WO2013002205A1 - Nitrogen-containing heterocyclic compound and bactericide for agricultural or horticultural use - Google Patents

Nitrogen-containing heterocyclic compound and bactericide for agricultural or horticultural use Download PDF

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WO2013002205A1
WO2013002205A1 PCT/JP2012/066240 JP2012066240W WO2013002205A1 WO 2013002205 A1 WO2013002205 A1 WO 2013002205A1 JP 2012066240 W JP2012066240 W JP 2012066240W WO 2013002205 A1 WO2013002205 A1 WO 2013002205A1
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group
substituted
unsubstituted
formula
represented
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PCT/JP2012/066240
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French (fr)
Japanese (ja)
Inventor
準 稲垣
耕太郎 柴山
元亮 佐藤
頼人 ▲桑▼原
横山　雅裕
康介 椎木
勇人 齊木
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日本曹達株式会社
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Priority to JP2013522864A priority Critical patent/JP5753583B2/en
Publication of WO2013002205A1 publication Critical patent/WO2013002205A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to an agricultural and horticultural fungicide that can be used safely and safely, and to a nitrogen-containing heterocyclic compound useful as an active ingredient of an agricultural and horticultural fungicide.
  • control agents are used against diseases of agricultural and horticultural crops.
  • many of the conventional control chemicals have insufficient control efficacy, their use is limited by the emergence of drug-resistant pathogens, cause phytotoxicity and pollution to plants, or are toxic to human and livestock fish. And the impact on the environment was not enough. For this reason, there is a strong demand for the appearance of drugs with few such defects.
  • Patent Document 1 or 2 discloses a quinoline derivative having a chemical structure similar to that of the compound of the present invention, and an agricultural and horticultural fungicide containing it as an active ingredient.
  • An object of the present invention is to provide an agricultural and horticultural fungicide that can be used safely and reliably, and a nitrogen-containing heterocyclic compound or a salt thereof useful as an active ingredient of the agricultural and horticultural fungicide.
  • the present inventors diligently studied to solve the above problems. As a result, a nitrogen-containing heterocyclic compound represented by the formula (I) and a salt thereof were obtained. The present inventors have found that this nitrogen-containing heterocyclic compound has a certain effect and can be used safely as an active ingredient of agricultural and horticultural fungicides. The present invention has been completed by further studies based on these findings.
  • a nitrogen-containing heterocyclic compound represented by the formula (I) or a salt thereof is included in the present invention.
  • R represents a group represented by OR 1 , a group represented by NR 1 R 2 , a group represented by SR 1 , a group represented by S ( ⁇ O) R 3 , SO 2 A group represented by R 3 , a group represented by S ( ⁇ O) ( ⁇ NR 4 ) R 5 , a group represented by N ⁇ S ( ⁇ O) R 4 R 5 , or a nitro group.
  • R 1 is a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, A substituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted group; An unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted carboxyl group, an unsubstituted or substituted carbamoyl group, a substituted sulfonyl group, or An amino group having a substituent or a substituent is shown.
  • R 2 represents a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, A substituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted group; Having a heterocyclic group, an unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted carboxyl group, an unsubstituted or substituted carbamoyl group, a substituted sulfonyl group, unsubstituted Or a hydroxyl group having a substituent, or an amino group having no substituent or a substituent.
  • R 3 is an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, unsubstituted or A substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted heterocycle A group, an unsubstituted or substituted mercapto group, an unsubstituted or substituted hydroxyl group, or an unsubstituted or substituted amino group.
  • R 4 and R 5 are each independently an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 An alkynyl group, an unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, or unsubstituted Or a heterocyclic group having a substituent.
  • R 1 and R 2 are taken together to form an unsubstituted or substituted 3- to 8-membered ring, ⁇ CR a R b , or ⁇ N—R c . It may be formed.
  • R a and R b each independently have a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted group A C2-8 alkynyl group, an unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, Unsubstituted or substituted heterocyclic group, unsubstituted or substituted C1-8 acyl group, unsubstituted or substituted carboxyl group, unsubstituted or substituted carbamoyl group, substituted group A sulfonyl group having, an unsubstituted or substituted mercapto group, an unsubstituted or substituted hydroxyl group, or unsubstituted Or an amino group having
  • R c represents an unsubstituted or substituted hydroxyl group, or an unsubstituted or substituted C1-8 alkyl group.
  • R 4 R 5 , R 4 and R 5 may be combined to form an unsubstituted or substituted 5- to 8-membered ring.
  • X 1 is each independently an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, Unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C4-8 cycloalkenyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted An unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted (1-imino) C1-8 alkyl group, an unsubstituted or substituted carboxyl group, Unsubstituted or substituted carbamoyl group, unsubstituted or substituted hydroxyl group, unsubstituted or substituted amino group Mercapto group with an unsubstituted or substituted group, a sulfonyl
  • m represents the number of X 1 and is an integer from 0 to 5.
  • B represents a carbon atom or a nitrogen atom.
  • D represents a 5- to 7-membered heterocycle substituted with been 5-7 membered hydrocarbon ring or an unsubstituted or X 1, substituted by unsubstituted or X 1.
  • X 2 each independently represents an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, Unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C4-8 cycloalkenyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted An unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted (1-imino) C1-8 alkyl group, an unsubstituted or substituted carboxyl group, Unsubstituted or substituted carbamoyl group, unsubstituted or substituted hydroxyl group, unsubstituted or substituted amino group Mercapto group with an unsubstituted or substituted group, a sulfonyl
  • n represents the number of X 2 and is an integer from 0 to 3. Any one of X 2 and R may be combined with each other to form an unsubstituted or substituted 5- to 8-membered ring.
  • E shows unsubstituted or 5- to 7-membered hydrocarbon ring substituted with X 2, or unsubstituted or a 5-7 membered heterocyclic ring substituted with X 2.
  • X represents an oxygen atom (O), a nitrogen atom (NH), or a nitrogen atom (NR ′′) substituted with a C1-8 alkyl group (R ′′).
  • R, X 1 , m, X 2 , n, D, B, and X have the same meaning as in formula (I) described in [1] above.
  • a 1 , A 2 , A 3 , and A 4 each independently represent a carbon atom or a nitrogen atom.
  • R, X 1 , m, X 2 , n, A 1 , A 2 , A 3 , A 4 , B, and X are in the formula (II) described in [2] above. It has the same meaning as each of.
  • R, X 1 , m, X 2 , n, D, B, and X have the same meaning as in formula (I) described in [1] above.
  • a 5 , A 6 , and A 7 each independently represent a carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom. However, oxygen atoms, sulfur atoms, or a combination of oxygen atoms and sulfur atoms are not adjacent to each other.
  • An agricultural and horticultural fungicide containing as an active ingredient at least one selected from the nitrogen-containing heterocyclic compound or a salt thereof according to any one of [1] to [6] above.
  • the nitrogen-containing heterocyclic compound of the present invention is a novel compound useful as an active ingredient for agricultural and horticultural fungicides.
  • the agricultural and horticultural fungicide of the present invention is a safe drug that has a reliable and excellent control effect, does not cause phytotoxicity to plants, and has little toxicity to human and livestock and environmental impact.
  • Nitrogen-containing heterocyclic compound [compound represented by formula (I)]
  • the nitrogen-containing heterocyclic compound according to the present invention is a compound represented by the formula (I) (hereinafter sometimes referred to as “compound (I)”).
  • the nitrogen-containing heterocyclic compound according to the present invention includes hydrates, various solvates and crystal polymorphs. Furthermore, the nitrogen-containing heterocyclic compound according to the present invention includes stereoisomers based on asymmetric carbon atoms, double bonds, and the like, and mixtures thereof.
  • unsubstituted means only the group that is the mother nucleus.
  • the term “having a substituent” means that any hydrogen atom of a group serving as a mother nucleus is substituted with a group having the same or different structure as the mother nucleus. Accordingly, the “substituent” is another group bonded to a group serving as a mother nucleus.
  • the number of substituents may be one, or two or more. Two or more substituents may be the same or different. Terms such as “C1-6” indicate that the group serving as the mother nucleus has 1 to 6 carbon atoms. This number of carbon atoms does not include the number of carbon atoms present in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.
  • the “substituent” is not particularly limited as long as it is chemically acceptable and has the effects of the present invention.
  • the group that can be a “substituent” include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, and an s-butyl group A C1-6 alkyl group such as a group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; a C3-6 cycloalkyl group such as a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; Vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-buten
  • C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; vinyloxy group, allyloxy group, propenyl C2-6 alkenyloxy groups such as oxy and butenyloxy groups; C2-6 alkynyloxy groups such as ethynyloxy and propargyloxy groups; C6-10 aryl groups such as phenyl and naphthyl groups; phenoxy groups and 1-naphthoxy groups C7-10 aryloxy group such as benzyl group, phenethyl group, etc .; C7-11 aralkyloxy group such as benzyloxy group, phenethyloxy group; formyl group, acetyl group, propionyl group, benzoyl group, Such as cyclohexylcarbonyl group 1-7
  • C1-7 acylamino group C1-6 alkoxycarbonylamino group such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group; carbamoyl group; Substituted carbamoyl groups such as dimethylcarbamoyl group, phenylcarbamoyl group, N-phenyl-N-methylcarbamoyl group; imino C1-6 such as iminomethyl group, (1-imino) ethyl group, (1-imino) -n-propyl group Alkyl groups; hydroxyimino C1-6 alkyl groups such as hydroxyiminomethyl group, (1-hydroxyimino) ethyl group, (1-hydroxyimino) propyl group; methoxyiminomethyl group, (1-methoxyimino) ethyl group, etc.
  • C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group; C2-6 alkenylsulfinyl groups such as allylsulfinyl group; C2-6 alkynylsulfinyl groups such as propargylsulfinyl group; phenylsulfinyl group, etc.
  • 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl; pyridyl, pyrazinyl Groups, 6-membered heteroaryl groups such as pyrimidinyl group, pyridanidyl group, triazinyl group; saturated heterocyclic groups such as aziridinyl group, epoxy group, pyrrolidinyl group, tetrahydrofuranyl group, piperidyl group, piperazinyl group, morpholinyl group; trimethylsilyl group, triethyl Examples thereof include tri-C1-6 alkylsilyl groups such as silyl group and t-butyldimethylsilyl group; triphenylsilyl
  • substituteduents may have another “substituent” therein.
  • a butyl group as a substituent and an ethoxy group as another substituent, that is, an ethoxybutyl group may be used.
  • R represents a group represented by OR 1 , a group represented by NR 1 R 2 , a group represented by SR 1 , a group represented by S ( ⁇ O) R 3 , and a SO 2 R 3 group.
  • R 1 is a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, A substituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted group; An unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted carboxyl group, an unsubstituted or substituted carbamoyl group, a substituted sulfonyl group, or An amino group having a substituent or a substituent is shown.
  • the “C1-8 alkyl group” in R 1 is a saturated hydrocarbon group composed of 1 to 8 carbon atoms.
  • the C1-8 alkyl group may be linear or branched.
  • Examples of the C1-8 alkyl group include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, i-propyl group, i -Butyl group, s-butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like.
  • C1-6 alkyl groups are preferred.
  • Examples of the “substituted C1-8 alkyl group” include cycloalkylalkyl groups such as cyclopropylmethyl group, 2-cyclopropylethyl group, cyclopentylmethyl group, 2-cyclohexylethyl group, preferably C3-6 cycloalkylC1.
  • cycloalkenylalkyl group such as cyclopentenylmethyl group, 3-cyclopentenylmethyl group, 3-cyclohexenylmethyl group, 2- (3-cyclohexenyl) ethyl group, preferably C4-6 cycloalkenylC1 ⁇ 6 alkyl groups; fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2,2,2-trifluoroethyl Group 2,2,2-to Chloroethyl, pentafluoroethyl, 4-fluorobutyl, 4-chlorobutyl, 3,3,3-trifluoropropyl, 2,2,2-trifluoro-1-trifluoromethylethyl, perfluorohexyl Group, perchlorohexyl group, perfluorooo
  • Haloalkyl groups preferably C1-6 haloalkyl groups; arylalkyl groups (aralkyl groups) such as benzyl group, phenethyl group, 3-phenylpropyl group, 1-naphthylmethyl group, 2-naphthylmethyl group, preferably C6-10 An aryl C1-6 alkyl group;
  • 2-hydroxyiminoalkyl groups such as 2-hydroxyiminoethyl group, 2-hydroxyimino-1-methylethyl group, 2-hydroxy-1,1-dimethylethyl group, 2-hydroxyiminopropyl group, preferably 2-hydroxy An imino C2-6 alkyl group; an acylalkyl group such as an acetylmethyl group, 2-acetylethyl group, 3-acetylpropyl group, 1-acetyl-1-methylethyl group, 2-acetyl-1,1-dimethylethyl group; Preferably formyl C1-6 alkyl group; carboxyalkyl such as carboxymethyl group, 2-carboxyethyl group, 3-carboxypropyl group, 1-carboxy-1-methylethyl group, 2-carboxy-1,1-dimethylethyl group Group, preferably a carboxy C1-6 alkyl group; methoxycarbo An alkoxycarbonylalkyl group such
  • the “C2-8 alkenyl group” in R 1 is an unsaturated hydrocarbon group composed of 2 to 8 carbon atoms having at least one carbon-carbon double bond.
  • the C2-8 alkenyl group may be linear or branched.
  • C2-8 alkenyl groups include vinyl, 1-propenyl, isopropenyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3- Pentenyl group, 4-pentenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 1-heptenyl group, 6-heptenyl group, 1-octenyl group, 7- Examples include octenyl group, 1-methyl-allyl group, 2-methyl-allyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group and the like.
  • C2-6 alkenyl groups are preferred.
  • Examples of the “substituted C2-8 alkenyl group” include 3-chloro-2-propenyl group, 4-chloro-2-butenyl group, 4,4-dichloro-3-butenyl group, 4,4-difluoro-3 -Butenyl group, 3,3-dichloro-2-propenyl group, 2,3-dichloro-2-propenyl group, 3,3-difluoro-2-propenyl group, 2,4,6-trichloro-2-hexenyl group, etc.
  • Haloalkenyl groups preferably C2-6 haloalkenyl groups; hydroxyalkenyl such as 3-hydroxy-1-propenyl, 4-hydroxy-1-butenyl, 1-hydroxyallyl, 1-hydroxy-2-methylallyl Group, preferably a hydroxy C2-6 alkenyl group; and the like.
  • the “C2-8 alkynyl group” in R 1 is an unsaturated hydrocarbon group composed of 2 to 8 carbon atoms having at least one carbon-carbon triple bond.
  • the C2-8 alkynyl group may be linear or branched.
  • C2-8 alkynyl groups include ethynyl, 1-propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4 -Pentynyl, 1-hexynyl, 1-methyl-2-propynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 2-methyl-3-pentynyl, 1,1-dimethyl And a -2-butynyl group.
  • C2-6 alkynyl groups are preferred.
  • Examples of the “substituted C2-8 alkynyl group” include 3-chloro-1-propynyl group, 3-chloro-1-butynyl group, 3-bromo-1-butynyl group, 3-bromo-2-propynyl group, 3-iodo-2-propynyl group, 3-bromo-1-hexynyl group, 4,4,6,6-tetrafluoro-1-dodecynyl group, 5,5-dichloro-2-methyl-3-pentynyl group, 4 A haloalkynyl group such as a -chloro-1,1-dimethyl-2-butynyl group, preferably a C2-6 haloalkynyl group.
  • the “C3-8 cycloalkyl group” in R 1 is an alkyl group composed of 3 to 8 carbon atoms having a cyclic moiety.
  • Examples of the C3-8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. Of these, C3-6 cycloalkyl groups are preferred.
  • Examples of the “substituted C3-8 cycloalkyl group” include alkyl substitution such as 2,3,3-trimethylcyclobutyl group, 4,4,6,6-tetramethylcyclohexyl group, 1,3-dibutylcyclohexyl group, etc. Examples thereof include a cycloalkyl group, preferably a C3-6 cycloalkyl group in which 1 to 3 C1-6 alkyl groups are substituted.
  • the “C4-8 cycloalkenyl group” in R 1 is an alkenyl group composed of 4 to 8 carbon atoms having a cyclic moiety.
  • Examples of the C4-8 cycloalkenyl group include 1-cyclobutenyl group, 1-cyclopentenyl group, 3-cyclopentenyl group, 1-cyclohexenyl group, 3-cyclohexenyl group, 3-cycloheptenyl group, 4-cyclooctenyl group and the like. It is done.
  • Examples of the “substituted C4-8 cycloalkenyl group” include alkyl-substituted cycloalkenyl groups such as 2-methyl-3-cyclohexenyl group and 3,4-dimethyl-3-cyclohexenyl group, preferably C1-6 alkyl And C4-6 cycloalkenyl groups substituted with 1 to 3 groups.
  • the “C6-10 aryl group” in R 1 is a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.
  • the polycyclic aryl group as long as at least one ring is an aromatic ring, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring.
  • the C6-10 aryl group include phenyl group, naphthyl group, azulenyl group, indenyl group, indanyl group, tetralinyl group and the like. Of these, a phenyl group is preferred.
  • substituted C6-10 aryl group examples include 2-chlorophenyl group, 3,5-dichlorophenyl group, 4-fluorophenyl group, 3,5-difluorophenyl group, 4-trifluoromethylphenyl group, 2- Alkyl-substituted aryl group, halogeno-substituted aryl group, alkoxy-substituted aryl group such as methoxy-1-naphthyl group, preferably C1-6 alkyl-substituted C6-10 aryl group, halogeno-substituted C6-10 aryl group, C1-6 alkoxy-substituted An aryl group is mentioned.
  • the “heterocyclic group” in R 1 includes 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms.
  • the heterocyclic group may be monocyclic or polycyclic. Examples of the heterocyclic group include a 5-membered heteroaryl group, a 6-membered heteroaryl group, a condensed heteroaryl group, a saturated heterocyclic group, and a partially unsaturated heterocyclic group.
  • 5-membered heteroaryl groups include: pyrrolyl groups such as pyrrol-1-yl, pyrrol-2-yl, and pyrrol-3-yl; furyl groups such as furan-2-yl and furan-3-yl ; Thienyl groups such as thiophen-2-yl group and thiophen-3-yl group; imidazolyl groups such as imidazol-1-yl group, imidazol-2-yl group, imidazol-4-yl group and imidazol-5-yl group A pyrazolyl group such as a pyrazol-1-yl group, a pyrazol-3-yl group, a pyrazol-4-yl group, a pyrazol-5-yl group; an oxazol-2-yl group, an oxazol-4-yl group, an oxazole-5 -Oxazolyl groups such as yl groups; isoxazol-3-yl groups, isox
  • the 6-membered heteroaryl group includes pyridyl groups such as pyridin-2-yl group, pyridin-3-yl group and pyridin-4-yl group; pyrazinyl groups such as pyrazin-2-yl group and pyrazin-3-yl group A pyrimidinyl group such as a pyrimidin-2-yl group, a pyrimidin-4-yl group and a pyrimidin-5-yl group; a pyridazinyl group such as a pyridazin-3-yl group and a pyridazin-4-yl group; a triazinyl group; It is done.
  • Condensed heteroaryl groups include indol-1-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indol-6-yl, and indole -7-yl group; benzofuran-2-yl group, benzofuran-3-yl group, benzofuran-4-yl group, benzofuran-5-yl group, benzofuran-6-yl group, benzofuran-7-yl group; benzothiophene -2-yl group, benzothiophen-3-yl group, benzothiophen-4-yl group, benzothiophen-5-yl group, benzothiophen-6-yl group, benzothiophen-7-yl group; -Yl group, benzimidazol-2-yl group, benzimidazol-4-yl group, benzimidazol-5-i Group, benzoxazol-2-yl group,
  • heterocyclic groups include 3-membered saturated heterocycles such as aziridin-1-yl, aziridin-2-yl, and oxiranyl groups; pyrrolidin-1-yl, pyrrolidin-2-yl, and pyrrolidin-3 -5-membered saturated heterocycle such as -yl group, tetrahydrofuran-2-yl group, tetrahydrofuran-3-yl group, [1,3] dioxiran-2-yl group; piperidin-1-yl group, piperidin-2-yl Group, piperidin-3-yl group, piperidin-4-yl group, piperazin-1-yl group, piperazin-2-yl group, morpholin-2-yl group, morpholin-3-yl group, morpholin-4-yl group 6-membered saturated heterocycle such as 1,3-benzodioxol-4-yl group, 1,3-benzodioxol-5-yl group, 1,4-benzodi
  • heterocyclic group having a substituent a 4-chloro-2-pyridinyl group, a 3-chloro-2-pyrazinyl group, a 4-methyl-2-pyridinyl group, a 5-trifluoromethyl-2-pyrimidinyl group, Examples include 3-methyl-2-quinolyl group.
  • the “C1-8 acyl group” in R 1 is a carbonyl group having a hydrogen atom, a C1-7 alkyl group, a C2-7 alkenyl group, a C2-7 alkynyl group, a C6-7 aryl group or a 5-7 membered heterocyclic ring. A group to which a group is bonded.
  • C1-8 acyl group includes formyl group; acetyl group, propionyl group, n-propylcarbonyl group, n-butylcarbonyl group, pentanoyl group, valeryl group, octanoyl group, i-propylcarbonyl group, i-butylcarbonyl group, An alkylcarbonyl group such as a pivaloyl group and an isovaleryl group, preferably a C1-6 alkylcarbonyl group; an alkenylcarbonyl group such as an acryloyl group and a methacryloyl group, preferably a C2-6 alkenylcarbonyl group; an alkynylcarbonyl group such as a propioroyl group, preferably C2-6 alkynylcarbonyl groups; arylcarbonyl groups such as benzoyl groups; heterocyclic carbonyl groups such as 2-pyridylcarbonyl groups and thienyl
  • Examples of the “substituted C1-8 acyl group” include a monofluoroacetyl group, a monochloroacetyl group, a monobromoacetyl group, a difluoroacetyl group, a dichloroacetyl group, a dibromoacetyl group, a trifluoroacetyl group, a trichloroacetyl group, a trichloroacetyl group, Haloacyl groups such as bromoacetyl group, 3,3,3-trifluoropropionyl group, 3,3,3-trichloropropionyl group, 2,2,3,3,3-pentafluoropropionyl group, preferably C1-7 haloacyl Groups and the like.
  • the “carboxyl group having a substituent” in R 1 is a carbonyl group having a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C6-10 aryl group, a C6-10 aryl C1-6 alkyl. Or a group to which a 5- or 6-membered heterocyclic group is bonded.
  • Examples of the “substituted carboxyl group” include methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, t-butoxycarbonyl group, n
  • An alkoxycarbonyl group such as a pentyloxycarbonyl group or an n-hexyloxycarbonyl group, preferably a C1-6 alkoxycarbonyl group; an alkenyloxycarbonyl group such as a vinyloxycarbonyl group or an allyloxycarbonyl group, preferably a C2-6 alkenyloxy
  • An alkynyloxycarbonyl group such as an ethynyloxycarbonyl group or a propargyloxycarbonyl group, preferably a C2-6 alkynyloxycarbonyl group; a phenoxycarbonyl group, a naphthoxy
  • the “carbamoyl group having a substituent” in R 1 is a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 6-10 aryl group, a C 6-10 aryl C 1-6 alkyl group. Or a group to which a 5- to 6-membered heterocyclic group is bonded.
  • a monoalkylcarbamoyl group such as a methylcarbamoyl group, an ethylcarbamoyl group, a dimethylcarbamoyl group, a diethylcarbamoyl group or a dialkylcarbamoyl group, preferably a monoC1-6 alkylcarbamoyl group or a diC1 ⁇ 6 alkylcarbamoyl group; monoarylcarbamoyl group such as phenylcarbamoyl group and 4-methylphenylcarbamoyl group, preferably monoC6-10 arylcarbamoyl group.
  • Examples of the “sulfonyl group having a substituent” in R 1 include a methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, i-propylsulfonyl group, n-butylsulfonyl group, i-butylsulfonyl group, s-butyl.
  • Alkylsulfonyl groups such as sulfonyl group, t-butylsulfonyl group, n-pentylsulfonyl group, i-pentylsulfonyl group, neopentylsulfonyl group, 1-ethylpropylsulfonyl group, n-hexylsulfonyl group, i-hexylsulfonyl group, Preferably a C1-6 alkylsulfonyl group; a haloalkylsulfonyl group such as a trifluoromethylsulfonyl group, preferably a C1-6 haloalkylsulfonyl group; an arylsulfonyl group such as a phenylsulfonyl group, a 4-methylphenylsulfonyl group, preferably C6-10 arylsulfonyl group;
  • an alkylamino group such as a methylamino group, an ethylamino group, an n-propylamino group, an n-butylamino group, a dimethylamino group or a diethylamino group, preferably a mono-C1-6 alkyl Amino group or di-C1-6 alkylamino group; mono-C1-6 alkylideneamino group such as methylideneamino group, ethylideneamino group; monoarylamino group such as phenylamino group, 4-methylphenylamino group, preferably monoC6-10 Arylamino group; diarylamino group such as di1-naphthylamino group, preferably diC6-10 arylamino group; aralkylamino group such as benzylamino group, preferably C6-10 arylC1-6 alkylamino group; ace
  • R 2 represents a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, A substituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted group; Having a heterocyclic group, an unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted carboxyl group, an unsubstituted or substituted carbamoyl group, a substituted sulfonyl group, unsubstituted Or a hydroxyl group having a substituent, or an amino group having no substituent or a substituent.
  • R 2 “C1-8 alkyl group”, “C2-8 alkenyl group”, “C2-8 alkynyl group”, “C3-8 cycloalkyl group”, “C4-8 cycloalkenyl group”, “C6-10” “Aryl group”, “heterocyclic group”, “C1-8 acyl group”, “carboxyl group having substituent”, “carbamoyl group having substituent”, “sulfonyl group having substituent”, “having substituent”
  • Examples of the “amino group” are the same as those exemplified for R 1 .
  • the “hydroxyl group having a substituent” in R 2 includes a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, a decyloxy group, a dodecyloxy group, and lauryl.
  • a cycloalkylalkoxy group such as a cyclopropylmethyloxy group and a 2-cyclopentylethyloxy group, preferably a C3-8 cycloalkyl C1-6 alkoxy group; an aralkyloxy group such as a benzyloxy group, preferably a C6-10 aryl C1-6 Alkoxy group; chloromethoxy group, dichloromethoxy group, trichloromethoxy group, trifluoromethoxy group, 1-fluoroethoxy group, 1,1-difluoroethoxy group, 2,2,2-trifluoroethoxy group, pentafluoroethoxy group, etc.
  • a haloalkoxy group preferably a C1-6 haloalkoxy group; vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1-pentenyloxy group, 2-pentenyl group Oxy group, 3-pentenyloxy group, 4-pentenyloxy group, 1-hexenyloxy group, 2-hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group, 1-methyl-2 An alkenyloxy group such as a propenyloxy group, a 2-methyl-2-propenyloxy group, a 1-methyl-2-butenyloxy group, or a 2-methyl-2-butenyloxy group, preferably a C2-6 alkenyloxy group;
  • R 3 is an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, unsubstituted or A substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted heterocycle A group, an unsubstituted or substituted mercapto group, an unsubstituted or substituted hydroxyl group, or an unsubstituted or substituted amino group.
  • an alkylthio group such as a methylthio group and an ethylthio group, preferably a C1-6 alkylthio group
  • an arylthio group such as a phenylthio group and a 4-methylphenylthio group, preferably C6 To 10 arylthio groups
  • acylthio groups such as acetylthio group and benzoylthio group, preferably C1 to 6 acylthio groups
  • R 4 is an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, unsubstituted or A substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted hetero A ring group is shown.
  • R 5 is an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, unsubstituted or A substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted hetero A ring group is shown.
  • R 1 and R 2 may be combined to form an unsubstituted or substituted 3- to 8-membered ring, or ⁇ CR a R b or ⁇ N—R c may be formed.
  • the 3- to 8-membered ring include saturated heterocycles such as an aziridine ring, a pyrrolidine ring, a piperidine ring, a piperazine ring, and a morpholine ring.
  • R a and R b each independently have a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted group A C2-8 alkynyl group, an unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, Unsubstituted or substituted heterocyclic group, unsubstituted or substituted C1-8 acyl group, unsubstituted or substituted carboxyl group, unsubstituted or substituted carbamoyl group, substituted group A sulfonyl group having, an unsubstituted or substituted mercapto group, an unsubstituted or substituted hydroxyl group, or unsubstituted Or an amino group having
  • R a and R b “C1-8 alkyl group”, “C2-8 alkenyl group”, “C2-8 alkynyl group”, “C3-8 cycloalkyl group”, “C4-8 cycloalkenyl group”, “ “C6-10 aryl group”, “heterocyclic group”, “C1-8 acyl group”, “carboxyl group having substituent”, “carbamoyl group having substituent”, “sulfonyl group having substituent”, “substituted”
  • Examples of the “amino group having a group” are the same as those exemplified for R 1 .
  • Examples of the “hydroxyl group having a substituent” in R a and R b are the same as those exemplified for R 2 .
  • Examples of the “mercapto group having a substituent” in R a and R b are the same as those exemplified for R 3 .
  • R c represents an unsubstituted or substituted hydroxyl group, or an unsubstituted or substituted C1-8 alkyl group.
  • Examples of the “C1-8 alkyl group” in R c are the same as those exemplified for R 1 .
  • Examples of the “hydroxyl group having a substituent” in R c include the same groups as those exemplified for R 2 .
  • R 4 R 5 , R 4 and R 5 may be combined to form an unsubstituted or substituted 5- to 8-membered ring.
  • the 5- to 8-membered ring include sulfur-containing saturated hetero rings such as a tetrahydrothiophene ring, a tetrahydrothiopyran ring, and a [1.4] oxathian ring.
  • X 1 is each independently an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, Unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C4-8 cycloalkenyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted An unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted (1-imino) C1-8 alkyl group, an unsubstituted or substituted carboxyl group, Unsubstituted or substituted carbamoyl group, unsubstituted or substituted hydroxyl group, unsubstituted or substituted amino group Mercapto group with an unsubstituted or substituted group, a s
  • the “(1-imino) C1-8 alkyl group” in X 1 is an iminomethyl group or a group in which a C1-7 alkyl group is bonded to an iminomethyl group.
  • the (1-imino) C1-8 alkyl group includes an iminomethyl group, a (1-imino) ethyl group, a (1-imino) propyl group, a (1-imino) butyl group, a (1-imino) pentyl group, (1 -Imino) hexyl group, (1-imino) heptyl group and the like. Of these, (1-imino) C1-6 alkyl groups are preferred.
  • the “(1-imino) C1-8 alkyl group having a substituent” includes a hydroxyiminomethyl group, a (1-hydroxyimino) ethyl group, a (1-hydroxyimino) propyl group, and a (1-hydroxyimino) butyl group.
  • (1-hydroxyimino) alkyl group such as, preferably (1-hydroxyimino) C1-6 alkyl group; methoxyiminomethyl group, (1-ethoxyimino) methyl group, (1-methoxyimino) ethyl group, (1 A (1-alkoxyimino) alkyl group such as a -t-butoxyimino) ethyl group or a (1-ethoxyimino) ethyl group, preferably a (1- (C1-6 alkoxy) imino) C1-6 alkyl group; It is done.
  • halogeno group examples include a fluoro group, a chloro group, a bromo group, and an iodo group.
  • [B, D] B represents a carbon atom or a nitrogen atom. That is, a pyridine ring condensed with “D” or a pyrazine ring condensed with “D” is formed. D represents a 5- to 7-membered heterocycle substituted with been 5-7 membered hydrocarbon ring or an unsubstituted or X 1, substituted by unsubstituted or X 1.
  • the 5- to 7-membered hydrocarbon ring includes an aromatic hydrocarbon ring such as a benzene ring; a C5-7 cycloalkene ring such as a cyclopentene ring, cyclohexene ring, and cycloheptene ring; a furan ring, a thiophene ring, a pyrrole ring, and an imidazole ring.
  • the compound according to the present invention is preferably a compound having a quinoline ring or a quinoxaline ring.
  • X 2 each independently represents an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, Unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C4-8 cycloalkenyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted An unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted (1-imino) C1-8 alkyl group, an unsubstituted or substituted carboxyl group, Unsubstituted or substituted carbamoyl group, unsubstituted or substituted hydroxyl group, unsubstituted or substituted amino group Mercapto group with an unsubstituted or substituted group, a s
  • Examples of the “mercapto group having a substituent” in X 2 include the same as those exemplified for R 3 .
  • "(1-imino) C1 ⁇ 8 alkyl group”, "halogeno group” may be the same as those exemplified for X 1.
  • Any one of X 2 and R may be combined with each other to form an unsubstituted or substituted 5- to 8-membered ring.
  • [E] E shows unsubstituted or 5- to 7-membered hydrocarbon ring substituted with X 2, or unsubstituted or a 5-7 membered heterocyclic ring substituted with X 2.
