Pyrazole compound

Abstract

The present disclosure addresses the problem of providing a novel compound or a novel agrochemical. Provided is a pyrazole compound represented by general formula (1) (where: A represents iodine, optionally substituted alkynyl, or the like; Z represents an optionally substituted divalent carbocyclic ring or the like; X represents an oxygen atom or carbonyl (C=O); T represents an oxygen atom or a sulfur atom; L represents optionally substituted alkyl or the like; R1 represents a hydrogen atom or the like; R2 represents a hydrogen atom or the like; and R3 represents a hydrogen atom or the like). Also provided is a structural isomer of the pyrazole compound, or a salt of the pyrazole compound or of the structural isomer.

Description

Pyrazole compounds

[0001] This disclosure relates to pyrazole compounds, etc.

[0002] Because pathogens can develop resistance to pesticides when used over many years, there is a need for new pesticides with superior control effects.

[0003] For example, Patent Documents 1 and 2 describe pyrazole compounds or salts thereof represented by the following general formula (P1), and these compounds are ether-bonded pyrazole compounds or salts thereof, having a G-O- group at the 4-position of the pyrazole ring, where G has the structure of G-1.

[0004]

[0005] These patent documents 1 and 2 state that in G-1, m5 is an integer of 0, 1, 2, 3, 4, or 5, and G １ Examples include "halogens."

[0006] However, while Patent Documents 1 and 2 state that G1 may include halogens, they do not describe specific examples where G1 is an iodine atom, nor do they offer any technical suggestions for selecting iodine substitution. Generally, iodine atoms have a relatively large influence on physical properties such as atomic radius and hydrophobicity, and are also subject to synthetic constraints, so it cannot be said that they would be automatically adopted by those skilled in the art as a simple substitution design on the same level as other halogen substitutions. Therefore, there is no motivation to manufacture the disclosed compound in which G1 is an iodine atom based on the descriptions in Patent Documents 1 and 2. Furthermore, Patent Documents 1 and 2 do not disclose carbonyl-bonded pyrazole compounds or salts thereof having a G-C(=O)- group at the 4-position of the pyrazole ring. As described above, Patent Documents 1 and 2 do not disclose G in ether-bonded compounds having a G-O- group at the 4-position of the pyrazole ring. １ As a group, (i) no compounds in which A is iodine, substituted alkynyl, substituted alkenyl, substituted cycloalkyl, formyl, or substituted heterocycle are described or suggested. Furthermore, (ii) no carbonyl-bonded compounds or salts thereof having a G-C(=O)- group at the 4-position of the pyrazole ring are disclosed.

[0007] International Publication No. 2023 / 243678, International Publication No. 2024 / 204842

[0008] This disclosure aims to provide novel compounds or novel pesticides.

[0009] As a result of diligent research to solve the aforementioned problems, the present inventors have found that a pyrazole compound represented by the following general formula (1) or a salt thereof, as disclosed herein, has excellent pest control effects as an agricultural chemical. This disclosure is completed based on these findings.

[0010] In other words, this disclosure is as follows:

[0011] Item 1. General formula (1):

[0012]

[0013] (In the formula, A represents iodine, optionally substituted alkynyl, substituted alkenyl, substituted cycloalkyl, formyl, or optionally substituted heterocyclic group. Z represents optionally substituted divalent carbocyclic group or optionally substituted divalent heterocyclic group. X represents an oxygen atom or carbonyl (C=O). T represents an oxygen atom or sulfur atom. L represents optionally substituted alkyl, optionally substituted carbocyclic, optionally substituted heterocyclic group, optionally substituted alkoxy, optionally substituted cycloalkoxy, optionally substituted aryloxy, or optionally substituted heteroaryloxy. １ R represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted carbon ring, or an optionally substituted heterocycle. ２ R represents a hydrogen atom, a halogen atom, an optionally substituted alkyl group, or an optionally substituted alkoxy group. ３represents a hydrogen atom, an alkyl which may have a substituent, an alkoxy which may have a substituent, an acyl which may have a substituent, an alkoxycarbonyl which may have a substituent, or a sulfonyl which may have a substituent. A pyrazole compound represented by the formula, a structural isomer thereof, or a salt thereof. Item 2. The pyrazole compound represented by the general formula (1), a structural isomer thereof, or a salt thereof is a compound represented by the following general formula (1-A) or a compound represented by the following general formula (1-B). The pyrazole compound according to Item 1, a structural isomer thereof, or a salt thereof.

[0014]

[0015] (In the formula, R ３Ａ represents a hydrogen atom, an alkyl which may have a substituent, an alkoxy which may have a substituent, an acyl which may have a substituent, an alkoxycarbonyl which may have a substituent, or a sulfonyl which may have a substituent. R ３Ｂ represents a hydrogen atom, an alkyl which may have a substituent, an acyl which may have a substituent, an alkoxycarbonyl which may have a substituent, or a sulfonyl which may have a substituent. T １ represents an oxygen atom or a sulfur atom. T ２ represents an oxygen atom or a sulfur atom. The wavy line represents the E configuration or Z configuration of the geometric isomer. The A, Z, X, L, R １ , and R ２(The same applies to the above.) Item 3. A pyrazole compound according to Item 1 or Item 2, its structural isomer, or a salt thereof, wherein X is an oxygen atom. Item 4. A pyrazole compound according to Item 1 or Item 2, its structural isomer, or a salt thereof, wherein X is a carbonyl (C=O) atom. Item 5. A pyrazole compound according to any one of Items 1 to 4, its structural isomer, or a salt thereof, wherein the pyrazole compound represented by the general formula (1), its structural isomer, or a salt thereof is an ether-type pyrazole compound represented by the following general formula (1A-A1), an ether-type pyrazole compound represented by the following general formula (1A-B1), a carbonyl-type pyrazole compound represented by the following general formula (1B-A1), or a carbonyl-type pyrazole compound represented by the following general formula (1B-B1).

[0016]

[0017] (In the formula, R Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , and R Ａ５ These are the same or different hydrogen atoms, hydroxyl, formyl, nitro, cyano, halogen atoms, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted alkylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted amino, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted cycloalkylaminocarbonyl, optionally substituted aminocarbonyl, -C(=NOR ６ ) R ７ The group represented by R is a silyl which may have a substituent, a carbon ring which may have a substituent, or a heterocycle which may have a substituent. ６ R represents a hydrogen atom or an alkyl group which may have a substituent. ７R represents an alkyl group which may have substituents. However, R Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , and R Ａ５ Of these, at least one represents iodine, an optionally substituted alkynyl, a substituted alkenyl, a substituted cycloalkyl, formyl, or an optionally substituted heterocycle. １ , T ２ , L, R １ , R ２ , R ３Ａ , R ３Ｂ , and the dashed lines are the same as above.) Item 6. A pyrazole compound represented by the general formula (1), its structural isomer, or a salt thereof, which is an ether-type pyrazole compound represented by the following general formula (1A-A2), an ether-type pyrazole compound represented by the following general formula (1A-B2), a carbonyl-type pyrazole compound represented by the following general formula (1B-A2), or a carbonyl-type pyrazole compound represented by the following general formula (1B-B2), as described in any one of items 1 to 4, its structural isomer, or a salt thereof.

[0018]

[0019] (In the formula, L １ is an oxygen atom, or -C(R) Ｌ１ ) (Caution Ｌ２ ) indicates the R Ｌ１ and R Ｌ２ R represents the same or different hydrogen atom or an alkyl group which may have a substituent. Ｌ１ and R Ｌ２ These two groups may bond to each other with adjacent carbon atoms to form a saturated or unsaturated carbon ring. The saturated or unsaturated carbon ring may further have substituents. ４ and R ５ R represents, either identically or differently, a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group, or an optionally substituted heterocycle. ４ and R ５These two groups may bond to each other with adjacent carbon atoms to form a saturated or unsaturated carbon ring. The saturated or unsaturated carbon ring may further have substituents. p represents an integer from 0 to 3. When p is 2 or 3, the two or three R ４ These may be the same or different, and the two or three R's mentioned above are... ５ They may be the same or different. Ｂ１ , R Ｂ２ , R Ｂ３ , R Ｂ４ , and R Ｂ５ These are the same or different hydrogen atoms, hydroxyl, formyl, nitro, cyano, halogen atoms, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted alkylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted amino, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted cycloalkylaminocarbonyl, optionally substituted aminocarbonyl, -C(=NOR ６ ) R ７ The group represented by R is a silyl which may have a substituent, a carbon ring which may have a substituent, or a heterocycle which may have a substituent. ６ R represents a hydrogen atom or an alkyl group which may have a substituent. ７ R represents an alkyl group which may have substituents. Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , R Ａ５ , T １ , T ２ , R １ , R ２ , R ３Ａ , R ３Ｂ , and the dashed line are the same as above.) Item 7. The R １However, the pyrazole compound according to any one of items 1 to 6, a structural isomer thereof, or a salt thereof, which is an alkyl which may have substituents. Item 8. The R ２ However, the pyrazole compound according to any one of items 1 to 7, its structural isomer, or a salt thereof, wherein A is a hydrogen atom. Item 9. The pyrazole compound according to any one of items 1 to 8, its structural isomer, or a salt thereof, wherein A is an alkynyl which may have substituents. Item 10. The pyrazole compound according to any one of items 1 to 9, its structural isomer, or a salt thereof, wherein A is iodine. Item 11. The L １ However, the oxygen atom is a pyrazole compound as described in any one of items 6 to 10, a structural isomer thereof, or a salt thereof. Item 12. The L １ However, -C(R Ｌ１ ) (Caution Ｌ２ ) - a pyrazole compound, a structural isomer thereof, or a salt thereof as described in any one of items 6 to 11. Item 13. A pyrazole compound, a structural isomer thereof, or a salt thereof as described in any one of items 6 to 12, wherein p is 1 or 2. Item 14. A pesticide containing one or more selected from the pyrazole compounds, structural isomers thereof, or salts thereof as described in any one of items 1 to 13 as an active ingredient. Item 15. A fungicide containing one or more selected from the pyrazole compounds, structural isomers thereof, or salts thereof as described in any one of items 1 to 13 as an active ingredient. Item 16. An intermediate compound for producing a pyrazole compound, a structural isomer thereof, or a salt thereof as described in any one of items 1 to 13, wherein the following general formula (2B):

[0020]

[0021] (In the formula, A represents iodine, optionally substituted alkynyl, substituted alkenyl, substituted cycloalkyl, formyl, or optionally substituted heterocyclic group. Z represents optionally substituted divalent carbocyclic group or optionally substituted divalent heterocyclic group. R Ｘ１ R represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted carbon ring, or an optionally substituted heterocycle.１ R represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted carbon ring, or an optionally substituted heterocycle. ２ Intermediate compounds represented by ) where represents a hydrogen atom, a halogen atom, an optionally substituted alkyl, or an optionally substituted alkoxy. Item 17. Intermediate compounds for producing any one of items 1 to 13, a pyrazole compound, a structural isomer thereof, or a salt thereof, wherein the following general formula (3B):

[0022]

[0023] (In the formula, A represents iodine, optionally substituted alkynyl, substituted alkenyl, substituted cycloalkyl, formyl, or optionally substituted heterocyclic group. Z represents optionally substituted divalent carbocyclic group or optionally substituted divalent heterocyclic group. R Ｘ１ R represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted carbon ring, or an optionally substituted heterocycle. Ｘ２ and R Ｘ３ An intermediate compound represented by ) which is the same or different alkyl, optionally substituted, optionally substituted carbon ring, or optionally substituted heterocycle.

[0024] Section 1A. General formula (1-0):

[0025]

[0026] (In the formula, A represents an optionally substituted alkynyl, substituted alkenyl, substituted cycloalkyl, formyl, or optionally substituted heterocycle. Z is a linking group, and the linking group represents an optionally substituted carbocyclic or optionally substituted heterocycle. X represents an oxygen atom. T represents an oxygen atom or a sulfur atom. R １ R represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted carbon ring, or an optionally substituted heterocycle. ２represents a hydrogen atom, a halogen atom, an alkyl which may have a substituent, or an alkoxy which may have a substituent. R ３ represents a hydrogen atom, an alkyl which may have a substituent, an alkoxy which may have a substituent, or an acyl which may have a substituent. L represents an alkyl which may have a substituent, a carbocyclic ring which may have a substituent, a heterocyclic ring which may have a substituent, an alkoxy which may have a substituent, an oxy having a carbocyclic ring which may have a substituent, or an oxy having a heterocyclic ring which may have a substituent. ) A pyrazole compound represented by or a salt thereof. Item 2A. The compound represented by the general formula (1-0) or a salt thereof is represented by the following general formula (1-1):

[0027]

[0028] (In the formula, R Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , and R Ａ５ are the same or different and are a hydrogen atom, hydroxy, formyl, nitro, cyano, a halogen atom, an alkyl which may have a substituent, a cycloalkyl which may have a substituent, an alkenyl which may have a substituent, an alkynyl which may have a substituent, an alkoxy which may have a substituent, an alkylthio which may have a substituent, an alkylsulfinyl which may have a substituent, an alkylsulfonyl which may have a substituent, an amino which may have a substituent, an alkylcarbonyl which may have a substituent, an alkoxycarbonyl which may have a substituent, an alkylaminocarbonyl which may have a substituent, a cycloalkylaminocarbonyl which may have a substituent, an aminocarbonyl which may have a substituent, -C(=NOR ６ )R ７ , an aryl which may have a substituent, or a heterocyclic ring which may have a substituent. The R ６ represents a hydrogen atom or an alkyl which may have a substituent. The R ７ represents an alkyl which may have a substituent. However, the R Ａ１ , R Ａ２ , RＡ３ , R Ａ４ , and R Ａ５ Among them, at least one represents alkynyl, substituted alkenyl, substituted cycloalkyl, formyl, or a heterocyclic ring which may have a substituent. The X, T, R １ , R ２ , R ３ , and L are the same as described above.) The pyrazole compound or a salt thereof according to Item 1A, which is a compound represented by the following. Item 3A. The compound represented by the general formula (1-1) or a salt thereof is represented by the following general formula (1-2):

[0029]

[0030] (In the formula, L １ represents an oxygen atom or -C(R Ｌ１ )(R Ｌ２ )-. The R Ｌ１ and the R Ｌ２ are the same or different and each represents a hydrogen atom or an alkyl group which may have a substituent. The R Ｌ１ and the R Ｌ２ may be bonded to each other together with the adjacent carbon atoms to form a saturated or unsaturated carbocyclic ring. The saturated or unsaturated carbocyclic ring may further have a substituent. R ４ , and R ５ are the same or different and each represents a hydrogen atom, a halogen atom, an alkyl which may have a substituent, a cycloalkyl which may have a substituent, an aryl which may have a substituent, or a heterocyclic ring which may have a substituent. The R ４ and R ５ may be bonded to each other together with the adjacent carbon atoms to form a saturated or unsaturated carbocyclic ring. The saturated or unsaturated carbocyclic ring may further have a substituent. p represents an integer of 0 to 3. When p is 2 or 3, the two or three R ４ may be the same or different, and the two or three R ５ may be the same or different. R Ｂ１ , R Ｂ２ , R Ｂ３ , R Ｂ４, and R Ｂ５ These are the same or different hydrogen atoms, hydroxyl, formyl, nitro, cyano, halogen atoms, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted alkylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted amino, optionally substituted acyl, -OR ｃ ,-NHC(O)R ｄ , -NR ｈ C(O)R ｅ , - NHSO ２ R ｆ -C≡CR ｇ , -SO ２ NH ２ , -C(=NOR ｈ ) R ｉ , represents a carbon ring which may have substituents, or a heterocycle which may have substituents. ｃ R represents an optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkylcarbonyl, optionally substituted aryl, optionally substituted heterocycle, or optionally substituted alkylaminocarbonyl. ｄ R represents an optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyloxy, optionally substituted alkylamino, benzyloxy, optionally substituted aryl, optionally substituted heterocyclic, or optionally substituted amino. ｅ R represents an optionally substituted alkyl, optionally substituted aryl, optionally substituted heterocycle, or optionally substituted amino. ｆ R represents an alkyl group which may have substituents. ｇ R represents a hydrogen atom or a tri(alkyl)silyl. ｈ R represents an alkyl group which may have a hydrogen atom or substituent.ｉ R represents an alkyl group which may have substituents. Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , R Ａ５ X, T, R １ , R ２ , and R ３ The same as above.) A pyrazole compound or salt thereof as described in item 2A, which is represented by ) Item 4A. The R １ However, the pyrazole compound or salt thereof according to any one of items 1A to 3A, which is an alkyl which may have substituents. Item 5A. The R ２ However, the pyrazole compound or salt thereof described in any one of items 1A to 4A, which is a hydrogen atom. Item 6A. The R ３ However, the pyrazole compound or salt thereof according to any one of items 1A to 5A, wherein A is a hydrogen atom. Item 7A. The pyrazole compound or salt thereof according to any one of items 1A to 6A, wherein A is an alkynyl which may have substituents, or a substituted alkenyl. Item 8A. The L １ However, the pyrazole compound or salt thereof described in any one of items 3A to 7A, which is an oxygen atom. Item 9A. The L １ However, -C(R Ｌ１ ) (Caution Ｌ２ ) - A pyrazole compound or salt thereof according to any one of items 3A to 7A. Item 10A. A pyrazole compound or salt thereof according to any one of items 3A to 7A, wherein the above p is 1 or 2. Item 11A. General formula (1-3):

[0031]

[0032] (In the formula, A Ｉ represents iodine. Z is a linking group, and the linking group represents a divalent carbon ring or a divalent heterocycle which may have substituents. X represents an oxygen atom. T represents an oxygen atom or a sulfur atom. R １ R represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted carbon ring, or an optionally substituted heterocycle. ２R represents a hydrogen atom, a halogen atom, an optionally substituted alkyl group, or an optionally substituted alkoxy group. ３ ) represents a hydrogen atom, an optionally substituted alkyl, an optionally substituted alkoxy, or an optionally substituted acyl. L represents an optionally substituted alkyl, an optionally substituted carbon ring, an optionally substituted heterocycle, an optionally substituted alkoxy, an oxy having an optionally substituted carbon ring, or an oxy having an optionally substituted heterocycle.) A pyrazole compound or a salt thereof represented by . Item 12A. A pesticide containing one or more selected from any one of the pyrazole compounds and salts thereof described in Items 1A to 11A as an active ingredient. Item 13A. A fungicide containing one or more selected from any one of the pyrazole compounds and salts thereof described in Items 1A to 11A as an active ingredient.

[0033] This disclosure can provide novel compounds or novel pesticides.

[0034] The pyrazole compounds, their structural isomers, or salts thereof disclosed herein (hereinafter sometimes referred to as "the compounds of this disclosure") are compounds represented by the following general formula (1), their structural isomers, or salts thereof.

[0035] The compounds in this disclosure may have various structural isomers, such as optical isomers, geometric isomers, and tautomers, but this disclosure includes both individual isomers and mixtures of isomers. More specifically, the compounds in this disclosure have two or more geometric isomers depending on the number of double bonds (carbon-carbon or carbon-nitrogen) in the structural formula. Therefore, this disclosure encompasses all conceivable geometric isomers and mixtures containing them in any proportion. Furthermore, the compounds in this disclosure also include various isomers other than those described above, within the scope of common technical knowledge in the art. Moreover, various isomers can be selectively synthesized using common technical knowledge and general experimental techniques in the art.

[0036]

[0037] In the formula, A represents iodine, optionally substituted alkynyl, substituted alkenyl, substituted cycloalkyl, formyl, or optionally substituted heterocyclic group. Z represents optionally substituted divalent carbocyclic group or optionally substituted divalent heterocyclic group. X represents an oxygen atom or carbonyl (C=O). T represents an oxygen atom or sulfur atom. L represents optionally substituted alkyl, optionally substituted carbocyclic, optionally substituted heterocyclic group, optionally substituted alkoxy, optionally substituted cycloalkoxy, optionally substituted aryloxy, or optionally substituted heteroaryloxy. １ R represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted carbon ring, or an optionally substituted heterocycle. ２ R represents a hydrogen atom, a halogen atom, an optionally substituted alkyl group, or an optionally substituted alkoxy group. ３ This represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted acyl group, an optionally substituted alkoxycarbonyl group, or an optionally substituted sulfonyl group.

[0038] Examples of pyrazole compounds represented by the general formula (1), their structural isomers, or salts thereof include, but are not limited to, the pyrazole compounds represented by the following general formula (1Y) or their salts.

[0039]

[0040] In the formula, Y １ Equation (A): -C(=T １ )N(R ３Ａ A base represented by )-, or formula (B):-C(-T ２ -R ３Ｂ This indicates a group represented by ) = N-. １ This represents an oxygen atom or a sulfur atom. ２ represents an oxygen atom or a sulfur atom. The A, Z, X, L, R １ , R ２, R ３Ａ , and R ３Ｂ This is the same as described above.

[0041] The pyrazole compounds represented by the general formula (1), their structural isomers, or salts thereof are preferably the pyrazole compounds represented by the following general formula (1-A) or their salts, the pyrazole compounds represented by the following general formula (1-B) or their salts, etc. Here, the pyrazole compounds represented by the general formula (1-A) or their salts can be rephrased as "pyrazolylamide compounds or their salts". The pyrazole compounds represented by the general formula (1-B) or their salts can be rephrased as "pyrazolyl imienoether compounds or their salts".

[0042]

[0043] In the formula, R ３Ａ R represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted acyl group, an optionally substituted alkoxycarbonyl group, or an optionally substituted sulfonyl group. ３Ｂ This represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted acyl group, an optionally substituted alkoxycarbonyl group, or an optionally substituted sulfonyl group. １ This represents an oxygen atom or a sulfur atom. ２ represents an oxygen atom or a sulfur atom. The A, Z, X, L, R １ , R ２ The same applies to the dashed lines as described above.

[0044] The pyrazole compound represented by the general formula (1), its structural isomer, or salts thereof are preferably the pyrazole compound represented by the following general formula (1A-A1) or its salt, the pyrazole compound represented by the following general formula (1A-B1) or its salt, the pyrazole compound represented by the following general formula (1B-A1) or its salt, the pyrazole compound represented by the following general formula (1B-B1) or its salt, etc.

[0045]

[0046] In the formula, R Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , and R Ａ５ These are the same or different hydrogen atoms, hydroxyl, formyl, nitro, cyano, halogen atoms, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted alkylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted amino, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted cycloalkylaminocarbonyl, optionally substituted aminocarbonyl, -C(=NOR ６ ) R ７ , represents a silyl which may have a substituent, a carbon ring which may have a substituent, or a heterocycle which may have a substituent. ６ R represents a hydrogen atom or an alkyl group which may have a substituent. ７ R represents an alkyl group which may have substituents. However, R Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , and R Ａ５ Of these, at least one represents an optionally substituted alkynyl, iodine, substituted alkenyl, substituted cycloalkyl, formyl, or optionally substituted heterocycle. １ , T ２ , L, R １ , R ２ , R ３Ａ , R ３Ｂ The same applies to the dashed lines as described above.

[0047] The compound represented by the general formula (1) or a salt thereof is preferably a pyrazole compound represented by the following general formula (1A-A2) or a salt thereof, a pyrazole compound represented by the following general formula (1A-B2) or a salt thereof, a pyrazole compound represented by the following general formula (1B-A2) or a salt thereof, or a pyrazole compound represented by the following general formula (1B-B2) or a salt thereof.

[0048]

[0049] In the ceremony, L １ is an oxygen atom, or -C(R) Ｌ１ ) (Caution Ｌ２ ) indicates the R Ｌ１ and R Ｌ２ R represents the same or different hydrogen atom or an alkyl group which may have a substituent. Ｌ１ and R Ｌ２ These two groups may bond to each other with adjacent carbon atoms to form a saturated or unsaturated carbon ring. The saturated or unsaturated carbon ring may further have substituents. ４ and R ５ R represents, either identically or differently, a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group, or an optionally substituted heterocycle. ４ and R ５ These two groups may bond to each other with adjacent carbon atoms to form a saturated or unsaturated carbon ring. The saturated or unsaturated carbon ring may further have substituents. p represents an integer from 0 to 3. When p is 2 or 3, the two or three R ４ These may be the same or different, and the two or three R's mentioned above are... ５ They may be the same or different. Ｂ１ , R Ｂ２ , R Ｂ３ , R Ｂ４ , and R Ｂ５These are the same or different hydrogen atoms, hydroxyl, formyl, nitro, cyano, halogen atoms, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted alkylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted amino, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted cycloalkylaminocarbonyl, optionally substituted aminocarbonyl, -C(=NOR ６ ) R ７ , represents a silyl which may have a substituent, a carbon ring which may have a substituent, or a heterocycle which may have a substituent. Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , R Ａ５ , T １ , T ２ , R １ , R ２ , R ３Ａ , R ３Ｂ , R ６ , R ７ The same applies to the dashed lines as described above.

[0050] The compound represented by the general formula (1) or a salt thereof is particularly preferably a pyrazole compound represented by the following general formula (1A-A3) or a salt thereof, a pyrazole compound represented by the following general formula (1A-B3) or a salt thereof, a pyrazole compound represented by the following general formula (1B-A3) or a salt thereof, or a pyrazole compound represented by the following general formula (1B-B3) or a salt thereof.

[0051]

[0052] In the formula, R ＣThis includes hydrogen atoms, hydroxyl, formyl, nitro, cyano, halogen atoms, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted alkylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted amino, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted cycloalkylaminocarbonyl, optionally substituted aminocarbonyl, -C(=NOR ６ ) R ７ , represents a silyl which may have a substituent, a carbon ring which may have a substituent, or a heterocycle which may have a substituent. Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , R Ａ５ , T １ , T ２ , L １ , R １ , R ２ , R ３Ａ , R ３Ｂ , R ４ , R ５ , R ６ , R ７ , p, R Ｂ１ , R Ｂ２ , R Ｂ４ , R Ｂ５ The same applies to the dashed lines as described above.

[0053] Preferably, L is a group represented by (L1), a group represented by (L2), a group represented by (L3), a group represented by (L4), a group represented by (L5), a group represented by (L6), a group represented by (L7), a group represented by (L8), and the like.

[0054]

[0055] The aforementioned R Ｂ１ , R Ｂ２ , R Ｂ３, R Ｂ４ , R Ｂ５ , R Ｌ１ , and R Ｌ２ This is the same as above. R ４Ａ , R ４Ｂ , R ４Ｃ , R ５Ａ , R ５Ｂ , and R ５Ｃ R represents, either identically or differently, a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group, or an optionally substituted heterocycle. ４Ａ , R ４Ｂ , R ４Ｃ , R ５Ａ , R ５Ｂ , and R ５Ｃ Two adjacent groups within may bond to each other with adjacent carbon atoms to form a saturated or unsaturated carbon ring. The saturated or unsaturated carbon ring may further have substituents. ２ This represents an oxygen atom.

[0056] More preferably, the compound represented by the general formula (1) or a salt thereof is a pyrazole compound represented by the following general formula (1A-L1) or a salt thereof, a pyrazole compound represented by the general formula (1A-L2) or a salt thereof, a pyrazole compound represented by the general formula (1A-L3) or a salt thereof, a pyrazole compound represented by the general formula (1A-L4) or a salt thereof, a pyrazole compound represented by the general formula (1A-L5) or a salt thereof, a pyrazole compound represented by the general formula (1A-L6) or a salt thereof, a pyrazole compound represented by the general formula (1A-L7) or a salt thereof, or a compound represented by the general formula (1A-L8) These include pyrazole compounds or salts thereof, pyrazole compounds or salts represented by the following general formula (1B-L1), pyrazole compounds or salts represented by the general formula (1B-L2), pyrazole compounds or salts represented by the general formula (1B-L3), pyrazole compounds or salts represented by the general formula (1B-L4), pyrazole compounds or salts represented by the general formula (1B-L5), pyrazole compounds or salts represented by the general formula (1B-L6), pyrazole compounds or salts represented by the general formula (1B-L7), pyrazole compounds or salts represented by the general formula (1B-L8), etc.

[0057]

[0058]

[0059]

[0060]

[0061] Here, R in the equation Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , R Ａ５ X, T １ , T ２ , R １ , R ２ , R ３Ａ , R ３Ｂ , L ２ , R Ｂ１ , R Ｂ２ , R Ｂ３ , R Ｂ４ , R Ｂ５ , R Ｌ１ , R Ｌ２ , R４Ａ , R ４Ｂ , R ４Ｃ , R ５Ａ , R ５Ｂ , R ５Ｃ The same applies to the dashed lines as described above.

[0062] The aforementioned R １ Preferably, the alkyl group may have substituents, and more preferably, a tertiary alkyl group (e.g., t-butyl).

