WO2023063168A1

WO2023063168A1 - Pest controlling composition

Info

Publication number: WO2023063168A1
Application number: PCT/JP2022/037122
Authority: WO
Inventors: 秀幸池内; 昭佳山内; 洋介岸川
Original assignee: ダイキン工業株式会社
Priority date: 2021-10-13
Filing date: 2022-10-04
Publication date: 2023-04-20
Also published as: JP2023162342A; JP7381913B2; JP2023058314A

Abstract

The present invention addresses the problem of providing a composition useful for controlling pests. Disclosed is a pest controlling composition comprising a compound represented by formula (1) (in the formula: R1 and R2 independently represent hydrogen, a hydrocarbon group optionally having one or more substituents, R3CO- or a sulfamoyl group, wherein R3 represents a hydrocarbon group optionally having one or more substituents; X represents hydrogen, a halogen, a nitro group, a cyano group, a hydrocarbon group optionally having one or more substituents, a heteroaryl group, R4O-, R5S- or R6R7N-, wherein R4, R5, R6 and R7 independently represent hydrogen or a hydrocarbon group optionally having one or more substituents; and Z represents hydrogen, a halogen, an azide group, a cyano group or R8O-, wherein R8 represents a hydrocarbon group optionally having one or more substituents) or a salt thereof.

Description

pest control composition

The present disclosure primarily relates to pest control compositions.

Clofarabine is a second-generation purine antagonist classified as a nucleic acid analog antimetabolite. Clofarabine is converted to active clofarabine triphosphate by intracellular enzymes, and by inhibiting both ribonucleotide reductase and DNA polymerase α, it inhibits DNA synthesis and repair in leukemia cells. induce death. Evoltra (trademark) intravenous infusion 20 mg containing clofarabine as an active ingredient has been developed, and its manufacture and sale has been approved for its efficacy in treating "relapsed or refractory acute lymphocytic leukemia" (Non-Patent Document 1).

An object of the present disclosure is to provide a composition useful for controlling pests.

The present disclosure includes the following aspects.
Section 1.
Formula (1) below:

(In the formula,
R ¹ and R ² are each independently hydrogen, a hydrocarbon group optionally having one or more substituents, R ³ CO—, or a sulfamoyl group;
R ³ is a hydrocarbon group optionally having one or more substituents,
X is hydrogen, halogen, nitro group, cyano group, hydrocarbon group optionally having one or more substituents, heteroaryl group, R ⁴ O—, R ⁵ S—, or R ⁶ R ⁷ N - and
R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently hydrogen or a hydrocarbon group optionally having one or more substituents,
Z is hydrogen, halogen, an azide group, a cyano group, or R ⁸ O—;
R ⁸ is a hydrocarbon group optionally having one or more substituents. )
A pest control composition containing a compound represented by or a salt thereof.
Section 2.
Item 2. The pest control composition according to Item 1, wherein R ¹ and R ² are each independently hydrogen or R ³ CO-.
Item 3.
Item ^3. The pest control composition according to Item 1 or 2, wherein R3 is an alkyl group optionally having one or more substituents.
Section 4.
X is hydrogen, halogen, nitro group, cyano group, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, aryl group, heteroaryl group, R ⁴ O—, R ⁵ S—, or R ⁶ R ⁷ N— and
R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently hydrogen or an alkyl group optionally having one or more substituents;
Item 4. The pest control composition according to any one of items 1 to 3.
Item 5.
Item 5. The pest control composition according to any one of Items 1 to 4, wherein X is a halogen, a cyano group, or R ⁴ O-.
Item 6.
Item 6. The pest control composition according to any one of Items 1 to 5, wherein X is fluorine, chlorine, or bromine.
Item 7.
Item 7. The pest control composition according to any one of Items 1 to 6, wherein Z is a halogen.
Item 8.
Item 8. The pest control composition according to any one of Items 1 to 7, wherein Z is fluorine.
Item 9.
Item 9. The pest control composition according to any one of items 1 to 8, wherein the pest is a plant pest or pathogen.
Item 10.
Item 10. The pest control composition according to Item 9, wherein the plant is at least one selected from the group consisting of gramineous plants, cruciferous plants, cucurbitaceous plants, leguminous plants, rosaceous plants, and vine plants. .
Item 11.
Item 11. The pest according to any one of Items 1 to 10, wherein the pest is at least one selected from the group consisting of lepidopteran pests, hemiptera pests, rice blast pathogens, sheath blight pathogens, anthrax pathogens, and brown spot pathogens. A pest control composition as described.
Item 12.
Item 12. The pest control composition according to any one of items 1 to 11, which is applied directly to plants or applied to soil in which plants are grown.
Item 13.
Formula (1a) below:

(In the formula,
R ^1a and R ^2a are each independently a hydrocarbon group optionally having one or more substituents, R ^3a CO—, or a sulfamoyl group,
R ^3a is a hydrocarbon group optionally having one or more substituents,
X ^a is a halogen, a nitro group, a cyano group, a hydrocarbon group optionally having one or more substituents, a heteroaryl group, R ^4a O—, or R ^5a S—;
R ^4a and R ^5a are each hydrogen or a hydrocarbon group optionally having one or more substituents,
Z ^a is a halogen, an azide group, a cyano group, or R ^8a O—;
R ^8a is a hydrocarbon group optionally having one or more substituents. )
A compound represented by or a salt thereof.

According to the present disclosure, compositions useful for controlling pests, for example, are provided.

The above summary of the present disclosure is not intended to describe each disclosed embodiment or every implementation of the present disclosure. The ensuing description of this disclosure more particularly exemplifies illustrative embodiments.

In several places of this disclosure, guidance is provided through examples, and the examples can be used in various combinations. In each case, the exemplary group can serve as a non-exclusive and representative group.

All publications, patents and patent applications cited herein are hereby incorporated by reference as is.

1. Terms The symbols and abbreviations used in the present specification can be understood to have meanings commonly used in the technical field to which the present disclosure belongs, in accordance with the context of the present specification, unless otherwise specified.

In this specification, the phrase "contains" is intended to include the phrase "consisting essentially of" and the phrase "consisting of".

Unless otherwise specified, the steps, treatments, or operations described herein may be performed at room temperature. Herein room temperature can mean a temperature within the range of 10-40°C.

In this specification, the notation “C _nm ” (where n and m are each positive integers and n<m) means that the number of carbon atoms is It represents n or more and m or less.

As used herein, the term "hydrocarbon group" means a group consisting only of carbon and hydrogen. Examples of the "hydrocarbon group" include (1) an aliphatic hydrocarbon group optionally substituted with one or more aromatic hydrocarbon groups (aryl groups), and (2) one or more aliphatic hydrocarbon Aromatic hydrocarbon groups optionally substituted with groups are included.

A "hydrocarbon group" can have a structure that is linear, branched, cyclic, or a combination thereof.

As used herein, the "aliphatic hydrocarbon group" can be saturated or unsaturated. Examples of "aliphatic hydrocarbon groups" include alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, and cycloalkenyl groups.

As used herein, examples of the "alkyl group" include linear or branched C _1-12 alkyl groups, and specific examples thereof include methyl, ethyl, and propyl groups (eg, n- propyl group, isopropyl group), butyl group (eg n-butyl group, isobutyl group, sec-butyl group, tert-butyl group), pentyl group (eg n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group), hexyl group, heptyl group, octyl group, nonyl group, and decyl group.

As used herein, examples of “alkenyl group” include linear or branched C _2-10 alkenyl groups, and specific examples thereof include vinyl, 1-propenyl, isopropenyl, 2 -methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 2-ethyl-1-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl 4-methyl-3-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, and 5-hexenyl groups.