  • an aromatic hydrocarbon ring such as a benzene ring; a C5-7 cycloalkene ring such as a cyclopentene ring, cyclohexene ring, and cycloheptene ring; a furan ring, a thiophene ring, a pyrrole ring, and an imidazole ring , Pyrazole ring, thiazole ring, oxazole ring, isoxazole ring, isothiazole ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, azepine ring, diazepine ring and other aromatic 5-
  • X represents an oxygen atom (O), a nitrogen atom (NH), or a nitrogen atom (NR ′′) substituted with a C1-8 alkyl group (R ′′).
  • R ′′ examples of the “C1-8 alkyl group” are the same as those exemplified for R 1 .
  • the salt of the compound of the present invention is not particularly limited as long as it is an agriculturally and horologically acceptable salt.
  • the salt include salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium and potassium; salts of alkaline earth metals such as calcium and magnesium; Examples include salts of transition metals such as iron and copper; salts of organic bases such as ammonia, triethylamine, tributylamine, pyridine, and hydrazine.
  • the compound of the present invention is preferably a compound represented by the formula (II) (hereinafter sometimes referred to as “compound (II)”).
  • R, X 1 , m, X 2, n, D, B, and X are as defined respectively in the above formula (I).
  • [A 1, A 2, A 3 , A 4 ] A 1 , A 2 , A 3 , and A 4 each independently represent a carbon atom or a nitrogen atom. That is, it forms a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, or a triazine ring.
  • the compound of the present invention is preferably a compound represented by the formula (III) (hereinafter sometimes referred to as “compound (III)”).
  • the compound represented by the formula (III) is a compound in which “D” is a benzene ring. That is, the compound of the present invention is preferably a compound having a quinoline ring or a quinoxaline ring.
  • R, X 1 , m, X 2, n, A 1, A 2, A 3, A 4, B, and X are as defined above.
  • the compound of the present invention is preferably a compound represented by the formula (IV) (hereinafter sometimes referred to as “compound (IV)”).
  • the compound represented by the formula (IV) is a compound in which “D” is a benzene ring and “A 1 to A 4 ” are carbon atoms. That is, the compound of the present invention is preferably a compound having either a quinoline ring or a quinoxaline ring and a benzene ring.
  • R, X 1 , m, X 2 , n, B, and X have the same meaning as described above.
  • the compound of the present invention is preferably a compound represented by the formula (V) (hereinafter sometimes referred to as “compound (V)”).
  • R, X 1 , m, X 2 , n, D, B, and X have the same meaning as in the above formula (I).
  • a 5, A 6, A 7 each independently represent a carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom. However, oxygen atoms, sulfur atoms, or a combination of oxygen atoms and sulfur atoms are not adjacent to each other.
  • the ring containing A 5 , A 6 , and A 7 constitutes a furan ring, a thiophene ring, a pyrrole ring, an imidazole ring, a pyrazole ring, a thiazole ring, an oxazole ring, an isoxazole ring, and an isothiazole ring.
  • the compound of the present invention is preferably a compound represented by the formula (VI) (hereinafter sometimes referred to as “compound (VI)”).
  • the compound represented by the formula (VI) is a compound in which “D” is a benzene ring.
  • R, X 1 , m, X 2 , n, A 5 , A 6 , A 7 , B, and X have the same meaning as in the above formula (V). .
  • the compound of the present invention can be produced, for example, by the synthesis method shown below.
  • Compound (II) can be produced by reacting the compound represented by formula (1) with the compound represented by formula (2) by a known method.
  • R, X 1 , m, X 2 , n, D, A 1 to A 4 , B, and X have the same meaning as described above.
  • Q represents a halogeno group.
  • 7,8-difluoro-3-iodo-quinoline is a useful production intermediate.
  • the salt of the compound according to the present invention can be prepared by bringing a compound (I) into contact with an inorganic acid compound, an organic acid compound, an alkali metal compound, an alkaline earth metal compound, a transition metal compound, an ammonium compound, or the like.
  • the target product can be efficiently isolated by subjecting it to conventional post-treatment operations in synthetic organic chemistry and, if necessary, conventionally known separation and purification means.
  • the structure of the target product can be identified and confirmed by measuring 1 H-NMR spectrum, IR spectrum, mass spectrum, elemental analysis, etc.
  • the agricultural and horticultural fungicide according to the present invention contains at least one selected from the nitrogen-containing heterocyclic compound or a salt thereof according to the present invention as an active ingredient.
  • the agricultural and horticultural fungicides of the present invention belong to a wide variety of filamentous fungi, for example, algae fungi (Oomycetes), Ascomycetes, Deuteromycetes, and Basidiomycetes Has excellent bactericidal power against bacteria.
  • algae fungi Oomycetes
  • Ascomycetes Ascomycetes
  • Deuteromycetes Deuteromycetes
  • Basidiomycetes Has excellent bactericidal power against bacteria.
  • the agricultural and horticultural fungicide of the present invention is used in methods such as seed treatment, foliage application, soil application, and water surface application for the control of various diseases that occur during the cultivation of agricultural and horticultural crops including flowers, turf, and grass. can do.
  • Sugar beet brown spot (Cercospora beticola), black root (Aphanomyces cochlloides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris);
  • Peanut brown spot (Mycosphaerella arachidis), black astringency (Mycosphaerella berkeleyi);
  • Cucumber powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), vine blight (Mycosphaerella melonis), vine split disease (Fusarium oxysporum), mycorrhizal disease (Sclerotinia sclerotiorum), gray mold disease (Botrytis cinerea) Anthracnose (Colletotrichum orbiculare), black spot (Cladosporium cucumerinum), brown spot (Corynespora cassicola), seedling blight (Pyth
  • Tomato gray mold (Botrytis cinerea), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans); Eggplant: gray mold (Botrytis cinerea), black blight (Corynespora melongenae), powdery mildew (Erysiphe cichoracearum), subtle mold (Mycovellosiella nattrassii);
  • Barley leafy leaf disease (Pyrenophora graminea), cloud shape disease (Rhynchosporium secalis), naked smut (Ustilago tritici, U.nuda); Rice: Rice Blast (Pyricularia oryzae), Rhizoctonia solani, Idiot Seedling (Gibberella fujikuroi), Sesame Leaf Blight (Cochliobolus niyabeanus), Seedling Blight (Pythium graminicolum), White Leaf Blight (Xanthomonas oryzae) Bacterial disease (Burkholderia plantarii), Brown disease (Acidovorax avenae), Bacterial disease (Burkholderia glumae); Tobacco: Sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum); Tulip: Gray mold disease (Botrytis cinerea); Bentgrass:
  • the agricultural and horticultural fungicide of the present invention has an excellent bactericidal effect against resistant bacteria.
  • the resistant bacteria include gray mold fungus (Botrytis cinerea), sugar beet brown fungus (Cercospora beticola), apple black rot fungus (Venturia inaequalis), pear black scab (Venturia nashicola); a gray mold fungus (Botrytis cinerea) resistant to dicarboximide fungicides (for example, vinclozolin, procymidone, iprodione) and the like.
  • dicarboximide fungicides for example, vinclozolin, procymidone, iprodione
  • More preferable diseases to which the agricultural and horticultural fungicide of the present invention is applied include black scab of apple, gray mold of cucumber, powdery mildew of wheat, plague of tomato, leaf rust of wheat, rice blast of rice, cucumber Examples include vine split disease.
  • the agricultural and horticultural fungicide of the present invention is a highly safe drug with little phytotoxicity, low toxicity to fish and warm-blooded animals.
  • the agricultural and horticultural fungicide of the present invention should be used in the form that can be taken as an agrochemical, that is, in the form of an agrochemical formulation such as a wettable powder, a granule, a powder, an emulsion, an aqueous solvent, a suspension, or a granular wettable powder. Can do.
  • Additives and carriers used in solid formulations include vegetable powders such as soybean flour and wheat flour, mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay, sodium benzoate, urea And organic and inorganic compounds such as mirabilite.
  • Solvents used in liquid formulations include kerosene, xylene and petroleum aromatic hydrocarbons, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, vegetable oil, water, etc. Can be mentioned.
  • a surfactant can be added as necessary.
  • the surfactant that can be added is not particularly limited.
  • alkyl phenyl ether added with polyoxyethylene alkyl ether added with polyoxyethylene, higher fatty acid ester added with polyoxyethylene, sorbitan higher fatty acid ester added with polyoxyethylene, tristyryl added with polyoxyethylene
  • Nonionic surfactants such as phenyl ether, sulfates of alkylphenyl ethers added with polyoxyethylene, alkylbenzene sulfonates, sulfates of higher alcohols, alkylnaphthalene sulfonates, polycarboxylates, lignin sulfones Acid salt, formaldehyde condensate of alkyl naphthalene sulfonate, and isobutylene-maleic anhydride copolymer.
  • the wettable powder, emulsion, flowable powder, aqueous solvent, or granular wettable powder thus obtained is diluted with water to a predetermined concentration and sprayed on plants as a solution, suspension or emulsion. Can be used. In addition, powders and granules can be used by spraying them on plants as they are.
  • the amount of the active ingredient in the agricultural and horticultural fungicide of the present invention is preferably 0.01 to 90% by weight, more preferably 0.05 to 85% by weight, based on the whole preparation.
  • the application amount of the agricultural and horticultural fungicide of the present invention varies depending on weather conditions, formulation form, application time, application method, application place, disease to be controlled, target crop, etc., but it is usually 1 in terms of the amount of active ingredient compound per hectare. ⁇ 1,000 g, preferably 10 to 100 g.
  • the applied concentration is 1 to 1000 ppm, preferably 10 to 250 ppm.
  • the agricultural and horticultural fungicide of the present invention may be mixed with other fungicides, insecticides / acaricides, and synergists.
  • the agricultural and horticultural fungicide of the present invention and other fungicides, insecticides / acaricides, and synergists can be used simultaneously or in succession.
  • Typical examples of other fungicides, insecticides / miticides, and plant growth regulators that can be used in combination are shown below.
  • Fungicide (1) benzimidazole series: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate methyl, etc .; (2) Dicarboximide type: Clozolinate, iprodione, procymidone, vinclozolin and the like; (3) DMI-bactericidal system: imazalyl, oxpoconazole, pefazoate, prochloraz, triflumizole, triphorin, pyrifenox, fenarimol, nuarimol, azaconazole, viteltanol, bromconazole, cyproconazole, difenoconazole, diniconazole, Epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafor, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propicon
  • N-phenyl carbamate type dietofencarb and the like
  • QoI-bactericidal (Qo inhibitor) system azoxystrobin, picoxystrobin, pyraclostrobin, cresoxime-methyl, trifloxystrobin, dimoxystrobin, metminostrobin, orizastrobin, Famoxadone, floxastrobin, phenamidon, metminophen, etc .
  • PP fungicide (phenylpyrrole) type fenpiconyl, fludioxonil, etc .
  • Quinoline series quinoxyphene and the like
  • AH disinfectant (aromatic hydrocarbon) series biphenyl, chloronebu, dichlorane, kintozen, technazen, torquetophos-methyl, etc .
  • MBI-R series fusaride, pyrokilone, tricyclazole, etc .
  • MBI-D system carprop
  • phthalamic acid type teclophthalam, etc .
  • Benzotriazine type triazoxide and the like
  • benzenesulfonamide series fursulfamide and the like
  • Pyridazinone Dichromedin and the like
  • CAA disinfectant (carboxylic amide) type dimethomorph, fulmorph, benchavaricarb, iprovaricarb, mandipropamide and the like
  • Tetracycline oxytetracycline and the like
  • Thiocarbamate type metasulfocarb, etc.
  • Oxidative phosphorylation inhibitor compounds cyhexatin, diafenthiuron, phenbutatin oxide, propargite, azocyclotin; (12) molting disrupting compound: cyromazine; (13) Mixed function oxidase inhibitor compound: piperonyl butoxide; (14) Sodium channel blocker compounds: indoxacarb, metaflumizone; (15) Microbial pesticides: BT agent, entomopathogenic virus agent, entomopathogenic fungus agent, nematode pathogenic fungus agent; Bacillus spp.
  • Latrophilin receptor agonist depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside
  • Octopaminergic agent Amitraz
  • Ryanodine derivative agonist fulvendiamide, chlorantraniliprole, cyantraliniprol
  • Inhibitors of magnesium-stimulated ATPase thiocyclam, thiosultap, nereistoxin; (21) antifeedant: pymetrozine; (22) Tick growth inhibitor: clofentezin, etoxazole; (23) Others: Benclothiaz, Bifenazate, Pyridalyl, Sulfur, Sienopyraphene, Ciflumethofene, Amidoflumet, Tetradiphone, Chlordimeform, 1,3-Dichloropropene, DCIP, Phenisobromolate, Benzomate, Metaaldehyde, Spinetram, Pyrifluquinazone, Benzo Ximate, bromopropyrate, quinomethionate, chlorbenzilate, chloropicrin, clothiazoben, dicyclanyl, phenoxacrime, fentriphanyl, flubenzimine, flufenzine, gossip lure, japony
  • Plant growth regulator Abscisic acid, indole butyric acid, uniconazole, etiquelozate, etephone, cloxiphonac, chlormecote, chlorella extract, calcium peroxide, cyanamide, dichlorprop, gibberellin, daminozide, decyl alcohol, trinexapac ethyl, mepicoat chloride, pack Lobutrazole, paraffin wax, piperonyl butoxide, pyraflufenethyl, flurprimidol, prohydrojasmon, prohexadione calcium salt, benzylaminopurine, pendimethalin, forchlorphenuron, potassium maleate hydrazide, 1-naphthyl Acetamide, 4-CPA, MCPB, choline, oxyquinoline sulfate, ethiclozate, butorualine, 1-methylcyclopropene, abiglycine hydrochloride;
  • Example 1 8-Fluoro-3- (3-fluoro-2- (propane-2-sulfinyl) -phenoxy) -quinoline [8-fluoro-3- [3-fluoro-2- (propane-2-sulfinyl) -phenoxy]- quinoline] (Compound No. 1-13)
  • a 50 mL flask was charged with 0.37 g (2.27 mmol) of 8-fluoro-3-quinolinol and 10 mL of N, N-dimethylformamide.
  • Step 1 5-Fluoro-2- (3-fluoro-2-isopropylsulfanylphenoxy) quinoxaline (5-fluoro-2- (3-fluoro-2-isopropylsulfanylphenoxy)- Synthesis of quinoxaline) 0.14 g (0.75 mmol) of 2-chloro-5-fluoroquinoxaline and 3-fluoro-2-isopropylsulfanylphenol To 10 mL of 14 g (0.75 mmol) of dimethylformamide solution, 0.12 g (0.90 mmol) of potassium carbonate was added at room temperature. Subsequently, it heated up at 100 degreeC and stirred for 4 hours.
  • the solution was poured into a separatory funnel containing 100 mL of ethyl acetate and 100 mL of water, and separated into an aqueous layer and an organic layer.
  • the aqueous layer was extracted with 100 mL of ethyl acetate and the organic layer was separated.
  • the resulting organic layers were combined and it was washed with 50 mL brine and dried over magnesium sulfate. It was then filtered and the solvent was distilled off under reduced pressure.
  • Step 2 Synthesis of 5-fluoro-2- [3-fluoro-2- (propane-2-sulfonyl) phenoxy] quinoxaline (Compound No. a1-10) 0.23 g (0.69 mmol) of 5-fluoro-2- (3-fluoro-2-isopropylsulfanylphenoxy) -quinoxaline was dissolved in a mixed solvent of 4 mL of 2-propanol: 2 mL of water. To this was added 0.98 g (1.58 mmol) of oxone [DuPont Peroxymonosulfate] and stirred at room temperature for 20 hours.
  • oxone DuPont Peroxymonosulfate
  • the solution was poured into a separatory funnel containing 100 mL of ethyl acetate and 100 mL of water, and separated into an aqueous layer and an organic layer.
  • the aqueous layer was extracted with 100 mL of ethyl acetate and the organic layer was separated.
  • the obtained organic layer was mixed. It was washed with 50 mL brine and dried over magnesium sulfate. It was then filtered and the solvent was distilled off under reduced pressure.
  • Step 1 Synthesis of 6-fluoro-3,4-dihydro-1H-quinoxalin-2-one 40.0 g of 2,4-difluoronitrobenzene was dissolved in 400 mL of acetonitrile, 35.1 g of glycine ethyl ester hydrochloride, diisopropyl 32.3 g of ethylamine was added and the mixture was heated to reflux for 15 hours. The reaction solution was cooled to room temperature, concentrated under reduced pressure to a volume of about 1/3, added to water, and extracted with ethyl acetate.
  • Step 2 Synthesis of 2-chloro-6-fluoroquinoxaline 23.9 g of 6-fluoro-3,4-dihydro-1H-quinoxalin-2-one and 37.6 g of manganese dioxide were added to 300 ml of benzene, The mixture was heated to reflux for 6 hours while dehydrating. The reaction solution was cooled to room temperature, filtered through Celite, and the insoluble material was washed with 1 L of acetone and 1 L of ethyl acetate. The filtrates were combined, the solvent was distilled off under reduced pressure, and the residue was washed successively with a small amount of ethyl acetate and acetone to obtain 1.7 g of crystals.
  • Step 3 Synthesis of 3-chloro-2- (propane-2-sulfonyl) phenol 150.7 g of 2,6-dichlorothiophenol and 171.7 g of isopropyl iodide were dissolved in 2.5 L of acetonitrile, and potassium carbonate 174 .5 g was added and heated to reflux for 3 hours. The reaction mixture was cooled to room temperature, the solvent was evaporated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 204.3 g of crude crystals of isopropyl 2,6-dichlorophenyl sulfide.
  • Step 4 Synthesis of 6-fluoro-2- [3-chloro-2- (propane-2-sulfonyl) phenoxy] quinoxaline 35.64 g of 2-chloro-6-fluoroquinoxaline, 3-chloro-2- (propane- 2-sulfonyl) phenol (45.82 g) was dissolved in 586 mL of dimethylformamide, 32.38 g of potassium carbonate was added, and the mixture was stirred at 100 ° C. for 24 hours. The reaction solution was cooled to room temperature, added to water, and extracted with ethyl acetate.
  • Tables 1 to 8 show the nitrogen-containing heterocyclic compounds obtained in the above Examples and the nitrogen-containing heterocyclic compounds that can be synthesized by the same method as in any of the above Examples.
  • R, (X 1 ) m, (X 2 ) n, and X in Tables 1 and 2 represent those in formula (1-A).
  • R, (X 1 ) m, (X 2 ) n, and X in Table 3 represent those in formula (1-B).
  • R, (X 1 ) m, B, (X 2 ) n, A 2 to A 4 , and X in Table 4 represent those in formula (1-C).
  • R, (X 1 ) m, B, (X 2 ) n, A 6 , A 7 , and X in Table 5 represent those in formula (1-D).
  • R, (X 1 ) m, B, (X 2 ) n, A 3 , and X in Table 6 represent those in formula (1-E).
  • R, B, (X 2 ) n, A 3 , and X in Table 7 represent those in formula (1-F).
  • R, B, (X 2 ) n, A 3 , and X in Table 8 represent those in formula (1-G).
  • melting point (° C.) or refractive index (n D ) is shown.
  • the superscript number of (n D ) indicates the measurement temperature (° C.).
  • Compound 1-5 5.07 (s, 2H), 7.02 (m, 1H), 7.05-7.23 (m, 8H), 7.32 (d, 1H), 7.47 (m, 1H), 7.57-7.63 (m, 2H) , 8.10 (d, 1H), 8.85 (d, 1H).
  • Compound 1-8 1.37 (d, 6H), 2.76 (m, 1H), 7.03 (t, 1H), 7.36-7.63 (m, 5H), 7.71-7.87 (m, 3H), 8.28 (s, 1H) , 8.81 (d, 1H).
  • Compound 1-14 3.31 (s, 3H), 7.06 (m, 1H), 7.34-7.42 (m, 2H), 7.48-7.53 (m, 2H), 7.64-7.71 (m, 2H), 8.14 (m, 1H), 8.90 (d, 1H).
  • Compound 1-17 3.40 (s, 3H), 7.01 (m, 1H), 7.3-7.7 (m, 6H), 8.87 (d, 1H).
  • Compound 2-7 3.31 (s, 3H), 3.73 (s, 3H), 6.92 (m, 1H), 7.04-7.15 (m, 3H), 7.23-7.42 (m, 3H), 8.22 (d, 1H) .
  • Compound 2-11 4.28 (s, 4H), 6.71 (dd, 1H), 7.00 (m, 1H), 7.15-7.45 (m, 15H), 8.60 (d, 1H).
  • Compound 2-16 1.92 (s, 3H), 3.29 (s, 3H), 6.97 (m, 1H), 7.28-7.41 (m, 3H), 7.50-7.53 (m, 2H), 7.65 (m, 1H) , 8.78 (d, 1H).
  • Formulation Example 3 Dust The nitrogen-containing heterocyclic compound of the present invention 10 parts Clay 90 parts The above is uniformly mixed and finely pulverized to obtain a powder of 10% active ingredient.
  • Formulation Example 4 Granules Nitrogen-containing heterocyclic compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctyl sulfosuccinate sodium salt 1 part Potassium phosphate 1 part The above was pulverized and mixed well, and water was added and kneaded well. Thereafter, granulation and drying are performed to obtain a granule containing 5% of the active ingredient.
  • Nitrogen-containing heterocyclic compound of the present invention 10 parts Polyoxyethylene alkyl allyl ether 4 parts Polycarboxylic acid sodium salt 2 parts Glycerin 10 parts Xanthan gum 0.2 parts Water 73.8 parts Wet mill until the particle size is 3 microns or less to obtain a 10% active ingredient suspension.
  • Formulation Example 6 Granule wettable powder Nitrogen-containing heterocyclic compound of the present invention 40 parts Clay 36 parts Potassium chloride 10 parts Alkylbenzenesulfonic acid sodium salt 1 part Ligninsulfonic acid sodium salt 8 parts Formaldehyde condensate of alkylbenzenesulfonic acid sodium salt 5 parts After the above is uniformly mixed and finely pulverized, an appropriate amount of water is added and then kneaded to form a clay. The clay-like product is granulated and then dried to obtain a granule wettable powder containing 40% of the active ingredient.
  • the lesion appearance on the leaves was compared with the untreated seedlings to determine the control effect.
  • a paddy rice blast disease water surface application test was conducted on the compounds of compound numbers a1-4, a1-5, a1-10, a1-11, a1-12, and a1-13. As a result, all the compounds showed a control value of 60% or more.

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Abstract

A nitrogen-containing heterocyclic compound represented by formula (I) or a salt thereof; and a bactericide for agricultural or horticultural use, which contains, as an active ingredient, at least one substance that is selected from among the nitrogen-containing heterocyclic compounds represented by formula (I) and salts thereof. R: OR1, SO2R3 or the like (wherein R1,3: a substituted or unsubstituted C1-8 alkyl group or the like) B: a nitrogen atom or a carbon atom D, E: a 5-7 membered hydrocarbon ring or the like X1,2: a halogeno group or the like X: an oxygen atom or the like m: 0-5 n: 0-3

Description

含窒素ヘテロ環化合物および農園芸用殺菌剤Nitrogen-containing heterocyclic compounds and agricultural and horticultural fungicides
　本発明は、効果が確実で安全に使用できる農園芸用殺菌剤および農園芸用殺菌剤の有効成分として有用な含窒素ヘテロ環化合物に関する。
　本願は、２０１１年６月２８日に、日本に出願された特願２０１１－１４３４７９号、及び２０１２年１月１６日に、日本に出願された特願２０１２－００６２７９号に基づき優先権を主張し、その内容をここに援用する。 The present invention relates to an agricultural and horticultural fungicide that can be used safely and safely, and to a nitrogen-containing heterocyclic compound useful as an active ingredient of an agricultural and horticultural fungicide.
This application claims priority based on Japanese Patent Application No. 2011-143479 filed in Japan on June 28, 2011 and Japanese Patent Application No. 2012-006279 filed in Japan on January 16, 2012. , The contents of which are incorporated herein.
　農園芸作物の病害に対して多数の防除薬剤が使用されている。しかし、従来の防除薬剤の多くは、その防除効力が不十分であったり、薬剤耐性の病原菌の出現によりその使用が制限されたり、植物体に薬害や汚染を生じさせたり、若しくは人畜魚類に対する毒性や環境への影響が大きかったりなどで、十分に満足できるものではなかった。そのため、かかる欠点の少ない薬剤の出現が強く要望されている。 A large number of control agents are used against diseases of agricultural and horticultural crops. However, many of the conventional control chemicals have insufficient control efficacy, their use is limited by the emergence of drug-resistant pathogens, cause phytotoxicity and pollution to plants, or are toxic to human and livestock fish. And the impact on the environment was not enough. For this reason, there is a strong demand for the appearance of drugs with few such defects.
　本発明に関連して、特許文献１または２には、本発明化合物と類似の化学構造を有するキノリン誘導体、およびそれを有効成分として含有する農園芸用殺菌剤が開示されている。 In connection with the present invention, Patent Document 1 or 2 discloses a quinoline derivative having a chemical structure similar to that of the compound of the present invention, and an agricultural and horticultural fungicide containing it as an active ingredient.
ＷＯ２００５／０７０９１７WO2005 / 0700917 ＷＯ２００７／０１１０２２WO2007 / 011022
　本発明は、効果が確実で安全に使用できる農園芸用殺菌剤、並びに農園芸用殺菌剤の有効成分として有用な含窒素ヘテロ環化合物またはその塩を提供することを課題とする。 An object of the present invention is to provide an agricultural and horticultural fungicide that can be used safely and reliably, and a nitrogen-containing heterocyclic compound or a salt thereof useful as an active ingredient of the agricultural and horticultural fungicide.
　本発明者らは、上記課題を解決すべく鋭意検討した。その結果、式（I）で表される含窒素ヘテロ環化合物およびその塩を得るに至った。この含窒素ヘテロ環化合物は農園芸用殺菌剤の有効成分として効果が確実で安全に使用できることを見出した。本発明は、これらの知見に基づきさらに検討を重ね完成するに至った。 The present inventors diligently studied to solve the above problems. As a result, a nitrogen-containing heterocyclic compound represented by the formula (I) and a salt thereof were obtained. The present inventors have found that this nitrogen-containing heterocyclic compound has a certain effect and can be used safely as an active ingredient of agricultural and horticultural fungicides. The present invention has been completed by further studies based on these findings.
　すなわち、本発明は以下の態様を包含する。
〔１〕　式（I）で表される含窒素ヘテロ環化合物またはその塩。 That is, the present invention includes the following aspects.
[1] A nitrogen-containing heterocyclic compound represented by the formula (I) or a salt thereof.
Figure JPOXMLDOC01-appb-C000007
Figure JPOXMLDOC01-appb-C000007
式（I）中、Ｒは、ＯＲ1で表される基、ＮＲ1Ｒ2で表される基、ＳＲ1で表される基、Ｓ（＝Ｏ）Ｒ3で表される基、ＳＯ2Ｒ3で表される基、Ｓ(＝Ｏ)(＝ＮＲ4)Ｒ5で表される基、Ｎ＝Ｓ(＝Ｏ)Ｒ4Ｒ5で表される基、またはニトロ基を示す。
　Ｒ1は、水素原子、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、置換基を有するスルホニル基、または無置換の若しくは置換基を有するアミノ基を示す。
　Ｒ2は、水素原子、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、置換基を有するスルホニル基、無置換の若しくは置換基を有する水酸基、または無置換の若しくは置換基を有するアミノ基を示す。
　Ｒ3は、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有するメルカプト基、無置換の若しくは置換基を有する水酸基、または無置換の若しくは置換基を有するアミノ基を示す。
　Ｒ4およびＲ5は、それぞれ独立に、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、または無置換の若しくは置換基を有するヘテロ環基を示す。
　ＮＲ1Ｒ2で表される基において、Ｒ1とＲ2とが一緒になって、無置換の若しくは置換基を有する３～８員環、＝ＣＲaＲb、または＝Ｎ－Ｒcを形成してもよい。
　ＲaおよびＲbは、それぞれ独立に、水素原子、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、置換基を有するスルホニル基、無置換の若しくは置換基を有するメルカプト基、無置換の若しくは置換基を有する水酸基、または無置換の若しくは置換基を有するアミノ基を示す。
　Ｒcは、無置換の若しくは置換基を有する水酸基、または無置換の若しくは置換基を有するＣ１～８アルキル基を示す。
　Ｎ＝Ｓ(＝Ｏ)Ｒ4Ｒ5で表される基において、Ｒ4とＲ5とが一緒になって、無置換の若しくは置換基を有する５～８員環を形成してもよい。 In the formula (I), R represents a group represented by OR 1 , a group represented by NR 1 R 2 , a group represented by SR 1 , a group represented by S (═O) R 3 , SO 2 A group represented by R 3 , a group represented by S (═O) (═NR 4 ) R 5 , a group represented by N═S (═O) R 4 R 5 , or a nitro group.
R 1 is a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, A substituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted group; An unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted carboxyl group, an unsubstituted or substituted carbamoyl group, a substituted sulfonyl group, or An amino group having a substituent or a substituent is shown.
R 2 represents a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, A substituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted group; Having a heterocyclic group, an unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted carboxyl group, an unsubstituted or substituted carbamoyl group, a substituted sulfonyl group, unsubstituted Or a hydroxyl group having a substituent, or an amino group having no substituent or a substituent.
R 3 is an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, unsubstituted or A substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted heterocycle A group, an unsubstituted or substituted mercapto group, an unsubstituted or substituted hydroxyl group, or an unsubstituted or substituted amino group.
R 4 and R 5 are each independently an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 An alkynyl group, an unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, or unsubstituted Or a heterocyclic group having a substituent.
In the group represented by NR 1 R 2 , R 1 and R 2 are taken together to form an unsubstituted or substituted 3- to 8-membered ring, ═CR a R b , or ═N—R c . It may be formed.
R a and R b each independently have a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted group A C2-8 alkynyl group, an unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, Unsubstituted or substituted heterocyclic group, unsubstituted or substituted C1-8 acyl group, unsubstituted or substituted carboxyl group, unsubstituted or substituted carbamoyl group, substituted group A sulfonyl group having, an unsubstituted or substituted mercapto group, an unsubstituted or substituted hydroxyl group, or unsubstituted Or an amino group having a substituent.
R c represents an unsubstituted or substituted hydroxyl group, or an unsubstituted or substituted C1-8 alkyl group.
In the group represented by N═S (═O) R 4 R 5 , R 4 and R 5 may be combined to form an unsubstituted or substituted 5- to 8-membered ring.
　Ｘ1は、それぞれ独立に、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有する（１－イミノ）Ｃ１～８アルキル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、無置換の若しくは置換基を有する水酸基、無置換の若しくは置換基を有するアミノ基、無置換の若しくは置換基を有するメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、またはニトロ基を示す。
　ｍは、Ｘ1の個数を示し且つ０～５のいずれかの整数である。
　Ｂは、炭素原子または窒素原子を示す。
　Ｄは、無置換の若しくはＸ1で置換された５～７員炭化水素環、または無置換の若しくはＸ1で置換された５～７員ヘテロ環を示す。 X 1 is each independently an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, Unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C4-8 cycloalkenyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted An unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted (1-imino) C1-8 alkyl group, an unsubstituted or substituted carboxyl group, Unsubstituted or substituted carbamoyl group, unsubstituted or substituted hydroxyl group, unsubstituted or substituted amino group Mercapto group with an unsubstituted or substituted group, a sulfonyl group having a substituent, a halogeno group, a cyano group or a nitro group.
m represents the number of X 1 and is an integer from 0 to 5.
B represents a carbon atom or a nitrogen atom.
D represents a 5- to 7-membered heterocycle substituted with been 5-7 membered hydrocarbon ring or an unsubstituted or X 1, substituted by unsubstituted or X 1.
　Ｘ2は、それぞれ独立に、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有する（１－イミノ）Ｃ１～８アルキル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、無置換の若しくは置換基を有する水酸基、無置換の若しくは置換基を有するアミノ基、無置換の若しくは置換基を有するメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、またはニトロ基を示す。
　ｎは、Ｘ2の個数を示し且つ０～３のいずれかの整数である。
　Ｘ2のいずれかひとつと、Ｒとが一緒になって、無置換の若しくは置換基を有する５～８員環を形成してもよい。
　Ｅは、無置換の若しくはＸ２で置換された５～７員炭化水素環、または無置換の若しくはＸ２で置換された５～７員ヘテロ環を示す。
　Ｘは、酸素原子（Ｏ）、窒素原子（ＮＨ）、またはＣ１～８アルキル基（Ｒ”）で置換された窒素原子（ＮＲ”）を示す。 X 2 each independently represents an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, Unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C4-8 cycloalkenyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted An unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted (1-imino) C1-8 alkyl group, an unsubstituted or substituted carboxyl group, Unsubstituted or substituted carbamoyl group, unsubstituted or substituted hydroxyl group, unsubstituted or substituted amino group Mercapto group with an unsubstituted or substituted group, a sulfonyl group having a substituent, a halogeno group, a cyano group or a nitro group.
n represents the number of X 2 and is an integer from 0 to 3.
Any one of X 2 and R may be combined with each other to form an unsubstituted or substituted 5- to 8-membered ring.
