Fluorine-containing pyridine compounds and methods for their manufacture

Abstract

A novel fluorine-containing pyridine compound and a method for producing the same are provided. A fluorine-containing pyridine compound represented by the following general formula (a). A 1 and A 2 is a fluorine atom or OR 1 , but when A 1 is a fluorine atom, A 2 is OR 1 , and when A 1 is OR 1 , A 2 is a fluorine atom; R 1 represents a hydrocarbon group having 1 to 12 carbon atoms; R 2 represents an aryl group, a heteroaryl group, a cyano group, -X- (Y 1 n -R 4 ) m , or -(C=NR 5 ) -Y 2 -R 6 ; and R 3 represents a hydrogen atom, or represents an alkyl group having 1 to 12 carbon atoms, an aryl group, or a heteroaryl group. A novel fluorine-containing pyridine compound and a method for producing the same are provided.

Description

Technical Field

[0001] This invention relates to a fluorinated pyridine compound and a method for manufacturing the same. Background Technology

[0002] Compounds with pyridine ring structures play important roles in the life activities of a wide range of organisms, from eukaryotes to prokaryotes. Specifically, nicotinamide adenine dinucleotide and pyridoxal phosphate, both with pyridine ring structures, are known to be indispensable cofactors in the activity of various enzymes. Against this backdrop, a large number of pharmaceutical products with pyridine ring structures have been developed to date. Specific examples of such pharmaceutical products include isoniazid as an anti-tuberculosis drug and ceftazidime as an antibacterial drug. Furthermore, in the agricultural field, compounds with pyridine ring structures are widely used, for example, as pesticides for controlling harmful fungi (fungicides, etc.), arthropods (insecticides, etc.), and herbicides. Specific examples of pesticides with pyridine ring structures include chlorpyrifos as an insecticide and boscalid as a fungicide.

[0003] Furthermore, in recent years, there has been interest in enhancing activity by introducing fluorine atoms and / or fluorine-containing substituents into the pyridine ring. Specifically, as pharmaceuticals, mefloquine, an antimalarial drug with a partial structure of 2-trifluoromethylpyridine, and enoxacin, an antibacterial drug with a partial structure of 3-fluoropyridine, are known. As pesticides, fluazinam, a fungicide with a partial structure of 3-trifluoromethylpyridine, and fluazinam, a herbicide with a partial structure of 2-fluoropyridine, are known.

[0004] Patent document 1 discloses a useful method for manufacturing a fluorinated pyrimidine compound having a structure related to fluorinated pyridine compounds.

[0005] Existing technical documents Invention Patent Documents Invention Patent Document 1: International Publication No. 2020 / 116296 Summary of the Invention

[0006] The problem that the invention aims to solve Compounds with a trifluoromethyl group at the 3-position of the pyridine ring are useful not only in the pharmaceutical and pesticide fields but also in the field of organic electronic materials. However, reported examples of such compounds and their manufacturing methods are extremely limited. Therefore, providing a novel and manufacturable compound with a trifluoromethyl group at the 3-position of the pyridine ring is of great value in itself. Furthermore, such compounds are not only useful in themselves, but also offer greater structural scalability when multiple substituents are present besides the trifluoromethyl group, making them promising as useful intermediates for obtaining further compounds.

[0007] This invention provides a novel fluorinated pyridine compound and its manufacturing method.

[0008] Methods for solving problems The main structure of this invention is as follows.

[0009] [1] A fluorinated pyridine compound represented by the following general formula (a).

[0010] [Chemical Formula 1] (In general formula (a), A 1 And A 2 They are fluorine atoms or OR 1 However, when A 1 When A is a fluorine atom, 2 OR 1 , when A 1 OR 1 At that time, A 2 It is a fluorine atom; R 1 Hydrocarbon groups representing 1 to 12 carbon atoms; R 2 Indicates aryl, heteroaryl, cyano, -X-(Y) 1 n -R 4 ) m , or - (C=NR) 5 )-Y 2 -R 6 ,in, X represents CO, SO, SO2, or PO. Y 1 and Y 2 Each can be represented independently as O, S, or NR. 7 , n represents an integer that is either 0 or 1. m represents an integer of 1 or 2. R 4 R 5 R 6 R 7 Each of the 1 to 12 carbon atoms is represented independently by a hydrocarbon group. However, R 4 With R 7 R 5 With R 6 Or R 6 With R 7 They can also combine to form a ring; R 3(This represents a hydrogen atom, or an alkyl, aryl, or heteroaryl group with 1 to 12 carbon atoms.) [2] Fluorinated pyridine compounds of [1] represented by the following general formula (1).

[0011] [Chemical Formula 2] (In general formula (1), R) 1 R 2 and R 3 As defined above. [3] Fluorinated pyridine compounds of [1] represented by the following general formula (2).

[0012] [Chemical Formula 3] (In general formula (2), R) 1 R 2 and R 3 As defined above. [4] A method for manufacturing a fluorinated pyridine compound, comprising the following steps: obtaining a fluorinated pyridine compound represented by the following general formula (1) by reacting a fluorinated isobutylene derivative represented by the following general formula (3) with a compound represented by the following general formula (4) or a salt thereof.

[0013] [Chemical Formula 4] (In general formulas (1), (3) and (4), R 1 Hydrocarbon groups representing 1 to 12 carbon atoms; R 2 Indicates aryl, heteroaryl, cyano, -X-(Y) 1 n -R 4 ) m , or - (C=NR) 5 )-Y 2 -R 6 ,in, X represents CO, SO, SO2, or PO. Y 1 and Y 2 Each can be represented independently as O, S, or NR. 7 , n represents an integer that is either 0 or 1. m represents an integer of 1 or 2. R 4 R 5 R 6 R 7Each of the 1 to 12 carbon atoms is represented independently by a hydrocarbon group. However, R 4 With R 7 R 5 With R 6 Or R 6 With R 7 They can also combine to form a ring; R 3 (This represents a hydrogen atom, or an alkyl, aryl, or heteroaryl group with 1 to 12 carbon atoms.) [5] A method for manufacturing a fluorinated pyridine compound, comprising the following steps: obtaining a fluorinated pyridine compound represented by the following general formula (1) by reacting a fluorinated isobutane derivative represented by the following general formula (5) with a compound represented by the following general formula (4) or a salt thereof.

