Fluorinated pyridine compound and method for producing same

Abstract

Provided are: a novel fluorinated pyridine compound; and a method for producing the same.　The fluorinated pyridine compound is represented by general formula (a). (In the formula, A1 and A2 each independently represent a fluorine atom or OR1, wherein A2 is OR1 when A1 is a fluorine atom and A2 is a fluorine atom when A1 is OR1; R1 represents a hydrocarbon group having 1 to 12 carbon atoms; R2 represents an aryl group, a heteroaryl group, a cyano group, -X-(Y1 n-R4)m, or -(C=NR5)-Y2-R6; and R3 represents a hydrogen atom, or an alkyl, aryl, or heteroaryl group having 1 to 12 carbon atoms.)

Description

Fluorine-containing pyridine compound and method for producing the same

[0001] The present invention relates to a fluorine-containing pyridine compound and a method for producing the same.

[0002] Compounds containing a pyridine ring structure play important roles in the biological activities of a wide range of organisms, from eukaryotes to prokaryotes. Specifically, nicotinamide adenine dinucleotide and pyridoxal phosphate, which contain pyridine ring structures, are known to be essential cofactors for the activation of various enzymes. Against this background, numerous pharmaceuticals containing pyridine ring structures have been developed. Specific examples of such pharmaceuticals include the antituberculosis drug isoniazid and the antibiotic ceftazidime. Compounds containing pyridine ring structures are also widely used in agriculture, for example, as pesticides for harmful fungi (fungicides), arthropod control agents (insecticides), and herbicides. Specific examples of pesticides containing pyridine ring structures include the insecticide chlorpyrifos and the fungicide boscalid.

[0003] Furthermore, in recent years, there has been interest in improving activity by introducing a fluorine atom and / or a fluorine-containing substituent into the pyridine ring.Specific examples of known pharmaceuticals include mefloquine, an antimalarial drug having a 2-trifluoromethylpyridine partial structure, and enoxacin, an antibacterial drug having a 3-fluoropyridine partial structure, and examples of known agricultural chemicals include fluazinam, a fungicide having a 3-trifluoromethylpyridine partial structure, and fluoxypyr, a herbicide having a 2-fluoropyridine partial structure.

[0004] Patent Document 1 discloses a useful method for producing a fluorine-containing pyrimidine compound having a structure related to a fluorine-containing pyridine compound.

[0005] International Publication No. 2020 / 116296

[0006] Although compounds having a structure in which a trifluoromethyl group is located at the 3-position of a pyridine ring are useful not only in the fields of pharmaceuticals and agrochemicals but also in the field of organic electronic materials, there have been very few reports of such compounds and their production methods. Therefore, providing a novel and easily producible compound having a trifluoromethyl group located at the 3-position of a pyridine ring is itself highly valuable. Furthermore, while such compounds may be useful in themselves, when they have multiple substituents in addition to the trifluoromethyl group, they have high structural expandability and can be expected to serve as useful intermediates for obtaining further compounds.

[0007] The present invention provides a novel fluorine-containing pyridine compound and a method for producing the same.

[0008] The present invention provides the following essential features: [1] A fluorine-containing pyridine compound represented by the following general formula (a):

[0009]

[0010] (In the general formula (a), A １ and A ２ are each a fluorine atom or OR １ where A １ When A is a fluorine atom ２ is OR １ and A １ is OR １ When A ２ is a fluorine atom; R １ represents a hydrocarbon group having 1 to 12 carbon atoms; R ２ is an aryl group, a heteroaryl group, a cyano group, -X-(Y １ ｎ -R ４ ) ｍ , or -(C=NR ５ )-Y ２ -R ６ where X is CO, SO, SO ２、 or PO, Y １ and Y ２ are each independently O, S, or NR ７ n represents an integer of 0 or 1; m represents an integer of 1 or 2; R４ , R ５ , R ６ , R ７ each independently represents a hydrocarbon group having 1 to 12 carbon atoms, ４ and R ７ , R ５ and R ６ , or R ６ and R ７ may be bonded to each other to form a ring; R ３ represents a hydrogen atom, or an alkyl group, aryl group, or heteroaryl group having 1 to 12 carbon atoms.

[0011] [2] A fluorine-containing pyridine compound of [1] represented by the following general formula (1):

[0012]

[0013] (In general formula (1), R １ , R ２ , and R ３ is as defined above.)

[0014] [3] A fluorine-containing pyridine compound of [1] represented by the following general formula (2):

[0015]

[0016] (In general formula (2), R １ , R ２ , and R ３ is as defined above.)

[0017] [4] A method for producing a fluorine-containing pyridine compound, comprising a step of reacting a fluoroisobutylene derivative represented by the following general formula (3) with a compound represented by the following general formula (4) or a salt thereof to obtain a fluorine-containing pyridine compound represented by the following general formula (1):

[0018]

[0019] (In the general formulas (1), (3) and (4), R １ represents a hydrocarbon group having 1 to 12 carbon atoms; R ２ is an aryl group, a heteroaryl group, a cyano group, -X-(Y １ ｎ-R ４ ) ｍ , or -(C=NR ５ )-Y ２ -R ６ where X is CO, SO, SO ２、 or PO, Y １ and Y ２ are each independently O, S, or NR ７ n represents an integer of 0 or 1; m represents an integer of 1 or 2; R ４ , R ５ , R ６ , R ７ each independently represents a hydrocarbon group having 1 to 12 carbon atoms, ４ and R ７ , R ５ and R ６ , or R ６ and R ７ may be bonded to each other to form a ring; R ３ represents a hydrogen atom, or an alkyl group, aryl group, or heteroaryl group having 1 to 12 carbon atoms.