[0063] The aforementioned R ２ Preferably, it is a hydrogen atom or an alkyl group which may have substituents, and more preferably a hydrogen atom.

[0064] The aforementioned R ３ , R ３Ａ , and R ３Ｂ Preferably, these include hydrogen atoms, optionally substituted acyls, optionally substituted alkoxycarbonyls, optionally substituted alkyls, optionally substituted alkenyls, optionally substituted alkylthioalkyls, optionally substituted alkylsulfonylalkyls, and the like.

[0065] The aforementioned X is preferably an oxygen atom or a carbonyl atom.

[0066] Said T, T １ , and, T ２ Preferably, each of these is an oxygen atom.

[0067] The aforementioned R Ｌ１ Preferably, R is a hydrogen atom. Ｌ２ Preferably, L is a hydrogen atom. ２ Preferably, it is an oxygen atom.

[0068] The aforementioned p is preferably 1 or 2.

[0069] R Ａ２The substituents are optionally substituted alkynyls, substituted alkenyls, substituted cycloalkyls, formyls, or optionally substituted heterocycles, more preferably substituted alkenyls or optionally substituted alkynyls, even more preferably optionally substituted alkynyls of group 1, optionally substituted alkenyls of group 1, or optionally substituted cycloalkyls of group 3, and particularly preferably optionally substituted alkynyls of group 1, or optionally substituted alkenyls of group 1. Specifically, R Ａ２ These include alkynyls represented by the following general formula (M1), substituted alkenyls represented by the general formula (M2), substituted cycloalkyls represented by the general formula (M3), formyls represented by the general formula (M4), or heterocycles represented by the general formula (M5).

[0070]

[0071] In the formula, R １２ This represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkoxy group, an optionally substituted carbon ring, an optionally substituted heterocycle, or an optionally substituted silyl group. Preferably, (M1) is an unsubstituted alkynyl; a C3-6 alkynyl having a hydroxyl group; a C3-6 alkynyl having a C3-15 cycloalkyl group; a C3-6 alkynyl having a C1-6 alkoxy group; a C3-6 alkynyl having an optionally substituted phenyl group; an alkynyl having a tri(C1-6 alkyl)silyl, etc. １６ , R １７ , and R １８ These are the same or different hydroxy, formyl, nitro, cyano, halogen atoms, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted alkylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted amino, optionally substituted acyl, -OR ｃ ,-NHC(O)R ｄ , -NRｅ C(O)R ｆ - NHSO ２ R ｇ -C≡CR ｈ , -SO ２ NH ２ , -C(=NOR ｉ ) R ｊ , represents a carbon ring which may have substituents, or a heterocycle which may have substituents. １６ , R １７ , and R １８ Of these, at least one is preferably an alkoxycarbonyl which may have substituents. Preferably, (M2) is a C2-6 alkenyl having a C1-6 alkoxycarbonyl which may have substituents. １９ , R ２０ , R ２１ , R ２２ , and R ２３ These are the same or different hydroxy, formyl, nitro, cyano, halogen atoms, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted alkylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted amino, optionally substituted acyl, -OR ｃ ,-NHC(O)R ｄ , -NR ｅ C(O)R ｆ - NHSO ２ R ｇ -C≡CR ｈ , -SO ２ NH ２ , -C(=NOR ｉ ) R ｊ , represents a carbon ring or heterocycle which may have substituents. Preferably, (M3) is a C3-15 cycloalkyl group having at least one substituent selected from the group consisting of cyano and heterocycles which may have substituents. Hy represents a heterocycle which may have substituents. Preferably, (M5) is an epoxy which may have substituents.

[0072] RＡ１ Preferably, it is a hydrogen atom, a halogen atom, or an alkyl group which may have a substituent, and more preferably a hydrogen atom. Ａ３ Preferably, it is a hydrogen atom, a halogen atom, or an alkyl group which may have a substituent, and more preferably a hydrogen atom. Ａ４ Preferably, it is a hydrogen atom, a halogen atom, or an alkyl group which may have a substituent, and more preferably a hydrogen atom. Ａ５ Preferably, it is a hydrogen atom, a halogen atom, or an alkyl group which may have substituents, and more preferably a hydrogen atom.

[0073] R Ｂ１ Preferably, it is a hydrogen atom, a halogen atom, or an alkyl group which may have a substituent, and more preferably a hydrogen atom. Ｂ２ Preferably, it is a hydrogen atom, a halogen atom, or an alkyl group which may have a substituent, and more preferably a hydrogen atom. Ｂ３ Preferably, it is a hydrogen atom, a halogen atom, or an alkyl group which may have a substituent, and more preferably a hydrogen atom. Ｂ４ Preferably, it is a hydrogen atom, a halogen atom, or an alkyl group which may have a substituent, and more preferably a hydrogen atom. Ｂ５ Preferably, it is a hydrogen atom, a halogen atom, or an alkyl group which may have substituents, and more preferably a hydrogen atom.

[0074] Preferably, R ４Ａ , R ４Ｂ , R ４Ｃ , R ５Ａ , R ５Ｂ , and R ５Ｃ One or more of these are halogen atoms or alkyl groups which may have substituents, more preferably fluorine atoms, chlorine atoms, C1-6 alkyl groups, etc.

[0075] The following are definitions of terms used in this specification.

[0076] The notation Cx to y can be rephrased as Cx to Cy, or carbon number x to y. The notation Cx to Cy indicates that it has x to y carbon atoms. Here, x and y represent integers, and it is understood that all integers between x and y are also disclosed individually. For example, C1 to 15 have 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 carbon atoms; C1 to 6 have 1, 2, 3, 4, 5, or 6 carbon atoms; C1 to 3 have 1, 2, or 3 carbon atoms; and C2 to 15 have 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 carbon atoms. C1-6 refers to a ring with 1, 2, 3, 4, 5, or 6 carbon atoms, C2-3 refers to a ring with 2 or 3 carbon atoms, 3-15 membered (C3-15 ring) refers to a cyclic compound with 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 members, and 3-7 membered (C3-7 ring) refers to a cyclic compound with 3, 4, 5, 6, or 7 members.

[0077] "May have substituents" means either substituted or unsubstituted. When this term is used and the number of substituents is not explicitly stated, it means there is one or more substituents, i.e., one or two or more. "Substitutable" means having substituents. "Unsubstituted" means not having substituents.

[0078] There are no particular limitations on the halogen atoms; for example, fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, etc.

[0079] The carbon chains such as "alkyl," "alkenyl," "alkynyl," and "alkoxy" may be straight or branched.

[0080] There are no particular limitations on the alkyl group, and examples include C1-6 alkyl groups. Specifically, examples of C1-6 alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, pentyl, isopentyl, 1-methylbutyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl, 1-isopropylpropyl, 1,1,2-trimethylpropyl, and 1,2,2-trimethylpropyl.

[0081] There are no particular limitations on the alkenyls; for example, C2-6 alkenyls can be used. Specifically, C2-6 alkenyls represent unsaturated hydrocarbon groups having one or more double bonds and being linear or branched. Furthermore, if geometric isomers exist, they may be either the E-form or the Z-form, or a mixture of the E-form and Z-form in any proportion, and are not particularly limited as long as they fall within the specified range of carbon. There are no particular limitations on the C2-6 alkenyls, but specifically, examples include vinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 3-methyl-2-butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 4-methyl-3-pentenyl, 3-methyl-2-pentenyl, 1-methylvinyl, 2-methylvinyl, 1,2-dimethylvinyl, 2,2-dimethylvinyl, and 1,2,2-trimethylvinyl. Examples of C2-6 alkenyls having substituents include 1-phenylvinyl and 2-phenylvinyl.

[0082] There are no particular limitations on the alkynyl group, and examples include C2-6 alkynyls. A C2-6 alkynyl group represents an unsaturated hydrocarbon group having one or more triple bonds and being linear or branched. There are no particular limitations on the C2-6 alkynyl group, and specific examples include ethynyl, 1-propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1,1-dimethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, and 5-hexynyl.

[0083] There are no particular limitations on the alkoxy; for example, C1-6 alkoxys can be used. C1-6 alkoxys refer to a combination of the aforementioned C1-15 alkyl groups bonded via an oxygen atom. There are no particular limitations on the C1-6 alkoxys, but specifically, examples include methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutoxy, sec-butoxy, t-butoxy, pentyloxy, isopentyloxy, 1-methylbutoxy, 2-methylbutoxy, neopentyloxy, 1-ethylpropyloxy, 1,2-dimethylpropyloxy, hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutoxy, 2,2-dimethylbutoxy, 3,3-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,3-dimethylbutoxy, 2-ethylbutoxy, 1-isopropylpropyloxy, 1,1,2-trimethylpropyloxy, 1,2,2-trimethylpropyloxy, and the like.

[0084] There are no particular limitations on the carbon ring; for example, saturated carbon rings (cycloalkyl) with 3 to 15 members or unsaturated carbon rings with 3 to 15 members can be used.

[0085] The 3-15 member saturated or unsaturated carbon rings are not particularly limited, and examples include 3-15 member cycloalkyls, 3-15 member cycloalkenyls, C6-14 aryls, etc.

[0086] There are no particular limitations on the C3-15 cycloalkyl group, and examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclododecyl, and adamantyl. The C3-15 cycloalkyl group may be substituted with an oxo group. Examples of C3-15 cycloalkyl groups substituted with an oxo group include cyclopentan-3-one and cyclohexane-3-one.

[0087] There are no particular limitations on the C3-15 cycloalkenyl, and examples include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, and cyclooctenyl. There are no particular limitations on the position of the double bond in the C3-15 cycloalkenyl.

[0088] There are no particular limitations on the C6-14 aryl group; examples include phenyl, naphthyl, anthracenyl, indenyl, acenaphthinyl, acenaphthenyl, fluorenyl, phenantrenyl, and azlenyl. The term "aryl" can be rephrased as an aromatic hydrocarbon group. Examples of substituted C6-14 aryl groups include tolyl, xylyl, mesityl, and biphenyl.

[0089] An oxy compound having a carbocyclic ring refers to a compound in which the above-mentioned carbocyclic ring is bonded via an oxygen atom. There are no particular limitations on oxy compounds having a carbocyclic ring; examples include 3-15 membered cycloalkyl oxy compounds, 3-15 membered cycloalkenyl oxy compounds, C6-14 aryl oxy compounds, etc. Specifically, examples include cyclopropyl oxy compounds, cyclobutyl oxy compounds, cyclopentyl oxy compounds, cyclohexyl oxy compounds, cyclopropenyl oxy compounds, cyclobutenyl oxy compounds, cyclopentenyl oxy compounds, cyclohexenyl oxy compounds, phenyl oxy compounds, naphthyl oxy compounds, etc.

[0090] There are no particular limitations on the heterocycle; for example, saturated or unsaturated heterocycles can be included. Examples of saturated or unsaturated heterocycles include 5-7 member saturated or unsaturated heterocycles having 1-6 atoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms.

[0091] There are no particular limitations on saturated heterocycles; they include not only saturated heterocycles but also non-aromatic heterocycles. Examples of saturated heterocycles include monocyclic saturated heterocycles with 4 to 6 members, or fused saturated heterocycles formed by the fusion of such monocyclic saturated heterocycles with a benzene ring or a monocyclic aromatic ring. The ring constituent atoms of the saturated heterocycle may be substituted with oxo groups.

[0092] There are no particular limitations on monocyclic saturated heterocycles or monocyclic non-aromatic heterocycles. Specifically, for example, oxetanyl, thienyl (thiophene), azetidinyl, pyrrolidinyl, pyrrolidinyl-2-one, piberidinyl, morpholinyl, thiomorpholinyl, piperazinyl, hexamethyleneiminyl, oxazolidinyl, thiazolidinyl, imidazolidinyl, oxazolinyl, thiazolinyl, isoxazolinyl, imidazolinyl, dioxolyl, dioxolanil, dihydrooxadiazolyl, 2-oxopyrrolidine-1-yl, 2,4-dioxopyrimidine-5-yl, 2-oxo-1 Examples include 3-oxazolidine-5-yl, 5-oxo-1,2,4-oxadiazolin-3-yl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-dioxepane-2-yl, pyranil, tetrahydropyranil, thiopyranil, tetrahydrothiopyranil, 1-oxidetetrahydrothiopyranil, 1,1-dioxidetetrahydrothiopyranil, tetrahydrofuranil, dioxanil, pyrazolidinil, pyrazolinil, tetrahydropyrimidinil, dihydrotriazolyl, tetrahydrotriazolyl, succinimidyl, pyrrolidonil, etc.

[0093] There are no particular limitations on the condensed saturated heterocycle or monocyclic non-aromatic saturated heterocycle, and specific examples include dihydroindolyl, dihydroisoindolyl, dihydrobenzofuranyl, dihydrobenzodioxynyl, dihydrobenzodioxepinyl, tetrahydrobenzofuranyl, clomenyl, dihydroquinolinyl, tetrahydroquinolinyl, dihydroisoquinolinyl, tetrahydroisoquinolinyl, dihydrophthalazinyl, 1,3-benzooxol, and the like.

[0094] There are no particular limitations on the unsaturated heterocycles, and examples include five- or six-membered monocyclic aromatic heterocycles containing one to six heteroatoms selected from oxygen, sulfur, and nitrogen atoms in addition to carbon atoms as ring constituent atoms; aromatic heterocycles (heteroaryls) such as aromatic fused heterocycles formed by the fusion of the monocyclic aromatic heterocycle with a benzene ring or a monocyclic aromatic ring. The ring constituent atoms of saturated or unsaturated heterocycles may be substituted with oxo groups.

[0095] There are no particular limitations on the aromatic monocyclic heterocycles, but specifically, examples include furyl, thienyl, pyridyl, 2-oxopyridyl, pyrimidinyl, pyridadinyl, pyrazinyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl (e.g., 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl), thiadiazolyl (e.g., 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl), triazolyl (e.g., 1,2,4-triazolyl), tetrazolyl, triazinyl (e.g., 1,3,5-triazinyl, 1,2,4-triazinyl), etc.There are no particular limitations on the aromatic condensed heterocycles, but specifically, for example, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, synnolinyl, phthalazinyl, naphthilidinyl, benzofuranyl, benzochenyl, benzoxazolyl, benzoisoxazolyl, benzothiazolyl, benzoisothiazolyl, benzimidazolyl, benzotriazolyl, indolyl, isoindolyl, indazolyl, phlopyridyl, chenol Pyridyl, pyrrolopyridyl (e.g., pyrrolopyridyl [1,2-a]pyridyl, pyrrolopyridyl [2,3-b]pyridyl, etc.), oxazolopyridyl (e.g., oxazolo[3,2-a]pyridyl, oxazolo[5,4-b]pyridyl, oxazolo[4,5-b]pyridyl, etc.), isoxazolopyridyl (e.g., isoxazolo[2,3-a]pyridyl, isoxazolo[4,5-b]pyridyl, isoxazolo[5,4-b]pyridyl, etc.), Thiazolopyridyls (e.g., thiazolo[3,2-a]pyridyl, thiazolo[5,4-b]pyridyl, thiazolo[4,5-b]pyridyl, etc.), isothiazolopyridyls (e.g., isothiazolo[2,3-a]pyridyl, isothiazolo[4,5-b]pyridyl, isothiazolo[5,4-b]pyridyl), imidazopyridyls (e.g., imidazo[1,2-a]pyridyl, imidazo[4,5-b]pyridyl, etc.), pyrazolopyridyls (e.g., Examples include pyrazolo[1,4-a]pyridyl, pyrazolo[3,4-a]pyridyl, pyrazolo[4,3-a]pyridyl, etc.), indolidinyl, triazolopyridyl (e.g., [1,2,4-]triazolo[1,5-a]pyridyl), triazolopyrimidinyl, pyrrolopyrimidinyl, pyrrolopyrazinyl, imidazopyrimidinyl, imidazopyrazinyl, pyrazolopyrimidinyl, pyrazolotenyl, pyrazolotriazinyl, etc.).

[0096] An oxy compound having a heterocycle refers to a saturated or unsaturated heterocycle bonded via an oxygen atom. There are no particular limitations on oxy compounds having an unsaturated heterocycle (or heteroaryl oxy compounds), and specific examples include pyridyloxy, pyridadinyloxy, pyrimidinyloxy, pyrazinyloxy, triazinyloxy, tetradinyloxy, thienyloxy, thiazolyloxy, isothiazolyloxy, thiadiazolyloxy, furyloxy, pyrrolyloxy, imidazolyloxy, pyrazolyloxy, oxazolyloxy, isoxazolyloxy, triazolyloxy, oxadiazolyloxy, thiadiazolyloxy, tetrazolyloxy, and the like.

[0097] Examples of linking groups, where the linking group may have substituents, include arylenes. Here, arylene refers to a divalent group derived by removing one arbitrary hydrogen atom from the aryl group. Arylenes may be monocyclic or fused rings. The number of atoms constituting the ring is not particularly limited, but arylenes with 6 to 22 carbon atoms are preferred, arylenes with 6 to 18 carbon atoms are more preferred, and arylenes with 6 to 10 carbon atoms are even more preferred. Specific examples of arylenes include phenylene groups, naphthalene diyl groups, anthracenediyl groups, phenanthrene diyl groups, and fluoranthyl groups.

[0098] Examples of linking groups, where the linking group may have substituents, include heterocyclic rings or divalent heterocyclic groups that may have substituents, such as saturated or unsaturated heterocyclic rings and heteroarylenes. Here, heteroarylene refers to a divalent group derived by removing one arbitrary hydrogen atom from the heteroaryl ring. Heteroarylenes may be monocyclic or fused rings. The number of atoms constituting the ring is not particularly limited, but is preferably 5 to 10 (5-membered to 10-membered heteroarylenes). Specific examples of heteroarylenes include pyrrolediyl, imidazolediyl, pyrazolediyl, pyridinediyl, pyridazinediyl, pyrimidinediyl, pyrazinediyl, triazolediyl, triazinediyl, isoxazolediyl, oxazolediyl, oxadiazolediyl, isothiazolediyl, thiazolediyl, thiadiazolediyl, frangil, thiophenediyl, and the like.

[0099] There are no particular limitations on the acyl, and examples include C1-6 alkylcarbonyls and carbonyls having a saturated or unsaturated carbocyclic ring with 3-15 members.

[0100] C1-6 alkylcarbonyl refers to a compound in which the aforementioned C1-6 alkyl groups are linked via a carbonyl group. There are no particular limitations on C1-6 alkylcarbonyls, but specific examples include methylcarbonyl, ethylcarbonyl, propylcarbonyl, isopropylcarbonyl, butylcarbonyl, isobutylcarbonyl, sec-butylcarbonyl, t-butylcarbonyl, pentylcarbonyl, isopentylcarbonyl, and the like.

[0101] A carbonyl having a 3- to 15-membered saturated or unsaturated carbon ring refers to a carbonyl molecule in which the aforementioned 3- to 15-membered saturated or unsaturated carbon rings are linked via a carbonyl molecule. There are no particular limitations on the carbonyl having a 3- to 15-membered saturated or unsaturated carbon ring; specifically, examples include cyclopropyl carbonyl, cyclohexyl carbonyl, cyclopropenyl carbonyl, cyclohexenyl carbonyl, and phenylcarbonyl (benzoyl).

[0102] C1-6 alkoxycarbonyls refer to compounds in which the aforementioned C1-6 alkoxys are linked via carbonyl groups. There are no particular limitations on C1-6 alkoxycarbonyls, but specific examples include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, t-butoxycarbonyl, pentyloxycarbonyl, isopentyloxycarbonyl, and the like.

[0103] An oxycarbonyl having a 3-15 member saturated or unsaturated carbon ring refers to a molecule in which the aforementioned 3-15 member saturated or unsaturated carbon rings are linked via an oxycarbonyl. There are no particular limitations on the oxycarbonyl having a 3-15 member saturated or unsaturated carbon ring; specifically, examples include oxycarbonyl having a saturated carbon ring such as cyclopropyloxycarbonyl and cyclohexyloxycarbonyl; and oxycarbonyl having an unsaturated carbon ring such as cyclopropenyloxycarbonyl, cyclohexenyloxycarbonyl, and phenoxycarbonyl.

[0104] Examples of aminocarbonyls include R ７０ R ７１ Examples include NCO groups. Here, in the formula, R ７０ and R ７１ These represent, either identically or differently, a hydrogen atom, a C1-6 alkyl group which may have substituents, a C3-15 cycloalkyl group which may have substituents, a C2-6 alkenyl group which may have substituents, or a C2-6 alkynyl group which may have substituents.

[0105] Examples of alkylaminocarbonyls include R ７０ R ７１ Examples include NCO groups. Here, in the formula, R ７０ and R ７１ This represents a C1-6 alkyl group which may have a hydrogen atom or substituent, and which may be the same or different.

[0106] Examples of cycloalkylaminocarbonyls include R ７０ R ７１Examples include NCO groups. Here, in the formula, R ７０ and R ７１ These represent, either identically or differently, a hydrogen atom, a C1-6 alkyl group which may have substituents, or a C3-15 cycloalkyl group which may have substituents.

[0107] For example, R ７２ R ７３ Examples include N groups. Here, in the formula, R ７２ and R ７３ These represent, either identically or differently, a hydrogen atom, a C1-6 alkyl group which may have substituents, a C2-6 alkenyl group which may have substituents, or a C2-6 alkynyl group which may have substituents.

[0108] C1-6 alkylthio refers to a compound in which the aforementioned C1-6 alkyl groups are linked via a thio group (sulfide). There are no particular limitations on the C1-6 alkylthio, and examples include methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, sec-butylthio, t-butylthio, pentylthio, isopentylthio, etc.

[0109] A thio group having a 3- to 15-membered saturated or unsaturated carbon ring refers to a thio group in which the aforementioned 3- to 15-membered saturated or unsaturated carbon rings are bonded via a thio group. There are no particular limitations on the thio group having a 3- to 15-membered saturated or unsaturated carbon ring; specifically, examples include cyclopropylthio, cyclohexyloxythio, cyclopropenylthio, and phenylthio.

[0110] C1-6 alkylsulfinyl refers to a compound in which the aforementioned C1-15 alkyl groups are linked via a sulfinyl (sulfoxide) group. There are no particular limitations on the C1-15 alkylsulfinyl, and examples include methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, t-butylsulfinyl, pentylsulfinyl, isopentylsulfinyl, and the like.

[0111] A sulfinyl having a 3- to 15-membered saturated or unsaturated carbon ring refers to a molecule in which the aforementioned 3- to 15-membered saturated or unsaturated carbon rings are bonded via a sulfinyl molecule. There are no particular limitations on the sulfinyl having a 3- to 15-membered saturated or unsaturated carbon ring; specifically, examples include cyclopropylsulfinyl, cyclohexyloxysulfinyl, cyclopropenylsulfinyl, and phenylsulfinyl.

[0112] C1-C6 alkylsulfonyl refers to a compound in which the aforementioned C1-15 alkyl groups are bonded via a sulfonyl group. There are no particular limitations on C1-6 alkylsulfonyl, and examples include methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, t-butylsulfonyl, pentylsulfonyl, isopentylsulfonyl, and the like.

[0113] A sulfonyl having a 3- to 15-membered saturated or unsaturated carbon ring refers to a sulfonyl compound in which the aforementioned 3- to 15-membered saturated or unsaturated carbon rings are bonded via a sulfonyl group. There are no particular limitations on the sulfonyl having a 3- to 15-membered saturated or unsaturated carbon ring; specifically, examples include cyclopropylsulfonyl, cyclohexyloxysulfonyl, cyclopropenylsulfonyl, and phenylsulfonyl.

[0114] Examples of silyls that may have substituents include R ８０ R ８１ R ８２ Examples include Si groups. ８０ R ８１ R ８２ There are no particular limitations on the Si group, and examples include trimethylsilyl (TMS), triethylsilyl (TES), triisopropylsilyl (TIPS), t-butyldimethylsilyl (TBS), t-butyldiphenylsilyl (TBDPS), triphenylsilyl, dimethylphenylsilyl, diethylphenylsilyl, methyldiphenylsilyl, and ethyldiphenylsilyl.

[0115] L １ However, -C(R Ｌ１ ) (CautionＬ２ ) - If the above R Ｌ１ and R Ｌ２ These two groups may bond to each other with adjacent carbon atoms to form a saturated or unsaturated carbon ring. The saturated or unsaturated carbon ring may further have substituents. Ｌ１ and R Ｌ２ Examples include 3- to 15-membered saturated or unsaturated carbon rings, where each member is bonded to an adjacent carbon atom to form a saturated or unsaturated carbon ring, and which may have substituents.

[0116] The substituents in this disclosure are not particularly limited and include, for example, one or more substituents selected from Group 1, one or more substituents selected from Group 2, one or more substituents selected from Group 3, one or more substituents selected from Group 4, one or more substituents selected from Group 5, one or more substituents selected from Group 6, and so on.

[0117] Specifically, the alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, or alkoxy compounds may have one or more substituents selected from the following <Group 1>, and if they have two or more substituents, the substituents may be the same or different.

[0118] <Group 1>: Halogen atom; hydroxyl group; optionally substituted C3-6 cycloalkyl; optionally substituted C1-6 alkoxy; optionally substituted (C1-6 alkyl) carbonyl; carboxyl; optionally substituted (C1-6 alkoxy) carbonyl; optionally substituted carbocyclic (e.g., phenyl); optionally substituted heterocyclic (e.g., pyridyl); optionally substituted phenylcarbonyl; optionally substituted C1-6 alkylthio; optionally substituted phenylthio; optionally substituted C1-6 alkylsulfonyl; optionally substituted phenylsulfonyl; R ８０ R ８１ R ８２Si group, cyano; nitro; formyl; oxy having a 3-15 member saturated or unsaturated carbon ring, which may have substituents; C1-6 alkylsulfinyl, which may have substituents; phenylsulfinyl, which may have substituents; R ７０ R ７１ NCO group; and; R ７２ R ７３ N group. Note that the alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, or alkoxy of Group 1 may be substituted with one or more halogens, and if substituted with two or more halogens, the halogens may be the same or different. An alkyl substituted with a halogen atom is called a haloalkyl. An alkenyl substituted with a halogen atom is called a haloalkenyl. An alkoxy substituted with a halogen atom is called a haloalkoxy. A cycloalkyl substituted with a halogen atom is called a halocycloalkyl. A cycloalkenyl substituted with a halogen atom is called a halocycloalkenyl. An alkoxy substituted with a halogen atom is called a haloalkoxy.

[0119] Furthermore, as the one or more substituents selected from the above-mentioned <Group 1>, one or more substituents selected from the following <Group 2> are preferred.

[0120] <Group 2>: Halogen atom; hydroxyl group; C3-6 cycloalkyl which may have at least one substituent selected from the group consisting of halogen atom, C1-6 alkyl, C2-6 alkenyl and C1-6 alkoxy and (C1-6 alkoxy)carbonyl; C1-6 alkoxy which may have at least one substituent selected from the group consisting of halogen atom, C1-6 alkyl, C2-6 alkenyl, C1-6 alkoxy and (C1-6 alkoxy)carbonyl; halogen atom, C1-6 alkyl, C2-6 alkenyl and C1-6 alkoxy and (C (C1-6 alkyl) carbonyl; carboxyl; (C1-6 alkoxy) carbonyl; (C1-6 alkoxy) carbonyl; (C1-6 alkoxy) carbonyl; halogen atom, C1-6 alkyl, C2-6 alkenyl, C1-6 alkoxy and (C1-6 alkoxy) carbonyl; at least one selected from the group consisting of halogen atom, C1-6 alkyl, C2-6 alkenyl, C1-6 alkoxy and (C1-6 alkoxy) carbonyl Phenyl which may have substituents; naphthyl which may have at least one substituent selected from the group consisting of halogen atoms, C1-6 alkyl, C2-6 alkenyl, C1-6 alkoxy and (C1-6 alkoxy)carbonyl; phenylcarbonyl which may have at least one substituent selected from the group consisting of halogen atoms, C1-6 alkyl, C2-6 alkenyl, C1-6 alkoxy and (C1-6 alkoxy)carbonyl; halogen atoms, C1-6 alkyl, C2-6 alkenyl, C1-6 alkoxy and (C1- C1-6 alkylthios which may have at least one substituent selected from the group consisting of 6-alkoxy)carbonyl; phenylthios which may have at least one substituent selected from the group consisting of halogen atoms, C1-6 alkyl, C2-6 alkenyl, C1-6 alkoxy and (C1-6 alkoxy)carbonyl; C1-6 alkylsulfonyls which may have at least one substituent selected from the group consisting of halogen atoms, C1-6 alkyl, C2-6 alkenyl, C1-6 alkoxy and (C1-6 alkoxy)carbonyl;Phenylsulfonyl may have at least one substituent selected from the group consisting of a halogen atom, C1-6 alkyl, C2-6 alkenyl, C1-6 alkoxy, and (C1-6 alkoxy)carbonyl; and a tri(C1-6 alkyl)silyl group.