[0014] [Chemical Formula 5] (In general formulas (1), (4) and (5), R 1 Hydrocarbon groups representing 1 to 12 carbon atoms; R 2 Indicates aryl, heteroaryl, cyano, -X-(Y) 1 n -R 4 ) m , or - (C=NR) 5 )-Y 2 -R 6 ,in, X represents CO, SO, SO2, or PO. Y 1 and Y 2 Each can be represented independently as O, S, or NR. 7 , n represents an integer that is either 0 or 1. m represents an integer of 1 or 2. R 4 R 5 R 6 R 7 Each of the 1 to 12 carbon atoms is represented independently by a hydrocarbon group. However, R 4 With R 7 R 5 With R 6 Or R 6 With R 7 They can also combine to form a ring; R 3(This represents a hydrogen atom, or an alkyl, aryl, or heteroaryl group with 1 to 12 carbon atoms.) [6] A method for manufacturing a fluorinated pyridine compound, comprising the following steps: obtaining a fluorinated pyridine compound represented by general formula (2) by reacting a fluorinated isobutylene derivative represented by general formula (3) with a compound or a salt thereof represented by general formula (6).

[0015] [Chemical Formula 6] (In general formulas (2), (3) and (6), R 1 Hydrocarbon groups representing 1 to 12 carbon atoms; R 2 Indicates aryl, heteroaryl, cyano, -X-(Y) 1 n -R 4 ) m , or - (C=NR) 5 )-Y 2 -R 6 ,in, X represents CO, SO, SO2, or PO. Y 1 and Y 2 Each can be represented independently as O, S, or NR. 7 , n represents an integer that is either 0 or 1. m represents an integer of 1 or 2. R 4 R 5 R 6 R 7 Each of the 1 to 12 carbon atoms is represented independently by a hydrocarbon group. However, R 4 With R 7 R 5 With R 6 Or R 6 With R 7 They can also combine to form a ring; R 3 It represents a hydrogen atom, or an alkyl, aryl, or heteroaryl group having 1 to 12 carbon atoms; Z represents cyano or -V-(O) l -R 8 ) k ,in, V represents SO, SO2, or PO. l represents an integer that is either 0 or 1. k represents an integer of 1 or 2. R8 (This refers to hydrocarbon, aryl, or heteroaryl groups with 1 to 12 carbon atoms.) [7] A method for manufacturing a fluorinated pyridine compound, comprising the following steps: obtaining a fluorinated pyridine compound represented by general formula (2) by reacting a fluorinated isobutane derivative represented by general formula (5) with a compound or a salt thereof represented by general formula (6).

[0016] [Chemical Formula 7] (In general formulas (2), (5) and (6), R 1 Hydrocarbon groups representing 1 to 12 carbon atoms; R 2 Indicates aryl, heteroaryl, cyano, -X-(Y) 1 n -R 4 ) m , or - (C=NR) 5 )-Y 2 -R 6 ,in, X represents CO, SO, SO2, or PO. Y 1 and Y 2 Each can be represented independently as O, S, or NR. 7 , n represents an integer that is either 0 or 1. m represents an integer of 1 or 2. R 4 R 5 R 6 R 7 Each of the 1 to 12 carbon atoms is represented independently by a hydrocarbon group. However, R 4 With R 7 R 5 With R 6 Or R 6 With R 7 They can also combine to form a ring; R 3 It represents a hydrogen atom, or an alkyl, aryl, or heteroaryl group having 1 to 12 carbon atoms; Z represents cyano or -V-(O) l -R 8 ) k ,in, V represents SO, SO2, or PO. l represents an integer that is either 0 or 1. k represents an integer of 1 or 2. R8 (This refers to hydrocarbon, aryl, or heteroaryl groups with 1 to 12 carbon atoms.) Invention Effects According to the present invention, a novel fluorinated pyridine compound and a method for manufacturing the same are provided. Detailed Implementation

[0017] [Fluoropyridine compounds] The fluorinated pyridine compounds of the present invention are represented by the following general formula (a).

[0018] [Chemical Formula 8] (In general formula (a), A 1 And A 2 They are fluorine atoms or OR 1 However, when A 1 When A is a fluorine atom, 2 OR 1 , when A 1 OR 1 At that time, A 2 It is a fluorine atom; R 1 Hydrocarbon groups representing 1 to 12 carbon atoms; R 2 Indicates aryl, heteroaryl, cyano, -X-(Y) 1 n -R 4 ) m , or - (C=NR) 5 )-Y 2 -R 6 ,in, X represents CO, SO, SO2, or PO. Y 1 and Y 2 Each can be represented independently as O, S, or NR. 7 , n represents an integer that is either 0 or 1. m represents an integer of 1 or 2. R 4 R 5 R 6 R 7 Each of the 1 to 12 carbon atoms is represented independently by a hydrocarbon group. However, R 4 With R 7 R 5 With R 6 Or R 6 With R 7 They can also combine to form a ring; R 3 (This represents a hydrogen atom, or an alkyl, aryl, or heteroaryl group with 1 to 12 carbon atoms.) That is, the fluorinated pyridine compounds of the present invention are compounds represented by the following general formula (1) or (2).

[0019] [Chemical Formula 9] (In general formulas (1) and (2), R) 1 R 2 and R 3 As defined above. The fluorinated pyridine compound of the present invention has a trifluoromethyl group at the 3 position of the pyridine ring and a fluorine atom or OR at the 2 and 4 positions. 1 The compound has an electron-withdrawing group at position 5 and a hydrocarbon group at position 6. This novel compound is not only useful in the pharmaceutical and pesticide fields, but also shows promise in the field of organic electronic materials. Furthermore, due to its multiple substituents and high structural scalability, it can also be used as an intermediate to obtain various useful compounds. Therefore, the fluorinated pyridine compound of this invention makes a significant contribution to industry.

[0020] As R 1 R 4 R 5 R 6 R 7 The hydrocarbon groups, representing 1 to 12 carbon atoms respectively, are not particularly limited as long as they are composed of carbon and hydrogen atoms and have 1 to 12 carbon atoms. Examples include chain hydrocarbon groups, aromatic hydrocarbon groups, and alicyclic hydrocarbon groups. For chain hydrocarbon groups, the total number of carbon atoms is not particularly limited as long as it is 1 to 12; they can be straight-chain or branched. For aromatic hydrocarbon groups, the total number of carbon atoms is not particularly limited as long as it is 6 to 12; they can be aromatic hydrocarbon groups with or without substituents. It should be noted that in this case, the substituents can also be hydrocarbon substituents that bring the total number of carbon atoms in the aromatic hydrocarbon group to within the range of 6 to 12. Furthermore, aromatic hydrocarbon groups can also have fused polycyclic structures. For alicyclic hydrocarbon groups, the total number of carbon atoms is not particularly limited as long as it is 3 to 12; they can be alicyclic hydrocarbon groups with or without substituents. It should be noted that the substituent in this case can also be a hydrocarbon substituent that makes the total number of carbon atoms in the alicyclic hydrocarbon group fall within the range of 3 to 12. Additionally, the alicyclic hydrocarbon group can also have a bridged ring structure. The hydrocarbon group with 1 to 12 carbon atoms can also be an aralkyl group such as benzyl.