[0020] [5] A method for producing a fluorine-containing pyridine compound, comprising a step of reacting a fluoroisobutane derivative represented by the following general formula (5) with a compound represented by the following general formula (4) or a salt thereof to obtain a fluorine-containing pyridine compound represented by the following general formula (1):

[0021]

[0022] (In the general formulas (1), (4) and (5), R １ represents a hydrocarbon group having 1 to 12 carbon atoms; R ２ is an aryl group, a heteroaryl group, a cyano group, -X-(Y １ ｎ -R ４ ) ｍ , or -(C=NR ５ )-Y ２ -R ６ where X is CO, SO, SO ２、 or PO, Y １ and Y ２are each independently O, S, or NR ７ n represents an integer of 0 or 1; m represents an integer of 1 or 2; R ４ , R ５ , R ６ , R ７ each independently represents a hydrocarbon group having 1 to 12 carbon atoms, ４ and R ７ , R ５ and R ６ , or R ６ and R ７ may be bonded to each other to form a ring; R ３ represents a hydrogen atom, or an alkyl group, aryl group, or heteroaryl group having 1 to 12 carbon atoms.

[0023] [6] A method for producing a fluorine-containing pyridine compound, comprising a step of reacting a fluoroisobutylene derivative represented by the following general formula (3) with a compound represented by the following general formula (6) or a salt thereof to obtain a fluorine-containing pyridine compound represented by the following general formula (2):

[0024]

[0025] (In the general formulas (2), (3) and (6), R １ represents a hydrocarbon group having 1 to 12 carbon atoms; R ２ is an aryl group, a heteroaryl group, a cyano group, -X-(Y １ ｎ -R ４ ) ｍ , or -(C=NR ５ )-Y ２ -R ６ where X is CO, SO, SO ２、 or PO, Y １ and Y ２ are each independently O, S, or NR ７ n represents an integer of 0 or 1; m represents an integer of 1 or 2; R ４ , R ５ , R ６ , R ７ each independently represents a hydrocarbon group having 1 to 12 carbon atoms, ４and R ７ , R ５ and R ６ , or R ６ and R ７ may be bonded to each other to form a ring; R ３ represents a hydrogen atom, or an alkyl group, an aryl group, or a heteroaryl group having 1 to 12 carbon atoms; Z represents a cyano group or -V-(O ｌ -R ８ ) ｋ where V represents SO, SO ２ or PO, l represents an integer of 0 or 1, k represents an integer of 1 or 2, R ８ represents a hydrocarbon group having 1 to 12 carbon atoms, an aryl group, or a heteroaryl group.

[0026] [7] A method for producing a fluorine-containing pyridine compound, comprising a step of reacting a fluoroisobutane derivative represented by the following general formula (5) with a compound represented by the following general formula (6) or a salt thereof to obtain a fluorine-containing pyridine compound represented by the following general formula (2):

[0027]

[0028] (In the general formulas (2), (5) and (6), R １ represents a hydrocarbon group having 1 to 12 carbon atoms; R ２ is an aryl group, a heteroaryl group, a cyano group, -X-(Y １ ｎ -R ４ ) ｍ , or -(C=NR ５ )-Y ２ -R ６ where X is CO, SO, SO ２、 or PO, Y １ and Y ２ are each independently O, S, or NR ７ n represents an integer of 0 or 1; m represents an integer of 1 or 2; R ４ , R ５ , R ６ , R ７ each independently represents a hydrocarbon group having 1 to 12 carbon atoms,４ and R ７ , R ５ and R ６ , or R ６ and R ７ may be bonded to each other to form a ring; R ３ represents a hydrogen atom, or an alkyl group, an aryl group, or a heteroaryl group having 1 to 12 carbon atoms; Z represents a cyano group or -V-(O ｌ -R ８ ) ｋ where V represents SO, SO ２ or PO, l represents an integer of 0 or 1, k represents an integer of 1 or 2, R ８ represents a hydrocarbon group having 1 to 12 carbon atoms, an aryl group, or a heteroaryl group.

[0029] According to the present invention, a novel fluorine-containing pyridine compound and a method for producing the same can be provided.

[0030] [Fluorine-Containing Pyridine Compound] The fluorine-containing pyridine compound of the present invention is represented by the following general formula (a).

[0031]

[0032] (In the general formula (a), A １ and A ２ are each a fluorine atom or OR １ where A １ When A is a fluorine atom ２ is OR １ and A １ is OR １ When A ２ is a fluorine atom; R １ represents a hydrocarbon group having 1 to 12 carbon atoms; R ２ is an aryl group, a heteroaryl group, a cyano group, -X-(Y １ ｎ -R ４ ) ｍ , or -(C=NR ５ )-Y ２ -R ６ where X is CO, SO, SO ２、 or PO, Y １and Y ２ are each independently O, S, or NR ７ n represents an integer of 0 or 1; m represents an integer of 1 or 2; R ４ , R ５ , R ６ , R ７ each independently represents a hydrocarbon group having 1 to 12 carbon atoms, ４ and R ７ , R ５ and R ６ , or R ６ and R ７ may be bonded to each other to form a ring; R ３ represents a hydrogen atom, or an alkyl group, aryl group, or heteroaryl group having 1 to 12 carbon atoms.

[0033] That is, the fluorine-containing pyridine compound of the present invention is represented by the following general formula (1) or (2).

[0034] (In general formulas (1) and (2), R １ , R ２ , and R ３ is as defined above.)

[0035] The fluorine-containing pyridine compound of the present invention has a trifluoromethyl group at the 3-position of the pyridine ring and fluorine atoms or OR １ The compound has a fluorine-containing group at the 5-position, an electron-withdrawing group at the 6-position, and a hydrocarbon group at the 6-position. This novel compound is not only useful in the fields of medicine and agrochemicals, but also has promise in the field of organic electronic materials. Furthermore, since it has many substituents and has high structural expandability, it can also be used as an intermediate for obtaining a variety of useful compounds. Therefore, the fluorine-containing pyridine compound of the present invention will make a great contribution to industry.

