Plantmate®)+TX, Trichoderma gamsii (Tenet®)+TX, Trichoderma hamatum TH 382+TX, Trichoderma harzianum rifai (Mycostar®)+TX, Trichoderma harzianum T-22 (Trianum-P®, PlantShield HC®, RootShield®, Trianum-G®)+TX, Trichoderma harzianum (Trichoderma harzianum)T-39(Trichodex(registered trademark))+TX, Trichoderma inhamatum+TX, Trichoderma koningii+TX, Trichoderma lignorum+TX, Trichoderma longibrachiatum+TX, Trichoderma polysporum(Binab T(registered trademark))+TX, Trichoderma spp.)LC 52 (Sentinel (registered trademark)) + TX, Trichoderma taxi + TX, Trichoderma virens (formerly Gliocladium virens GL-21) (SoilGuard (registered trademark)) + TX, Trichoderma virens + TX, Trichoderma viride + TX, Trichoderma viride strain ICC 080 (Remedier (registered trademark)) + TX, Trichosporon pullulans + TX, Trichosporon spp. + TX, Trichothecium roseum + TX, Trichothecium 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 supplemental micronutrients (Natural II®)+TX, various fungi (Millennium Microbes®)+TX, Verticillium chlamydosporium+TX, Vip3Aa20 (VIPtera®)+TX, Virgibaclillus marismortzii marismortui)+TX, Xanthomonas campestris pv. Poae (Camperico®)+TX, Xenorhabdus bovienii+TX, Xenorhabdus nematophilus+TX;.AGNIQUE® MMF + TX, Azadirachtin (PLasma Neem Oil®, AzaGuard®, MeemAzal®, Molt-X®, e.g., Certis, US AZATIN XL) + TX, Vegetable IGR (Neemazad®, Neemix®) + TX, BugOil® + TX, Canola Oil (Lilly Miller Vegol®) + TX, American Arisaema (Chenopodium ambrosioides near ambrosioides) (Requiem®) + TX, Chrysanthemum Extract (Crisant®) + TX, Lamiaceae Essential Oil (Botania®) + TX, Neem Oil Extract (Trilogy®) + TX, Clove, Rosemary, Peppermint and Thyme Oil Extract (Garden Insect) Killer® + TX, Garlic + TX, Glycine Betaine (Greenstim®) + TX, Kaolin (Screen®) + TX, Lemongrass Oil (GreenMatch®) + TX, Melaleuca alternifolia Extract (also known as Tea Tree Oil) (Timorex Gold®) + TX, Clove Peppermint Garlic Oil and Mint Mixture (Soil Shot®) + TX, Clove Rosemary and Peppermint Extract Mixture (EF 400®) + TX, Rosemary Sesame Peppermint Thyme and Cinnamon Extract Mixture (EF 300®) + TX, Neem Oil + TX, Nepeta cataria Catnip Oil + TX, Nepeta catalina catarina) + TX, nicotine + TX, oregano oil (MossBuster®) + TX, sesame oil (Nematon®) + TX, pine oil (Retenol®) + TX, pyrethrum + TX, Quillaja saponaria (QuillajaSaponaria (NemaQ®) + TX, Reynoutria sachalinensis (Regalia®, Sakalia®) + TX, Rotenone (Eco Roten®) + TX, Rutaceae plant extract (Soleo®) + TX, Soybean oil (Ortho ecosense®) + TX, Storage glucam from brown algae (Laminarin®) + TX, Thyme oil + TX; (E,Z)-7,9-Dodecadiene-1-yl acetate + TX, (E,Z,Z)-3,8,11-Tetradecatrienylate + TX, (Z,Z,E)-7,11,13-Hexadecatrienal + TX, 2-Methyl-1-butanol + TX, Biolure® + TX, Blackheaded Fireworm Pheromone (3M Sprayable Blackheaded Fireworm Pheromone®) + TX, Calcium Acetate + TX, Check-Mate® + TX, Codling Moth Pheromone (Paramount dispenser-(CM) / Isomate C-Plus®) + TX, Entostat Powder (Exosex CM®) (Exosex extract from palm trees) + TX, Grape Berry Moth Pheromone (3M MEC-GBM Sprayable Pheromone(registered trademark) + TX, Lavanzuryl senecioate + TX, Leafroller pheromone (3M MEC-LR Sprayable Pheromone(registered trademark)) + TX, Muscamone (Snip7 Fly Bait(registered trademark)) + TX, Oriental Fruit Moth pheromone (3M oriental fruit moth sprayable pheromone(registered trademark)) + TX, Peachtree Borer pheromone (Isomate-P(registered trademark)) + TX, Scenturion(registered trademark) + TX, Starbar Premium Fly Bait(registered trademark)) + TX, Tomato pinworm pheromone (3M Sprayable pheromone(registered trademark)) + TX; Acerophagus papaya + TX, Adalia bipunctata (Adalia-System®) + TX, Adalia bipunctata (Adaline®) + TX, Adalia bipunctata (Aphidalia®) + TX, Ageniaspis citricola + TX, Ageniaspis fuscicollis + TX, Amblyseius andersoni (Anderline®, Andersoni-System®) + TX, Amblyseius californicus californicus) (Amblyline(registered trademark), Spical(registered trademark)) + TX, Amblyseius cucumeris (Thripex(registered trademark), Bugline cucumeris(registered trademark)) + TX, Amblyseius fallacis (Fallacis(registered trademark)) + TX, Amblyseius swirskii (Bugline swirskii(registered trademark), Swirskii-Mite(registered trademark)) + TX, Amblyseius womersleyi (WomerMite(registered trademark)) + TX, Amitus hesperidum + TX, Anagrus atomus + TX, Anagyrus fussiventris fusciventris)+TX, Anagyrus kamali+TX, Anagyrus loecki+TX, Anagyrus pseudococci (Citripar(registered trademark))+TX, Anicetus benefices+TX, Anisopteromaluscalandrae)+TX, Anthocoris nemoralis (Anthocoris-System(registered trademark))+TX, Aphelinus abdominalis (Apheline(registered trademark), Aphiline(registered trademark)),+TX, Aphelinus asychis+TX, Aphidius colemani (Aphipar(registered trademark))+TX, Aphidius ervi (Aphelinus-System(registered trademark))+TX, Aphidius ervi (Ervipar(registered trademark))+TX, Aphidius gifuensis+TX, Aphidius matricariae (Aphidius matricariae)(Aphipar-M(registered trademark))+TX, Aphidoletes Aphidimyza(Aphidend(registered trademark), Aphidoline(registered trademark))+TX, Aphytis lingnanensis+TX, Aphytis melinus+TX, Aprostocetus hagenowii+TX, Atheta coriaria(Staphyline(registered trademark))+TX, Bombus spp.+TX, Bombus terrestris(Beeline(registered trademark), Tripol(registered trademark))+TX, Bombus terrestris(Natupol Beehive (registered trademark) + TX, Cephalonomia stephanoderis + TX, Chilocorus nigritus + TX, Chrysoperla carnea (Chrysoline (registered trademark), Chrysopa (registered trademark)) + TX, Chrysoperla rufirabris (Chrysoperlarufilabris)+TX, Cirrospilus ingenuus+TX, Cirrospilus quadristriatus+TX, Citrostichus phyllocnistoides+TX, Closterocerus chamaeleon+TX, Closterocerus spp.+TX, Coccidoxenoides perminutus (Planopar®)+TX, Coccophagus cowperi+TX, Coccophagus lycimnia+TX, Cotesia flavipes)+TX, Cotesia plutellae+TX, Cryptolaemus montrouzieri (Cryptobug®, Cryptoline®)+TX, Cybocephalus nipponicus+TX, Dacnusa sibirica (Minusa®, DacDigline®, Minex®)+TX, Delphastus catalinae (Delphastus®)+TX, Delphastus pusillus+TX, Diachasmimorpha krausii+TX, Diachasmimorpha longicaudata longicaudata)+TX, Diaparsis jucunda+TX, Diaphorencyrtus aligarhensis+TX, Diglyphus isaeaeisaea) (Diminex(registered trademark), Miglyphus(registered trademark), Digline(registered trademark)) + TX, Diversinervus spp. + TX, Encarsia citrina + TX, Encarsia formosa (Encarsia max(registered trademark), Encarline(registered trademark), En-Strip(registered trademark)) + TX, Encarsia guadeloupae + TX, Encarsia haitiensis + TX, Episyrphus balteatus (Syrphidend(registered trademark)) + TX, Eretmoceris siphonini + TX, Eretmocerus californicus californicus)+TX, Eretmocerus eremicus (Enermix(registered trademark), Ercal(registered trademark), Eretline e(registered trademark), Bemimix(registered trademark))+TX, Eretmocerus