[0121] The above saturated or unsaturated carbon rings (sometimes referred to as carbon rings) and heterocycles may have one or more substituents selected from the following group 3, and if they have two or more substituents, the substituents may be the same or different.

[0122] <Group 3>: Halogen atom; hydroxyl group; cyano; nitro; formyl; oxo group; carboxyl; C1-6 alkyl; C1-6 alkoxy; phenoxy; C1-6 alkoxy having a C3-6 unsaturated carbon ring; (C1-6 alkoxy)C1-6 alkyl; C2-6 alkenyl; C2-6 alkynyl; C3-6 cycloalkyl; C1-6 alkylthio; C1-6 alkylthio having a C3-6 unsaturated carbon ring; C1-6 alkylsulfinyl; C1-6 alkylsulfonyl; C1-6 alkylamino; di(C1-6 alkyl) Mino; (C1-6 alkyl)carbonyl; carbonyl having a C3-6 unsaturated carbon ring; (C1-6 alkoxy)carbonyl; oxycarbonyl having a C3-6 unsaturated carbon ring; (C1-6 alkyl)aminocarbonyl; di(C1-6 alkyl)aminocarbonyl; phenyl which may have at least one substituent selected from the group consisting of a halogen atom, C1-6 alkyl, C2-6 alkenyl, C1-6 alkoxy and (C1-6 alkoxy)carbonyl; and tri(C1-6 alkyl)silyl.

[0123] Furthermore, the alkyl, alkenyl, alkynyl, cycloalkyl, or alkoxy in Group 3 may be substituted with one or more halogens, and if substituted with two or more halogens, the halogens may be the same or different.

[0124] Furthermore, as the one or more substituents selected from the above-mentioned <Group 3>, one or more substituents selected from the following <Group 4> are preferred.

[0125] <Group 4>: Halogen atoms; nitro; oxo group; carboxyl; C1-6 alkyl; C1-6 alkoxy; phenoxy; (C1-6 alkoxy)C1-6 alkyl; di(C1-6 alkyl)amino; (C1-6 alkyl)carbonyl; carbonyl having a C3-6 unsaturated carbon ring; (C1-6 alkoxy)carbonyl; oxycarbonyl having a C3-6 unsaturated carbon ring; and; phenyl which may have at least one substituent selected from the group consisting of halogen atoms, C1-6 alkyl, C2-6 alkenyl, C1-6 alkoxy and (C1-6 alkoxy)carbonyl.

[0126] The above amino group may have one or more substituents selected from the following group 5, and if it has two or more substituents, the substituents may be the same or different.

[0127] <Group 5>: C1-6 alkyl; (C1-6 alkoxy)C1-6 alkyl; C2-6 alkenyl; C2-6 alkynyl; C3-6 cycloalkyl; (C1-6 alkyl) carbonyl; (C3-6 cycloalkyl) carbonyl; and (C1-6 alkoxy) carbonyl.

[0128] Furthermore, the alkyl, alkenyl, alkynyl, cycloalkyl, or alkoxy in Group 5 may be substituted with one or more halogen atoms, and if substituted with two or more halogen atoms, the halogen atoms may be the same or different.

[0129] The above silyl may have one or more substituents selected from the following group 6, and if it has two or more substituents, the substituents may be the same or different.

[0130] Group 6: C1-6 alkyl; C2-6 alkenyl; C2-6 alkynyl; C3-6 cycloalkyl; and; phenyl which may have one or more C1-6 alkyl groups.

[0131] Furthermore, the alkyl, alkenyl, alkynyl, cycloalkyl, or alkynyl in Group 6 may be substituted with one or more halogen atoms, and if substituted with two or more halogen atoms, the halogen atoms may be the same or different.

[0132] A C1-6 haloalkyl refers to a C1-6 alkyl group in which one or more hydrogen atoms are arbitrarily substituted with one or more halogen atoms. When substituted with two or more halogen atoms, these halogen atoms may be the same or different, and there is no particular limit to the number of substitutions as long as they can exist as substituents. There are no particular limitations on the C1-6 haloalkyls, and examples include monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, monobromomethyl, monoiodomethyl, chlorodifluoromethyl, bromodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 2,2,2-trichloroethyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, heptafluoroisopropyl, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl, nonafluorobutyl, nonafluoro-sec-butyl, 3,3,4,4,5,5,5-heptafluoropentyl, undecafluoropentyl, tridecafluorohexyl, and the like.

[0133] A haloalkenyl refers to a C2-C6 alkenyl in which one or more halogen atoms are arbitrarily substituted with one or more halogen atoms. When substituted with two or more halogen atoms, these halogen atoms may be the same or different, and there is no particular limit to the number of substitutions as long as they can exist as substituents. There are no particular limitations on C2-C6 haloalkenyls, and specific examples include 2-fluorovinyl, 2,2-difluorovinyl, 2,2-dichlorovinyl, 3-fluoroallyl, 3,3-difluoroallyl, 3,3-dichloroallyl, 4,4-difluoro-3-butenyl, 5,5-difluoro-4-pentenyl, 6,6-difluoro-5-hexenyl, and the like.

[0134] A C2-6 haloalkynyl refers to a C2-6 alkynyl in which one or more halogen atoms are arbitrarily substituted with one or more halogen atoms. When two or more halogen atoms are substituted, these halogen atoms may be the same or different, and there is no particular limit to the number of substitutions as long as they can exist as substituents. There are no particular limitations on the C2-6 haloalkynyls, for example, 2-fluoroethynyl, 2-chloroethynyl, 2-bromoethynyl, 2-iodoethynyl, 3,3-difluoro-1-propynyl, 3-chloro-3,3-difluoro-1-propynyl, 3-bromo-3,3-difluoro-1-propynyl, 3,3,3-trifluoro-1-propynyl, 4,4-difluoro-1-butynyl, 4,4-difluoro-2-butynyl, 4-chloro-4,4-difluoro-1-butynyl, 4-chloro-4,4-difluoro-2-butynyl, 4-bromo-4,4-difluoro Examples include -1-butynyl, 4-bromo-4,4-difluoro-2-butynyl, 4,4,4-trifluoro-1-butynyl, 4,4,4-trifluoro-2-butynyl, 5,5-difluoro-3-pentynyl, 5-chloro-5,5-difluoro-3-pentynyl, 5-bromo-5,5-difluoro-3-pentynyl, 5,5,5-trifluoro-3-pentynyl, 6,6-difluoro-4-hexynyl, 6-chloro-6,6-difluoro-4-hexynyl, 6-bromo-6,6-difluoro-4-hexynyl, and 6,6,6-trifluoro-4-hexynyl.

[0135] A C1-6 haloalkoxy refers to a C1-C6 alkoxy in which one or more hydrogen atoms are arbitrarily substituted with one or more halogen atoms. When substituted with two or more halogen atoms, these halogen atoms may be the same or different, and there is no particular limit to the number of substitutions as long as they can exist as substituents. There are no particular limitations on the C1-6 haloalkoxys, but specifically, examples include difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, pentafluoroethoxy, 2,2,2-trichloroethoxy, 3,3-difluoropropyloxy, 3,3,3-trifluoropropyloxy, heptafluoropropyloxy, heptafluoroisopropyloxy, 2,2,2-trifluoro-1-(trifluoromethyl)-ethoxy, nonafluorobutoxy, nonafluoro-sec-butoxy, 3,3,4,4,5,5,5-heptafluoropentyloxy, undecafluoropentyloxy, tridecafluorohexyloxy, etc.

[0136] A halocycloalkyl refers to a C3-15 cycloalkyl in which one or more hydrogen atoms are optionally substituted with halogen atoms. A halocycloalkenyl refers to a C3-15 cycloalkenyl in which one or more hydrogen atoms are optionally substituted with halogen atoms.

[0137] The salt may be of any kind, provided it is agriculturally permissible. Examples of such salts include inorganic acids (e.g., hydrochlorides, sulfates, nitrates, etc.), organic acids (e.g., acetates, methanesulfons, etc.), alkali metal salts (e.g., sodium salts, potassium salts, etc.), alkaline earth metal salts (e.g., calcium salts, etc.), and quaternary ammonium salts (e.g., tetramethylammonium salts, tetraethylammonium salts, etc.), with alkali metal salts being preferred and sodium salts being more preferred. The disclosed compositions may contain not only pyrazole compounds, but also pyrazole compounds and salts of pyrazole compounds.

[0138] The following describes a method for producing the pyrazole compound of the present disclosure represented by general formula (1) or a salt thereof. The compound of the present disclosure represented by general formula (1) can be produced, for example, by the following method. Note that the following description is merely illustrative, and the compound of the present disclosure represented by general formula (1) may be produced by other methods. Hereinafter, "the compound of the present disclosure represented by general formula (1)" will also be referred to as "the compound of the present disclosure (1)," and "the compound represented by general formula (2X-1)" will also be referred to as "compound (2X-1)." Other compounds will be described similarly in accordance with this.

[0139] The disclosed compound (1) can be produced, for example, by the following production route.

[0140]

[0141] (In the formula, A, Z, X, T, R １ , R ２ , R ３ , and L are the same as above. R ｔ Q represents a halogen atom, an optionally substituted alkoxy, an optionally substituted alkylcarbonyloxy, or an optionally substituted alkoxycarbonyloxy. １ (This indicates a leaving group.)

[0142] A leaving group is a group that is eliminated during a reaction, and is not particularly limited, but can include halogen atoms such as iodine, bromine, and chlorine atoms; and methylsulfonyloxy groups (-OSO). ２ CH ３ ), p-toluenesulfonyloxy group (-OSO ２ C ６ H ５ CH ３ ), p-chlorobenzenesulfonyloxy group (-OSO ２ C ６ H ５ Cl), trifluoromethylsulfonyloxy group (-OSO ２ CF ３ Examples include:

[0143] If compound (1) is compound (1-A) or compound (1-B), T １ The disclosed compound (1-A-X2) is an oxygen atom, or T ２ The disclosed compound (1-B-X2), in which is an oxygen atom, can be produced, for example, by the following production route.

[0144]

[0145] (In the formula, A, Z, X, R １ , R ２ , R ３Ａ , R ３Ｂ , and L are the same as above.

[0146] Manufacturing Example 1

[0147]

[0148] (In the formula, A, Z, X, T, R １ , R ２ , R ３ , L, and R ｔ (This is the same as above.)

[0149] Compound (1) disclosed herein can be produced by reacting compound (2X-2) or compound (2X-4) with compound (10) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) and a dehydrating condensation agent in a solvent or without a solvent, and optionally in the presence of a base and / or additives.

[0150] Alternatively, the disclosed compound (1) can also be produced by reacting compound (2X-2) or compound (2X-4) with compound (10) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) in a solvent or without a solvent, and optionally in the presence of a base and / or additives.

[0151] The equivalent amount of compound (10) or its salt can be used in amounts of 0.5 to 50 equivalents per equivalent of compound (2X-2) or compound (2X-4). Compound (10) or its salt is a known compound, and some are available commercially. Others can be produced in accordance with the synthesis methods of general known compounds described in the literature. The equivalent amount of the dehydration condensing agent used can be used in amounts of 0.5 to 50 equivalents per equivalent of compound (2X-2) or compound (2X-4).

[0152] There are no particular limitations on the dehydration condensation agent, and examples include 1H-benzotriazole-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, N,N'-dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxidehexafluorophosphate.

[0153] When a solvent is used, there are no particular limitations on the solvent used as long as it is inert to the reaction. Examples include water; alcohol solvents such as methanol, ethanol, and tert-butyl alcohol; ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, and diglym; aromatic hydrocarbon solvents such as benzene, xylene, and toluene; aliphatic hydrocarbon solvents such as n-pentane, n-hexane, and cyclohexane; halogenated hydrocarbon solvents such as dichloromethane, chloroform, and 1,2-dichloroethane; nitrile solvents such as acetonitrile and propionitrile; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and N,N'-dimethylimidazolidinone; dimethyl sulfoxide; pyridine; or mixed solvents thereof.

[0154] When using a base, there are no particular limitations on the base, and examples include organic bases such as pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), and 1,5-diazabicyclo[4.3.0]-5-nonene (DBN); inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium bicarbonate, potassium carbonate, cesium carbonate, and potassium phosphate; and metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide. The amount of base used (equivalent) can be 0.1 to 100 equivalents per equivalent of compound (2X-2) or compound (2X-4).

[0155] There are no particular limitations on the additives that can be used in this reaction, but examples include 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, and 4-(dimethylamino)pyridine. The amount (equivalent) of the additive used can be 0.005 to 100 equivalents per equivalent of compound (2X-2) or compound (2X-4).

[0156] The reaction temperature can be set to any temperature from -78°C to the reflux temperature of the reaction mixture. The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be set to any temperature within the range of 5 minutes to 100 hours.

[0157] Manufacturing Example 2

[0158]

[0159] (In the formula, A, Z, T, R １ , R ２ , R ３ Q １ , and L are the same as above.

[0160] Compound (1X-1), in which X is an oxygen atom, can be obtained by reacting compound (2X-6) and compound (11) in a solvent or without a solvent, in the presence of a base, and optionally in the presence of either a copper catalyst or an additive, or both. Alternatively, it can be obtained by reacting in the presence of a base, and optionally in the presence of a palladium catalyst and a ligand. If compound (2X-6) is a known compound, it can be obtained commercially. Others can be produced according to the general synthesis methods of known compounds described in the literature. Compound (11) can be used in an amount of 0.5 to 50 equivalents per equivalent of compound (2X-6). If compound (11) is a known compound, it can be obtained commercially. Others can be produced according to the general synthesis methods of known compounds described in the literature. When a solvent is used, the solvent only needs to be inert to the reaction, for example, the solvent exemplified in Production Example 1. There are no particular limitations on the base; for example, the bases exemplified in Production Example 1 can be used. The amount of base used (equivalent) can be 0.1 to 100 equivalents per equivalent of compound (2X-6). There are no particular limitations on the copper catalyst; for example, copper iodide (monovalent), copper trifluoromethanesulfonate (monovalent) benzene complex, copper trifluoromethanesulfonate (monovalent) toluene complex, etc. The amount of copper catalyst can be used, for example, 0.001 to 50 equivalents per equivalent of compound (2X-6). There are no particular limitations on the additives that can be used in this reaction; for example, N,N-dimethylglycine, 4-(dimethylamino)pyridine, etc. The amount of additive used (equivalent) can be 0.001 to 100 equivalents per equivalent of compound (2X-6). Examples of palladium catalysts that can be used in this reaction include palladium (divalent) (π-cinnamyl) chloride (dimer), allyl palladium (divalent) chloride (dimer), and tris(dibenzylideneacetone)dipalladium (zero valent). The amount of palladium catalyst used (equivalents) can be 0.001 to 50 equivalents per equivalent of compound (2X-6).Examples of ligands that can be used in this reaction include 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (tert-butyl-XPhos), tetramethyl-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (tetramethyldi-tert-butyl-XPhos), 2-di-(tert-butyl)phosphino-2',4',6'-triisopropyl-3-methoxy-6-methylbiphenyl (RockPhos), 2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl (BrettPhos), and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos). The amount (equivalent) of ligand used can be 0.001 to 50 equivalents per equivalent of compound (2X-6). The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0161] Production Example 3 Of the compounds disclosed herein, compound (1Y-1) can also be produced, for example, by reacting compound (2Y-1) or a salt thereof with compound (10Y) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) in a solvent or without a solvent, and optionally in the presence of a base and / or additives.

[0162]

[0163] (In the formula, A, Z, X, T, R １ , R ２ , R ３ , R ４ , R ５ , R Ｂ１ , R Ｂ２ , R Ｂ３ , R Ｂ４ , R Ｂ５ , and p are the same as above. Q ２ (This indicates a leaving group.)

[0164] The equivalent amount of compound (10Y) or its salt can be used in amounts of 0.5 to 50 equivalents per equivalent of compound (2Y-1). If compound (2Y-1) and compound (10Y) or its salt are known compounds, some can be obtained commercially, or they can be manufactured according to the general synthesis methods of known compounds described in the literature.

[0165] When a solvent is used, there are no particular limitations on the solvent used as long as it is inert to the reaction. Examples include water; alcohol solvents such as methanol, ethanol, and tert-butyl alcohol; ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, and diglym; aromatic hydrocarbon solvents such as benzene, xylene, and toluene; aliphatic hydrocarbon solvents such as n-pentane, n-hexane, and cyclohexane; halogenated hydrocarbon solvents such as dichloromethane, chloroform, and 1,2-dichloroethane; nitrile solvents such as acetonitrile and propionitrile; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and N,N'-dimethylimidazolidinone; dimethyl sulfoxide; pyridine; or mixed solvents thereof.

[0166] When using a base, there are no particular limitations on the base, and examples include organic bases such as pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), and 1,5-diazabicyclo[4.3.0]-5-nonene (DBN); inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium bicarbonate, potassium carbonate, cesium carbonate, and potassium phosphate; and metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide. The amount of base used (equivalent) can be 0.1 to 100 equivalents per equivalent of compound (2Y-1).

[0167] There are no particular limitations on the additives that can be used in this reaction, but examples include 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, and 4-(dimethylamino)pyridine. The amount (equivalent) of the additive used can be 0.005 to 100 equivalents per equivalent of compound (2Y-1).

[0168] The reaction temperature can be set to any temperature from -78°C to the reflux temperature of the reaction mixture. The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be set to any temperature within the range of 5 minutes to 100 hours.

[0169] Manufacturing Example 4 Among the compounds disclosed herein, for example, the following compound (1Z-1) is mixed with compound (1Y-2) or a salt thereof, and formula: R ３Ｂ Q ３ It can be produced by reacting a compound represented by (10Z) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) in a solvent or without a solvent, and optionally in the presence of a base and / or additives.

[0170]

[0171] (In the formula, A, Z, X, T, R １ , R ２ , R ３ , R ４ , R ５ , R Ｂ１ , R Ｂ２ , R Ｂ３ , R Ｂ４ , R Ｂ５ , and p are the same as above. Q ３ (This indicates a leaving group.)

[0172] The equivalent amount of the compound (10Z) or its salt can be used in an amount of 0.5 to 50 equivalents per equivalent of compound (1Y-2). Compound (10Z) or its salt is a known compound, and some are available commercially. Others can be produced in accordance with the synthesis methods of general known compounds described in the literature.

[0173] When a solvent is used, there are no particular limitations on the solvent used as long as it is inert to the reaction. Examples include water; alcohol solvents such as methanol, ethanol, and tert-butyl alcohol; ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, and diglym; aromatic hydrocarbon solvents such as benzene, xylene, and toluene; aliphatic hydrocarbon solvents such as n-pentane, n-hexane, and cyclohexane; halogenated hydrocarbon solvents such as dichloromethane, chloroform, and 1,2-dichloroethane; nitrile solvents such as acetonitrile and propionitrile; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and N,N'-dimethylimidazolidinone; dimethyl sulfoxide; pyridine; or mixed solvents thereof.

[0174] When using a base, there are no particular limitations on the base, and examples include organic bases such as pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), and 1,5-diazabicyclo[4.3.0]-5-nonene (DBN); inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium bicarbonate, potassium carbonate, cesium carbonate, and potassium phosphate; and metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide. The amount of base used (equivalent) can be 0.1 to 100 equivalents per equivalent of compound (1Y-2).

[0175] There are no particular limitations on the additives that can be used in this reaction, but examples include 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, and 4-(dimethylamino)pyridine. The amount (equivalent) of the additive used can be 0.005 to 100 equivalents per equivalent of compound (1Y-2).

[0176] The reaction temperature can be set to any temperature from -78°C to the reflux temperature of the reaction mixture. The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be set to any temperature within the range of 5 minutes to 100 hours.

[0177] (Method for producing intermediate compounds) Of the compounds (2X-2) in reaction formula 1, compound (2X-2A) in which X is an oxygen atom can be produced by the following method.

[0178]

[0179] (In the formula, Q １ A, Z, T, R １ , and R ２(The same applies as above.) Compound (2X-2A) can be obtained by reacting compound (2X-1) and compound (11) in a solvent or without a solvent, in the presence of a base, and optionally in the presence of either a copper catalyst or an additive, or both. Alternatively, it can be obtained by reacting them in the presence of a base, and optionally in the presence of a palladium catalyst and a ligand. If compound (2X-1) is a known compound, it can be obtained commercially. Others can be produced in accordance with the general synthesis methods of known compounds described in the literature. Compound (11) can be used in an amount of 0.5 to 50 equivalents per equivalent of compound (2X-1). If compound (11) is a known compound, it can be obtained commercially. Others can be produced in accordance with the general synthesis methods of known compounds described in the literature. When a solvent is used, the solvent only needs to be inert to the reaction, for example, the solvent exemplified in Production Example 1. There are no particular limitations on the base; for example, the bases exemplified in Production Example 1 can be used. The amount of base used (equivalent) can be 0.1 to 100 equivalents per equivalent of compound (2X-1). There are no particular limitations on the copper catalyst; for example, copper iodide (monovalent), copper trifluoromethanesulfonate (monovalent) benzene complex, copper trifluoromethanesulfonate (monovalent) toluene complex, etc. The amount of copper catalyst used can be, for example, 0.001 to 50 equivalents per equivalent of compound (2X-1). There are no particular limitations on the additives that can be used in this reaction; for example, N,N-dimethylglycine, 4-(dimethylamino)pyridine, etc. The amount of additive used (equivalent) can be 0.001 to 100 equivalents per equivalent of compound (2X-1). Examples of palladium catalysts that can be used in this reaction include palladium (divalent) (π-cinnamyl) chloride (dimer), allyl palladium (divalent) chloride (dimer), and tris(dibenzylideneacetone)dipalladium (zero valent). The amount of palladium catalyst used (equivalents) can be 0.001 to 50 equivalents per equivalent of compound (2X-1).Examples of ligands that can be used in this reaction include 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (tert-butyl-XPhos), tetramethyl-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (tetramethyldi-tert-butyl-XPhos), 2-di-(tert-butyl)phosphino-2',4',6'-triisopropyl-3-methoxy-6-methylbiphenyl (RockPhos), 2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl (BrettPhos), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos), etc. The amount of ligand used (equivalent) can be 0.001 to 50 equivalents relative to 1 equivalent of compound (2X-1). The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.

[0180] Reaction Formula 2 Among compounds (2X-4), the compound (2X-4A) in which X is an oxygen atom can be produced according to the following method.

[0181]

[0182] (In the formula, Q １ , A, Z, T, R １ , R ２ , and, R ｔ(The same as above.) Compound (2X-4A) can be obtained by reacting compound (2X-3) and compound (11) in a solvent or without a solvent, in the presence of a base, and optionally in the presence of either a copper catalyst or an additive, or both. Alternatively, it can be obtained by reacting in the presence of a base, and optionally in the presence of a palladium catalyst and a ligand. If compound (2X-3) is a known compound, it can be obtained commercially. Others can be produced in accordance with the general synthesis methods of known compounds described in the literature. Compound (11) can be used in an amount of 0.5 to 50 equivalents per equivalent of compound (2X-3). If compound (11) is a known compound, it can be obtained commercially. Others can be produced in accordance with the general synthesis methods of known compounds described in the literature. When a solvent is used, the solvent only needs to be inert to the reaction, for example, the solvent exemplified in Production Example 1. There are no particular limitations on the base; for example, the bases exemplified in Production Example 1 can be used. The amount of base used (equivalent) can be 0.1 to 100 equivalents per equivalent of compound (2X-3). There are no particular limitations on the copper catalyst; for example, copper iodide (monovalent), copper trifluoromethanesulfonate (monovalent) benzene complex, copper trifluoromethanesulfonate (monovalent) toluene complex, etc. The amount of copper catalyst used can be, for example, 0.001 to 50 equivalents per equivalent of compound (2X-3). There are no particular limitations on the additives that can be used in this reaction; for example, N,N-dimethylglycine, 4-(dimethylamino)pyridine, etc. The amount of additive used (equivalent) can be 0.001 to 100 equivalents per equivalent of compound (2X-3). Examples of palladium catalysts that can be used in this reaction include palladium (divalent) (π-cinnamyl) chloride (dimer), allyl palladium (divalent) chloride (dimer), and tris(dibenzylideneacetone)dipalladium (zero valent). The amount of palladium catalyst used (equivalents) can be 0.001 to 50 equivalents per equivalent of compound (2X-3).Examples of ligands that can be used in this reaction include 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (tert-butyl-XPhos), tetramethyldi-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (tetramethyldi-tert-butyl-XPhos), 2-di-(tert-butyl)phosphino-2',4',6'-triisopropyl-3-methoxy-6-methylbiphenyl (RockPhos), 2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl (BrettPhos), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos), etc. The usage amount (equivalent) of the ligand can be 0.001 to 50 equivalents relative to 1 equivalent of compound (2X-3). The reaction temperature and reaction time are within the temperature range and time range described in Production Example 1.

[0183] Reaction Formula 3 Compound (2X-4) used in Production Example 1 can be produced, for example, according to the following method.

[0184]

[0185] (In the formula, A, Z, X, T, R １ , R ２ , and R ｔ are the same as described above.) Compound (2X-4) can be obtained by reacting compound (2X-2) with a halogenating agent such as thionyl chloride, phosphorus pentachloride, or oxalyl chloride according to a known method described in the literature, for example, the method described in Journal of Medicinal Chemistry [J. Med. Chem.] 1991, Vol. 34, p. 1630, etc. Alternatively, compound (2X-4) can be obtained by reacting it with an organic acid halide such as pivaloyl chloride or isobutyl chloroformate according to the method described in Tetrahedron Letters [Tetrahedron Lett.] 2003, Vol. 44, p. 4819, Journal of Medicinal Chemistry [J. Med. Chem.] 1991, Vol. 34, p. 222, etc., in the presence of a base if necessary.

[0186] Reaction Equation 4

[0187]

[0188] (In the formula, Q １ , T, R １ , R ２ , and R ｊ (The same as above.) Compound (2X-7) can be obtained from compound (2X-5) by known methods described in the literature, for example, the method described in reaction formula 3 above.

[0189] Reaction Equation 5 Of the compounds (2X-2), R ２ A compound (2X-2B) in which is a hydrogen atom can be produced, for example, by the following method.

[0190]

[0191] (In the formula, A, Z, X, T, and R １ This is the same as above. R １１ (This indicates an alkyl group which may have substituents.)

[0192] Step 1: Compound (2X-8) can be obtained by reacting compound (3X-1) with compound (12) or its salt (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) in a solvent or without a solvent, and possibly in the presence of a base. Some of compound (12) are known compounds, and some are available commercially. Others can be produced according to the general synthesis methods of known compounds described in the literature. Compound (12) or its salt can be used in an equivalent amount of 0.5 to 50 equivalents per equivalent of compound (3X-1). Some of the compounds (3X-1) are known compounds described in Bioorganic & Medicinal Chemistry Letters, 2015, Vol. 25, p. 4481, and others can be synthesized in the same manner as known compounds according to the methods described in the said literature. When a solvent is used, it is sufficient that the solvent is inert to the reaction, for example, the solvent exemplified in Production Example 1. For example, the base exemplified in Production Example 1 can be used in this reaction. The amount of base used (equivalents) can be 0.1 to 100 equivalents per equivalent of compound (3X-1). The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0193] Step 2: Compound (2X-2B) can be obtained by reacting compound (2X-8) with an oxidizing agent in or without a solvent. Examples of oxidizing agents that can be used include potassium permanganate. The amount of oxidizing agent used (in equivalents) can be 0.1 to 100 equivalents per equivalent of compound (2X-8). When a solvent is used, the solvent used only needs to be inert to the reaction, for example, the solvent exemplified in Production Example 1. The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0194] Reaction Equation 6 The compound (2X-2B) can also be produced, for example, by the following method.

[0195]

[0196] (In the formula, A, Z, X, T, and R １ (This is the same as above.)

[0197] Step 1: Compound (2X-9) can be obtained by reacting compound (3X-2) under the same conditions as Step 1 of reaction formula 5. Some of compound (3X-2) are known compounds described in International Publication No. 2003 / 016275, and others can be synthesized in the same manner as known compounds according to the method described in the said document.

[0198] Step 2: Compound (2X-2B) can be obtained by reacting compound (2X-9) with a carbon dioxide source such as carbon dioxide in a solvent or without a solvent in the presence of a base. Examples of bases that can be used include n-butyllithium. The amount of base used (equivalents) can be 0.1 to 100 equivalents per equivalent of compound (2X-9). If a solvent is used, the solvent used only needs to be inert to the reaction, for example, the solvent exemplified in Production Example 1. The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0199] Reaction Equation 7: Compound (2X-2C) in which T is an oxygen atom can be produced, for example, by the following method.

[0200]

[0201] (In the formula, A, Z, X, R １ , and R ２ (The same as above. Q represents a halogen atom, either the same or different.)