[0036] R １ , R ４ , R ５ , R ６ , R ７The hydrocarbon groups having 1 to 12 carbon atoms each independently represent are not particularly limited as long as they are hydrocarbon groups consisting of carbon atoms and hydrogen atoms having 1 to 12 carbon atoms, and examples thereof include chain hydrocarbon groups, aromatic hydrocarbon groups, and alicyclic hydrocarbon groups. The chain hydrocarbon groups are not particularly limited as long as they have a total of 1 to 12 carbon atoms, and may be linear or branched. The aromatic hydrocarbon groups are not particularly limited as long as they have a total of 6 to 12 carbon atoms, and may be substituted or unsubstituted aromatic hydrocarbon groups. In this case, the substituent may be a hydrocarbon substituent such that the total carbon number of the aromatic hydrocarbon group falls within the range of 6 to 12. The aromatic hydrocarbon group may also have a fused polycyclic structure. The alicyclic hydrocarbon groups are not particularly limited as long as they have a total of 3 to 12 carbon atoms, and may be substituted or unsubstituted alicyclic hydrocarbon groups. In this case, the substituent may be a hydrocarbon substituent such that the total carbon number of the alicyclic hydrocarbon group falls within the range of 3 to 12. The alicyclic hydrocarbon group may have a bridged ring structure. The hydrocarbon group having 1 to 12 carbon atoms may be an aralkyl group such as a benzyl group.

[0037] R １ , R ４ , R ５ , R ６ , R ７ Examples of the chain hydrocarbon group each independently represent include alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl; alkenyl groups such as ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, and dodecenyl; and alkynyl groups such as ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, decynyl, undecynyl, and dodecynyl.

[0038] R １ , R ４, R ５ , R ６ , R ７ Examples of the aromatic hydrocarbon group independently represented by are a phenyl group, a benzyl group, a tolyl group, a naphthyl group, etc. The tolyl group may be any of an o-tolyl group, an m-tolyl group, and a p-tolyl group.

[0039] R １ , R ４ , R ５ , R ６ , R ７ The alicyclic hydrocarbon groups independently represented by each of the groups include saturated or unsaturated cyclic hydrocarbon groups. Examples of the cyclic hydrocarbon groups include a cyclopropyl group, a cyclobutyl group, a cyclohexyl group, a cyclopentyl group, an adamantyl group, and a norbornyl group.

[0040] R １ is preferably a chain hydrocarbon group or an aromatic hydrocarbon group, more preferably a chain hydrocarbon group, still more preferably a chain hydrocarbon group having 1 to 6 carbon atoms, still more preferably a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, or hexyl group, particularly preferably a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, or t-butyl group, and most preferably a methyl group or an ethyl group.

[0041] R ４ , R ５ , R ６ , R ７ are each independently preferably 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, still more preferably a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, or benzyl group, particularly preferably a methyl group, ethyl group, n-propyl group, isopropyl group, isobutyl group, s-butyl group, t-butyl group, or benzyl group, and most preferably a methyl group, ethyl group, isopropyl group, or benzyl group.

[0042] R２ 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 where X represents CO, SO, SO ２、 or PO, and Y １ and Y ２ are each independently O, S, or NR ７ where n is an integer of 0 or 1, and m is an integer of 1 or 2. ２ is preferably a group having sufficient electron-withdrawing properties.

[0043] R ２ Examples of the aryl group that can be represented include a phenyl group, a tolyl group, an o-xylyl group, an m-xylyl group, a p-xylyl group, a naphthyl group, etc. The aryl group preferably has 6 to 12 carbon atoms.

[0044] R ２ Examples of heteroaryl groups that may be represented include 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl, indolyl, etc. The heteroaryl group preferably has a total of 5 to 12 carbon atoms and heteroatoms.

[0045] R ２ is -X-(Y １ ｎ -R ４ ) ｍ When R ２ is an ester of a carboxylic acid, sulfonic acid, sulfinic acid, or phosphonic acid, 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. ２ is preferably an ester of a carboxylic acid, sulfonic acid, sulfinic acid, or phosphonic acid, more preferably an ester of a carboxylic acid.

[0046] R ２-(C=NR ５ )-Y ２ -R ６ When R ２ is an ester of an imidic acid, a thioester of an imidic acid, or an amide (amidine) of an imidic acid. ２ is preferably an ester of an imide acid.

[0047] R ２ In this case, R ４ and R ７ , R ５ and R ６ , or R ６ and R ７ may be bonded to each other to form a ring. ４ and R ７ , R ５ and R ６ , or R ６ and R ７ The number of carbon atoms in the divalent hydrocarbon group formed by bonding R to each other is in the range of 2 to 24. ４ and R ７ , R ５ and R ６ , or R ６ and R ７ The divalent hydrocarbon group formed by bonding together may be a linear hydrocarbon group or a branched hydrocarbon group. ４ and R ７ , R ５ and R ６ , or R ６ and R ７ The divalent hydrocarbon group formed by bonding together may have an aromatic ring or an alicyclic structure. ４ and R ７ , R ５ and R ６ , or R ６ and R ７ The number of carbon atoms in the divalent hydrocarbon group formed by bonding together 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.

[0048] R ３represents a hydrogen atom, or an alkyl group having 1 to 12 carbon atoms, an aryl group, or a heteroaryl group.

[0049] R ３ Examples of the alkyl group having 1 to 12 carbon atoms that can be represented by include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, etc. Among these, an alkyl group having 1 to 8 carbon atoms is preferred, an alkyl group having 1 to 6 carbon atoms is more preferred, an alkyl group having 1 to 4 carbon atoms is even more preferred, and a methyl group or an ethyl group is particularly preferred.

[0050] R ３ Examples of the aryl group that can be represented include a phenyl group, a tolyl group, an o-xylyl group, an m-xylyl group, a p-xylyl group, a naphthyl group, etc. The aryl group preferably has 6 to 12 carbon atoms.