hayati+TX, Eretmocerus mundus (Bemipar(registered trademark), Eretline m(registered trademark))+TX, Eretmocerus siphonini+TX, Exochomus quadripustulatus+TX, Feltiella acarisuga (Feltiline(registered trademark))+TX, Feltiella acarisuga (Spidend(registered trademark))+TX, Phopius alisanus (Fopius arisanus)+TX, Fopius ceratitivorus+TX, formononetin (Wirless Beehome®)+TX, Franklinothripsvespiformis)(Vespop(registered trademark))+TX, Galendromus occidentalis+TX, Goniozus legneri+TX, Habrobracon hebetor+TX, Harmonia axyridis(HarmoBeetle(registered trademark))+TX, Heterorhabditis bacteriophora(NemaShield HB(registered trademark), Nemaseek(registered trademark), Terranem-Nam(registered trademark), Terranem(registered trademark), Larvanem(registered trademark), B-Green(registered trademark), NemAttack(registered trademark), Nematop(registered trademark))+TX, Heterorhabditis megidis(Nemasys H(registered trademark), BioNem H(registered trademark), Exhibitline hm(registered trademark), Larvanem-M(registered trademark))+TX, Heterorhabditis spp. (Lawn Patrol(registered trademark))+TX, Hippodamia convergens+TX, Hypoaspis aculeifer (Aculeifer-System(registered trademark), Entomite-A(registered trademark))+TX, Hypoaspis miles (Hypoline m(registered trademark), Entomite-M(registered trademark))+TX, Lbalia leucospoides+TX, Lecanoideus floccissimus+TX, Lemophagus erabundus Leptomastidea abnormis + TX, Leptomastix dactylopii (Leptopar®) + TX, Leptomastix eponaepona)+TX, Lindorus lophanthae+TX, Lipolexis oregmae+TX, Lucilia caesar (Natufly(registered trademark))+TX, Lysiphlebus testaceipes+TX, Macrolophus caliginosus (Mirical-N(registered trademark), Macroline c(registered trademark), Mirical(registered trademark))+TX, Mesoseirus Mesoseiulus longipes + TX, Metaphycus flavus + TX, Metaphycus lounsburyi + TX, Micromus angulatus (Milacewing®) + TX, Microterys flavus + TX, Muscidifurax raptorellus and Spalangia cameroni (Biopar®) + TX, Neodryinus typhlocybae + TX, Neoseiulus californicus + TX, Neoseiulus cucumeris cucumeris)(THRYPEX(registered trademark))+TX, Neoseiulus fallacis+TX, Nesideocoris tenuis(NesidioBug(registered trademark), Nesibug(registered trademark))+TX, Ophyra aenescens(Biofly(registered trademark))+TX, Orius insidiosus(Thripor-I(registered trademark), Oriline i(registered trademark))+TX, Orius laevigatus(Thripor-L(registered trademark), Oriline l(registered trademark))+TX, Orius majusculus(Oriline m(registered trademark))+TX, Orius strigicollis)(Thripor-S(registered trademark))+TX, Pauesia juniperorum+TX, Pediobius foveolatus+TX, Phasmarhabditis hermaphrodita(Nemaslug(registered trademark))+TX, Phymastichuscoffea)+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 (Registered Trademark), NemAttack (Registered Trademark), Nemastar (Registered Trademark), Capsanem (Registered Trademark)) + TX, Steinernema feltiae (NemaShield (Registered Trademark), Nemasys F (Registered Trademark), BioNem F (Registered Trademark), Steinernema-System (Registered Trademark), NemAttack (Registered Trademark), Nemaplus (Registered Trademark), Exhibitlinesf(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.+TX, Steinernematid spp. (Guardian Nematodes(registered trademark))+TX, Stethorus punctilum 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(Trichogramma Platneri) + TX, Trichogramma pretiosum + TX, Xanthopimpla stemmator + TX; Abscisic acid + TX, Aminomite® + TX, BioGain® + TX, bioSea® + TX, CAS number: 2643947-26-4 + TX, Chondrostereum purpureum (Chontrol Paste®) + TX, Colletotrichum gloeosporioides (Collego®) + TX, Copper octanoate (Cueva®) + TX, Delta Trap (Trapline d®) + TX, Erwinia amylovora (Harpin) (ProAct®) + TX, Ni-HIBIT Gold CST(registered trademark))+TX, fatty acids derived from natural by-products of extra virgin olive oil (FLIPPER(registered trademark))+TX, ferric phosphate (Ferramol(registered trademark))+TX, funnel trap (Trapline y(registered trademark))+TX, Gallex(registered trademark)+TX, Grower's Secret(registered trademark)+TX, homo-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)+TX, Rebell Amarillo(registered trademark))+TX, SuffOil-X(registered trademark)+TX, trap (Takitrapline y+b(registered trademark))+TX; Bacillus mojavensis strain R3B (accession number NCAIM(P)B001389) (International Publication No. 2013 / 034938) + TX, Bacillus pumilus, in particular strain BU F-33 with NRRL accession number 50185 (BASF's CARTISSA®, EPA registration number 71840-19) + TX, Bacillus subtilis CX-9060, Bacillus sp., in particular strain D747 with accession number FERM BP-8234 (available from Kumiai Chemical Industry Co., Ltd. as DOUBLE NICKEL®), 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 accession number DSM 10271, Bacillus subtilis, in particular strain QST713 / AQ713 (NRRL, with accession number B-21661, described in U.S. Patent No. 6,060,051, and Bayer CropScience) LP (available from the US as SERENADE® OPTI or SERENADE® ASO) + TX, Paenibacillus polymyxa, especially strain AC-1 (e.g., Green Biotech Company Ltd.)Paenibacillus strains with accession number NRRL B-50972 or accession number NRRL B-67129, International Publication No. 2016 / 154297 + TX; Pantoea agglomerans, particularly strain E325 (accession number NRRL B-21856) (available from Northwest Agri Products as BLOOMTIME BIOLOGICAL® FD BIOPESTICIDE) + TX; Pseudomonas proradix (e.g., PRORADIX® of 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., AgBioChem, CA, GALLTROL-A®) + TX, Bacillus amyloliquefaciens isolate B246 (e.g., University of Pretoria, AVOGREEN®) + TX, Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL accession number B-50768, International Publication No. 2014 / 028521) (STARGUS®, Marrone Bio Innovations) + TX, Bacillus amyloliquefaciens strain FZB42, accession number DSM 23117 (ABiTEP, available as RHIZOVITAL® from DE) + TX, Bacillus amyloliquefaciens, in particular strain D747 (available as Double Nickel® from Kumiai Chemical Industry Co., Ltd., with accession number FERM BP-8234, U.S. Patent No. 7,094,592) + TX, Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (QUARTZO® (WG) and PRESENCE® (WP)) of FMC Corporation + TX, Bacillus licheniformis, in particular accession number ATCC Strain SB3086 containing 55406, International Publication No. 2003 / 000051 (available from Novozymes as ECOGUARD® Biofungicide and GREEN RELEAF®) + TX, Bacillus methylotrophicus strain BAC-9912 (Chinese Academy of Sciences' Institute of Applied Sciences)(from Ecology) +TX, Bacillus mycoides, isolate with accession number B-30890 (available from Certis USA LLC as BMJ TGAI® or WG and LifeGard®) +TX, Bacillus pumilus, in particular strain GB34 (available from Bayer AG, DE as Yield Shield®) +TX, Bacillus pumilus, in particular strain QST2808 (available from Bayer