As used herein, examples of "alkynyl group" include linear or branched C _2-10 alkynyl groups, and specific examples thereof include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-hexynyl group, 2-hexynyl group, 3-hexynyl group, 4-hexynyl groups and 5-hexynyl groups are included.

As used herein, examples of “cycloalkyl group” include C _3-10 cycloalkyl groups, and specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and adamantyl groups.

As used herein, examples of "cycloalkenyl groups" include C _3-10 cycloalkenyl groups, and specific examples thereof include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, and cycloheptenyl groups. contain.

As used herein, an "aromatic hydrocarbon group (aryl group)" can be, for example, monocyclic, bicyclic, tricyclic, or tetracyclic. Examples of “aromatic hydrocarbon group” include C _6-14 aromatic hydrocarbon groups, and specific examples thereof include phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3- It includes biphenyl groups, 4-biphenyl groups, and 2-anthryl groups.

In the present specification, examples of the aliphatic hydrocarbon group substituted with the aromatic hydrocarbon group include arylalkyl groups (aralkyl groups), and specific examples thereof include benzyl group, phenethyl group, diphenylmethyl group, 1-naphthylmethyl group, 2-naphthylmethyl group, 2,2-diphenylethyl group, 3-phenylpropyl group, 4-phenylbutyl group, 5-phenylpentyl group, 2-biphenylmethyl group, 3-biphenylmethyl and C _7-15 aralkyl groups such as the 4-biphenylmethyl group.

In this specification, examples of substituents that can be substituted on hydrocarbon groups include halogens, hydroxyl groups, mercapto groups, amino groups, alkoxy groups, alkylthio groups, monoalkylamino groups, and dialkylamino groups.

Examples of "halogen" in this specification include fluorine, chlorine, bromine, and iodine.

As used herein, the "alkoxy group" can be a group represented by RO-- (wherein R is an alkyl group). Examples of "alkoxy group" include linear or branched C _1-12 alkoxy group, and specific examples thereof include methoxy group, ethoxy group, propoxy group (e.g. n-propoxy group, isopropoxy group ), butoxy, pentyloxy, and hexyloxy groups.

In the present specification, the "alkylthio group" can be a group represented by RS- (wherein R is an alkyl group). Examples of "alkylthio group" include linear or branched C _1-12 alkylthio groups, and specific examples thereof include methylthio, ethylthio, propylthio (e.g. n-propylthio, isopropylthio ), butylthio, pentylthio, and hexylthio groups.

As used herein, a "monoalkylamino group" can be a group represented by R-NH- (wherein R is an alkyl group). Examples of "monoalkylamino group" include monolinear or branched C _1-12 alkylamino groups, and specific examples thereof include monomethylamino group, monoethylamino group, monopropylamino group (e.g. : mono n-propylamino group, monoisopropylamino group), and monobutylamino group.

As used herein, a "dialkylamino group" can be a group represented by R ₂ N-- (in the formula, each of the two R's is independently an alkyl group). Examples of "dialkylamino group" include dilinear or branched C _1-12 alkylamino groups, and specific examples thereof are dimethylamino group, diethylamino group, ethylmethylamino group, dipropylamino group (eg, di-n-propylamino group, diisopropylamino group) and methylpropylamino group (eg, methyl n-propylamino group, methylisopropylamino group).

As used herein, the “aromatic heterocyclic group (heteroaryl group)” can be, for example, monocyclic, bicyclic, tricyclic, or tetracyclic, and has 5 to 18 members, 5 to 16 5-14 membered, or 5-12 membered. Examples of the “aromatic heterocyclic group” include 5- or 6-membered monocyclic aromatic heterocyclic groups and 5- to 18-membered aromatic condensed heterocyclic groups.

In the present specification, examples of the "5- or 6-membered monocyclic aromatic heterocyclic group" include a pyrrolyl group (eg, 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group), a furyl group (eg: 2-furyl group, 3-furyl group), thienyl group (e.g. 2-thienyl group, 3-thienyl group), pyrazolyl group (e.g. 1-pyrazolyl group, 3-pyrazolyl group, 4-pyrazolyl group), imidazolyl group (Example: 1-imidazolyl group, 2-imidazolyl group, 4-imidazolyl group), isoxazolyl group (example: 3-isoxazolyl group, 4-isoxazolyl group, 5-isoxazolyl group), oxazolyl group (example: 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group), isothiazolyl group (e.g. 3-isothiazolyl group, 4-isothiazolyl group, 5-isothiazolyl group), thiazolyl group (e.g. 2-thiazolyl group, 4-thiazolyl group, 5-thiazolyl group), triazolyl group (e.g. 1,2,3-triazol-4-yl group, 1,2,4-triazol-3-yl group), oxadiazolyl group (e.g. 1,2,4-oxadiazol- 3-yl group, 1,2,4-oxadiazol-5-yl group), thiadiazolyl group (e.g. 1,2,4-thiadiazol-3-yl group, 1,2,4-thiadiazol-5-yl group), tetrazolyl group, pyridyl group (e.g., 2-pyridyl group, 3-pyridyl group, 4-pyridyl group), pyridazinyl group (e.g., 3-pyridazinyl group, 4-pyridazinyl group), pyrimidinyl group (e.g., 2- pyrimidinyl group, 4-pyrimidinyl group, 5-pyrimidinyl group), and pyrazinyl group.

In the present specification, examples of the "5- to 18-membered aromatic condensed heterocyclic group" include isoindolyl groups (e.g., 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group), indolyl group (e.g. 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7- indolyl group), benzo[b]furanyl group (e.g. 2-benzo[b]furanyl group, 3-benzo[b]furanyl group, 4-benzo[b]furanyl group, 5-benzo[b]furanyl group, 6 -benzo[b]furanyl group, 7-benzo[b]furanyl group), benzo[c]furanyl group (e.g. 1-benzo[c]furanyl group, 4-benzo[c]furanyl group, 5-benzo[c ]furanyl group), benzo[b]thienyl group, (e.g. 2-benzo[b]thienyl group, 3-benzo[b]thienyl group, 4-benzo[b]thienyl group, 5-benzo[b]thienyl group , 6-benzo[b]thienyl group, 7-benzo[b]thienyl group), benzo[c]thienyl group (e.g. 1-benzo[c]thienyl group, 4-benzo[c]thienyl group, 5-benzo [c] thienyl group), indazolyl group (e.g., 1-indazolyl group, 2-indazolyl group, 3-indazolyl group, 4-indazolyl group, 5-indazolyl group, 6-indazolyl group, 7-indazolyl group), benzimidazolyl group (e.g. 1-benzimidazolyl group, 2-benzimidazolyl group, 4-benzimidazolyl group, 5-benzimidazolyl group), 1,2-benzisoxazolyl group (e.g. 1,2-benzisoxazol-3-yl group, 1,2-benzisoxazol-4-yl group, 1,2-benzisoxazol-5-yl group, 1,2-benzisoxazol-6-yl group, 1,2-benzisoxazol-7-yl group), benzoxazolyl group (e.g. 2-benzoxazolyl group, 4-benzoxazolyl group, 5-benzoxazolyl group, 6-benzoxazolyl group, 7-benzoxazolyl group ), 1,2-benzisothiazolyl group (e.g., 1,2-benzisothiazol-3-yl group, 1,2-benzisothiazol-4-yl group, 1,2-benzisothiazol-5- yl group, 1,2-benzisothiazol-6-yl group, 1,2-benzisothiazol-7-yl group), benzothiazolyl group (e.g., 2-benzothiazolyl group, 4-benzothiazolyl group, 5-benzothiazolyl group, 6-benzothiazolyl group, 7-benzothiazolyl group), isoquinolyl group (e.g. 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group), quinolyl group (e.g. 2-quinolyl group, 3-quinolyl group) group, 4-quinolyl group, 5-quinolyl group, 8-quinolyl group), cinnolinyl group (e.g., 3-cinnolinyl group, 4-cinnolinyl group, 5-cinnolinyl group, 6-cinnolinyl group, 7-cinnolinyl group, 8- cinnolinyl group), phthalazinyl group (e.g. 1-phthalazinyl group, 4-phthalazinyl group, 5-phthalazinyl group, 6-phthalazinyl group, 7-phthalazinyl group, 8-phthalazinyl group), quinazolinyl group (e.g. 2-quinazolinyl group, 4-quinazolinyl group, 5-quinazolinyl group, 6-quinazolinyl group, 7-quinazolinyl group, 8-quinazolinyl group), quinoxalinyl group (e.g., 2-quinoxalinyl group, 3-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl group , 7-quinoxalinyl group, 8-quinoxalinyl group), pyrazolo[1,5-a]pyridyl group (e.g., pyrazolo[1,5-a]pyridin-2-yl group, pyrazolo[1,5-a]pyridine- 3-yl group, pyrazolo[1,5-a]pyridin-4-yl group, pyrazolo[1,5-a]pyridin-5-yl group, pyrazolo[1,5-a]pyridin-6-yl group, pyrazolo[1,5-a]pyridin-7-yl group), imidazo[1,2-a]pyridyl group (e.g. imidazo[1,2-a]pyridin-2-yl group, imidazo[1,2- a]pyridin-3-yl group, imidazo[1,2-a]pyridin-5-yl group, imidazo[1,2-a]pyridin-6-yl group, imidazo[1,2-a]pyridine-7 -yl group, and imidazo[1,2-a]pyridin-8-yl group).