[0051] R ３ Examples of heteroaryl groups that may be represented include 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl, indolyl, etc. The heteroaryl group preferably has a total of 5 to 12 carbon atoms and heteroatoms.

[0052] In one embodiment, the fluorine-containing pyridine compound is A １ is a fluorine atom, and A ２ is OR １ and R １ is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, or a hexyl group, and R ２ is -X-(Y １ ｎ -R ４ ) ｍ and R ３may be a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a phenyl group, a tolyl group, an o-xylyl group, an m-xylyl group, a p-xylyl group, a naphthyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 2-thienyl group, a 3-thienyl group, a 2-furanyl group, a 3-furanyl group, or an indolyl group.

[0053] In one embodiment, the fluorine-containing pyridine compound is A １ is OR １ and A ２ is a fluorine atom, and R １ is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, or a hexyl group, and R ２ is a phenyl group, a tolyl group, an o-xylyl group, a m-xylyl group, a p-xylyl group, a naphthyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 2-thienyl group, a 3-thienyl group, a 2-furanyl group, a 3-furanyl group, or an indolyl group, and R ３ may be a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a phenyl group, a tolyl group, an o-xylyl group, an m-xylyl group, a p-xylyl group, a naphthyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 2-thienyl group, a 3-thienyl group, a 2-furanyl group, a 3-furanyl group, or an indolyl group.

[0054] (Uses) The compound of the present invention is useful in the fields of pharmaceuticals, agrochemicals, and organic electronic materials, and can also be used as an intermediate for obtaining other useful compounds. The compound of the present invention may be used in the form of a salt. In this case, examples of the salt include hydrochloride, hydrobromide, acetate, sulfate, etc.

[0055] The use of the compound of the present invention in the field of agricultural chemicals includes, for example, the use as harmful fungi control agent, arthropod control agent and herbicide.For example, the compound of the present invention can be used as harmful fungi control agent to control various cultivated plants such as wheat, rye, barley, oat, rice, corn, grass, banana, cotton, soybean, coffee plant, sugarcane, grape vine, fruit tree and ornamental plant; vegetables such as cucumber, bean, tomato, potato and gourd; and many fungi that are on the seeds of these plants.

[0056] The compounds of the present invention are suitable for controlling, for example, the following plant diseases caused by harmful fungi: rice blast (Primularia oryzae), southern leaf blight (Cochliobolus miyabeanus), sheath blight (Rizoctonia solani), etc.; wheat powdery mildew (Erysiphe graminis), head blight (Gibberella zeae), (red) rust (Puccinia striiformis, P. graminis, P. recondita, P. hordei), snow rot (Typhula sp., Micronectriella nivalis), naked smut (Ustilago tritici, U. nuda), smut (Tilletia caries), eyespot (Pseudocercosporella herpotrichoide), scald (Rhynchosporium secalis), leaf blight (Septoria tritici), leaf spot (Leptosphaeria nodorum), net blotch (Pyrenophora teres), hazel (Helminthosporium zonatum Ikata), etc.; citrus black spot (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum, P. italicum), brown rot (Phytophthora citrophthora, P. nicotianae), black spot (Phyllostictina citricarpa), canker (Xanthomonas citri), etc.; Monilia disease (Monilinia mali), canker (Valsa mali), powdery mildew (Podosphaera leucotricha), leaf spot (Alternaria mali), black spot (Venturia inaequalis), black spot (Mycospherella pomi), anthracnose (Colletotrichum) of apples acutatum), ring spot (Botryosphaeria berengeriana), red rot (Gymnosporangium yamadae), brown rot (Monilinia fructicola), etc.;Pear black spot (Venturia nashicola, V. pirina), black spot (Alternaria kikuchiana), red spot (Gymnosporangium haraeanum), brown spot (Monilinia fructicola), etc.; peach brown spot (Monilinia fructicola), black spot (Cladosporium caepophilum), Phomopsis rot (Phomopsis sp.), etc.; grape black rot (Elinoe ampelina), late rot (Colletotrichum acutatum), powdery mildew (Uncinula necaator), rust (Phakopsora ampelopsidis), black rot (Guignardia bidwellii), downy mildew (Plasmopara viticola), brown rot (Monilinia fructigena), black scab (Cladosporium viticolum), gray mold (Botrytis cinerea), etc.; persimmon anthracnose (Gloeosporium kaki), leaf drop (Cercospora kaki, Mycoshaerella nawae); cucurbit anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea, Oidiopsis taurica), vine blight (Didymella bryoniae), vine wilt (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), late blight (Phytophthora sp.), seedling damping-off (Pythium sp.), etc.; tomato ring spot (Alternaria solani), leaf mold (Cladosporium fulvum), late blight (Phytophthora infestans), foot rot (Fusarium solani), etc.; brown spot of eggplant (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum), etc.; black spot of cruciferous vegetables (Alternaria japonica), white spot (Cercosporella brassicae), soft rot (Erwinia carotovora), etc.;Onion rust (Puccinia allii), etc.; soybean purple spot (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), etc.; kidney bean anthracnose (Colletotrichum lindemthianum), etc.; peanut black spot (Cercospora personata), brown spot (Cercospora arachidicola), etc.; pea powdery mildew (Erysiphe pisi), etc.; potato summer blight (Alternaria solani), late blight (Phytophthora infestans), leaf rot fungus (Rhizoctonia solani), etc.; strawberry powdery mildew (Sphaerrotheca humuli), etc.; tea net blight (Exobasidium reticulatum), white spot (Elsinoe leucospila), etc.; tobacco red spot (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), late blight (Phytophthora nicotianae), wildfire (Pseudomonus syringae), etc.; brown spot of sugar beet (Cercospora beticola), damping-off (Aphanomyces cochliodes), etc.; black spot of rose (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), etc.; brown spot of chrysanthemum (Septoria chrysanthemi-indici), white rust (Puccinia horiana), etc.; gray mold of various crops (Botrytis cinerea), sclerotinia sclerotiorum, etc.;

[0057] When the harmful fungi control agent is actually applied, the fluorine-containing pyridine compound of the present invention or its salt may be used in its pure form without adding any other components, or it may be used in the form that a general pesticide can take, i.e., in the form of a solid formulation such as a granule, dust, broad-area spray or dustable product, or in the form of a liquid formulation such as a wettable powder, emulsifiable concentrate, water-soluble concentrate, solution, paste, oil dispersion, dispersion formulation, emulsion formulation, oil solution, aerosol, spray or flowable formulation. The application form depends on the specific purpose, but in each case, it is preferable that the fluorine-containing pyridine compound of the present invention or its salt is finely and uniformly dispersed.