[0021] As R 1 R 4 R 5 R6 R 7 Examples of chain hydrocarbon groups that can be represented independently include alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl; alkenyl groups such as vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, and dodecenyl; and alkynyl groups such as ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, ocynyl, nonynyl, decynyl, undecynyl, and dodecynyl.

[0022] As R 1 R 4 R 5 R 6 R 7 Aromatic hydrocarbon groups that can be represented independently include phenyl, benzyl, tolyl, and naphthyl. Tolyl can be any one of o-tolyl, m-tolyl, and p-tolyl.

[0023] As R 1 R 4 R 5 R 6 R 7 Alicyclic hydrocarbon groups, represented independently, can be either saturated or unsaturated cyclic hydrocarbon groups. Examples of cyclic hydrocarbon groups include cyclopropyl, cyclobutyl, cyclohexyl, cyclopentyl, adamantyl, norbornyl, etc.

[0024] As R 1 Preferably, a chain hydrocarbon group or an aromatic hydrocarbon group is used; more preferably, a chain hydrocarbon group is used; even more preferably, a chain hydrocarbon group having 1 to 6 carbon atoms is used; even more preferably, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl is used; particularly preferably, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl is used; and most preferably, methyl or ethyl is used.

[0025] As R 4 R 5 R 6 R 7 Each of the following is preferred independently: a chain hydrocarbon group or an aromatic hydrocarbon group; more preferably, a chain hydrocarbon group or an aromatic hydrocarbon group having 1 to 8 carbon atoms; further preferred are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, or benzyl; particularly preferred are methyl, ethyl, n-propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, or benzyl; and most preferred are methyl, ethyl, isopropyl, or benzyl.

[0026] R 2 Indicates aryl, heteroaryl, cyano, -X-(Y) 1n -R 4 ) m , or - (C=NR) 5 )-Y 2 -R 6 Where X represents CO, SO, SO2, or PO, and Y represents... 1 and Y 2 Each can be represented independently as O, S, or NR. 7 In R, n represents an integer of 0 or 1, and m represents an integer of 1 or 2. 2 Preferably, it is a group with sufficient electron-withdrawing properties.

[0027] As R 2 Examples of aryl groups that can be represented include phenyl, tolyl, o-xylyl, m-xylyl, p-xylyl, and naphthyl. Preferably, the number of carbon atoms in the aryl group is in the range of 6 to 12.

[0028] As R 2 Examples of heteroaryl groups that can be represented include 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl, and indoleyl. Preferably, the total number of carbon atoms and heteroatoms in the heteroaryl group is in the range of 5 to 12.

[0029] In R 2 Represents -X-(Y) 1 n -R 4 ) m In typical cases, R 2 It is an ester of a carboxylic acid, sulfonic acid, sulfinic acid, or phosphonic acid; or a thioester of a carboxylic acid, sulfonic acid, sulfinic acid, or phosphonic acid; or an amide of a carboxylic acid, sulfonic acid, sulfinic acid, or phosphonic acid. In this case, R 2 Preferably, it is an ester of carboxylic acid, sulfonic acid, sulfinic acid or phosphonic acid, and more preferably an ester of carboxylic acid.

[0030] In R 2 Represents - (C=NR) 5 )-Y 2 -R 6 In typical cases, R 2 It is an ester of imine, a thioester of imine, or an amide (mididine) of imine. In this case, R is preferred. 2 It is an ester of imine.

[0031] In R 2 In the middle, R 4 With R 7 R 5 With R 6 Or R 6 With R 7 They can also combine to form a ring. R4 With R 7 R 5 With R 6 Or R 6 With R 7 The divalent hydrocarbon groups formed by their combination have a carbon number ranging from 2 to 24. R 4 With R 7 R 5 With R 6 Or R 6 With R 7 The divalent hydrocarbon groups formed by their combination can be either straight-chain or branched-chain. Additionally, R... 4 With R 7 R 5 With R 6 Or R 6 With R 7 The divalent hydrocarbon groups formed by their combination can have either aromatic or alicyclic structures. 4 With R 7 R 5 With R 6 Or R 6 With R 7 The number of carbon atoms in the divalent hydrocarbon groups formed by their combination is preferably in the range of 2 to 12, more preferably in the range of 2 to 12, and even more preferably in the range of 2 to 6.

[0032] R 3 It represents a hydrogen atom, or an alkyl, aryl, or heteroaryl group with 1 to 12 carbon atoms.

[0033] As R 3 Alkyl groups with 1 to 12 carbon atoms can be represented, including methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl. Among these, alkyl groups with 1 to 8 carbon atoms are preferred, alkyl groups with 1 to 6 carbon atoms are more preferred, alkyl groups with 1 to 4 carbon atoms are even more preferred, and methyl or ethyl groups are particularly preferred.

[0034] As R 3 Examples of aryl groups that can be represented include phenyl, tolyl, o-xylyl, m-xylyl, p-xylyl, and naphthyl. Preferably, the number of carbon atoms in the aryl group is in the range of 6 to 12.

[0035] As R 3 Examples of heteroaryl groups that can be represented include 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl, and indoleyl. Preferably, the total number of carbon atoms and heteroatoms in the heteroaryl group is in the range of 5 to 12.

[0036] In one embodiment, the fluorinated pyridine compound may be the following compound: A 1 A is a fluorine atom. 2 OR 1 R 1 The derivatives are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl, R. 2 For -X-(Y) 1 n -R 4 ) m R 3 It can be hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, phenyl, tolyl, o-xylyl, m-xylyl, p-xylyl, naphthyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thiophenyl, 3-thiophenyl, 2-furanyl, 3-furanyl, or indoleyl.

[0037] In one embodiment, the fluorinated pyridine compound may be the following compound: A 1 OR 1 A 2 R is a fluorine atom. 1 The derivatives are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl, R. 2 It is phenyl, tolyl, o-xylyl, m-xylyl, p-xylyl, naphthyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thiophenyl, 3-thiophenyl, 2-furanyl, 3-furanyl, or indoleyl, R 3 It can be hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, phenyl, tolyl, o-xylyl, m-xylyl, p-xylyl, naphthyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thiophenyl, 3-thiophenyl, 2-furanyl, 3-furanyl, or indoleyl.

[0038] (use) The compounds of the present invention are useful in the fields of medicine, pesticides, and organic electronic materials. They can also be used as intermediates for obtaining more useful compounds. The compounds of the present invention can be used in the form of salts. Examples of salts in this case include hydrochlorides, hydrobroms, acetates, and sulfates.