2. Pest control composition The pest control composition of the present disclosure has the following formula (1):

(In the formula,
R ¹ and R ² are each independently hydrogen, a hydrocarbon group optionally having one or more substituents, R ³ CO—, or a sulfamoyl group (H ₂ N—SO ₂ —); ,
R ³ is a hydrocarbon group optionally having one or more substituents,
X is hydrogen, halogen, nitro group, cyano group, hydrocarbon group optionally having one or more substituents, heteroaryl group, R ⁴ O—, R ⁵ S—, or R ⁶ R ⁷ N - and
R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently hydrogen or a hydrocarbon group optionally having one or more substituents,
Z is hydrogen, halogen, an azide group (-N=N ⁺ =N ^- ), a cyano group, or R ⁸ O-;
R ⁸ is a hydrocarbon group optionally having one or more substituents. )
Contains a compound represented by or a salt thereof.

In one embodiment, R ¹ and R ² are each independently preferably hydrogen, a hydrocarbon group optionally having one or more substituents, or R ³ CO—, hydrogen, 1 an alkyl group optionally having one or more substituents, an aryl group optionally having one or more substituents, an aralkyl group optionally having one or more substituents, or R ³ It is more preferably CO—, more preferably hydrogen, an alkyl group optionally having one or more substituents, or R ³ CO—, and hydrogen, an alkyl group, or R ³ CO— is even more preferred, and hydrogen or R ³ CO— is particularly preferred.

In one embodiment, R ¹ and R ² are preferably the same group.

In one embodiment, R ³ is an alkyl group optionally having one or more substituents, an aryl group optionally having one or more substituents, or It is preferably an aralkyl group that may have one or more substituents, more preferably an alkyl group that may have one or more substituents, or an aryl group that may have one or more substituents. An alkyl group which may have one or more substituents is preferred, and more preferred. The substituent is preferably a hydroxyl group, a mercapto group, an alkoxy group, or an alkylthio group, more preferably an alkoxy group or an alkylthio group, and even more preferably an alkoxy group. When such substituents are present, the number of such substituents is selected from one or more and less than or equal to the maximum substitutable number, and is preferably one or two.

In one embodiment, X is hydrogen, halogen, nitro group, cyano group, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, aryl group, heteroaryl group, R ⁴ O—, R ⁵ S—, or R It is preferably ⁶ R ⁷ N—, more preferably halogen, a cyano group, or R ⁴ O—, still more preferably halogen, and even more preferably fluorine, chlorine, or bromine.

In one embodiment, R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently hydrogen, an alkyl group optionally having one or more substituents, a or an aralkyl group optionally having one or more substituents, hydrogen, an alkyl group optionally having one or more substituents, or 1 It is more preferably an aryl group optionally having one or more substituents, more preferably hydrogen or an alkyl group optionally having one or more substituents, hydrogen or alkyl is even more preferred.

In one embodiment, Z is preferably halogen, more preferably fluorine.

In one embodiment, R ⁸ is an alkyl group optionally having one or more substituents, an aryl group optionally having one or more substituents, or It is preferably an aralkyl group that may have one or more substituents, more preferably an alkyl group that may have one or more substituents, or an aryl group that may have one or more substituents. An alkyl group optionally having one or more substituents is preferred, and an alkyl group is even more preferred.

In one embodiment, R ¹ and R ² are each independently hydrogen or R ³ CO—, and R ³ may have one or more substituents (eg, alkoxy group) It is an alkyl group, and X and Z are each independently preferably halogen. In such embodiments, it is further preferred that X is fluorine.

In one embodiment, the compound represented by formula (1) or a salt thereof is preferably a compound or a salt thereof selected from the group consisting of the following formulas (1-1) to (1-12).

The salt of the compound represented by formula (1) may be an acid addition salt or a base addition salt.

The acid addition salt may be an inorganic acid salt or an organic acid salt. Examples of the inorganic acid salts include salts with hydrochloric acid, sulfuric acid, phosphoric acid, hydrobromic acid, hydroiodic acid, nitric acid, pyrosulfuric acid, and metaphosphoric acid. Examples of the organic acid salts include salts with citric acid, benzoic acid, acetic acid, propionic acid, fumaric acid, maleic acid, and sulfonic acid (eg, methanesulfonic acid, p-toluenesulfonic acid, and naphthalenesulfonic acid). contain.

Examples of the base addition salts include alkali metal salts such as sodium salts and potassium salts.

The method for producing the compound represented by formula (1) or a salt thereof is not particularly limited. For example, as shown in the reaction scheme below, the compound represented by formula (2) is converted to It is preferable to include a step A of reacting with a compound that

(Wherein, R ^1b and R ^2b are each independently a hydroxyl-protecting group, Halo is a halogen, and X and Z are the same as above.)

As the protecting group represented by R ^1b and R ^2b , all those generally used for protecting hydroxyl groups can be used. In one embodiment, R ^1b and R ^2b are each independently an ether-type protecting group (eg, t-butyl group, benzyl group, trityl group), an acetal-type protecting group (eg, tetrahydropyranyl group), acyl type protecting group (eg, acetyl group, benzoyl group), and silyl ether type protecting group (eg, t-butyldimethylsilyl group).

In one embodiment, Halo is preferably bromine or chlorine.

The amounts of the compound represented by formula (2) and the compound represented by formula (3) are not particularly limited as long as the reaction proceeds. The lower limit of the ratio (molar ratio) of the amount of the compound represented by formula (3) to the amount of the compound represented by formula (2) is, for example, 0.1, 0.5, or 1. can. The upper limit of the ratio can be 10, 9, 8, 7, 6, or 5, for example. The ratio can be, for example, 0.1-10, 0.5-8, or 1-5.