CropScience LP, US as SONATA®, with accession number NRRL B-30087, as described in U.S. Patent No. 6,245,551) +TX, Bacillus subtilis CX-9060 +TX, Bacillus subtilis (Bacillus Bacillus subtilis) IAB / BS03 (AVIV (trademark) of STK Bio-Ag Technologies, PORTENTO (registered trademark) of Idai Nature) + TX, Bacillus subtilis strain KTSB (FOLIACTIVE (registered trademark) of Donaghys) + TX, Bacillus subtilis strain BU1814 (available as VELONDIS (registered trademark) PLUS, VELONDIS (registered trademark) FLEX and VELONDIS (registered trademark) EXTRA of BASF SE) + TX, Bacillus subtilis strain GB03 (available as Kodiak (registered trademark) from Bayer AG, DE) + TX, Bacillus subtilis strain MBI 600 (available as SUBTILEX from BASF SE), accession number NRRL U.S. Patent No. 5,061,495+TX, Bacillus subtilis strain Y1336 (Bion-Tech, Taiwan, BIOBAC® WP)Available as, registered in Taiwan as a biological fungicide with registration numbers 4764, 5454, 5096 and 5277) + TX, Bacillus subtilis var. amyloliquefaciens strain FZB24 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5)) + TX, Bacillus subtilis Y1336 (available from Bion-Tech, Taiwan as BIOBAC® WP, registered in Taiwan as a biological fungicide with registration numbers 4764, 5454, 5096 and 5277) + TX, Paenibacillus epiphyticus of BASF SE Paenibacillus polymyxa ssp. plantarum (International Publication No. 2016 / 020371)+TX, Paenibacillus sp. strain with accession number NRRL B-50972 or accession number NRRL B-67129, International Publication No. 2016 / 154297+TX, Pseudomonas chlororaphis strain AFS009 with accession number NRRL B-50897, International Publication No. 2017 / 019448 (e.g., AgBiome) Innovations, HOWLER (trademark) and ZIO (registered trademark) of the US) + TX, Pseudomonas chlororaphis, particularly strain MA342 (e.g., CEDOMON (registered trademark), CERALL (registered trademark), and CEDRESS (registered trademark) by Bioagri and Koppert) + TX, Pseudomonas fluorescens strain A506 (e.g., by NuFarm)BLIGHTBAN® A506) + TX, Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena) + TX, Streptomyces griseoviridis strain K61 (also known as Streptomyces galbus strain K61) (accession number DSM 7206) (see MYCOSTOP® from Verdera, PREFENCE® from BioWorks, Crop Protection 2006, 25, 468-475) + TX, Streptomyces lydicus strain WYEC108 (Streptomyces lydicus (Streptomyces (Also known as *Lydicus* strain WYCD108US) (Actino-Iron® and Actinovate® of Novozymes) + TX; Trichoderma atroviride strain T11 (IMI352941 / CECT20498) + TX, Ampelomyces quisqualis strain AQ10 (e.g., AQ 10® by IntrachemBio Italia) + TX with accession number CNCM 1-807, Ampelomyces quisqualis, in particular strain AQ 10 (e.g., AQ 10® by IntrachemBio Italia) + TX, Aspergillus flavus strain NRRL 21882 (known as AFLA-GUARD® by Syngenta / ChemChina) + TX, Aureobasidium pullulans, in particular strain DSM Bud spores of 14941 + TX, Aureobasidium pullulans, especially bud spores of strain DSM14940 + TX, Aureobasidium pullulans, especially a mixture of bud spores of strains DSM14940 and DSM 14941 (e.g., Bio-ferm, CH's Botector®) + TX, Chaetomium cupreum (accession number CABI 353812) (e.g., AgriLife's BIOKUPRUM®) + TX, Chaetomium globosum (available as RIVADIOM® by Rivale) + TX, Cladosporium cladosporioides, accession number Coniothyrium minitans, specifically strain H39 with CBS122244, U.S. Patent Application Publication No. 2010 / 0291039 (by Stichting Dienst Landbouwkundig Onderzoek) + TX, Coniothyrium minitans, particularly strain CON / M / 91-8 (accession number DSM9660, e.g., Bayer CropScience Biologics).Contans(registered trademark) of GmbH +TX, Cryptococcus flavescens, strain 3C (NRRL Y-50378), +TX, Dactylaria Candida, Dilophosphora alopecuri (available as TWIST FUNGUS(registered trademark)), Fusarium oxysporum, strain Fo47 (available as FUSACLEAN(registered trademark) by Natural Plant Protection) +TX, Gliocladium catenulatum (synonym: Clonostachys rosea f. catenulate strain J1446 (e.g., Prestop(registered trademark) by Lallemand)) +TX, Gliocladium roseum Clonostachys rosea strain IK726 (also known as Clonostachys rosea f rosea) (Jensen DF, et al. Development of a biocontrol agent for plant disease control with special emphasis on the near commercial fungal antagonist Clonostachys rosea strain 'IK726', Australasian Plant Pathol. 2007, 36(2):95-101) + TX, Gliocladium roseum (also known as Clonostachys rosea f rosea), especially strain 321U from Adjuvants Plus, Xue AG (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root tot complex of field pea + TX, Can Jour PlantThis includes strains such as ACM941+TX, Metschnikowia fructicola, particularly strain NRRL Y-30752+TX, Microsphaeropsis ochracea, Penicillium steckii (DSM 27859, International Publication No. 2015 / 067800)+TX from BASF SE, and Trichoderma asperellum strain ICC 012 (also known as Trichoderma harzianum, ICC012) with accession number CABI CC IMI 392716 and accession number IMI Mixture of Trichoderma gamsii (formerly T. viride) strain ICC 080 (e.g., BIO-TAM® of Isagro USA, Inc. or BIODERMA® of Agrobiosol de Mexico, SA de CV) containing 392151 + TX, Penicillium vermiculatum + TX, Phlebiopsis gigantea strain VRA 1992 (ROTSTOP® C of Danstar Ferment) + TX, Pseudozyma flocculosa strain PF-A22 UL (available as SPORODEX® L of Plant Products Co., CA) + TX, Saccharomyces cerevisiae Saccharomyces cerevisiae) strain LAS117 cell wall (CEREVISANE® of Lesaffre, ROMEO® of BASF SE) + TX, Lesaffre et Compagnie, FR Saccharomyces cerevisiae strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938, CNCMNo. 1-3939 (International Publication No. 2010 / 086790) + TX, Saccharomyces cerevisiae, in particular strain LASO2 (from Agro-Levures et Derives) + TX, Simplicillium lanosoniveum + TX, strain T34 (e.g., T34 Biocontrol by Biocontrol Technologies SL, ES) or strain ICC 012 of Isagro + TX, strain WRL-076 (NRRL Y-30842), U.S. Patent No. 7,579,183 + TX, Talaromyces flavus strain V117b + TX, Trichoderma asperelloides JM41R (Accession No. NRRL B-50759) (BASF SE's TRICHO PLUS (registered trademark)) + TX, Trichoderma asperellum, in particular strain SKT-1 with accession number FERM P-16510 (e.g., ECO-HOPE (registered trademark) of Kumiai Chemical Industry Co., Ltd.) + TX, Trichoderma asperellum, in particular strain kd (e.g., T-Gro of Andermatt Biocontrol) + TX, Trichoderma atroviride strain 77B (T77 of Andermatt Biocontrol) + TX, Trichoderma atroviride strain ATCC 20476 (IMI 206040) + TX, Trichoderma atroviride strain LC52 (e.g., Agrimm Technologies) Tenet (Tenet) + TX, Trichoderma atroviride strain LU132 (e.g., Sentinel (Sentinel) + TX, Trichoderma atroviride strain NMI (Trichoderma atroviride) from Agrimm Technologies Limited)no.V08 / 002388+TX, Trichoderma atroviride strain NMI no.V08 / 002389+TX, Trichoderma