E shows unsubstituted or 5- to 7-membered hydrocarbon ring substituted with X 2, or unsubstituted or a 5-7 membered heterocyclic ring substituted with X 2.
X represents an oxygen atom (O), a nitrogen atom (NH), or a nitrogen atom (NR ″) substituted with a C1-8 alkyl group (R ″).
〔２〕上記〔１〕に記載された式（I）が、式（II）で表されることを特徴とする含窒素ヘテロ環化合物またはその塩。 [2] A nitrogen-containing heterocyclic compound or a salt thereof, wherein the formula (I) described in the above [1] is represented by the formula (II).
Figure JPOXMLDOC01-appb-C000008
Figure JPOXMLDOC01-appb-C000008
上記の式（II）中、Ｒ、Ｘ1、ｍ、Ｘ2、ｎ、Ｄ、Ｂ、およびＸは、上記〔１〕に記載の式（I）中のそれぞれと同じ意味を示す。
　Ａ１、Ａ２、Ａ３、およびＡ４は、それぞれ独立して、炭素原子または窒素原子を示す。 In the above formula (II), R, X 1 , m, X 2 , n, D, B, and X have the same meaning as in formula (I) described in [1] above.
A 1 , A 2 , A 3 , and A 4 each independently represent a carbon atom or a nitrogen atom.
〔３〕上記〔２〕に記載された式(II)が、式（III）で表されることを特徴とする含窒素ヘテロ環化合物、またはその塩。 [3] A nitrogen-containing heterocyclic compound or a salt thereof, wherein the formula (II) described in the above [2] is represented by the formula (III).
Figure JPOXMLDOC01-appb-C000009
Figure JPOXMLDOC01-appb-C000009
　上記の式（III）中、Ｒ、Ｘ1、ｍ、Ｘ2、ｎ、Ａ１、Ａ２、Ａ３、Ａ４、Ｂ、およびＸは、上記〔２〕に記載の式（II）中のそれぞれと同じ意味を示す。 In the above formula (III), R, X 1 , m, X 2 , n, A 1 , A 2 , A 3 , A 4 , B, and X are in the formula (II) described in [2] above. It has the same meaning as each of.
〔４〕上記〔１〕に記載された式(I)が、式（IV）で表されることを特徴とする含窒素ヘテロ環化合物、またはその塩。 [4] A nitrogen-containing heterocyclic compound or a salt thereof, wherein the formula (I) described in [1] above is represented by the formula (IV).
Figure JPOXMLDOC01-appb-C000010
Figure JPOXMLDOC01-appb-C000010
　上記の式（IV）中、Ｒ、Ｘ1、ｍ、Ｘ2、ｎ、Ｂ、およびＸは、上記〔１〕に記載の式（I）中のそれぞれと同じ意味を示す。 In the above formula (IV), R, X 1 , m, X 2 , n, B, and X have the same meaning as in formula (I) described in [1] above.
〔５〕上記〔１〕に記載された式(I)が、式（V）で表されることを特徴とする含窒素ヘテロ環化合物またはその塩。 [5] A nitrogen-containing heterocyclic compound or a salt thereof, wherein the formula (I) described in the above [1] is represented by the formula (V).
Figure JPOXMLDOC01-appb-C000011
Figure JPOXMLDOC01-appb-C000011
式（V）中、Ｒ、Ｘ1、ｍ、Ｘ2、ｎ、Ｄ、Ｂ、およびＸは、上記〔１〕に記載の式（I）中のそれぞれと同じ意味を示す。
　Ａ５、Ａ６、およびＡ７は、それぞれ独立して、炭素原子、窒素原子、酸素原子、または硫黄原子を示す。ただし、酸素原子同士、硫黄原子同士、酸素原子と硫黄原子の組合わせが隣接することはない。 In formula (V), R, X 1 , m, X 2 , n, D, B, and X have the same meaning as in formula (I) described in [1] above.
A 5 , A 6 , and A 7 each independently represent a carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom. However, oxygen atoms, sulfur atoms, or a combination of oxygen atoms and sulfur atoms are not adjacent to each other.
〔６〕上記〔５〕に記載された式(V)が、式（VI）で表されることを特徴とする含窒素ヘテロ環化合物またはその塩。 [6] A nitrogen-containing heterocyclic compound or a salt thereof, wherein the formula (V) described in the above [5] is represented by the formula (VI).
Figure JPOXMLDOC01-appb-C000012
Figure JPOXMLDOC01-appb-C000012
式（VI）中、Ｒ、Ｘ1、ｍ、Ｘ2、ｎ、Ａ５、Ａ６、Ａ７、Ｂ、およびＸは、上記〔５〕に記載の式（V）中のそれぞれと同じ意味を示す。） In the formula (VI), R, X 1 , m, X 2 , n, A 5 , A 6 , A 7 , B, and X have the same meaning as in the formula (V) described in [5] above. Indicates. )
〔７〕　上記〔１〕～〔６〕のいずれか１項に記載の含窒素ヘテロ環化合物またはその塩から選ばれる少なくとも１種を有効成分として含有する農園芸用殺菌剤。 [7] An agricultural and horticultural fungicide containing as an active ingredient at least one selected from the nitrogen-containing heterocyclic compound or a salt thereof according to any one of [1] to [6] above.
　本発明の含窒素ヘテロ環化合物は、農園芸用殺菌剤の有効成分などとして有用な新規化合物である。
　本発明の農園芸用殺菌剤は、確実で優れた防除効果を有し、植物体に薬害を生じることがなく、人畜魚類に対する毒性や環境への影響が少ない、安全な薬剤である。 The nitrogen-containing heterocyclic compound of the present invention is a novel compound useful as an active ingredient for agricultural and horticultural fungicides.
The agricultural and horticultural fungicide of the present invention is a safe drug that has a reliable and excellent control effect, does not cause phytotoxicity to plants, and has little toxicity to human and livestock and environmental impact.
　以下、本発明を、１）含窒素ヘテロ環化合物と、２）農園芸用殺菌剤とに項分けして詳細に説明するが、本発明はこれらの例に限定されることはない。本発明の趣旨を逸脱しない範囲で、構成の付加、省略、置換、およびその他の変更が可能である。 Hereinafter, the present invention will be described in detail by dividing it into 1) nitrogen-containing heterocyclic compounds and 2) agricultural and horticultural fungicides, but the present invention is not limited to these examples. Additions, omissions, substitutions, and other modifications can be made without departing from the spirit of the present invention.
１）含窒素ヘテロ環化合物
〔式（I）で表される化合物〕
　本発明に係る含窒素ヘテロ環化合物は、式（I）で表される化合物（以下、「化合物（I）」と表記することがある。）である。 1) Nitrogen-containing heterocyclic compound [compound represented by formula (I)]
The nitrogen-containing heterocyclic compound according to the present invention is a compound represented by the formula (I) (hereinafter sometimes referred to as “compound (I)”).
　本発明に係る含窒素ヘテロ環化合物には、水和物、各種溶媒和物や結晶多形などが含まれる。さらに、本発明に係る含窒素ヘテロ環化合物は、不斉炭素原子、二重結合などに基づく立体異性体およびそれらの混合物を包含する。 The nitrogen-containing heterocyclic compound according to the present invention includes hydrates, various solvates and crystal polymorphs. Furthermore, the nitrogen-containing heterocyclic compound according to the present invention includes stereoisomers based on asymmetric carbon atoms, double bonds, and the like, and mixtures thereof.
　まず、式（I）における、「無置換の」および「置換基を有する」の意味を説明する。
　「無置換の」の用語は、母核となる基のみであることを意味する。「置換基を有する」との記載がなく母核となる基の名称のみで記載しているときは、別段の断りがない限り「無置換の」意味である。
　一方、「置換基を有する」の用語は、母核となる基のいずれかの水素原子が、母核と同種または異種の構造の基で置換されていることを意味する。従って、「置換基」は、母核となる基に結合した他の基である。置換基は１つであってもよいし、２つ以上であってもよい。２つ以上の置換基は同一であってもよいし、異なるものであってもよい。
　「Ｃ１～６」などの用語は、母核となる基の炭素原子数が１～６個などであることを表している。この炭素原子数には、置換基の中に在る炭素原子の数を含まない。例えば、置換基としてエトキシ基を有するブチル基は、Ｃ２アルコキシＣ４アルキル基に分類する。 First, the meanings of “unsubstituted” and “having a substituent” in formula (I) will be described.
The term “unsubstituted” means only the group that is the mother nucleus. When there is no description of “having a substituent” and only the name of the group serving as a mother nucleus is used, it means “unsubstituted” unless otherwise specified.
On the other hand, the term “having a substituent” means that any hydrogen atom of a group serving as a mother nucleus is substituted with a group having the same or different structure as the mother nucleus. Accordingly, the “substituent” is another group bonded to a group serving as a mother nucleus. The number of substituents may be one, or two or more. Two or more substituents may be the same or different.
Terms such as “C1-6” indicate that the group serving as the mother nucleus has 1 to 6 carbon atoms. This number of carbon atoms does not include the number of carbon atoms present in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.
　「置換基」は化学的に許容され、本発明の効果を有する限りにおいて特に制限されない。
　「置換基」となり得る基としては、　フルオロ基、クロロ基、ブロモ基、ヨード基などのハロゲノ基；　メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基などのＣ１～６アルキル基；　シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などのＣ３～６シクロアルキル基；　ビニル基、１－プロペニル基、２－プロペニル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、１－メチル－２－プロペニル基、２－メチル－２－プロペニル基、１－ペンテニル基、２－ペンテニル基、３－ペンテニル基、４－ペンテニル基、１－メチル－２－ブテニル基、２－メチル－２－ブテニル基、１－ヘキセニル基、２－ヘキセニル基、３－ヘキセニル基、４－ヘキセニル基、５－ヘキセニル基などのＣ２～６アルケニル基；　２－シクロプロペニル基、２－シクロペンテニル基、３－シクロヘキセニル基などのＣ３～６シクロアルケニル基；　エチニル基、１－プロピニル基、２－プロピニル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、１－メチル－２－プロピニル基、２－メチル－３－ブチニル基、１－ペンチニル基、２－ペンチニル基、３－ペンチニル基、４－ペンチニル基、１－メチル－２－ブチニル基、２－メチル－３－ペンチニル基、１－ヘキシニル基、１，１－ジメチル－２－ブチニル基などのＣ２～６アルキニル基； The “substituent” is not particularly limited as long as it is chemically acceptable and has the effects of the present invention.
Examples of the group that can be a “substituent” include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, and an s-butyl group A C1-6 alkyl group such as a group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; a C3-6 cycloalkyl group such as a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; Vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group C2-6 alkenyl groups such as nyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group; C3-6 cycloalkenyl groups such as 2-cyclopropenyl group, 2-cyclopentenyl group, 3-cyclohexenyl group Ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl Group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group A C2-6 alkynyl group such as;
　メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；　ビニルオキシ基、アリルオキシ基、プロペニルオキシ基、ブテニルオキシ基などのＣ２～６アルケニルオキシ基；　エチニルオキシ基、プロパルギルオキシ基などのＣ２～６アルキニルオキシ基；　フェニル基、ナフチル基などのＣ６～１０アリール基；　フェノキシ基、１－ナフトキシ基などのＣ６～１０アリールオキシ基；　ベンジル基、フェネチル基などのＣ７～１１アラルキル基；　ベンジルオキシ基、フェネチルオキシ基などのＣ７～１１アラルキルオキシ基；　ホルミル基、アセチル基、プロピオニル基、ベンゾイル基、シクロヘキシルカルボニル基などのＣ１～７アシル基；　ホルミルオキシ基、アセチルオキシ基、プロピオニルオキシ基、ベンゾイルオキシ基、シクロヘキシルカルボニルオキシ基などのＣ１～７アシルオキシ基；　メトキシカルボニル基、エトキシカルボニル基、ｎ－プロポキシカルボニル基、ｉ－プロポキシカルボニル基、ｎ－ブトキシカルボニル基、ｔ－ブトキシカルボニル基などのＣ１～６アルコキシカルボニル基；　カルボキシル基； C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; vinyloxy group, allyloxy group, propenyl C2-6 alkenyloxy groups such as oxy and butenyloxy groups; C2-6 alkynyloxy groups such as ethynyloxy and propargyloxy groups; C6-10 aryl groups such as phenyl and naphthyl groups; phenoxy groups and 1-naphthoxy groups C7-10 aryloxy group such as benzyl group, phenethyl group, etc .; C7-11 aralkyloxy group such as benzyloxy group, phenethyloxy group; formyl group, acetyl group, propionyl group, benzoyl group, Such as cyclohexylcarbonyl group 1-7 acyl groups; C1-7 acyloxy groups such as formyloxy group, acetyloxy group, propionyloxy group, benzoyloxy group, cyclohexylcarbonyloxy group; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i- C1-6 alkoxycarbonyl groups such as propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group; carboxyl group;
　水酸基；　オキソ基；　クロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基、パーフルオロ－ｎ－ペンチル基などのＣ１～６ハロアルキル基；　２－クロロ－１－プロペニル基、２－フルオロ－１－ブテニル基などのＣ２～６ハロアルケニル基；　４，４－ジクロロ－１－ブチニル基、４－フルオロ－１－ペンチニル基、５－ブロモ－２－ペンチニル基などのＣ２～６ハロアルキニル基；　２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基などのＣ１～６ハロアルコキシ基；　２－クロロプロペニルオキシ基、３－ブロモブテニルオキシ基などのＣ２～６ハロアルケニルオキシ基；　４－クロロフェニル基、４－フルオロフェニル基、２，４－ジクロロフェニル基などのＣ６～１０ハロアリール基；　４－フルオロフェニルオキシ基、４－クロロ－１－ナフトキシ基などのＣ６～１０ハロアリールオキシ基；　クロロアセチル基、トリフルオロアセチル基、トリクロロアセチル基、４－クロロベンゾイル基などのＣ１～７ハロアシル基； Hydroxyl group; oxo group; C1-6 haloalkyl such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group Groups; C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group and 2-fluoro-1-butenyl group; 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5- C2-6 haloalkynyl groups such as bromo-2-pentynyl group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group and 2,3-dichlorobutoxy group; 2-chloropropenyloxy group, 3-bromo C2-6 haloalkenyloxy groups such as butenyloxy groups; 4-chlorophenyl group, 4-fluorophenyl group, 2,4-dichloro C6-10 haloaryl group such as phenyl group; C6-10 haloaryloxy group such as 4-fluorophenyloxy group, 4-chloro-1-naphthoxy group; chloroacetyl group, trifluoroacetyl group, trichloroacetyl group, 4- A C1-7 haloacyl group such as a chlorobenzoyl group;
　シアノ基；　イソシアノ基；　ニトロ基；　イソシアナト基；　シアナト基；　アジド基；　アミノ基；　メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基などのＣ１～６アルキルアミノ基；　アニリノ基、ナフチルアミノ基などのＣ６～１０アリールアミノ基；　ベンジルアミノ基、フェニルエチルアミノ基などのＣ７～１１アラルキルアミノ基；　ホルミルアミノ基、アセチルアミノ基、プロパノイルアミノ基、ブチリルアミノ基、ｉ－プロピルカルボニルアミノ基、ベンゾイルアミノ基などのＣ１～７アシルアミノ基；　メトキシカルボニルアミノ基、エトキシカルボニルアミノ基、ｎ－プロポキシカルボニルアミノ基、ｉ－プロポキシカルボニルアミノ基などのＣ１～６アルコキシカルボニルアミノ基；　カルバモイル基；　ジメチルカルバモイル基、フェニルカルバモイル基、Ｎ－フェニル－Ｎ－メチルカルバモイル基などの置換カルバモイル基；　イミノメチル基、（１－イミノ）エチル基、（１－イミノ）－ｎ－プロピル基などのイミノＣ１～６アルキル基；　ヒドロキシイミノメチル基、（１－ヒドロキシイミノ）エチル基、（１－ヒドロキシイミノ）プロピル基などのヒドロキシイミノＣ１～６アルキル基；メトキシイミノメチル基、（１－メトキシイミノ）エチル基などのＣ１～６アルコキシイミノＣ１～６アルキル基； Cyano group; isocyano group; nitro group; isocyanato group; cyanato group; azide group; amino group; C1-6 alkylamino group such as methylamino group, dimethylamino group and diethylamino group; C6 ~ such as anilino group and naphthylamino group 10 arylamino group; C7-11 aralkylamino group such as benzylamino group and phenylethylamino group; formylamino group, acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group, benzoylamino group, etc. C1-7 acylamino group; C1-6 alkoxycarbonylamino group such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group; carbamoyl group; Substituted carbamoyl groups such as dimethylcarbamoyl group, phenylcarbamoyl group, N-phenyl-N-methylcarbamoyl group; imino C1-6 such as iminomethyl group, (1-imino) ethyl group, (1-imino) -n-propyl group Alkyl groups; hydroxyimino C1-6 alkyl groups such as hydroxyiminomethyl group, (1-hydroxyimino) ethyl group, (1-hydroxyimino) propyl group; methoxyiminomethyl group, (1-methoxyimino) ethyl group, etc. A C1-6 alkoxyimino C1-6 alkyl group;
　メルカプト基；　イソチオシアナト基；　チオシアナト基；　メチルチオ基、エチルチオ基、ｎ－プロピルチオ基、ｉ－プロピルチオ基、ｎ－ブチルチオ基、ｉ－ブチルチオ基、ｓ－ブチルチオ基、ｔ－ブチルチオ基などのＣ１～６アルキルチオ基；　ビニルチオ基、アリルチオ基などのＣ２～６アルケニルチオ基；　エチニルチオ基、プロパルギルチオ基などのＣ２～６アルキニルチオ基；　フェニルチオ基、ナフチルチオ基などのＣ６～１０アリールチオ基；　チアゾリルチオ基、ピリジルチオ基などのヘテロアリールチオ基；　ベンジルチオ基、フェネチルチオ基などのＣ７～１１アラルキルチオ基；　（メチルチオ）カルボニル基、（エチルチオ）カルボニル基、（ｎ－プロピルチオ）カルボニル基、（ｉ－プロピルチオ）カルボニル基、（ｎ－ブチルチオ）カルボニル基、（ｉ－ブチルチオ）カルボニル基、（ｓ－ブチルチオ）カルボニル基、（ｔ－ブチルチオ）カルボニル基などの（Ｃ１～６アルキルチオ）カルボニル基； Mercapto group; isothiocyanato group; thiocyanato group; C1-6 alkylthio such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group Groups: C2-6 alkenylthio groups such as vinylthio groups and allylthio groups; C2-6 alkynylthio groups such as ethynylthio groups and propargylthio groups; C6-10 arylthio groups such as phenylthio groups and naphthylthio groups; thiazolylthio groups and pyridylthio groups Heteroarylthio groups of C7-11 aralkylthio groups such as benzylthio group and phenethylthio group; (methylthio) carbonyl group, (ethylthio) carbonyl group, (n-propylthio) carbonyl group, (i-propylthio) carbo Le group, (n- butylthio) carbonyl group, (i-butylthio) carbonyl group, (s-butylthio) carbonyl group, (t-butylthio) (C1 ~ 6 alkylthio), such as a carbonyl group a carbonyl group;
　メチルスルフィニル基、エチルスルフィニル基、ｔ－ブチルスルフィニル基などのＣ１～６アルキルスルフィニル基；　アリルスルフィニル基などのＣ２～６アルケニルスルフィニル基；　プロパルギルスルフィニル基などのＣ２～６アルキニルスルフィニル基；　フェニルスルフィニル基などのＣ６～１０アリールスルフィニル基；　チアゾリルスルフィニル基、ピリジルスルフィニル基などのヘテロアリールスルフィニル基；　ベンジルスルフィニル基、フェネチルスルフィニル基などのＣ７～１１アラルキルスルフィニル基；　メチルスルホニル基、エチルスルホニル基、ｔ－ブチルスルホニル基などのＣ１～６アルキルスルホニル基；　アリルスルホニル基などのＣ２～６アルケニルスルホニル基；　プロパルギルスルホニル基などのＣ２～６アルキニルスルホニル基；　フェニルスルホニル基などのＣ６～１０アリールスルホニル基；　チアゾリルスルホニル基、ピリジルスルホニル基などのヘテロアリールスルホニル基；　ベンジルスルホニル基、フェネチルスルホニル基などのＣ７～１１アラルキルスルホニル基； C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group; C2-6 alkenylsulfinyl groups such as allylsulfinyl group; C2-6 alkynylsulfinyl groups such as propargylsulfinyl group; phenylsulfinyl group, etc. C6-10 arylsulfinyl group of the above; heteroarylsulfinyl group such as thiazolylsulfinyl group, pyridylsulfinyl group; C7-11 aralkylsulfinyl group such as benzylsulfinyl group, phenethylsulfinyl group; methylsulfonyl group, ethylsulfonyl group, t- C1-6 alkylsulfonyl groups such as butylsulfonyl group; C2-6 alkenylsulfonyl groups such as allylsulfonyl group; propargylsulfonyl group C2-6 alkynylsulfonyl groups of C6-10 arylsulfonyl groups such as phenylsulfonyl groups; heteroarylsulfonyl groups such as thiazolylsulfonyl groups and pyridylsulfonyl groups; C7-11 aralkylsulfonyl groups such as benzylsulfonyl groups and phenethylsulfonyl groups Group;
　ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などの５員ヘテロアリール基；　ピリジル基、ピラジニル基、ピリミジニル基、ピリダニジル基、トリアジニル基などの６員ヘテロアリール基；　アジリジニル基、エポキシ基、ピロリジニル基、テトラヒドロフラニル基、ピペリジル基、ピペラジニル基、モルホリニル基などの飽和ヘテロ環基；　トリメチルシリル基、トリエチルシリル基、ｔ－ブチルジメチルシリル基などのトリＣ１～６アルキルシリル基；　トリフェニルシリル基；などを挙げることができる。 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl; pyridyl, pyrazinyl Groups, 6-membered heteroaryl groups such as pyrimidinyl group, pyridanidyl group, triazinyl group; saturated heterocyclic groups such as aziridinyl group, epoxy group, pyrrolidinyl group, tetrahydrofuranyl group, piperidyl group, piperazinyl group, morpholinyl group; trimethylsilyl group, triethyl Examples thereof include tri-C1-6 alkylsilyl groups such as silyl group and t-butyldimethylsilyl group; triphenylsilyl group;
　また、これらの「置換基」はそれの中にさらに別の「置換基」を有するものであってもよい。例えば、置換基としてのブチル基に、別の置換基としてエトキシ基を有するもの、すなわち、エトキシブチル基のようなものであってもよい。 These “substituents” may have another “substituent” therein. For example, a butyl group as a substituent and an ethoxy group as another substituent, that is, an ethoxybutyl group may be used.
〔Ｒ〕
　Ｒは、ＯＲ1で表される基、ＮＲ1Ｒ2で表される基、ＳＲ1で表される基、Ｓ（＝Ｏ）Ｒ3で表される基、ＳＯ2Ｒ3で表される基、Ｓ(＝Ｏ)(＝ＮＲ4)Ｒ5で表される基、Ｎ＝Ｓ(＝Ｏ)Ｒ4Ｒ5で表される基、またはニトロ基を示す。 [R]
R represents a group represented by OR 1 , a group represented by NR 1 R 2 , a group represented by SR 1 , a group represented by S (═O) R 3 , and a SO 2 R 3 group. A group represented by a group, S (═O) (═NR 4 ) R 5 , a group represented by N═S (═O) R 4 R 5 , or a nitro group;
〔Ｒ1〕
　Ｒ1は、水素原子、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、置換基を有するスルホニル基、または無置換の若しくは置換基を有するアミノ基を示す。 [R 1 ]
R 1 is a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, A substituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted group; An unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted carboxyl group, an unsubstituted or substituted carbamoyl group, a substituted sulfonyl group, or An amino group having a substituent or a substituent is shown.
　Ｒ1における、「Ｃ１～８アルキル基」は、炭素原子１～８個で構成される飽和炭化水素基である。Ｃ１～８アルキル基は直鎖であってもよいし、分岐鎖であってもよい。Ｃ１～８アルキル基としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｎ－ヘプチル基、ｎ－オクチル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｉ－ペンチル基、ネオペンチル基、２－メチルブチル基、２，２－ジメチルプロピル基、ｉ－ヘキシル基などが挙げられる。これらのうち、Ｃ１～６アルキル基が好ましい。 The “C1-8 alkyl group” in R 1 is a saturated hydrocarbon group composed of 1 to 8 carbon atoms. The C1-8 alkyl group may be linear or branched. Examples of the C1-8 alkyl group include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, i-propyl group, i -Butyl group, s-butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like. Of these, C1-6 alkyl groups are preferred.
　「置換基を有するＣ１～８アルキル基」としては、　シクロプロピルメチル基、２－シクロプロピルエチル基、シクロペンチルメチル基、２－シクロヘキシルエチル基などのシクロアルキルアルキル基、好ましくはＣ３～６シクロアルキルＣ１～６アルキル基；　シクロペンテニルメチル基、３－シクロペンテニルメチル基、３－シクロヘキセニルメチル基、２－（３－シクロヘキセニル）エチル基などのシクロアルケニルアルキル基、好ましくはＣ４～６シクロアルケニルＣ１～６アルキル基；　フルオロメチル基、クロロメチル基、ブロモメチル基、ジフルオロメチル基、ジクロロメチル基、ジブロモメチル基、トリフルオロメチル基、トリクロロメチル基、トリブロモメチル基、２，２，２－トルフルオロエチル基、２，２，２－トリクロロエチル基、ペンタフルオロエチル基、４－フルオロブチル基、４－クロロブチル基、３，３，３－トリフルオロプロピル基、２，２，２－トリフルオロ－１－トリフルオロメチルエチル基、パーフルオロヘキシル基、パークロロヘキシル基、パーフルオロオクチル基、パークロロオクチル基、２，４，６－トリクロロヘキシル基、パーフルオロデシル基、２，２，４，４，６，６－へキサクロロオクチル基などのハロアルキル基、好ましくはＣ１～６ハロアルキル基；　ベンジル基、フェネチル基、３－フェニルプロピル基、１－ナフチルメチル基、２－ナフチルメチル基などのアリールアルキル基（アラルキル基）、好ましくはＣ６～１０アリールＣ１～６アルキル基； Examples of the “substituted C1-8 alkyl group” include cycloalkylalkyl groups such as cyclopropylmethyl group, 2-cyclopropylethyl group, cyclopentylmethyl group, 2-cyclohexylethyl group, preferably C3-6 cycloalkylC1. ~ 6 alkyl group; cycloalkenylalkyl group such as cyclopentenylmethyl group, 3-cyclopentenylmethyl group, 3-cyclohexenylmethyl group, 2- (3-cyclohexenyl) ethyl group, preferably C4-6 cycloalkenylC1 ~ 6 alkyl groups; fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2,2,2-trifluoroethyl Group 2,2,2-to Chloroethyl, pentafluoroethyl, 4-fluorobutyl, 4-chlorobutyl, 3,3,3-trifluoropropyl, 2,2,2-trifluoro-1-trifluoromethylethyl, perfluorohexyl Group, perchlorohexyl group, perfluorooctyl group, perchlorooctyl group, 2,4,6-trichlorohexyl group, perfluorodecyl group, 2,2,4,4,6,6-hexachlorooctyl group, etc. Haloalkyl groups, preferably C1-6 haloalkyl groups; arylalkyl groups (aralkyl groups) such as benzyl group, phenethyl group, 3-phenylpropyl group, 1-naphthylmethyl group, 2-naphthylmethyl group, preferably C6-10 An aryl C1-6 alkyl group;
　２－ピリジルメチル基、３－ピリジルメチル基、４－ピリジルメチル基、２－（２－ピリジル）エチル基、２－（３－ピリジル）エチル基、２－（４－ピリジル）エチル基、３－（２－ピリジル）プロピル基、３－（３－ピリジル）プロピル基、３－（４－ピリジル）プロピル基、２－ピラジニルメチル基、３－ピラジニルメチル基、２－（２－ピラジニル）エチル基、２－（３－ピラジニル）エチル基、３－（２－ピラジニル）プロピル基、３－（３－ピラジニル）プロピル基、２－ピリミジルメチル基、４－ピリミジルメチル基、２－（２－ピリミジル）エチル基、２－（４－ピリミジル）エチル基、３－（２－ピリミジル）プロピル基、３－（４－ピリミジル）プロピル基、２－フリルメチル基、３－フリルメチル基、２－（２－フリル）エチル基、２－（３－フリル）エチル基、３－（２－フリル）プロピル基、３－（３－フリル）プロピル基などのヘテロアリールアルキル基、好ましくは５～６員ヘテロアリールＣ１～６アルキル基；　ヒドロキシメチル基、１－ヒドロキシエチル基、２―ヒドロキシエチル基、１－ヒドロキシプロピル基、３－ヒドロキシプロピル基、１－ヒドロキシ－１－メチルエチル基、２－ヒドロキシ－１，１－ジメチルエチル基、２－ヒドロキシ－１，１－ジメチルプロピル基、２－ヒドロキシ－２－メチルプロピル基などのヒドロキシアルキル基、好ましくはヒドロキシＣ１～６アルキル基； 2-pyridylmethyl group, 3-pyridylmethyl group, 4-pyridylmethyl group, 2- (2-pyridyl) ethyl group, 2- (3-pyridyl) ethyl group, 2- (4-pyridyl) ethyl group, 3- (2-pyridyl) propyl group, 3- (3-pyridyl) propyl group, 3- (4-pyridyl) propyl group, 2-pyrazinylmethyl group, 3-pyrazinylmethyl group, 2- (2-pyrazinyl) ethyl group, 2- (3-pyrazinyl) ethyl group, 3- (2-pyrazinyl) propyl group, 3- (3-pyrazinyl) propyl group, 2-pyrimidylmethyl group, 4-pyrimidylmethyl group, 2- (2-pyrimidyl) ethyl group, 2- (4-pyrimidyl) ethyl group, 3- (2-pyrimidyl) propyl group, 3- (4-pyrimidyl) propyl group, 2-furylmethyl group, 3-furylmethyl group, 2- (2-furyl E) heteroarylalkyl groups such as ethyl, 2- (3-furyl) ethyl, 3- (2-furyl) propyl, 3- (3-furyl) propyl, preferably 5-6 membered heteroaryl C1 ~ 6 alkyl group; hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy-1-methylethyl group, 2-hydroxy-1,1 A hydroxyalkyl group such as a dimethylethyl group, 2-hydroxy-1,1-dimethylpropyl group, 2-hydroxy-2-methylpropyl group, preferably a hydroxy C1-6 alkyl group;
　メトキシメチル基、エトキシメチル基、２－メトキシエチル基、２－エトキシエチル基、メトキシｎ－プロピル基、ｎ－プロポキシメチル基、ｉ－プロポキシエチル基、ｓ－ブトキシメチル基、ｔ－ブトキシエチル基、２，２－ジメトキシエチル基、２，２－ジメトキシ－１，１－ジメチルエチル基などのアルコキシアルキル基、好ましくはＣ１～６アルコキシＣ１～６アルキル基；　ホルミルオキシメチル基、アセトキシメチル基、２－アセトキシエチル基、プロピオニルオキシメチル基、プロピオニルオキシエチル基などのアシルオキシアルキル基、好ましくはＣ１～７アシルオキシＣ１～６アルキル基；　トリメチルシリルオキシメチル基、ｔ－ブチルジメチルシリルオキシメチル基などのトリアルキルシリルオキシアルキル基、好ましくはトリＣ１～６アルキルシリルオキシＣ１～６アルキル基；　トシルオキシメチル基、２－トシルオキシ－１，１－ジメチルエチル基などのアリールスルホニルオキシアルキル基、好ましくはＣ１～６アルキル置換Ｃ６～１０アリールスルホニルオキシＣ１～６アルキル基；　シアノメチル基、２－シアノエチル基、１－シアノ－１－メチルエチル基などのシアノアルキル基、好ましくはシアノＣ１～６アルキル基；　ホルミルメチル基、２－ホルミルエチル基、３－ホルミルプロピル基、１－ホルミル－１－メチルエチル基、２－ホルミル－１，１－ジメチルエチル基、アセチルメチル基、２－アセチルエチル基、３－アセチルプロピル基、１－アセチル－１－メチルエチル基、２－アセチル－１，１－ジメチルエチル基などのアシルアルキル基、好ましくはＣ１～６アシルＣ１～６アルキル基； Methoxymethyl group, ethoxymethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, methoxy n-propyl group, n-propoxymethyl group, i-propoxyethyl group, s-butoxymethyl group, t-butoxyethyl group, Alkoxyalkyl groups such as 2,2-dimethoxyethyl group, 2,2-dimethoxy-1,1-dimethylethyl group, preferably C1-6 alkoxyC1-6 alkyl groups; formyloxymethyl group, acetoxymethyl group, 2- Acyloxyalkyl groups such as acetoxyethyl group, propionyloxymethyl group, propionyloxyethyl group, preferably C1-7 acyloxy C1-6 alkyl group; trialkylsilyloxy such as trimethylsilyloxymethyl group, t-butyldimethylsilyloxymethyl group Alkyl group, preferred Or a tri-C1-6 alkylsilyloxy C1-6 alkyl group; an arylsulfonyloxyalkyl group such as a tosyloxymethyl group, 2-tosyloxy-1,1-dimethylethyl group, preferably a C1-6 alkyl substituted C6-10 aryl Sulfonyloxy C1-6 alkyl group; cyanoalkyl group such as cyanomethyl group, 2-cyanoethyl group, 1-cyano-1-methylethyl group, preferably cyanoC1-6 alkyl group; formylmethyl group, 2-formylethyl group, 3-formylpropyl group, 1-formyl-1-methylethyl group, 2-formyl-1,1-dimethylethyl group, acetylmethyl group, 2-acetylethyl group, 3-acetylpropyl group, 1-acetyl-1- Such as methylethyl group, 2-acetyl-1,1-dimethylethyl group Alkyl groups, preferably C1 ~ 6 acyl C1 ~ 6 alkyl group;
　２－ヒドロキシイミノエチル基、２－ヒドロキシイミノ－１－メチルエチル基、２－ヒドロキシ－１，１－ジメチルエチル基、２－ヒドロキシイミノプロピル基などの２－ヒドロキシイミノアルキル基、好ましくは２－ヒドロキシイミノＣ２～６アルキル基；　アセチルメチル基、２－アセチルエチル基、３－アセチルプロピル基、１－アセチル－１－メチルエチル基、２－アセチル－１，１－ジメチルエチル基などのアシルアルキル基、好ましくはホルミルＣ１～６アルキル基；　カルボキシメチル基、２－カルボキシエチル基、３－カルボキシプロピル基、１－カルボキシ－１－メチルエチル基、２－カルボキシ－１，１－ジメチルエチル基などのカルボキシアルキル基、好ましくはカルボキシＣ１～６アルキル基；　メトキシカルボニルメチル基、２－メトキシカルボニルエチル基、３－メトキシカルボニルプロピル基、１－メトキシカルボニル－１－メチルエチル基、２－メトキシカルボニル－１，１－ジメチルエチル基などのアルコキシカルボニルアルキル基、好ましくはＣ１～６アルコキシカルボニルＣ１～６アルキル基；　アジドメチル基、２－アジドエチル基、１－アジド－１－メチルエチル基などのアジドアルキル基、好ましくはアジドＣ１～６アルキル基；などが挙げられる。 2-hydroxyiminoalkyl groups such as 2-hydroxyiminoethyl group, 2-hydroxyimino-1-methylethyl group, 2-hydroxy-1,1-dimethylethyl group, 2-hydroxyiminopropyl group, preferably 2-hydroxy An imino C2-6 alkyl group; an acylalkyl group such as an acetylmethyl group, 2-acetylethyl group, 3-acetylpropyl group, 1-acetyl-1-methylethyl group, 2-acetyl-1,1-dimethylethyl group; Preferably formyl C1-6 alkyl group; carboxyalkyl such as carboxymethyl group, 2-carboxyethyl group, 3-carboxypropyl group, 1-carboxy-1-methylethyl group, 2-carboxy-1,1-dimethylethyl group Group, preferably a carboxy C1-6 alkyl group; methoxycarbo An alkoxycarbonylalkyl group such as a rumethyl group, 2-methoxycarbonylethyl group, 3-methoxycarbonylpropyl group, 1-methoxycarbonyl-1-methylethyl group, 2-methoxycarbonyl-1,1-dimethylethyl group, preferably C1 -6 alkoxycarbonyl C1-6 alkyl group; azidoalkyl groups such as azidomethyl group, 2-azidoethyl group, 1-azido-1-methylethyl group, preferably azido C1-6 alkyl group;
　Ｒ1における、「Ｃ２～８アルケニル基」は、少なくとも１つ炭素－炭素二重結合を有する炭素原子２～８個で構成される不飽和炭化水素基である。Ｃ２～８アルケニル基は直鎖であってもよいし、分岐鎖であってもよい。Ｃ２～８アルケニル基としては、ビニル基、１－プロペニル基、イソプロペニル基、アリル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、１－ペンテニル基、２－ペンテニル基、３－ペンテニル基、４－ペンテニル基、１－ヘキセニル基、２－ヘキセニル基、３－ヘキセニル基、４－ヘキセニル基、５－ヘキセニル基、１－ヘプテニル基、６－ヘプテニル基、１－オクテニル基、７－オクテニル基、１－メチル－アリル基、２－メチル－アリル基、１－メチル－２－ブテニル基、２－メチル－２－ブテニル基などが挙げられる。これらのうち、Ｃ２～６アルケニル基が好ましい。
　「置換基を有するＣ２～８アルケニル基」としては、３－クロロ－２－プロペニル基、４－クロロ－２－ブテニル基、４，４－ジクロロ－３－ブテニル基、４，４－ジフルオロ－３－ブテニル基、３，３－ジクロロ－２－プロペニル基、２，３－ジクロロ－２－プロペニル基、３，３－ジフルオロ－２－プロペニル基、２，４，６－トリクロロ－２－ヘキセニル基などのハロアルケニル基、好ましくはＣ２～６ハロアルケニル基；　３－ヒドロキシ－１－プロペニル基、４－ヒドロキシ－１－ブテニル基、１－ヒドロキシアリル基、１－ヒドロキシ－２－メチルアリル基などのヒドロキシアルケニル基、好ましくはヒドロキシＣ２～６アルケニル基；などが挙げられる。 The “C2-8 alkenyl group” in R 1 is an unsaturated hydrocarbon group composed of 2 to 8 carbon atoms having at least one carbon-carbon double bond. The C2-8 alkenyl group may be linear or branched. C2-8 alkenyl groups include vinyl, 1-propenyl, isopropenyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3- Pentenyl group, 4-pentenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 1-heptenyl group, 6-heptenyl group, 1-octenyl group, 7- Examples include octenyl group, 1-methyl-allyl group, 2-methyl-allyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group and the like. Of these, C2-6 alkenyl groups are preferred.