The reaction in step A is preferably carried out in the presence of a base. Suitable examples of such bases include non-nucleophilic bases, and specific examples thereof include metal hydrides (eg calcium hydride) and metal alkoxides (eg sodium t-butoxy, potassium t-butoxy). do. The said base can be used individually by 1 type or in combination of 2 or more types.

The reaction in step A is preferably carried out in a solvent. Suitable examples of the solvent include halogen solvents (eg, dichloromethane, chloroform, dichloroethane), alcohol solvents (eg, ethanol, propanol, butanol, t-amyl alcohol, pentanol), and nitrile solvents (eg, acetonitrile). ). The said solvent can be used individually by 1 type or in combination of 2 or more types.

The reaction temperature in step A is not particularly limited as long as the reaction proceeds. The lower limit of the reaction temperature can be, for example, 5°C, 10°C, or 15°C. The upper limit of the reaction temperature can be, for example, 100°C, 90°C, or 80°C. The reaction temperature can be, for example, 5-100°C, 10-90°C, or 15-80°C.

The method for producing the compound represented by formula (1) or a salt thereof may further include step B of deprotecting the hydroxyl-protecting group. Deprotection in step B can be carried out according to a conventional method.

In another embodiment, the compound represented by formula (1) or a method for producing the same comprises
Step D, carried out in the same manner as Step A, except that 2-amino-6-chloro-9H-proline is used in place of the compound represented by formula (3);
The product obtained from step D is reacted (Sandmeyer reaction ₎ with nitrite or nitrite ester and a bromine source ₍ e.g. CuBr, _CH2Br2 ) or an iodine source (e.g. CuI, _CH2I2 ). Step E, and step F of aminating the 6-position of the purine ring of the product obtained by step E, and deprotecting the protecting groups of the hydroxyl groups at the 3′ and 5′ positions of the furan ring skeleton.
It is preferred to include The method can be referred to, for example, WO2020/213501.

The compound represented by formula (1) or the method for producing the same may include step G of reacting the deprotected product obtained in step B or step F with R ³ COOH or its ester or halide. The reaction of step G (esterification reaction) can be carried out according to a conventional method.

In the compound represented by formula (1) or its manufacturing method, the product obtained in each step may be purified by means of filtration, column chromatography, concentration, extraction, etc., if desired.

The content of the compound represented by formula (1) or a salt thereof in the pest control composition is preferably an effective amount for controlling pests. The lower limit of the content is, for example, 0.01 parts by mass, 0.05 parts by mass, 0.1 parts by mass, 0.5 parts by mass, 1 part by mass, and 5 parts by mass with respect to 100 parts by mass of the pest control composition. parts, or 10 parts by weight. The upper limit of the content is, for example, 99 parts by mass, 90 parts by mass, 85 parts by mass, 80 parts by mass, 75 parts by mass, 70 parts by mass, 65 parts by mass, 60 parts by mass with respect to 100 parts by mass of the pest control composition. parts, 55 parts by weight, or 50 parts by weight. The content can be, for example, 0.01 to 99 parts by mass, 0.05 to 90 parts by mass, or 0.1 to 80 parts by mass with respect to 100 parts by mass of the pest control composition.

The pest control composition preferably contains the compound represented by formula (1) or a salt thereof, and a carrier. The carrier may be a solid carrier, a liquid carrier, or a gaseous carrier.

Examples of solid carriers include inorganic particles such as activated carbon, silica, talc, titanium dioxide, zeolite, calcium carbonate, and calcium phosphate; clay minerals such as kaolin, diatomaceous earth, bentonite, clay, and acid clay; polyethylene, polypropylene, polyvinylidene chloride, and the like. polymer particles; fertilizers; wood flour and the like.

Liquid carriers include, for example, water (e.g. tap water, ion-exchanged water, distilled water, sterilized water), alcohols (e.g. methanol, ethanol, isopropanol, butanol, ethylene glycol, propylene glycol), ethers (e.g. diethyl ether, methyl cellosolve, ethyl cellosolve, dimethyl cellosolve, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, tetrahydrofuran, dioxane), esters (e.g. ethyl acetate, diethyl phthalate), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl) ketone, cyclohexanone), aliphatic hydrocarbons (e.g. kerosene, mineral oil), aromatic hydrocarbons (e.g. xylene, toluene, alkylnaphthalene), halogenated hydrocarbons (e.g. dichloromethane, dichloroethane, chloroform, etc.), nitriles (eg, acetonitrile, isobutyronitrile), sulfoxides (eg, dimethylsulfoxide), amides (eg, N,N-dimethylformamide, N,N-dimethylacetamide), vegetable oils and the like.

Examples of gaseous carriers include butane gas; freon gas; alternative freon gases such as HFO and HFC; liquefied petroleum gas (LPG);

The carriers can be used singly or in combination of two or more. In one embodiment, the carrier is a solid carrier or a liquid carrier.

The lower limit of the ratio (mass ratio) of the content of the carrier to the content of the compound represented by formula (1) or a salt thereof can be 0.1, 0.5, or 1, for example. The upper limit of the ratio can be 1000, 900, 800, 700, 600, 500, 400, 300, 200, 100, 50, or 10, for example. The ratio can be, for example, 0.1-1000, 0.5-500, or 1-100.

The pest control composition can further contain optional additional ingredients (or adjuvants). An example of such additional ingredients is a surfactant. Surfactants may be any of nonionic surfactants, anionic surfactants, cationic surfactants, and amphoteric surfactants.

Examples of nonionic surfactants include fatty acid dialkanolamides (e.g. lauric acid diethanolamide), polyoxyalkylene fatty acid amides (e.g. polyoxyethylene stearamide), polyoxyalkylene aryl ethers (e.g. polyoxyethylene phenyl ether), polyoxyalkylene alkyl aryl ethers (e.g. polyoxyethylene octylphenyl ether), polyoxyalkylene alkyl or alkenyl ethers (e.g. polyoxyethylene lauryl ether, polyoxyethylene stearyl ether), fatty acid esters of polyhydric alcohols (Example: polyethylene glycol mono- or distearate, polyethylene glycol mono- or dilaurate, polyoxyethylene hydrogenated castor oil), glycerin fatty acid ester (eg: glyceryl monostearate, glyceryl monooleate), sorbitan fatty acid ester (eg: sorbitan monolaurate, sorbitan monostearate), polyoxyethylene-polyoxypropylene block polymers, and the like.

Examples of anionic surfactants include alkanesulfonic acid (e.g. dodecanesulfonic acid), arenesulfonic acid (e.g. dodecylbenzenesulfonic acid), polyalkylene glycol sulfonic acid (e.g. polyethylene glycol sulfonic acid), alkyl sulfate ( lauryl sulfate), polyoxyalkylene alkyl ether sulfate (eg, polyoxyethylene lauryl ether sulfate), polyoxyalkylene alkyl aryl ether sulfate (eg, polyoxyethylene alkylphenyl ether sulfate), alkyl phosphate (eg, lauryl phosphorus acid), polyoxyalkylene alkyl ether phosphate (e.g. polyoxyethylene lauryl ether phosphate), polyoxyalkylene aryl ether phosphate (e.g. polyoxyethylene phenyl ether phosphate), or salts thereof (such as sodium salts alkali metal salts), and long-chain fatty acid salts (eg, calcium stearate, magnesium stearate, aluminum monostearate, triethanolamine stearate, triethanolamine oleate), and the like.