[0202] Step 1: Compound (2X-11) can be obtained by reacting compound (2X-10) with a halogenating agent, for example, in a solvent or without a solvent. The halogenating agent is not particularly limited and examples include chlorine, N-chlorosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, bromine, N-bromosuccinimide, N-iodosuccinimide, etc. The amount (equivalent) of halogenating agent used can be 0.1 to 100 equivalents per equivalent of compound (2X-10). When a solvent is used, the solvent is not particularly limited as long as it is inert to the reaction, for example, the solvent exemplified in Production Example 1. The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0203] Step 2: Compound (2X-12) can be obtained by hydrolyzing compound (2X-11) in the presence of an acid such as hydrochloric acid or sulfuric acid, or a base such as calcium carbonate or sodium acetate, in accordance with a known method described in the literature, for example, the method described in Japanese Patent Application Publication No. 2014 / 214118, Journal of Heterocyclic Chemistry, 1992, Vol. 29, p. 691, etc.

[0204] Step 3: Compound (2X-2C) can be obtained by oxidizing compound (2X-12) according to a known method described in the literature, for example, the method described in International Publication No. 2008 / 028688.

[0205] Reaction Equation 8 The compound (2X-2) can be produced, for example, by the following method.

[0206]

[0207] (In the formula, A, Z, X, T, R １ , R ２ , and Q are the same as above.

[0208] Step 1: Compound (2X-13) can be produced by reacting compound (2X-10) with a halogenating agent in or without a solvent. Examples of halogenating agents that can be used include the halogenating agents exemplified in Step 1 of reaction formula 7. The amount (equivalent) of halogenating agent used can be 0.1 to 100 equivalents per equivalent of compound (2X-10). When a solvent is used, the solvent used only needs to be inert to the reaction, for example, the solvent exemplified in Production Example 1. The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0209] Step 2: Compound (2X-14) can be obtained by hydrolyzing compound (2X-13) in the presence of water and a base such as sodium hydroxide, potassium hydroxide, or lithium hydroxide, in accordance with known methods described in the literature, for example, the methods described in International Publication No. 2006 / 067443, International Publication No. 2023 / 033142, etc.

[0210] Step 3: Compound (2X-2) can be obtained by reacting compound (2X-14) with an oxidizing agent in a solvent or without a solvent, in the presence of a catalyst, and optionally in the presence of either a buffer or an additive, or both. Examples of the oxidizing agent that can be used in this reaction include sodium chlorite, an aqueous solution of sodium chlorite, sodium hypochlorite, an aqueous solution of sodium hypochlorite, sodium hypochlorite pentahydrate, and the like. The amount of the oxidizing agent used can be 0.001 to 100 equivalents relative to 1 equivalent of compound (2X-14). Examples of the catalyst that can be used in this reaction include 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO), 2-azabicyclo[2.2.2]octane-N-oxyl (AZADO), and the like. The amount of the catalyst used can be 0.001 to 100 equivalents relative to 1 equivalent of compound (2X-14). Examples of the buffer that can be used in this reaction include sodium dihydrogen phosphate, sodium dihydrogen phosphate dihydrate, acetic acid, and the like. The amount of the buffer used can be 0.5 to 100 equivalents relative to 1 equivalent of compound (2X-14). Examples of the additive that can be used in this reaction include potassium bromide, tetrabutylammonium bromide, and the like. The amount of the additive used can be 0.001 to 100 equivalents relative to 1 equivalent of compound (2X-14). When a solvent is used, the solvent used may be inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.

[0211] Production Example 5 Compound (1X-3) can be produced, for example, according to the following method.

[0212]

[0213] (In the formula, Z, X, T, R １ , R ２ , R ３ , R １２ , and L are the same as described above.)

[0214] Compound (1X-3) can be obtained by reacting compound (1X-2) and compound (13) in a solvent or without a solvent, in the presence of a base, and optionally in the presence of a palladium catalyst and ligand. Some of compound (1X-2) and compound (13) are known compounds, and some are commercially available. Others can be produced according to the general synthesis methods of known compounds described in the literature. The amount of compound (13) used can be 0.5 to 50 equivalents per equivalent of compound (1X-2). When a solvent is used, the solvent used only needs to be inert to the reaction, for example, the solvent exemplified in Production Example 1. For example, the base exemplified in Production Example 1 can be used in this reaction. The amount (equivalent) of base used can be 0.1 to 100 equivalents per equivalent of compound (1X-2). For example, the palladium catalyst exemplified in Reaction Scheme 1 can be used in this reaction. The amount (equivalent) of palladium catalyst used can be 0.001 to 50 equivalents per equivalent of compound (1X-2). Examples of ligands that can be used in this reaction include those exemplified in reaction formula 1. The amount (equivalent) of ligand used can be 0.001 to 50 equivalents per equivalent of compound (1X-2). The reaction temperature and reaction time are within the temperature and time ranges described in production example 1.

[0215] Manufacturing Example 6 Of the compounds (1X-3), R １２ A compound (1X-6) in which is a hydrogen atom can be produced, for example, according to the following production route (reaction pathway).

[0216]

[0217] (In the formula, Z, X, T, R １ , R ２ , R ３ , and L are the same as above. R １３ , R １４ , and R １５ (This represents an alkyl group that may have substituents, or an aryl group that may have substituents, either identical or different.)

[0218] Step 1: Compound (1X-5) can be obtained by reacting compound (1X-4) and silyl compound (13A) in a solvent or without a solvent, in the presence of a base, and optionally in the presence of a palladium catalyst and ligand. Some of compound (1X-4) and silyl compound (13A) are known compounds, and some are commercially available. Others can be produced according to the general synthesis methods of known compounds described in the literature. The amount of compound (13A) used can be 0.5 to 50 equivalents per equivalent of compound (1X-4). When a solvent is used, the solvent used only needs to be inert to the reaction, for example, the solvent exemplified in Production Example 1. For example, the base exemplified in Production Example 1 can be used in this reaction. The amount of base used (equivalents) can be 0.1 to 100 equivalents per equivalent of compound (1X-4). Examples of palladium catalysts that can be used in this reaction include the palladium catalyst illustrated in reaction formula 1. The amount (equivalent) of palladium catalyst used can be 0.001 to 50 equivalents per equivalent of (1X-4). Examples of ligands that can be used in this reaction include the ligand illustrated in reaction formula 1. The amount (equivalent) of ligand used can be 0.001 to 50 equivalents per equivalent of compound (1X-4). The reaction temperature and reaction time are within the temperature and time ranges described in production example 1.

[0219] Step 2: Compound (1X-6) can be obtained by reacting compound (1X-5) with a deprotecting agent in a solvent or without a solvent, in the presence of a base, and optionally in the presence of an organic acid or an inorganic acid. The deprotecting agent that can be used in this reaction is not particularly limited as long as it is a compound used in the deprotection reaction of silyl groups, for example, tetrabutylammonium fluoride. The amount (equivalent) of tetrabutylammonium fluoride used can be 0.001 to 50 equivalents per equivalent of compound (1X-5). The organic acid is not particularly limited, for example, acetic acid, trifluoroacetic acid, methanesulfonic acid, p-tosylic acid, etc. The inorganic acid is not particularly limited, for example, hydrochloric acid, sulfuric acid, etc. The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0220] Method for producing carbonyl pyrazole compounds or salts thereof The method for producing carbonyl pyrazole compounds or salts thereof (1B-A-K1, 1B-A-K2, or 1B-B-K3), in which X is a carbonyl (C=O) group, is not particularly limited and can be produced, for example, by the following method.

[0221] Manufacturing Example 7

[0222] (In the formula, A, Z, R １ , R ２ , R ３Ａ , R ３Ｂ , and L are the same as above. R Ｘ１Ａ R represents an optionally substituted alkyl group, an optionally substituted carbon ring, or an optionally substituted heterocycle. Ｘ２ and R Ｘ３ (This represents an alkyl group, a carbon ring, or a heterocycle, which may have substituents, and which may be the same or different.)

[0223] (Method for producing the intermediate compound) Reaction formula 9 The compound (4B) can also be produced, for example, according to the following production route (reaction pathway).

[0224]

[0225] (In the formula, A, Z, R Ｘ２ , and R Ｘ３ (This is the same as above.)

[0226] Compound (4B) can be obtained by reacting compound (5B) with an N,N-dialkylformamide dialkylacetal, such as N,N-dimethylformamide dimethylacetal, in a solvent. Examples of usable N,N-dialkylformamide dialkylacetals include N,N-dimethylformamide dimethylacetal, N,N-dimethylformamide diethylacetal, N,N-dimethylformamide dipropylacetal, and N,N-dimethylformamide di(t-butyl)acetal. The amount (equivalent) of N,N-dialkylformamide dialkylacetal used can be 0.1 to 100 equivalents per equivalent of compound (5B). The solvent can be any solvent that is inert to the reaction, for example, the solvent exemplified in Production Example 1. The reaction temperature and reaction time are not particularly limited, such as the temperature and time ranges described in Production Example 1.

[0227] Reaction formula 10 The compound (3B) can also be produced, for example, by the following method.

[0228]

[0229] (In the formula, A, Z, R Ｘ１Ａ , R Ｘ２ , and R Ｘ３ (This is the same as above.)

[0230] Compound (3B) can be reacted with compound (4B) and an alkyl oxoacetate in the presence of a solvent. Examples of alkyl oxoacetates include methyl chlorooxoacetate and ethyl chlorooxoacetate. The amount (equivalent) of alkyl oxoacetate used can be 0.1 to 100 equivalents per equivalent of compound (4B). When a solvent is used, the solvent used only needs to be inert to the reaction, for example, the solvent exemplified in Production Example 1. The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0231] Reaction formula 11 The compound (2B-2) can also be produced, for example, by the following method.

[0232]

[0233] (In the formula, A, Z, X, T, R １ , R ２ , R Ｘ１Ａ , R Ｘ２ , and R Ｘ３ (This is the same as above.)

[0234] Compound (2B-2) can be reacted with compound (3B) and a hydrazine compound in the presence of a solvent. Examples of hydrazine compounds include hydrazine monohydrate, methylhydrazine, methylhydrazine hydrochloride, and t-butylhydrazine hydrochloride. Hydrazine compounds also include their salts and hydrates. The amount (equivalent) of hydrazine compound used can be 0.1 to 100 equivalents per equivalent of compound (3B). When a solvent is used, the solvent used only needs to be inert to the reaction; for example, the solvent exemplified in Production Example 1 can be used. The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0235] Reaction formula 12 The compound (2B-1) can also be produced, for example, by the following method.

[0236]

[0237] (In the formula, A, Z, X, T, R １ , R ２ , and R Ｘ１Ａ (This is the same as above.)

[0238] Compound (2B-1) can react with compound (2B-2) in the presence of a solvent. When a solvent is used, it only needs to be inert to the reaction; for example, the solvents exemplified in Production Example 1 can be used. The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0239] The compounds of this disclosure ((A) pyrazole compounds or salts thereof) may be used in combination with other pesticides (e.g., (B) insecticides, (C) fungicides, etc.) or appropriate (D) auxiliary components (optional components).

[0240] There are no particular limitations on the types of pesticides that can be mixed with the compounds disclosed herein. Examples include compounds belonging to groups 1-36 and UN-UNM in the IRAC (Insecticide Resistance Action Committee) classification of action; compounds belonging to A-U, unclassified, etc. in the FRAC (Fungicide Resistance Action Committee) classification of action; compounds belonging to A-Z, etc. in the HRAC (Herbicide Resistance Action Committee) classification of action; and compounds listed in The Pesticide Manual, 18th edition, 2018. Specific examples of their common names are as follows. However, the pesticides used in mixtures are not necessarily limited to these.

[0241] (B) Insecticides The insecticides (insecticidal active compounds) that may be used in combination with the compounds of this disclosure ((A) pyrazole compounds or salts thereof) may be any compounds known to have a control effect on agricultural pests, without any particular limitations. The insecticidal active compounds referred to herein include not only insecticides but also acaricides and nematodeicides. The insecticidal active compounds may be used individually or by mixing two or more as appropriate.

[0242] (B) There are no particular limitations on the insecticidal compounds, but examples include compounds belonging to groups 1 to 36 and UN to UNM in the classification of action by IRAC (Insecticide Resistance Action Committee).

[0243] (b1) Group 1: Acetylcholinesterase (AChE) inhibitors Examples of acetylcholinesterase (AChE) inhibitors include alanicarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl (NAC), carbofuran, carbosulfan, ethiofencarb, fenobucarb (BPMC), formetanate, furathiocarb, isoprocarb (MIPC), methiocarb, methomyl, metolcarb (MTMC), oxamyl, pirimicarb, propoxur (PHC), and thiodicarb. Carbamate compounds such as rb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb (MPMC) (1A); acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusaphos, chlorethoxyfos, chlorphen Chlorfenvinphos (CVP), chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos (CYAP), demeton-S-methyl, diazinon, dichlorvos (DDVP), diclotophos, dimethoate,Dimethylvinphos, ethylthiometone (disulfoton), EPN, ethion, etoprophos, fanphur, fenamiphos, fenitrothion (MEP), fenthion (MPP), fosthiazate, heptenophos, imicyafos, isofenphos nphos), isopropyl-O-(methoxyaminothiophosphoryl)salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion (DMTP), mevinphos, monocrotophos, naled (BRP), omethoate, oxydemeton-methyl, parathion, methylparathion (parathion-methyl), phenthoate (PAP), phorate, phosalone, phosmet (PMP), phosphamidon, phoxim, pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos (CVMP), Thiometon,Examples include organophosphorus compounds such as triazophos, trichlorfon (DEP), and vamidothion (1B).

[0244] (b2) Group 2: GABA-gated chloride ion channel blockers Examples of GABA-gated chloride ion channel blockers include cyclic diene organochlorine compounds such as chlordane and benzoepine (endosulfan) (2A); and phenylpyrazole (fiprole) compounds such as ethiprole and fipronil (2B).

[0245] (b3) Group 3: Sodium channel modulators Examples of sodium channel modulators include acrinathrin, allethrin (d-cis-trans-, d-trans-isomer), bifenthrin, bioallethrin (S-cyclopentenyl-isomer), bioresmethrin, cycloprothrin, and cyfluthrin. Cyfluthrin (β-isomer), Cyhalothrin (λ-, γ-isomer), Cypermethrin (α-, β-, θ-, ζ-isomer), Cyphenothrin [(1R)-trans isomer], Deltamethrin, Empenthrin [(EZ)-(1R)-trans isomer], Esfenvalerate, Etofenprox fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (τ-fluvalinate), halfenprox, imiprothrin, kadethrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin Examples include pyrethroid compounds (3A) such as lethrin, pyrethrins, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-trans isomer], tralomethrin, and transfluthrin; and DDT and methoxychlor (3B).

[0246] (b4) Group 4: Nicotinic acetylcholine receptor (nAChR) competitive modulators Examples of nicotinic acetylcholine receptor (nAChR) competitive modulators include neonicotinic agents such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam. Examples include dichloromethopropyl alcohol compounds (4A); nicotine compounds such as nicotine sulfate (nicotine) (4B); sulfoxymine compounds such as sulfoxaflor (4C); butenolide compounds such as flupyradifurone (4D); mesoionic compounds such as dichloromethothiaz, fenmezoditiaz, and triflumezopyrim (4E); and pyridylidene compounds such as flupyrim (4F).

[0247] (b5) Group 5: Nicotinic acetylcholine receptor (nAChR) allosteric modulators - site I Examples of nicotinic acetylcholine receptor (nAChR) allosteric modulators - site I include spinosine compounds such as spinetram and spinosad.

[0248] (b6) Group 6: Glutamate-gated chloride ion channel (GluCl) allosteric modulators Examples of glutamate-gated chloride ion channel (GluCl) allosteric modulators include avermectin compounds such as abamectin, emamectin-benzoate, lepimectin, milbemycin compounds such as milbemectin, and others.

[0249] (b7) Group 7: Juvenile hormone analogues Examples of juvenile hormone analogues include juvenile hormone analogues such as hydroprene, kinoprene, and methoprene (7A); fenoxycarb (7B); and pyriproxyfen (7C).

[0250] (b8) Group 8: Other nonspecific (multisite) inhibitors Other nonspecific (multisite) inhibitors include, for example, alkyl halides such as 1,3-dichloropropene, methyl bromide, and other alkyl halides (8A); chloropicrin (8B); fluoride compounds such as cryolite (sodium aluminum fluoride) and sulfuryl fluoride (8C); borates such as borax, boric acid, disodium octaborate, sodium borate, and sodium metaborate (8D); tartrate (8E); methyl isothiocyanate generators such as dazomet, metam, and methyl isothiocyanate (8F).

[0251] (b9) Group 9: String organ TRPV channel modulators Examples of string organ TRPV channel modulators include pyridineazomethine derivatives such as pymetrozine and pyrifluquinazon (9B); and pyropene compounds such as afidopyropen (9D).

[0252] (b10) Group 10: Mite growth inhibitors acting on CHS1 Examples of mite growth inhibitors acting on CHS1 include clofentezine, diflovidazin, hexythiazox (10A); etoxazole (10B), etc.

[0253] (b11) Group 11: Microbial-derived insect midgut endometrial disruptors Examples of microbial-derived insect midgut endometrial disruptors include Bacillus thuringiensis subsp. israelensis, Bacillus thuringiensis subsp. Aizawai, Bacillus thuringiensis subsp. Kurstaki, and Bacillus thuringiensis subsp. tenebryonis (proteins contained in Bt crops: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry2Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1) Examples include *Bacillus thuringiensis* and the insecticidal proteins it produces (11A); and *Bacillus sphaericus* (11B).

[0254] (b12) Group 12: Mitochondrial ATP synthase inhibitors Examples of mitochondrial ATP synthase inhibitors include diafenthiuron (12A); organotin acaricides such as azocyclotin, tricyclohexyltin hydroxide (hexatin), and fenbutatin oxide (12B); propargite (BPPS) (12C); and tetradifon (12D).

[0255] (b13) Group 13: Oxidative phosphorylation uncoupling agents that disrupt the proton gradient Examples of oxidative phosphorylation uncoupling agents that disrupt the proton gradient include pyrrole compounds such as chlorfenapyr; dinitrophenol compounds such as DNOC; and sulfuramide.

[0256] (b14) Group 14: Nicotinic acetylcholine receptor (nAChR) channel blockers Examples of nicotinic acetylcholine receptor (nAChR) channel blockers include nereistoxin analogs such as bensultap, cartap hydrochloride, thiocyclam, and thiosultap sodium.

[0257] (b15) Group 15: Chitin biosynthesis inhibitors acting on CHS1 Examples of chitin biosynthesis inhibitors acting on CHS1 include benzoylurea compounds such as bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, nobiflumuron, teflubenzuron, and triflumuron.

[0258] (b16) Group 16: Chitin biosynthesis inhibitors (Type 1) Examples of chitin biosynthesis inhibitors (Type 1) include buprofezin.

[0259] (b17) Group 17: Molting inhibitors (Diptera insects) Examples of molting inhibitors (Diptera insects) include cyromazine.

[0260] (b18) Group 18: Ecdysone receptor agonists Examples of ecdysone receptor agonists include diacylhydrazine compounds such as chromafenozide, halofenozide, methoxyfenozide, and tebufenozide.

[0261] (b19) Group 19: Octopamine receptor agonists Examples of octopamine receptor agonists include amitraz.

[0262] (b20) Group 20: Mitochondrial electron transport chain complex III inhibitor-Qo site Examples of mitochondrial electron transport chain complex III inhibitor-Qo sites include hydramethylnon (20A), acequinocyl (20B), fluacrypyrim (20C), and bifenazate (20D).

[0263] (b21) Group 21: Mitochondrial electron transport chain complex I inhibitors (METIs) Examples of mitochondrial electron transport chain complex I inhibitors (METIs) include fenazaquin, fenpyroximate, pyridaben, pyrimidifen, tebufenpyrad, tolfenpyrad, etc. (21A); and rotenone (21B), etc.

[0264] (b22) Group 22: Voltage-gated sodium channel blockers Examples of voltage-gated sodium channel blockers include oxadiazine compounds such as indoxacarb (22A); and semicarbazone compounds such as metaflumizone (22B).

[0265] (b23) Group 23: Acetyl-CoA carboxylase inhibitors Examples of acetyl-CoA carboxylase inhibitors include tetronic acid or tetramic acid derivatives such as spirodiclofen, spiromesifen, spiropidion, and spirotetramat.

[0266] (b24) Group 24: Mitochondrial electron transport chain complex IV inhibitors Examples of mitochondrial electron transport chain complex IV inhibitors include phosphine compounds such as aluminum phosphide, calcium phosphide, hydrogen phosphide, and zinc phosphide (24A); and cyanides such as hydrogen cyanide (calcium cyanide / sodium cyanide) and potassium cyanide (24B).

[0267] (b25) Group 25: Mitochondrial electron transport chain complex II inhibitors Examples of mitochondrial electron transport chain complex II inhibitors include β-ketonitrile derivatives such as cyenopyrafen and cyflumetofen (25A); and carboxanilide compounds such as pyflubumide (25B).

[0268] (b26) Group 28: Rianodine receptor modulators Examples of ryanodine receptor modulators include diamide compounds such as chlorantraniliprole, cyantraniliprole, cycloniliprole, flubendiamide, and tetraniliprole.

[0269] (b27) Group 29: String organ modulators Examples of string organ modulators include flonicamid.

[0270] (b28) Group 30: GABA-gated chloride ion channel allosteric modulators Examples of GABA-gated chloride ion channel allosteric modulators include metadiamide compounds such as broflanilide, and isoxazoline compounds such as fluxametamide and isocycloseram.

[0271] (b29) Group 31: Baculoviruses Examples of baculoviruses include granulomatous viruses (GVs) such as codlinga Cydia pomonella GV and codlinga mimic Thaumatotibia leucotreta GV, and various multinuclear virus-positive viruses (NPVs) such as velvet bean caterpillar Anticarsia gemmatalis MNPV and tobacco budworm Helicoverpa armigera NPV.

[0272] (b30) Group 32: Nicotinic acetylcholine receptor (nAChR) allosteric modulator - site II Examples of nicotinic acetylcholine receptor (nAChR) allosteric modulators - site II include GS-omega / kappa HXTX-Hv1a peptide.

[0273] (b31) Group 33: Calcium-activated potassium channel (KCa2) modulators Examples of calcium-activated potassium channel (KCa2) modulators include acynonapyr.

[0274] (b32) Group 34: Mitochondrial electron transport chain complex III inhibitor-Qi site Examples of mitochondrial electron transport chain complex III inhibitor-Qi sites include flometoquin.

[0275] (b33) Group 35: RNA interference-mediated targeted repressors Examples of RNA interference-mediated targeted repressors include Ledprona.

[0276] (b34) Group 36: Chordonic organ modulators (target site unspecified) Examples of chordonic organ modulators (target site unspecified) include pyridazines or pyrazole carboxamides such as dimpropyridaz.

[0277] (b35) Group UN: Agent A with an unknown or unclear mechanism of action. Examples of Agent A with an unknown or unclear mechanism of action include azadirachtin, benzoximate, benzpyrimoxan, bromopropylate, quinomethionate, dicofol, lime sulfur mixture, manzeb, oxazosulfyl, pyridalyl, and sulfur. (b36) Group UNB: Bacterial agents (excluding BT agents) with an unknown or unclear mechanism of action. Examples of bacterial agents (excluding BT agents) with an unknown or unclear mechanism of action include Burkholderia spp and Wolbachia pipientis (Zap). (b37) Group UNE: Plant-derived components including synthetics, extracts, or unrefined oils with unknown or unclear mechanisms of action. Examples of plant-derived components including synthetics, extracts, or unrefined oils with unknown or unclear mechanisms of action include Chenopodium ambrosioides near ambrosioides, (American quince) extract, and fatty acid monoesters of glycerin or propanediol in neem oil. (b38) Group UNF: Fungal agents with unknown or unclear mechanisms of action. Examples of fungal agents with unknown or unclear mechanisms of action include Akanthomyces muscarius Ve6, Beauveria bassiana strains, Metarhizium brunneum strain F52, and Paecilomyces fumosoroseus Apopka strain 97. (b39) Group UNM: Nonspecific physical disturbances with unknown or unclear mechanisms of action. Examples of nonspecific physical disturbances with unknown or unclear mechanisms of action include diatomaceous earth and mineral oil.

[0278] (C) Fungicides Fungicides (fungicide-active compounds) that may be used in combination with the compounds of this disclosure ((A) pyrazole compounds or salts thereof) may be compounds known to have a control effect on agricultural pests, and these may be used without particular limitation. The fungicide-active compounds referred to herein include not only fungicides but also bactericidal agents and virucidal agents. The fungicide-active compounds may be used individually or by mixing two or more as appropriate.

[0279] (C) There are no particular limitations on the bactericidal activity compounds. For example, in the classification of action by FRAC (Fungicide Resistance Action Committee), examples include compounds belonging to A (nucleic acid synthesis and metabolism), B (cytoskeleton and motor proteins), C (respiration), D (amino acid and protein biosynthesis), E (signal transduction), F (lipid biosynthesis or transport / cell membrane structure or function), G (cell membrane sterol biosynthesis), H (cell wall biosynthesis), I (cell wall melanin biosynthesis), P (induction of resistance in host plants), M (multi-point contact active compounds), U (unknown mechanism of action), and unclassified.

[0280] Group A (nucleic acid synthesis metabolism) includes, for example, RNA polymerase I inhibitors, adenosine deaminase, DNA / RNA biosynthesis inhibitors, DNA topoisomerase type II (gyrase) inhibitors, and dihydroorotate dehydrogenase inhibitors in denovopyrimidine biosynthesis.

[0281] (c1) Group A1: RNA polymerase I inhibitors (FRAC group code 4) Examples of RNA polymerase I inhibitors include acylalanines such as benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, and metalaxyl-M; oxazolidinones such as oxadixyl; and butyrolactones such as ofurece.

[0282] (c2) Group A2: Adenosine deaminase inhibitors (FRAC group code 8) Examples of adenosine deaminase inhibitors include hydroxy(2-amino-)pyrimidines such as bupirimate, dimethylmol, and etylimole.

[0283] (c3) Group A3: DNA / RNA biosynthesis inhibitors (FRAC group code 32) Examples of DNA / RNA biosynthesis inhibitors include isoxazoles such as hydroxyisoxazole (hymexazole) and isothiazolones such as octylinone.

[0284] (c4) Group A4: DNA topoisomerase type II (gyrase) inhibitors (FRAC group code 31) Examples of DNA topoisomerase type II (gyrase) inhibitors include carboxylic acids such as oxolinic acid. (c5) Group A5: Dihydroorotate dehydrogenase inhibitors in denovopyrimidine biosynthesis (FRAC group code 52) Examples of dihydroorotate dehydrogenase inhibitors in denovopyrimidine biosynthesis include phenylpropanols such as ipuflufenokine and dihydroisoquinolines such as quinofumelin.

[0285] Group B (cytoskeleton and motor proteins) includes, for example, tubulin polymerization inhibitors, cell division (site of action unknown) inhibitors, spectrin-like protein delocalization agents, actin / myosin / fimbrin function inhibitors, and tubulin dynamics modulators.

[0286] (c6) Groups B1, B2, B3: Tubulin polymerization inhibitors (FRAC group codes 1, 10, 22) Examples of β-tubulin polymerization inhibitors include benzimidazoles such as benomyl, carbendazim, fuberidazole, and thiabendazole; thiophanates such as thiophanate and thiophanate-methyl; N-phenylcarbamates such as diethofencarb; toluamides such as zoxamide; and ethylaminothiazolecarboxamides such as ethaboxam.

[0287] (c7) Group B4: Cell division (site of action unknown) inhibitors (FRAC group code 20) Examples of cell division (site of action unknown) inhibitors include phenylureas such as pencycuron.

[0288] (c8) Group B5: Delocalizers for Spectrin-like Proteins (FRAC Group Code 43) Examples of delocalizers for spectrin-like proteins include pyridinylmethylbenzoamides such as fluopicolide and fluopimomide.

[0289] (c9) Group B6: Inhibitors of actin / myosin / fimbrin function (FRAC group code 47) Examples of inhibitors of actin / myosin / fimbrin function include aminocyanoacrylates such as phenamacril; benzophenones such as metrafenone; and benzoylpyridines such as pyriophenone.

[0290] (c10) Group B7: Tubulin dynamics modulators (FRAC group code 53) Examples of tubulin dynamics modulators include pyridazines such as pyridaclomethyl.