Examples of the “substituted C2-8 alkenyl group” include 3-chloro-2-propenyl group, 4-chloro-2-butenyl group, 4,4-dichloro-3-butenyl group, 4,4-difluoro-3 -Butenyl group, 3,3-dichloro-2-propenyl group, 2,3-dichloro-2-propenyl group, 3,3-difluoro-2-propenyl group, 2,4,6-trichloro-2-hexenyl group, etc. Haloalkenyl groups, preferably C2-6 haloalkenyl groups; hydroxyalkenyl such as 3-hydroxy-1-propenyl, 4-hydroxy-1-butenyl, 1-hydroxyallyl, 1-hydroxy-2-methylallyl Group, preferably a hydroxy C2-6 alkenyl group; and the like.
　Ｒ1における、「Ｃ２～８アルキニル基」は、少なくとも１つ炭素－炭素三重結合を有する炭素原子２～８個で構成される不飽和炭化水素基である。Ｃ２～８アルキニル基は直鎖であってもよいし、分岐鎖であってもよい。Ｃ２～８アルキニル基としては、エチニル基、１－プロピニル基、プロパルギル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、１－ペンチニル基、２－ペンチニル基、３－ペンチニル基、４－ペンチニル基、１－ヘキシニル基、１－メチル－２－プロピニル基、２－メチル－３－ブチニル基、１－メチル－２－ブチニル基、２－メチル－３－ペンチニル基、１，１－ジメチル－２－ブチニル基などが挙げられる。これらのうち、Ｃ２～６アルキニル基が好ましい。
　「置換基を有するＣ２～８アルキニル基」としては、３－クロロ－１－プロピニル基、３－クロロ－１－ブチニル基、３－ブロモ－１－ブチニル基、３－ブロモ－２－プロピニル基、３－ヨード－２－プロピニル基、３－ブロモ－１－ヘキシニル基、４，４，６，６－テトラフルオロ－１－ドデシニル基、５，５－ジクロロ－２－メチル－３－ペンチニル基、４－クロロ－１，１－ジメチル－２－ブチニル基などのハロアルキニル基、好ましくはＣ２～６ハロアルキニル基などが挙げられる。 The “C2-8 alkynyl group” in R 1 is an unsaturated hydrocarbon group composed of 2 to 8 carbon atoms having at least one carbon-carbon triple bond. The C2-8 alkynyl group may be linear or branched. C2-8 alkynyl groups include ethynyl, 1-propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4 -Pentynyl, 1-hexynyl, 1-methyl-2-propynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 2-methyl-3-pentynyl, 1,1-dimethyl And a -2-butynyl group. Of these, C2-6 alkynyl groups are preferred.
Examples of the “substituted C2-8 alkynyl group” include 3-chloro-1-propynyl group, 3-chloro-1-butynyl group, 3-bromo-1-butynyl group, 3-bromo-2-propynyl group, 3-iodo-2-propynyl group, 3-bromo-1-hexynyl group, 4,4,6,6-tetrafluoro-1-dodecynyl group, 5,5-dichloro-2-methyl-3-pentynyl group, 4 A haloalkynyl group such as a -chloro-1,1-dimethyl-2-butynyl group, preferably a C2-6 haloalkynyl group.
　Ｒ1における、「Ｃ３～８シクロアルキル基」は、環状部分を有する炭素原子３～８個で構成されるアルキル基である。Ｃ３～８シクロアルキル基としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基などが挙げられる。これらのうち、Ｃ３～６シクロアルキル基が好ましい。
　「置換基を有するＣ３～８シクロアルキル基」としては、２，３，３－トリメチルシクロブチル基、４，４，６，６－テトラメチルシクロヘキシル基、１，３－ジブチルシクロヘキシル基などのアルキル置換シクロアルキル基、好ましくはＣ１～６アルキル基が１～３個置換したＣ３～６シクロアルキル基などが挙げられる。 The “C3-8 cycloalkyl group” in R 1 is an alkyl group composed of 3 to 8 carbon atoms having a cyclic moiety. Examples of the C3-8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. Of these, C3-6 cycloalkyl groups are preferred.
Examples of the “substituted C3-8 cycloalkyl group” include alkyl substitution such as 2,3,3-trimethylcyclobutyl group, 4,4,6,6-tetramethylcyclohexyl group, 1,3-dibutylcyclohexyl group, etc. Examples thereof include a cycloalkyl group, preferably a C3-6 cycloalkyl group in which 1 to 3 C1-6 alkyl groups are substituted.
　Ｒ1における、「Ｃ４～８シクロアルケニル基」は、環状部分を有する炭素原子４～８個で構成されるアルケニル基である。Ｃ４～８シクロアルケニル基としては、１－シクロブテニル基、１－シクロペンテニル基、３－シクロペンテニル基、１－シクロヘキセニル基、３－シクロヘキセニル基、３－シクロヘプテニル基、４－シクロオクテニル基などが挙げられる。
　「置換基を有するＣ４～８シクロアルケニル基」としては、２－メチル－３－シクロヘキセニル基、３，４－ジメチル－３－シクロヘキセニル基などのアルキル置換シクロアルケニル基、好ましくはＣ１～６アルキル基が１～３個置換したＣ４～６シクロアルケニル基などが挙げられる。 The “C4-8 cycloalkenyl group” in R 1 is an alkenyl group composed of 4 to 8 carbon atoms having a cyclic moiety. Examples of the C4-8 cycloalkenyl group include 1-cyclobutenyl group, 1-cyclopentenyl group, 3-cyclopentenyl group, 1-cyclohexenyl group, 3-cyclohexenyl group, 3-cycloheptenyl group, 4-cyclooctenyl group and the like. It is done.
Examples of the “substituted C4-8 cycloalkenyl group” include alkyl-substituted cycloalkenyl groups such as 2-methyl-3-cyclohexenyl group and 3,4-dimethyl-3-cyclohexenyl group, preferably C1-6 alkyl And C4-6 cycloalkenyl groups substituted with 1 to 3 groups.
　Ｒ1における、「Ｃ６～１０アリール基」は、単環または多環の炭素数６～１０のアリール基である。多環アリール基は、少なくとも一つの環が芳香環であれば、残りの環が飽和脂環、不飽和脂環または芳香環のいずれであってもよい。Ｃ６～１０アリール基としては、フェニル基、ナフチル基、アズレニル基、インデニル基、インダニル基、テトラリニル基などが挙げられる。これらのうち、フェニル基が好ましい。
　「置換基を有するＣ６～１０アリール基」としては、２－クロロフェニル基、３，５－ジクロロフェニル基、４－フルオロフェニル基、３，５－ジフルオロフェニル基、４－トリフルオロメチルフェニル基、２－メトキシ－１－ナフチル基などの、アルキル置換アリール基、ハロゲノ置換アリール基、アルコキシ置換アリール基、好ましくはＣ１～６アルキル置換Ｃ６～１０アリール基、ハロゲノ置換Ｃ６～１０アリール基、Ｃ１～６アルコキシ置換アリール基が挙げられる。 The “C6-10 aryl group” in R 1 is a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms. In the polycyclic aryl group, as long as at least one ring is an aromatic ring, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring. Examples of the C6-10 aryl group include phenyl group, naphthyl group, azulenyl group, indenyl group, indanyl group, tetralinyl group and the like. Of these, a phenyl group is preferred.
Examples of the “substituted C6-10 aryl group” include 2-chlorophenyl group, 3,5-dichlorophenyl group, 4-fluorophenyl group, 3,5-difluorophenyl group, 4-trifluoromethylphenyl group, 2- Alkyl-substituted aryl group, halogeno-substituted aryl group, alkoxy-substituted aryl group such as methoxy-1-naphthyl group, preferably C1-6 alkyl-substituted C6-10 aryl group, halogeno-substituted C6-10 aryl group, C1-6 alkoxy-substituted An aryl group is mentioned.
　Ｒ1における、「ヘテロ環基」は、窒素原子、酸素原子および硫黄原子からなる群から選ばれる１～４個のヘテロ原子を環の構成原子として含む。ヘテロ環基は、単環であってもよいし、多環であってもよい。
　ヘテロ環基としては、５員ヘテロアリール基、６員ヘテロアリール基、縮合ヘテロアリール基、飽和ヘテロ環基、部分不飽和ヘテロ環基などが挙げられる。 The “heterocyclic group” in R 1 includes 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. The heterocyclic group may be monocyclic or polycyclic.
Examples of the heterocyclic group include a 5-membered heteroaryl group, a 6-membered heteroaryl group, a condensed heteroaryl group, a saturated heterocyclic group, and a partially unsaturated heterocyclic group.
　５員ヘテロアリール基としては、　ピロール－１－イル基、ピロール－２－イル基、ピロール－３－イル基などのピロリル基；　フラン－２－イル基、フラン－３－イル基などのフリル基；　チオフェン－２－イル基、チオフェン－３－イル基などのチエニル基；　イミダゾール－１－イル基、イミダゾール－２－イル基、イミダゾール－４－イル基、イミダゾール－５－イル基などのイミダゾリル基；　ピラゾール－１－イル基、ピラゾール－３－イル基、ピラゾール－４－イル基、ピラゾール－５－イル基などのピラゾリル基；オキサゾール－２－イル基、オキサゾール－４－イル基、オキサゾール－５－イル基などのオキサゾリル基；　イソオキサゾール－３－イル基、イソオキサゾール－４－イル基、イソオキサゾール－５－イル基などのイソオキサゾリル基；　チアゾール－２－イル基、チアゾール－４－イル基、チアゾール－５－イル基などのチアゾリル基；　イソチアゾール－３－イル基、イソチアゾール－４－イル基、イソチアゾール－５－イル基などのイソチアゾリル基；　１，２，３－トリアゾール－１－イル基、１，２，３－トリアゾール－４－イル基、１，２，３－トリアゾール－５－イル基、１，２，４－トリアゾール－１－イル基、１，２，４－トリアゾール－３－イル基、１，２，４－トリアゾール－５－イル基などのトリアゾリル基；　１，２，４－オキサジアゾール－３－イル基、１，２，４－オキサジアゾール－５－イル基、１，３，４－オキサジアゾール－２－イル基などのオキサジアゾリル基；　１，２，４－チアジアゾール－３－イル基、１，２，４－チアジアゾール－５－イル基、１，３，４－チアジアゾール－２－イル基などのチアジアゾリル基；　テトラゾール－１－イル基、テトラゾール－２－イル基などのテトラゾリル基；などが挙げられる。 5-membered heteroaryl groups include: pyrrolyl groups such as pyrrol-1-yl, pyrrol-2-yl, and pyrrol-3-yl; furyl groups such as furan-2-yl and furan-3-yl ; Thienyl groups such as thiophen-2-yl group and thiophen-3-yl group; imidazolyl groups such as imidazol-1-yl group, imidazol-2-yl group, imidazol-4-yl group and imidazol-5-yl group A pyrazolyl group such as a pyrazol-1-yl group, a pyrazol-3-yl group, a pyrazol-4-yl group, a pyrazol-5-yl group; an oxazol-2-yl group, an oxazol-4-yl group, an oxazole-5 -Oxazolyl groups such as yl groups; isoxazol-3-yl groups, isoxazol-4-yl groups, isoxazol-5-yl Isoxazolyl groups such as: thiazolyl groups such as thiazol-2-yl group, thiazol-4-yl group, thiazol-5-yl group; isothiazol-3-yl group, isothiazol-4-yl group, isothiazol-5 -An isothiazolyl group such as an yl group; 1,2,3-triazol-1-yl group, 1,2,3-triazol-4-yl group, 1,2,3-triazol-5-yl group, 1,2 , 4-triazol-1-yl group, 1,2,4-triazol-3-yl group, 1,2,4-triazol-5-yl group and the like; 1,2,4-oxadiazole- Oxadiazolyl groups such as 3-yl group, 1,2,4-oxadiazol-5-yl group, 1,3,4-oxadiazol-2-yl group; Groups, thiadiazolyl groups such as 1,2,4-thiadiazol-5-yl group and 1,3,4-thiadiazol-2-yl group; tetrazolyl groups such as tetrazol-1-yl group and tetrazol-2-yl group; Etc.
　６員ヘテロアリール基としては、　ピリジン－２－イル基、ピリジン－３－イル基、ピリジン－４－イル基などのピリジル基；　ピラジン－２－イル基、ピラジン－３－イル基などのピラジニル基；　ピリミジン－２－イル基、ピリミジン－４－イル基、ピリミジン－５－イル基などのピリミジニル基；　ピリダジン－３－イル基、ピリダジン－４－イル基などのピリダジニル基；トリアジニル基；などが挙げられる。 The 6-membered heteroaryl group includes pyridyl groups such as pyridin-2-yl group, pyridin-3-yl group and pyridin-4-yl group; pyrazinyl groups such as pyrazin-2-yl group and pyrazin-3-yl group A pyrimidinyl group such as a pyrimidin-2-yl group, a pyrimidin-4-yl group and a pyrimidin-5-yl group; a pyridazinyl group such as a pyridazin-3-yl group and a pyridazin-4-yl group; a triazinyl group; It is done.
　縮合ヘテロアリール基としては、　インドール－１－イル基、インドール－２－イル基、インドール－３－イル基、インドール－４－イル基、インドール－５－イル基、インドール－６－イル基、インドール－７－イル基；　ベンゾフラン－２－イル基、ベンゾフラン－３－イル基、ベンゾフラン－４－イル基、ベンゾフラン－５－イル基、ベンゾフラン－６－イル基、ベンゾフラン－７－イル基；　ベンゾチオフェン－２－イル基、ベンゾチオフェン－３－イル基、ベンゾチオフェン－４－イル基、ベンゾチオフェン－５－イル基、ベンゾチオフェン－６－イル基、ベンゾチオフェン－７－イル基；　ベンゾイミダゾール－１－イル基、ベンゾイミダゾール－２－イル基、ベンゾイミダゾール－４－イル基、ベンゾイミダゾール－５－イル基、ベンゾオキサゾール－２－イル基、ベンゾオキサゾール－４－イル基、ベンゾオキサゾール－５－イル基、ベンゾチアゾール－２－イル基、ベンゾチアゾール－４－イル基、ベンゾチアゾール－５－イル基；　キノリン－２－イル基、キノリン－３－イル基、キノリン－４－イル基、キノリン－５－イル基、キノリン－６－イル基、キノリン－７－イル基、キノリン－８－イル基；などが挙げられる。 Condensed heteroaryl groups include indol-1-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indol-6-yl, and indole -7-yl group; benzofuran-2-yl group, benzofuran-3-yl group, benzofuran-4-yl group, benzofuran-5-yl group, benzofuran-6-yl group, benzofuran-7-yl group; benzothiophene -2-yl group, benzothiophen-3-yl group, benzothiophen-4-yl group, benzothiophen-5-yl group, benzothiophen-6-yl group, benzothiophen-7-yl group; -Yl group, benzimidazol-2-yl group, benzimidazol-4-yl group, benzimidazol-5-i Group, benzoxazol-2-yl group, benzoxazol-4-yl group, benzoxazol-5-yl group, benzothiazol-2-yl group, benzothiazol-4-yl group, benzothiazol-5-yl group; Quinolin-2-yl group, quinolin-3-yl group, quinolin-4-yl group, quinolin-5-yl group, quinolin-6-yl group, quinolin-7-yl group, quinolin-8-yl group; Is mentioned.
　その他のヘテロ環基としては、　アジリジン－１－イル基、アジリジン－２－イル基、オキシラニル基などの３員飽和へテロ環；　ピロリジン－１－イル基、ピロリジン－２－イル基、ピロリジン－３－イル基、テトラヒドロフラン－２－イル基、テトラヒドロフラン－３－イル基、［１，３］ジオキシラン－２－イル基などの５員飽和へテロ環；　ピペリジン－１－イル基、ピペリジン－２－イル基、ピペリジン－３－イル基、ピペリジン－４－イル基、ピペラジン－１－イル基、ピペラジン－２－イル基、モルホリン－２－イル基、モルホリン－３－イル基、モルホリン－４－イル基などの６員飽和へテロ環；　１，３－ベンゾジオキソール－４－イル基、１，３－ベンゾジオキソール－５－イル基、１，４－ベンゾジオキサン－５－イル基、１，４－ベンゾジオキサン－６－イル基、３，４－ジヒドロ－２Ｈ－１，５－ベンゾジオキセピン－６－イル基、３，４－ジヒドロ－２Ｈ－１，５－ベンゾジオキセピン－７－イル基、２，３－ジヒドロベンゾフラン－４－イル基、２，３－ジヒドロベンゾフラン－５－イル基、２，３－ジヒドロベンゾフラン－６－イル基、２，３－ジヒドロベンゾフラン－７－イル基；などが挙げられる。 Other heterocyclic groups include 3-membered saturated heterocycles such as aziridin-1-yl, aziridin-2-yl, and oxiranyl groups; pyrrolidin-1-yl, pyrrolidin-2-yl, and pyrrolidin-3 -5-membered saturated heterocycle such as -yl group, tetrahydrofuran-2-yl group, tetrahydrofuran-3-yl group, [1,3] dioxiran-2-yl group; piperidin-1-yl group, piperidin-2-yl Group, piperidin-3-yl group, piperidin-4-yl group, piperazin-1-yl group, piperazin-2-yl group, morpholin-2-yl group, morpholin-3-yl group, morpholin-4-yl group 6-membered saturated heterocycle such as 1,3-benzodioxol-4-yl group, 1,3-benzodioxol-5-yl group, 1,4-benzodioxan-5 Group, 1,4-benzodioxan-6-yl group, 3,4-dihydro-2H-1,5-benzodioxepin-6-yl group, 3,4-dihydro-2H-1,5-benzo Dioxepin-7-yl group, 2,3-dihydrobenzofuran-4-yl group, 2,3-dihydrobenzofuran-5-yl group, 2,3-dihydrobenzofuran-6-yl group, 2,3-dihydro A benzofuran-7-yl group;
　「置換基を有するヘテロ環基」としては、４－クロロ－２－ピリジニル基、３－クロロ－２－ピラジニル基、４－メチル－２－ピリジニル基、５－トリフルオロメチル－２－ピリミジニル基、３－メチル－２－キノリル基などが挙げられる。 As the “heterocyclic group having a substituent”, a 4-chloro-2-pyridinyl group, a 3-chloro-2-pyrazinyl group, a 4-methyl-2-pyridinyl group, a 5-trifluoromethyl-2-pyrimidinyl group, Examples include 3-methyl-2-quinolyl group.
　Ｒ1における、「Ｃ１～８アシル基」は、カルボニル基に、水素原子、Ｃ１～７アルキル基、Ｃ２～７アルケニル基、Ｃ２～７アルキニル基、Ｃ６～７アリール基または５～７員ヘテロ環基が結合した基である。
　Ｃ１～８アシル基としては、ホルミル基；　アセチル基、プロピオニル基、ｎ－プロピルカルボニル基、ｎ－ブチルカルボニル基、ペンタノイル基、バレリル基、オクタノイル基、ｉ－プロピルカルボニル基、ｉ－ブチルカルボニル基、ピバロイル基、イソバレリル基などのアルキルカルボニル基、好ましくはＣ１～６アルキルカルボニル基；　アクリロイル基、メタクリロイル基などのアルケニルカルボニル基、好ましくはＣ２～６アルケニルカルボニル基；　プロピオロイル基などのアルキニルカルボニル基、好ましくはＣ２～６アルキニルカルボニル基；　ベンゾイル基などのアリールカルボニル基；２－ピリジルカルボニル基、チエニルカルボニル基などのヘテロ環カルボニル基などが挙げられる。
　「置換基を有するＣ１～８アシル基」としては、モノフルオロアセチル基、モノクロロアセチル基、モノブロモアセチル基、ジフルオロアセチル基、ジクロロアセチル基、ジブロモアセチル基、トリフルオロアセチル基、トリクロロアセチル基、トリブロモアセチル基、３，３，３－トリフルオロプロピオニル基、３，３，３－トリクロロプロピオニル基、２，２，３，３，３－ペンタフルオロプロピオニル基などのハロアシル基、好ましくはＣ１～７ハロアシル基などが挙げられる。 The “C1-8 acyl group” in R 1 is a carbonyl group having a hydrogen atom, a C1-7 alkyl group, a C2-7 alkenyl group, a C2-7 alkynyl group, a C6-7 aryl group or a 5-7 membered heterocyclic ring. A group to which a group is bonded.
C1-8 acyl group includes formyl group; acetyl group, propionyl group, n-propylcarbonyl group, n-butylcarbonyl group, pentanoyl group, valeryl group, octanoyl group, i-propylcarbonyl group, i-butylcarbonyl group, An alkylcarbonyl group such as a pivaloyl group and an isovaleryl group, preferably a C1-6 alkylcarbonyl group; an alkenylcarbonyl group such as an acryloyl group and a methacryloyl group, preferably a C2-6 alkenylcarbonyl group; an alkynylcarbonyl group such as a propioroyl group, preferably C2-6 alkynylcarbonyl groups; arylcarbonyl groups such as benzoyl groups; heterocyclic carbonyl groups such as 2-pyridylcarbonyl groups and thienylcarbonyl groups.
Examples of the “substituted C1-8 acyl group” include a monofluoroacetyl group, a monochloroacetyl group, a monobromoacetyl group, a difluoroacetyl group, a dichloroacetyl group, a dibromoacetyl group, a trifluoroacetyl group, a trichloroacetyl group, a trichloroacetyl group, Haloacyl groups such as bromoacetyl group, 3,3,3-trifluoropropionyl group, 3,3,3-trichloropropionyl group, 2,2,3,3,3-pentafluoropropionyl group, preferably C1-7 haloacyl Groups and the like.
　Ｒ1における、「置換基を有するカルボキシル基」は、カルボニル基に、Ｃ１～６アルキル基、Ｃ２～６アルケニル基、Ｃ２～６アルキニル基、Ｃ６～１０アリール基、Ｃ６～１０アリールＣ１～６アルキル基または５～６員ヘテロ環基が結合した基である。
　「置換基を有するカルボキシル基」としては、メトキシカルボニル基、エトキシカルボニル基、ｎ－プロポキシカルボニル基、ｉ－プロポキシカルボニル基、ｎ－ブトキシカルボニル基、ｉ－ブトキシカルボニル基、ｔ－ブトキシカルボニル基、ｎ－ペンチルオキシカルボニル基、ｎ－ヘキシルオキシカルボニル基などのアルコキシカルボニル基、好ましくはＣ１～６アルコキシカルボニル基；　ビニルオキシカルボニル基、アリルオキシカルボニル基などのアルケニルオキシカルボニル基、好ましくはＣ２～６アルケニルオキシカルボニル基；　エチニルオキシカルボニル基、プロパルギルオキシカルボニル基などのアルキニルオキシカルボニル基、好ましくはＣ２～６アルキニルオキシカルボニル基；　フェノキシカルボニル基、ナフトキシカルボニル基などのアリールオキシカルボニル基、好ましくはＣ６～１０アリールオキシカルボニル基；　ベンジルオキシカルボニル基などのアラルキルオキシカルボニル基、好ましくはＣ６～１０アリールＣ１～６アルコキシカルボニル基；などが挙げられる。 The “carboxyl group having a substituent” in R 1 is a carbonyl group having a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C6-10 aryl group, a C6-10 aryl C1-6 alkyl. Or a group to which a 5- or 6-membered heterocyclic group is bonded.
Examples of the “substituted carboxyl group” include methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, t-butoxycarbonyl group, n An alkoxycarbonyl group such as a pentyloxycarbonyl group or an n-hexyloxycarbonyl group, preferably a C1-6 alkoxycarbonyl group; an alkenyloxycarbonyl group such as a vinyloxycarbonyl group or an allyloxycarbonyl group, preferably a C2-6 alkenyloxy An alkynyloxycarbonyl group such as an ethynyloxycarbonyl group or a propargyloxycarbonyl group, preferably a C2-6 alkynyloxycarbonyl group; a phenoxycarbonyl group, a naphthoxy group Aryloxycarbonyl groups such as carbonyl groups, preferably C6 ~ 10 aryloxycarbonyl group; aralkyloxycarbonyl groups such as benzyloxycarbonyl group, preferably C6 ~ 10 aryl C1 ~ 6 alkoxycarbonyl group; and the like.
　Ｒ1における、「置換基を有するカルバモイル基」は、カルバモイル基に、Ｃ１～６アルキル基、Ｃ２～６アルケニル基、Ｃ２～６アルキニル基、Ｃ６～１０アリール基、Ｃ６～１０アリールＣ１～６アルキル基、または５～６員ヘテロ環基が結合した基である。
　「置換基を有するカルバモイル基」としては、メチルカルバモイル基、エチルカルバモイル基、ジメチルカルバモイル基、ジエチルカルバモイル基などのモノアルキルカルバモイル基またはジアルキルカルバモイル基、好ましくはモノＣ１～６アルキルカルバモイル基またはジＣ１～６アルキルカルバモイル基；　フェニルカルバモイル基、４－メチルフェニルカルバモイル基などのモノアリールカルバモイル基、好ましくはモノＣ６～１０アリールカルバモイル基；などが挙げられる。 The “carbamoyl group having a substituent” in R 1 is a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 6-10 aryl group, a C 6-10 aryl C 1-6 alkyl group. Or a group to which a 5- to 6-membered heterocyclic group is bonded.
As the “carbamoyl group having a substituent”, a monoalkylcarbamoyl group such as a methylcarbamoyl group, an ethylcarbamoyl group, a dimethylcarbamoyl group, a diethylcarbamoyl group or a dialkylcarbamoyl group, preferably a monoC1-6 alkylcarbamoyl group or a diC1˜ 6 alkylcarbamoyl group; monoarylcarbamoyl group such as phenylcarbamoyl group and 4-methylphenylcarbamoyl group, preferably monoC6-10 arylcarbamoyl group.
　Ｒ1における、「置換基を有するスルホニル基」としては、メチルスルホニル基、エチルスルホニル基、ｎ－プロピルスルホニル基、ｉ－プロピルスルホニル基、ｎ－ブチルスルホニル基、ｉ－ブチルスルホニル基、ｓ－ブチルスルホニル基、ｔ－ブチルスルホニル基、ｎ－ペンチルスルホニル基、ｉ－ペンチルスルホニル基、ネオペンチルスルホニル基、１－エチルプロピルスルホニル基、ｎ－ヘキシルスルホニル基、ｉ－ヘキシルスルホニル基などのアルキルスルホニル基、好ましくはＣ１～６アルキルスルホニル基；　トリフルオロメチルスルホニル基などのハロアルキルスルホニル基、好ましくはＣ１～６ハロアルキルスルホニル基；　フェニルスルホニル基、４－メチルフェニルスルホニル基などのアリールスルホニル基、好ましくはＣ６～１０アリールスルホニル基；　スルフォ基；メトキシスルホニル基、エトキシスルホニル基などのアルコキシスルホニル基、好ましくはＣ１～６アルコキシスルホニル基；　スルファモイル基；Ｎ－メチルスルファモイル基、Ｎ－エチルスルファモイル基、Ｎ，Ｎ－ジメチルスルファモイル基、Ｎ，Ｎ－ジエチルスルファモイル基などのスルファモイル基、好ましくはモノＣ１～６アルキルスルファモイル基またはジＣ１～６アルキルスルファモイル基；　フェニルスルファモイル基、４－メチルフェニルスルファモイル基などのモノアリールスルファモイル基、好ましくはモノＣ６～１０アリールスルファモイル基；などが挙げられる。 Examples of the “sulfonyl group having a substituent” in R 1 include a methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, i-propylsulfonyl group, n-butylsulfonyl group, i-butylsulfonyl group, s-butyl. Alkylsulfonyl groups such as sulfonyl group, t-butylsulfonyl group, n-pentylsulfonyl group, i-pentylsulfonyl group, neopentylsulfonyl group, 1-ethylpropylsulfonyl group, n-hexylsulfonyl group, i-hexylsulfonyl group, Preferably a C1-6 alkylsulfonyl group; a haloalkylsulfonyl group such as a trifluoromethylsulfonyl group, preferably a C1-6 haloalkylsulfonyl group; an arylsulfonyl group such as a phenylsulfonyl group, a 4-methylphenylsulfonyl group, preferably C6-10 arylsulfonyl group; sulfo group; alkoxysulfonyl group such as methoxysulfonyl group and ethoxysulfonyl group, preferably C1-6 alkoxysulfonyl group; sulfamoyl group; N-methylsulfamoyl group, N-ethylsulfamoyl group A sulfamoyl group such as N, N-dimethylsulfamoyl group, N, N-diethylsulfamoyl group, preferably a mono C1-6 alkylsulfamoyl group or a diC1-6 alkylsulfamoyl group; And a monoarylsulfamoyl group such as a moyl group and 4-methylphenylsulfamoyl group, preferably a mono C6-10 arylsulfamoyl group.