[0058] The harmful fungi control agent may be prepared, for example, by applying the fluorine-containing pyridine compound of the present invention or a salt thereof to a solvent and / or onto a solid carrier, using an auxiliary agent such as an emulsifier or a dispersant, if necessary.

[0059] [Method for Producing Fluorine-Containing Pyridine Compound] Specific examples of the method for producing the fluorine-containing pyridine compound of the present invention include the following methods (A) to (D).

[0060] (A) A method comprising a step of reacting a fluoroisobutylene derivative represented by the following general formula (3) with a compound represented by the following general formula (4) or a salt thereof to obtain a fluorine-containing pyridine compound represented by the following general formula (1):

[0061]

[0062] (In the general formulas (1), (3) and (4), R １ represents a hydrocarbon group having 1 to 12 carbon atoms; R ２ is an aryl group, a heteroaryl group, a cyano group, -X-(Y １ ｎ -R ４ ) ｍ , or -(C=NR ５ )-Y ２ -R ６ where X is CO, SO, SO ２、 or PO, Y １ and Y ２ are each independently O, S, or NR ７n represents an integer of 0 or 1; m represents an integer of 1 or 2; R ４ , R ５ , R ６ , R ７ each independently represents a hydrocarbon group having 1 to 12 carbon atoms, ４ and R ７ , R ５ and R ６ , or R ６ and R ７ may be bonded to each other to form a ring; R ３ represents a hydrogen atom, or an alkyl group, aryl group, or heteroaryl group having 1 to 12 carbon atoms.

[0063] (B) A method comprising a step of reacting a fluoroisobutane derivative represented by the following general formula (5) with a compound represented by the following general formula (4) or a salt thereof to obtain a fluorine-containing pyridine compound represented by the following general formula (1):

[0064]

[0065] (In general formulas (1), (4) and (5), R １ , R ２ , and R ３ is as defined above.)

[0066] (C) A method comprising a step of reacting a fluoroisobutylene derivative represented by the following general formula (3) with a compound represented by the following general formula (6) or a salt thereof to obtain a fluorine-containing pyridine compound represented by the following general formula (2):

[0067]

[0068] (In general formulas (2), (3) and (6), R １ , R ２ , and R ３ is as defined above. Z is a cyano group or -V-(O ｌ -R ８ ) ｋ where V represents SO, SO ２ or PO, l represents an integer of 0 or 1, k represents an integer of 1 or 2, R８ represents a hydrocarbon group having 1 to 12 carbon atoms, an aryl group, or a heteroaryl group.

[0069] (D) A method comprising a step of reacting a fluoroisobutane derivative represented by the following general formula (5) with a compound represented by the following general formula (6) or a salt thereof to obtain a fluorine-containing pyridine compound represented by the following general formula (2):

[0070]

[0071] (In the general formulas (2), (5) and (6), R １ , R ２ , R ３ and Z is as defined above.

[0072] In general, methods for synthesizing fluorine-containing compounds can be broadly divided into methods starting from raw materials that originally contain fluorine (building block methods) and methods in which fluorine is newly introduced into a compound. The former methods are characterized by the fact that the position at which fluorine is introduced depends on the raw material. The latter methods are less efficient because they can only use raw materials having substituents that are compatible with the reaction conditions for introducing fluorine and often require the prior introduction of a "marker" such as bromine or iodine at the position at which fluorine is introduced. In the production method of the present invention, by employing the above methods (A) to (D), it is possible to obtain a novel fluorine-containing pyridine compound (the fluorine-containing pyridine compound of the present invention) in which fluorine is introduced at a position that has been difficult to introduce using conventional methods. Furthermore, the production method of the present invention is a building block method, and can efficiently obtain a fluorine-containing pyridine compound without using expensive halogen elements, etc.

[0073] In the above methods (A) and (B), HF is released by the reaction, and in the above methods (C) and (D), HF and HZ are released by the reaction.

[0074] In the above methods (C) and (D), Z is a cyano group or -V-(O ｌ -R ８ ) ｋ Z represents -V-(O ｌ -R ８ ) ｋWhen V represents SO ２ (sulfonyl group), l is 0, and k is 1.

[0075] Z is -V-(O ｌ -R ８ ) ｋ R when representing ８ represents a hydrocarbon group having 1 to 12 carbon atoms, an aryl group, or a heteroaryl group. ８ is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a phenyl group, a tolyl group, an o-xylyl group, an m-xylyl group, a p-xylyl group, a naphthyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 2-thienyl group, a 3-thienyl group, a 2-furanyl group, a 3-furanyl group, or an indolyl group.

[0076] In the above methods (A) to (D), the compound represented by the general formula (4) or (6) may be in the form of a salt. When it is in the form of a salt, the amino group (—NH ２ ) is cationized (-NH ３ ＋ ) and forms a salt with the counter ion. The counter ion is not particularly limited as long as it is a monovalent anion, and examples thereof include F － , Cl － ,Br － , I － From the viewpoint of availability, the salt is preferably a hydrochloride salt.

[0077] The compounds represented by the above general formulas (3) to (6) may be commercially available compounds or compounds produced by known methods.