atroviride strain NMI no.V08 / 002390+TX, Trichoderma atroviride strain no.V08 / 002387+TX, Trichoderma atroviride strain SKT-1 (FERM P-16510), Japanese Patent Publication (Published) No. 11-253151 +TX, Trichoderma atroviride strain SKT-2 (FERM P-16511), Japanese Patent Publication No. 11-253151 + TX, Trichoderma atroviride strain SKT-3 (FERM P-17021), Japanese Patent Publication No. 11-253151 + TX, Trichoderma atroviride, in particular strain SC1 (accession number CBS 122089, International Publication No. 2009 / 116106 and U.S. Patent No. 8,431,120 (from Bi-PA)) + TX, Trichoderma atroviride, strain CNCM 1-1237 (e.g., Agrauxine, Esquive® WP of FR) + TX, Trichoderma fertil fertile) (e.g., BASF product TrichoPlus) +TX, Trichoderma gamsii (formerly T. viride) +TX, Trichoderma gamsii (formerly T. viride) strain ICC 080 (IMI CC 392151 CABI) (available as BIODERMA® by AGROBIOSOL DE MEXICO, SADE CV), +TX, Trichoderma gamsii strain ICC080 (IMI CC 392151 CABI, e.g., AGROBIOSOL DEMEXICO, SADE CV's BioDerma + TX, Trichoderma harmatum + TX, accessories Trichoderma harmatum +TX, Trichoderma harzianum +TX, Trichoderma harzianum rifai T39 (e.g., Makhteshim, US Trichodex®) +TX, Trichoderma harzianum strain Cepa Simb T5 (from Simbiose Agro) +TX, Trichoderma harzianum strain DB 103 (available as T-GRO® 7456 by Dagutat Biolab) +TX, Trichoderma harzianum strain ITEM 908 (e.g., Trianum-P by Koppert) + TX, Trichoderma harzianum strain T-22 (e.g., Andermatt Biocontrol or Trianum-P by Koppert) + TX, Trichoderma harzianum strain TH35 (e.g., Root-Pro by Mycontrol) + TX, Trichoderma polysporum strain IMI 206039 (e.g., Binab TF WP by BINAB Bio-Innovation AB, Sweden) + TX, Trichoderma stromaticum with accession number Ts3550 (e.g., Tricovab by CEPLAC, Brazil) + TX, Trichoderma virens (Gliocladium virens) (Also known as virens) In particular strain GL-21 (e.g., Certis,Ulocladium audemancyi with accession number NM 99 / 06216, Trichoderma virens strain G-41 (accession number ATCC 20906) (formerly known as Gliocladium virens) (e.g., BioWorks, ROOTSHIELD® PLUS WP and TURFSHIELD® PLUS WP of the US) + TX, Trichoderma viride strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161:125-137) + TX, Trichoderma viride strain TV1 (e.g., Trianum-P by Koppert) + TX, Ulocladium audemancyi with accession number NM 99 / 06216 Verticillium albo-atrum (formerly V. dahliae) strain WCS850 (for example, DUTCH TRIG® by Tree Care Innovations) +TX, which has accession number WCS850 and is deposited with the Central Bureau for Fungi Cultures; Verticillium chlamydosporium +TX; A mixture of Azotobacter vinelandii and Clostridium Pasteurianum (available from Agrinos as INVIGORATE®) + TX, a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available from FMC Corporation as QUARTZO® (WG) and PRESENCE® (WP)) + TX, Azorhizobium caulinodans, especially strain ZB-SK-5 + TX, Azospirillum brasilense (e.g., VIGOR® from KALO, Inc.) + TX, Azospirillum lipoferum lipoferum) (For example, TerraMax, Inc.)VERTEX-IF(trademark))+TX, Azotobacter chroococcum, especially strain H23+TX, Azotobacter vinelandii, especially strain ATCC 12837+TX, Bacillus amyloliquefaciens BS27 (accession number NRRL B-5015)+TX, Bacillus amyloliquefaciens, especially strain FZB42 (e.g., ABiTEP, DE RHIZOVITAL(registered trademark))+TX, Bacillus amyloliquefaciens, especially strain IN937a+TX, Bacillus amyloliquefaciens Bacillus amyloliquefaciens)pm414 (LOLI-PEPTA® registered trademark of Biofilm Crop Protection) + TX, Bacillus amyloliquefaciens SB3281 (ATCC # PTA-7542, International Publication No. 2017 / 205258) + TX, Bacillus amyloliquefaciens TJ1000 (available from Novozymes as QUIKROOTS® registered trademark) + TX, Bacillus cereus family member EE128 (NRRL No. B-50917) + TX, Bacillus cereus family member EE349 (NRRL No. B-50928) + TX, Bacillus cereus Bacillus mycoides) particularly strain BP01 (ATCC 55675, e.g., Arysta Lifescience, MEPICHLOR® of the US) + TX, Bacillus mycoides BT155 (NRRL No. B-50921) + TX, Bacillus mycoides BT46-3 (NRRL No. B-50922) + TX, Bacillus mycoides EE118 (NRRL No.B-50918)+TX, Bacillus mycoides EE141 (NRRL No. B-50916)+TX, Bacillus pumilus strain GB34 (e.g., Bayer Crop Science, DE YIELD SHIELD®),+TX, Bacillus pumilus strain QST2808 (Accession No. NRRL No. B-30087)+TX, Bacillus siamensis strain KCTC 13613T+TX, Bacillus subtilis strain AQ30002 (Accession No. NRRL Bacillus subtilis strain AQ30004 (as described in NRRL No. B-50455 and U.S. Patent Application No. 13 / 330,576) + TX, Bacillus subtilis strain MBI 600 (e.g., SUBTILEX® from BASF SE) + TX, Bacillus subtilis rm303 (RHIZOMAX® from Biofilm Crop Protection) + TX, Bacillus subtilis strain BU1814 (available as TEQUALIS® from BASF SE) + TX, Bacillus tequilensis tequilensis) especially strain NII-0943+TX, Bacillus thuringiensis BT013A (NRRL No.B-50924) Also known as Bacillus thuringiensis 4Q7+TX, Bradyrhizobium japonicum (e.g., Novozymes' OPTIMIZE®)+TX, Delftia acidovorans, especially strain RAY209 (e.g., Brett Young Seeds' BIOBOOST®)+TX, Lactobacillus species (e.g., LACTOPLANT® from LactoPAFI)+TX, Mesorhizobium cicer (e.g., BASF SE's NODULATOR)+TX, Paenibacillus polymyxa, especially strain AC-1 (e.g., Green Biotech Company TOPSEED (registered trademark) of Ltd. +TX, Pseudomonas aeruginosa, especially strain PN1 +TX, Pseudomonas proradix (e.g., PRORADIX (registered trademark) of Sourcon Padena) +TX, Rhizobium leguminosarium biovar viciae (e.g., NODULATOR of BASF SE) +TX, Rhizobium leguminosarum, especially bv. viceae strain Z25 (accession number CECT 4585) +TX, Serratia marcescens, especially strain SRM (accession number MTCC 8708), +TX, Sinorhizobium melilotii meliloti) strain NRG-185-1 (NITRAGIN® GOLD from Bayer CropScience) + TX; Thiobacillus sp. (e.g., CROPAID® from Cropaid Ltd UK) + TX; Myrothecium verrucaria strain AARC-0255 (e.g., DiTera® from Valent Biosciences) + TX, Penicillium bilaii strain ATCC 22348 (e.g., JumpStart® from Acceleron BioAg) + TX, Penicillium bilaii strain ATCC ATCC20851 + TX, Purpureocillium lilacinum (formerly known as Paecilomyces lilacinus) strain 251 (AGAL 89 / 030550, e.g., BioAct from Bayer CropScience Biologics GmbH) + TX, Pythium oliligandrum Pythium oligandrum strain DV74 + TX, Pythium oligandrum strain M1 (ATCC 38472, e.g., Polyversum of Bioprepraty, CZ) + TX, Rhizopogon amylopogon (Myco-Sol of Agri-Enterprise, LLC, formerly Helena Chemical Company) + TX, Rhizopogon fulvigleba (Myco-Sol of Agri-Enterprise, LLC, formerly Helena Chemical Company) + TX, Talaromyces flavus strain V117b + TX, Trichoderma asperellum strain (Eco-T of Plant Health Products, ZA) + TX, Trichoderma asperellum Asperellum strain KD (e.g., Andermatt Biocontrol's T-Gro) + TX, Trichoderma atroviride strain No.V08 / 002387+TX, Trichoderma atroviride