　「置換基を有するアミノ基」としては、メチルアミノ基、エチルアミノ基、ｎ－プロピルアミノ基、ｎ－ブチルアミノ基、ジメチルアミノ基、ジエチルアミノ基などのアルキルアミノ基、好ましくはモノＣ１～６アルキルアミノ基またはジＣ１～６アルキルアミノ基；　メチリデンアミノ基、エチリデンアミノ基などのモノＣ１～６アルキリデンアミノ基；　フェニルアミノ基、４－メチルフェニルアミノ基などのモノアリールアミノ基、好ましくはモノＣ６～１０アリールアミノ基；　ジ１－ナフチルアミノ基などのジアリールアミノ基、好ましくはジＣ６～１０アリールアミノ基；　ベンジルアミノ基などのアラルキルアミノ基、好ましくはＣ６～１０アリールＣ１～６アルキルアミノ基；　アセチルアミノ基、トリフルオロアセチルアミノ基、ベンゾイルアミノ基などのアシルアミノ基、好ましくはＣ１～６アシルアミノ基；　メトキシカルボニルアミノ基、ｔ－ブトキシカルボニルアミノ基などのアルコキシカルボニルアミノ基、好ましくはＣ１～６アルコキシカルボニルアミノ基；などが挙げられる。 As the “amino group having a substituent”, an alkylamino group such as a methylamino group, an ethylamino group, an n-propylamino group, an n-butylamino group, a dimethylamino group or a diethylamino group, preferably a mono-C1-6 alkyl Amino group or di-C1-6 alkylamino group; mono-C1-6 alkylideneamino group such as methylideneamino group, ethylideneamino group; monoarylamino group such as phenylamino group, 4-methylphenylamino group, preferably monoC6-10 Arylamino group; diarylamino group such as di1-naphthylamino group, preferably diC6-10 arylamino group; aralkylamino group such as benzylamino group, preferably C6-10 arylC1-6 alkylamino group; acetylamino Group, trifluoroacetyl An acylamino group such as a mino group or a benzoylamino group, preferably a C1-6 acylamino group; an alkoxycarbonylamino group such as a methoxycarbonylamino group or a t-butoxycarbonylamino group, preferably a C1-6 alkoxycarbonylamino group; It is done.
〔Ｒ2〕
　Ｒ2は、水素原子、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、置換基を有するスルホニル基、無置換の若しくは置換基を有する水酸基、または無置換の若しくは置換基を有するアミノ基を示す。 [R 2 ]
R 2 represents a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, A substituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted group; Having a heterocyclic group, an unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted carboxyl group, an unsubstituted or substituted carbamoyl group, a substituted sulfonyl group, unsubstituted Or a hydroxyl group having a substituent, or an amino group having no substituent or a substituent.
　Ｒ2における、「Ｃ１～８アルキル基」、「Ｃ２～８アルケニル基」、「Ｃ２～８アルキニル基」、「Ｃ３～８シクロアルキル基」、「Ｃ４～８シクロアルケニル基」、「Ｃ６～１０アリール基」、「ヘテロ環基」、「Ｃ１～８アシル基」、「置換基を有するカルボキシル基」、「置換基を有するカルバモイル基」、「置換基を有するスルホニル基」、「置換基を有するアミノ基」は、Ｒ1で例示したものと同じものが挙げられる。 In R 2 , “C1-8 alkyl group”, “C2-8 alkenyl group”, “C2-8 alkynyl group”, “C3-8 cycloalkyl group”, “C4-8 cycloalkenyl group”, “C6-10” “Aryl group”, “heterocyclic group”, “C1-8 acyl group”, “carboxyl group having substituent”, “carbamoyl group having substituent”, “sulfonyl group having substituent”, “having substituent” Examples of the “amino group” are the same as those exemplified for R 1 .
　Ｒ2における、「置換基を有する水酸基」としては、メトキシ基、エトキシ基、ｎ－プロポキシ基、ｎ－ブトキシ基、ｎ－ペンチルオキシ基、ｎ－ヘキシルオキシ基、デシルオキシ基、ドデシルオキシ基、ラウリルオキシ基、ｉ－プロポキシ基、ｉ－ブトキシ基、ｓ－ブトキシ基、ｔ－ブトキシ基、１－エチルプロポキシ基、ｉ－ヘキシルオキシ基、４－メチルペントキシ基、３－メチルペントキシ基、２－メチルペントキシ基、１－メチルペントキシ基、３，３－ジメチルブトキシ基、２，２－ジメチルブトキシ基、１，１－ジメチルブトキシ基、１，２－ジメチルブトキシ基、１，３－ジメチルブトキシ基、２，３－ジメチルブトキシ基、１－エチルブトキシ基、２－エチルブトキシ基などのアルコキシ基、好ましくはＣ１～６アルコキシ基； The “hydroxyl group having a substituent” in R 2 includes a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, a decyloxy group, a dodecyloxy group, and lauryl. Oxy group, i-propoxy group, i-butoxy group, s-butoxy group, t-butoxy group, 1-ethylpropoxy group, i-hexyloxy group, 4-methylpentoxy group, 3-methylpentoxy group, 2 -Methylpentoxy group, 1-methylpentoxy group, 3,3-dimethylbutoxy group, 2,2-dimethylbutoxy group, 1,1-dimethylbutoxy group, 1,2-dimethylbutoxy group, 1,3-dimethyl Alkoxy groups such as butoxy group, 2,3-dimethylbutoxy group, 1-ethylbutoxy group, 2-ethylbutoxy group, preferably C1-6 alkoxy Group;
　シクロプロピルメチルオキシ基、２－シクロペンチルエチルオキシ基などのシクロアルキルアルコキシ基、好ましくはＣ３～８シクロアルキルＣ１～６アルコキシ基；　ベンジルオキシ基などのアラルキルオキシ基、好ましくはＣ６～１０アリールＣ１～６アルコキシ基；　クロロメトキシ基、ジクロロメトキシ基、トリクロロメトキシ基、トリフルオロメトキシ基、１－フルオロエトキシ基、１，１－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、ペンタフルオロエトキシ基などのハロアルコキシ基、好ましくはＣ１～６ハロアルコキシ基；　ビニルオキシ基、１－プロペニルオキシ基、アリルオキシ基、１－ブテニルオキシ基、２－ブテニルオキシ基、３－ブテニルオキシ基、１－ペンテニルオキシ基、２－ペンテニルオキシ基、３－ペンテニルオキシ基、４－ペンテニルオキシ基、１－ヘキセニルオキシ基、２－ヘキセニルオキシ基、３－ヘキセニルオキシ基、４－ヘキセニルオキシ基、５－ヘキセニルオキシ基、１－メチル－２－プロペニルオキシ基、２－メチル－２－プロペニルオキシ基、１－メチル－２－ブテニルオキシ基、２－メチル－２－ブテニルオキシ基などのアルケニルオキシ基、好ましくはＣ２～６アルケニルオキシ基； A cycloalkylalkoxy group such as a cyclopropylmethyloxy group and a 2-cyclopentylethyloxy group, preferably a C3-8 cycloalkyl C1-6 alkoxy group; an aralkyloxy group such as a benzyloxy group, preferably a C6-10 aryl C1-6 Alkoxy group; chloromethoxy group, dichloromethoxy group, trichloromethoxy group, trifluoromethoxy group, 1-fluoroethoxy group, 1,1-difluoroethoxy group, 2,2,2-trifluoroethoxy group, pentafluoroethoxy group, etc. A haloalkoxy group, preferably a C1-6 haloalkoxy group; vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1-pentenyloxy group, 2-pentenyl group Oxy group, 3-pentenyloxy group, 4-pentenyloxy group, 1-hexenyloxy group, 2-hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group, 1-methyl-2 An alkenyloxy group such as a propenyloxy group, a 2-methyl-2-propenyloxy group, a 1-methyl-2-butenyloxy group, or a 2-methyl-2-butenyloxy group, preferably a C2-6 alkenyloxy group;
　エチニルオキシ基、プロピニルオキシ基、プロパルギルオキシ基、１－ブチニルオキシ基、２－ブチニルオキシ基、３－ブチニルオキシ基、１－ペンチニルオキシ基、２－ペンチニルオキシ基、３－ペンチニルオキシ基、４－ペンチニルオキシ基、１－ヘキシニルオキシ基、１－メチル－２－プロピニルオキシ基、２－メチル－３－ブチニルオキシ基、１－メチル－２－ブチニルオキシ基、２－メチル－３－ペンチニルオキシ基、１，１－ジメチル－２－ブチニルオキシ基などのアルキニルオキシ基、好ましくはＣ２～６アルキニルオキシ基；　シクロプロピルオキシ基、シクロブチルオキシ基、シクロペンチルオキシ基、シクロヘキシルオキシ基、シクロヘプチルオキシ基、シクロオクチルオキシ基、２－メチルシクロプロピルオキシ基、２－エチルシクロプロピルオキシ基、２，３，３－トリメチルシクロブチルオキシ基、２－メチルシクロペンチルオキシ基、２－エチルシクロヘキシルオキシ基、２－エチルシクロオクチルオキシ基、４，４，６，６－テトラメチルシクロヘキシルオキシ基、１，３－ジブチルシクロヘキシルオキシ基などのシクロアルキルオキシ基、好ましくはＣ３～６シクロアルキルオキシ基；　フェニルオキシ基、ナフチルオキシ基、アズレニルオキシ基、インデニルオキシ基、インダニルオキシ基、テトラリニルオキシ基などのアリールオキシ基、好ましくはＣ６～１０アリールオキシ基；　ベンジルオキシ基、フェネチルオキシ基、２－ナフチルメチルオキシ基などのアリールアルキルオキシ基（アラルキルオキシ基）、好ましくはＣ６～１０アリールＣ１～６アルキルオキシ基；　アセチルオキシ基、プロピオニルオキシ基、ｎ－プロピルカルボニルオキシ基、ｉ－プロピルカルボニルオキシ基、ｎ－ブチルカルボニルオキシ基、ｉ－ブチルカルボニルオキシ基、ペンタノイルオキシ基、ピバロイルオキシ基などのアシルオキシ基、好ましくはＣ１～７アシルオキシ基；　メトキシカルボニルメチルオキシ基、１－メトキシカルボニル－１－メチルエチルオキシ基などのアルコキシカルボニルアルキルオキシ基、好ましくはＣ１～６アルコキシカルボニルＣ１～６アルコキシ基；　トリメチルシリルオキシ基、ｔ－ブチルジメチルシリルオキシ基などのトリアルキルシリルオキシ基、好ましくはトリＣ１～６アルキルシリルオキシ基；
などが挙げられる。 Ethynyloxy group, propynyloxy group, propargyloxy group, 1-butynyloxy group, 2-butynyloxy group, 3-butynyloxy group, 1-pentynyloxy group, 2-pentynyloxy group, 3-pentynyloxy group, 4- Pentynyloxy group, 1-hexynyloxy group, 1-methyl-2-propynyloxy group, 2-methyl-3-butynyloxy group, 1-methyl-2-butynyloxy group, 2-methyl-3-pentynyloxy group, 1 , 1-dimethyl-2-butynyloxy group, preferably C2-6 alkynyloxy group; cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group Group, 2-methylcyclopropyloxy group, 2 -Ethylcyclopropyloxy group, 2,3,3-trimethylcyclobutyloxy group, 2-methylcyclopentyloxy group, 2-ethylcyclohexyloxy group, 2-ethylcyclooctyloxy group, 4,4,6,6-tetra A cycloalkyloxy group such as a methylcyclohexyloxy group or a 1,3-dibutylcyclohexyloxy group, preferably a C3-6 cycloalkyloxy group; a phenyloxy group, a naphthyloxy group, an azulenyloxy group, an indenyloxy group, an indanyloxy group; Aryloxy groups such as tetralinyloxy groups, preferably C6-10 aryloxy groups; arylalkyloxy groups (aralkyloxy groups) such as benzyloxy groups, phenethyloxy groups, 2-naphthylmethyloxy groups, preferably C6 ~ 10 aryl 1-6 alkyloxy groups; acetyloxy group, propionyloxy group, n-propylcarbonyloxy group, i-propylcarbonyloxy group, n-butylcarbonyloxy group, i-butylcarbonyloxy group, pentanoyloxy group, pivaloyloxy group An acyloxy group such as, preferably a C1-7 acyloxy group; an alkoxycarbonylalkyloxy group such as a methoxycarbonylmethyloxy group, 1-methoxycarbonyl-1-methylethyloxy group, preferably a C1-6 alkoxycarbonyl C1-6 alkoxy group A trialkylsilyloxy group such as a trimethylsilyloxy group or t-butyldimethylsilyloxy group, preferably a tri-C1-6 alkylsilyloxy group;
Etc.
〔Ｒ3〕
　Ｒ3は、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有するメルカプト基、無置換の若しくは置換基を有する水酸基、または無置換の若しくは置換基を有するアミノ基を示す。 [R 3 ]
R 3 is an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, unsubstituted or A substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted heterocycle A group, an unsubstituted or substituted mercapto group, an unsubstituted or substituted hydroxyl group, or an unsubstituted or substituted amino group.
　Ｒ3における、「Ｃ１～８アルキル基」、「Ｃ２～８アルケニル基」、「Ｃ２～８アルキニル基」、「Ｃ３～８シクロアルキル基」、「Ｃ４～８シクロアルケニル基」、「Ｃ６～１０アリール基」、「ヘテロ環基」、「置換基を有するアミノ基」は、Ｒ1で例示したものと同じものが挙げられる。Ｒ3における、「置換基を有する水酸基」は、Ｒ2で例示したものと同じものが挙げられる。 In R 3 , “C1-8 alkyl group”, “C2-8 alkenyl group”, “C2-8 alkynyl group”, “C3-8 cycloalkyl group”, “C4-8 cycloalkenyl group”, “C6-10” Examples of the “aryl group”, “heterocyclic group” and “amino group having a substituent” are the same as those exemplified for R 1 . Examples of the “hydroxyl group having a substituent” in R 3 are the same as those exemplified for R 2 .
　Ｒ3における、「置換基を有するメルカプト基」としては、メチルチオ基、エチルチオ基などのアルキルチオ基、好ましくはＣ１～６アルキルチオ基；　フェニルチオ基、４－メチルフェニルチオ基などのアリールチオ基、好ましくはＣ６～１０アリールチオ基；　アセチルチオ基、ベンゾイルチオ基などのアシルチオ基、好ましくはＣ１～６アシルチオ基；などが挙げられる。 As the “mercapto group having a substituent” in R 3 , an alkylthio group such as a methylthio group and an ethylthio group, preferably a C1-6 alkylthio group; an arylthio group such as a phenylthio group and a 4-methylphenylthio group, preferably C6 To 10 arylthio groups; acylthio groups such as acetylthio group and benzoylthio group, preferably C1 to 6 acylthio groups;
〔Ｒ4〕
　Ｒ4は、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、または無置換の若しくは置換基を有するヘテロ環基を示す。 [R 4 ]
R 4 is an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, unsubstituted or A substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted hetero A ring group is shown.
　Ｒ4における、「Ｃ１～８アルキル基」、「Ｃ２～８アルケニル基」、「Ｃ２～８アルキニル基」、「Ｃ３～８シクロアルキル基」、「Ｃ４～８シクロアルケニル基」、「Ｃ６～１０アリール基」、「ヘテロ環基」は、Ｒ1で例示したものと同じものが挙げられる。 In R 4 , “C1-8 alkyl group”, “C2-8 alkenyl group”, “C2-8 alkynyl group”, “C3-8 cycloalkyl group”, “C4-8 cycloalkenyl group”, “C6-10” Examples of the “aryl group” and “heterocyclic group” are the same as those exemplified for R 1 .
〔Ｒ5〕
　Ｒ5は、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、または無置換の若しくは置換基を有するヘテロ環基を示す。 [R 5]
R 5 is an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, unsubstituted or A substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted hetero A ring group is shown.
　Ｒ5における、「Ｃ１～８アルキル基」、「Ｃ２～８アルケニル基」、「Ｃ２～８アルキニル基」、「Ｃ３～８シクロアルキル基」、「Ｃ４～８シクロアルケニル基」、「Ｃ６～１０アリール基」、「ヘテロ環基」は、Ｒ1で例示したものと同じものが挙げられる。 In R 5 , “C1-8 alkyl group”, “C2-8 alkenyl group”, “C2-8 alkynyl group”, “C3-8 cycloalkyl group”, “C4-8 cycloalkenyl group”, “C6-10” Examples of the “aryl group” and “heterocyclic group” are the same as those exemplified for R 1 .
　ＮＲ1Ｒ2で表される基において、Ｒ1とＲ2は一緒になって、無置換の若しくは置換基を有する３～８員環を形成してもよいし、または＝ＣＲaＲb若しくは＝Ｎ－Ｒcを形成してもよい。前記３～８員環としては、アジリジン環、ピロリジン環、ピペリジン環、ピペラジン環、モルホリン環などの飽和ヘテロ環を挙げることができる。 In the group represented by NR 1 R 2 , R 1 and R 2 may be combined to form an unsubstituted or substituted 3- to 8-membered ring, or ═CR a R b or ═N—R c may be formed. Examples of the 3- to 8-membered ring include saturated heterocycles such as an aziridine ring, a pyrrolidine ring, a piperidine ring, a piperazine ring, and a morpholine ring.
　ＲaおよびＲbは、それぞれ独立に、水素原子、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、置換基を有するスルホニル基、無置換の若しくは置換基を有するメルカプト基、無置換の若しくは置換基を有する水酸基、または無置換の若しくは置換基を有するアミノ基を示す。 R a and R b each independently have a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted group A C2-8 alkynyl group, an unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, Unsubstituted or substituted heterocyclic group, unsubstituted or substituted C1-8 acyl group, unsubstituted or substituted carboxyl group, unsubstituted or substituted carbamoyl group, substituted group A sulfonyl group having, an unsubstituted or substituted mercapto group, an unsubstituted or substituted hydroxyl group, or unsubstituted Or an amino group having a substituent.
　ＲaおよびＲbにおける、「Ｃ１～８アルキル基」、「Ｃ２～８アルケニル基」、「Ｃ２～８アルキニル基」、「Ｃ３～８シクロアルキル基」、「Ｃ４～８シクロアルケニル基」、「Ｃ６～１０アリール基」、「ヘテロ環基」、「Ｃ１～８アシル基」、「置換基を有するカルボキシル基」、「置換基を有するカルバモイル基」、「置換基を有するスルホニル基」、「置換基を有するアミノ基」は、Ｒ1で例示したものと同じものが挙げられる。ＲaおよびＲbにおける、「置換基を有する水酸基」は、Ｒ2で例示したものと同じものが挙げられる。ＲaおよびＲbにおける、「置換基を有するメルカプト基」は、Ｒ3で例示したものと同じものが挙げられる。 In R a and R b , “C1-8 alkyl group”, “C2-8 alkenyl group”, “C2-8 alkynyl group”, “C3-8 cycloalkyl group”, “C4-8 cycloalkenyl group”, “ “C6-10 aryl group”, “heterocyclic group”, “C1-8 acyl group”, “carboxyl group having substituent”, “carbamoyl group having substituent”, “sulfonyl group having substituent”, “substituted” Examples of the “amino group having a group” are the same as those exemplified for R 1 . Examples of the “hydroxyl group having a substituent” in R a and R b are the same as those exemplified for R 2 . Examples of the “mercapto group having a substituent” in R a and R b are the same as those exemplified for R 3 .
　Ｒcは、無置換の若しくは置換基を有する水酸基、または無置換の若しくは置換基を有するＣ１～８アルキル基を示す。
　Ｒcにおける、「Ｃ１～８アルキル基」は、Ｒ1で例示したものと同じものが挙げられる。Ｒcにおける、「置換基を有する水酸基」は、Ｒ2で例示したものと同じものが挙げられる。 R c represents an unsubstituted or substituted hydroxyl group, or an unsubstituted or substituted C1-8 alkyl group.
Examples of the “C1-8 alkyl group” in R c are the same as those exemplified for R 1 . Examples of the “hydroxyl group having a substituent” in R c include the same groups as those exemplified for R 2 .
　Ｎ＝Ｓ(＝Ｏ)Ｒ4Ｒ5で表される基において、Ｒ4とＲ5は一緒になって、無置換の若しくは置換基を有する５～８員環を形成してもよい。前記５～８員環としては、テトラヒドロチオフェン環、テトラヒドロチオピラン環、［１．４］オキサチアン環などの含硫黄飽和ヘテロ環を挙げることができる。 In the group represented by N═S (═O) R 4 R 5 , R 4 and R 5 may be combined to form an unsubstituted or substituted 5- to 8-membered ring. Examples of the 5- to 8-membered ring include sulfur-containing saturated hetero rings such as a tetrahydrothiophene ring, a tetrahydrothiopyran ring, and a [1.4] oxathian ring.
〔Ｘ1、ｍ〕
　Ｘ1は、それぞれ独立に、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有する（１－イミノ）Ｃ１～８アルキル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、無置換の若しくは置換基を有する水酸基、無置換の若しくは置換基を有するアミノ基、無置換の若しくは置換基を有するメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、またはニトロ基を示す。
　ｍは、Ｘ1の個数を示し且つ０～５のいずれかの整数である。 [X 1, m]
X 1 is each independently an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, Unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C4-8 cycloalkenyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted An unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted (1-imino) C1-8 alkyl group, an unsubstituted or substituted carboxyl group, Unsubstituted or substituted carbamoyl group, unsubstituted or substituted hydroxyl group, unsubstituted or substituted amino group Mercapto group with an unsubstituted or substituted group, a sulfonyl group having a substituent, a halogeno group, a cyano group or a nitro group.
m represents the number of X 1 and is an integer from 0 to 5.
　Ｘ1における、「Ｃ１～８アルキル基」、「Ｃ２～８アルケニル基」、「Ｃ２～８アルキニル基」、「Ｃ３～８シクロアルキル基」、「Ｃ４～８シクロアルケニル基」、「Ｃ６～１０アリール基」、「ヘテロ環基」、「Ｃ１～８アシル基」、「置換基を有するカルボキシル基」、「置換基を有するカルバモイル基」、「置換基を有するスルホニル基」、「置換基を有するアミノ基」は、Ｒ1で例示したものと同じものが挙げられる。Ｘ1における、「置換基を有する水酸基」は、Ｒ2で例示したものと同じものが挙げられる。Ｘ1における、「置換基を有するメルカプト基」は、Ｒ3で例示したものと同じものが挙げられる。 “C1-8 alkyl group”, “C2-8 alkenyl group”, “C2-8 alkynyl group”, “C3-8 cycloalkyl group”, “C4-8 cycloalkenyl group”, “C6-10” in X 1 “Aryl group”, “heterocyclic group”, “C1-8 acyl group”, “carboxyl group having substituent”, “carbamoyl group having substituent”, “sulfonyl group having substituent”, “having substituent” Examples of the “amino group” include the same as those exemplified for R 1 . Examples of the “hydroxyl group having a substituent” in X 1 include the same as those exemplified for R 2 . Examples of the “substituent mercapto group” in X 1 include the same as those exemplified for R 3 .
　Ｘ1における、「（１－イミノ）Ｃ１～８アルキル基」は、イミノメチル基、若しくはイミノメチル基にＣ１～７のアルキル基が結合した基である。（１－イミノ）Ｃ１～８アルキル基としては、イミノメチル基、（１－イミノ）エチル基、（１－イミノ）プロピル基、（１－イミノ）ブチル基、（１－イミノ）ペンチル基、（１－イミノ）ヘキシル基、（１－イミノ）ヘプチル基などが挙げられる。これらのうち、（１－イミノ）Ｃ１～６アルキル基が好ましい。
　「置換基を有する（１－イミノ）Ｃ１～８アルキル基」としては、ヒドロキシイミノメチル基、（１－ヒドロキシイミノ）エチル基、（１－ヒドロキシイミノ）プロピル基、（１－ヒドロキシイミノ）ブチル基などの（１－ヒドロキシイミノ）アルキル基、好ましくは（１－ヒドロキシイミノ）Ｃ１～６アルキル基；メトキシイミノメチル基、（１－エトキシイミノ）メチル基、（１－メトキシイミノ）エチル基、（１－ｔ－ブトキシイミノ）エチル基、（１－エトキシイミノ）エチル基などの（１－アルコキシイミノ）アルキル基、好ましくは（１－（Ｃ１～６アルコキシ）イミノ）Ｃ１～６アルキル基；などが挙げられる。 The “(1-imino) C1-8 alkyl group” in X 1 is an iminomethyl group or a group in which a C1-7 alkyl group is bonded to an iminomethyl group. The (1-imino) C1-8 alkyl group includes an iminomethyl group, a (1-imino) ethyl group, a (1-imino) propyl group, a (1-imino) butyl group, a (1-imino) pentyl group, (1 -Imino) hexyl group, (1-imino) heptyl group and the like. Of these, (1-imino) C1-6 alkyl groups are preferred.
The “(1-imino) C1-8 alkyl group having a substituent” includes a hydroxyiminomethyl group, a (1-hydroxyimino) ethyl group, a (1-hydroxyimino) propyl group, and a (1-hydroxyimino) butyl group. (1-hydroxyimino) alkyl group such as, preferably (1-hydroxyimino) C1-6 alkyl group; methoxyiminomethyl group, (1-ethoxyimino) methyl group, (1-methoxyimino) ethyl group, (1 A (1-alkoxyimino) alkyl group such as a -t-butoxyimino) ethyl group or a (1-ethoxyimino) ethyl group, preferably a (1- (C1-6 alkoxy) imino) C1-6 alkyl group; It is done.
　Ｘ1における、「ハロゲノ基」としては、フルオロ基、クロロ基、ブロモ基、ヨード基などが挙げられる。 Examples of the “halogeno group” in X 1 include a fluoro group, a chloro group, a bromo group, and an iodo group.
〔Ｂ、Ｄ〕
　Ｂは、炭素原子または窒素原子を示す。すなわち、「Ｄ」が縮合したピリジン環または「Ｄ」が縮合したピラジン環を構成する。
　Ｄは、無置換の若しくはＸ1で置換された５～７員炭化水素環、または無置換の若しくはＸ1で置換された５～７員ヘテロ環を示す。
　５～７員炭化水素環としては、ベンゼン環などの芳香族炭化水素環；　シクロペンテン環、シクロヘキセン環、シクロヘプテン環などのＣ５～７シクロアルケン環；　フラン環、チオフェン環、ピロ－ル環、イミダゾール環、ピラゾール環、チアゾール環、オキサゾール環、イソオキサゾール環、ピリジン環、ピラジン環、ピリミジン環、ピリダジン環、アゼピン環、ジアゼピン環などの芳香族５～７員ヘテロ環；　ジヒドロ－２Ｈ－ピラン環、ジヒドロ－２Ｈ－チオピラン環、テトラヒドロピリジン環などの不飽和５～７員ヘテロ環；などが挙げられる。
　これらのうち芳香族炭化水素環が好ましく、ベンゼン環がより好ましい。具体的には、本発明に係る化合物は、キノリン環もしくはキノキサリン環を有する化合物であることが好ましい。 [B, D]
B represents a carbon atom or a nitrogen atom. That is, a pyridine ring condensed with “D” or a pyrazine ring condensed with “D” is formed.
D represents a 5- to 7-membered heterocycle substituted with been 5-7 membered hydrocarbon ring or an unsubstituted or X 1, substituted by unsubstituted or X 1.
The 5- to 7-membered hydrocarbon ring includes an aromatic hydrocarbon ring such as a benzene ring; a C5-7 cycloalkene ring such as a cyclopentene ring, cyclohexene ring, and cycloheptene ring; a furan ring, a thiophene ring, a pyrrole ring, and an imidazole ring. , Pyrazole ring, thiazole ring, oxazole ring, isoxazole ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, azepine ring, diazepine ring and other aromatic 5- to 7-membered heterocycles; dihydro-2H-pyran ring, dihydro -2H-thiopyran ring, unsaturated 5- to 7-membered heterocycle such as tetrahydropyridine ring; and the like.
Of these, an aromatic hydrocarbon ring is preferable, and a benzene ring is more preferable. Specifically, the compound according to the present invention is preferably a compound having a quinoline ring or a quinoxaline ring.
〔Ｘ2、ｎ〕
　Ｘ2は、それぞれ独立に、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有する（１－イミノ）Ｃ１～８アルキル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、無置換の若しくは置換基を有する水酸基、無置換の若しくは置換基を有するアミノ基、無置換の若しくは置換基を有するメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、またはニトロ基を示す。
　ｎは、Ｘ2の個数を示し且つ０～３のいずれかの整数である。 [X 2, n]
X 2 each independently represents an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, Unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C4-8 cycloalkenyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted An unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted (1-imino) C1-8 alkyl group, an unsubstituted or substituted carboxyl group, Unsubstituted or substituted carbamoyl group, unsubstituted or substituted hydroxyl group, unsubstituted or substituted amino group Mercapto group with an unsubstituted or substituted group, a sulfonyl group having a substituent, a halogeno group, a cyano group or a nitro group.
n represents the number of X 2 and is an integer from 0 to 3.
　Ｘ2における、「Ｃ１～８アルキル基」、「Ｃ２～８アルケニル基」、「Ｃ２～８アルキニル基」、「Ｃ３～８シクロアルキル基」、「Ｃ４～８シクロアルケニル基」、「Ｃ６～１０アリール基」、「ヘテロ環基」、「Ｃ１～８アシル基」、「置換基を有するカルボキシル基」、「置換基を有するカルバモイル基」、「置換基を有するスルホニル基」、「置換基を有するアミノ基」は、Ｒ1で例示したものと同じものが挙げられる。Ｘ2における、「置換基を有する水酸基」は、Ｒ2で例示したものと同じものが挙げられる。Ｘ2における、「置換基を有するメルカプト基」は、Ｒ3で例示したものと同じものが挙げられる。Ｘ2における、「（１－イミノ）Ｃ１～８アルキル基」、「ハロゲノ基」は、Ｘ1で例示したものと同じものが挙げられる。 “C1-8 alkyl group”, “C2-8 alkenyl group”, “C2-8 alkynyl group”, “C3-8 cycloalkyl group”, “C4-8 cycloalkenyl group”, “C6-10” in X 2 “Aryl group”, “heterocyclic group”, “C1-8 acyl group”, “carboxyl group having substituent”, “carbamoyl group having substituent”, “sulfonyl group having substituent”, “having substituent” Examples of the “amino group” are the same as those exemplified for R 1 . Examples of the “hydroxyl group having a substituent” in X 2 include the same as those exemplified for R 2 . Examples of the “mercapto group having a substituent” in X 2 include the same as those exemplified for R 3 . In X 2, "(1-imino) C1 ~ 8 alkyl group", "halogeno group" may be the same as those exemplified for X 1.
　Ｘ2のいずれかひとつと、Ｒとが一緒になって、無置換の若しくは置換基を有する５～８員環を形成してもよい。 Any one of X 2 and R may be combined with each other to form an unsubstituted or substituted 5- to 8-membered ring.
〔Ｅ〕
　Ｅは、無置換の若しくはＸ２で置換された５～７員炭化水素環、または無置換の若しくはＸ２で置換された５～７員ヘテロ環を示す。
　５～７員炭化水素環としては、ベンゼン環などの芳香族炭化水素環；　シクロペンテン環、シクロヘキセン環、シクロヘプテン環などのＣ５～７シクロアルケン環；　フラン環、チオフェン環、ピロ－ル環、イミダゾール環、ピラゾール環、チアゾール環、オキサゾール環、イソオキサゾール環、イソチアゾール環、ピリジン環、ピラジン環、ピリミジン環、ピリダジン環、アゼピン環、ジアゼピン環などの芳香族５～７員ヘテロ環；などが挙げられる。
　これらのうち芳香族炭化水素環が好ましく、ベンゼン環がより好ましい。 [E]
E shows unsubstituted or 5- to 7-membered hydrocarbon ring substituted with X 2, or unsubstituted or a 5-7 membered heterocyclic ring substituted with X 2.