[0078] In the above methods (A) to (D), the reaction may be carried out in the presence of an organic solvent. Examples of the organic solvent that can be used include ethers such as tetrahydrofuran, diethyl ether, dioxane, monoglyme, diglyme, triglyme, and tetraglyme; 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, methylpyrrolidone, dimethylethyleneurea, tetramethylurea, dimethyl sulfoxide, and sulfolane.

[0079] In the above methods (A) to (D), the reaction may be carried out in the presence of a basic substance. Examples of the basic substance 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, 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.

[0080] In the above methods (A) to (D), the reaction may be carried out in two steps using two types of basic substances. For example, a two-step reaction may be employed in which an intermediate is produced in the first step using a relatively mild base, and then a final product is obtained in the second step using a stronger base than that used in the first step (e.g., a phosphazene base).

[0081] The reaction temperature in the above methods (A) to (D) 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 the above methods (A) to (D) is preferably 0.5 to 48 hours, more preferably 1 to 36 hours, and even more preferably 10 to 25 hours.

[0082] Although some embodiments of the present invention have been described above, the present invention is not limited to the above-described embodiments, but includes all aspects encompassed by the concept of the present invention and the scope of the claims, and can be modified in various ways within the scope of the present invention.

[0083] The present invention will be explained in more detail below with reference to examples, but the present invention is not limited to these examples in any way.

[0084] Example 1 Production of methyl 6-fluoro-4-methoxy-2-methyl-5-trifluoromethyl-3-pyridinecarboxylate 1.1 g (9.6 mmol) of methyl 3-amino-2-butenoate, 3.7 g (29 mmol) of 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 heated under reflux. After approximately 16 hours, the contents were purified using a silica gel column to obtain 0.8 g of the following compound. The yield was 31%.

[0085]

[0086] The analytical results were as follows: Mass spectrum (APCI, m / z): 267 ([M] ＋ ) １ H-NMR (400MHz, CDCl ３ ) δppm: 3.99 (s, 3H), 3.97 (s, 3H), 2.51 (s, 3H)

[0087] Example 2 Production 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 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 heated under reflux. After about 12 hours, the contents were purified using a silica gel column to obtain 0.7 g of the following compound. The yield was 25%.

[0088]

[0089] The analytical results were as follows: Mass spectrum (APCI, m / z): 281 ([M] ＋ ) １ H-NMR (400MHz, CDCl ３ ) δppm: 4.45 (q, 2H), 3.98 (s, 3H), 2.51 (s, 3H), 1.42 (t, 3H)

[0090] Example 3 [Production of 1-methylethyl 6-fluoro-4-methoxy-2-methyl-5-trifluoromethyl-3-pyridinecarboxylate] 1.1 g (7.7 mmol) of 1-methylethyl 3-amino-2-butenoate, 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 heated under reflux. After about 24 hours, the contents were purified using a silica gel column to obtain 0.4 g of the following compound. The yield was 19%.

[0091]

[0092] The analytical results were as follows: Mass spectrum (APCI, m / z): 295 ([M] ＋ ) １ H-NMR (400MHz, CDCl ３ ) δppm: 5.33 (sep, 1H), 3.99 (s, 3H), 2.51 (s, 3H), 1.41 (d, 6H)

[0093] Example 4 Production of phenylmethyl 6-fluoro-4-methoxy-2-methyl-5-trifluoromethyl-3-pyridinecarboxylate 1.5 g (7.8 mmol) of phenylmethyl 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 heated to reflux. After about 9 hours, the contents were purified using a silica gel column to obtain 0.3 g of the following compound. The yield was 12%.

[0094]

[0095] The analytical results were as follows: Mass spectrum (APCI, m / z): 343 ([M] ＋ )

[0096] Example 5 Production 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 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 heated under reflux. After about 10 hours, the contents were purified using a silica gel column to obtain 1.4 g of the following compound. The yield was 39%.

[0097]

[0098] The analytical results were as follows: Mass spectrum (APCI, m / z): 295 ([M] ＋ ) １ H-NMR (400MHz, CDCl ３ ) δppm: 4.43 (q, 2H), 3.96 (s, 3H), 2.73 (q, 2H), 1.40 (t, 3H), 1.27 (t, 3H)

[0099] Example 6 Production 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-propenoate, 2.0 g (16 mmol) of 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 about 12 hours, the contents were purified using a silica gel column to obtain 0.2 g of the following compound. The yield was 9%.

[0100]

[0101] The analytical results were as follows: Mass spectrum (APCI, m / z): 344 ([M] ＋ )

[0102] Example 7 [Production of 4-fluoro-2-methoxy-5-phenyl-3-(trifluoromethyl)pyridine] First Step: Under ice-water cooling, 1.0 g (3.4 mmol) of 2-phenyl-2-(phenylsulfonyl)ethanamine 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. Subsequently, 0.9 g (6.7 mmol) of diisopropylethylamine was added dropwise so that the internal temperature did not exceed 10°C, and the mixture was heated to room temperature. After approximately 16 hours, the contents were purified with a silica gel column to obtain 1.0 g of methyl 3,3,3-trifluoro-N-(2-phenyl-2-(phenylsulfonyl)ethyl)-2-(trifluoromethyl)propanimidate shown below as an intermediate. The isolated yield was 67%.

[0103]

[0104] The analytical results were as follows: Mass spectrum (APCI, m / z): 453 ([M] ＋ )

[0105] Second Step: Under ice-water cooling, 1.0 g (2.3 mmol) of methyl 3,3,3-trifluoro-N-(2-phenyl-2-(phenylsulfonyl)ethyl)-2-(trifluoromethyl)propanimidate and 2.3 g (6.8 mmol) of sodium tetraphenylborate were added to 60 g of tetrahydrofuran. Subsequently, 8.5 ml (6.8 mmol) of a hexane solution (0.8 M) of phosphazene base P4-t-Bu was added dropwise so that the internal temperature did not exceed 10°C, and the mixture was heated to room temperature. After approximately 16 hours, the contents were purified using a silica gel column to obtain 12 mg of the following compound. The isolated yield was 2%.