[0039] As for the applications of the compounds of the present invention in the field of pesticides, examples include their use as pest control agents, arthropod control agents, and herbicides. For example, as pest control agents, the compounds of the present invention can be used to control a variety of fungi attached to various cultivated plants, vegetables, and the seeds of these plants. Cultivated plants include wheat, rye, barley, oats, rice, corn, pasture, bananas, cotton, soybeans, coffee trees, sugarcane, grapevines, fruit trees, and foliage plants, while vegetables include cucumbers, beans, tomatoes, potatoes, and melons.

[0040] The compounds of the present invention are applicable, for example, to the prevention and control of the following plant diseases caused by harmful fungi: Rice diseases include rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), and sheath blight (Rhizoctonia solani); wheat diseases include powdery mildew (Erysiphe graminis), Fusarium head blight (Gibberella zeae), red rust (Puccinia striiformis, P. graminis, P. recondita, P. hordei), snow mold (Typhula sp., Micronectriella nivalis), loose smut (Ustilagotritici, U. nuda), taenia caries, eye blight (Pseudocercosporella herpotrichoides), cloud blight (Rhynchosporium secalis), leaf blight (Septoria tritici), leptospirosis (Leptosphaeria nodorum), and net blight (Pyrenophora). Diseases affecting citrus fruits include: teres (a type of citrus disease), stripe disease (Helminthosporium zonatum Ikata); black spot disease (Diaporthe citri), scab disease (Elsinoe fawcetti), fruit rot disease (Penicillium digitatum, P. italicum), brown rot disease (Phytophthora citrophthora, P. nicotianae), black spot disease (Phyllostictina citricarpa), and canker disease (Xanthomonas citri); and flower rot disease (Monilinia mali), rot (Valsa mali), powdery mildew (Podosphaera leucotricha), leaf spot disease (Alternaria mali), black spot disease (Venturiainaequalis), black spot disease (Mycosphaerella pomi), anthracnose (Colletotrichum acutatum), ring spot disease (Botryosphaeria berengeriana), and red spot disease (Gymnosporangium). Phytozoanthosis (Yamadae), gray spot disease (Monilinia fructicola), etc.; pear black spot disease (Venturia nashicola, V).Pirina, black spot (Alternaria kikuchiana), red spot (Gymnosporangium haraeanum), gray spot (Monilinia fructicola), etc.; peach gray spot (Monilinia fructicola), black spot (Cladosporium carpophilum), Phopsis sp., etc.; grape black rot (Elsinoe ampelina), late rot (Colletotrichum acutatum), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), black rot (Guignardia bidwellii), downy mildew (Plasmopara viticola), gray spot (Monilinia fructigena), black spot (Cladosporium viticolum), gray mold (Botrytiscinerea), etc.; persimmon anthracnose (Gloeosporium kaki), leaf drop (Cercospora kaki, Mycosphaerella), etc. nawae; Anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea, Oidiopsis taurica), vine blight (Didymella bryoniae), vine rot (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), blight (Phytophthorasp.), damping-off (Pythium sp.).Diseases affecting tomatoes include: leaf spot (Alternaria solani), leaf mold (Cladosporium fulvum), blight (Phytophthora infestans), and root rot (Fusarium solani); brown spot (Phomopsis vexans) and powdery mildew (Erysiphe cichoracearum) in eggplants; black spot (Alternaria japonica), white spot (Cercosporella brassicae), and soft rot (Erwinia carotovora) in cruciferous vegetables; rust (Puccinia allii) in onions; and purple spot (Cercospora kikuchii), black rot (Elsinoe glycines), and black spot (Diaporthe phaseolorum var.) in soybeans.Sojae, etc.; anthracnose of beans (Colletotrichum lindemuthianum), etc.; black spot disease of peanuts (Cercospora personata), brown spot disease (Cercospora arachidicola), etc.; powdery mildew of peas (Erysiphe pisi), etc.; early blight (Alternaria solani), blight (Phytophthora infestans), leaf rot (Rhizoctonia solani), etc. of potatoes; powdery mildew (Sphaerotheca humuli) of strawberries, etc.; net cake disease (Exobasidium reticulatum), white star disease (Elsinoe leucospila), etc. of tea; red star disease (Alternaria longipes), powdery mildew (Erysiphecichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), blight (Phytophthora), etc. of tobacco. Diseases affecting various crops include: * Nicotianae* and *Pseudomonas syringae* (wildfire); *Cercospora beticola* (brown spot) and *Aphanomyces cochlioides* (seedling blight) in sugar beets; *Diplocarpon rosae* (black spot) and *Sphaerotheca pannosa* (powdery mildew) in roses; *Septoriachrysanthemi-indici* (brown spot) and *Puccinia horiana* (white rust) in chrysanthemums; and gray mold (Botrytiscinerea) and sclerotinia sclerotiorum (sclerotinia sclerotiorum) in various crops.

[0041] When applying harmful fungal control agents, they can be used directly in their pure form without adding other components to the fluorinated pyridine compounds or their salts of the present invention. They can also be used in common pesticide forms, such as solid formulations (granules, powders, broad-area dispersible agents, or powdered products), and liquid formulations (wettable powders, emulsions, water-soluble solutions, pastes, oil dispersions, dispersible formulations, emulsions, oils, aerosols, sprays, or flowable formulations). While the application form is determined according to its specific purpose, in all cases, it is preferred that the fluorinated pyridine compounds or their salts of the present invention be finely and uniformly dispersed.

[0042] Harmful bacteria control agents can also be prepared as follows: as needed, by using emulsifiers or dispersants or other auxiliaries, the fluorinated pyridine compound or its salt of the present invention is applied to a solvent and / or a solid carrier.

[0043] [Method for manufacturing fluorinated pyridine compounds] As specific examples of the method for manufacturing the fluorinated pyridine compound of the present invention, the following methods (A) to (D) can be cited.

[0044] (A) A method having the following steps: obtaining a fluorinated pyridine compound represented by general formula (1) by reacting a fluorinated isobutylene derivative represented by general formula (3) with a compound or a salt thereof represented by general formula (4).

[0045] [Chemical Formula 10] (In general formulas (1), (3) and (4), R 1 Hydrocarbon groups representing 1 to 12 carbon atoms; R 2 Indicates aryl, heteroaryl, cyano, -X-(Y) 1 n -R 4 ) m , or - (C=NR) 5 )-Y 2 -R 6 ,in, X represents CO, SO, SO2, or PO. Y 1 and Y 2 Each can be represented independently as O, S, or NR. 7 , n represents an integer that is either 0 or 1. m represents an integer of 1 or 2. R 4 R 5 R 6 R 7 Each of the 1 to 12 carbon atoms is represented independently by a hydrocarbon group. However, R 4 With R 7 R 5 With R 6 Or R 6 With R 7 They can also combine to form a ring; R 3 (This represents a hydrogen atom, or an alkyl, aryl, or heteroaryl group with 1 to 12 carbon atoms.) (B) A method comprising the steps of: obtaining a fluorinated pyridine compound represented by general formula (1) by reacting a fluoroisobutane derivative represented by general formula (5) with a compound or a salt thereof represented by general formula (4).