Examples of cationic surfactants include tetraalkylammonium salts (eg, lauryltrimethylammonium chloride, dilauryldimethylammonium chloride), trialkylammonium salts (eg, lauryldimethylbenzylammonium chloride, benzalkonium chloride), tri( polyoxyalkylenealkyl)ammonium salts (eg, tri(polyoxyethylenestearyl)ammonium chloride) and the like.

Examples of amphoteric surfactants include betaines (eg, betaine; alkylbetaines such as dimethyldodecylcarboxybetaine), phosphatidic acid derivatives (eg, lecithin, lysolecithin, phosphatidylethanolamine), dimethylalkylamine oxides, and the like.

The surfactants can be used singly or in combination of two or more. The lower limit of the ratio (mass ratio) of the content of the surfactant to the content of the compound represented by formula (1) or a salt thereof can be 0.1, 0.5, or 1, for example. The upper limit of the ratio can be 1000, 900, 800, 700, 600, 500, 400, 300, 200, 100, 50, or 10, for example. The ratio can be, for example, 0.1-1000, 0.5-500, or 1-100.

Other examples of the additional ingredients include antifreeze agents, antifoaming agents, preservatives, antioxidants, thickeners, colorants, plasticizers, lubricants, dispersants, buffers, and trace elements.

The pest control composition is, for example,
powders [e.g., powders containing 0.1 to 10% by mass of the compound represented by formula (1) or a salt thereof and 90 to 99.9% by mass of a solid carrier],
granules [e.g. granules containing 0.1 to 30% by mass of the compound represented by formula (1) or a salt thereof and 70 to 99.5% by mass of solid carrier],
Wettable powder [e.g., a hydrating agent containing 0.5 to 90% by mass of a compound represented by formula (1) or a salt thereof, 5 to 95% by mass of a solid carrier, and 0.5 to 20% by mass of a surfactant agent],
Suspension concentrate [Example: Suspension concentrate containing 5 to 75% by mass of the compound represented by formula (1) or a salt thereof, 24 to 94% by mass of liquid carrier, and 1 to 40% by mass of surfactant product], or an emulsifiable concentrate [e.g., a suspension containing 1 to 95% by mass of a compound represented by formula (1) or a salt thereof, 1 to 80% by mass of a liquid carrier, and 1 to 30% by mass of a surfactant Turbidity Concentrate]
can be

The pests that can be controlled by the pest control composition can be, for example, pests or pathogens, and are preferably pests or pathogens for plants.

Examples of pests include, but are not limited to, insects, nematodes, mites, and ticks. The pests are preferably pests belonging to the systems or classifications shown in the table below.

The pest is more preferably a lepidopteran pest or a hemiptera pest, even more preferably a lepidopteran pest, and is at least one selected from the group consisting of diamondback moth pests and noctuid pests. Especially preferred.

Examples of the pathogens include rice blast pathogens, crest pathogens, anthrax pathogens, plague pathogens, powdery mildew pathogens, brown spot pathogens, mold pathogens (e.g. gray mold pathogens), rust pathogens, black star pathogens, brown streak pathogens, and banae. Pathogens, seedling wilt pathogens, rice rot pathogens, soft rot pathogens, canker pathogens, black rot pathogens, rot pathogens, flower thunder rot pathogens, root-knot pathogens, bacterial wilt pathogens, root rot pathogens, vine split pathogens, yellowing wilt pathogens , leaf blight pathogen, smut pathogen, and the like, but are not limited to these.

The pathogen is preferably at least one selected from the group consisting of rice blast pathogen, sheath blight pathogen, anthrax pathogen, and brown spot pathogen.

When the pest controllable by the pest control composition is a plant pest or pathogen, the plant may be a whole plant or a part of the plant. Examples of plant parts include stems, leaves, flowers, ears, fruits, stems, branches, seeds, roots, shoots, and seedlings.

Examples of the plants include gramineous plants (e.g., rice, barley, wheat, corn, oats), cruciferous plants (e.g., Japanese radish, turnip, Chinese cabbage, cabbage, white mustard, mizuna, mibuna, Japanese mustard spinach, broccoli, cauliflower), Cucurbitaceous plants (e.g. pumpkin, cucumber, white mustard, watermelon, castor bean, melon), solanaceous plants (e.g. peppers, eggplants, tomatoes, peppers, potatoes, green peppers), umbelliferous plants (e.g. carrots, parsley, mitsuba, celery), Liliaceae plants (e.g. green onions, onions, chives, spring onions, shallots), Asteraceae plants (e.g. chrysanthemums, chrysanthemums, burdocks, sunflowers, lettuce, butterbur, baby leaves), Chenopodiaceae plants (e.g. spinach, Swiss chard), bindweed (e.g. sweet potato), legumes (e.g. peas, soybeans, fava beans, edamame, kidney beans, peanuts), roses (e.g. strawberries, peaches, plums, apples, pears), and grapes Includes family plants (eg grapes).

The plant is preferably at least one selected from the group consisting of gramineous plants, cruciferous plants, cucurbitaceous plants, leguminous plants, rosaceous plants, and vine plants. , cucurbitaceous plants, and legumes.

In one embodiment, the pest control composition may be applied directly to the pest, or applied to a place where the pest lives or can live (or generate). Examples of places where harmful organisms live or can live include places where agricultural products and foliage plants are grown (e.g. vinyl greenhouses, orchards, fields, gardens, planters), places where agricultural products and foliage plants are stored ( Examples: kitchens, warehouses), etc.

In one embodiment, the pest control composition may be applied directly to the plant (in whole or in part) or to the soil in which the plant is grown.

As for the application method, all the methods generally employed for application of pest control compositions can be employed, for example, application or spraying. The lower limit of the application amount of the pest control composition is, for example, 1 g, 5 g, 10 g, 15 g, 20 g, 25 g, 30 g, 35 g, 40 g, 45 g, 50 g, 100 g, 200 g, 300 g, 400 g, or 500 g per hectare of application area. can be The upper limit of the application amount can be, for example, 10,000 g, 9,000 g, 8,000 g, 7,000 g, 6,000 g, 5,000 g, 4,000 g, 3,000 g, and 2,000 g per ha. The application rate can be, for example, 1-10000 g, 5-9000 g, or 10-8000 g per ha.

3. The compound represented by formula (1a) or a salt thereof in the present disclosure is represented by the following formula (1a):

(In the formula,
R ^1a and R ^2a are each independently a hydrocarbon group optionally having one or more substituents, R ^3a CO—, or a sulfamoyl group,
R ^3a is a hydrocarbon group optionally having one or more substituents,
X ^a is a halogen, a nitro group, a cyano group, a hydrocarbon group optionally having one or more substituents, a heteroaryl group, R ^4a O—, or R ^5a S—;
R ^4a and R ^5a are each hydrogen or a hydrocarbon group optionally having one or more substituents,
Z ^a is a halogen, an azide group, a cyano group, or R ^8a O—;
R ^8a is a hydrocarbon group optionally having one or more substituents. )
The compound represented by or its salt is included.

In one embodiment, R ^1a and R ^2a are each independently a hydrocarbon group optionally having one or more substituents, or R ^3a CO—, preferably one or more substituted an alkyl group optionally having a group, an aryl group optionally having one or more substituents, an aralkyl group optionally having one or more substituents, or R ^3a CO— more preferably an alkyl group optionally having one or more substituents, or R ^3a CO—, even more preferably an alkyl group or R ^3a CO—, and R ^3a CO— is particularly preferred.

In one embodiment, R ^1a and R ^2a are preferably the same group.