As the 5- to 7-membered hydrocarbon ring, an aromatic hydrocarbon ring such as a benzene ring; a C5-7 cycloalkene ring such as a cyclopentene ring, cyclohexene ring, and cycloheptene ring; a furan ring, a thiophene ring, a pyrrole ring, and an imidazole ring , Pyrazole ring, thiazole ring, oxazole ring, isoxazole ring, isothiazole ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, azepine ring, diazepine ring and other aromatic 5- to 7-membered heterocycles; .
Of these, an aromatic hydrocarbon ring is preferable, and a benzene ring is more preferable.
〔Ｘ〕
　Ｘは、酸素原子（Ｏ）、窒素原子（ＮＨ）、または、Ｃ１～８アルキル基（Ｒ”）で置換された窒素原子（ＮＲ”）を示す。ここで、「Ｃ１～８アルキル基」は、Ｒ1で例示したものと同じものが挙げられる。 [X]
X represents an oxygen atom (O), a nitrogen atom (NH), or a nitrogen atom (NR ″) substituted with a C1-8 alkyl group (R ″). Here, examples of the “C1-8 alkyl group” are the same as those exemplified for R 1 .
　本発明化合物の塩としては、農園芸学的に許容される塩であれば、特に制限されない。塩としては、例えば、塩酸、硫酸などの無機酸の塩；酢酸、乳酸などの有機酸の塩；リチウム、ナトリウム、カリウムなどのアルカリ金属の塩；カルシウム、マグネシウムなどのアルカリ土類金属の塩；鉄、銅などの遷移金属の塩；アンモニア、トリエチルアミン、トリブチルアミン、ピリジン、ヒドラジンなどの有機塩基の塩などが挙げられる。 The salt of the compound of the present invention is not particularly limited as long as it is an agriculturally and horologically acceptable salt. Examples of the salt include salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium and potassium; salts of alkaline earth metals such as calcium and magnesium; Examples include salts of transition metals such as iron and copper; salts of organic bases such as ammonia, triethylamine, tributylamine, pyridine, and hydrazine.
〔式（II）で表される化合物〕
　本発明化合物は、式（II）で表される化合物（以下、「化合物（II）」と表記することがある。）であることが好ましい。 [Compound represented by Formula (II)]
The compound of the present invention is preferably a compound represented by the formula (II) (hereinafter sometimes referred to as “compound (II)”).
Figure JPOXMLDOC01-appb-C000013
Figure JPOXMLDOC01-appb-C000013
ここで、上記の式（II）中、Ｒ、Ｘ1、ｍ、Ｘ2、ｎ、Ｄ、Ｂ、およびＸは、上記の式（I）中のそれぞれと同じ意味を示す。
〔Ａ１、Ａ２、Ａ３、Ａ４〕
　Ａ１、Ａ２、Ａ３、およびＡ４は、それぞれ独立して、炭素原子または窒素原子を示す。すなわち、ベンゼン環、ピリジン環、ピリダジン環、ピリミジン環、ピラジン環、またはトリアジン環を構成する。 Here, in the above formula (II), R, X 1 , m, X 2, n, D, B, and X are as defined respectively in the above formula (I).
[A 1, A 2, A 3 , A 4 ]
A 1 , A 2 , A 3 , and A 4 each independently represent a carbon atom or a nitrogen atom. That is, it forms a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, or a triazine ring.
〔式（III）で表される化合物〕
　本発明化合物は、式（III）で表される化合物（以下、「化合物（III）」と表記することがある。）であることが好ましい。 [Compound represented by Formula (III)]
The compound of the present invention is preferably a compound represented by the formula (III) (hereinafter sometimes referred to as “compound (III)”).
Figure JPOXMLDOC01-appb-C000014
Figure JPOXMLDOC01-appb-C000014
　式（III）で表される化合物は、「Ｄ」がベンゼン環である化合物である。すなわち、本発明化合物は、キノリン環もしくはキノキサリン環を有する化合物であることが好ましい。
　ここで、上記の式（III）中、Ｒ、Ｘ1、ｍ、Ｘ2、ｎ、Ａ１、Ａ２、Ａ３、Ａ４、Ｂ、およびＸは、上記と同じ意味を示す。 The compound represented by the formula (III) is a compound in which “D” is a benzene ring. That is, the compound of the present invention is preferably a compound having a quinoline ring or a quinoxaline ring.
Here, in the above formula (III), R, X 1 , m, X 2, n, A 1, A 2, A 3, A 4, B, and X are as defined above.
〔式（IV）で表される化合物〕
　本発明化合物は、式（IV）で表される化合物（以下、「化合物（IV）」と表記することがある。）であることが好ましい。 [Compound represented by Formula (IV)]
The compound of the present invention is preferably a compound represented by the formula (IV) (hereinafter sometimes referred to as “compound (IV)”).
Figure JPOXMLDOC01-appb-C000015
Figure JPOXMLDOC01-appb-C000015
　式（IV）で表される化合物は、「Ｄ」がベンゼン環であり、「Ａ１～Ａ４」が炭素原子である化合物である。すなわち、本発明化合物は、キノリン環もしくはキノキサリン環のいずれかと、ベンゼン環を有する化合物であることが好ましい。
ここで、上記の式（IV）中、Ｒ、Ｘ1、ｍ、Ｘ2、ｎ、Ｂ、およびＸは、上記と同じ意味を示す。 The compound represented by the formula (IV) is a compound in which “D” is a benzene ring and “A 1 to A 4 ” are carbon atoms. That is, the compound of the present invention is preferably a compound having either a quinoline ring or a quinoxaline ring and a benzene ring.
Here, in the above formula (IV), R, X 1 , m, X 2 , n, B, and X have the same meaning as described above.
〔式（V）で表される化合物〕
　また、本発明化合物は、式（V）で表される化合物（以下、「化合物（V）」と表記することがある。）であることが好ましい。 [Compound represented by Formula (V)]
The compound of the present invention is preferably a compound represented by the formula (V) (hereinafter sometimes referred to as “compound (V)”).
Figure JPOXMLDOC01-appb-C000016
Figure JPOXMLDOC01-appb-C000016
ここで、式（V）中、Ｒ、Ｘ1、ｍ、Ｘ2、ｎ、Ｄ、Ｂ、およびＸは、上記の式（I）中のそれぞれと同じ意味を示す。
〔Ａ５、Ａ６、Ａ７〕
　Ａ５、Ａ６、およびＡ７は、それぞれ独立して、炭素原子、窒素原子、酸素原子、または硫黄原子を示す。ただし、酸素原子同士、硫黄原子同士、酸素原子と硫黄原子の組合わせが隣接することはない。
　すなわち、Ａ５、Ａ６、およびＡ７を含む環は、フラン環、チオフェン環、ピロ－ル環、イミダゾール環、ピラゾール環、チアゾール環、オキサゾール環、イソオキサゾール環、イソチアゾール環を構成する。 Here, in the formula (V), R, X 1 , m, X 2 , n, D, B, and X have the same meaning as in the above formula (I).
[A 5, A 6, A 7]
A 5 , A 6 , and A 7 each independently represent a carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom. However, oxygen atoms, sulfur atoms, or a combination of oxygen atoms and sulfur atoms are not adjacent to each other.
That is, the ring containing A 5 , A 6 , and A 7 constitutes a furan ring, a thiophene ring, a pyrrole ring, an imidazole ring, a pyrazole ring, a thiazole ring, an oxazole ring, an isoxazole ring, and an isothiazole ring.
〔式（VI）で表される化合物〕
　本発明化合物は、式（VI）で表される化合物（以下、「化合物（VI）」と表記することがある。）であることが好ましい。 [Compound represented by Formula (VI)]
The compound of the present invention is preferably a compound represented by the formula (VI) (hereinafter sometimes referred to as “compound (VI)”).
Figure JPOXMLDOC01-appb-C000017
Figure JPOXMLDOC01-appb-C000017
　式（VI）で表される化合物は、「Ｄ」がベンゼン環である化合物である。
ここで、式（VI）中、Ｒ、Ｘ1、ｍ、Ｘ2、ｎ、Ａ５、Ａ６、Ａ７、Ｂ、およびＸは、上記の式（V）中のそれぞれと同じ意味を示す。 The compound represented by the formula (VI) is a compound in which “D” is a benzene ring.
Here, in the formula (VI), R, X 1 , m, X 2 , n, A 5 , A 6 , A 7 , B, and X have the same meaning as in the above formula (V). .
〔本発明化合物の製造方法〕
　本発明化合物は、例えば以下に示す合成方法によって製造することができる。 [Method for producing compound of the present invention]
The compound of the present invention can be produced, for example, by the synthesis method shown below.
（合成方法１）
　式（１）で表される化合物と式（２）で表される化合物とを公知の方法によって反応させて化合物（II）を製造することができる。
式中、Ｒ、Ｘ1、ｍ、Ｘ2、ｎ、Ｄ、Ａ１～Ａ４、Ｂ、およびＸは前記と同じ意味を示す。Ｑはハロゲノ基を示す。
　本発明においては、７，８－ジフルオロ－３－ヨード－キノリンが、有用な製造中間体である。 (Synthesis method 1)
Compound (II) can be produced by reacting the compound represented by formula (1) with the compound represented by formula (2) by a known method.
In the formula, R, X 1 , m, X 2 , n, D, A 1 to A 4 , B, and X have the same meaning as described above. Q represents a halogeno group.
In the present invention, 7,8-difluoro-3-iodo-quinoline is a useful production intermediate.
Figure JPOXMLDOC01-appb-C000018
      

  　 
Figure JPOXMLDOC01-appb-C000018
      

  　 
（合成方法２）
　式（３）で表される化合物と式（４）で表される化合物とを公知の方法によって反応させて化合物（II）を製造することができる。
式中、Ｒ、Ｘ1、ｍ、Ｘ2、ｎ、Ｄ、Ａ１～Ａ４、Ｂ、Ｘ、およびＱは前記と同じ意味を示す。
　本発明においては、８－フルオロ－３－ヒドロキシキノリン、７，８－ジフルオロ－３－ヒドロキシキノリン、８－フルオロ－３－ヒドロキシ－２－メチルキノリン、または７，８－ジフルオロ－３－ヒドロキシ－２－メチルキノリンが、有用な製造中間体である。 (Synthesis method 2)
Compound (II) can be produced by reacting the compound represented by formula (3) with the compound represented by formula (4) by a known method.
In the formula, R, X 1 , m, X 2 , n, D, A 1 to A 4 , B, X, and Q have the same meaning as described above.
In the present invention, 8-fluoro-3-hydroxyquinoline, 7,8-difluoro-3-hydroxyquinoline, 8-fluoro-3-hydroxy-2-methylquinoline, or 7,8-difluoro-3-hydroxy-2 -Methylquinoline is a useful production intermediate.
Figure JPOXMLDOC01-appb-C000019
      

  　 
Figure JPOXMLDOC01-appb-C000019
      

  　 
（合成方法３）
　式（１）で表される化合物と式（５）で表される化合物とを公知の方法によって反応させて化合物（V）を製造することができる。
式中、Ｒ、Ｘ1、ｍ、Ｘ2、ｎ、Ｄ、Ａ５～Ａ７、Ｂ、Ｘ、Ｑは前記と同じ意味を示す。 (Synthesis method 3)
Compound (V) can be produced by reacting the compound represented by formula (1) with the compound represented by formula (5) by a known method.
In the formula, R, X 1 , m, X 2 , n, D, A 5 to A 7 , B, X, and Q have the same meaning as described above.
Figure JPOXMLDOC01-appb-C000020
      

  　 
Figure JPOXMLDOC01-appb-C000020
      

  　 
（合成方法４）
　式（３）で表される化合物と式（６）で表される化合物とを公知の方法によって反応させて化合物（Ｖ）を製造することができる。
式中、Ｒ、Ｘ1、ｍ、Ｘ2、ｎ、Ｄ、Ａ５～Ａ７、Ｂ、Ｘ、Ｑは前記と同じ意味を示す。 (Synthesis method 4)
Compound (V) can be produced by reacting the compound represented by formula (3) with the compound represented by formula (6) by a known method.
In the formula, R, X 1 , m, X 2 , n, D, A 5 to A 7 , B, X, and Q have the same meaning as described above.
Figure JPOXMLDOC01-appb-C000021
      

  　 
Figure JPOXMLDOC01-appb-C000021
      

  　 
　本発明に係る化合物の塩は、無機酸化合物、有機酸化合物、アルカリ金属化合物、アルカリ土類金属化合物、遷移金属化合物、アンモニウム化合物などを化合物（I）に接触させることによって調製することができる。 The salt of the compound according to the present invention can be prepared by bringing a compound (I) into contact with an inorganic acid compound, an organic acid compound, an alkali metal compound, an alkaline earth metal compound, a transition metal compound, an ammonium compound, or the like.
　いずれの反応においても、反応終了後は、有機合成化学における通常の後処理操作、および、必要に応じて従来公知の分離精製手段を施すことによって、目的物を効率よく単離することができる。 In any reaction, after completion of the reaction, the target product can be efficiently isolated by subjecting it to conventional post-treatment operations in synthetic organic chemistry and, if necessary, conventionally known separation and purification means.
　目的物の構造は、1H-NMRスペクトル、IRスペクトル、マススペクトルの測定や、元素分析などによって、同定・確認することができる。 The structure of the target product can be identified and confirmed by measuring 1 H-NMR spectrum, IR spectrum, mass spectrum, elemental analysis, etc.
２）農園芸用殺菌剤
　本発明に係る農園芸用殺菌剤は、本発明に係る含窒素ヘテロ環化合物またはその塩から選ばれる少なくとも１種を有効成分として含有する。 2) Agricultural and horticultural fungicide The agricultural and horticultural fungicide according to the present invention contains at least one selected from the nitrogen-containing heterocyclic compound or a salt thereof according to the present invention as an active ingredient.
　本発明の農園芸用殺菌剤は、広範囲の種類の糸状菌、例えば、藻菌類（Oomycetes）、子のう（嚢）菌類（Ascomycetes）、不完全菌類（Deuteromycetes）、担子菌類（Basidiomycetes）に属する菌に対し優れた殺菌力を有する。 The agricultural and horticultural fungicides of the present invention belong to a wide variety of filamentous fungi, for example, algae fungi (Oomycetes), Ascomycetes, Deuteromycetes, and Basidiomycetes Has excellent bactericidal power against bacteria.
　本発明の農園芸用殺菌剤は、花卉、芝、牧草を含む農園芸作物の栽培に際し発生する種々の病害の防除のために、種子処理、茎葉散布、土壌施用または水面施用などの方法において使用することができる。 The agricultural and horticultural fungicide of the present invention is used in methods such as seed treatment, foliage application, soil application, and water surface application for the control of various diseases that occur during the cultivation of agricultural and horticultural crops including flowers, turf, and grass. can do.
　例えば、
　テンサイ：褐斑病（Cercospora beticola)、黒根病(Aphanomyces cochlloides)、根腐病(Thanatephorus cucumeris)、葉腐病(Thanatephorus cucumeris)；
　ラッカセイ：褐斑病(Mycosphaerella arachidis)、黒渋病(Mycosphaerella berkeleyi)；
　キュウリ：うどんこ病(Sphaerotheca fuliginea)、べと病(Pseudoperonospora cubensis)、つる枯病(Mycosphaerella melonis)、つる割病(Fusarium oxysporum)、菌核病(Sclerotinia sclerotiorum)、灰色かび病(Botrytis cinerea)、炭そ病(Colletotrichum orbiculare)、黒星病(Cladosporium cucumerinum)、褐斑病(Corynespora cassicola)、苗立枯病(Pythium debaryanam、Rhizoctonia solani Kuhn)、斑点細菌病(Pseudomonas syringae pv.Lecrymans)；
　トマト：灰色かび病(Botrytis cinerea)、葉かび病(Cladosporium fulvum)、疫病(Phytophthora infestans)；
　ナス：灰色かび病(Botrytis cinerea)、黒枯病(Corynespora melongenae)、うどんこ病(Erysiphe cichoracearum)、すすかび病(Mycovellosiella nattrassii)； For example,
Sugar beet: brown spot (Cercospora beticola), black root (Aphanomyces cochlloides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris);
Peanut: brown spot (Mycosphaerella arachidis), black astringency (Mycosphaerella berkeleyi);
Cucumber: powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), vine blight (Mycosphaerella melonis), vine split disease (Fusarium oxysporum), mycorrhizal disease (Sclerotinia sclerotiorum), gray mold disease (Botrytis cinerea) Anthracnose (Colletotrichum orbiculare), black spot (Cladosporium cucumerinum), brown spot (Corynespora cassicola), seedling blight (Pythium debaryanam, Rhizoctonia solani Kuhn), spot bacterial disease (Pseudomonas syringae pv. Lecrymans);
Tomato: gray mold (Botrytis cinerea), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans);
Eggplant: gray mold (Botrytis cinerea), black blight (Corynespora melongenae), powdery mildew (Erysiphe cichoracearum), subtle mold (Mycovellosiella nattrassii);
　イチゴ：灰色かび病(Botrytis cinerea)、うどんこ病(Sohaerotheca humuli)、炭そ病(Colletotrichum acutatum、Colletotrichum fragariae)、疫病(Phytophthora cactorum)；
　タマネギ：灰色腐敗病(Botrytis allii)、灰色かび病(Botrytis cinerea)、白斑葉枯病(Botrytis squamosa)、べと病(Peronospora destructor)；
　キャベツ：根こぶ病(Plasmodiophora brassicae)、軟腐病(Erwinia carotovora)、べと病(Peronospora parasitica)；
　インゲン：菌核病(Sclerotinia sclerotiorum)、灰色かび病(Botrytis cinerea)；
　りんご：うどんこ病(Podosphaera leucotricha)、黒星病(Venturia inaequalis)、モニリア病(Monilinia mali)、黒点病(Mycosphaerella pomi)、腐らん病(Valsa mali)、斑点落葉病(Alternaria mali)、赤星病(Gymnosporangium yamadae)、輪紋病(Botryosphaeria berengeriana)、炭そ病(Glomerella cingulata、Colletotrichum acutatum)、褐斑病(Diplocarpon mali)、すす点病(Zygophiala jamaicensis)、すす斑病(Gloeodes pomigena)；
　カキ：うどんこ病(Phyllactinia kakicola)、炭そ病(Gloeosporium kaki)、角斑落葉病(Cercospora kaki)； Strawberry: Gray mold (Botrytis cinerea), powdery mildew (Sohaerotheca humuli), anthracnose (Colletotrichum acutatum, Colletotrichum fragariae), plague (Phytophthora cactorum);
Onion: gray rot (Botrytis allii), gray mold (Botrytis cinerea), white leaf blight (Botrytis squamosa), downy mildew (Peronospora destructor);
Cabbage: root-knot disease (Plasmodiophora brassicae), soft rot disease (Erwinia carotovora), downy mildew (Peronospora parasitica);
Green beans: Sclerotinia sclerotiorum, gray mold (Botrytis cinerea);
Apple: powdery mildew (Podosphaera leucotricha), black spot disease (Venturia inaequalis), monilinia disease (Monilinia mali), black spot disease (Mycosphaerella pomi), rot disease (Valsa mali), spotted leaf disease (Alternaria mali), red star disease (Gymnosporang) yamadae), ring rot (Botryosphaeria berengeriana), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), soot spot (Zygophiala jamaicensis), soot spot (Gloeodes pomigena);
Oysters: powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), deciduous leaf spot (Cercospora kaki);
　モモ：灰星病(Monilinia fructicola)、黒星病(Cladosporium carpophilum)、ホモプシス腐敗病(Phomopsis sp.)；
　オウトウ：灰星病(Monilinia fructicola)；
　ブドウ：灰色かび病(Botrytis cinerea)、うどんこ病(Uncinula necator)、晩腐病(Glomerella cingulata、Colletotrichum acutatum)、べと病(Plasmopara viticola)、黒とう病(Elsinoe ampelina)、褐斑病(Pseudocercospora vitis)、黒腐病(Guignardia bidwellii)；
　ナシ：黒星病(Venturia nashicola)、赤星病(Gymnosporangium asiaticum)、黒斑病(Alternaria kikuchiana)、輪紋病(Botryosphaeria berengeriana)、うどんこ病(Phyllactinia mali)；
　チャ：輪斑病(Pestalotia theae)、炭そ病(Colletotrichum theae-sinensis)；
　カンキツ：そうか病(Elsinoe fawcetti)、青かび病(Penicillium italicum)、緑かび病(Penicillium digitatum)、灰色かび病(Botrytis cinerea)、黒点病(Diaporthe citri)、かいよう病(Xanthomonas campestris pv.Citri)；
　コムギ：うどんこ病(Erysiphe graminis f.sp.tritici)、赤かび病(Gibberella zeae)、赤さび病(Puccinia recondita)、褐色雪腐病(Pythium iwayamai)、紅色雪腐病(Monographella nivalis)、眼紋病(Pseudocercosporella herpotrichoides)、葉枯病(Septoria tritici)、ふ枯病(Leptosphaeria nodorum)、雪腐小粒菌核病(Typhula incarnata)、雪腐大粒菌核病(Myriosclerotinia borealis)、立枯病(Gaeumanomyces graminis)； Peach: Monilinia fructicola, black scab (Cladosporium carpophilum), homopsis sp. (Phomopsis sp.);
Sweet cherry: Monilinia fructicola;
Grapes: gray mold (Botrytis cinerea), powdery mildew (Uncinula necator), late rot (Glomerella cingulata, Colletotrichum acutatum), downy mildew (Plasmopara viticola), black scab (Elsinoe ampelina), brown spot (Pseudocercospora) vitis), black rot (Guignardia bidwellii);
Pear: Black star disease (Venturia nashicola), Red star disease (Gymnosporangium asiaticum), Black spot disease (Alternaria kikuchiana), Ring rot disease (Botryosphaeria berengeriana), Powdery mildew (Phyllactinia mali);
Cha: Ring spot disease (Pestalotia theae), anthracnose (Colletotrichum theae-sinensis);
Citrus: scab (Elsinoe fawcetti), blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), black spot (Diaporthe citri), scab (Xanthomonas campestris pv.Citri);
Wheat: powdery mildew (Erysiphe graminis f.sp.tritici), red mold (Gibberella zeae), red rust (Puccinia recondita), brown snow rot (Pythium iwayamai), red snow rot (Monographella nivalis), eyeprint Disease (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), blight (Leptosphaeria nodorum), snow rot microbe nuclei (Typhula incarnata), snow rot microbacilli (Myriosclerotinia borealis), blight (Gaeumanomyces graminis) );
　オオムギ：斑葉病(Pyrenophora graminea)、雲形病(Rhynchosporium secalis)、裸黒穂病(Ustilago tritici、U.nuda)；
　イネ：いもち病(Pyricularia oryzae)、紋枯病(Rhizoctonia solani)、馬鹿苗病(Gibberella fujikuroi)、ごま葉枯病(Cochliobolus niyabeanus)、苗立枯病(Pythium graminicolum)、白葉枯病(Xanthomonas oryzae)、苗立枯細菌病(Burkholderia plantarii)、褐条病(Acidovorax avenae)、もみ枯細菌病(Burkholderia glumae)；
　タバコ：菌核病(Sclerotinia sclerotiorum)、うどんこ病(Erysiphe cichoracearum)；
　チューリップ：灰色かび病(Botrytis cinerea)；
　ベントグラス：雪腐大粒菌核病(Sclerotinia borealis)、赤焼病(Pythium aphanidermatum)；
　オーチャードグラス：うどんこ病(Erysiphe graminis)；
　ダイズ：紫斑病(Cercospora kikuchii)、べと病(Peronospora Manshurica)、茎疫病(Phytophthora sojae)；
　ジャガイモ・トマト：疫病(Phytophthora infestans)；
などの防除に使用することができる。 Barley: leafy leaf disease (Pyrenophora graminea), cloud shape disease (Rhynchosporium secalis), naked smut (Ustilago tritici, U.nuda);
Rice: Rice Blast (Pyricularia oryzae), Rhizoctonia solani, Idiot Seedling (Gibberella fujikuroi), Sesame Leaf Blight (Cochliobolus niyabeanus), Seedling Blight (Pythium graminicolum), White Leaf Blight (Xanthomonas oryzae) Bacterial disease (Burkholderia plantarii), Brown disease (Acidovorax avenae), Bacterial disease (Burkholderia glumae);
Tobacco: Sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum);
Tulip: Gray mold disease (Botrytis cinerea);
Bentgrass: Sclerotinia borealis, Pythium aphanidermatum;
Orchard grass: powdery mildew (Erysiphe graminis);
Soybean: Purpura (Cercospora kikuchii), downy mildew (Peronospora Manshurica), stem rot (Phytophthora sojae);
Potato tomato: Phytophthora infestans;
It can be used for controlling such as.
　また、本発明の農園芸用殺菌剤は、耐性菌に対しても優れた殺菌効果を有する。耐性菌としては、チオファネートメチル、ベノミル、カルベンダジムなどのベンズイミダゾール系殺菌剤に耐性を示す灰色かび病菌（Botrytis cinerea）やテンサイ褐斑病菌（Cercospora beticola）、リンゴ黒星病菌（Venturia inaequalis）、ナシ黒星病菌（Venturia nashicola）；ジカルボキシイミド系殺菌剤（例えば、ビンクロゾリン、プロシミドン、イプロジオン）に耐性を示す灰色かび病菌（Botrytis cinerea）などが挙げられる。 Also, the agricultural and horticultural fungicide of the present invention has an excellent bactericidal effect against resistant bacteria. The resistant bacteria include gray mold fungus (Botrytis cinerea), sugar beet brown fungus (Cercospora beticola), apple black rot fungus (Venturia inaequalis), pear black scab (Venturia nashicola); a gray mold fungus (Botrytis cinerea) resistant to dicarboximide fungicides (for example, vinclozolin, procymidone, iprodione) and the like.
　本発明の農園芸用殺菌剤の適用がより好ましい病害としては、リンゴの黒星病、キュウリの灰色かび病、コムギのうどんこ病、トマトの疫病、コムギの赤さび病、水稲のいもち病、キュウリのつる割病などが挙げられる。 More preferable diseases to which the agricultural and horticultural fungicide of the present invention is applied include black scab of apple, gray mold of cucumber, powdery mildew of wheat, plague of tomato, leaf rust of wheat, rice blast of rice, cucumber Examples include vine split disease.
　また、本発明の農園芸用殺菌剤は薬害が少なく、魚類や温血動物への毒性が低く、安全性の高い薬剤である。
　本発明の農園芸用殺菌剤は、農薬としてとり得る形態、即ち、水和剤、粒剤、粉剤、乳剤、水溶剤、懸濁剤、顆粒水和剤などの農薬製剤の形態で使用することができる。 In addition, the agricultural and horticultural fungicide of the present invention is a highly safe drug with little phytotoxicity, low toxicity to fish and warm-blooded animals.
The agricultural and horticultural fungicide of the present invention should be used in the form that can be taken as an agrochemical, that is, in the form of an agrochemical formulation such as a wettable powder, a granule, a powder, an emulsion, an aqueous solvent, a suspension, or a granular wettable powder. Can do.
　固体の製剤に用いられる添加剤および担体としては、大豆粉、小麦粉などの植物性粉末、珪藻土、燐灰石、石こう、タルク、ベントナイト、パイロフィライト、クレーなどの鉱物性微粉末、安息香酸ソーダ、尿素、芒硝などの有機および無機化合物などが挙げられる。 Additives and carriers used in solid formulations include vegetable powders such as soybean flour and wheat flour, mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay, sodium benzoate, urea And organic and inorganic compounds such as mirabilite.
　液体の製剤に用いられる溶剤としては、ケロシン、キシレンおよび石油系の芳香族炭化水素、シクロヘキサン、シクロヘキサノン、ジメチルホルムアミド、ジメチルスルホキシド、アルコール、アセトン、トリクロロエチレン、メチルイソブチルケトン、鉱物油、植物油、水などが挙げられる。 Solvents used in liquid formulations include kerosene, xylene and petroleum aromatic hydrocarbons, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, vegetable oil, water, etc. Can be mentioned.
　さらに、これらの製剤において均一かつ安定な形態をとるために、必要に応じて界面活性剤を添加することができる。
　添加することができる界面活性剤は特に限定されない。例えば、ポリオキシエチレンが付加したアルキルフェニルエーテル、ポリオキシエチレンが付加したアルキルエーテル、ポリオキシエチレンが付加した高級脂肪酸エステル、ポリオキシエチレンが付加したソルビタン高級脂肪酸エステル、ポリオキシエチレンが付加したトリスチリルフェニルエーテルなどの非イオン性界面活性剤、ポリオキシエチレンが付加したアルキルフェニルエーテルの硫酸エステル塩、アルキルベンゼンスルホン酸塩、高級アルコールの硫酸エステル塩、アルキルナフタレンスルホン酸塩、ポリカルボン酸塩、リグニンスルホン酸塩、アルキルナフタレンスルホン酸塩のホルムアルデヒド縮合物、イソブチレン－無水マレイン酸共重合体などが挙げられる。 Furthermore, in order to take a uniform and stable form in these preparations, a surfactant can be added as necessary.
The surfactant that can be added is not particularly limited. For example, alkyl phenyl ether added with polyoxyethylene, alkyl ether added with polyoxyethylene, higher fatty acid ester added with polyoxyethylene, sorbitan higher fatty acid ester added with polyoxyethylene, tristyryl added with polyoxyethylene Nonionic surfactants such as phenyl ether, sulfates of alkylphenyl ethers added with polyoxyethylene, alkylbenzene sulfonates, sulfates of higher alcohols, alkylnaphthalene sulfonates, polycarboxylates, lignin sulfones Acid salt, formaldehyde condensate of alkyl naphthalene sulfonate, and isobutylene-maleic anhydride copolymer.
　このようにして得られた水和剤、乳剤、フロアブル剤、水溶剤、若しくは顆粒水和剤は、水で所定の濃度に希釈して、溶解液、懸濁液あるいは乳濁液として植物に散布するなどして使用することができる。また、粉剤・粒剤はそのまま植物に散布するなどして使用することができる。 The wettable powder, emulsion, flowable powder, aqueous solvent, or granular wettable powder thus obtained is diluted with water to a predetermined concentration and sprayed on plants as a solution, suspension or emulsion. Can be used. In addition, powders and granules can be used by spraying them on plants as they are.
　本発明の農園芸用殺菌剤中における有効成分量は、製剤全体に対して、好ましくは０．０１～９０重量％、より好ましくは０．０５～８５重量％である。 The amount of the active ingredient in the agricultural and horticultural fungicide of the present invention is preferably 0.01 to 90% by weight, more preferably 0.05 to 85% by weight, based on the whole preparation.
　本発明の農園芸用殺菌剤の施用量は、気象条件、製剤形態、施用時期、施用方法、施用場所、防除対象病害、対象作物などにより異なるが、通常１ヘクタール当たり有効成分化合物量にして１～１，０００ｇ、好ましくは１０～１００ｇである。 The application amount of the agricultural and horticultural fungicide of the present invention varies depending on weather conditions, formulation form, application time, application method, application place, disease to be controlled, target crop, etc., but it is usually 1 in terms of the amount of active ingredient compound per hectare. ˜1,000 g, preferably 10 to 100 g.
　水和剤、乳剤、懸濁剤、水溶剤、顆粒水和剤などを水で希釈して施用する場合、その施用濃度は１～１０００ｐｐｍ、好ましくは１０～２５０ｐｐｍである。 When a wettable powder, emulsion, suspension, aqueous solvent, granular wettable powder or the like is diluted with water and applied, the applied concentration is 1 to 1000 ppm, preferably 10 to 250 ppm.
　本発明の農園芸用殺菌剤には、他の殺菌剤や殺虫・殺ダニ剤、共力剤を混合することができる。また、本発明の農園芸用殺菌剤と他の殺菌剤や殺虫・殺ダニ剤、共力剤とを同時にまたは相前後して使用することができる。
　混合して使用できる他の殺菌剤、殺虫・殺ダニ剤、植物生長調節剤の代表例を以下に示す。 The agricultural and horticultural fungicide of the present invention may be mixed with other fungicides, insecticides / acaricides, and synergists. In addition, the agricultural and horticultural fungicide of the present invention and other fungicides, insecticides / acaricides, and synergists can be used simultaneously or in succession.
Typical examples of other fungicides, insecticides / miticides, and plant growth regulators that can be used in combination are shown below.