[0046] [Chemical Formula 11] (In general formulas (1), (4) and (5), R) 1 R 2 and R 3 As defined above. (C) A method comprising the step of obtaining a fluorinated pyridine compound represented by general formula (2) by reacting a fluorinated isobutylene derivative represented by general formula (3) with a compound or a salt thereof represented by general formula (6).

[0047] [Chemical Formula 12] (In general formulas (2), (3) and (6), R) 1 R 2 and R 3 As defined above, Z represents cyano or -V-(O) l -R 8 ) k ,in, V represents SO, SO2, or PO. l represents an integer that is either 0 or 1. k represents an integer of 1 or 2. R 8 (This refers to hydrocarbon, aryl, or heteroaryl groups with 1 to 12 carbon atoms.) (D) A method having the following steps: obtaining a fluorinated pyridine compound represented by general formula (2) by reacting a fluoroisobutane derivative represented by general formula (5) with a compound or a salt thereof represented by general formula (6).

[0048] [Chemical Formula 13] (In general formulas (2), (5) and (6), R) 1 R 2 R 3 And Z as defined above. Generally, the synthesis of fluorinated compounds can be broadly divided into methods starting from raw materials that already contain fluorine (modular methods) and methods that introduce fluorine into the compound. The former method is characterized by the fluorine introduction site being dependent on the raw material. Furthermore, the latter method, under the reaction conditions for introducing fluorine, can only use raw materials with coexisting substituents, or often requires pre-introducing "labeling" such as bromine or iodine at the fluorine introduction site, resulting in low efficiency. In the manufacturing method of the present invention, by employing the methods described in (A) to (D) above, novel fluorinated pyridine compounds (fluorinated pyridine compounds of the present invention) can be obtained at sites difficult to introduce fluorine in conventional methods. Moreover, the manufacturing method of the present invention is a modular method, which can efficiently obtain fluorinated pyridine compounds without using expensive halogen elements.

[0049] In methods (A) and (B) above, HF is removed via a reaction. Furthermore, in methods (C) and (D) above, both HF and HZ are removed via a reaction.

[0050] In methods (C) and (D) above, Z represents cyano or -V-(O) l -R 8 ) k In Z, -V- (O l -R 8 ) k In this case, V is preferably SO2 (sulfonyl), l is 0, and k is 1.

[0051] In Z, -V-(O) l -R 8 ) k R in the case 8 This indicates a hydrocarbon group, aryl group, or heteroaryl group with 1 to 12 carbon atoms. As R 8 Preferably, it is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, phenyl, tolyl, o-xylyl, m-xylyl, p-xylyl, naphthyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thiophenyl, 3-thiophenyl, 2-furanyl, 3-furanyl, or indoleyl.

[0052] In the methods (A) to (D) above, the compounds represented by general formula (4) or (6) can also be in the form of salts. In the case of being in the form of salts, the amino group (-NH2) of the compound of general formula (4) or (6) is cationized to become (-NH3). + And, it forms a salt with the counter ion. The counter ion is not particularly limited as long as it is a monovalent anion; for example, F... - Cl - ,Br - I -Isohalide ions. From the viewpoint of availability, the preferred salt is the hydrochloride salt.

[0053] The compounds represented by the above general formulas (3) to (6) can be commercially available compounds or compounds manufactured by known methods, etc.

[0054] In the methods (A) to (D) above, the reaction can also be carried out in the presence of an organic solvent. Examples of usable organic solvents include ethers such as tetrahydrofuran, diethyl ether, dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, and tetraethylene glycol dimethyl ether; aliphatic hydrocarbons such as hexane, heptane, octane, and isooctane; aromatic hydrocarbons such as benzene, toluene, xylene, and ethylbenzene; nitriles such as acetonitrile; and aprotic polar solvents such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone, dimethylvinylurea, tetramethylurea, dimethyl sulfoxide, and sulfolane.

[0055] In the methods (A) to (D) above, the reaction can also be carried out in the presence of an alkaline substance. Examples of alkaline substances that can be used include alkali metal / alkaline earth metal hydroxides such as sodium hydroxide, potassium hydroxide, calcium hydroxide, lithium hydroxide, magnesium hydroxide, and barium hydroxide; alkali metal / alkaline earth metal carbonates such as sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate; metal hydrides such as sodium hydride, potassium hydride, and calcium hydride; tertiary amines such as trimethylamine, triethylamine, N,N-diisopropylethylamine, diazabicycloundecene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 2-tert-butyl-1,1,3,3-tetramethylguanidine, and N,N-dimethylaniline; and phosphazene bases such as P1-t-Bu, P2-t-Bu, P3-t-Bu, and P4-t-Bu.

[0056] In the methods (A) to (D) above, two basic substances can also be used to carry out the reaction in two stages. For example, the following two-stage reaction can also be adopted: in the first stage, a milder base is used to generate an intermediate, and then in the second stage, a stronger base than the one used in the first stage (e.g., phosphazene base) is used to obtain the final product.

[0057] The reaction temperature in methods (A) to (D) above is preferably -20°C or higher and lower than the boiling point of the organic solvent, more preferably 0 to 50°C, and even more preferably 10 to 30°C. The reaction time in methods (A) to (D) above is preferably 0.5 to 48 hours, more preferably 1 to 36 hours, and even more preferably 10 to 25 hours.

[0058] The above describes some embodiments of the present invention, but the present invention is not limited to the above embodiments, but includes the concept of the present invention and all forms contained in the claims, and various modifications can be made within the scope of the present invention.

[0059] Example The present invention will now be described in more detail through examples, etc., but the present invention is not limited to these examples, etc.

[0060] (Example 1) [Preparation of methyl 6-fluoro-4-methoxy-2-methyl-5-trifluoromethyl-3-pyridinium carboxylate] 1.1 g (9.6 mmol) of methyl 3-amino-2-butenoate, 3.7 g (29 mmol) of N,N-diisopropylethylamine, and 2.0 g (9.6 mmol) of 1,3,3,3-tetrafluoro-1-methoxy-2-(trifluoromethyl)-1-propene were added to 60 g of toluene, and the mixture was heated to reflux. After approximately 16 hours, the contents were purified by silica gel column chromatography to give 0.8 g of the following compound. The yield was 31%.