[0106]

[0107] The analytical results were as follows: Mass spectrum (APCI, m / z): 271 ([M] ＋ )

[0108] Example 8 [Production of 4-fluoro-5-(2-furanyl)-2-methoxy-3-(trifluoromethyl)pyridine] First Step: Under ice-water cooling, 1.1 g (3.7 mmol) of 2-(2-furanyl)-2-(2-thienylsulfonyl)ethanamine 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. Subsequently, 1.1 g (11 mmol) of triethylamine was added dropwise so that the internal temperature did not exceed 10°C, and the mixture was heated to room temperature. After approximately 16 hours, the contents were purified with a silica gel column to obtain 1.2 g of methyl 3,3,3-trifluoro-N-(2-(2-furanyl)-2-(2-thienylsulfonyl)ethyl)-2-(trifluoromethyl)propanimidate as an intermediate. The isolated yield was 75%.

[0109]

[0110] The analytical results were as follows: Mass spectrum (APCI, m / z): 449 ([M] ＋ )

[0111] Second Step: 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)propanimidate and 2.4 g (8.3 mmol) of lithium bistrifluoromethanesulfonylimide were added to 60 g of tetrahydrofuran. Subsequently, 10 ml (8.3 mmol) of a hexane solution (0.8 M) of phosphazene base P4-t-Bu was added dropwise so that the internal temperature did not exceed 10°C, and the mixture was heated to room temperature. After approximately 16 hours, the contents were purified using a silica gel column to obtain 4 mg of the following compound. The isolated yield was 0.5%.

[0112]

[0113] The analytical results were as follows: Mass spectrum (APCI, m / z): 261 ([M] ＋ )

[0114] Example 9 [Preparation of 4-fluoro-2-methoxy-5-thienyl-3-(trifluoromethyl)pyridine] First Step: Under ice-water cooling, 1.0 g (3.2 mmol) of 2-(2-thienyl)-2-(2-thienylsulfonyl)ethanamine 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. Subsequently, 5.0 g (6.5 mmol) of diisopropylethylamine was added dropwise so that the internal temperature did not exceed 10°C, and the mixture was heated to room temperature. After approximately 16 hours, the contents were purified with a silica gel column to obtain 1.2 g of methyl 3,3,3-trifluoro-N-(2-(2-thienyl)-2-(2-thienylsulfonyl)ethyl)-2-(trifluoromethyl)propanimidate represented by the following formula as an intermediate. The isolated yield was 81%.

[0115]

[0116] The analytical results were as follows: Mass spectrum (APCI, m / z): 465 ([M] ＋ )

[0117] Second Step: 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)propanimidate and 2.2 g (7.8 mmol) of lithium bistrifluoromethanesulfonylimide were added to 60 g of tetrahydrofuran. Subsequently, 9.8 ml (7.8 mmol) of a hexane solution (0.8 M) of phosphazene base P4-t-Bu was added dropwise so that the internal temperature did not exceed 10°C, and the temperature was raised to room temperature. After approximately 16 hours, the contents were purified with a silica gel column to obtain 7 mg of the following compound. The isolation yield was 1%.

[0118]

[0119] The analytical results were as follows: Mass spectrum (APCI, m / z): 277 ([M] ＋ )

[0120] Example 10 Production of 6-fluoro-4-methoxy-2-methyl-5-trifluoromethyl-3-pyridinecarboxylic acid, (2E)-3-phenyl-2-propen-1-yl ester 0.5 g (2.3 mmol) of cinnamyl 3-aminocrotonate was dissolved in 23 mL of heptane, 0.6 g (4.8 mmol) of diisopropylethylamine was added, and the mixture was cooled to 0°C. Then, 0.5 g (2.4 mmol) of methyl 2-(trifluoromethyl)-3,3,3-trifluoropropionate was added, and the mixture was stirred under heated reflux for 24.2 hours. After that, silica gel column purification was carried out to obtain the following compound.

[0121]

[0122] The analytical results were as follows: Mass spectrum (APCI, m / z): 369.1 ([M] ＋ )

[0123] Example 11 Production of methyl 2-ethyl-6-fluoro-4-methoxy-5-trifluoromethyl-3-pyridinecarboxylate 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 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, and the mixture was stirred under heated reflux for 16.7 hours. After that, silica gel column purification was carried out to obtain the following compound.

[0124]

[0125] The analytical results were as follows: Mass spectrum (APCI, m / z): 281.4 ([M] ＋ )

[0126] Example 12 Production of propyl 6-fluoro-4-methoxy-2-methyl-5-trifluoromethyl-3-pyridinecarboxylate 0.5 g (3.6 mmol) of propyl 3-aminobut-2-enoate was dissolved in 35 mL of heptane, 1.4 g (10.5 mmol) of 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, and the mixture was stirred under heated reflux for 21.2 hours. After that, silica gel column purification was carried out to obtain the following compound.

[0127]

[0128] The analytical results were as follows: Mass spectrum (APCI, m / z): 295.4 ([M] ＋ )

[0129] From the above, it is clear that the novel fluorine-containing pyridine compound of the present invention can be produced.

[0130] The fluorine-containing pyridine compound of the present invention is suitable for use in the fields of pharmaceuticals, agricultural chemicals, and organic electronic materials. In addition, since it has many substituents and has high structural expandability, it can also be used as an intermediate for various useful compounds.