[0291] Group C (Respiration) includes, for example, complex I (NADH oxidoreductase) inhibitors, complex II (succinate dehydrogenase) inhibitors, complex III (cytochrome bc1 (ubiquinol oxidase) Qo site (cytb gene)) inhibitors, complex III (ubiquinone reductase Qi site) inhibitors, oxidative phosphorylation uncoupling agents, oxidative phosphorylation, ATP synthase inhibitors, ATP transport inhibitors, and complex III (ubiquinone reductase Q1, Qo site, stigmatine binding mode) inhibitors.

[0292] (c11) Group C1: Complex I (NADH oxidoreductase) inhibitors (FRAC group code 39) Examples of Complex I (NADH oxidoreductase) inhibitors include pyrimidineamines such as diflumetrim; pyrazole carboxamides such as tolfenpyrad; and quinazolines such as fenazaquin.

[0293] (c12) Group C2: Complex II (succinate dehydrogenase) inhibitors (FRAC group code 7) Examples of Complex II (succinate dehydrogenase) inhibitors include phenylbenzamides such as benodanil, flutolanil, and mepronil; phenyloxoethylthiophenamides such as isofetamide; pyridinylethylbenzamides such as fluopyram; phenylcyclobutylpyridineamides such as cyclobutrifluram; francarboxamides such as fenfuram; oxatiincarboxamides such as carboxin and oxicarboxin; thiazolecarboxamides such as thifluzamide; benzovindiflupyr, Examples include pyrazole-4-carboxamides such as bixafen, fluindapyr, fluxapyroxad, furametpyr, impilfluxam, isopyrazam, penflufen, penthiopyrad, and sedaxane; N-cyclopropyl-N-benzylpyrazolecarboxamides such as isoflucypram; N-methoxy(phenylethyl)pyrazolecarboxamides such as pydiflumetofen; pyridinecarboxamides such as boscalid; and pyrazinecarboxamides such as pyraziflumide.

[0294] (c13) Group C3: Complex III (cytochrome bc1 (ubiquinol oxidase) Qo site (cytb gene)) inhibitors. Complex III (cytochrome bc1 (ubiquinol oxidase) Qo site (cytb gene)) inhibitors (QoI bactericides (Qo inhibitors)) (FRAC group code 11) include, for example, methoxyacrylates such as azoxystrobin, coumoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, and pyraoxystrobin; methoxyacetamides such as mandestrobin; pyraclostrobin, pyrametostrobin, and triclopyricarb. Examples include methoxycarbamates such as kresoxim-methyl and trifloxystrobin; oxyiminoacetamides such as dimoxystrobin, fenaminstrobin, metminostrobin, and orysastrobin; oxazolidinediones such as famoxadone; dihydrodioxazines such as fluoxastrobin; imidazolinones such as fenamidone; and benzylcarbamates such as pyribencarb. Additionally, examples of QoI fungicides (Qo inhibitors; subgroup A) (FRAC group code 11A) include tetrazolinones such as methyltetrapyrrole.

[0295] (c14) Group C4: Complex III (ubiquinone reductase Qi site) inhibitors (FRAC group code 21) Examples of Complex III (ubiquinone reductase Qi site) inhibitors include cyanoimidazoles such as cyazofamide; sulfamoyltriazoles such as amisulbrom; and picolinamides such as fenpicoxamide and florylpicoxamide.

[0296] (c15) Group C5: Uncoupling agents for oxidative phosphorylation (FRAC Group Code 29) Examples of uncoupling agents for oxidative phosphorylation include dinitrophenylcrotonic acids such as binapacrill, meptyl dinocap, and DPC (dinocap); 2,6-dinitroanilines such as fluazinam; and pyrimidinone hydrazones such as ferimzone.

[0297] (c16) Group C6: Inhibitors of oxidative phosphorylation and ATP synthase (FRAC group code 30) Examples of inhibitors of oxidative phosphorylation and ATP synthase include triphenyltin compounds such as organotin (triphenyltin acetate, triphenyltin chloride, triphenyltin hydroxide).

[0298] (c17) Group C7: ATP transport inhibitors (FRAC group code 38) Examples of ATP transport inhibitors include thiophenecarboxamides such as silthiofam.

[0299] (c18) Group C8: Complex III (ubiquinone reductase Q1, Qo site, stigmatelin binding mode) inhibitors (FRAC group code 45) Examples of Complex III (ubiquinone reductase Q1, Qo site, stigmatelin binding mode) inhibitors include triazolopyrimidylamines such as ametoctradin.

[0300] Group D (amino acid and protein biosynthesis inhibitors) includes, for example, methionine biosynthesis (cgs gene) inhibitors, protein biosynthesis (liposome translation termination stage) inhibitors, protein biosynthesis (liposome translation initiation stage) inhibitors, protein biosynthesis (liposome polypeptide elongation stage) inhibitors, and leucyl-tRNA synthesis (LeuRNA) inhibitors.

[0301] (c19-1) Group D1: Methionine biosynthesis (cgs gene) inhibitors (FRAC group code 9) Examples of methionine biosynthesis (cgs gene) inhibitors include anilinopyrimidines such as cyprodinil, mepanipyrim, and pyrimethanil.

[0302] (c19-2) Group D2: Protein biosynthesis (liposome translation termination stage) inhibitors (FRAC group code 23) Examples of protein biosynthesis (liposome translation termination stage) inhibitors include enopyranuronic acid antibiotics such as blasticidin S.

[0303] (c19-3) Group D3: Protein biosynthesis (liposome translation initiation stage) inhibitors (FRAC group code 24), Group D4: Protein biosynthesis (liposome translation initiation stage) inhibitors (FRAC group code 25) Examples of protein biosynthesis (liposome translation initiation stage) inhibitors include hexopyranosyl antibiotics such as kasugamycin and glucopyranosyl antibiotics such as streptomycin.

[0304] (c19-4) Group D5: Protein biosynthesis (liposome polypeptide elongation stage) inhibitors (FRAC group code 41) Examples of protein biosynthesis (liposome polypeptide elongation stage) inhibitors include tetracycline antibiotics such as oxytetracycline.

[0305] (c19-5) Group D6: Leucyl-tRNA synthesis (LeuRNA) inhibitors (FRAC group code 54) Examples of leucyl-tRNA synthesis (LeuRNA) inhibitors include benzooxamborols such as tavaborole.

[0306] Group E (signal transduction) includes, for example, signal transduction inhibitors (mechanism of action unknown), MAP / histidine kinase (os-2, HOG1) inhibitors in osmotic signal transduction, and MAP / histidine kinase (os-1, Daf1) inhibitors in osmotic signal transduction.

[0307] (c20) Group E1: Signal transduction (mechanism of action unknown) inhibitors (FRAC group code 13) Examples of signal transduction (mechanism of action unknown) inhibitors include allyloxyquinolines such as quinoxyfen; and quinazolinones such as proquinazid.

[0308] (c21) Group E2: MAP / histidine kinase (os-2, HOG1) inhibitors in osmotic signaling (FRAC group code 12) Examples of MAP / histidine kinase (os-2, HOG1) inhibitors in osmotic signaling include phenylpyrroles such as fenpiclonil and fludioxonil.

[0309] (c22) Group E3: MAP / histidine kinase (os-1, Daf1) inhibitors in osmotic signaling (FRAC group code 2) Examples of MAP / histidine kinase (os-1, Daf1) inhibitors in osmotic signaling include dicarboximides such as chlozolinate, dimethachlone, iprodione, procymidone, and vinclozolin.

[0310] Group F (inhibitors of lipid biosynthesis or transport / cell membrane structure or function) includes, for example, methyltransferase inhibitors of phospholipid biosynthesis, inhibitors of cell lipid peroxidation, cell membrane permeable fatty acid inhibitors, ergosterol binders, inhibitors of lipid homeostasis and transfer / storage, interactions with cell membrane lipid fractions, and inhibitors of multiple effects on the cell membrane.

[0311] (c23) Group F2: Methyltransferase inhibitors of phospholipid biosynthesis (FRAC Group Code 6) Examples of methyltransferase inhibitors of phospholipid biosynthesis include phosphorothiolates such as EDDP (edifenphos), IBP (ipropenphos), and pyrazophos; and dithiolanes such as iso-prothiolane.

[0312] (c24) Group F3: Cellular lipid peroxidation inhibitors (FRAC group code 14) Examples of cellular lipid peroxidation inhibitors include aromatic hydrocarbons such as biphenyl, chloroneb, CNA (dicloran), PCNB (quintozene), tecnazen, and tolclofos-methyl; and 1,2,4-thiadiazoles such as etridiazole.

[0313] (c25) Group F4: Cell membrane permeable fatty acid inhibitors (FRAC group code 28) Examples of cell membrane permeable fatty acid inhibitors include carbamates such as prothiocarb, iodocarb, propamocarb, and propamocarb.

[0314] (c26) Group F8: Ergosterol binders (FRAC group code 48) Examples of ergosterol binders include amphiphilic macrolide antifungal antibiotics produced by actinomycetes Streptomyces natalensis or S. chattanoogensis, such as natamycin (pimaricin).

[0315] (c27) Group F9: Inhibitors of lipid homeostasis and transfer / storage (FRAC Group Code 49) Examples of inhibitors of lipid homeostasis and transfer / storage include piperidinyl thiazole isoxazolines such as oxathiapiprolin and fluoxapiprolin.

[0316] (c28) Group F10: Interaction with cell membrane lipid fraction, inhibitors of multiple effects on the cell membrane (FRAC group code 51) Examples of interactions with cell membrane lipid fraction and inhibitors of multiple effects on the cell membrane include polypeptides and polypeptides such as ASFBIOF01-02.

[0317] Group G (inhibitors of cell membrane sterol biosynthesis) includes, for example, inhibitors of the C14 demethylase (erg11 / cyp51) in sterol biosynthesis, and Δ in sterol biosynthesis. １４ Reductase and Δ ８ →Δ ７ Examples include isomerase (erg24, erg2) inhibitors, 3-keto reductase (erg27) inhibitors involved in C4 demethylation of sterol biosynthesis, and squalene epoxidase (erg1) inhibitors in the sterol biosynthesis pathway.

[0318] (c29) Group G1: Inhibitors of C14 demethylases (erg11 / cyp51) in sterol biosynthesis (FRAC Group Code 3) Inhibitors of C14 demethylases in sterol biosynthesis include, for example, piperazines such as triforine; pyridines such as pyrifenox and pyrisoxazole; pyrimidines such as fenarimol and nuarimol; imidazoles such as imazalil, oxpoconazole, pefurazoate, prochloraz, and triflumizole; azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxyconazole, etaconazole, and fenbuconazole. Examples include triazoles such as nbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenzonazole, ipconazole, mefentrifluconazole, metconazole, microbutanil, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, and triticonazole; and triazolinthions such as prothioconazole.

[0319] (c30) Group G2: Δ in sterol biosynthesis １４ Reductase and Δ ８ →Δ ７ Inhibitors of isomerases (erg24, erg2) (FRAC group code 5) in Δ sterol biosynthesis １４ Reductase and Δ ８ →Δ ７ Examples of isomerase (ERG24, ERG2) inhibitors include morpholins such as aldimorph, dodemorph, fenpropimorph, and tridemorph; piperidines such as fenpropidin and piperalin; and spirochetalamines such as spiroxamine.

[0320] (c31) Group G3: 3-keto reductase (erg27) inhibitors in C4 demethylation of sterol biosynthesis (FRAC Group Code 17) Examples of 3-keto reductase (erg27) inhibitors in C4 demethylation of sterol biosynthesis include hydroxyanilides such as fenhexamide and aminopyrazolinones such as fenpyrazamine.

[0321] (c32) Group G4: Inhibitors of squalene epoxidase (erg1) in sterol biosynthesis (FRAC Group Code 18) Examples of inhibitors of squalene epoxidase (erg1) in sterol biosynthesis include thiocarbamates such as pyributicarb, and allylamines such as naphthifine and terbinafine.

[0322] Examples of H group inhibitors (cell wall biosynthesis inhibitors) include chitin synthase inhibitors and cellulose synthase inhibitors.

[0323] (c33) Group H4: Chitin synthase inhibitors (FRAC group code 19) Examples of chitin synthase inhibitors include peptidylpyrimidine nucleosides such as polyoxine, which is an antibiotic used in agricultural chemicals. Polyoxine is an antifungal antibiotic produced by the actinomycete Streptomyces cacaoi. There are 14 types of polyoxine, with the main components being A, B, and D.

[0324] (c34) Group H5: Cellulose synthase inhibitors (FRAC group code 40) Examples of cellulose synthase inhibitors include cinnamic acid amides such as dimethomorph, flumorph, and pyrimorph; valineamide carbamates such as benthiavalicarb, iprovalicarb, and valifenalate; and mandelic acid amides such as mandipropamide.

[0325] Group I (melanin synthesis inhibitors in the cell wall) includes, for example, inhibitors of melanin biosynthesis reductases, melanin biosynthesis dehydrases, and melanin biosynthesis polyketide synthases.

[0326] (c35) Group I1: Melanin biosynthesis reductase inhibitors (FRAC Group Code 16.1) Examples of melanin biosynthesis reductase inhibitors include isobenzofuranones such as fthalide; pyrroloquinolinones such as pyroquilon; and triazolobenzothiazoles such as tricyclazole.

[0327] (c36) Group I2: Dehydrating enzyme inhibitors for melanin biosynthesis (FRAC Group Code 16.2) Examples of dehydrating enzyme inhibitors for melanin biosynthesis include cyclopropanecarboxamides such as carpropamide; carboxamides such as diclocimet; and propionamides such as fenoxanil.

[0328] (c37) Group I3: Polyketide synthase inhibitors for melanin biosynthesis (FRAC Group Code 16.3) Examples of polyketide synthase inhibitors for melanin biosynthesis include trifluoroethylcarbamates such as tolprocarb.

[0329] Group P (c38) Host plant resistance inducers (excluding saccharin or its salts) Examples of Group P (host plant resistance inducers) include resistance inducers that stimulate the salicylic acid pathway, host plant resistance inducers, plant extracts that induce resistance in host plants, microorganisms that induce resistance in host plants, and microbial preparations. Note that saccharin or its salts are not included in said host plant resistance inducers.

[0330] Group P1: Resistance inducers that stimulate the salicylate pathway (FRAC group code P1) Examples of resistance inducers that stimulate the salicylate pathway (salicylic acid signaling) include benzothiadiazole BTHs such as acibenzolar-S-methyl.

[0331] Group P2: Host plant resistance inducers (FRAC group code P2) Examples of host plant resistance inducers (salicylic acid signaling) include benzoisothiazoles such as probenazole. Group P3: Host plant resistance inducers (FRAC group code P3) Examples of host plant resistance inducers (salicylic acid signaling) include thiadiazole carboxamides such as thiadinil and isothianil.

[0332] Group P4: Host plant resistance inducers (FRAC group code P4) Examples of host plant resistance inducers (polysaccharide elicitors, natural products) include polysaccharides such as laminarin. Group P5: Plant extracts that induce resistance in host plants (FRAC group code P5) Examples of plant extracts that induce resistance in host plants (anthraquinone elicitors, plant extracts) include mixtures such as Japanese knotweed extract, ethanol extracts (anthraquinones, resveratrol), etc. Group P6: Microorganisms and microbial preparations that induce resistance in host plants (FRAC group code P6) Examples of microorganisms and microbial preparations that induce resistance in host plants (microbial elicitors, microorganisms) include bacteria of the Bacillus genus such as Bacillus mycoides isolate J, and fungi of the Saccharomyces genus such as the cell wall of Saccharomyces cerevisia LAS117 strain.

[0333] Group P7: Host plant resistance inducers (FRAC group code P7) Examples of host plant resistance inducers (phosphonates) include ethyl phosphonates such as fosetyl, phosphites and their salts. Group P8: Host plant resistance inducers (FRAC group code P8) Examples of host plant resistance inducers (salicylic acid signaling) include isothiazolyl methyl ethers such as diclobentiazox.

[0334] (c39) Compounds with an unknown mechanism of action (Group: Unknown mode of action) (U) (FRAC group codes 27, 34, 35, 36, 37, U6, U12, U13, U14, U16, U17, U18) Compounds with an unknown mechanism of action (Group: Unknown mode of Examples of "actions" include cyanoacetamidooximes such as cymoxanil; phthalamicins such as teclofthalam; benzotriazines such as triazoxide; benzenesulfonamides such as flusulfamide; pyridazinones such as diclomezine; phenylacetamides such as cyflufenamide; guanidines such as dodine; cyanomethylenthezolidines such as fluthianil; pyrimidinone hydrazones such as ferimzone; 4-quinolylacetic acid such as tebufloquin; tetrazolyloximes such as picarbutrazox; and glucopyranosyl antibiotics such as validamycin.

[0335] Group M (c40) Multi-point contact active compounds (M) Examples of multi-point contact active compounds (M) include inorganic compounds (electrophiles), dithiocarbamate compounds and analogs (electrophiles), phthalimides (electrophiles), chloronitriles (phthalonitriles) (site of action unknown), bisguanidines (cell membrane disruptors, surfactants), triazines, quinones (anthraquinones) (electrophiles), quinoxalines (electrophiles), maleimides (electrophiles), susulfamides, thiocarbamates, etc. Preferably, multi-point contact active compounds (M) are inorganic compounds (electrophiles), chloronitriles (phthalonitriles) (site of action unknown), and bisguanidines (cell membrane disruptors, surfactants).

[0336] Inorganic compounds (electrophiles) (FRAC group codes M1, M2) Examples of inorganic compounds (electrophiles) include copper compounds and sulfur compounds. Examples of copper compounds include copper, DBEDC, basic copper oxychloride, basic copper sulfate, copper hydroxide, and copper nonylphenol sulfonate. Examples of sulfur compounds include sulfur and lime sulfur.

[0337] Dithiocarbamates and related compounds (electrophiles) (FRAC Group Code M3) Examples of dithiocarbamates and related compounds (electrophiles) include amobam, ferbam, mancozeb, maneb, metiram, propineb, thiram, zinc thiazole, zineb, ziram, and other dithiocarbamates and related compounds.

[0338] Phthalimides (electrophiles) (FRAC group code M4) Examples of phthalimide compounds (electrophiles) include phthalimides such as captan, captafol, and folpet.

[0339] Chloronitriles (phthalonitriles) (site of action unknown) (FRAC group code M5) Examples of chloronitrile (phthalonitrile) compounds include chlorothalonil (TPN, chlorothalonil) and other chloronitriles (phthalonitriles).

[0340] Sulfamides (FRAC group code M6) Examples of sulfamides include sulfamines (diclofluanid), tolylfluanid, and other sulfamides.

[0341] Bisguanidines (cell membrane disruptors, surfactants) (FRAC group code M7) Examples of bisguanidines include guazatine, iminoctadine acetate, and iminoctadine albesilate (iminoctadine). Triazines (FRAC group code M8) Examples of triazines include anilazine.

[0342] Quinones (Anthraquinones) (Electrophiles) (FRAC Group Code M9) Examples of quinones (anthraquinones) (electrophiles) include dithianone and other quinones (anthraquinones).

[0343] Quinoxalines (electrophiles) (FRAC group code M10) Examples of quinoxalines (electrophiles) include quinoxalines such as quinomethionate.

[0344] Maleimide (electrophile) (FRAC group code M11) Examples of maleimide (electrophile) include maleimides such as fluoroimide. Thiocarbamate (FRAC group code M12) Examples of thiocarbamates include thiocarbamates such as methasulfocarb.

[0345] BM Group (c41) Biopesticides with Multiple Mechanisms of Action: Plant Extracts (BM) (FRAC Group Code BM1) Biopesticides with multiple mechanisms of action: Examples of plant extracts include polypeptides (lectins) such as extracts from the cotyledons of Japanese bean seedlings; phanol, sesquiterpenes, triterpenoids, coumarins such as extracts from Swinglea glutunosa; extracts from Melaleuca alternifolia (tea tree oil), vegetable oils (mixtures), terpene hydrocarbons such as eugenol, geraniol, and thymol, as well as terpene alcohols and terpene phenols.

[0346] In this disclosure, (A) a pyrazole compound or a salt thereof is blended with an insecticide or fungicide in an amount of 0.001 to 1,000,000 parts by mass, preferably 0.01 to 1,000,000 parts by mass, more preferably 0.1 to 10,000 parts by mass, and even more preferably 0.3 to 1,000 parts by mass per 100 parts by mass of pyrazole compound or a salt thereof.

[0347] (D) There are no particular limitations on auxiliary components (optional components), and for example, solid carriers, liquid carriers, gaseous carriers, formulation aids, surfactants, etc. can be added to the extent that the effects of the disclosed compound or composition are not impaired.

[0348] Examples of solid carriers include natural minerals such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth; inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride; and synthetic silicic acid and synthetic silicates.

[0349] Examples of liquid carriers include alcohols such as ethylene glycol, propylene glycol, and isopropanol; aromatic hydrocarbons such as xylene, alkylbenzene, and alkylnaphthalene; ethers such as butyl cellosolve; ketones such as cyclohexanone; esters such as γ-butyrolactone; acid amides such as N-methylpyrrolidone and N-octylpyrrolidone; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, and castor oil; and water. These solid and liquid carriers may be used individually or in combination of two or more.

[0350] Examples of gaseous carriers include butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide.

[0351] Examples of pharmaceutical additives include binders, dispersants, and stabilizers.

[0352] Examples of adhesives or dispersants include casein, gelatin, polysaccharides (starch powder, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, sugars, and synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.). Examples of stabilizers include PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids or their esters.

[0353] Examples of surfactants include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene styrylphenyl ethers, polyoxyethylene polyoxypropylene block copolymers, polyoxyethylene fatty acid esters, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters; anionic surfactants such as alkyl sulfates, alkylbenzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkylnaphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, salts of formalin condensates of alkylnaphthalene sulfonic acid, polyoxyethylene alkylaryl ether sulfates or phosphates, polyoxyethylene styrylphenyl ether sulfates or phosphates, polycarboxylates, and polystyrene sulfonates; cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts; and amphoteric surfactants such as amino acid type and betaine type.

[0354] The content of these surfactants is not particularly limited, but is generally preferred to be in the range of 0.05 to 20 parts by weight per 100 parts by weight of the formulation of the present invention containing the surfactant. Furthermore, these surfactants may be used individually or in combination of two or more types.

[0355] When using the compounds disclosed herein as agricultural chemicals, they may be mixed and applied with other herbicides, insecticides, acaricides, nematicides, fungicides, plant growth regulators, synergists, fertilizers, soil conditioners, etc., as needed during formulation or application.

[0356] In particular, by mixing and applying it with other pesticides or plant hormones, it is possible to reduce costs by decreasing the amount of pesticide applied, expand the fungicidal and insecticidal spectrum through the synergistic effect of the mixed agents, and achieve higher pest control effects. In this case, it is also possible to combine it with multiple known pesticides simultaneously.

[0357] In the disclosed composition, when two components, such as component (A) and component (B), or component (A) and component (C), are blended, the total amount can generally be 0.01 to 95% by mass, preferably 0.1 to 50% by mass, and more preferably 1 to 30% by mass. When three components, such as component (A), component (B), and component (C), are blended, the total amount of components (A) to (C) can generally be 0.01 to 95% by mass, preferably 0.1 to 50% by mass, and more preferably 1 to 30% by mass.

[0358] These application rates and concentrations vary depending on the type of formulation, application timing, application location, application method, type of pest, and degree of damage, and can be increased or decreased without being limited to the above ranges.

[0359] Examples of pests that can be controlled by the compounds disclosed herein include insects, mites, nematodes, mollusks, and other harmful organisms; as well as plant pathogens such as filamentous fungi, bacteria, and viruses.

[0360] The insects, mites, nematodes, mollusks, etc. that can be controlled by the disclosed compounds include, specifically, the following:

[0361] The compounds disclosed herein can generally be used as fungicides and mycicides for agricultural and horticultural purposes against various diseases caused by root-leaved molds, oomycetes, zygomycetes, ascomycetes, basidiomycetes, imperfect fungi, bacteria, or viruses.