[0061] [Chemical Formula 14] The analysis results are as follows.

[0062] Mass spectrometry (APCI, m / z): 267 ([M]) + ) 1 H-NMR (400MHz, CDCl3) d ppm: 3.99 (s, 3H), 3.97 (s, 3H), 2.51 (s, 3H) (Example 2) [Preparation of ethyl 6-fluoro-4-methoxy-2-methyl-5-trifluoromethyl-3-pyridinecarboxylate] 1.2 g (9.3 mmol) of ethyl 3-amino-2-butenoate, 4.8 g (37 mmol) of N,N-diisopropylethylamine, and 2.2 g (9.3 mmol) of 1,1,1,3,3-pentafluoro-3-methoxy-2-(trifluoromethyl)-propane were added to 75 g of hexane, and the mixture was heated to reflux. After approximately 12 hours, the contents were purified by silica gel column chromatography to give 0.7 g of the following compound. The yield was 25%.

[0063] [Chemical Formula 15] The analysis results are as follows.

[0064] Mass spectrometry (APCI, m / z): 281 ([M]) + ) 1 H-NMR (400MHz, CDCl3) dppm: 4.45 (q, 2H), 3.98 (s, 3H), 2.51 (s, 3H), 1.42 (t, 3H) (Example 3) [Preparation of 1-methyl ethyl 6-fluoro-4-methoxy-2-methyl-5-trifluoromethyl-3-pyridinic acid] 1.1 g (7.7 mmol) of 1-methyl ethyl 3-amino-2-butenoic acid, 2.3 g (23 mmol) of triethylamine, and 1.6 g (7.7 mmol) of 1,3,3,3-tetrafluoro-1-methoxy-2-(trifluoromethyl)-1-propene were added to 65 g of heptane, and the mixture was heated to reflux. After approximately 24 hours, the contents were purified by silica gel column chromatography to give 0.4 g of the following compound. The yield was 19%.

[0065] [Chemical Formula 16] The analysis results are as follows.

[0066] Mass spectrometry (APCI, m / z): 295 ([M]) + ) 1 H-NMR (400MHz, CDCl3) d ppm: 5.33 (sep, 1H), 3.99 (s, 3H), 2.51 (s, 3H), 1.41 (d, 6H) (Example 4) [Preparation of benzyl 6-fluoro-4-methoxy-2-methyl-5-trifluoromethyl-3-pyridinecarboxylate] 1.5 g (7.8 mmol) of benzyl 3-amino-2-butenoate, 2.4 g (24 mmol) of triethylamine, and 1.7 g (7.8 mmol) of 1,3,3,3-tetrafluoro-1-methoxy-2-(trifluoromethyl)-1-propene were added to 60 g of ethylbenzene, and the mixture was heated to reflux. After approximately 9 hours, the contents were purified by silica gel column chromatography to give 0.3 g of the following compound. The yield was 12%.

[0067] [Chemical Formula 17] The analysis results are as follows.

[0068] Mass spectrometry (APCI, m / z): 343 ([M]) + ) (Example 5) [Preparation of ethyl 2-ethyl-6-fluoro-4-methoxy-5-trifluoromethyl-3-pyridinecarboxylate] 1.5 g (12 mmol) of ethyl 3-amino-2-pentenoate, 4.5 g (35 mmol) of N,N-diisopropylethylamine, and 2.5 g (12 mmol) of 1,3,3,3-tetrafluoro-1-methoxy-2-(trifluoromethyl)-1-propene were added to 80 g of isooctane, and the mixture was heated to reflux. After approximately 10 hours, the contents were purified by silica gel column chromatography to give 1.4 g of the following compound. The yield was 39%.

[0069] [Chemical Formula 18] The analysis results are as follows.

[0070] Mass spectrometry (APCI, m / z): 295 ([M]) + ) 1 H-NMR (400MHz, CDCl3) d ppm: 4.43 (q, 2H), 3.96 (s, 3H), 2.73 (q, 2H), 1.40 (t, 3H), 1.27 (t, 3H) (Example 6) [Preparation of ethyl 6-fluoro-4-methoxy-2-(2-pyridyl)-5-trifluoromethyl-3-pyridinecarboxylate] 1.0 g (5.2 mmol) of ethyl 3-amino-3-(2-pyridyl)-2-acrylate, 2.0 g (16 mmol) of N,N-diisopropylethylamine, and 1.1 g (5.2 mmol) of 1,3,3,3-tetrafluoro-1-methoxy-2-(trifluoromethyl)-1-propene were added to 80 g of heptane, and the mixture was heated to reflux. After approximately 12 hours, the contents were purified by silica gel column chromatography to give 0.2 g of the following compound. The yield was 9%.

[0071] [Chemical Formula 19] The analysis results are as follows.

[0072] Mass spectrometry (APCI, m / z): 344 ([M]) + ) (Example 7) [Preparation of 4-fluoro-2-methoxy-5-phenyl-3-(trifluoromethyl)pyridine] Phase 1 Under ice-water cooling, 1.0 g (3.4 mmol) of 2-phenyl-2-(benzenesulfonyl)ethylamine hydrochloride and 0.7 g (3.4 mmol) of 1,3,3,3-tetrafluoro-1-methoxy-2-(trifluoromethyl)-1-propene were added to 50 g of tetrahydrofuran. Then, 0.9 g (6.7 mmol) of N,N-diisopropylethylamine was added dropwise at an internal temperature not exceeding 10 °C, and the mixture was heated to room temperature. After approximately 16 hours, the contents were purified by silica gel column chromatography to obtain 1.0 g of methyl 3,3,3-trifluoro-N-(2-phenyl-2-(benzenesulfonyl)ethyl)-2-(trifluoromethyl)propaneimine, shown below as an intermediate. The yield was 67%.

[0073] [Chemical Formula 20] The analysis results are as follows.

[0074] Mass spectrometry (APCI, m / z): 453 ([M]) + ) Phase Two Under ice-water cooling, 1.0 g (2.3 mmol) of methyl 3,3,3-trifluoro-N-(2-phenyl-2-(benzenesulfonyl)ethyl)-2-(trifluoromethyl)propaneimine and 2.3 g (6.8 mmol) of sodium tetraphenylborate were added to 60 g of tetrahydrofuran. Then, 8.5 mL (6.8 mmol) of phosphazene base P4-t-Bu hexane solution (0.8 M) was added dropwise at an internal temperature not exceeding 10 °C, and the mixture was heated to room temperature. After approximately 16 hours, the contents were purified by silica gel column chromatography to obtain 12 mg of the following compound. The yield was 2%.

[0075] [Chemical Formula 21] The analysis results are as follows.