殺菌剤：
（１）ベンゾイミダゾール系：ベノミル、カルベンダジム、フベリダゾール、チアベンダゾール、チオファネート メチル等；
（２）ジカルボキシイミド系：クロゾリネート、イプロジオン、プロシミドン、ビンクロゾリン等；
（３）DMI－殺菌剤系：イマザリル、オキスポコナゾール、ペフラゾエート、プロクロラズ、トリフルミゾール、トリホリン、ピリフェノックス、フェナリモル、ヌアリモル、アザコナゾール、ビテルタノール、ブロムコナゾール、シプロコナゾール、ジフェノコナゾール、ジニコナゾール、エポキシコナゾール、フェンブコナゾール、フルキンコナゾール、フルシラゾール、フルトリアホル、ヘキサコナゾール、イミベンコナゾール、イプコナゾール、メトコナゾール、ミクロブタニル、ペンコナゾール、プロピコナゾール、プロチオコナゾール、シメコナゾール、テブコナゾール、テトラコナゾール、トリアジメホン、トリアジメノール、トリチコナゾール、エタコナゾール、ファーコナゾールシス等；
（４）フェニルアミド系：ベナラキシル、フララキシル、メタラキシル、メタラキシル－M、オキサジキシル、オフラセ等；
（５）アミン系：アルジモルフ、ドデモルフ、フェンプロピモルフ、トリデモルフ、フェンプロピジン、ピペラリン、スピロキサミン等；
（６）ホスホロチオレート系：EDDP、イプロベンホス、ピラゾホス等；
（７）ジチオラン系：イソプロチオラン等；
（８）カルボキサミド：ベノダニル、ボスカリド、カルボキシン、フェンフラン、フルトラニル、フラメトピル、メプロニル、オキシカルボキシン、ペンチオピラド、チフルザミド等；
（９）ヒドロキシ-(2-アミノ) ピリミジン系：ブピリメート、ジメチリモル、エチリモル等；
（１０）AP殺菌剤 (アニリノピリミジン)系：シプロジニル、メパニピリム、ピリメタニル等； Fungicide:
(1) benzimidazole series: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate methyl, etc .;
(2) Dicarboximide type: Clozolinate, iprodione, procymidone, vinclozolin and the like;
(3) DMI-bactericidal system: imazalyl, oxpoconazole, pefazoate, prochloraz, triflumizole, triphorin, pyrifenox, fenarimol, nuarimol, azaconazole, viteltanol, bromconazole, cyproconazole, difenoconazole, diniconazole, Epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafor, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole, prothioconazole, cimeconazole, tebuconazole, tetraconazole, triazimephone, Triadimenol, triticonazole, etaconazole, farconazole cis etc .;
(4) Phenylamide: Benalaxyl, furaxyl, metalaxyl, metalaxyl-M, oxadixyl, ophthalse, etc .;
(5) Amine type: aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine, etc .;
(6) phosphorothiolate type: EDDP, iprobenphos, pyrazophos, etc .;
(7) Dithiolane type: isoprothiolane and the like;
(8) Carboxamide: benodanyl, boscalid, carboxin, fenfuran, flutolanyl, furamethopyl, mepronil, oxycarboxin, pentiopyrad, tifluzamide and the like;
(9) Hydroxy- (2-amino) pyrimidine series: bupyrimeto, dimethylolymol, ethylimole, etc .;
(10) AP fungicide (anilinopyrimidine) type: cyprodinil, mepanipyrim, pyrimethanil, etc .;
（１１）N-フェニルカーバメート系：ジエトフェンカルブ等；
（１２）QoI-殺菌剤 (Qo阻害剤)系：アゾキシストロビン、ピコキシストロビン、ピラクロストロビン、クレソキシム-メチル、トリフロキシストロビン、ジモキシストロビン、メトミノストロビン、オリザストロビン、ファモキサドン、フルオキサストロビン、フェンアミドン、メトミノフェン等；
（１３）PP殺菌剤 (フェニルピロール)系：フェンピコニル、フルジオキソニル等；
（１４）キノリン系：キノキシフェン等；
（１５）AH殺菌剤 (芳香族炭化水素）系：ビフェニル、クロロネブ、ジクロラン、キントゼン、テクナゼン、トルクトフォス-メチル等；
（１６）MBI-R系：フサライド、ピロキロン、トリシクラゾール等；
（１７）MBI-D系：カルプロパミド、ジクロシメット、フェノキサニル等；
（１８）SBI剤：フェンヘキサミド、ピリブチカルブ、タービナフィン等；
（１９）フェニルウレア：ペンシクロン等；
（２０）QiI-殺菌剤 (Qi阻害剤)：シアゾファミド等；
（２１）ベンズアミド系：ゾキサミド等；
（２２）エノピランウロン系：ブラストサイジン、ミルディオマイシン等；
（２３）へキソピラノシル系：カスガマイシン等；
（２４）グルコピラノシル系：ストレプトマイシン、バリダマイシン等；
（２５）シアノアセトアミド系：シモキサニル等；
（２６）カーバメート系：ヨードカルブ、プロパモカルブ、プロチオカルブ、ポリカーバメート等；
（２７）脱共役剤：ビナパクリル、ジノカップ、フェリムゾン、フルアジナム等；
（２８）有機スズ化合物：酢酸トリフェニルスズ、塩化トリフェニルスズ、水酸化トリフェニルスズ等；
（２９）リン酸エステル：亜リン酸、トルクロホスメチル、ホセチル等； (11) N-phenyl carbamate type: dietofencarb and the like;
(12) QoI-bactericidal (Qo inhibitor) system: azoxystrobin, picoxystrobin, pyraclostrobin, cresoxime-methyl, trifloxystrobin, dimoxystrobin, metminostrobin, orizastrobin, Famoxadone, floxastrobin, phenamidon, metminophen, etc .;
(13) PP fungicide (phenylpyrrole) type: fenpiconyl, fludioxonil, etc .;
(14) Quinoline series: quinoxyphene and the like;
(15) AH disinfectant (aromatic hydrocarbon) series: biphenyl, chloronebu, dichlorane, kintozen, technazen, torquetophos-methyl, etc .;
(16) MBI-R series: fusaride, pyrokilone, tricyclazole, etc .;
(17) MBI-D system: carpropamide, diclocimet, phenoxanyl, etc .;
(18) SBI agents: fenhexamide, pyributicarb, terbinafine, etc .;
(19) Phenylurea: pencyclon and the like;
(20) QiI-bactericidal agent (Qi inhibitor): cyazofamid and the like;
(21) benzamide type: zoxamide and the like;
(22) Enopyranuron series: blastcidin, mildiomycin, etc .;
(23) Hexopyranosyl: Kasugamycin and the like;
(24) Glucopyranosyl type: streptomycin, validamycin and the like;
(25) Cyanoacetamide series: Simoxanyl and the like;
(26) Carbamate series: iodocarb, propamocarb, prothiocarb, polycarbamate and the like;
(27) Uncoupler: Vinacacryl, Zinocup, Ferimzone, Fluazinam, etc .;
(28) Organotin compounds: triphenyltin acetate, triphenyltin chloride, triphenyltin hydroxide and the like;
(29) Phosphate ester: phosphorous acid, tolcrofosmethyl, fosetyl and the like;
（３０）フタルアミド酸系：テクロフタラム等；
（３１）ベンゾトリアジン系：トリアゾキシド等；
（３２）ベンゼンスルフォナミド系：フルスルファミド等；
（３３）ピリダジノン：ジクロメジン等；
（３４）CAA 殺菌剤 (カルボン酸アミド)系：ジメトモルフ、フルモルフ、ベンチアバリカルブ、イプロバリカルブ、マンジプロパミド等；
（３５）テトラサイクリン：オキシテトラサイクリン等；
（３６）チオカーバメート系：メタスルホカルブ等；
（３７）その他の化合物：エトリジアゾール、ポリオキシン、オキソリニック酸、ヒドロキシイソキサゾール、オクチノリン、シルチオファム、ジフルメトリム、アシベンゾラルＳメチル、プロベナゾール、チアジニル、エタボキサム、シフルフェナミド、プロキナジド、メトラフェノン、フルオピコリド、水酸化第二銅、有機銅、硫黄、ファーバム、マンゼブ、マンネブ、メチラム、プロピネブ、チウラム、ジネブ、ジラム、キャプタン、カプタホール、フォルペット、クロロタロニル、ジクロフルアニド、トリルフルアニド、ドジン、グアザチン、イミノクタジン酢酸塩、イミノクタジンドデシルベンゼンスルホン酸塩、アニラジン、ジチアノン、クロロピクリン、ダゾメット、キノメチオネート、シプロフラム、シルチオファム、アグロバクテリウム、フルオルイミド)等； (30) phthalamic acid type: teclophthalam, etc .;
(31) Benzotriazine type: triazoxide and the like;
(32) benzenesulfonamide series: fursulfamide and the like;
(33) Pyridazinone: Dichromedin and the like;
(34) CAA disinfectant (carboxylic amide) type: dimethomorph, fulmorph, benchavaricarb, iprovaricarb, mandipropamide and the like;
(35) Tetracycline: oxytetracycline and the like;
(36) Thiocarbamate type: metasulfocarb, etc.
(37) Other compounds: etridiazole, polyoxin, oxolinic acid, hydroxyisoxazole, octinoline, silthiofam, diflumetrim, acibenzoral S methyl, probenazole, thiazinyl, ethaboxam, cyflufenamide, proquinazide, metolaphenone, fluopicolide, cupric hydroxide, organic Copper, sulfur, farbum, manzeb, mannebu, manebu, methylam, propineb, thiuram, dineb, diram, captan, captahol, phorpet, chlorothalonil, diclofluuride, tolylfluanid, dodine, guazatine, iminocazine acetate, iminoctadine dodecylbenzenesulfonic acid Salt, anilazine, dithianone, chloropicrin, dazomet, quinomethionate, ciprofuram, silthiofam, ag Bacterium, Furuoruimido) and the like;
殺虫・殺ダニ剤、殺線虫剤、殺土壌害虫剤、駆虫剤：
（１）有機（チオ）ホスフェート系：アセフェート、アザメチホス、アジンホス・メチル、アジンホス・エチル、ブロモホス・エチル、ブロムフェンビンホス、BRP、クロルピリホス、クロルピリホス・メチル、クロルピリホス・エチル、クロルフェンビンホス、カズサホス、カルボフェノチオン、クロルエトキシホス、クロルメホス、クマホス、シアノフェンホス、シアノホス、CYAP、ダイアジノン、ジクロルボス、ジクロトホス、ジメトエート、ジスルホトン、ジメトン-Ｓ-メチル、ジメチルビンホス、ジメトン－Ｓ－メチルスルホン、ジアリホス、ダイアジノン、ジクロフェンチオン、ジオキサベンゾホス、ジスルホトン、エチオン、エトプロホス、エトリムホス、EPN、フェナミホス、フェニトロチオン、フェンチオン、フェンスルホチオン、フルピラゾホス、ホノホス、ホルモチオン、ホスメチラン、ヘプテノホス、イサゾホス、ヨードフェンホス、イソフェンホス、イソキサチオン、イプロベンホス、マラチオン、メビンホス、メタミドホス、メチダチオン、モノクロトホス、メカルバム、メタクリホス、ナレッド、オメトエート、オキシジメトン・メチル、パラオクソン、パラチオン、パラチオン・メチル、フェントエート、ホサロン、ホスメット、ホスファミドン、ホレート、ホキシム、ピリミホス・メチル、ピリミホス・エチル、プロフェノホス、プロチオホス、ホスチアゼート、ホスホカルブ、プロパホス、プロペタムホス、プロトエート、ピリダフェンチオン、ピラクロホス、キナルホス、サリチオン、スルプロホス、スルホテップ、テトラクロルビンホス、テルブホス、トリアゾホス、トリクロルホン、テブピリムホス、テメホス、チオメトン、バミドチオン；
（２）カルバメート系：アラニカルブ、アルジカルブ、ベンダイオカルブ、ベンフラカルブ、カルバリル、カルボフラン、カルボスルファン、フェノキシカルブ、フェノチオカルブ、メチオカルブ、メソミル、オキサミル、ピリミカーブ、プロポキスル、チオジカルブ、トリアザメート、エチオフェンカルブ、フェノブカルブ、MIPC、MPMC、MTMC、ピリダフェンチオン、フラチオカルブ、XMC、アルドキシカルブ、アリキシカルブ、アミノカルブ、ベンダイオカルブ、ブフェンカルブ、ブタカルブ、ブトカルボキシム、ブトキシカルボキシム、クロエトカルブ、ジメチラン、ホルメタネート、イソプロカルブ、メタム・ナトリウム、メトルカルブ、プロメカルブ、チオファノックス、トリメタカルブ、キシリルカルブ；
（３）ピレトロイド系：アレトリン、ビフェントリン、シフルトリン、ベータ・シフルトリン、シハロトリン、ラムダ・シハロトリン、シフェノトリン、シペルメトリン、アルファ・シペルメトリン、ベータ・シペルメトリン、ゼタ・シペルメトリン、デルタメトリン、エスフェンバレレート、エトフェンプロックス、フェンプロパトリン、フェンバレレート、イミプロトリン、ペルメトリン、プラレトリン、ピレトリン、ピレトリンI、ピレトリンII、レスメトリン、シラフルオフェン、フルバリネート、テフルトリン、テトラメトリン、トラロメトリン、トランスフルトリン、プロフルトリン、ジメフルトリン、アクリナトリン、シクロプロトリン、ハルフェンプロックス、フルシトリネート、ビオアレスリン、ビオエタノメトリン、ビオペルメトリン、ビオレスメトリン、トランスペルメトリン、エンペントリン、フェンフルトリン、フェンピリトリン、フルブロシトリネート、フルフェンプロックス、フルメトリン、メトフルトリン、フェノトリン、プロトリフェンブト、ピレスメトリン、テラレトリン；
（４）成長調節物質：
(a)キチン合成阻害剤：クロルフルアズロン、ジフルベンズロン、フルシクロクスロン、フルフェノクスロン、ヘキサフルムロン、ルフェヌロン、ノバルロン、テフルベンズロン、トリフルムロン、ビストリフルロン、ノビフルムロン、ブプロフェジン、ヘキシチアゾクス、エトキサゾール、クロフェンテジン、フルアズロン、ペンフルロン；
(b)エクジソンアンタゴニスト：ハロフェノジド、メトキシフェノジド、テブフェノジド、クロマフェノジド、アザジラクチン；
(c)幼若ホルモン様物質：ピリプロキシフェン、メトプレン、ジオフェノラン、エポフェノナン、ハイドロプレン、キノプレン、トリプレン；
(d)脂質生合成阻害剤：スピロジクロフェン、スピロメシフェン、スピロテトラマト、フロニカミド；
（５）ニコチン受容体アゴニスト／アンタゴニスト化合物：アセタミプリド、クロチアニジン、ジノテフラン、イミダクロプリド、ニテンピラム、チアクロプリド、チアメトキサム、ニチアジン、ニコチン、ベンスルタップ、カルタップ、フルピラジフロン；
（６）GABAアンタゴニスト化合物：
(a)アセトプロール、エチプロール、フィプロニル、バニリプロール、ピラフルプロール、ピリプロール；
(b)有機塩素系：カンフェクロル、クロルデン、エンドスルファン、HCH、γ－HCH、ヘプタクロル、メトキシクロル；
（７）大環状ラクトン殺虫剤：アバメクチン、エマメクチン安息香酸塩、ミルベメクチン、レピメクチン、スピノサド、イベルメクチン、セラメクチン、ドラメクチン、エピノメクチン、モキシデクチン；
（８）METI I化合物：フェナザキン、ピリダベン、テブフェンピラド、トルフェンピラド、フルフェネリム、ヒドラメチルノン、フェンピロキシメート、ピリミジフェン、ジコホル；
（９）METI IIおよびIII化合物：アセキノシル、フルアクリピリム、ロテノン；
（１０）脱共役剤化合物：クロルフェナピル、ビナパクリル、ジノブトン、ジノカップ、DNOC； Insecticides, acaricides, nematicides, soil insecticides, anthelmintics:
(1) Organic (thio) phosphates: acephate, azamethiphos, azinephos methyl, azinephos ethyl, bromophos ethyl, bromfenbinphos, BRP, chlorpyrifos, chlorpyrifos methyl, chlorpyrifos ethyl, chlorfenvinphos, kazusafos, Carbophenothione, chloroethoxyphos, chlormefos, coumaphos, cyanophenphos, cyanophos, CYAP, diazinon, dichlorvos, dicrotophos, dimethoate, disulfotone, dimeton-S-methyl, dimethylvinphos, dimeton-S-methylsulfone, diariphos, diazinon , Diclofenthion, dioxabenzophos, disulfoton, ethion, etoprophos, etrimphos, EPN, phenamiphos, fenitrothion, fenthion, phensulfothio , Flupyrazophos, phonophos, formothione, phosmethylan, heptenophos, isazophos, iodofenphos, isofenphos, isoxathione, iprobenphos, malathion, mevinphos, methamidophos, methidathion, monocrotophos, mecarbam, methalyphos, nared, ometoate, oxydimethone parathione , Parathion methyl, phentoate, hosalon, phosmet, phosphamidone, folate, phoxime, pyrimifos methyl, pyrimifos ethyl, propenophos, prothiophos, phosthiazate, phosphocarb, propaphos, propetamphos, protoate, pyridafenthion, pyracrophos, quinalphos, sulthiote, sulfophos , Tetrachlorbinphos, ter Host, triazophos, trichlorfon, tebupirimfos, temephos, thiometon, vamidothion;
(2) Carbamate series: alanic carb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, phenoxycarb, phenothiocarb, methiocarb, mesomil, oxamyl, pirimicurve, propoxyl, thiodicarb, triazamate, etiofencarb, MPPC, MPC , MTMC, pyridafenthion, furiothiocarb, XMC, aldoxicarb, arixicarb, aminocarb, bendiocarb, bufencarb, butacarb, butcarboxyme, butoxycarboxyme, cloetocarb, dimethylane, formethanate, isoprocarb, metam sodium, metolcarb, promecarb Fanox, Trimetacarb, Xylylcarb;
(3) Pyrethroids: alletrin, bifenthrin, cyfluthrin, beta cyfluthrin, cyhalothrin, lambda cyhalothrin, ciphenothrin, cypermethrin, alpha cypermethrin, beta cypermethrin, zeta cypermethrin, deltamethrin, esfenvalerate, eth Fenprox, fenpropatoline, fenvalerate, imiprothrin, permethrin, praretrin, pyrethrin, pyrethrin I, pyrethrin II, resmethrin, silafluophene, fulvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, cyclomethrin, promethrin , Halfenprox, flucitrinate, bioareslin, bioethanomethrin, bio Rumetorin, Bioresmethrin, trans permethrin, empenthrin, fenfluthrin Trinh, Fen pyridinium Trinh, full Bro shea tri sulphonate, full Fen flufenprox, flumethrin, metofluthrin, phenothrin, protrifenbute, pyresmethrin, terallethrin;
(4) Growth regulator:
(a) Chitin synthesis inhibitor: chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, nobarulone, teflubenzuron, triflumuron, bistrifluron, nobiflumuron, buprofezin, hexithiazox, etoxazole, clofente Gin, fluazuron, penfluron;
(b) ecdysone antagonists: halofenozide, methoxyphenozide, tebufenozide, chromafenozide, azadirachtin;
(c) Juvenile hormone-like substances: pyriproxyfen, methoprene, geophenolan, epofenanane, hydroprene, quinoprene, triprene;
(d) Lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat, flonicamid;
(5) Nicotine receptor agonist / antagonist compounds: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, nithiazine, nicotine, bensultap, cartap, flupiradiflon;
(6) GABA antagonist compound:
(a) acetoprole, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole;
(b) Organochlorine-based: camphechlor, chlordane, endosulfan, HCH, γ-HCH, heptachlor, methoxychlor;
(7) Macrocyclic lactone insecticides: abamectin, emamectin benzoate, milbemectin, lepimectin, spinosad, ivermectin, selamectin, doramectin, epinomectin, moxidectin;
(8) METI I compounds: phenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim, hydramethylnon, fenpyroximate, pyrimidifen, dicophor;
(9) METI II and III compounds: acequinosyl, fluacrylpyrim, rotenone;
(10) Uncoupler compounds: chlorfenapyr, binapacryl, dinobutone, dinocup, DNOC;
（１１）酸化的リン酸化阻害剤化合物：シヘキサチン、ジアフェンチウロン、フェンブタチン・オキシド、プロパルギット、アゾシクロチン；
（１２）脱皮かく乱化合物：シロマジン；
（１３）混合機能オキシダーゼ阻害剤化合物：ピペロニルブトキシド；
（１４）ナトリウムチャネル遮断剤化合物：インドキサカルブ、メタフルミゾン；
（１５）微生物農薬：BT剤、昆虫病原ウイルス剤、昆虫病原糸状菌剤、線虫病原糸状菌剤；バチルス属種、白きょう病菌、黒きょう病菌、ペキロマイセス属種、チューリンギエンシン、バーティシリウム属種；
（１６）ラトロフィリン受容体作用薬：デプシペプチド、環状デプシペプチド、24員環状デプシペプチド、エモデプシド；
（１８）オクトパミン性作用薬：アミトラズ；
（１９）リアノジン誘導体作用薬：フルベンジアミド、クロラントラニリプロール、シアントラリニプロール； (11) Oxidative phosphorylation inhibitor compounds: cyhexatin, diafenthiuron, phenbutatin oxide, propargite, azocyclotin;
(12) molting disrupting compound: cyromazine;
(13) Mixed function oxidase inhibitor compound: piperonyl butoxide;
(14) Sodium channel blocker compounds: indoxacarb, metaflumizone;
(15) Microbial pesticides: BT agent, entomopathogenic virus agent, entomopathogenic fungus agent, nematode pathogenic fungus agent; Bacillus spp. Lilium species;
(16) Latrophilin receptor agonist: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside;
(18) Octopaminergic agent: Amitraz;
(19) Ryanodine derivative agonist: fulvendiamide, chlorantraniliprole, cyantraliniprol;
（２０）マグネシウム刺激性ATPアーゼの阻害薬：チオシクラム、チオスルタップ、ネライストキシン；
（２１）摂食阻害薬：ピメトロジン；
（２２）ダニ成長阻害薬：クロフェンテジン、エトキサゾール；
（２３）その他のもの：ベンクロチアズ、ビフェナゼート、ピリダリル、硫黄、シエノピラフェン、シフルメトフェン、アミドフルメット、テトラジホン、クロルジメホルム、1,3－ジクロロプロペン、DCIP、フェニソブロモレート、ベンゾメート、メタアルデヒド、スピネトラム、ピリフルキナゾン、ベンゾキシメート、ブロモプロピレート、キノメチオネート、クロルベンジレート、クロルピクリン、クロチアゾベン、ジシクラニル、フェノキサクリム、フェントリファニル、フルベンジミン、フルフェンジン、ゴシップルア、ジャポニルア、メトキサジアゾン、石油、オレイン酸カリウム、スルフルラミド、テトラスル、トリアラセン；
（２４）駆虫剤：
(a)ベンズイミダゾール系：フェンベンダゾール、アルベンダゾール、トリクラベンダゾール、オキシベンダゾール；
(b)サリチルアニリド系：クロサンテル、オキシクロザニド；
(c)置換フェノール系：ニトロキシニル；
(d)ピリミジン系：ピランテル；
(e)イミダゾチアゾール系：レバミソール；
(f)テトラヒドロピリミジン：プラジカンテル；
(g)その他の駆虫薬：シクロジエン、リアニア、クロルスロン、メトロニダゾール； (20) Inhibitors of magnesium-stimulated ATPase: thiocyclam, thiosultap, nereistoxin;
(21) antifeedant: pymetrozine;
(22) Tick growth inhibitor: clofentezin, etoxazole;
(23) Others: Benclothiaz, Bifenazate, Pyridalyl, Sulfur, Sienopyraphene, Ciflumethofene, Amidoflumet, Tetradiphone, Chlordimeform, 1,3-Dichloropropene, DCIP, Phenisobromolate, Benzomate, Metaaldehyde, Spinetram, Pyrifluquinazone, Benzo Ximate, bromopropyrate, quinomethionate, chlorbenzilate, chloropicrin, clothiazoben, dicyclanyl, phenoxacrime, fentriphanyl, flubenzimine, flufenzine, gossip lure, japonyla, methoxadiazone, petroleum, potassium oleate, sulfluramide, tetrasul, trialacene;
(24) Anthelmintic:
(a) benzimidazole series: fenbendazole, albendazole, triclabendazole, oxybendazole;
(b) Salicylanilide series: closantel, oxyclozanide;
(c) substituted phenol type: nitroxinyl;
(d) pyrimidine series: pyrantel;
(e) imidazothiazole series: levamisole;
(f) tetrahydropyrimidine: praziquantel;
(g) Other anthelmintic drugs: cyclodiene, riania, chlorthrone, metronidazole;
植物生長調節剤：
アブシジン酸、インドール酪酸、ウニコナゾール、エチクロゼート、エテホン、クロキシホナック、クロルメコート、クロレラ抽出液、過酸化カルシウム、シアナミド、ジクロルプロップ、ジベレリン、ダミノジッド、デシルアルコール、トリネキサパックエチル、メピコートクロリド、パクロブトラゾール、パラフィンワックス、ピペロニルブトキシド、ピラフルフェンエチル、フルルプリミドール、プロヒドロジャスモン、プロヘキサジオンカルシウム塩、ベンジルアミノプリン、ペンディメタリン、ホルクロルフェニュロン、マレイン酸ヒドラジドカリウム、１－ナフチルアセトアミド、4-CPA、MCPB、コリン、硫酸オキシキノリン、エチクロゼート、ブトルアリン、1-メチルシクロプロペン、アビグリシン塩酸塩； Plant growth regulator:
Abscisic acid, indole butyric acid, uniconazole, etiquelozate, etephone, cloxiphonac, chlormecote, chlorella extract, calcium peroxide, cyanamide, dichlorprop, gibberellin, daminozide, decyl alcohol, trinexapac ethyl, mepicoat chloride, pack Lobutrazole, paraffin wax, piperonyl butoxide, pyraflufenethyl, flurprimidol, prohydrojasmon, prohexadione calcium salt, benzylaminopurine, pendimethalin, forchlorphenuron, potassium maleate hydrazide, 1-naphthyl Acetamide, 4-CPA, MCPB, choline, oxyquinoline sulfate, ethiclozate, butorualine, 1-methylcyclopropene, abiglycine hydrochloride;
　次に、実施例を挙げて本発明を更に詳細に説明するが、本発明は以下の実施例により何ら限定されることはない。 Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to the following examples.
実施例１
　８－フルオロ－３－（３－フルオロ－２－（プロパン－２－スルフィニル）－フェノキシ）－キノリン〔8-fluoro-3-[3-fluoro-2-(propane-2-sulfinyl)-phenoxy]-
quinoline〕の合成（化合物番号1-13）
　５０ｍＬフラスコに、８－フルオロ－３－キノリノール０．３７ｇ（２．２７ｍｍｏｌ)およびＮ，Ｎ－ジメチルホルムアミド１０ｍＬを容れた。これに、１，３－ジフルオロ－２－（プロパン－２－スルホニル）ベンゼン０．５０ｇ（２．２７ ｍｍｏｌ)および炭酸カリウム ０．５０g（２．２７ｍｍｏｌ)を加えた。その後、１００℃にて３時間加熱した。次いで室温に冷却した。反応混合物を水に注ぎ、酢酸エチルで抽出した。有機層をブラインで洗浄し、硫酸マグネシウムで乾燥させた。濾過、次いで濃縮した。得られた反応混合物を山善カラムで精製した。８－フルオロ－３－（３－フルオロ－２－（プロパン－２－スルホニル）－フェノキシ）－キノリンが０．４２ｇ（５１％）得られた。 Example 1
8-Fluoro-3- (3-fluoro-2- (propane-2-sulfinyl) -phenoxy) -quinoline [8-fluoro-3- [3-fluoro-2- (propane-2-sulfinyl) -phenoxy]-
quinoline] (Compound No. 1-13)
A 50 mL flask was charged with 0.37 g (2.27 mmol) of 8-fluoro-3-quinolinol and 10 mL of N, N-dimethylformamide. To this was added 0.50 g (2.27 mmol) of 1,3-difluoro-2- (propane-2-sulfonyl) benzene and 0.50 g (2.27 mmol) of potassium carbonate. Then, it heated at 100 degreeC for 3 hours. It was then cooled to room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. Filtration followed by concentration. The resulting reaction mixture was purified with a Yamazen column. 0.42 g (51%) of 8-fluoro-3- (3-fluoro-2- (propane-2-sulfonyl) -phenoxy) -quinoline was obtained.
実施例２
　８－フルオロ－３－（３－フルオロ－２－ニトロ－フェノキシ）－キノリンの合成〔8-fluoro-3-(3-fluoro-2-nitro-phenoxy)-quinoline〕の合成（化合物番号2-2）
　２００ｍＬフラスコに、８－フルオロ－３－キノリノール５．１３ｇ（３１．４２ｍｍｏｌ)およびアセトニトリル１００ｍＬを容れた。これに、市販の１，３－ジフルオロ－２－ニトロベンゼン５．００ｇ（３１．４２ｍｍｏｌ)、および炭酸カリウム８．６８ｇ（６２．８４ｍｍｏｌ)を加えた。その後、２０時間加熱還流した。室温に冷却した。濾過、次いで濃縮した。得られた反応混合物をシリカゲルカラムで精製した。８－フルオロ－３－（３－フルオロ－２－ニトロ－フェノキシ）－キノリンが６．０３ｇ（６３％）得られた。 Example 2
Synthesis of 8-fluoro-3- (3-fluoro-2-nitro-phenoxy) -quinoline [Compound No. 2-2 )
A 200 mL flask was charged with 5.13 g (31.42 mmol) of 8-fluoro-3-quinolinol and 100 mL of acetonitrile. To this, 5.00 g (31.42 mmol) of commercially available 1,3-difluoro-2-nitrobenzene and 8.68 g (62.84 mmol) of potassium carbonate were added. Thereafter, the mixture was heated to reflux for 20 hours. Cooled to room temperature. Filtration followed by concentration. The resulting reaction mixture was purified on a silica gel column. This gave 6.03 g (63%) of 8-fluoro-3- (3-fluoro-2-nitro-phenoxy) -quinoline.
実施例３
　２－フルオロ－６－（８－フルオロ－キノリン－３－イルオキシ）－フェニルアミン〔2-fluoro-6-(8-fluoro-quinolin-3-yloxy)-phenylamine〕の合成（化合物番号2-5）
　５００ｍＬフラスコに、８－フルオロ－３－（３－フルオロ－２－ニトロ－フェノキシ）－キノリン６．０３ｇ（１９．９４ｍｍｏｌ）および酢酸エチル１００ｍＬを容れた。これに、１０％Ｐｄ／Ｃ　１．０６ｇを加え、水素雰囲気下、室温で２４時間攪拌した。濾過、次いで濃縮した。得られた反応混合物をシリカゲルカラムで精製した。２－フルオロ－６－（８－フルオロ－キノリン－３－イルオキシ）－フェニルアミンが４．３９ｇ（８１％）得られた。 Example 3
Synthesis of 2-fluoro-6- (8-fluoro-quinolin-3-yloxy) -phenylamine [Compound No. 2-5]
A 500 mL flask was charged with 6.03 g (19.94 mmol) of 8-fluoro-3- (3-fluoro-2-nitro-phenoxy) -quinoline and 100 mL of ethyl acetate. 10% Pd / C 1.06g was added to this, and it stirred at room temperature for 24 hours under hydrogen atmosphere. Filtration followed by concentration. The resulting reaction mixture was purified on a silica gel column. 4.39 g (81%) of 2-fluoro-6- (8-fluoro-quinolin-3-yloxy) -phenylamine was obtained.
実施例４
　トリフルオロ－Ｎ－（２－フルオロ－６－（８－フルオロ－キノリン－３－イルオキシ）フェニル）－メタンスルホンアミド〔trifluoro-N-[2-fluoro-6-(8-fluoro-
quinolin-3-yloxy)-phenyl]-methanesulfonamide〕の合成（化合物番号2-20）
　５０ｍＬフラスコに、２－フルオロ－６－（８－フルオロ－キノリン－３－イルオキシ）－フェニルアミン０．３１ｇ（１．１３ｍｍｏｌ）およびジクロロメタン１０ｍＬを容れた。これを０℃に冷却した。次いで、トリフルオロメタンスルホン酸無水物０．４８ｇ（１．７０ｍｍｏｌ）を加え、室温で２０時間攪拌した。反応混合物を水に注ぎ、酢酸エチルで抽出した。有機層をブラインで洗浄し、硫酸マグネシウムで乾燥させた。濾過、次いで濃縮した。得られた反応混合物を山善カラムで精製した。トリフルオロ－Ｎ－（２－フルオロ－６－（８－フルオロ－キノリン－３－イルオキシ）フェニル）－メタンスルホンアミドが０．３０ｇ（６５％）得られた。 Example 4
Trifluoro-N- (2-fluoro-6- (8-fluoro-quinolin-3-yloxy) phenyl) -methanesulfonamide [trifluoro-N- [2-fluoro-6- (8-fluoro-
quinolin-3-yloxy) -phenyl] -methanesulfonamide] (Compound No. 2-20)
A 50 mL flask was charged with 0.31 g (1.13 mmol) 2-fluoro-6- (8-fluoro-quinolin-3-yloxy) -phenylamine and 10 mL dichloromethane. This was cooled to 0 ° C. Next, 0.48 g (1.70 mmol) of trifluoromethanesulfonic anhydride was added, and the mixture was stirred at room temperature for 20 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. Filtration followed by concentration. The resulting reaction mixture was purified with a Yamazen column. 0.30 g (65%) of trifluoro-N- (2-fluoro-6- (8-fluoro-quinolin-3-yloxy) phenyl) -methanesulfonamide was obtained.