[0362] "Pathogenic fungi" refers to microorganisms that cause plant diseases, and specifically includes, but is not limited to, the following microorganisms. Taphrina spp. (e.g., Taphrina deformans, T. pruni, etc.), Pneumocystis spp., Geotrichum spp., Candida spp. (e.g., Candida albicans, C. sorbosa, etc.), Pichia spp. (e.g., Pichia kluyveri, etc.), Capnodium spp., Fumago spp., Hypocapnodium spp., Cercospora spp. (e.g. Cercospora apii, C. asparagi, C. beticola, C. capsici, C. carotae, C. kaki, C. kikuchii, C. zonata, etc.), Cercosporidium spp., Cladosporium spp. (e.g. Cladosporium colocasiae, C. cucumerinum, C. variabile etc.), Davidiella spp., Didymosporium spp., Heterosporium spp. (e.g., Heterosporium allii, etc.), Mycosphaerella spp. (e.g., Mycosphaerella arachidis, M. berkeleyi, M. cerasella, M. fijiensis, M. fragariae, M. graminicola, M. nawae, M. pinodes, M. pomi, M. zingiberis, etc.), Mycovellosiella spp. (e.g., Mycovellosiella fulva, M. nattrassii, etc.), Paracercospora spp. (e.g., Paracercospora egenula, etc.), Phaeoisariopsis spp., Phaeoramularia spp., Pseudocercospora spp. (e.g., Pseudocercospora abelmoschi, P. fuligena, P. vitis, etc.), Pseudocercosporella spp.(e.g., Pseudocercosporella capsellae, etc.), Ramichloridium spp., Ramularia spp., Septogloeum spp., Septoria spp. (e.g., Septoria albopunctata, S. apiicola, S. chrysanthemella, S. helianthi, S. obesa, etc.), Sphaerulina spp., Aureobasidium spp., Kabatiella spp., Plowrightia spp., Stigmina spp., Elsinoe spp. (e.g., Elsinoe ampelina, E. araliae, E. fawcettii, etc.), Sphaceloma spp. (e.g., Sphaceloma caricae, etc.), Ascochyta spp. (e.g., Ascochyta pisi, etc.), Corynespora spp. (e.g., Corynespora cassiicola, etc.), Leptosphaeria spp. (e.g., Leptosphaeria coniothyrium, L. maculans, etc.), Saccharicola spp., Phaeosphaeria spp. (e.g., Phaeosphaeria nodorum, etc.), Ophiosphaerella spp., Setophoma spp., Helminthosporium spp., Alternaria spp. (e.g., Alternaria alternata, A. brassicae, A. brassicicola, A. citri, A. dauci, A. helianthi, A. japonica, A. kikuchiana, A. mali, A. panax, A. porri, A. radicina, A. solani, etc.), Bipolaris spp. (e.g., Bipolaris sorghicola, etc.), Cochliobolus spp. (e.g., Cochliobolus heterostrophus, C. lunatus, C. miyabeanus, etc.), Curvularia spp. (e.g., Curvularia geniculata, C.verruculosa spp., Drechslera spp., Pleospora spp., Pleospora herbarum spp., Pyrenophora spp. teres (Setosphaeria spp.) Setosphaeria turcica (Setosphaeria turcica) Stemphylium spp. lycopersici、S. solani、S. vesicarium spp., Venturia spp., Venturia carpophila, V. vesicarium spp. Inaequalis、V. nashicola、V. pyrin activity) and Didymella spp. fabae, Hendersonia spp., Phoma spp., Phoma erratica var. mikan、P. exigua var. exigua、P. wasabiae active) Pyrenochaeta spp spp. Botryosphaeria berengeriana f. sp. piricola、B. dothidea activity) Dothiorella spp. Fusicoccum spp. Guignardia spp. Lasiodiplodia spp spp. Phyllosticta spp.(also) Phyllosticta zingiberis spp.(also) Schizothyrium pomi spp.Acrospermum spp.Leptosphaerulina spp.Aspergillus spp., Penicillium spp.(from Penicillium digitatum, P. italicum、P. sclerotigenum spp., Trichophyton spp., Trichophyton mentagrophytes. rubrum spp., Histoplasma spp., Blumeria spp., Blumeria graminis f. sp. hordei、B. gf sp. tritici), Erysiphe spp. cichoracearum、E. c. var. cichoracearum、E. heraclei、E. low activity) Golovinomyces spp. latisporus spp., Leveillula spp., Leveillula taurica spp., Microsphaera spp., Oidium spp., Oidium neolycopersici spp., Phyllactinia spp.(Phyllactinia kakicola)P. mali、P. moricola, Podosphaera spp., Podosphaera fusca, P. leucotricha、P. pannosa、P. tridactyla var. tridactyla、P. xanthii activity) and Sphaerotheca spp. aphanis、S. fuliginea agent) and Uncinula spp. n. var. necator agent) (Uncinuliella spp.) Uncinuliella simulans var. simulans、U.S. s. var. tandae spp., Blumeriella jaapii spp., Cylindrosporium spp., Diplocarpon spp. mespili、D.rosae spp., Gloeosporium spp., Gloeosporium minus spp., Marssonina spp., Tapesia spp. yallundae, Lachnum spp., Scleromitrula spp., Botryotinia spp. byssoidea、B. cinerea、B. elliptic、B. fabae、B. squamosa agent) Ciborinia spp. Grovesinia spp. Monilia mumecola Monilinia spp. fructigena、M. laxa、M. mali、M. vaccinii-corymbosiactivity), Sclerotinia spp. homoeocarp、S. minor、S. sclerotiorum spp., Valdensia heterodoxa spp., Claviceps spp. sorghicola agent) Epichloe spp. Ephelis japonica Villosiclava virens Hypomyces spp. sp. mori、H. sf sp. low activity) Trichoderma spp.(also) Trichoderma viride activity) Calonectria spp.(an activity) Candelospora spp spp., Cylindrocladium spp., Fusarium spp. crookwellense、F. culmorum、F. cuneirostrum、F. oxysporum、F. of sp.adzukicola, F. of sp. allii, F. of sp. asparagi, F. of sp. batatas, F. o. f. sp. cepae, F. of sp. colocasiae, F. of sp. conglutinans, F. of sp. cubense, F. of sp. cucumerinum, F. of sp. fabae, F. of sp. fragariae, F. of sp. lactucae, F. of sp. lagenariae, F. of sp. lycopersici, F. of sp. melongenae, F. of sp. melonis, F. of sp. nelumbinicola, F. of sp. niveum, F. of sp. radicis-lycopersici, F. of sp. raphani, F. of sp. spinaciae, F. sporotrichioides, F. solani, F. sf sp. cucurbitae, F. sf sp. eumartii, F. sf sp. glycines, F. sf sp. pisi, F. sf sp. Radicicola, F. virguliforme, etc.), Gibberella spp. (e.g., Gibberella avenacea, G. baccata, G. fujikuroi, G. zeae, etc.), Haematonectria spp., Nectria spp., Ophionectria spp., Caldariomyces spp., Myrothecium spp., Trichothecium spp., Verticillium spp. (e.g., Verticillium albo-atrum, V. dahliae, V. longisporum, etc.), Ceratocystis spp. (e.g., Ceratocystis ficicola, C. fimbriata, etc.), Thielaviopsis spp.(including Thielaviopsis basicola) and Adisciso spp. Monochaetia spp. (including Pestalotia eriobotrifolia spp.) in Pestalotiopsis spp.(Pestalotiopsis funerea) P. longiseta、P. neglecta、P. theae, Physalospora spp., Nemania spp., Nodulisporium spp., Rosellinia spp nivalis spp., Ophiostoma spp., Cryphonectria spp., Cryphonectria parasitica spp., Diaporthe spp. kyushuensis、D. nomurai、D. tanakae, Diaporthopsis spp., Phomopsis spp. fukushii、P. obscurans、P. vexans , Cryptosporella spp , Discula spp , Discula theae-sinensis , Gnomonia spp , Coniella spp , Coryneum spp , Greeneria spp , Melanconis spp., Cytospora spp., Leucostoma spp., Valsa spp.(also, Valsa ceratosperma activity) Tubakia spp., Monosporascus spp., Clasterosporium spp., Gaeumannomyces spp.(such as Gaeumannomyces graminis) Magnaporthe spp.(such as Magnaporthe grisea) Pyricularia spp.(such as Pyricularia zingiberis (Monilochaetes infuscans), Colletotrichum spp.(e.g., Colletotrichum acutatum, C. capsici, C. cereale, C. destructivum, C. fragariae, C. lindemuthianum, C. nigrum, C. orbiculare, C. spinaciae, etc.), Glomerella spp. (e.g., Glomerella cingulata, etc.), Khuskia oryzae, Phyllachora spp. (e.g., Phyllachora pomigena, etc.), Ellisembia spp., Briosia spp., Cephalosporium spp. (e.g., Cephalosporium gramineum, etc.), Epicoccum spp., Gloeocercospora sorghi, Mycocentrospora spp., Peltaster spp. (e.g., Peltaster fructicola, etc.), Phaeocytostroma spp., Phialophora Ascomycota fungi such as spp. (e.g., Phialophora gregata), Pseudophloeosporella dioscoreae, Pseudoseptoria spp., Rhynchosporium spp. (e.g., Rhynchosporium secalis), Sarocladium spp., Coleophoma spp., and Helicoceras oryzae. Septobasidium spp. (e.g., Septobasidium bogoriense, S. tanakae, etc.), Helicobasidium spp. (e.g., Helicobasidium longisporum, etc.), Coleosporium spp. (e.g., Coleosporium plectranthi, etc.), Cronartium spp., Phakopsora spp. (e.g., Phakopsora artemisiae, P. nishidana, P. pachyrhizi, etc.), Physopella spp. (e.g., Physopella ampelopsidis, etc.), Kuehneola spp.(including Kuehneola japonica species), Phragmidium spp.(including Phragmidium fusiforme), P. mucronatum、P. rosae-multiflorae agent) Gymnosporangium spp. yamadae) and Puccinia spp. brachypodii var. poae-nemoralis、P. crown、P. c. var. crown、P. cynodontis、P. graminis、P. g. subsp. graminicola、P. hordei、P. horiana、P. kuehnii、P. melanocephala、P. recondite、P. striiformis var. striiformis、P. tanaceti var. tanaceti、P. tokyensis、P. zoysiae, Uromyces spp., Uromyces phaseoli var. azukicola、U. p. var. phaseoli、Uromyces viciae-fabae var. viciae-fabae, Naohidemyces vaccinii, Nyssopsora spp., Leucotelium spp., Tranzschelia spp spp.(including Blastospora smilacis) Uredo spp. Sphacelotheca spp. Urocystis spp. Sporisorium spp spp.(Ustilago maydis,U. nuda, Entyloma spp., Exobasidium spp. vexans agent), Microstroma spp., Tilletia spp.(e.g., controversa, T. laevis), Itersonilia spp. (e.g., Itersonilia perplexans), Cryptococcus spp., Bovista spp. (e.g., Bovista dermoxantha), Lycoperdon spp. (e.g., Lycoperdon curtisii, L. perlatum), Conocybe spp. (e.g., Conocybe apala), Marasmius spp. (e.g., Marasmius oreades), Armillaria spp., Helotium spp., Lepista spp. (e.g., Lepista subnuda), Sclerotium spp. (e.g., Sclerotium cepivorum), Typhula spp. (e.g., Typhula incarnata, T. ishikariensis var. ishikariensis), Athelia spp. (e.g., Athelia Fungi of the phylum Basidiomycota, such as rolfsii, Ceratobasidium spp. (e.g., Ceratobasidium cornigerum), Ceratorhiza spp., Rhizoctonia spp. (e.g., Rhizoctonia solani), Thanatephorus spp. (e.g., Thanatephorus cucumeris), Laetisaria spp., Waitea spp., Fomitiporia spp., Ganoderma spp., Chondrostereum purpureum, and Phanerochaete spp. Fungi of the phylum Chitridiomycota, such as Olpidium spp. Fungi of the phylum Blastocladiomycota, such as Physoderma spp. Choanephora spp., Choanephoroidea cucurbitae, Mucor spp. (e.g., Mucor fragilis), Rhizopus spp. (e.g., Rhizopus arrhizus, R. chinensis, R. oryzae, R.Fungi of the subphylum Mucoromycotina such as stolonifer var. stolonifer, etc. Protists of the phylum Cercozoa such as Plasmodiophora spp. (e.g., Plasmodiophora brassicae, etc.), Spongospora subterranea f. sp. Subterranea, etc. Aphanomyces spp. (e.g., Aphanomyces cochlioides, A. raphani, etc.), Albugo spp. (e.g., Albugo macrospora, A. wasabiae, etc.), Bremia spp. (e.g., Bremia lactucae, etc.), Hyaloperonospora spp., Peronosclerospora spp., Peronospora spp. (e.g., Peronospora alliariae - wasabi, P. chrysanthemi - coronarii, P. destructor, P. farinosa f. sp. spinaciae, P. manshurica, P. parasitica, P. sparsa, etc.), Plasmopara spp. (e.g., Plasmopara halstedii, P. nivea, P. viticola, etc.), Pseudoperonospora spp. (e.g., Pseudoperonospora cubensis, etc.), Sclerophthora spp., Phytophthora spp. (e.g., Phytophthora cactorum, P. capsici, P. citricola, P. citrophthora, P. cryptogea, P. fragariae, P. infestans, P. melonis, P. nicotianae, P. palmivora, P. porri, P. sojae, P. syringae, P. vignae f. sp. adzukicola, etc.), Pythium spp. (e.g., Pythium afertile, P. aphanidermatum, P. apleroticum, P. aristosporum, P. arrhenomanes, P. buismaniae, P.debaryanum, P. graminicola, P. horinouchiense, P. irregulare, P. iwayamai, P. myriotylum, P. okanoganense, P. paddicum, P. paroecandrum, P. periplocum, P. spinosum, P. sulcatum, P. sylvaticum, P. ultimum var. ultimum, P. vanterpoolii, P. Oomycetes of the phylum Heterokontophyta, such as P. vexans, P. volutum, etc. Gram-positive bacteria of the phylum Actinobacteria, such as Clavibacter spp. (e.g., Clavibacter michiganensis subsp. michiganensis), Curtobacterium spp., Leifsonia spp. (e.g., Leifsonia xyli subsp. xyli), and Streptomyces spp. (e.g., Streptomyces ipomoeae). Gram-positive bacteria of the phylum Firmicutes, such as Clostridium sp. Gram-positive bacteria of the phylum Tenericutes, such as Phytoplasma. Rhizobium spp. (e.g., Rhizobium radiobacter, etc.), Acetobacter spp., Burkholderia spp. (e.g., Burkholderia andropogonis, B. cepacia, B. gladioli, B. glumae, B. plantarii, etc.), Acidovorax spp. (e.g., Acidovorax avenae subsp. avenae, A. a. subsp. citrulli, A. konjaci, etc.), Herbaspirillum spp., Ralstonia spp. (e.g., Ralstonia solanacearum, etc.), Xanthomonas spp. (e.g., Xanthomonas albilineans, X. arboricola pv. pruni, X. axonopodis pv. vitians, X.campestris e.g. campestris、X. c. e.g. cucurbitae、X. c. e.g. glycines、X. c. e.g. mangiferaeindicae、X. c. e.g. nigromaculans、X. c. e.g. vesicatory、X. citri subsp. citri、X. oryzae e.g. oryzae) and Pseudomonas spp. fluorescence、P. marginalis、P. m. e.g. marginalis、P. savastanoi e.g. glycinea、P. syringae、P. s. e.g. actinidiae、P. s. e.g. eriobotryae、P. s. e.g. helianthi、P. s. e.g. lachrymans、P. s. e.g. maculicola、P. s. e.g. mori、P. s. e.g. morsprunorum, P. s. e.g. spinaciae、P. s. e.g. syringae、P. s. e.g. theae、P. viridiflava spp., Rhizobacter spp., Brenneria spp., Brenneria nigrifluens spp., Dickeya spp. zeae, Erwinia spp., Erwinia amylovora, E. rhapontici agent), Pantoea spp., Pectobacterium spp. carotovorum, P. carotovorum. wasabiae (Proteobacteria).

[0363] Specific examples of plant diseases caused by infection and proliferation of these pathogens include, but are not limited to, the following. Peach leaf curl (Taphrina deformans), plum pockets (Taphrina pruni), asparagus leaf spot (Cercospora asparagi), sugar beet leaf spot (Cercospora beticola), bell pepper frogeye leaf spot (Cercospora capsici), persimmon angular leaf spot (Cercospora kaki), soybean purple stain (Cercospora kikuchii), peanut brown leaf spot (Mycosphaerella arachidis), cherry brown leaf spot (Mycosphaerella cerasella, Blumeriella jaapii), black sigatoka (Mycosphaerella fijiensis), yellow sigatoka (Mycosphaerella ell Musicola, Wheat leaf blotch (Mycosphaerella graminicola), Persimmon leaf spot (Mycosphaerella nawae), Pea brown spot (Mycosphaerella pinodes), Ginger leaf spot (Mycosphaerella zingiberis), Tomato leaf mold (Mycovellosiella fulva), Eggplant leaf mold (Mycovellosiella nattrassii), Tomato leaf mold (Pseudocercospora fuligena), Grape leaf spot (Pseudocercospora vitis), Chinese cabbage leaf spotLeaf spot (Pseudocercosporella capsellae), Chrysanthemum black spot (Leaf spot (Septoria chrysanthemella)), Chrysanthemum brown spot (Leaf blight (Septoria obesa)), Grape black rot (Anthracnose (Elsinoe ampelina)), Aralia scab (Spot anthracnose (Elsinoe araliae)), Citrus scab (Scab (Elsinoe fawcettii)), Pea brown spot (Leaf spot (Ascochyta pisi)), Cucumber brown spot (Corynespora leaf spot (Corynespora cassiicola)), Rose branch blight (Stem canker (Leptosphaeria coniothyrium)), Wheat flammability (Glume blotch (Leptosphaeria nodorum)), Rose black spot (Leaf spot (Alternaria alternata)), Cabbage black spot (Alternaria leaf spot (Alternaria brassicae)), Carrot black leaf blight (Leaf blight (Alternaria dauci), pear black spot (Alternaria kikuchiana), apple leaf spot (Alternaria mali), onion leaf spot (Alternaria porri), sorghum purple spot (Bipolaris sorghicola), corn southern leaf blight (Cochliobolus heterostrophus), rice brown spot (Cochliobolus miyabeanus), garlic tip blight (Pleospora herbarum), barley stripe (Pyrenophora graminea), barley net blotch (Pyrenophora teres), sorghum leaf blight (Setosphaeria turcica), corn northern leaf blight (Setosphaeria turcica)turcica), asparagus leaf spot (Stemphylium botryosum), black spot (Venturia carpophila), apple scab (Venturia Inaequalis), pear scab (Venturia nashicola), gummy stem blight (Didymella bryoniae), burdock leaf spot (Phoma exigua var. exigua), wasabi streak (Phoma wasabiae), ring rot (Botryosphaeria berengeriana f. sp. piricola), kiwi fruit soft rot (Botryosphaeria dothidea, Lasiodiplodia theobromae, Diaporthe sp.), common green mold (Penicillium digitatum), citrus blue mold Powdery mildew (Penicillium italicum), which occurs in various crops, including barley powdery mildew (Blumeria graminis f. sp. hordei), wheat powdery mildew (Blumeria graminis f. sp. tritici), cucumber powdery mildew (Erysiphe betae, Leveillula taurica, Oidium sp., Podosphaera xanthii), eggplant powdery mildew (Erysiphe cichoracearum, Leveillula taurica, Sphaerotheca fuliginea), carrot and parsley powdery mildew (Erysiphe heraclei), pea powdery mildew (Erysiphe pisi), tomato powdery mildew (Leveillula taurica, Oidium neolycopersici, Oidium sp.), and bell pepper powdery mildew (Leveillula taurica), pumpkin powdery mildew (Oidium sp., Podosphaera xanthii), bitter melon powdery mildew (OidiumPowdery mildew of oysters (Phyllactinia kakicola), powdery mildew of burdock (Podosphaera fusca), powdery mildew of apples (Podosphaera leucotricha), powdery mildew of roses (Podosphaera pannosa, Uncinuliella simulans var. simulans, U. s. var. tandae), powdery mildew of zucchini and cantaloupe (Podosphaera xanthii), powdery mildew of strawberries (Sphaerotheca aphanis var. aphanis), powdery mildew of watermelons and melons (Sphaerotheca fuliginea), powdery mildew of grapes (Uncinula necator, U. n. var. necator), apple blotch (Diplocarpon mali), rose black spot (Diplocarpon rosae), gray mold neck rot of onions (Botrytis Allii), Gray mold, Botrytis blight (Botrytis cinerea), Leaf blight (Botrytis cinerea, B. byssoidea, B. squamosa), Chocolate spot (Botrytis cinerea, B. elliptica, B. fabae), Brown rot (Monilinia fructicola, M. fructigena, M. laxa), Blossom blight (Monilinia mali), Dollar spot (Sclerotinia homoeocarpa), Cottony rot, Sclerotinia rot, Stem rot (Sclerotinia sclerotiorum), False smut (Villosiclava virens), Root necrosis (Calonectria sclerotiorum) Fusarium blight (Fusarium crookwellense, F. culmorum,Gibberella avenacea, G. zeae, Monographella nivalis), Fusarium blight of barley (Fusarium culmorum, Gibberella avenacea, G. zeae), Dry rot of taro (Fusarium oxysporum, F. solani f. sp. radicicola), Brown rot of yam (Fusarium oxysporum, F. solani f. sp. pisi, F. s. f. sp. radicicola), Fusarium wilt of adzuki bean (Fusarium oxysporum f. sp. adzukicola), Fusarium basal rot of Chinese chive (Fusarium oxysporum f. sp. allii, F. solani f. sp. radicicola), Stem rot of sweet potato (Fusarium oxysporum f. sp. batatas, F. solani), Dry rot of taro (Fusarium oxysporum f. sp. colocasiae), Yellows of cabbage and Komatsuna (Fusarium oxysporum f. sp. conglutinans), Panama disease of banana (Fusarium oxysporum f. sp. cubense), Fusarium wilt of strawberry (Fusarium oxysporum f. sp. fragariae), Root rot of lettuce (Fusarium oxysporum f. sp. lactucae), Fusarium wilt of watermelon (Fusarium oxysporum f. sp. lagenariae, F. o. f. sp. niveum), Fusarium wilt of tomato (Fusarium oxysporum f. sp. lycopersici), Fusarium wilt of melon (Fusarium oxysporum f. sp. melonis), Yellows of radish (Fusarium oxysporum f.Fusarium sp. raphani), spinach wilt (Fusarium oxysporum f. sp. spinaciae), soybean sudden death syndrome (Fusarium solani f. sp. Glycines, Fusarium virguliforme), rice bakanae disease (Gibberella fujikuroi), radish verticillium black spot (Verticillium albo-atrum, V. dahliae), tomato, eggplant, and butterbur verticillium wilt (Verticillium dahliae), fig canker (Ceratocystis ficicola), sweet potato black rot (Ceratocystis fimbriata), tea ring spot (Pestalotiopsis longiseta, P. theae), Endothia canker (Cryphonectria parasitica), Citrus black spot (Diaporthe citri), Asparagus stem blight (Phomopsis asparagi), Pear canker (Phomopsis fukushii), Eggplant brown spot (Phomopsis vexans), Tea anthracnose (Discula theae-sinensis), Apple canker (Valsa ceratosperma), Rice blast (Magnaporthe grisea), Strawberry anthracnose (Colletotrichum acutatum, C. fragariae, Glomerella cingulata), Apple anthracnose (Bitter rot (Colletotrichum acutatum, Glomerella cingulata), Anthracnose (Colletotrichum acutatum, Glomerella)Anthracnose of plums (Colletotrichum acutatum), Ripe rot of grapes (Colletotrichum acutatum, Glomerella cingulata), Anthracnose of chrysanthemums (Colletotrichum acutatum), Anthracnose of kidney beans (Colletotrichum lindemuthianum), Anthracnose of cucurbits (Colletotrichum orbiculare), Anthracnose of yams (Glomerella cingulata), Anthracnose of chestnuts (Glomerella cingulata), Anthracnose of persimmons (Glomerella cingulata), Brown stem rot of adzuki beans (Phialophora gregata), Leaf spot of yams (Pseudophloeosporella sporata Dioscoreae), barley scald (Rhynchosporium secalis), wheat brown rust (Puccinia recondita), wheat stripe rust (Puccinia striiformis), rust affecting various crops, fig rust (Phakopsora nishidana), soybean rust (Phakopsora pachyrhizi), rose rust (Kuehneola japonica, Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae), pear cedar-apple rust (Gymnosporangium asiaticum), apple cedar-apple rust (Gymnosporangium yamadae), rust affecting onions (Puccinia allii), chrysanthemum white rust (Puccinia horiana), chrysanthemum black rust (Puccinia tanaceti var. tanaceti), broad bean rust (Uromyces viciae-fabae var. viciae-fabae), sugarcane smut (Sporisorium)scitamineum), corn smut (Ustilago maydis), barley loose smut (Ustilago nuda), tea net blister blight (Exobasidium reticulatum), tea blister blight (Exobasidium vexans), white mold, stem rot, southern blight (Athelia rolfsii), chrysanthemum root and stem rot (Ceratobasidium cornigerum, Rhizoctonia solani), ginger sheath blight (Rhizoctonia solani), cabbage seedling damping-off (Rhizoctonia solani), Japanese parsley damping-off (Rhizoctonia solani), lettuce bottom rot (Rhizoctonia solani), grass leaf blight (Brown patch, Large patch, Rhizoctonia solani), rice sheath blight blight (Thanatephorus cucumeris), sugar beet root rot (Thanatephorus cucumeris), sugar beet leaf blight (Thanatephorus cucumeris), fig black mold (Rhizopus rot, Rhizopus stolonifer var. stolonifer), clubroot (Plasmodiophora brassicae), sugar beet black root rot (Aphanomyces cochlioides), white rust (Albugo macrospora), downy mildew affecting various crops, lettuce downy mildew (Bremia lactucae), garland chrysanthemum downy mildew (Peronospora chrysanthemi-coronarii), onion and leek downy mildew (Peronospora destructor), spinach downy mildew (Peronospora farinosa f. sp.) spinaciae, soybean mildew (PeronosporaManshurica, Brassicaceae downy mildew (Peronospora parasitica), rose downy mildew (Peronospora sparsa), sunflower downy mildew (Plasmopara halstedii), three-leaf downy mildew (Plasmopara nivea), grape downy mildew (Plasmopara viticola), Cucurbitaceae downy mildew (Pseudoperonospora cubensis), Aralia elata root rot (Phytophthora cactorum), watermelon brown rot (Phytophthora capsici), pumpkin rot (Phytophthora capsici), bell pepper rot (Phytophthora capsici), watermelon rot (Phytophthora cryptogea), tomato and potato late blight (Phytophthora infestans), fig rot (White Powdery rot (Phytophthora palmivora), Leaf blight (Phytophthora porri) of the onion family, Phytophthora root and stem rot (Phytophthora sojae) of soybeans, Phytophthora stem rot (Phytophthora vignae f. sp. adzukicola) of adzuki beans, Damping-off (Pythium aphanidermatum, P. myriotylum, P. paroecandrum, P. ultimum var. ultimum) of spinach, Root rot (Pythium aristosporum) of konjac, Browning root rot (Pythium arrhenomanes, P. graminicola) of corn, Damping-off (Pythium buismaniae, P. myriotylum) of cabbage seedlings, Root rot (Pythium myriotylum), ginger rhizome rot (root disease)rot (Pythium myriotylum, P. ultimum var. ultimum), carrot brown blotted root rot (Pythium sulcatum), tomato canker (Clavibacter michiganensis subsp. michiganensis), potato scab (Streptomyces spp.), rose crown gall (Rhizobium radiobacter), sorghum bacterial stripe (Burkholderia andropogonis), onion soft rot (Burkholderia cepacia, Pseudomonas marginalis pv. marginalis, Erwinia rhapontici), rice bacterial grain rot (Burkholderia gladioli, B. glumae), watermelon bacterial fruit blotch (Acidovorax avenae subsp. Bacterial leaf blight (Acidovorax konjaci), Bacterial leaf blight (Ralstonia solanacearum), Bacterial shot hole (Xanthomonas arboricola pv. pruni, Pseudomonas syringae pv. syringae, Brenneria) nigrifluens), Bacterial leaf spot (Xanthomonas arboricola pv. pruni), Bacterial leaf spot (Xanthomonas axonopodis pv. vitians), Black rot (Xanthomonas campestris pv. campestris), Bacterial pustule (Xanthomonas campestris pv. glycines), burdock black spot bacterial disease Bacterialspot (Xanthomonas campestris pv. nigromaculans), bacterial spot on bell pepper (Xanthomonas campestris pv. vesicatoria), citrus canker (Xanthomonas citri subsp. citri), garlic spring rot (Pseudomonas cichorii, P. marginalis pv. marginalis, Erwinia sp.), lettuce rot (Pseudomonas cichorii, P. marginalis pv. marginalis, P. viridiflava), bacterial blossom blight on kiwi fruit (Pseudomonas marginalis pv. marginalis, P. syringae pv. syringae, P. viridiflava), bacterial canker on kiwi fruit (Pseudomonas syringae pv. Actinidiae), loquat canker (Pseudomonas syringae pv. eriobotryae), bacterial spot on cucurbits (Pseudomonas syringae pv. lachrymans), bacterial black spot on brassicas (Pseudomonas syringae pv. maculicola), bacterial canker on plums (Pseudomonas syringae pv. morsprunorum, Erwinia sp.), bacterial shoot blight on tea leaves (Pseudomonas syringae pv. theae), bacterial soft rot on leeks (Dickeya sp., Pectobacterium carotovorum), fire blight on roses (Erwinia amylovora), soft rot on konjac (Pectobacterium carotovorum), bacterial soft rotOne example is rot (Pectobacterium carotovorum).

[0364] In addition to their use as fungicides for agriculture and horticulture, the compounds disclosed herein can also be used as antifungal agents or internal parasite control agents for medical and animal use, as well as antibacterial and antifungal agents for wood, paper and pulp, adhesives and paints, textiles and leather, etc., and as industrial disinfectants for cooling water channels in manufacturing plants, etc.

[0365] Examples of pathogens targeted as antimicrobial agents for medical or veterinary use include, but are not limited to, dermatophytes such as Trichophyton rubrum and Trichophyton mentagrophytes, Candida such as Candida albicans, Aspergillus such as Aspergillus fumigatus, Cryptococcus such as Cryptococcus neoformas, Gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa and Haemophilus influenzae, and Gram-positive bacteria such as Staphylococcus aureus and Streptococcus pyogenes.

[0366] Examples of fungal strains targeted as antibacterial and antifungal agents include wood-rotting fungi such as Tyromyces palustris and Coriolus versicolor, and material degradation microorganisms such as Aspergillus niger, Aspergillus terreus, Eurotium tonophilum, Penicillium citrinum, Penicillium funiculosum, Rhizopus oryzae, Cladosporium cladosporioides, Aureobasidium pullulans, Gliocladium virens, Chaetomium globosum, Fusarium moniliforme, and Myrothecium verrucaria, but are not limited to these.

[0367] Examples of bacterial strains targeted for industrial disinfectant use include, but are not limited to, slime fungi such as Sphaerotilis natans and Zoogloea ramigera.

[0368] In addition to its use as a fungicide for agricultural and horticultural purposes, the disclosed compound can also be used as a control agent for internal parasites in livestock, poultry, or pet animals.

[0369] The following are some examples of internal parasites that may be affected, but they are not limited to these: Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Couperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia, Trichuris, and Strongirus. Nematodes such as *Trichonema*, *Dictyocaulus*, *Capillaria*, *Heterakis*, *Toxocara*, *Ascaridia*, *Oxyuris*, *Ancylostoma*, *Uncinaria*, *Toxascaris*, and *Parascaris*; Nematodes of the family Filariidae, such as Wuchereria, Brugia, Onchoceca, Dirofilaria, and Loa; Nematodes of the family Dracunculidae, such as Deacunculus; Dipylidium caninum, Taenia taeniaeformis, Taenia solium, Taenia saginata, Hymenolepis diminuta, Moniezia benedeni, Diphyllobothrium latum, Diphyllobothrium erinacei, and Echinococcus granulosus Tapeworms such as *Echinococcus granulosus* and *Echinococcus multilocularis*; liver fluke (*Fasciola hepatica*, F.Species such as giantantica, Paragonimus westermanii, Fasciolopsic bruski, Eurytrema pancreaticum, E. coelomaticum, Clonochis sinensis, Schistosoma japonicum, Schistosoma haematobium, Schistosoma mansoni, and other trematodes; Eimeria tenella, Eimeria acervulina, Eimeria brunetti, Eimeria maxima, Eimeria necatrix, Eimeria bovis, Eimeria obioidalis Eimeria spp. (such as *Eimeria ovinoidalis*); Trypanosomsa cruzi; Leishmania spp.; Plasmodium spp. (malaria parasite); Babesia spp.; Trichomonadidae spp.; Histomanas spp.; Giardia spp.; Toxoplasma spp.; Entamoeba histolytica; Theileria spp., etc.

[0370] Methods of application of the compositions disclosed herein include, for example, in the case of granular formulations, seedling tray treatment (mixing before covering with soil at sowing, mixing with bed soil before sowing, and spraying during the seedling stage), side application, surface application, water inlet application, and aerial spraying, and in the case of liquid formulations, seedling tray drenching treatment, foliar spraying, and aerial spraying.

[0371] The application rate and concentration of the disclosed compound or composition can be varied over a wide range depending on weather conditions, application time, application location, application method, etc., but typically the application rate of component (A) contained in the disclosed compound or composition is about 0.01 to 100 g / a in total, preferably about 0.03 to 30 g / a, more preferably about 0.1 to 10 g / a.