[0076] Mass spectrometry (APCI, m / z): 271 ([M]) + ) (Example 8) [Preparation of 4-fluoro-5-(2-furanyl)-2-methoxy-3-(trifluoromethyl)pyridine] Phase 1 Under ice-water cooling, 1.1 g (3.7 mmol) of 2-(2-furanyl)-2-(2-thienylsulfonyl)ethylamine hydrochloride and 0.9 g (3.7 mmol) of 1,1,1,3,3-pentafluoro-3-methoxy-2-(trifluoromethyl)-propane were added to 50 g of tetrahydrofuran. Then, 1.1 g (11 mmol) of triethylamine was added dropwise at an internal temperature not exceeding 10 °C, and the mixture was heated to room temperature. After approximately 16 hours, the contents were purified by silica gel column chromatography to obtain 1.2 g of methyl 3,3,3-trifluoro-N-(2-(2-furanyl)-2-(2-thienylsulfonyl)ethyl)-2-(trifluoromethyl)propane imine, shown below as an intermediate. The separation yield was 75%.

[0077] [Chemical Formula 22] The analysis results are as follows.

[0078] Mass spectrometry (APCI, m / z): 449 ([M]) + ) Phase Two Under ice-water cooling, 1.2 g (2.8 mmol) of methyl 3,3,3-trifluoro-N-(2-(2-furanyl)-2-(2-thienylsulfonyl)ethyl)-2-(trifluoromethyl)propaneimide and 2.4 g (8.3 mmol) of lithium bis(trifluoromethanesulfonyl)imide were added to 60 g of tetrahydrofuran. Then, 10 mL (8.3 mmol) of phosphazene base P4-t-Bu hexane solution (0.8 M) was added dropwise at an internal temperature not exceeding 10 °C, and the mixture was heated to room temperature. After approximately 16 hours, the contents were purified by silica gel column chromatography to obtain 4 mg of the following compound. The yield was 0.5%.

[0079] [Chemical Formula 23] The analysis results are as follows.

[0080] Mass spectrometry (APCI, m / z): 261 ([M]) + ) (Example 9) [Preparation of 4-fluoro-2-methoxy-5-thienyl-3-(trifluoromethyl)pyridine] Phase 1 Under ice-water cooling, 1.0 g (3.2 mmol) of 2-(2-thienyl)-2-(2-thienylsulfonyl)ethylamine hydrochloride and 0.7 g (3.2 mmol) of 1,3,3,3-tetrafluoro-1-methoxy-2-(trifluoromethyl)-1-propene were added to 40 g of tetrahydrofuran. Then, 5.0 g (6.5 mmol) of N,N-diisopropylethylamine was added dropwise at an internal temperature not exceeding 10 °C, and the mixture was heated to room temperature. After approximately 16 hours, the contents were purified by silica gel column chromatography to obtain 1.2 g of methyl 3,3,3-trifluoro-N-(2-(2-thienyl)-2-(2-thienylsulfonyl)ethyl)-2-(trifluoromethyl)propaneimine, shown below as an intermediate. The separation yield was 81%.

[0081] [Chemical Formula 24] The analysis results are as follows.

[0082] Mass spectrometry (APCI, m / z): 465 ([M]) + ) Phase Two Under ice-water cooling, 1.2 g (2.6 mmol) of methyl 3,3,3-trifluoro-N-(2-(2-thienyl)-2-(2-thienylsulfonyl)ethyl)-2-(trifluoromethyl)propaneimide and 2.2 g (7.8 mmol) of lithium bis(trifluoromethanesulfonyl)imide were added to 60 g of tetrahydrofuran. Then, 9.8 mL (7.8 mmol) of phosphazene base P4-t-Bu hexane solution (0.8 M) was added dropwise at an internal temperature not exceeding 10 °C, and the mixture was heated to room temperature. After approximately 16 hours, the contents were purified by silica gel column chromatography to obtain 7 mg of the following compound. The yield was 1%.

[0083] [Chemical Formula 25] The analysis results are as follows.

[0084] Mass spectrometry (APCI, m / z): 277 ([M]) + ) (Example 10) [Preparation of 6-fluoro-4-methoxy-2-methyl-5-trifluoromethyl-3-pyridinecarboxylic acid and (2E)-3-phenyl-2-propen-1-yl ester] 0.5 g (2.3 mmol) of 3-aminocrotonic acid cinnamyl ester was dissolved in 23 mL of heptane, 0.6 g (4.8 mmol) of N,N-diisopropylethylamine was added and the mixture was cooled to 0 °C. Then, 0.5 g (2.4 mmol) of 2-(trifluoromethyl)-3,3,3-trifluoropropionate methyl ester was added. After stirring under reflux for 24.2 hours, the contents were purified by silica gel column chromatography to obtain the following compound.

[0085] [Chemical Formula 26] The analysis results are as follows.

[0086] Mass spectrometry (APCI, m / z): 369.1 ([M]) + ) (Example 11) [Preparation of methyl 2-ethyl-6-fluoro-4-methoxy-5-trifluoromethyl-3-pyridinium carboxylate] 0.5 g (4.0 mmol) of methyl 3-aminopent-2-enoate was dissolved in 39 mL of heptane. 1.5 g (11.7 mmol) of N,N-diisopropylethylamine was added and the mixture was cooled to 0 °C. Then, 0.9 g (4.0 mmol) of methyl 2-(trifluoromethyl)-3,3,3-trifluoropropionate was added. After stirring under reflux for 16.7 hours, the contents were purified by silica gel column chromatography to obtain the following compound.

[0087] [Chemical Formula 27] The analysis results are as follows.

[0088] Mass spectrometry (APCI, m / z): 281.4 ([M]) + ) (Example 12) [Preparation of propyl 6-fluoro-4-methoxy-2-methyl-5-trifluoromethyl-3-pyridinylcarboxylate] 0.5 g (3.6 mmol) of propyl 3-aminobutyric acid was dissolved in 35 mL of heptane. 1.4 g (10.5 mmol) of N,N-diisopropylethylamine was added and the mixture was cooled to 0 °C. Then, 0.8 g (3.6 mmol) of methyl 2-(trifluoromethyl)-3,3,3-trifluoropropionate was added. After stirring under reflux for 21.2 hours, the contents were purified by silica gel column chromatography to obtain the following compound.

[0089] [Chemical Formula 28] The analysis results are as follows.

[0090] Mass spectrometry (APCI, m / z): 295.4 ([M]) + ) As can be seen from the above, the novel fluorinated pyridine compound of the present invention can be manufactured.