In one embodiment, R ^3a is an alkyl group optionally having one or more substituents, an aryl group optionally having one or more substituents, or It is preferably an aralkyl group that may have one or more substituents, more preferably an alkyl group that may have one or more substituents, or an aryl group that may have one or more substituents. An alkyl group which may have one or more substituents is preferred, and more preferred. The substituent is preferably a hydroxyl group, a mercapto group, an alkoxy group, or an alkylthio group, more preferably an alkoxy group or an alkylthio group, and even more preferably an alkoxy group. The number of the substituents may be one or more and not more than the maximum substitutable number, preferably one or two.

In one embodiment, X ^a is a halogen, nitro group, cyano group, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, aryl group, heteroaryl group, R ^4a O—, or R ^5a S— is preferred, halogen, a cyano group, or R ^4a O— is more preferred, halogen is even more preferred, and fluorine, chlorine, or bromine is even more preferred.

In one embodiment, R ^4a and R ^5a are each hydrogen, an alkyl group optionally having one or more substituents, an aryl group optionally having one or more substituents, or 1 It is preferably an aralkyl group optionally having one or more substituents, such as hydrogen, an alkyl group optionally having one or more substituents, or having one or more substituents It is more preferably an aryl group that may be substituted, more preferably hydrogen or an alkyl group optionally having one or more substituents, and even more preferably hydrogen or an alkyl group.

In one embodiment, Z ^a is preferably halogen, more preferably fluorine.

In one embodiment, R ^8a is an alkyl group optionally having one or more substituents, an aryl group optionally having one or more substituents, or It is preferably an aralkyl group that may have one or more substituents, more preferably an alkyl group that may have one or more substituents, or an aryl group that may have one or more substituents. An alkyl group optionally having one or more substituents is preferred, and an alkyl group is even more preferred.

In one embodiment, R ^1a and R ^2a are each independently R ^3a CO—, and R ^3a is an alkyl group optionally having one or more substituents (eg, an alkoxy group). and X ^a and Z ^a are each independently preferably halogen, R ^1a and R ^2a are each independently R ^3a CO—, and R ^3a is one or more substituents It is an alkyl group optionally having (eg, an alkoxy group), X ^a is fluorine, and Z ^a is more preferably halogen.

In one embodiment, the compound represented by formula (1a) or a salt thereof is preferably a compound or a salt thereof selected from the group consisting of the following formulas (1a-1) to (1a-9).

The salt of the compound represented by formula (1a) can be, for example, a salt with an acid or base exemplified for the salt of the compound represented by formula (1).

The compound represented by formula (1a) or a salt thereof can be produced, for example, in the same manner as the compound represented by formula (1) or a salt thereof.

An embodiment of the present disclosure will be described in more detail below by way of examples, but the present disclosure is not limited thereto. In addition, the abbreviation "Bz" means a benzoyl group in the present Examples.

(Example 1)
After dissolving 5 g (10.8 mmol) of 2-deoxy-2-fluoro-1,3,5-tri-O-benzoyl-α-D-arabinofuranose in 20 mL of dehydrated dichloromethane, hydrogen bromide-acetic acid solution (5.1 mol /L) 4.8 mL (24.5 mmol) was added dropwise and stirred for 16 hours. After adding chloroform to the reaction solution, the reaction solution was washed with water, a saturated aqueous solution of sodium hydrogencarbonate and saturated brine in that order, and dried by adding sodium sulfate. After filtering this solution, 4.56g of compounds 1 were obtained by concentration-drying.

¹ H NMR (CDCl ₃ , 400 MHz) δ: 4.70-4.83 (m, 3 H), 5.50-5.65 (m, 2 H), 6.61 and 6.65 (d×2, 1 H), 7.42-7.62 (m, 6 H), 8.04-8.11 (m, 4 H). ¹⁹ F NMR (CDCl ₃ , 400 MHz) δ: -165.73-165.95.

After dissolving 0.477 g (4.25 mmol) of t-butoxypotassium and 0.179 g (4.25 mmol) of calcium hydride in 20 mL of t-amyl alcohol and 4 mL of dehydrated acetonitrile, 0.721 g (4.25 mmol) of 2-chloroadenine was added. Subsequently, a solution of 1.2 g (2.84 mmol) of compound 1 dissolved in 6 mL of dehydrated acetonitrile was added dropwise. After dropping, the mixture was stirred at 50°C for 16 hours. 0.327g of compound 2 was obtained by performing column refinement|purification after adding ethyl acetate to the reaction solution and filtering.

¹ H NMR (CDCl ₃ , 400 MHz) δ: 4.55-4.57 (m, 1 H), 4.79-4.80 (m, 2 H), 5.28 and 5.40 (d×2, 1 H), 5.72 and 5.76 (d× 2, 1 H), 5.80 (br s, 2 H), 6.53 and 6.59 (d×2, 1 H), 7.44-7.58 (m, 6 H), 8.05-8.10 (m ^, 5 H). ( _CDCl3 , 400 MHz) δ: -198.35-198.59.

After dissolving 0.327 g (0.64 mmol) of compound 2 in 3.0 mL of tetrahydrofuran and 1 mL of methanol, 0.069 g (1.28 mmol) of sodium methoxide was added and stirred for 1 hour. After the reaction solution was concentrated to dryness, 0.139 g of compound 3 was obtained by performing column purification.

¹ H NMR (CD ₃ CN, 400 MHz) δ: 3.82-3.83 (m, 2 H), 3.99-4.00 (m, 1 H), 4.20-4.22 (m, 1 H), 4.62-4.68 (m, 1 H), 5.09 (d, 1H), 5.17 and 5.30 (t×2, 1H), 6.37 and 6.41 (d×2, 1H), 6.99 (br s, 2H), 8.16 (s, 1H) ). ¹⁹ F NMR (CD ₃ CN, 400 MHz) δ: -198.12-198.88.

(Example 2)
After 0.122 g (0.4 mmol) of compound 3 was dissolved in 3.0 mL of dehydrated pyridine, 0.127 mL (0.922 mmol) of 4-methylpentanoyl chloride was added and stirred for 16 hours. Chloroform and 3N HCl were added to the reaction solution for liquid separation, and the mixture was washed with water. After concentrating and drying this chloroform layer, 0.145g of compound 4 was obtained by performing column refinement|purification.

¹ H NMR (CDCl ₃ , 400 MHz) δ: 0.88 and 0.94 (d, 12 H), 1.53-1.57 (m, 6 H), 2.34-2.43 (m, 4 H), 4.23-4.25 (m, 1 H ), 4.41-4.46 (m, 2H), 5.04 and 5.17 (d×2, 1H), 5.31 and 5.35 (d×2, 1H), 6.00 (br s, 2H), 6.40 and 6.45 (d ×2, 1H), 8.03(s, 1H)
¹⁹ F NMR (CDCl ₃ , 400 MHz) δ: -198.35-198.59

(Example 3)
After 0.122 g (0.4 mmol) of compound 3 was dissolved in 3.0 mL of dehydrated pyridine, 0.084 mL (0.92 mmol) of methoxyacetyl chloride was added and stirred for 16 hours. Chloroform and 3N HCl were added to the reaction solution for liquid separation, and the mixture was washed with water. After concentrating and drying this chloroform layer, 0.123g of compound 5 was obtained by performing column refinement|purification.

¹ H NMR (CDCl ₃ , 400 MHz) δ: 3.46 and 3.49 (s×2, 6 H), 4.11 and 4.12 (s×2, 4 H), 4.29-4.31 (m, 1 H), 4.54-4.59 ( m, 2H), 5.10 and 5.22 (d×2, 1H), 5.42 and 5.43 (d×2, 1H), 5.74 (br s, 2H), 6.41 and 6.47 (d×2, 1H) , 8.05 (s, 1 H). ¹⁹ F NMR (CDCl ₃ , 400 MHz) δ: -198.70-198.93.