[0372] The present disclosure will be described in more detail below with reference to examples, but the technical scope of the present disclosure is not limited to these examples.

[0373] Next, we will show some examples of formulations. Note that "parts" refers to "parts by mass".

[0374] Formulation Example 1 (Emulsion) The compound of the present disclosure can be dissolved in 45 parts of Solvesso 150 and 35 parts of N-methylpyrrolidone, and 10 parts of an emulsifier (product name: Solpol 3005X, manufactured by Toho Chemical Co., Ltd.) can be added and stirred to obtain 10% emulsions of each.

[0375] Formulation Example 2 (Wettable Powder) A 20% wettable powder can be obtained by adding 20 parts of the compound of this disclosure to a mixture of 2 parts of sodium lauryl sulfate, 4 parts of sodium ligninsulfonate, 20 parts of synthetic hydrated silicon dioxide fine powder, and 54 parts of clay, and stirring and mixing with a juice mixer.

[0376] Formulation Example 3 (Granules) Five parts of the compound disclosed herein were mixed thoroughly with two parts sodium dodecylbenzenesulfonate, ten parts bentonite, and eighty-three parts clay. An appropriate amount of water was added and the mixture was stirred further. The mixture was then granulated using a granulator and air-dried to obtain 5% granules.

[0377] Formulation Example 4 (Powder) One part of the compound of this disclosure is dissolved in an appropriate amount of acetone, and five parts of synthetic hydrated silicon dioxide fine powder, 0.3 parts of acidic isopropyl phosphate (PAP), and 93.7 parts of clay are added thereto, and the mixture is stirred and mixed in a juice mixer, and the acetone is evaporated to obtain a 1% powder.

[0378] Formulation Example 5 (Flowable Formulation) Mix 20 parts of the compound of this disclosure, 3 parts of polyoxyethylene tristyrylphenyl ether phosphate triethanolamine, and 0.2 parts of rhodasil 426R in 20 parts of water, wet grind using a Dynomill, and then mix with 60 parts of water containing 8 parts of propylene glycol and 0.32 parts of xanthan gum to obtain a 20% aqueous suspension.

[0379] Formulation Example 6 (Liquid Formulation) A 10% liquid formulation of each can be obtained by stirring and mixing 10 parts of the compound of this disclosure, 5 parts of polyoxyethylene sorbitan monostearate, 5 parts of propylene glycol, and 70 parts of water.

[0380] <Ether-linked type> Synthesis example 1: Synthesis of 1-(tert-butyl)-N-((2,4-dichlorobenzyl)oxy)-4-(3-((trimethylsilyl)ethynyl)phenoxy)-1H-pyrazole-5-carboxamide (1a-9)

[0381]

[0382] 400 mg of 1-(tert-butyl)-N-((2,4-dichlorobenzyl)oxy)-4-(3-iodophenoxy)-1H-pyrazole-5-carboxamide (1b-1) and 7 mL of 1,4-dioxane were mixed to a solution to which 500 μL of triethylamine, 170 mg of trimethylsilylacetylene, 25 mg of palladium chloride ditriphenylphosphine complex, and 14 mg of copper iodide were added, and the mixture was stirred at 80°C for 15 hours. After the reaction was complete, water was added to the reaction solution, and it was extracted once with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 5:1) to obtain 360 mg of the target product (1a-9) as an oil.

[0383] Synthesis Example 2: Synthesis of 1-(tert-butyl)-N-((2,4-dichlorobenzyl)oxy)-4-(3-(ethinylphenoxy)-1H-pyrazole-5-carboxamide (1a-3)

[0384]

[0385] 250 mg of 1-(tert-butyl)-N-((2,4-dichlorobenzyl)oxy)-4-(3-((trimethylsilyl)ethynyl)phenoxy)-1H-pyrazole-5-carboxamide (1a-9) and 2.5 mL of tetrahydrofuran were mixed and 700 μL of tetrabutylammonium fluoride (approximately 1 mol / L tetrahydrofuran solution) was added, and the mixture was stirred at 25°C for 14 hours. After the reaction was complete, water was added to the reaction solution and extracted once with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 5:1) to obtain 50 mg of the target product (1a-3) as an oily substance.

[0386] Synthesis Example 3: Synthesis of 1-(tert-butyl)-N-(2,4-dimethylphenethyl)-4-(3-((trimethylsilyl)ethynyl)phenoxy)-1H-pyrazole-5-carboxamide (1a-7)

[0387]

[0388] 250 mg of 1-(tert-butyl)-N-(2,4-dimethylphenethyl)-4-(3-iodophenoxy)-1H-pyrazole-5-carboxamide (1b-3) (1A-A1-b3 in the table) and 4.8 mL of 1,4-dioxane were mixed and 340 μL of triethylamine, 120 mg of trimethylsilylacetylene, 17 mg of palladium chloride ditriphenylphosphine complex, and 9.2 mg of copper iodide were added, and the mixture was stirred at 80°C for 15 hours. After the reaction was complete, water was added to the reaction solution and extracted once with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 5:1) to obtain 190 mg of the target product (1a-7) as an oil.

[0389] Synthesis Example 4: Synthesis of 1-(tert-butyl)-N-(2,4-dimethylphenethyl)-4-(3-(ethinylphenoxy)-1H-pyrazole-5carboxamide (1a-1)

[0390]

[0391] 150 mg of 1-(tert-butyl)-N-(2,4-dimethylphenethyl)-4-(3-((trimethylsilyl)ethynyl)phenoxy)-1H-pyrazole-5-carboxamide (1a-7) was mixed with 1.5 mL of tetrahydrofuran. 620 μL of tetrabutylammonium fluoride (approximately 1 mol / L tetrahydrofuran solution) was added to this mixture and the mixture was stirred at 25°C for 14 hours. After the reaction was complete, water was added to the reaction solution and it was extracted once with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 5:1) to obtain 120 mg of the target product (1a-1) as a white solid.

[0392] Synthesis Example 5: Synthesis of 1-(tert-butyl)-N-((2,4-dimethylbenzyl)oxy)-4-(3-(prop-1-in-1-yl)phenoxy)-1H-pyrazole-5-carboxamide (1a-5)

[0393]

[0394] 400 mg of 1-(tert-butyl)-N-((2,4-dimethylbenzyl)oxy)-4-(3-iodophenoxy)-1H-pyrazole-5-carboxamide (1b-2) and 8 ml of 1,4-dioxane were mixed to a solution to which 530 μL of triethylamine, 1.8 mL of propyne (approximately 1 mol / L tetrahydrofuran solution), 27 mg of palladium chloride ditriphenylphosphine complex, and 15 mg of copper iodide were added, and the mixture was stirred at 25°C for 15 hours. After the reaction was complete, water was added to the reaction solution, and it was extracted once with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 5:1) to obtain 220 mg of the target product (1a-5) as an oil.

[0395] Synthesis Example 6: Synthesis of 1-(tert-butyl)-N-((2,4-dimethylbenzyl)oxy)-4-(3-(pento-1-in-1-yl)phenoxy)-1H-pyrazole-5-carboxamide (1a-15)

[0396]

[0397] 200 mg of 1-(tert-butyl)-N-((2,4-dimethylbenzyl)oxy)-4-(3-iodophenoxy)-1H-pyrazole-5-carboxamide (1b-2) and 4 mL of 1,4-dioxane were mixed to a solution to which 270 μL of triethylamine, 60 mg of 1-pentine, 14 mg of palladium chloride ditriphenylphosphine complex, and 7.3 mg of copper iodide were added and the mixture was stirred at 50°C for 15 hours. After the reaction was complete, water was added to the reaction solution and extracted once with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 5:1) to obtain 70 mg of the target product (1a-15) as an oil.

[0398] Synthesis Example 7: Synthesis of 1-(tert-butyl)-4-(3-(cyclopropylethynyl)phenoxy)-N-((2,4-dimethylbenzyl)oxy)-1H-pyrazole-5-carboxamide (1a-16)

[0399]

[0400] 200 mg of 1-(tert-butyl)-N-((2,4-dimethylbenzyl)oxy)-4-(3-iodophenoxy)-1H-pyrazole-5-carboxamide (1b-2) and 4 mL of 1,4-dioxane were mixed to a solution to which 270 μL of triethylamine, 60 mg of cyclopropylacetylene, 14 mg of palladium chloride ditriphenylphosphine complex, and 7.3 mg of copper iodide were added and the mixture was stirred at 50°C for 15 hours. After the reaction was complete, water was added to the reaction solution and extracted once with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 5:1) to obtain 100 mg of the target product (1a-16) as an oil.

[0401] Synthesis Example 8: Synthesis of 1-(tert-butyl)-N-((2,4-dimethylbenzyl)oxy)-4-(3-(3-hydroxyprop-1-in-1-yl)phenoxy)-1H-pyrazole-5-carboxamide (1a-10)

[0402]

[0403] 200 mg of 1-(tert-butyl)-N-((2,4-dimethylbenzyl)oxy)-4-(3-iodophenoxy)-1H-pyrazole-5-carboxamide (1b-2) and 4 mL of 1,4-dioxane were mixed to a solution to which 270 μL of triethylamine, 60 mg of 2-propyne-1-ol, 14 mg of palladium chloride ditriphenylphosphine complex, and 7.3 mg of copper iodide were added and the mixture was stirred at 80°C for 15 hours. After the reaction was complete, water was added to the reaction solution and extracted once with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 5:1) to obtain 120 mg of the target product (1a-10) as a white solid.

[0404] Synthesis Example 9: Synthesis of 1-(tert-butyl)-N-((2,4-dimethylbenzyl)oxy)-4-(3-(phenylethynyl)phenoxy)-1H-pyrazole-5-carboxamide (1a-14)

[0405]

[0406] 200 mg of 1-(tert-butyl)-N-((2,4-dimethylbenzyl)oxy)-4-(3-iodophenoxy)-1H-pyrazole-5-carboxamide (1b-2) and 4 mL of 1,4-dioxane were mixed to a solution to which 270 μL of triethylamine, 60 mg of phenylacetylene, 14 mg of palladium chloride ditriphenylphosphine complex, and 7.3 mg of copper iodide were added and the mixture was stirred at 80°C for 15 hours. After the reaction was complete, water was added to the reaction solution and it was extracted once with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 5:1) to obtain 120 mg of the target product (1a-14) as a white solid.

[0407] Synthesis Example 10: Synthesis of 1-(tert-butyl)-N-((2,4-dimethylbenzyl)oxy)-4-(3-(ethynylphenoxy)-N-isobutyryl-1H-pyrazole-5-carboxamide (1a-55) and (Z)-1-(tert-butyl)-N-((2,4-dimethylbenzyl)oxy)-4-(3-ethynylphenoxy)-1H-pyrazole-5-carboxymidic acid isobutyric anhydride (1b-1)

[0408]

[0409] 150 mg of 1-(tert-butyl)-N-((2,4-dimethylbenzyl)oxy)-4-(3-(ethynylphenoxy)-1H-pyrazole-5-carboxamide (1a-2)) and 3.6 mL of dichloromethane were mixed and, under ice cooling, 200 μL of triethylamine and 80 μL of isobutyryl chloride were added. The mixture was stirred at 0°C for 30 minutes, then raised to room temperature and stirred for 15 hours. After the reaction was complete, water was added to the reaction solution and extracted once with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (gradient from n-hexane:ethyl acetate = 20:1 to 10:1) to obtain 20 mg of the target product (1a-55) and 21 mg of the target product (1b-1) as oils.

[0410] <Reference Example> (Method for Producing Intermediate Compounds) A method for producing intermediate compounds for producing the pyrazole compounds or salts thereof of this disclosure is shown as a reference example. The method for producing intermediate compounds is not limited to this.

[0411] Reference Example 1: Synthesis of Compound 3-1 (1-(3-iodophenoxy)propan-2-one)

[0412]

[0413] 15.0 g of 3-iodophenol (2-1), 6.62 g of 1-chloroacetone, and 1.13 g of potassium iodide were dissolved in 90 mL of acetone. The solution was heated under reflux for 14 hours. After the reaction was complete, water was added to the reaction solution and extracted once with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 5:1) to obtain 18.0 g of the target product (3-1) as a pale yellow oily substance.

[0414] Reference Example 2: Synthesis of Compound 4-1 ((E)-4-(dimethylamino)-3-(3-iodophenoxy)buta-3-en-2-one)

[0415]

[0416] 18.0 g of compound (3-1) and 8.12 g of dimethylformamide dimethylacetal were dissolved in 90 mL of toluene. The solution was heated under reflux for 22 hours. After the reaction was complete, water was added to the reaction solution and extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 2:1 to 1:1 gradient) to obtain 8.06 g of the target product (4-1) as a light brown solid.

[0417] Reference Example 3: Synthesis of Compound 5-1 (1-(tert-butyl)-4-(3-iodophenoxy)-5-methyl-1H-pyrazole)

[0418]

[0419] 5.75 g of compound (4-1) and 3.25 g of t-butylhydrazine monohydrate were dissolved in 40 mL of 1,4-dioxane. The solution was refluxed for 14 hours. After the reaction was complete, water was added to the reaction solution and extracted once with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 20:1) to obtain 4.01 g of the target product (5-1) as a white solid.

[0420] Reference Example 4: Synthesis of Compound 6-1 (1-(tert-butyl)-4-(3-iodophenoxy)-1H-pyrazole-5-carboxylic acid)

[0421]

[0422] 1.85 g of compound (5-1) and 1.64 g of potassium permanganate were dissolved in a mixed solution of t-butyl alcohol and water, and the solution was stirred at 100°C for 72 hours. After the reaction was complete, the reaction solution was filtered through Celite, and the Celite was washed with water. The aqueous layer of the obtained filtrate was washed with chloroform, and then a 1 mol / L hydrochloric acid aqueous solution was added until the pH became 1, and the mixture was extracted once with chloroform. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The obtained solid was washed with n-hexane and dried under reduced pressure to obtain 1.03 g of the target product (6-1) as a white solid.

[0423] Reference Example 5: Synthesis of Compound 8-1 ((2,4-dimethylphenyl)methanol)

[0424]

[0425] 23.7 g of 2,4-dimethylbenzaldehyde (7-1) and 3.34 g of sodium borohydride were dissolved in 200 mL of methanol. The solution was reacted at room temperature for 17 hours. After the reaction was complete, water was added to the reaction solution and it was extracted once with ethyl acetate. After the reaction was complete, the reaction solution was concentrated, dilute hydrochloric acid was added, and it was extracted once with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 24.1 g of the target product (8-1). The obtained residue was used in the next reaction without purification.

[0426] Reference Example 6: Synthesis of Compound 9-1 (1-(chloromethyl)-2,4-dimethylbenzene)

[0427]

[0428] 24.1 g of the aforementioned compound (8-1) was dissolved in 42.1 g of thionyl chloride and 200 mL of 1,2-dichloroethane. The solution was refluxed for 32 hours. After the reaction was complete, toluene was added, and the solvent was removed under reduced pressure to obtain 27.4 g of the target product (9-1). The obtained residue was used in the next reaction without purification.

[0429] Reference Example 7: Synthesis of Compound 10-1 (2-((2,4-dimethylbenzyl)oxy)isoindoline-1,3-dione)

[0430]

[0431] 27.4 g of the compound (9-1), 26 g of N-hydroxyphthalimide, 44 g of potassium carbonate, and 2.6 g of potassium iodide were dissolved in 500 mL of acetonitrile. The solution was reacted at room temperature for 114 hours. After the reaction was complete, the residue was concentrated, filtered by Celite, and the solid was washed with water to obtain 55.9 g of the target product (10-1) as a white solid.

[0432] Reference Example 8: Synthesis of Compound 11-1 (O-(2,4-dimethylbenzyl)hydroxylamine)

[0433]

[0434] 44.8 g of the compound (10-1) and 25.5 g of hydrazine monohydrate were dissolved in 500 mL of methanol. The solution was reacted at room temperature for 18 hours. After the reaction was complete, the mixture was filtered through Celite, the mother liquor was concentrated, and the residue was separated by liquid-liquid extraction with dichloromethane and water. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 1:1) to obtain 24.1 g of the target product (11-1) as a yellow oily substance.

[0435] Synthesis Example 11: Synthesis of Compound 1b-3 (1-(tert-butyl)-N-((2,4-dimethylbenzyl)oxy)-4-(3-iodophenoxy)-1H-pyrazole-5-carboxamide)

[0436]

[0437] 1.00 g of compound (6-1), 750 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCl・HCl), 60 mg of N,N-dimethyl-4-aminopyridine (DMAP), and 430 mg of compound (11-1) were dissolved in 9 mL of methylene chloride. The solution was reacted at room temperature for 24 hours. After the reaction was complete, water was added to the reaction solution and extracted once with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 5:1) to obtain 740 mg of the target product (1b-3) as a white solid.

[0438] <Carbonyl bonded type> Reference example 9: Step 1: Synthesis of compound 15 ((E)-3-(dimethylamino)-1-(3-iodophenyl)prop-2-en-1-one)

[0439]

[0440] 3'-iodoacetophenone (14) (5.0 g) was dissolved in 100 mL of toluene, and this was reacted with N,N-dimethylformamide dimethylacetal (17.0 g), followed by heating and stirring for 96 hours. After the reaction, the solvent was removed by distillation, and the residue was purified by silica gel chromatography to obtain 6.0 g of the target product (15) (yield 98%).

[0441] Reference Example 10: Step 2: Synthesis of Compound 16 (ethyl(Z)-4-(dimethylamino)-3-(3-iodobenzoyl)-2-oxobuta-3-enoate)

[0442]

[0443] (E)-3-(dimethylamino)-1-(3-iodophenyl)prop-2-en-1-one (15) (6.0 g) was dissolved in methylene chloride, and ethyl chlorooxoethyl (2.9 g) was reacted at room temperature for 13 hours. After the reaction, the solvent was removed by distillation, and the residue was purified by silica gel chromatography to obtain the target product (16) 7.99 g (yield 99%).

[0444] Reference Example 11: Step 3: Synthesis of Compound 17 (ethyl 1-(tert-butyl)-4-(3-iodobenzoyl)-1H-pyrazole-5-carboxylate)

[0445]

[0446] Ethyl (Z)-4-(dimethylamino)-3-(3-iodobenzoyl)-2-oxobuta-3-enoate (16) (7.99 g) was dissolved in 150 ml of ethanol, tert-butylhydrazine hydrochloride (2.98 g) was added, and the mixture was heated and stirred for 17 hours. The solvent was removed by distillation, and the residue was purified by silica gel chromatography to obtain the target product (17) 6.8 g (yield 80%).

[0447] Reference Example 12: Step 4: Synthesis of Compound 18 (1-(tert-butyl)-4-(3-iodobenzoyl)-1H-pyrazole-5-carboxylic acid)

[0448]

[0449] 1-(tert-butyl)-4-(3-iodobenzoyl)-1H-pyrazole-5-carboxylate (17) (5.44 g) was dissolved in 50 ml of ethanol and 25 ml of water, and the mixture was stirred for 13 hours. After liquid-liquid extraction, the resulting organic layer was washed with saturated saline solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 4.78 g of the target product (18) (yield 94%).

[0450] Synthesis Example 12: Step 5: Synthesis of Compound 1a-b2(1-(tert-butyl)-N-((2-methoxy-4-(5-methyl-1,2,4-oxadiazole-3-yl)benzyl)oxy)-4-(3-trimethylsilylethinylbenzoyl)-1H-pyrazole-5-carboxamide)

[0451]

[0452] To a mixed solution of 1-(tert-butyl)-4-(3-iodobenzoyl)-N-((2-methoxy-4-(5-methyl-1,2,4-oxadiazole-3-yl)benzyl)oxy)-1H-pyrazole-5-carboxamide (1a-b1) (2.0 g) and 11 ml of 1,4-dioxane, triethylamine (1.65 g), trimethylsilylacetylene (390 mg), palladium chloride ditriphenylphosphine complex (230 mg), and copper iodide (70 mg) were added, and the mixture was stirred at room temperature for 15 hours. After the reaction was complete, water was added to the reaction solution, and it was extracted once with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 1.32 g of the target product (1a-b2) (yield 69%).

[0453] Synthesis Example 13: Step 6: Synthesis of Compound 1a-b3(1-(tert-butyl)-4-(3-ethynylbenzoyl)-N-((2-methoxy-4-(5-methyl-1,2,4-oxadiazole-3-yl)benzyl)oxy)-1H-pyrazole-5-carboxamide)

[0454]

[0455] 1.0 g of 1-(tert-butyl)-N-((2-methoxy-4-(5-methyl-1,2,4-oxadiazole-3-yl)benzyl)oxy)-4-(3-trimethylsilylethynylbenzoyl)-1H-pyrazole-5-carboxamide (1a-b2)) and 17 ml of tetrahydrofuran were mixed and 2.6 ml of tetrabutylammonium fluoride (approximately 1 mol / L tetrahydrofuran solution) was added, and the mixture was stirred at room temperature for 15 hours. After the reaction was complete, water was added to the reaction solution and extracted once with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 740 mg of the target product (1a-b3) (yield 84%).

[0456] Synthesis Example 14: Step 7: Synthesis of Compound 1b-b1(methoxymethyl (Z)-1-(tert-butyl)-4-(3-ethynylbenzoyl)-N-((2-methoxy-4-(5-methyl-1,2,4-oxadiazole-3-yl)benzyl)oxy)-1H-pyrazole-5-carbimidate)

[0457]

[0458] 1-(tert-butyl)-4-(3-ethynylbenzoyl)-N-((2-methoxy-4-(5-methyl-1,2,4-oxadiazole-3-yl)benzyl)oxy)-1H-pyrazole-5-carboxamide (1a-b3) (0.15 g), potassium carbonate (0.41 g), and chloromethyl methyl ether (0.12 g) were dissolved in DMF (3.0 ml). This mixture was stirred at room temperature for 17 hours, then water was added to the reaction mixture and extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography to obtain 90 mg of the target product (1b-b1) (yield 55%).

[0459] Synthesis Example 15: Step 8: Synthesis of Compound 1a-b4(N-acetyl-1-(tert-butyl)-4-(3-ethynylbenzoyl)-N-((2-methoxy-4-(5-methyl-1,2,4-oxadiazole-3-yl)benzyl)oxy)-1H-pyrazole-5-carboxamide)

[0460]

[0461] 1-(tert-butyl)-4-(3-ethynylbenzoyl)-N-((2-methoxy-4-(5-methyl-1,2,4-oxadiazole-3-yl)benzyl)oxy)-1H-pyrazole-5-carboxamide (1a-b3) (0.15 g) and acetic anhydride (0.30 g) were dissolved in pyridine (2.0 ml). This mixture was stirred at 60°C for 15 hours, then water was added to the reaction mixture and extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography to obtain 130 mg of the target product (1a-b4) (yield 80%).

[0462] The compounds of this disclosure can be synthesized in accordance with the above-mentioned synthesis examples and reference examples. The compounds shown in Tables 1 to 16 below were synthesized in the same manner as in Synthesis Examples 1 to 16. However, the pyrazole compounds or salts thereof included in this disclosure are not limited to these.

[0463] In this specification, "H" represents a "hydrogen atom," "O" represents an "oxygen atom," the substituent "Me" represents "methyl," and similarly, "Et" represents "ethyl," "tBu" represents "tert-butyl," "nPr" represents "n-propyl," "iPr" represents "isopropyl," "cPr" represents "cyclopropyl," "Ph" represents "phenyl," "TMS" represents "trimethylsilyl," "Bn" represents "benzyl," "Allyl" represents "allyl," the substituent "OMe" represents "methoxy," "F" represents a "fluorine atom," "Cl" represents a "chlorine atom," "Br" represents a "bromine atom," "I" represents "iodine," and "CF ３" represents "trifluoromethyl", "CN" represents "cyano", "CHO" represents "aldehyde", and "NO" represents " ２ " represents "nitro", "Boc" represents "tert-leaf toxic carbonyl", "Bz" represents "benzoyl", "MOM" represents "methoxymethyl", "S" represents "sulfide", and "SO ２ " represents "sulfonyl", "Ac" represents "acyl", "~ (wavy line)" represents geometric isomers, and "*" represents "binding site".

[0464] The medium-pressure preparative liquid chromatography described in the synthesis example was performed using a Yamazen Corporation medium-pressure preparative apparatus; W-prep2XY-10VW (flow rate 30 ml / min, silica gel column 40 μm).

[0465]

[0466]

[0467]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473]

[0474]

[0475] (Physical properties) Proton nuclear magnetic resonance spectrum of NMR 400MHz (model: Ascend Evo400, manufactured by Bruker) (hereinafter, １ The nuclear magnetic resonance spectra of the compounds disclosed herein were measured using an apparatus referred to as ¹H-NMR. Me was used as the reference material. ４ Si (tetramethylsilane) was used. １The symbols in the H-NMR chemical shift values ​​represent the following: s: singlet, d: doublet, dd: double doublet, t: triplet, dt: double triplet, q: quartet, dq: double quartet, sep: septet, m: multiplet, brs: broad singlet, brd: broad doublet. The respective chemical shift values ​​for the compounds disclosed herein are shown in Tables 7 to 12 below.

[0476]

[0477]

[0478]

[0479]

[0480]

[0481]

[0482] Intermediate compound (2B) (benzoyl-linked pyrazole intermediate)

[0483]

[0484]

[0485]

[0486] Intermediate compound (3B) (benzoyl-linked pyrazole intermediate)

[0487]

[0488]

[0489]

[0490] Preparation of Test Solution The disclosed compound was dissolved in acetone to prepare an acetone solution (emulsion) of the disclosed compound. The prepared emulsion was diluted with water, and then diluted with a 2000-fold diluted aqueous solution of Kumiten (registered trademark, hereinafter omitted) so that the pyrazole compound of the disclosed compound was present at 250 ppm. Subsequently, the diluted emulsion was used as the test solution in the following Test Examples 1 to 7.

[0491] Test Example 1: Cucumber Gray Mold Control Test Cucumbers were sprayed with the aforementioned test solution. After air drying, a conidial suspension of cucumber gray mold (Botrytis cinerea) was inoculated by dripping. As a control, cucumbers that were not sprayed with the solution were similarly inoculated with the conidial suspension. These were left standing in a humid chamber. Four days after inoculation, the area of ​​lesions on the cucumber leaves was observed visually, and the control efficacy was calculated.