Claims

1. A fluorine-containing pyridine compound represented by the following general formula (a): (In the general formula (a), A １ and A ２ are each a fluorine atom or OR １ where A １ When A is a fluorine atom ２ is OR １ and A １ is OR １ When A ２ is a fluorine atom; R １ represents a hydrocarbon group having 1 to 12 carbon atoms; R ２ is an aryl group, a heteroaryl group, a cyano group, -X-(Y １ ｎ -R ４ ) ｍ , or -(C=NR ５ )-Y ２ -R ６ where X is CO, SO, SO ２、 or PO, Y １ and Y ２ are each independently O, S, or NR ７ n represents an integer of 0 or 1; m represents an integer of 1 or 2; R ４ , R ５ , R ６ , R ７ each independently represents a hydrocarbon group having 1 to 12 carbon atoms, ４ and R ７ , R ５ and R ６ , or R ６ and R ７ may be bonded to each other to form a ring; R ３ represents a hydrogen atom, or an alkyl group, aryl group, or heteroaryl group having 1 to 12 carbon atoms.

2. The fluorine-containing pyridine compound according to claim 1, which is represented by the following general formula (1): (In general formula (1), R １ , R ２ , and R ３ is as defined in claim 1.

3. The fluorine-containing pyridine compound according to claim 1, which is represented by the following general formula (2): (In general formula (2), R １ , R ２ , and R ３ is as defined in claim 1.

4. A method for producing a fluorine-containing pyridine compound, comprising a step of reacting a fluoroisobutylene derivative represented by the following general formula (3) with a compound represented by the following general formula (4) or a salt thereof to obtain a fluorine-containing pyridine compound represented by the following general formula (1): (In the general formulas (1), (3) and (4), R １ represents a hydrocarbon group having 1 to 12 carbon atoms; R ２ is an aryl group, a heteroaryl group, a cyano group, -X-(Y １ ｎ -R ４ ) ｍ , or -(C=NR ５ )-Y ２ -R ６ where X is CO, SO, SO ２、 or PO, Y １ and Y ２ are each independently O, S, or NR ７ n represents an integer of 0 or 1; m represents an integer of 1 or 2; R ４ , R ５ , R ６ , R ７ each independently represents a hydrocarbon group having 1 to 12 carbon atoms, ４ and R ７ , R ５ and R ６ , or R ６ and R ７ may be bonded to each other to form a ring; R ３ represents a hydrogen atom, or an alkyl group, aryl group, or heteroaryl group having 1 to 12 carbon atoms.

5. A method for producing a fluorine-containing pyridine compound, comprising a step of reacting a fluoroisobutane derivative represented by the following general formula (5) with a compound represented by the following general formula (4) or a salt thereof to obtain a fluorine-containing pyridine compound represented by the following general formula (1): (In the general formulas (1), (4) and (5), R １ represents a hydrocarbon group having 1 to 12 carbon atoms; R ２ is an aryl group, a heteroaryl group, a cyano group, -X-(Y １ ｎ -R ４ ) ｍ , or -(C=NR ５ )-Y ２ -R ６ where X is CO, SO, SO ２、 or PO, Y １ and Y ２ are each independently O, S, or NR ７ n represents an integer of 0 or 1; m represents an integer of 1 or 2; R ４ , R ５ , R ６ , R ７ each independently represents a hydrocarbon group having 1 to 12 carbon atoms, ４ and R ７ , R ５ and R ６ , or R ６ and R ７ may be bonded to each other to form a ring; R ３ represents a hydrogen atom, or an alkyl group, aryl group, or heteroaryl group having 1 to 12 carbon atoms.

6. A method for producing a fluorine-containing pyridine compound, comprising a step of reacting a fluoroisobutylene derivative represented by the following general formula (3) with a compound represented by the following general formula (6) or a salt thereof to obtain a fluorine-containing pyridine compound represented by the following general formula (2): (In the general formulas (2), (3) and (6), R １ represents a hydrocarbon group having 1 to 12 carbon atoms; R ２ is an aryl group, a heteroaryl group, a cyano group, -X-(Y １ ｎ -R ４ ) ｍ , or -(C=NR ５ )-Y ２ -R ６ where X is CO, SO, SO ２、 or PO, Y １ and Y ２ are each independently O, S, or NR ７ n represents an integer of 0 or 1; m represents an integer of 1 or 2; R ４ , R ５ , R ６ , R ７ each independently represents a hydrocarbon group having 1 to 12 carbon atoms, ４ and R ７ , R ５ and R ６ , or R ６ and R ７ may be bonded to each other to form a ring; R ３ represents a hydrogen atom, or an alkyl group, an aryl group, or a heteroaryl group having 1 to 12 carbon atoms; Z represents a cyano group or -V-(O ｌ -R ８ ) ｋ where V represents SO, SO ２ or PO, l represents an integer of 0 or 1, k represents an integer of 1 or 2, R ８ represents a hydrocarbon group having 1 to 12 carbon atoms, an aryl group, or a heteroaryl group.

7. A method for producing a fluorine-containing pyridine compound, comprising a step of reacting a fluoroisobutane derivative represented by the following general formula (5) with a compound represented by the following general formula (6) or a salt thereof to obtain a fluorine-containing pyridine compound represented by the following general formula (2): (In the general formulas (2), (5) and (6), R １ represents a hydrocarbon group having 1 to 12 carbon atoms; R ２ is an aryl group, a heteroaryl group, a cyano group, -X-(Y １ ｎ -R ４ ) ｍ , or -(C=NR ５ )-Y ２ -R ６ where X is CO, SO, SO ２、 or PO, Y １ and Y ２ are each independently O, S, or NR ７ n represents an integer of 0 or 1; m represents an integer of 1 or 2; R ４ , R ５ , R ６ , R ７ each independently represents a hydrocarbon group having 1 to 12 carbon atoms, ４ and R ７ , R ５ and R ６ , or R ６ and R ７ may be bonded to each other to form a ring; R ３ represents a hydrogen atom, or an alkyl group, an aryl group, or a heteroaryl group having 1 to 12 carbon atoms; Z represents a cyano group or -V-(O ｌ -R ８ ) ｋ where V represents SO, SO ２ or PO, l represents an integer of 0 or 1, k represents an integer of 1 or 2, R ８ represents a hydrocarbon group having 1 to 12 carbon atoms, an aryl group, or a heteroaryl group.

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