(Example 4)
After 0.139 g (0.46 mmol) of compound 3 was dissolved in 5.0 mL of dehydrated pyridine, 0.146 mL (1.05 mmol) of hexanoyl chloride was added and stirred for 16 hours. Chloroform and 3N HCl were added to the reaction solution for liquid separation, and the mixture was washed with water. After concentrating and drying this chloroform layer, 0.12g of compound 6 was obtained by performing column refinement|purification.

¹ H NMR (CDCl ₃ , 400 MHz) δ: 0.88-0.94 (m, 6 H), 1.20-1.35 (m, 8 H), 1.50-1.70 (m, 4 H), 2.34-2.45(m, 4 H ), 4.20-4.25 (m, 1H), 4.30-4.50 (m, 2H), 5.04 and 5.17 (d×2, 1H), 5.32 and 5.37 (d×2, 1H), 5.71 (br s , 2 H), 6.40 and 6.45 (d×2, 1 H), 8.03 (s, 1 H).
¹⁹ F NMR (CDCl ₃ , 400 MHz) δ: -198.35-198.60.

(Example 5)
2-bromo-6-chloropurine 9-β-D-(2'-deoxy-3',5'-di-O-benzoyl-2'-fluoro)arabinoriboside 1.05 g (1.82 mmol) was added to tetrahydrofuran 1.0. mL, dissolved in 6 mL of ammonium/methanol (2 M) and stirred overnight at 100°C. After the reaction solution was concentrated to dryness, 0.38 g of compound 7 was obtained by performing column purification.

¹ H NMR (DMSO-d6, 400 MHz) δ: 3.59-3.64 (m, 2 H), 3.80-3.83 (m, 1 H), 4.35-4.41 (m, 1 H), 5.03 (t, 1 H) , 5.12 and 5.26 (t×2, 1 H), 5.91 (d, 1 H), 6.26 and 6.29 (d×2, 1 H), 7.85 (br s, 2 H), 8.21 (s, 1 H). ¹⁹ F NMR (DMSO-d6, 400 MHz) δ: -197.87-198.10.

(Example 6)
After 0.121 g (0.348 mmol) of compound 7 was dissolved in 5.0 mL of dehydrated pyridine, 0.105 mL (0.767 mmol) of 4-methylpentanoyl chloride was added and stirred for 16 hours. Ethyl acetate and 3N HCl were added to the reaction solution for liquid separation, and then washed with water. After concentrating and drying this ethyl acetate layer, 0.195g of compound 8 was obtained by performing column refinement|purification.

¹ H NMR (CDCl ₃ , 400 MHz) δ: 0.88 and 0.94 (d, 12 H), 1.55-1.59 (m, 6 H), 2.37-2.45 (m, 4 H), 4.23-4.25 (m, 1 H ), 4.39-4.46 (m, 2H), 5.05 and 5.17 (d×2, 1H), 5.31 and 5.36 (d×2, 1H), 5.89 (br s, 2H), 6.40 and 6.46 (d ×2, 1H), 8.01 (s, 1H).
¹⁹ F NMR (CDCl ₃ , 400 MHz) δ: -198.27-198.51.

(Example 7)
After 0.08 g (0.23 mmol) of compound 7 was dissolved in 8.0 mL of dehydrated pyridine, 0.0694 mL (0.506 mmol) of hexanoyl chloride was added and stirred for 16 hours. After the reaction solution was concentrated to dryness, 0.061 g of compound 9 was obtained by performing column purification.

¹ H NMR (CDCl ₃ , 400 MHz) δ: 0.85-0.94 (m, 6 H), 1.25-1.34 (m, 8 H), 1.55-1.67 (m, 4 H), 2.34-2.41 (m, 4 H ), 4.20-4.25 (m, 1H), 4.40-4.48 (m, 2H), 5.04 and 5.17 (d×2, 1H), 5.32 and 5.36 (d×2, 1H), 5.73 (br s , 2 H), 6.40 and 6.45 (d×2, 1 H), 8.01 (s, 1 H).
¹⁹ F NMR (CDCl ₃ , 400 MHz) δ: -198.26-198.50.

(Example 8)
After 0.16 g (0.46 mmol) of compound 7 was dissolved in 4.0 mL of dehydrated pyridine, 0.092 mL (1.01 mmol) of methoxyacetyl chloride was added and stirred for 16 hours. Chloroform and 3N HCl were added to the reaction solution, and the mixture was separated and then washed with water. After concentrating and drying this chloroform layer, 0.11g of compound 10 was obtained by performing column refinement|purification.

¹ H NMR (CDCl ₃ , 400 MHz) δ: 3.44 and 3.49 (s×2, 6 H), 4.10 and 4.15 (s×2, 4 H), 4.29-4.31 (m, 1 H), 4.54-4.60 ( m, 2H), 5.10 and 5.23 (d×2, 1H), 5.43 and 5.47 (d×2, 1H), 5.76 (br s, 2H), 6.41 and 6.47 (d×2, 1H) , 8.02 (s, 1 H). ¹⁹ F NMR (CDCl ₃ , 400 MHz) δ: -198.60-198.85.

(Example 9)
After dissolving 1.26 g (2.98 mmol) of compound 1 and 1.10 g (7.18 mmol) of 2-fluoroadenine in 10 mL of dehydrated acetonitrile, 2.76 mL (8.96 mmol) of BSA was added and the mixture was stirred at 80°C for 1 hour. After cooling to 0°C, 1.3 mL (7.18 mmol) of trimethylsilyl trifluoromethanesulfonate was added, and the mixture was stirred for 15 minutes, then heated to 80°C again and stirred overnight. A saturated aqueous sodium hydrogencarbonate solution and chloroform were added to the reaction solution, and the mixture was filtered through celite and separated. This chloroform layer was washed with water, concentrated to dryness, and subjected to column purification to obtain 0.254 g of compound 11.

¹ H NMR (CDCl ₃ , 400 MHz) δ: 4.55-4.57 (m, 1 H), 4.79-4.80 (m, 2 H), 5.26 and 5.39 (d×2, 1 H), 5.72 and 5.76 (d× 2, 2 H), 6.47 and 6.53 (d×2, 1 H), 7.45-7.55 (m, 6 H), 8.03-8.11 (m, 5 H).
¹⁹ F NMR (CDCl ₃ , 400 MHz) δ: -50.46, -197.87-198.13.

After dissolving 0.25 g (0.51 mmol) of compound 11 in 6.0 mL of tetrahydrofuran and 3 mL of methanol, 0.049 g (0.91 mmol) of sodium methoxide was added and stirred for 30 minutes. After the reaction solution was concentrated to dryness, 0.138 g of compound 12 was obtained by performing column purification.

¹ H NMR (DMSO-d6, 400 MHz) δ: 3.60-3.70 (m, 2 H), 3.78-3.81 (m, 1 H), 4.05-4.08 (m, 1 H), 4.36-4.42 (m, 1 H), 5.04 (t, 1H), 5.11 and 5.24 (t×2, 1H), 5.91 (d, 1H), 6.22 and 6.26 (d×2, 1H), 7.90 (br s, 2H ), 8.19 (s, 1 H). ¹⁹ F NMR (DMSO-d6, 400 MHz) δ: -50.40, -199.05-199.22.