strain CNCM 1-1237 (e.g., Agrauxine, Esquive® WP, FR)+TX, Trichoderma atroviride strain LC52 (also known as Trichoderma atroviride strain LU132, e.g., Sentinel, Agrimm Technologies Limited)+TX, Trichoderma atroviride strain no. NMI No. V08 / 002388+TX, Trichoderma atroviride strain no. NMI No. V08 / 002389+TX, Trichoderma atroviride strain no. NMI No.V08 / 002390+TX, Trichoderma atroviride strain SC1 (described in International Publication No. 2009 / 116106)+TX, Trichoderma harzianum strain 1295-22+TX, Trichoderma harzianum strain ITEM 908+TX, Trichoderma harzianum strain T-22 (e.g., Andermatt Biocontrol or Koppert's Trianum-P from)+TX, Trichoderma harzianum strain TSTh20+TX, Trichoderma virens strain GI-3+TX, Trichoderma virens virens) strain GL-21 (e.g., Certis, USA, SoilGard®) + TX, Trichoderma viride strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161:125-137) + TX, Verticillium albo-atrum (formerly V. dahliae (V.dahliae)) Stock WCS850 (CBS 276.92, e.g., Dutch Trig from Tree Care Innovations) + TX;. Agrobacterium radiobacter strain K84 (Galltrol, AgBiochem Inc.) + TX, Bacillus amyloliquefaciens strain PTS-4838 (e.g., AVEO, Valent Biosciences, US) + TX, Bacillus mycoides isolate J. (e.g., BmJ, Certis USA LLC) + TX, Bacillus sphaericus strain 2362 serotype H5a5b (ABTS-1743) (e.g., VECTOLEX®, Valent BioSciences, US) + TX, Bacillus thuringiensis israelensis strain BMP 144 (e.g., Becker Microbial Products) AQUABAC® (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. Israelensis (serotype H-14) strain AM65-52 (accession number ATCC 1276) (e.g., Valent BioSciences, VECTOBAC® in the US) + TX, Bacillus thuringiensis subsp. crustachyBacillus thuringiensis subsp. kurstaki strain ABTS 351 + TX, Bacillus thuringiensis subsp. kurstaki strain BMP 123 (Becker Microbial Products, IL, Bayer CropScience BARITONE) + TX, Bacillus thuringiensis subsp. kurstaki strain EG 2348 (Certis, US LEPINOX) + TX, Bacillus thuringiensis subsp. kurstaki strain EG 7841 (Certis, US CRYMAX) + TX, Bacillus thuringiensis subsp. kurstaki strain HD-1 (e.g., Valent BioSciences, US DIPEL® ES)+TX, Bacillus thuringiensis subsp. kurstaki strain PB 54+TX, Bacillus thuringiensis subsp. kurstaki strain SA 11 (Certis, US JAVELIN)+TX, Bacillus thuringiensis subsp. kurstaki strain SA 12 (Certis, US THURICIDE)+TX, Bacillus thuringiensis subsp. tenebrionis strain NB 176 (SD-5428, e.g., BioFa DE NOVODOR® FC)+TX, Bacillus thuringiensis variety colmelii (Bacillus Bacillus thuringiensis var. colmeri) (e.g., TIANBAOBTC at Changzhou Jianghai Chemical Factory) + TX, Bacillus thuringiensis var. japonensisjaponensis) 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) (Accession number NRRL B-50319, International Publication No. 2011 / 106491 and International Publication No. 2013 / 032693, e.g., MBI206 from Marrone Bio Innovations) TGAI and ZELTO (registered trademarks) + TX, Chromobacterium subtsugae, especially strain PRAA4-1T (e.g., MBI-203, e.g., GRANDEVO (registered trademark) of Marrone Bio Innovations) + TX, Lecanicillium muscarium Ve6 (MYCOTAL of Koppert) + TX, Paenibacillus popilliae (formerly Bacillus popilliae, e.g., St.Gabriel Laboratories' MILKY SPORE POWDER (trademark) or MILKY SPORE GRANULAR (trademark) + TX; Serratia entomophila (e.g., Wrightson Seeds' INVADE (registered trademark)) + TX; Serratia marcescens, especially strain SRM (accession number MTCC 8708) + TX; Trichoderma asperellum (Novozymes' TRICHODERMAX) + TX; Wolbachia pipientis, ZAP strain (e.g., MosquitoMate's ZAP MALES (registered trademark)) + TX; Beauveria bassiana strain ATCC 74040 (e.g., NATURALIS® from Intrachem Bio Italia) + TX; Beauveria bassiana strain ATP02 (accession number DSM24665), Apopka 97 (PREFERAL® from SePRO) + TX; Beauveria bassiana strain GHA (accession number ATCC74250, e.g., BOTANIGUARD® ES and MYCONTROL-O® from Laveriam International Corporation) + TX; Metarhizium anisopliae 3213-1 (deposited under NRRL accession number 67074, disclosed in International Publication No. 2017 / 066094; Pioneer Hi-Bred International)+TX; Metarhizium robertsii 15013-1 (deposited under NRRL receipt number 67073)+TX; Metarhizium robertsii 23013-3 (deposited under NRRL receipt number 67075)+TX; Paecilomyces lilacinus strain 251 (MELOCON® registered trademark from Certis, US)+TX; Cydia pomonella (codling moth) granule virus (GV) + TX, Helicoverpa armigera (tobacco budworm) nuclear polyhedra virus (NPV) + TX, Adoxophyes Orana (summer fruit tortrix moth) granule virus (GV) + TX, Spodoptera exigua (white fall armyworm) mNPV + TX, Spodoptera frugiperda (white fall armyworm) + TX; Burkholderia spp., especially Burkholderia cepacia (formerly known as Pseudomonas cepacia) + TX, Gigaspora spp. + TX, Glomus spp. + TX, Laccaria spp. + TX, Lactobacillus buchneri + TX, Paraglomus spp. + TX, Pisolithus tinctorus + TX, Pseudomonas spp. + TX, Rhizobium spp., especially Rhizobium trifolia (trifolii)+TX, Rhizopogon spp.+TX, Scleoderma spp.+TX, Streptomyces spp.+TX, Suillus spp.+TX, Agrobacterium spp.+TX, Azorhizobium caulinodans+TX, Azospirillum spp.+TX, Azotobacter spp.+TX, Bradyrhizobium spp.+TX, Gigaspora monosporum+TX; Allium sativum (NEMGUARD Eco-Spray, BRALIC ADAMA) + TX, Armour-Zen + TX, Artemisia absinthium + TX, Biokeeper WP + TX, Brassicaceae extract, especially Brassica napus powder or mustard powder + TX, Cassia nigricans + TX, Celastrus angulatus + TX, Chenopodium anthelminticum + TX, Chenopodium quinoa saponin extract from quinoa seeds (e.g., Heads Up plant Protectants, Heads Up® CA (Saponins of Quinoa)) + TX, Chitin + TX, Dryopteris filix-mas)+TX, Equisetum arvense+TX, Fortune Aza+TX, Fungastop+TX, Melaleuca alternifolia extract (STK's TIMOREX GOLD)+TX, Naturally occurring Blad polypeptide extract from Lupin seeds (FMC's FRACTURE®)+TX, Naturally occurring Blad polypeptide extract from Lupin seeds (Certis EU's PROBLAD®)+TX, Pyrethrin+TX, Auassia amara+TX, Quercus+TX, Quillaja extract (BASF's QL AGRI 35)+TX, Marrone Bio's REGALIA MAXX+TX, Requiem® insecticide+TX, Reynoutria saccharinensis Sachalinensis extract (REGALLIA+TX, liany / lianodine+TX, Symphytum officinale+TX, Tansy (Tanacetum vulgare)+TX, Thymol+TX, Thymol mixed with geraniol (EdenResearch's CEDROZ) + TX, thymol mixed with geraniol and eugenol (Eden Research's MEVALONE) + TX, Triact 70 + TX, TriCon + TX, nasturtium (Tropaeulum majus) + TX, stinging nettle (Urtica dioica) + TX, veratrine + TX, mistletoe (Viscum album) + TX; Mercuric oxide + TX, octylinone + TX, thiophanate-methyl + TX; MGK 264+TX, 2-(2-butoxyethoxy)ethylPiperonilate + TX, 2-Isovalerylindan-1,3-dione + TX, 4-(Quinoxaline-2-ylamino)benzenesulfonamide + TX, 5-(1,3-Benzodioxol-5-yl)-3-hexylcyclohexa-2-enone + TX, Acibenzolar + TX, Acibenzolar-S-methyl + TX, α-Bromadiolone + TX, α-Chlorohydrin + TX, Aluminum phosphide + TX, Anthraquinone + TX, Ants + TX, Arsenous acid + TX, Barium carbonate + TX, Benoxacol + TX, Bisthiosemi + TX, Brodifacum + TX Bromadiolon + TX, Bromethaline + TX, Calcium cyanide + TX, Chloralose + TX, Chlorophacinone + TX, Cholecalciferol + TX, Chloquintoset (including Chloquintoset-Mexyl) + TX, Copper naphthenate + TX, Copper oxychloride + TX, Coumaflyl + TX, Coumatetralyl + TX, Crimidine + TX, Cyprosulfamide + TX, Diazinon + TX, Dichlormid + TX, Dicyclopentadiene + TX, Diphenacome + TX, Difethiaron + TX, Diphacinone + TX, Ergocalciferol Electrolyte + TX, Farnesol + TX, Farnesol and Nerolidol + TX, Fenchlorazole (containing fenchlorazole-ethyl) + TX, Fenchlorim + TX, Furocumafen + TX, Fluoroacetamide + TX, Flupropazine + TX, Flupropazine hydrochloride + TX, Fluxofenim + TX, Frillazole + TX, Gamma-HCH + TX, Guazatine + TX, Guazatine acetate + TX, HCH + TX, Hydrogen cyanide + TX, Imanin + TX, Iodomethane + TX, Isoxadifen (containing isoxadifen-ethyl) + TX, Linde +TX, Magnesium phosphide +TX, MB-599 +TX, Mefenydr (containing Mefenydr-diethyl) +TX, Metocamifen +TX, Methiocarb +TX, Methyl bromide +TX, Nerolidol +TX, Norbolmid +TX, Petroleum +TX, Fosacetim +TX, Phosphine +TX, Phosphate +TX, Phosphate +TX, Pindone +TX, Piperonyl butoxide +TX, Piprotal +TX, Potassium arsenite +TX, Probenazole +TX, Propyl isomer +TX, Pyridine-4-amine +TX, Pyrynulone +TX, Reynoutria saccharinensisSachalinensis extract + TX, ribavirin + TX, S421 + TX, siriloside + TX, sesamex + TX, sesasmorin + TX, sodium arsenite + TX, sodium cyanide + TX, sodium fluoroacetate + TX, strychnine + TX, sulfoxide + TX, thallium sulfate + TX, thyram + TX, trimetacarb + TX, warfarin + TX, zinc naphthenate + TX, zinc phosphide + TX, ziram + TX.
[0154] 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, for example, as described in U.S. Patent No. 6,919,298, and include, for example, salicylates and the commercially available SAR inducer acibenzolar-S-methyl.
[0155] 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.
[0156] 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.
[0157] Accordingly, the present invention provides a composition, preferably a fungicidal composition, comprising at least one compound of formula (I) as defined in the present invention, an agriculturally acceptable carrier, and optionally an auxiliary agent. The agriculturally acceptable carrier is, for example, a carrier suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, in addition to the compound of formula (I) as defined in the present invention, the composition may contain at least one or more pesticides, such as additional fungicidal active ingredients.
[0158] Further aspects of the present invention relate to methods for controlling or preventing ectoparasitism by potentially harmful plant pathogenic or putrefactive microorganisms or organisms, particularly fungi, of plants, such as useful plants, such as crop plants, their reproductive materials, such as seeds, harvested crops, such as harvested food crops, or non-biological materials, the methods comprising the application of compounds of formula (I) as defined in the present invention, or preferred individual compounds as defined above as active ingredients for plants, to plants, to parts of plants or their habitats, to their reproductive materials, or to any part of non-biological materials.
[0159] Control or prevention means reducing ectopic parasites by insects, plant pathogenic or putrefactive microorganisms, or organisms potentially harmful to humans, particularly fungi, to a level where improvement is demonstrated.
[0160] A preferred method for controlling or preventing ectoparasitism of crop plants by plant pathogenic microorganisms, particularly fungi, is foliar application, which includes 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. The frequency and amount of application will depend on the risk of ectoparasitism by the corresponding pathogen or insect. However, the compound of formula (I) as defined in the present invention can also be introduced into plants through the soil via the roots (osmotic action) by drenching the plant habitat with a liquid formulation or by applying the compound in solid form, such as granular form, to the soil (soil application). In rice crops, such granular material can be applied to flooded paddy fields. The compound of formula (I) as defined in the present invention can also be applied to seeds (coating) by either impregnating the seeds or tubers with a liquid formulation of the fungicide or coating them with a solid formulation.
[0161] A composition containing a compound of formula (I) as defined in the present invention, and optionally a solid or liquid additive or a monomer for encapsulating the compound of formula (I) as defined in the present invention, can be prepared by known methods, typically by closely mixing and / or grinding the compound with an extender, such as a solvent, a solid carrier, and optionally a surfactant.
[0162] Other subjects of the present invention include methods for applying the composition, i.e., methods for controlling the above-mentioned types of pathogens, such as spraying, misting, dusting, brushing, powdering, diffusion, or pouring (these should be selected according to the intended purpose of the general situation), and the use of the composition for controlling the above-mentioned types of pathogens. 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 application rate is 10 mg to 1 g of the active substance per kg of seed.
[0163] When the combination of the present invention is used for seed treatment, it is generally sufficient to use a ratio of the compound of formula (I) of 0.001 to 50 g per kg of seed, preferably 0.01 to 10 g per kg of seed.
[0164] 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).
[0165] 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.
[0166] Such compositions can be produced by conventional methods, for example, by mixing an active ingredient with a suitable formulation deactivator (diluent, solvent, filler, and optionally other formulation components such as surfactants, biocides, antifreezes, spreading agents, thickeners, and compounds that provide auxiliary effects). Conventional sustained-release formulations can also be used when sustained effectiveness over a long period is desired. In particular, formulations applied in spray form, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules, may contain surfactants, such as wetting agents and dispersants, and other compounds that provide auxiliary effects, such as formaldehyde, and condensation products of naphthalene sulfonates, alkylaryl sulfonates, lignin sulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated fatty alcohols.