[0091] Industrial utilization potential The fluorinated pyridine compounds of the present invention can be suitably used in the fields of medicine, pesticides, and organic electronic materials. Furthermore, due to their multiple substituents and high structural extensibility, they can also be used as intermediates for various useful compounds.

Claims

1. A fluorinated pyridine compound represented by the following general formula (a), [Chemical Formula 1] In general formula (a), A 1 And A 2 They are fluorine atoms or OR 1 However, when A 1 When A is a fluorine atom, 2 OR 1 , when A 1 OR 1 At that time, A 2 It is a fluorine atom; R 1 Hydrocarbon groups representing 1 to 12 carbon atoms; R 2 Indicates aryl, heteroaryl, cyano, -X-(Y) 1 n -R 4 ) m , or - (C=NR) 5 )-Y 2 -R 6 ,in, X represents CO, SO, SO2, or PO. Y 1 and Y 2 Each can be represented independently as O, S, or NR. 7 , n represents an integer that is either 0 or 1. m represents an integer of 1 or 2. R 4 R 5 R 6 R 7 Each of the 1 to 12 carbon atoms is represented independently by a hydrocarbon group. However, R 4 With R 7 R 5 With R 6 Or R 6 With R 7 They can also combine to form a ring; R 3 It represents a hydrogen atom, or an alkyl, aryl, or heteroaryl group with 1 to 12 carbon atoms.

2. The fluorinated pyridine compound according to claim 1, which is represented by the following general formula (1), [Chemical Formula 2] In general formula (1), R 1 R 2 and R 3 As described in claim 1.

3. The fluorinated pyridine compound according to claim 1, which is represented by the following general formula (2), [Chemical Formula 3] In general formula (2), R 1 R 2 and R 3 As described in claim 1.

4. A method for manufacturing a fluorinated pyridine compound, comprising the following steps: obtaining a fluorinated pyridine compound represented by general formula (1) by reacting a fluorinated isobutylene derivative represented by general formula (3) with a compound or its salt represented by general formula (4). [Chemical Formula 4] In general formulas (1), (3) and (4), R 1 Hydrocarbon groups representing 1 to 12 carbon atoms; R 2 Indicates aryl, heteroaryl, cyano, -X-(Y) 1 n -R 4 ) m , or - (C=NR) 5 )-Y 2 -R 6 ,in, X represents CO, SO, SO2, or PO. Y 1 and Y 2 Each can be represented independently as O, S, or NR. 7 , n represents an integer that is either 0 or 1. m represents an integer of 1 or 2. R 4 R 5 R 6 R 7 Each of the 1 to 12 carbon atoms is represented independently by a hydrocarbon group. However, R 4 With R 7 R 5 With R 6 Or R 6 With R 7 They can also combine to form a ring; R 3 It represents a hydrogen atom, or an alkyl, aryl, or heteroaryl group with 1 to 12 carbon atoms.

5. A method for manufacturing a fluorinated pyridine compound, comprising the following steps: obtaining a fluorinated pyridine compound represented by general formula (1) by reacting a fluorinated isobutane derivative represented by general formula (5) with a compound represented by general formula (4) or a salt thereof. [Chemical Formula 5] In general formulas (1), (4) and (5), R 1 Hydrocarbon groups representing 1 to 12 carbon atoms; R 2 Indicates aryl, heteroaryl, cyano, -X-(Y) 1 n -R 4 ) m , or - (C=NR) 5 )-Y 2 -R 6 ,in, X represents CO, SO, SO2, or PO. Y 1 and Y 2 Each can be represented independently as O, S, or NR. 7 , n represents an integer that is either 0 or 1. m represents an integer of 1 or 2. R 4 R 5 R 6 R 7 Each of the 1 to 12 carbon atoms is represented independently by a hydrocarbon group. However, R 4 With R 7 R 5 With R 6 Or R 6 With R 7 They can also combine to form a ring; R 3 It represents a hydrogen atom, or an alkyl, aryl, or heteroaryl group with 1 to 12 carbon atoms.

6. A method for manufacturing a fluorinated pyridine compound, comprising the following steps: obtaining a fluorinated pyridine compound represented by general formula (2) by reacting a fluorinated isobutylene derivative represented by general formula (3) with a compound or a salt thereof represented by general formula (6). [Chemical Formula 6] In general formulas (2), (3) and (6), R 1 Hydrocarbon groups representing 1 to 12 carbon atoms; R 2 Indicates aryl, heteroaryl, cyano, -X-(Y) 1 n -R 4 ) m , or - (C=NR) 5 )-Y 2 -R 6 ,in, X represents CO, SO, SO2, or PO. Y 1 and Y 2 Each can be represented independently as O, S, or NR. 7 , n represents an integer that is either 0 or 1. m represents an integer of 1 or 2. R 4 R 5 R 6 R 7 Each of the 1 to 12 carbon atoms is represented independently by a hydrocarbon group. However, R 4 With R 7 R 5 With R 6 Or R 6 With R 7 They can also combine to form a ring; R 3 It represents a hydrogen atom, or an alkyl, aryl, or heteroaryl group having 1 to 12 carbon atoms; Z represents cyano or -V-(O) l -R 8 ) k ,in, V represents SO, SO2, or PO. l represents an integer that is either 0 or 1. k represents an integer of 1 or 2. R 8 It represents a hydrocarbon group, aryl group, or heteroaryl group with 1 to 12 carbon atoms.

7. A method for manufacturing a fluorinated pyridine compound, comprising the following steps: obtaining a fluorinated pyridine compound represented by general formula (2) by reacting a fluorinated isobutane derivative represented by general formula (5) with a compound or a salt thereof represented by general formula (6). [Chemical Formula 7] In general formulas (2), (5) and (6), R 1 Hydrocarbon groups representing 1 to 12 carbon atoms; R 2 Indicates aryl, heteroaryl, cyano, -X-(Y) 1 n -R 4 ) m , or - (C=NR) 5 )-Y 2 -R 6 ,in, X represents CO, SO, SO2, or PO. Y 1 and Y 2 Each can be represented independently as O, S, or NR. 7 , n represents an integer that is either 0 or 1. m represents an integer of 1 or 2. R 4 R 5 R 6 R 7 Each of the 1 to 12 carbon atoms is represented independently by a hydrocarbon group. However, R 4 With R 7 R 5 With R 6 Or R 6 With R 7 They can also combine to form a ring; R 3 It represents a hydrogen atom, or an alkyl, aryl, or heteroaryl group having 1 to 12 carbon atoms; Z represents cyano or -V-(O) l -R 8 ) k ,in, V represents SO, SO2, or PO. l represents an integer that is either 0 or 1. k represents an integer of 1 or 2. R 8 It represents a hydrocarbon group, aryl group, or heteroaryl group with 1 to 12 carbon atoms.

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