(Example 10)
After 0.137 g (0.477 mmol) of compound 12 was dissolved in 4.0 mL of dehydrated pyridine, 0.096 mL (1.05 mmol) of methoxyacetyl chloride was added and stirred for 16 hours. Ethyl acetate and 3N HCl were added to the reaction solution for liquid separation, and then washed with water. After concentrating and drying this ethyl acetate layer, 0.093g of compounds 13 were obtained by performing column refinement|purification.

¹ H NMR (CDCl ₃ , 400 MHz) δ: 3.43 and 3.48 (s×2, 6 H), 4.11 and 4.14 (s×2, 4 H), 4.31-4.32 (m, 1 H), 4.54-4.58 ( m, 2H), 5.09 and 5.21 (d×2, 1H), 5.43 and 5.46 (d×2, 1H), 5.74 (br s, 2H), 6.35 and 6.41 (d×2, 1H) , 8.02 (s, 1 H). ¹⁹ F NMR (CDCl ₃ , 400 MHz) δ: -50.40, -199.05-199.22.

(Example 11)
After 0.102 g (0.355 mmol) of compound 12 was dissolved in 3.0 mL of dehydrated pyridine, 0.112 mL (0.817 mmol) of 4-methylpentanoyl chloride was added and stirred for 16 hours. Chloroform and 3N HCl were added to the reaction solution for liquid separation, and the mixture was washed with water. After concentrating and drying this chloroform layer, 0.129g of compound 14 was obtained by performing column refinement|purification.

¹ H NMR (CDCl ₃ , 400 MHz) δ: 0.88 and 0.94 (d, 12 H), 1.55-1.59 (m, 6 H), 2.37-2.40 (m, 4 H), 4.20-4.25 (m, 1 H ), 4.39-4.49 (m, 2H), 5.03 and 5.16 (d×2, 1H), 5.32 and 5.36 (d×2, 1H), 5.81 (br s, 2H), 6.34 and 6.40 (d ×2, 1H), 8.03 (s, 1H).
¹⁹ F NMR (CDCl ₃ , 400 MHz) δ: -50.40, -198.64-198.90.

(Test example 1)
Compound 3 of Example 1 (1 part by mass) was mixed with supplementary materials (xylene:DMF:Solpol 3005X (Toho Chemical Industry Co., Ltd.) = 4:4:1) (9 parts by mass) to give a concentration of 10%. An emulsion was prepared. A diluted solution of a predetermined concentration was prepared with water containing 10,000 times the spreading agent Grameen S (Toyo Green Co., Ltd.). A sufficient amount of the diluted drug solution was sprayed on each sample with a spray gun.

(Test example 2)
Compound 13 (1 part by mass) of Example 10 was mixed with auxiliary agents (xylene:DMF:Solpol 3005X (Toho Chemical Industry Co., Ltd.) = 4:4:1) (9 parts by mass) to give a concentration of 10%. An emulsion was prepared. A diluted solution of a predetermined concentration was prepared with water containing 10,000 times the spreading agent Grameen S (Toyo Green Co., Ltd.). A sufficient amount of the diluted drug solution was sprayed on the sample with a spray gun.

Test method for diseases and pests After spraying the chemicals on the test specimen, it was air-dried, and 10 test insects were released. Plants were covered with cups and nylon gauze to prevent test insect escape. The mortality rate was calculated from the number of surviving insects after 6 days, and the corrected mortality rate was calculated using the following formula:
It was calculated based on the corrected mortality rate (%)=[(survival rate in untreated area−survival rate in treated area)/survival rate in untreated area]×100.

Test method for rice blast fungi 2. Spray the drug on seedlings at the 5-leaf stage, place it in a wet room for 8 days with the rice blast-affected strain, measure the area of lesion formation, and control from the ratio to the untreated section. The value is given by the following formula (N):
Control value = 100 - (damage in treated area/damage in untreated area) x 100 (N)

Test method for sheath blight fungi Spray the chemical on rice at the 5-leaf stage, sprinkle the sheath blight fungus (winter) on the ground, leave it in a wet room for 6 days, measure the increase in lesions, and control. The value was calculated based on the above formula (N).

Test method for anthracnose fungus Primary leaves of soybean at the stage of full development of the first true leaf were sprayed with a chemical agent, inoculated with a spore suspension of anthracnose fungus by spraying, and left in a moist room for 7 days. The lesion area on the leaves was measured, and the control value was calculated based on the above formula (N).

Test method for Pseudomonas aeruginosa Two-leaf stage cucumbers were sprayed with the drug, spray-inoculated with a spore suspension of Pseudomonas aeruginosa, and left in a wet room for 8 days. The lesion area on the leaves was measured, and the control value was calculated based on the above formula (N).

The test results are shown in Tables 2 and 3. In addition, phytotoxicity was also confirmed in the test method for each pathogen, but no phytotoxicity was observed.

Claims

Formula (1) below:

(In the formula,
R 1 and R 2 are each independently hydrogen, a hydrocarbon group optionally having one or more substituents, R 3 CO—, or a sulfamoyl group;
R 3 is a hydrocarbon group optionally having one or more substituents,
X is hydrogen, halogen, nitro group, cyano group, hydrocarbon group optionally having one or more substituents, heteroaryl group, R 4 O—, R 5 S—, or R 6 R 7 N - and
R 4 , R 5 , R 6 and R 7 are each independently hydrogen or a hydrocarbon group optionally having one or more substituents,
Z is hydrogen, halogen, an azide group, a cyano group, or R 8 O—;
R 8 is a hydrocarbon group optionally having one or more substituents. )
A pest control composition containing a compound represented by or a salt thereof.
2. The pest control composition of claim 1, wherein R 1 and R 2 are each independently hydrogen or R 3 CO-.
3. The pest control composition according to claim 1 or 2, wherein R3 is an alkyl group optionally having one or more substituents.
X is hydrogen, halogen, nitro group, cyano group, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, aryl group, heteroaryl group, R 4 O—, R 5 S—, or R 6 R 7 N— and
R 4 , R 5 , R 6 and R 7 are each independently hydrogen or an alkyl group optionally having one or more substituents;
The pest control composition according to any one of claims 1-3.
The pest control composition according to any one of claims 1 to 4, wherein X is a halogen, a cyano group, or R 4 O-.
The pest control composition according to any one of claims 1 to 5, wherein X is fluorine, chlorine, or bromine.
The pest control composition according to any one of claims 1 to 6, wherein Z is halogen.
The pest control composition according to any one of claims 1 to 7, wherein Z is fluorine.
The pest control composition according to any one of claims 1 to 8, wherein the pest is a plant pest or pathogen.
The pest control composition according to claim 9, wherein the plant is at least one selected from the group consisting of gramineous plants, cruciferous plants, cucurbitaceous plants, and leguminous plants.
Any one of claims 1 to 10, wherein the pest is at least one selected from the group consisting of lepidopteran pests, hemiptera pests, rice blast pathogens, sheath blight pathogens, anthrax pathogens, and brown spot pathogens. The pest control composition according to 1.
The pest control composition according to any one of claims 1 to 11, for direct application to plants or application to the soil in which plants are grown.
Formula (1a) below:

(In the formula,
R 1a and R 2a are each independently a hydrocarbon group optionally having one or more substituents, R 3a CO—, or a sulfamoyl group,
R 3a is a hydrocarbon group optionally having one or more substituents,
X a is a halogen, a nitro group, a cyano group, a hydrocarbon group optionally having one or more substituents, a heteroaryl group, R 4a O—, or R 5a S—;
R 4a and R 5a are each hydrogen or a hydrocarbon group optionally having one or more substituents,
Z a is a halogen, an azide group, a cyano group, or R 8a O—;
R 8a is a hydrocarbon group optionally having one or more substituents. )
A compound represented by or a salt thereof.