[0167] 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, for example, as a slow-release capsule or microcapsule.
[0168] 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.
[0169] While it is preferable to incorporate commercially available products as concentrates, end users typically utilize dilute formulations. [Examples]
[0170] The following examples illustrate the present invention. Certain compounds of the present invention can be distinguished from known compounds by their greater potency at lower doses, which can be verified by those skilled in the art using the experimental procedures outlined in the examples.
[0171] Combination example
[0172] [Table 2]
[0173] By thoroughly mixing the active ingredient with an auxiliary agent and thoroughly grinding the mixture in a suitable pulverizer, a wettable powder can be obtained that can be diluted with water to form a suspension of the desired concentration.
[0174] [Table 3]
[0175] By thoroughly mixing the active ingredient with an auxiliary agent and thoroughly grinding the mixture in a suitable grinder, a powder that can be used directly for seed treatment can be obtained.
[0176] 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%
[0177] Emulsions of any required dilution suitable for plant protection can be obtained from this concentrate by dilution with water.
[0178] [Table 4]
[0179] Ready-to-use powders are obtained by mixing the active ingredient with a carrier and grinding the mixture in a suitable pulverizer. Such powders can also be used for drying and coating seeds.
[0180] Extruded granules Active ingredient [compound of formula (I)] 15% Sodium lignin sulfonate 2% Carboxymethylcellulose 1% Kaolin 82%
[0181] The active ingredient is mixed with an auxiliary agent and ground, and the mixture is moistened with water. The mixture is then extruded and dried in an airflow.
[0182] Coated granules Active ingredient [compound of formula (I)] 8% Polyethylene glycol (molecular weight 200) 3% Kaolin 89%
[0183] The finely ground active ingredient is uniformly added to kaolin moistened with polyethylene glycol in a mixer. A non-dusting coated granule is thus obtained.
[0184] 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%
[0185] By tightly mixing the finely ground active ingredient with an auxiliary agent, a suspension concentrate can be obtained, and by diluting it with water, a suspension of the desired dilution can be obtained. Using such a dilution, not only growing plants but also plant propagation materials can be treated by spraying, pouring, or immersion to protect them from microbial ectoplasty.
[0186] 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%
[0187] By tightly mixing the finely ground active ingredient with an auxiliary agent, a suspension concentrate can be obtained, and by diluting it with water, a suspension of the desired dilution can be obtained. Using such a dilution, not only growing plants but also plant propagation materials can be treated by spraying, pouring, or immersion to protect them from microbial ectoplasty.
[0188] Sustained-release capsule suspension Mix 28 parts of the compound combination of formula (I) with 2 parts of aromatic solvent and 7 parts of a toluene diisocyanate / polymethylene-polyphenyl isocyanate mixture (8:1). Emulsify this mixture in a mixture of 1.2 parts polyvinyl alcohol, 0.05 parts defoamer, and 51.6 parts water until the desired particle size is reached. Add a mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts water to this emulsion. Stir the mixture until the polymerization reaction is complete.
[0189] The resulting capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersant. The capsule suspension formulation contains 28% of the active ingredient. The diameter of the capsules is 8 to 15 micrometers.
[0190] The resulting formulation is applied to seeds as an aqueous suspension using equipment suitable for the purpose.
[0191] 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.
[0192] Method A: Equipment: Shimadzu LCMS 2020 mass spectrometer; Column: HALOC 18 2.7 μm, 3.0 mm × 30 mm; Mobile phase: MeCN (containing either 0.05% HCOOH or 0.05% TFA) - Water (containing either 0.05% HCOOH or 0.05% TFA); Gradient: 5% to 95% MeCN over 1.4 min, hold for 0.6 min, total run time 2.5 min; Flow rate: 1.8 mL / min; Column temperature: 50°C; Wavelength: 214 and 254 nm PDA.
[0193] Method B: Spectra were recorded using a Waters mass spectrometer (Acquity QDa mass spectrometer) equipped with an electrospray source (polarity: positive and negative polarity switch), capillary: 0.8kV, cone range: 25V, extractor: V (no extraction voltage for QDa detector), source temperature: 120℃, desolvation temperature: 600℃, cone gas flow rate: 50L / h, desolvation gas flow rate: 1000L / h, mass range: 110~850Da), and a Waters Acquity UPLC (Quaterary Solvent Manager), heated column compartment, and diode array detector. Column: Acquity UPLC HSS T3 C18, 1.8μm, 30×2.1mm, temperature: 40℃, DAD wavelength range (nm): 200~400, solvent gradient: A = water + 5% acetonitrile + 0.05% HCOOH, B = acetonitrile + 0.1% HCOOH. Gradient: 10% B for 0 minutes; 10-50% B for 0-0.2 minutes; 50-100% B for 0.2-0.6 minutes; 100% B for 0.6-1.3 minutes; 100-10% B for 1.3-1.4 minutes; 10% B fo...
Claims
1. Equation (I) 【Chemistry 1】 (wherein Z is O or S, preferably Z is O; A 1 is CH or N, preferably N; R 1a is selected from 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; R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 Selected independently of alkyl; A 2 CR is independent 2 or N, provided there are three or fewer A's. 2 is N, preferably two or fewer A 2 is N, preferably one or less A 2 N is 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 is independent 3 or N; R 3 is selected from hydrogen, hydroxy, halogen, CN, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkoxy, C 2-6 alkenyl, C 2-6 alkynyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-6 alkyl, C 1-6 alkylsulfanyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, amino, C 1-6 alkylamino, diC 1-6 -alkylamino, and C 3-6 cycloalkylamino, 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 cycloalkylamino group may be optionally substituted with 1 to 3 substituents independently selected from halogen, hydroxy, and CN; 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, more preferably a 5- to 8-membered heteroring, more preferably a 6-membered heteroring; R 5 C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, diC 1-6 Alkylamino, and C 1-6 Alkyl C 1-6 Selected from alkoxyaminos, where each of the groups may be optionally substituted with one to three substituents independently selected from halogens and CNs; A compound of the same, or its salt or N-oxide.
2. R 1a However, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxys, preferably C 1-6 The compound according to claim 1, wherein it is alkyl.
3. R 1b and R 1c However, hydrogen, C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 A compound according to claim 1 or 2, independently selected from alkoxys.
4. R 1a However, 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 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, R 1b and R 1c The compound according to claim 1, wherein the compound is hydrogen.
5. R 2 However, hydrogen, hydroxyl, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, and C 1-6 Independently selected from alkylcarbonyls, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 1-6 Alkoxycarbonyl, C 1-6 Alkylaminocarbonyl, diC 1-6 Alkylaminocarbonyl, and C 1-6 The compound according to any one of claims 1 to 4, wherein each alkylcarbonyl group may be optionally substituted with one to three substituents independently selected from halogen, hydroxyl, and CN.
6. R 3 However, hydrogen, hydroxyl, halogen, CN, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, amino, C 1-6 Alkylamino, diC 1-6 - Alkylamino, and C 3-6 Selected from 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 5, wherein each cycloalkylamino group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs.
7. The four A's 2 CR 2 A 3 A compound according to any one of claims 1 to 6, wherein is N. 【Request Item 8】 【Chemistry 2】 but 【Transformation 3】 Preferably three A 2 CR 2 A 3 CR 3 The compound according to any one of claims 1 to 6. 【Request Item 9】 【Chemistry 4】 but 【Transformation 5】 Preferably three A 2 CR 2 A 3 CR 3 The compound according to any one of claims 1 to 6.
10. The four A's 2 CR 2 A 3 CR 3 Preferably 【Transformation 6】 but 【Transformation 7】 The compound according to any one of claims 1 to 6.
11. R 4 However, C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl and C 1-6 Selected from alkoxy, 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 C 1-6 The compound according to any one of claims 1 to 10, wherein each alkoxy group may be optionally substituted with one to three substituents independently selected from halogens and CNs.