[0492] Control value = [1 - (lesion area rate in treated area / lesion area rate in untreated area)] x 100

[0493] As a result, among the compounds tested, the following compounds showed a control value of 70% or more. Compounds: 1A-A1-a1, 1A-A1-a2, 1A-A1-a3, 1A-A1-a4, 1A-A1-a5, 1A-A1-a6, 1A-A1-a7, 1A-A1-a8, 1A-A1-a9, 1A-A1-a10, 1A-A1-a11, 1A-A1-a13, 1A-A1-a14, 1A-A1-a15, 1A-A1- a16, 1A-A1-a18, 1A-A1-a19, 1A-A1-a20, 1A-A1-a23, 1A-A1-a24, 1A-A1-a26, 1A-A1- a27, 1A-A1-a29, 1A-A1-a31, 1A-A1-a32, 1A-A1-a33, 1A-A1-a34, 1A-A1-a35, 1A-A1-a 36, 1A-A1-a37, 1A-A1-a38, 1A-A1-a41, 1A-A1-a42, 1A-A1-a43, 1A-A1-a44, 1A-A1-a 45, 1A-A1-a46, 1A-A1-a47, 1A-A1-a48, 1A-A1-a49, 1A-A1-a50, 1A-A1-a51, 1A-A1-a5 2, 1A-A1-a53, 1A-A1-a54, 1A-A1-a55, 1A-A1-a56, 1A-A1-a57, 1A-A1-a58, 1A-A1-a59 , 1A-A1-a60, 1A-A1-a61, 1A-A1-a62, 1A-A1-a63, 1A-A1-a64, 1A-A1-a65, 1A-A1-a66; 1A-A1-b1, 1A-A1-b2, 1A-A1-b3, 1A-A1-b5, 1A-A1-b8, 1A-A1-b10, 1A-A1-b11, 1A-A1- b12, 1A-A1-b14, 1A-A1-b16, 1A-A1-b17, 1A-A1-b19, 1A-A1-b20, 1A-A1-b21, 1A-A1-b 22, 1A-A1-b23, 1A-A1-b24, 1A-A1-b25, 1A-A1-b26, 1A-A1-b27, 1A-A1-b28, 1A-A1-b2 9, 1A-A1-b30, 1A-A1-b31, 1A-A1-b32, 1A-A1-b33, 1A-A1-b34, 1A-A1-b35, 1A-A1-b36; 1A-B1-a1, 1A-B1-a2, 1A-B1-a3, 1A-B1-a4, 1A-B1-a5, 1A-B1-a6, 1A-B1-a7, 1A-B1-a8, 1A-B1-b2;1B-A1-a1、1B-A1-a3、1 B-A1-a7、1B-A1-a10、1B -A1-a11、1B-A1-a13、1 B-A1-a14、1B-A1-a16、1 B-A1-a17、1B-A1-a18、1B-A1-a34、1B-A1-a35、1B-A1-a37、1B-A1-a38、1B-A1-a39、1B-A1-a40 、1B-A1-a41、1B-A1-a4 3、1B-A1-a44、1B-A1-a4 5、1B-A1-a46、1B-A1-a 48、1B-A1-a49、1B-A1-a 50, 1B-A1-51, 1B-A1-52, 1B-A1-53, 1B-A1-54, 1B-A1-55, 1B-A1-56, 1B-A1-57, 1B-A1- a58、1B-A1-a59、1B-A1 -a61、1B-A1-a62、1B-A1 -a65、1B-A1-a66、1B-A 1-a67、1B-A1-a68、1B-A 1-69, 1-A-1-70, 1-A-1-73, 1-A-1-74, 1-A-1-75, 1-A-1-76, 1-A-1-77, 1-A-1-78, 1-A A1-a79、1B-A1-a80、1B -A1-a81、1B-A1-a82、1B -A1-a83、1B-A1-a84、1 B-A1-a85、1B-A1-a86、1 B-A1-a87、1B-A1-a88、 1B-A1-a89、1B-A1-a90、 1B-A1-a91、1B-A1-a94、 1B-A1-a95、1B-A1-a97;1B-A1-b1, 1B-A1-b2, 1B-A1-b3, 1B-A1-b4, 1B-A1-b5, 1B-A1-b6, 1B-A1-b7, 1B-A1-b8 , 1B-A1-b9, 1B-A1-b10, 1B-A1-b11, 1B-A1-b13, 1B-A1-b14, 1B-A1-b15, 1B-A1-b16, 1 B-A1-b17, 1B-A1-b18, 1B-A1-b19, 1B-A1-b20, 1B-A1-b21, 1B-A1-b22, 1B-A1-b23, 1B -A1-b24, 1B-A1-b25, 1B-A1-b26, 1B-A1-b27, 1B-A1-b28, 1B-A1-b29, 1B-A1-b30, 1B-A 1-b31, 1B-A1-b32, 1B-A1-b34, 1B-A1-b35, 1B-A1-b36, 1B-A1-b37, 1B-A1-b38, 1B-A1 -b39, 1B-A1-b40, 1B-A1-b41, 1B-A1-b42, 1B-A1-b43, 1B-A1-b44, 1B-A1-b45, 1B-A1-b 46, 1B-A1-b47, 1B-A1-b48, 1B-A1-b49, 1B-A1-b50, 1B-A1-b51, 1B-A1-b52, 1B-A1-b5 3, 1B-A1-b54, 1B-A1-b55, 1B-A1-b56, 1B-A1-b57, 1B-A1-b58, 1B-A1-b59, 1B-A1-b61; 1B-B1-a2, 1B-B1-a3, 1B-B1-a4, 1B-B1-a7, 1B-B1-a8, 1B-B1-a9, 1B-B1-a10, 1B-B1-a11, 1B-B1-a12, 1B-B1-a13, 1B-B1-b1, 1B-B1-b2, 1B-B1-b3, 1B-B1-b4, 1B-B1-b5, 1B-B1-b6. ;

[0494] Test Example 2: Tomato Ring Spot Disease Pot Test The above test solution was sprayed onto tomato plants. After air drying, a suspension of conidia of tomato ring spot disease (Alternaria solani) was spray-inoculated. As a control, tomatoes that were not sprayed with the solution were similarly inoculated with the conidia suspension. These were left standing in a humid chamber. Four days after inoculation, the area of ​​lesions on the tomato leaves was observed visually, and the control efficacy was calculated.

[0495] Control value = [1 - (lesion area rate in treated area / lesion area rate in untreated area)] x 100

[0496] As a result, among the compounds tested, the following compounds showed a control value of 70% or more. Compounds: 1A-A1-a1, 1A-A1-a2, 1A-A1-a3, 1A-A1-a5, 1A-A1-a8, 1A-A1-a14, 1A-A1-a15, 1A-A1-a16, 1A-A1-a18, 1A-A1-a26, 1A-A1-a27, 1A-A1-a31, 1A-A1-a32, 1A-A1-a33, 1A-A1-a35, 1A-A1-a36, 1A-A1-a37, 1A-A1-a41, 1A-A1-a42, 1A-A1-a44, 1A-A1-a46, 1A-A1-a47, 1A-A1-a48, 1A-A1-a50, 1A-A1-a51, 1A-A1-a52, 1A-A1-a53, 1A-A1-a54, 1A-A1-a55, 1A-A1-a56, 1A-A1-a57, 1A-A1-a58, 1A-A1-a59, 1A-A1-a60, 1A-A1-a61, 1A-A1-a66; 1A-A1-b1, 1A-A1-b2, 1A-A1-b3, 1A-A1-b5, 1A-A1-b8, 1A-A1-b10, 1A- A1-b11, 1A-A1-b12, 1A-A1-b14, 1A-A1-b16, 1A-A1-b19, 1A-A1-b20, 1A -A1-b21, 1A-A1-b22, 1A-A1-b23, 1A-A1-b24, 1A-A1-b25, 1A-A1-b26, 1 A-A1-b27, 1A-A1-b28, 1A-A1-b30, 1A-A1-b32, 1A-A1-b33, 1A-A1-b35; 1A-B1-a1, 1A-B1-a3, 1A-B1-a4, 1A-B1-a7, 1A-B1-a8, 1A-B1-b2; 1B-A1-a38, 1B-A1-a39, 1B-A1-a45, 1B-A1-a50, 1B-A1-a54, 1B-A1-a56, 1B-A1 -a58, 1B-A1-a79, 1B-A1-a80, 1B-A1-a81, 1B-A1-a82, 1B-A1-a83, 1B-A1-a94;1B-A1-b1, 1B-A1-b10, 1B-A1-b11, 1B-A1-b16, 1B-A1-b17, 1B-A1-b18, 1B- A1-b19, 1B-A1-b20, 1B-A1-b21, 1B-A1-b22, 1B-A1-b23, 1B-A1-b24, 1B-A1 -b27, 1B-A1-b29, 1B-A1-b30, 1B-A1-b31, 1B-A1-b35, 1B-A1-b37, 1B-A1-b 38, 1B-A1-b39, 1B-A1-b42, 1B-A1-b45, 1B-A1-b50, 1B-A1-b51, 1B-A1-b56; 1B-B1-a2, 1B-B1-a9, 1B-B1-a10, 1B-B1-a11, 1B-B1-a12, 1B-B1-b1, 1B-B1-b3, 1B-B1-b4. ;

[0497] Test Example 3: Cucumber Sclerotinia Disease Pot Test The test solution was sprayed onto cucumber plants. After air drying, discs with punched-out tips of Sclerotinia sclerotiorum mycelium, which had been pre-cultured on potato dextrose agar, were placed on the cucumber leaves and inoculated. As a control, discs of mycelium were similarly placed on cucumber plants that had not been sprayed with the solution. These were left standing in a humid chamber. Three days after inoculation, the size of the lesions on the cucumber leaves was measured and the control efficacy was calculated.

[0498] Control value = [1 - (diameter of lesion in treated area / diameter of lesion in untreated area)] × 100

[0499] As a result, among the compounds tested, the following compounds showed a control value of 70% or more: Compounds: 1A-A1-a1, 1A-A1-a2, 1A-A1-a3, 1A-A1-a4, 1A-A1-a5, 1A-A1-a6, 1A-A1-a7, 1A-A1-a9, 1A-A1-a10, 1A-A1-a11, 1A-A1-a13, 1A-A1-a15, 1A-A1-a16, 1A-A1-a17, 1A-A1-a18, 1A-A1-a20, 1A-A1-a22, 1A-A1-a24; 1A-A1-b1, 1A-A1-b2, 1A-A1-b3.

[0500] Test Example 4: Cucumber Anthracnose Pot Test The above test solution was sprayed onto cucumber plants. After air drying, a conidial suspension of cucurbit anthracnose (Colletotrichum orbicularea) was spray-inoculated. As a control, cucumber plants that were not sprayed with the solution were similarly inoculated with the conidial suspension. These were left standing in a humid chamber. Seven days after inoculation, the area of ​​lesions on the cucumber leaves was observed visually, and the control efficacy was calculated.

[0501] Control value = [1 - (lesion area rate in treated area / lesion area rate in untreated area)] x 100

[0502] As a result, among the compounds tested, the following compounds showed a control value of 70% or more: Compounds: 1A-A1-a1, 1A-A1-a2, 1A-A1-a3, 1A-A1-a4, 1A-A1-a5, 1A-A1-a6, 1A-A1-a7, 1A-A1-a8, 1A-A1-a9, 1A-A1-a10, 1A-A1-a11, 1A-A1-a13, 1A-A1-a14, 1A-A1-a15, 1A-A1-a16, 1A-A1-a22, 1A-A1-a24; 1A-A1-b1, 1A-A1-b2, 1A-A1-b3.

[0503] Test Example 5: Cucumber Powdery Mildew Test. The test solution was sprayed onto cucumber plants. After air drying, the cucumber powdery mildew conidia suspension was spray-inoculated. As a control, cucumbers that were not sprayed with the solution were similarly inoculated with the conidia suspension. These were left standing in a constant temperature room. Seven days after inoculation, the area of ​​lesions on the cucumber leaves was observed visually, and the control efficacy was calculated.

[0504] Control value = [1 - (lesion area rate in treated area / lesion area rate in untreated area)] x 100

[0505] As a result, among the compounds tested, the following compounds showed a control value of 70% or more: Compounds: 1A-A1-a1, 1A-A1-a2, 1A-A1-a3, 1A-A1-a4, 1A-A1-a5, 1A-A1-a6, 1A-A1-a8, 1A-A1-a9, 1A-A1-a14, 1A-A1-a15, 1A-A1-a16; 1A-A1-b1, 1A-A1-b2, 1A-A1-b3.

[0506] Test Example 6: Antimicrobial activity test against Bottletis cinerea (gray mold fungus) 199 μL of Synthetic defined + 2% glucose + 0.05% sodium acetate liquid medium containing Bottletis cinerea (gray mold fungus) conidia was placed in a 96-well plate. Subsequently, 1 μL of emulsion containing the disclosed compound at 20 ppm was added and mixed. As a control, a conidial suspension medium without the disclosed compound was prepared. These were left standing in a constant temperature room at 20°C. Three days after compound addition, the growth of gray mold fungus was observed.

[0507] As a result, among the compounds tested, the following compounds inhibited bacterial growth by more than 70%. Compounds: 1A-A1-a1, 1A-A1-a2, 1A-A1-a3, 1A-A1-a4, 1A-A1-a5, 1A-A1-a6, 1A-A1-a7, 1A-A1-a8, 1A-A1-a9, 1A-A1-a10, 1A-A1-a11, 1A-A1-a13, 1A-A1-a14, 1A-A1-a15, 1A- A1-a16, 1A-A1-a18, 1A-A1-a20, 1A-A1-a23, 1A-A1-a24, 1A-A1-a26, 1A-A1-a27, 1A -A1-a29, 1A-A1-a31, 1A-A1-a32, 1A-A1-a33, 1A-A1-a34, 1A-A1-a35, 1A-A1-a36, 1A -A1-a37, 1A-A1-a38, 1A-A1-a41, 1A-A1-a42, 1A-A1-a43, 1A-A1-a44, 1A-A1-a45, 1 A-A1-a46, 1A-A1-a47, 1A-A1-a48, 1A-A1-a49, 1A-A1-a50, 1A-A1-a51, 1A-A1-a52, 1 A-A1-a53, 1A-A1-a54, 1A-A1-a55, 1A-A1-a56, 1A-A1-a57, 1A-A1-a58, 1A-A1-a59, 1A-A1-a60, 1A-A1-a61, 1A-A1-a62, 1A-A1-a63, 1A-A1-a64, 1A-A1-a65, 1A-A1-a66; 1A-A1-b1, 1A-A1-b2, 1A-A1-b3, 1A-A1-b5, 1A-A1-b6, 1A-A1-b8, 1A-A1-b10, 1A-A1-b 11, 1A-A1-b12, 1A-A1-b14, 1A-A1-b16, 1A-A1-b17, 1A-A1-b18, 1A-A1-b19, 1A-A1-b2 0, 1A-A1-b21, 1A-A1-b22, 1A-A1-b23, 1A-A1-b24, 1A-A1-b25, 1A-A1-b26, 1A-A1-b27 , 1A-A1-b28, 1A-A1-b30, 1A-A1-b31, 1A-A1-b32, 1A-A1-b33, 1A-A1-b35, 1A-A1-b38; 1A-B1-a1, 1A-B1-a3, 1A-B1-a4, 1A-B1-a5, 1A-B1-a6, 1A-B1-a7, 1A-B1-a8, 1A-B1-b1, 1A-B1-b2;1-A-1-1, 1-A-1-2, 1-A-1-3, 1-A-1-7, 1-A-1-10, 1-A-1-11, 1-A-1-13, 1-A-1-4, 1-A 1-a16、1B-A1-a17、1B-A 1-a18、1B-A1-a19、1B-A 1-a28、1B-A1-a34、1B-A 1-a35、1B-A1-a37、1B-A1 -a38、1B-A1-a39、1B-A1 -a40、1B-A1-a41、1B-A1 -a43、1B-A1-a44、1B-A1 -a45、1B-A1-a46、1B-A1- a48、1B-A1-a49、1B-A1-a50、1B-A1-a51、1B-A1-a52、1B-A1-a53、1B-A1-a54、1B-A1-a55、1B-A1-a 56、1B-A1-a57、1B-A1-a 58、1B-A1-a59、1B-A1-a 61、1B-A1-a67、1B-A1-a 68、1B-A1-a69、1B-A1-a 70, 1B-A1-73, 1B-A1-74, 1B-A1-75, 1B-A1-76, 1B-A1-77, 1B-A1-78, 1B-A1-79, 1B-A1-8 0、1B-A1-a81、1B-A1-a8 2、1B-A1-a83、1B-A1-a8 4、1B-A1-a85、1B-A1-a8 6、1B-A1-a87、1B-A1-a88 、1B-A1-a89、1B-A1-a90、1B-A1-a91、1B-A1-a93、1B-A1-a94、1B-A1-a95、1B-A1-a96、1B-A1-a97;1B-A1-b1, 1B-A1-b2, 1B-A1-b3, 1B-A1-b6, 1B-A1-b8, 1B-A1-b10, 1B-A1-b11, 1B-A1-b13, 1B-A1-b14, 1B-A1-b15, 1B-A1-b16, 1B-A1-b17, 1B-A1-b18, 1B-A1- b19, 1B-A1-b20, 1B-A1-b21, 1B-A1-b22, 1B-A1-b23, 1B-A1-b24, 1B-A1-b25, 1 B-A1-b26, 1B-A1-b27, 1B-A1-b28, 1B-A1-b29, 1B-A1-b30, 1B-A1-b31, 1B-A1-b 32, 1B-A1-b34, 1B-A1-b35, 1B-A1-b36, 1B-A1-b37, 1B-A1-b38, 1B-A1-b39, 1B -A1-b40, 1B-A1-b41, 1B-A1-b42, 1B-A1-b43, 1B-A1-b44, 1B-A1-b45, 1B-A1-b4 6, 1B-A1-b47, 1B-A1-b48, 1B-A1-b49, 1B-A1-b50, 1B-A1-b51, 1B-A1-b52, 1B-A 1-b53, 1B-A1-b54, 1B-A1-b55, 1B-A1-b56, 1B-A1-b57, 1B-A1-b59, 1B-A1-b61; 1B-B1-a2, 1B-B1-a3, 1B-B1-a4, 1B-B1-a8, 1B-B1-a9, 1B-B1-a10, 1B-B1-a11, 1B-B 1-a12, 1B-B1-a13, 1B-B1-b1, 1B-B1-b2, 1B-B1-b3, 1B-B1-b4, 1B-B1-b5, 1B-B1-b6. ;

[0508] Test Example 7: Antimicrobial activity test against Venturia inaequaris (apple scab fungus) 199 μL of Synthetic defined + 2% glucose + 0.05% sodium acetate liquid medium containing Venturia inaequaris (apple scab fungus) conidia was added to a 96-well plate. Subsequently, 1 μL of emulsion containing the disclosed compound at 20 ppm was added and mixed. As a control, a conidial suspension medium without the disclosed compound was prepared. These were left standing in a constant temperature room at 20°C. Three days after compound addition, the growth of apple scab fungus was observed.

[0509] As a result, among the compounds tested, the following compounds showed a control value of 70% or more. Compounds: 1A-A1-a1, 1A-A1-a2, 1A-A1-a3, 1A-A1-a4, 1A-A1-a5, 1A-A1-a8, 1A-A1-a10, 1A-A1-a11, 1A-A1-a14, 1A-A1-a15, 1A-A1-a16, 1A-A1-a18, 1A-A1-a23, 1A-A1-a24, 1A-A1-a27, 1A-A1-a31, 1A-A1-a33, 1A-A1-a35, 1A-A1-a36, 1A-A1-a37, 1A-A1-a41, 1A-A1- a42, 1A-A1-a43, 1A-A1-a44, 1A-A1-a45, 1A-A1-a46, 1A-A1-a47, 1A-A1-a48, 1A-A1-a49, 1A-A1-a50, 1A-A1-a51, 1A-A1-a52, 1A- A1-a53, 1A-A1-a54, 1A-A1-a55, 1A-A1-a56, 1A-A1-a57, 1A-A1-a58, 1A-A1-a59, 1A-A1-a60, 1A-A1-a61, 1A-A1-a62, 1A-A1-a66; 1A-A1-b1, 1A-A1-b2, 1A-A1-b3, 1A-A1-b5, 1A-A1-b10, 1A-A1-b11, 1A-A1 -b12, 1A-A1-b14, 1A-A1-b16, 1A-A1-b17, 1A-A1-b18, 1A-A1-b19, 1A-A1-b 20, 1A-A1-b21, 1A-A1-b22, 1A-A1-b23, 1A-A1-b24, 1A-A1-b25, 1A-A1-b2 6, 1A-A1-b28, 1A-A1-b30, 1A-A1-b32, 1A-A1-b33, 1A-A1-b35, 1A-A1-b38; 1A-B1-a3, 1A-B1-a4, 1A-B1-a5, 1A-B1-a7, 1A-B1-a8, 1A-B1-b2;1B-A1-a17, 1B-A1-a18, 1B-A1-a38, 1B-A1-a39, 1B-A1-a40, 1B-A1-a45, 1B-A1 -a46, 1B-A1-a48, 1B-A1-a49, 1B-A1-a50, 1B-A1-a53, 1B-A1-a54, 1B-A1-a56, 1B-A1-a57, 1B-A1-a58, 1B-A1-a68, 1B-A1-a74, 1B-A1-a79, 1B-A1-a80, 1B-A1 -a81, 1B-A1-a82, 1B-A1-a83, 1B-A1-a84, 1B-A1-a94, 1B-A1-a95, 1B-A1-a96; 1B-A1-b1, 1B-A1-b2, 1B-A1-b3, 1B-A1-b6, 1B-A1-b10, 1B-A1-b11, 1B-A1-b14, 1B-A1-b15, 1B-A1-b16, 1B-A1-b17, 1B- A1-b18, 1B-A1-b19, 1B-A1-b20, 1B-A1-b21, 1B-A1-b22, 1B-A1-b23, 1B-A1-b24, 1B-A1-b26, 1B-A1-b27, 1B-A1-b28, 1B -A1-b29, 1B-A1-b30, 1B-A1-b31, 1B-A1-b35, 1B-A1-b37, 1B-A1-b38, 1B-A1-b39, 1B-A1-b40, 1B-A1-b41, 1B-A1-b42, 1 B-A1-b43, 1B-A1-b45, 1B-A1-b46, 1B-A1-b47, 1B-A1-b50, 1B-A1-b51, 1B-A1-b52, 1B-A1-b53, 1B-A1-b57, 1B-A1-b59; 1B-B1-a2, 1B-B1-a4, 1B-B1-a9, 1B-B1-a10, 1B-B1-a11, 1B-B1-a12, 1B-B1-a13, 1B-B1-b1, 1B-B1-b2, 1B-B1-b3, 1B-B1-b4, 1B-B1-b5. ;

[0510] This application is based on a Japanese patent application, Japanese Patent Application No. 2024-230535, filed on December 26, 2024. Japanese Patent Application No. 2024-230535 is incorporated herein by reference.

Claims

1. General formula (1): (In the formula, A represents iodine, optionally substituted alkynyl, substituted alkenyl, substituted cycloalkyl, formyl, or optionally substituted heterocyclic group. Z represents optionally substituted divalent carbocyclic group or optionally substituted divalent heterocyclic group. X represents an oxygen atom or carbonyl (C=O). T represents an oxygen atom or sulfur atom. L represents optionally substituted alkyl, optionally substituted carbocyclic, optionally substituted heterocyclic group, optionally substituted alkoxy, optionally substituted cycloalkoxy, optionally substituted aryloxy, or optionally substituted heteroaryloxy. １ R represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted carbon ring, or an optionally substituted heterocycle. ２ R represents a hydrogen atom, a halogen atom, an optionally substituted alkyl group, or an optionally substituted alkoxy group. ３ (where represents a hydrogen atom, an optionally substituted alkyl, an optionally substituted alkoxy, an optionally substituted acyl, an optionally substituted alkoxycarbonyl, or an optionally substituted sulfonyl.) A pyrazole compound represented by ), its structural isomer, or salts thereof.

2. The pyrazole compound represented by the general formula (1), its structural isomer, or a salt thereof is a compound represented by the following general formula (1-A) or a compound represented by the following general formula (1-B). The pyrazole compound, its structural isomer, or a salt thereof according to claim 1. (In the formula, R ３Ａ represents a hydrogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an acyl group which may have a substituent, an alkoxycarbonyl group which may have a substituent, or a sulfonyl group which may have a substituent. R ３Ｂ represents a hydrogen atom, an alkyl group which may have a substituent, an acyl group which may have a substituent, an alkoxycarbonyl group which may have a substituent, or a sulfonyl group which may have a substituent. T １ represents an oxygen atom or a sulfur atom. T ２ represents an oxygen atom or a sulfur atom. The wavy line represents the E configuration or Z configuration of the geometric isomer. The A, Z, X, L, R １ , and R ２ are the same as above.) 3. The pyrazole compound according to claim 2, a structural isomer thereof, or a salt thereof, wherein X is an oxygen atom.

4. The pyrazole compound according to claim 2, a structural isomer thereof, or a salt thereof, wherein X is a carbonyl (C=O) group.

5. The pyrazole compound represented by the general formula (1), its structural isomer, or a salt thereof according to claim 2, wherein the pyrazole compound represented by the general formula (1), its structural isomer, or a salt thereof is an ether-type pyrazole compound represented by the following general formula (1A-A1), an ether-type pyrazole compound represented by the following general formula (1A-B1), a carbonyl-type pyrazole compound represented by the following general formula (1B-A1), or a carbonyl-type pyrazole compound represented by the following general formula (1B-B1). (In the formula, R Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , and R Ａ５ These are the same or different hydrogen atoms, hydroxyl, formyl, nitro, cyano, halogen atoms, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted alkylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted amino, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted cycloalkylaminocarbonyl, optionally substituted aminocarbonyl, -C(=NOR ６ ) R ７ The group represented by R is a silyl which may have a substituent, a carbon ring which may have a substituent, or a heterocycle which may have a substituent. ６ R represents a hydrogen atom or an alkyl group which may have a substituent. ７ R represents an alkyl group which may have substituents. However, R Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , and R Ａ５ Of these, at least one represents iodine, optionally substituted alkynyl, substituted alkenyl, substituted cycloalkyl, formyl, or optionally substituted heterocycle. １ , T ２ , L, R １ , R ２ , R ３Ａ , and R ３Ｂ (This is the same as above.) 6. The pyrazole compound, structural isomer thereof, or salt thereof according to claim 2, wherein the pyrazole compound represented by the general formula (1), its structural isomer, or salt thereof is an ether-type pyrazole compound represented by the following general formula (1A-A2), an ether-type pyrazole compound represented by the following general formula (1A-B2), a carbonyl-type pyrazole compound represented by the following general formula (1B-A2), or a carbonyl-type pyrazole compound represented by the following general formula (1B-B2). (In the formula, L １ is an oxygen atom, or -C(R) Ｌ１ ) (Caution Ｌ２ ) indicates the R Ｌ１ and R Ｌ２ R represents the same or different hydrogen atom or an alkyl group which may have a substituent. Ｌ１ and R Ｌ２ These two groups may bond to each other with adjacent carbon atoms to form a saturated or unsaturated carbon ring. The saturated or unsaturated carbon ring may further have substituents. ４ and R ５ R represents, either identically or differently, a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group, or an optionally substituted heterocycle. ４ and R ５ These two groups may bond to each other with adjacent carbon atoms to form a saturated or unsaturated carbon ring. The saturated or unsaturated carbon ring may further have substituents. p represents an integer from 0 to 3. When p is 2 or 3, the two or three R ４ These may be the same or different, and the two or three R's mentioned above are... ５ They may be the same or different. Ｂ１ , R Ｂ２ , R Ｂ３ , R Ｂ４ , and R Ｂ５ These are the same or different hydrogen atoms, hydroxyl, formyl, nitro, cyano, halogen atoms, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted alkylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted amino, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted cycloalkylaminocarbonyl, optionally substituted aminocarbonyl, -C(=NOR ６ ) R ７ The group represented by R is a silyl which may have a substituent, a carbon ring which may have a substituent, or a heterocycle which may have a substituent. ６ R represents a hydrogen atom or an alkyl group which may have a substituent. ７ R represents an alkyl group which may have substituents. Ａ１ , R Ａ２ , R Ａ３ , R Ａ４ , R Ａ５ , T １ , T ２ , R １ , R ２ , R ３Ａ , and R ３Ｂ (This is the same as above.) 7. The aforementioned R １ The pyrazole compound according to claim 1, a structural isomer thereof, or a salt thereof, wherein the alkyl group may have substituents.

8. The aforementioned R ２ The pyrazole compound according to claim 1, its structural isomer, or a salt thereof, wherein the isomer is a hydrogen atom.

9. The pyrazole compound according to claim 1, a structural isomer thereof, or a salt thereof, wherein A is an alkynyl which may have a substituent.

10. The pyrazole compound according to claim 1, a structural isomer thereof, or a salt thereof, wherein A is iodine.

11. Said L １ The pyrazole compound according to claim 6, its structural isomer, or a salt thereof, wherein the atom is an oxygen atom.

12. Said L １ However, -C(R Ｌ１ ) (Caution Ｌ２ ) - the pyrazole compound according to claim 6, a structural isomer thereof, or a salt thereof.

13. The pyrazole compound according to claim 6, a structural isomer thereof, or a salt thereof, wherein p is 1 or 2.

14. A pesticide containing one or more selected from the pyrazole compound described in any one of claims 1 to 13, its structural isomer, or salts thereof as an active ingredient.

15. A bactericide containing one or more selected from the pyrazole compound described in any one of claims 1 to 13, its structural isomer, or salts thereof as an active ingredient.

16. An intermediate compound for producing a pyrazole compound according to any one of claims 1 to 13, a structural isomer thereof, or a salt thereof, wherein the general formula is (2B): (In the formula, A represents iodine, optionally substituted alkynyl, substituted alkenyl, substituted cycloalkyl, formyl, or optionally substituted heterocyclic group. Z represents optionally substituted divalent carbocyclic group or optionally substituted divalent heterocyclic group. R Ｘ１ R represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted carbon ring, or an optionally substituted heterocycle. １ R represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted carbon ring, or an optionally substituted heterocycle. ２ An intermediate compound represented by (where represents a hydrogen atom, a halogen atom, an optionally substituted alkyl, or an optionally substituted alkoxy).

17. An intermediate compound for producing a pyrazole compound according to any one of claims 1 to 13, a structural isomer thereof, or a salt thereof, wherein the following general formula (3B): (In the formula, A represents iodine, optionally substituted alkynyl, substituted alkenyl, substituted cycloalkyl, formyl, or optionally substituted heterocyclic group. Z represents optionally substituted divalent carbocyclic group or optionally substituted divalent heterocyclic group. R Ｘ１ R represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted carbon ring, or an optionally substituted heterocycle. Ｘ２ and R Ｘ３ An intermediate compound represented by ) which is the same or different alkyl, optionally substituted, optionally substituted carbon ring, or optionally substituted heterocycle.

Images