12. R 5 However, C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl and C 1-6 Alkoxy C 1-6 The compound according to any one of claims 1 to 11, wherein each of the alkyl 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 mixture thereof.
15. A method for eradicating, preventing, or controlling plant pathogenic diseases, comprising applying a fungicidal amount to a plant pathogen, a habitat of the plant pathogen, a plant susceptible to damage by the plant pathogen, or the plant's reproductive material, either a compound according to any one of claims 1 to 12 or a composition containing the compound according to any one of claims 1 to 12 or a composition according to claim 13 or 14.
16. Formula (IV) 【Transformation 8】 (wherein Z is O or S, preferably Z is O; R 1a is 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 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 Selected from alkyl groups, preferably R 1a C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy; R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Selected independently of alkyl groups; preferably, R 1b and R 1c is hydrogen; A 2 CR is independent 2 or N, provided there are three or fewer A's. 2 is N, preferably two or fewer A 2 is N, preferably one or less A 2 N is 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; 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 from alkoxy, where C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Each alkoxy group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs; A 3 CR is independent 3 or N; R 3 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, amino, C 1-6 Alkylamino, diC 1-6 - Alkylamino, and C 3-6 Selected from 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 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 one to three substituents independently selected from halogens, hydroxyls, and CNs; preferably, R 3 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, and C 1-6 Alkoxy-C 1-6 Selected from alkyl, where C 1-6 Alkyl, C 1-6 Alkoxy, and C 1-6 Alkoxy-C 1-6 Each alkyl group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs; R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl, diC 1-6 Alkylaminocarbonyl-C 1-6 Selected from alkyl and CN, 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; 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; and A 3 and R 4 They can optionally come together to form a ring, more preferably a 5- to 8-membered heteroring, or more preferably a 6-membered heteroring); Compounds of or salts or N-oxides thereof; Or Formula (II) 【Chemistry 9】 (wherein Z is O or S, preferably Z is O; R 1a is 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 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 Selected from alkyl groups; preferably, R 1a C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy; R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Selected independently of alkyl groups; preferably, R 1b and R 1c is hydrogen; A 2 CR is independent 2 or N, provided there are three or fewer A's. 2 is N, preferably two or fewer A 2 is N, preferably one or less A 2 N is 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; preferably, R 2 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl and C 1-6 Alkoxy-C 1-6 Selected independently from 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 alkoxy group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs; A 3 CR is independent 3 or N; R 3 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Alkoxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkoxy, C 2-6 Alkenil, C 2-6 Alkinyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, amino, C 1-6 Alkylamino, diC 1-6 - Alkylamino, and C 3-6 Selected from 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 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 one to three substituents independently selected from halogens, hydroxyls, and CNs; preferably, R 3 These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 1-6 Alkoxy, and C 1-6 Alkoxy-C 1-6 Selected from alkyl, where C 1-6 Alkyl, C 1-6 Alkoxy, and C 1-6 Alkoxy-C 1-6 Each alkyl group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs; R 4 C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 2-6 Alkenil, C 2-6 Alkinyl, C 1-6 Alkoxy, C 1-6 Alkylsulfanyl-C 1-6 Alkyl, C 1-6 Alkylsulfinyl-C 1-6 Alkyl, C 1-6 Alkylsulfonyl-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, C 1-6 Alkylaminocarbonyl-C 1-6 Alkyl, diC 1-6 Alkylaminocarbonyl-C 1-6 Selected from alkyl and CN, 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; 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, more preferably a 5- to 8-membered heteroring, more preferably a 6-membered heteroring; X is Cl, Br, or I); A compound of the same, or its salt or N-oxide.
17. Formula (XXXVI) 【Chemistry 10】 (In the formula, A 1 is CH or N, preferably N; R 1a is 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 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 Selected from alkyl groups; preferably, R 1a C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy; R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Selected independently of alkyl groups; preferably, R 1b and R 1c is hydrogen; and R 5 C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, diC 1-6 Alkylamino, and C 1-6 Alkyl C 1-6 Selected from alkoxyaminos, where each of the groups may be optionally substituted with one to three substituents independently selected from halogens and CNs. Compounds of or salts or N-oxides thereof; Or Formula (XXXVIII) 【Chemistry 11】 (In the formula, A 1 is CH or N, preferably N; R 1a is 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 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 Selected from alkyl groups; preferably, R 1a C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy; R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Selected independently of alkyl groups; preferably, R 1b and R 1c is hydrogen; R 5 C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, diC 1-6 Alkylamino, and C 1-6 Alkyl C 1-6 Selected from alkoxyaminos, where each of the groups may be optionally substituted with one to three substituents independently selected from halogens and CNs; R 10 is C 1-6 (It is alkyl); Compounds of or salts or N-oxides thereof; Or Formula (XL) 【Chemistry 12】 (In the formula, A 1 is CH or N, preferably N; R 1a is 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 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino and NHC(O)C 1-6 Selected from alkyl groups; preferably, R 1a C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl and C 1-6 Selected from alkoxy; R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Selected independently of alkyl groups; preferably, R 1b and R 1c is hydrogen; R 5 C 1-6 Alkyl, C 1-6 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Cycloalkyl-C 1-6 Alkyl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylamino, diC 1-6 Alkylamino, and C 1-6 Alkyl C 1-6 Selected from alkoxyaminos, where each of the groups may be optionally substituted with one to three substituents independently selected from halogens and CNs; X is Cl, Br, or I); A compound of the same, or its salt or N-oxide.
18. Formula (XVI) 【Chemistry 13】 (wherein Z is O or S, preferably Z is O; R 1b and R 1c These are hydrogen, hydroxyl, halogen, CN, and C 1-6 Alkyl, C 3-6 Cycloalkyl, C 1-6 Alkoxy-C 1-6 Alkyl, C 3-6 Cycloalkyl-C 1-4 Alkyl, C 1-6 Alkyl sulfanyl, C 1-6 Alkyl sulfinyl, C 1-6 Alkyl sulfonyl, C 1-6 Alkoxy, amino, and NHC(O)C 1-6 Selected independently of alkyl groups; preferably, R 1b and R 1c is hydrogen; A 2 CR is independent 2 or N, provided there are three or fewer A's. 2 is N, preferably two or fewer A 2 is N, preferably one or less A 2 N is 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; 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 from 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 alkoxy group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs; A 3 is, independently, 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<00 1-6 Alkoxy, and C 1-6 Alkoxy-C 1-6 Each alkyl group may be optionally substituted with one to three substituents independently selected from halogens, hydroxyls, and CNs; R 4 is C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 alkoxy, C 1-6 alkylsulfanyl-C 1-6 alkyl, C 1-6 alkylsulfinyl-C 1-6 alkyl, C 1-6 alkylsulfonyl-C 1-6 alkyl, C 1-6 alkoxycarbonyl-C 1-6 alkyl, C 1-6 alkylaminocarbonyl-C 1-6 alkyl, di-C 1-6 alkylaminocarbonyl-C 1-6 alkyl, and CN, where the C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 alkoxy, C 1-6 alkylsulfanyl-C[[ID=!65]] 1-6 alkyl, C 1-6 alkylsulfinyl-C 1-6 alkyl, C 1-6 alkylsulfonyl-C 1-6 alkyl, C 1-6 alkoxycarbonyl-C 1-6 alkyl, C 1-6 alkylaminocarbonyl-C 1-6 alkyl and di-C 1-6 alkylaminocarbonyl-C 1-6 each of the alkyl groups may be optionally substituted by 1 to 3 substituents independently selected from halogen 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 one to three substituents independently selected from halogens and CNs; A 3 and R 4 They may optionally come together to form a ring, more preferably a 5- to 8-membered heteroring, more preferably a 6-membered heteroring; X is Cl, Br, or I); A compound of the same, or its salt or N-oxide.