実施例５
　トリフルオロ－Ｎ－（２－フルオロ－６－（８－フルオロ－キノリン－３－イルオキシ）－フェニル）－Ｎ－メチル－メタンスルホンアミド〔trifluoro-N-[2-
fluoro-6-(8-fluoro-quinolin-3-yloxy)-phenyl]-N-methyl-methanesulfonamide〕の合成（化合物番号2-21）
　５０ｍＬフラスコに、トリフルオロ－Ｎ－（２－フルオロ－６－（８－フルオロ－キノリン－３－イルオキシ）フェニル）－メタンスルホンアミド０．１５ｇ（０．３７ｍｍｏｌ）およびアセトン１０ｍＬを容れた。これに、ヨウ化メチル０．１５ｇ（０．７４ｍｍｏｌ）および炭酸カリウム０．１０ｇ（０．７４ｍｍｏｌ）を加え、室温で２４時間攪拌した。反応混合物を濾過、次いで濃縮した。濃縮物をシリカゲルカラムで精製した。トリフルオロ－Ｎ－（２－フルオロ－６－（８－フルオロ－キノリン－３－イルオキシ）－フェニル）－Ｎ－メチル－メタンスルホンアミドが０．１１ｇ（７３％）得られた。 Example 5
Trifluoro-N- (2-fluoro-6- (8-fluoro-quinolin-3-yloxy) -phenyl) -N-methyl-methanesulfonamide [trifluoro-N- [2-
Synthesis of fluoro-6- (8-fluoro-quinolin-3-yloxy) -phenyl] -N-methyl-methanesulfonamide] (Compound No. 2-21)
A 50 mL flask was charged with 0.15 g (0.37 mmol) of trifluoro-N- (2-fluoro-6- (8-fluoro-quinolin-3-yloxy) phenyl) -methanesulfonamide and 10 mL of acetone. To this, 0.15 g (0.74 mmol) of methyl iodide and 0.10 g (0.74 mmol) of potassium carbonate were added and stirred at room temperature for 24 hours. The reaction mixture was filtered and then concentrated. The concentrate was purified on a silica gel column. 0.11 g (73%) of trifluoro-N- (2-fluoro-6- (8-fluoro-quinolin-3-yloxy) -phenyl) -N-methyl-methanesulfonamide was obtained.
実施例６
　５－フルオロ－２－[３－フルオロ－２－（プロパン－２－スルホニル）フェノキシ]キノキサリン（　5-fluoro-2-[3-fluoro-2-(propane-2-sulfonyl)phenoxy]
quinoxaline　）の合成（化合物番号ａ1-10） Example 6
5-fluoro-2- [3-fluoro-2- (propane-2-sulfonyl) phenoxy] quinoxaline (5-fluoro-2- [3-fluoro-2- (propane-2-sulfonyl) phenoxy]
quinoxaline) (Compound No. a1-10)
（工程１）５－フルオロ－２－（３－フルオロ－２－イソプロピルスルファニルフェノキシ）キノキサリン（5-fluoro-2-(3-fluoro-2-isopropylsulfanylphenoxy)-
quinoxaline）の合成
　２－クロロ－５－フルオロキノキサリン（2-chloro-5-fluoroquinoxaline）０．１４ｇ（０．７５ｍｍｏｌ）及び３－フルオロ－２－イソプロピルスルファニルフェノール（3-fluoro-2-isopropylsulfanylphenol）０．１４ｇ（０．７５ｍｍｏｌ）のジメチルホルムアミド溶液１０ｍＬに、炭酸カリウム０．１２ｇ（０．９０ｍｍｏｌ）を室温で加えた。次いで、１００℃に昇温し、４時間撹拌した。室温まで冷却し、その後、前記溶液を酢酸エチル１００ｍＬと水１００ｍＬの入った分液ロートに注加し、水層と有機層とに分離した。水層を酢酸エチル１００ｍＬで抽出して有機層を分離した。得られた有機層を混ぜ合わせ、それをブライン５０ｍＬで洗浄し、硫酸マグネシウムで乾燥した。次いで、それを濾過し、減圧下で溶媒を留去した。得られた残渣を山善カラムクロマトグラフィー（L）（ヘキサン：酢酸エチル）で精製して目的物5-fluoro-2-(3-fluoro-2-isopropylsulfanyl
phenoxy)-quinoxaline０．２３ｇ（９２％）を得た。
　２－クロロ－５－フルオロキノキサリンは、J.Med.Chem.1981,24,93-101に記載の製造方法を参考にして合成した。
　また、３－フルオロ－２－イソプロピルスルファニルフェノールは、ＷＯ２００３／０９１２３９に記載の製造方法を参考にして合成した。 (Step 1) 5-Fluoro-2- (3-fluoro-2-isopropylsulfanylphenoxy) quinoxaline (5-fluoro-2- (3-fluoro-2-isopropylsulfanylphenoxy)-
Synthesis of quinoxaline) 0.14 g (0.75 mmol) of 2-chloro-5-fluoroquinoxaline and 3-fluoro-2-isopropylsulfanylphenol To 10 mL of 14 g (0.75 mmol) of dimethylformamide solution, 0.12 g (0.90 mmol) of potassium carbonate was added at room temperature. Subsequently, it heated up at 100 degreeC and stirred for 4 hours. After cooling to room temperature, the solution was poured into a separatory funnel containing 100 mL of ethyl acetate and 100 mL of water, and separated into an aqueous layer and an organic layer. The aqueous layer was extracted with 100 mL of ethyl acetate and the organic layer was separated. The resulting organic layers were combined and it was washed with 50 mL brine and dried over magnesium sulfate. It was then filtered and the solvent was distilled off under reduced pressure. The resulting residue was purified by Yamazen column chromatography (L) (hexane: ethyl acetate) to give the desired product 5-fluoro-2- (3-fluoro-2-isopropylsulfanyl
0.23 g (92%) of phenoxy) -quinoxaline was obtained.
2-Chloro-5-fluoroquinoxaline was synthesized with reference to the production method described in J. Med. Chem. 1981, 24, 93-101.
Further, 3-fluoro-2-isopropylsulfanylphenol was synthesized with reference to the production method described in WO2003 / 091239.
（工程２）５－フルオロ－２－[３－フルオロ－２－（プロパン－２－スルホニル）フェノキシ]キノキサリンの合成（化合物番号ａ1-10）
　5-fluoro-2-(3-fluoro-2-isopropylsulfanylphenoxy)-quinoxaline０．２３ｇ（０．６９ｍｍｏｌ）を２-プロパノール４ｍＬ：水２ｍＬの混合溶媒に溶解させた。これにオキソン〔デュポン社製ペルオキシ一硫酸カリウム〕０．９８ｇ（１．５８ｍｍｏｌ）を加え、室温で２０時間攪拌した。前記溶液を酢酸エチル１００ｍＬと水１００ｍＬの入った分液ロートに注加し、水層と有機層とに分離した。水層を酢酸エチル１００ｍＬで抽出して有機層を分離した。得られた有機層を混ぜ合わせた。それをブライン５０ｍＬで洗浄し、硫酸マグネシウムで乾燥した。次いで、それを濾過し、減圧下で溶媒を留去した。得られた残渣を山善カラムクロマトグラフィー（Ｌ）（ヘキサン：酢酸エチル）で精製して目的物5-fluoro-2-[3-
fluoro-2-(propane-2-sulfonyl)phenoxy]quinoxaline０．１９ｇ（７６％）を得た。 (Step 2) Synthesis of 5-fluoro-2- [3-fluoro-2- (propane-2-sulfonyl) phenoxy] quinoxaline (Compound No. a1-10)
0.23 g (0.69 mmol) of 5-fluoro-2- (3-fluoro-2-isopropylsulfanylphenoxy) -quinoxaline was dissolved in a mixed solvent of 4 mL of 2-propanol: 2 mL of water. To this was added 0.98 g (1.58 mmol) of oxone [DuPont Peroxymonosulfate] and stirred at room temperature for 20 hours. The solution was poured into a separatory funnel containing 100 mL of ethyl acetate and 100 mL of water, and separated into an aqueous layer and an organic layer. The aqueous layer was extracted with 100 mL of ethyl acetate and the organic layer was separated. The obtained organic layer was mixed. It was washed with 50 mL brine and dried over magnesium sulfate. It was then filtered and the solvent was distilled off under reduced pressure. The obtained residue was purified by Yamazen column chromatography (L) (hexane: ethyl acetate) to give the desired product 5-fluoro-2- [3-
0.19 g (76%) of fluoro-2- (propane-2-sulfonyl) phenoxy] quinoxaline was obtained.
実施例７
６－フルオロ－２－[３－クロロ－２－（プロパン－２－スルホニル）フェノキシ]キノキサリン（6-Fluoro-2-[3-chloro-2-(propane-2-sulfonyl)phenoxy]
quinoxaline）の合成（化合物番号ａ1-16） Example 7
6-Fluoro-2- [3-chloro-2- (propane-2-sulfonyl) phenoxy]
quinoxaline) (Compound No. a1-16)
（工程１）６－フルオロ－３，４－ジヒドロ－１Ｈ－キノキサリン－２－オンの合成
２，４－ジフルオロニトロベンゼン４０．０ｇを４００ｍＬのアセトニトリルに溶解し、グリシンエチルエステル塩酸塩３５．１ｇ、ジイソプロピルエチルアミン３２．３ｇを加え１５時間加熱還流を行った。反応液を室温まで冷却後、減圧下で容量が１／３程度になるまで濃縮した後、水に加え酢酸エチルで抽出した。抽出液を飽和食塩水で洗浄し、硫酸マグネシウムで乾燥させ、減圧下で溶媒を留去し、得られた結晶をｎ－ヘキサンで洗浄した。この結晶４０ｇを４００ｍＬのメタノールに溶解し、１０％パラジウム炭素１．８ｇを加え、水素雰囲気下１８時間攪拌した。セライトろ過後減圧濃縮し、残渣をシリカゲルカラムクロマトグラフィーで精製することで、６－フルオロ－３，４－ジヒドロ－１Ｈ－キノキサリン－２－オン２３．９ｇを得た。ＮＭＲ(300MHz, CDCl3)δは以下の通りであった。
1H-NMR (400MHz, CDCl3) d 3.87 (d, 2H), 4.37 (bs, 1H), 6.30-6.35 (m, 2 H), 6.62 (d, 1H), 9.37 (bs, 1H). (Step 1) Synthesis of 6-fluoro-3,4-dihydro-1H-quinoxalin-2-one 40.0 g of 2,4-difluoronitrobenzene was dissolved in 400 mL of acetonitrile, 35.1 g of glycine ethyl ester hydrochloride, diisopropyl 32.3 g of ethylamine was added and the mixture was heated to reflux for 15 hours. The reaction solution was cooled to room temperature, concentrated under reduced pressure to a volume of about 1/3, added to water, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained crystals were washed with n-hexane. 40 g of this crystal was dissolved in 400 mL of methanol, 1.8 g of 10% palladium carbon was added, and the mixture was stirred under a hydrogen atmosphere for 18 hours. After filtration through celite and concentration under reduced pressure, the residue was purified by silica gel column chromatography to obtain 23.9 g of 6-fluoro-3,4-dihydro-1H-quinoxalin-2-one. NMR (300 MHz, CDCl 3 ) δ was as follows.
1 H-NMR (400MHz, CDCl 3 ) d 3.87 (d, 2H), 4.37 (bs, 1H), 6.30-6.35 (m, 2 H), 6.62 (d, 1H), 9.37 (bs, 1H).
（工程２）２－クロロ－６－フルオロキノキサリンの合成
６－フルオロ－３，４－ジヒドロ－１Ｈ－キノキサリン－２－オン２３．９ｇ、二酸化マンガン３７．６ｇをベンゼン３００ｍｌに加え、ジーンスターク装置で脱水を行いながら６時間加熱還流を行った。反応液を室温まで冷却後、セライトろ過を行い、不溶物をアセトン１Ｌ、酢酸エチル１Ｌで洗浄した。ろ液を合わせて減圧下で溶媒を留去し、残渣を少量の酢酸エチル、アセトンで順次洗浄し、１．７ｇの結晶を得た。得られた結晶全量をオキシ塩化リン３０ｍＬに加え、６時間加熱還流を行い、反応液を室温まで冷却後、過剰のオキシ塩化リンを減圧留去した。得られた残渣に氷水を加え、飽和重曹溶液にて中和を行い、酢酸エチルで抽出した。抽出液を飽和食塩水で洗浄し、硫酸マグネシウムで乾燥させ、減圧下で溶媒を留去した。得られた残渣をシリカゲルカラムクロマトグラフィーで精製することにより、２－クロロ－６－フルオロキノキサリン１．６７ｇを得た。ＮＭＲ(300MHz, CDCl3)δは以下の通りであった。
1H-NMR (400MHz, CDCl3) d 7.58 (m, 1H), 7.75 (m, 1H), 8.03 (m, 1 H), 8.78 (s, 1H). (Step 2) Synthesis of 2-chloro-6-fluoroquinoxaline 23.9 g of 6-fluoro-3,4-dihydro-1H-quinoxalin-2-one and 37.6 g of manganese dioxide were added to 300 ml of benzene, The mixture was heated to reflux for 6 hours while dehydrating. The reaction solution was cooled to room temperature, filtered through Celite, and the insoluble material was washed with 1 L of acetone and 1 L of ethyl acetate. The filtrates were combined, the solvent was distilled off under reduced pressure, and the residue was washed successively with a small amount of ethyl acetate and acetone to obtain 1.7 g of crystals. The total amount of crystals obtained was added to 30 mL of phosphorus oxychloride, heated under reflux for 6 hours, and the reaction solution was cooled to room temperature, and then excess phosphorus oxychloride was distilled off under reduced pressure. Ice water was added to the resulting residue, neutralized with a saturated sodium bicarbonate solution, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.67 g of 2-chloro-6-fluoroquinoxaline. NMR (300 MHz, CDCl 3 ) δ was as follows.
1 H-NMR (400MHz, CDCl 3 ) d 7.58 (m, 1H), 7.75 (m, 1H), 8.03 (m, 1 H), 8.78 (s, 1H).
（工程３）３－クロロ－２－（プロパン－２－スルホニル）フェノールの合成
２，６－ジクロロチオフェノール１５０．７ｇ、ヨウ化イソプロピル１７１．７ｇを２．５Lのアセトニトリルに溶解し、炭酸カリウム１７４．５ｇを加えて３時間加熱還流を行った。反応液を室温まで冷却後、溶媒を減圧留去し、残渣に水を加え酢酸エチルで抽出した。抽出液を硫酸マグネシウムで乾燥させ、減圧下で溶媒を留去し、イソプロピル　２，６－ジクロロフェニル　スルフィドの粗結晶２０４．３gを得た。この粗結晶１８０．８gをジクロロメタン２．５Lに溶解し、m-クロロ過安息香酸（アルドリッチ製max７７％含有）４２１．４ｇを加えて室温で５時間攪拌した。反応溶液に飽和重曹水を加え１時間攪拌した後、クロロホルムと水を加え、分液を行った。有機層をさらに飽和重曹水で洗浄後、硫酸マグネシウムで乾燥させ、減圧下で溶媒を留去し、イソプロピル　２，６－ジクロロフェニル　スルホンの粗結晶２２２．９ｇを得た。この粗結晶２０７．０ｇを２Lのジメチルホルムアミドに溶解し、２－（メタンスルホニル）エタノール１０１．５ｇを加えた後、０℃攪拌下で水素化ナトリウム（６０％オイルディスパージョン）９８．１ｇを少しずつ加えた。反応溶液を室温で２時間攪拌した後、１N塩酸溶液で中和し、酢酸エチルで抽出した。抽出液を硫酸マグネシウムで乾燥させ、減圧下で溶媒を留去した。得られた残渣をシリカゲルカラムクロマトグラフィーで精製することにより３－クロロ－２－（プロパン－２－スルホニル）フェノール１２０．７ｇを得た。ＮＭＲ(300MHz, CDCl3)δは以下の通りであった。
1H-NMR (400MHz, CDCl3) d 1.37 (d, 6H), 3.85 (sep, 1H), 6.93 (d, 1 H), 7.01 (d, 1H), 7.37 (t, 1H) , 10.44 (s, 1H). (Step 3) Synthesis of 3-chloro-2- (propane-2-sulfonyl) phenol 150.7 g of 2,6-dichlorothiophenol and 171.7 g of isopropyl iodide were dissolved in 2.5 L of acetonitrile, and potassium carbonate 174 .5 g was added and heated to reflux for 3 hours. The reaction mixture was cooled to room temperature, the solvent was evaporated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 204.3 g of crude crystals of isopropyl 2,6-dichlorophenyl sulfide. 180.8 g of this crude crystal was dissolved in 2.5 L of dichloromethane, and 421.4 g of m-chloroperbenzoic acid (containing 77% max from Aldrich) was added and stirred at room temperature for 5 hours. Saturated aqueous sodium hydrogen carbonate was added to the reaction solution and stirred for 1 hour, and then chloroform and water were added to carry out liquid separation. The organic layer was further washed with saturated aqueous sodium hydrogen carbonate and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 222.9 g of crude crystals of isopropyl 2,6-dichlorophenyl sulfone. 207.0 g of this crude crystal was dissolved in 2 L of dimethylformamide, 101.5 g of 2- (methanesulfonyl) ethanol was added, and then 98.1 g of sodium hydride (60% oil dispersion) was slightly added with stirring at 0 ° C. Added one by one. The reaction solution was stirred at room temperature for 2 hours, neutralized with 1N hydrochloric acid solution, and extracted with ethyl acetate. The extract was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 120.7 g of 3-chloro-2- (propane-2-sulfonyl) phenol. NMR (300 MHz, CDCl 3 ) δ was as follows.
1 H-NMR (400MHz, CDCl 3 ) d 1.37 (d, 6H), 3.85 (sep, 1H), 6.93 (d, 1 H), 7.01 (d, 1H), 7.37 (t, 1H), 10.44 (s , 1H).
（工程４）６－フルオロ－２－[３－クロロ－２－（プロパン－２－スルホニル）フェノキシ]キノキサリンの合成
２－クロロ－６－フルオロキノキサリン３５．６４ｇ、３－クロロ－２－（プロパン－２－スルホニル）フェノール４５．８２ｇをジメチルホルムアミド５８６mＬに溶解し、炭酸カリウム３２．３８ｇを加え、１００℃で２４時間攪拌した。反応溶液を室温まで冷却後、水に加え、酢酸エチルで抽出した。抽出液を水洗後、硫酸マグネシウムで乾燥させ、減圧下で溶媒を留去し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することにより６－フルオロ－２－[３－クロロ－２－（プロパン－２－スルホニル）フェノキシ]キノキサリン６１．７ｇ（８３％）を得た。融点；１４４－１４５℃ (Step 4) Synthesis of 6-fluoro-2- [3-chloro-2- (propane-2-sulfonyl) phenoxy] quinoxaline 35.64 g of 2-chloro-6-fluoroquinoxaline, 3-chloro-2- (propane- 2-sulfonyl) phenol (45.82 g) was dissolved in 586 mL of dimethylformamide, 32.38 g of potassium carbonate was added, and the mixture was stirred at 100 ° C. for 24 hours. The reaction solution was cooled to room temperature, added to water, and extracted with ethyl acetate. The extract is washed with water, dried over magnesium sulfate, the solvent is distilled off under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give 6-fluoro-2- [3-chloro-2- (propane). -2-sulfonyl) phenoxy] quinoxaline was obtained 61.7 g (83%). Melting point: 144-145 ° C
　上記の実施例で得られた含窒素ヘテロ環化合物、および上記の実施例のいずれかと同様の手法によって合成することができる含窒素ヘテロ環化合物を、第１表～第８表に示す。
　第１表および第２表中のＲ、(Ｘ１)m、(Ｘ２)ｎ、およびＸは式（１－Ａ）中のそれらを表す。
　第３表中のＲ、(Ｘ１)m、(Ｘ２)ｎ、およびＸは式（１－Ｂ）中のそれらを表す。
　第４表中のＲ、(Ｘ１)m、Ｂ、(Ｘ２)ｎ、Ａ２～Ａ４、およびＸは式（１－Ｃ）中のそれらを表す。
　第５表中のＲ、(Ｘ１)m、Ｂ、(Ｘ２)ｎ、Ａ６、Ａ７、およびＸは式（１－Ｄ）中のそれらを表す。
　第６表中のＲ、(Ｘ１)m、Ｂ、(Ｘ２)ｎ、Ａ３、およびＸは式（１－Ｅ）中のそれらを表す。
　第７表中のＲ、Ｂ、(Ｘ２)ｎ、Ａ３、およびＸは式（１－Ｆ）中のそれらを表す。
　第８表中のＲ、Ｂ、(Ｘ２)ｎ、Ａ３、およびＸは式（１－Ｇ）中のそれらを表す。
　物性の欄には、融点（℃）または屈折率（ｎD）を示す。ここで（ｎD）の上付きの数字は測定温度（℃）を示す。 Tables 1 to 8 show the nitrogen-containing heterocyclic compounds obtained in the above Examples and the nitrogen-containing heterocyclic compounds that can be synthesized by the same method as in any of the above Examples.
R, (X 1 ) m, (X 2 ) n, and X in Tables 1 and 2 represent those in formula (1-A).
R, (X 1 ) m, (X 2 ) n, and X in Table 3 represent those in formula (1-B).
R, (X 1 ) m, B, (X 2 ) n, A 2 to A 4 , and X in Table 4 represent those in formula (1-C).
R, (X 1 ) m, B, (X 2 ) n, A 6 , A 7 , and X in Table 5 represent those in formula (1-D).
R, (X 1 ) m, B, (X 2 ) n, A 3 , and X in Table 6 represent those in formula (1-E).
R, B, (X 2 ) n, A 3 , and X in Table 7 represent those in formula (1-F).
R, B, (X 2 ) n, A 3 , and X in Table 8 represent those in formula (1-G).
In the column of physical properties, melting point (° C.) or refractive index (n D ) is shown. Here, the superscript number of (n D ) indicates the measurement temperature (° C.).
Figure JPOXMLDOC01-appb-C000022
Figure JPOXMLDOC01-appb-C000022
Figure JPOXMLDOC01-appb-T000023
Figure JPOXMLDOC01-appb-T000023
Figure JPOXMLDOC01-appb-T000024
Figure JPOXMLDOC01-appb-T000024
Figure JPOXMLDOC01-appb-T000025
Figure JPOXMLDOC01-appb-T000025
Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-C000027
Figure JPOXMLDOC01-appb-C000027
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000030
Figure JPOXMLDOC01-appb-T000030
Figure JPOXMLDOC01-appb-C000031
Figure JPOXMLDOC01-appb-C000031
Figure JPOXMLDOC01-appb-T000032
Figure JPOXMLDOC01-appb-T000032
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-C000034
Figure JPOXMLDOC01-appb-C000034
Figure JPOXMLDOC01-appb-T000035
Figure JPOXMLDOC01-appb-T000035
Figure JPOXMLDOC01-appb-T000036
Figure JPOXMLDOC01-appb-T000036
Figure JPOXMLDOC01-appb-C000037
Figure JPOXMLDOC01-appb-C000037
Figure JPOXMLDOC01-appb-T000038
Figure JPOXMLDOC01-appb-T000038
Figure JPOXMLDOC01-appb-C000039
Figure JPOXMLDOC01-appb-C000039
Figure JPOXMLDOC01-appb-T000040
Figure JPOXMLDOC01-appb-T000040
Figure JPOXMLDOC01-appb-C000041
Figure JPOXMLDOC01-appb-C000041
Figure JPOXMLDOC01-appb-T000042
Figure JPOXMLDOC01-appb-T000042
　上記の表に示した化合物のうち、物性の欄に＊を記載した化合物について1Ｈ－ＮＭＲ(300MHz, CDCl3)δを測定した。測定結果の一部を以下に示す。
　化合物1-1　：　6.89-7.00 (m, 2H), 7.14-7.17 (m, 2H), 7.43 (d, 1H), 7.51 (t, 1H), 7.59-7.66 (m, 2H), 8.09 (d, 1H), 8.56 (d, 1H).
　化合物1-4　：　7.08 (m, 1H), 7.31-7.34 (m, 2H), 7.41 (m, 1H), 7.48-7.77 (m, 4H), 8.11 (m, 1H), 8.83 (d, 1H).
　化合物1-5　：　5.07 (s, 2H), 7.02 (m, 1H), 7.05-7.23 (m, 8H), 7.32 (d, 1H), 7.47 (m, 1H), 7.57-7.63 (m, 2H), 8.10 (d, 1H), 8.85 (d, 1H).
　化合物1-8　：　1.37 (d, 6H), 2.76 (m, 1H), 7.03 (t, 1H), 7.36-7.63 (m, 5H), 7.71-7.87 (m, 3H), 8.28 (s, 1H), 8.81 (d, 1H).
　化合物1-12　：　1.23 (d, 6H, J = 6.8Hz), 3.54 (m, 1H), 6.89 (m, 1H), 7.05 (m, 1H), 7.29-7.37 (m, 3H), 7.43-7.46 (m, 2H), 8.86 (d, 1H, J = 2.8 Hz)
　化合物1-14　：　3.31 (s, 3H), 7.06 (m, 1H), 7.34-7.42 (m, 2H), 7.48-7.53 (m, 2H), 7.64-7.71 (m, 2H), 8.14 (m, 1H), 8.90 (d, 1H).
　化合物1-17　：　3.40 (s, 3H), 7.01 (m, 1H), 7.3-7.7 (m, 6H), 8.87 (d, 1H).
　化合物1-18　：　2.89 (d, 6H, J = 7.2Hz), 3.67 (m, 1H), 6.87 (m, 1H), 7.11 (m, 1H), 7.36 (m, 1H), 7.49-7.51 (m, 2H), 7.56-7.64 (m 2H), 8.85 (d, 1H, J = 2.8 Hz) Of the compounds shown in the above table, 1 H-NMR (300 MHz, CDCl 3 ) δ was measured for the compounds marked with * in the physical property column. Some of the measurement results are shown below.
Compound 1-1: 6.89-7.00 (m, 2H), 7.14-7.17 (m, 2H), 7.43 (d, 1H), 7.51 (t, 1H), 7.59-7.66 (m, 2H), 8.09 (d, 1H), 8.56 (d, 1H).
Compound 1-4: 7.08 (m, 1H), 7.31-7.34 (m, 2H), 7.41 (m, 1H), 7.48-7.77 (m, 4H), 8.11 (m, 1H), 8.83 (d, 1H) .
Compound 1-5: 5.07 (s, 2H), 7.02 (m, 1H), 7.05-7.23 (m, 8H), 7.32 (d, 1H), 7.47 (m, 1H), 7.57-7.63 (m, 2H) , 8.10 (d, 1H), 8.85 (d, 1H).
Compound 1-8: 1.37 (d, 6H), 2.76 (m, 1H), 7.03 (t, 1H), 7.36-7.63 (m, 5H), 7.71-7.87 (m, 3H), 8.28 (s, 1H) , 8.81 (d, 1H).
Compound 1-12: 1.23 (d, 6H, J = 6.8Hz), 3.54 (m, 1H), 6.89 (m, 1H), 7.05 (m, 1H), 7.29-7.37 (m, 3H), 7.43-7.46 (m, 2H), 8.86 (d, 1H, J = 2.8 Hz)
Compound 1-14: 3.31 (s, 3H), 7.06 (m, 1H), 7.34-7.42 (m, 2H), 7.48-7.53 (m, 2H), 7.64-7.71 (m, 2H), 8.14 (m, 1H), 8.90 (d, 1H).
Compound 1-17: 3.40 (s, 3H), 7.01 (m, 1H), 7.3-7.7 (m, 6H), 8.87 (d, 1H).
Compound 1-18: 2.89 (d, 6H, J = 7.2Hz), 3.67 (m, 1H), 6.87 (m, 1H), 7.11 (m, 1H), 7.36 (m, 1H), 7.49-7.51 (m , 2H), 7.56-7.64 (m 2H), 8.85 (d, 1H, J = 2.8 Hz)
　化合物1-32　：　1.22 (t, 3H, J = 7.2Hz), 1.78 (s, 6H), 4.25 (q, 2H,  J = 7.2Hz), 7.03 (m, 1H), 7.33 (m, 1H), 7.42-7.57 (m, 5H), 8.82 (m, 1H)
　化合物1-35　：　3.14 (s, 3H), 3.96 (q, 2H, J = 8.8 Hz), 6.84 (m, 1H), 7.08 (m, 1H), 7.38 (m, 1H), 7.49-7.55 (m, 3H), 7.65 (m, 1H), 8.84 (d, 1H, J = 2.8 Hz)
　化合物1-90　：　1.43 (d, 6H), 2.73 (s, 3H), 3.79 (sep, 1H), 6.87 (dd, 1H), 7.3-7.5 (m, 4H), 7.61(m, 2H), 8.01( d, 1H)
　化合物2-1　：　7.13 (dd, 1H), 7.31 (m, 1H), 7.5-7.8 (m, 5H), 8.04 (dd, 1H), 7.12 (d, 1H), 8.82 (s, 1H).
　化合物2-7　：　3.31 (s, 3H), 3.73 (s, 3H), 6.92 (m, 1H), 7.04-7.15 (m, 3H), 7.23-7.42 (m, 3H), 8.22 (d, 1H).
　化合物2-11　：　4.28 (s, 4H), 6.71 (dd, 1H), 7.00 (m, 1H), 7.15-7.45 (m, 15H), 8.60 (d, 1H). Compound 1-32: 1.22 (t, 3H, J = 7.2Hz), 1.78 (s, 6H), 4.25 (q, 2H, J = 7.2Hz), 7.03 (m, 1H), 7.33 (m, 1H), 7.42-7.57 (m, 5H), 8.82 (m, 1H)
Compound 1-35: 3.14 (s, 3H), 3.96 (q, 2H, J = 8.8 Hz), 6.84 (m, 1H), 7.08 (m, 1H), 7.38 (m, 1H), 7.49-7.55 (m , 3H), 7.65 (m, 1H), 8.84 (d, 1H, J = 2.8 Hz)
Compound 1-90: 1.43 (d, 6H), 2.73 (s, 3H), 3.79 (sep, 1H), 6.87 (dd, 1H), 7.3-7.5 (m, 4H), 7.61 (m, 2H), 8.01 (d, 1H)
Compound 2-1: 7.13 (dd, 1H), 7.31 (m, 1H), 7.5-7.8 (m, 5H), 8.04 (dd, 1H), 7.12 (d, 1H), 8.82 (s, 1H).
Compound 2-7: 3.31 (s, 3H), 3.73 (s, 3H), 6.92 (m, 1H), 7.04-7.15 (m, 3H), 7.23-7.42 (m, 3H), 8.22 (d, 1H) .
Compound 2-11: 4.28 (s, 4H), 6.71 (dd, 1H), 7.00 (m, 1H), 7.15-7.45 (m, 15H), 8.60 (d, 1H).
　化合物2-15　：　1.96 (s, 3H), 3.18 (s, 3H), 6.84 (m, 1H), 7.06 (m, 1H), 7.30-7.40 (m, 2H), 7.49-7.52 (m, 2H), 7.64 (m, 1H), 8.77 (d, 1H, J = 2.7 Hz)
　化合物2-16　：　1.92 (s, 3H), 3.29 (s, 3H), 6.97 (m, 1H), 7.28-7.41 (m, 3H), 7.50-7.53 (m, 2H), 7.65 (m, 1H), 8.78 (d, 1H).
　化合物2-18　：　1.99 (s, 3H), 4.26 (d, 1H), 5.62 (d, 1H), 6.67 (m, 1H), 6.95-7.06 (m, 4H), 7.18-7.23 (m, 3H), 7.28-7.52 (m, 4H), 8.28 (d, 1H).
　化合物2-19　：　3.39 (s, 3H), 6.68 (m, 1H), 7.01 (m, 1H), 7.31-7.44 (m, 2H), 7.48-7.58 (m, 2H), 7.77 (m, 1H), 8.79 (d, 1H, J = 2.8 Hz)
　化合物2-21　：　3.47 (s, 3H), 6.70 (m, 1H), 7.01 (m, 1H), 7.30-7.43 (m, 2H), 7.49-7.58 (m, 2H), 7.83 (m, 1H), 8.86 (d, 1H, J = 2.4 Hz)
　化合物a1-81　：　1.35 (d, 6H), 3.77 (sep, 1H), 7.32 (m, 1H), 7.52 (m, 1H), 7.62-7.69 (m, 3H), 8.08 (m, 1H), 8.74 (s, 1H)
　化合物a1-87　：　0.91 (d, 6H), 2.19 (sep, 1H), 3.29 (d, 2H), 7.28 (dd, 1H), 7.54 (dd, 1H), 7.58-7.68 (m, 4H), 8.08 (dd, 1H), 8.75 (s, 1H)
　化合物a1-94　：　0.94 (d, 6H), 2.21 (sep, 1H), 3.29 (d, 2H), 7.28 (dd, 1H), 7.44 (m, 1H), 7.54 (dd, 1H), 7.61 (t, 1H), 7.67 (dd, 1H), 7.73 (dd, 1H), 8.75 (s, 1H)
　化合物b2-53　：　7.17 (s, 1H), 7.4-7.7 (m, 8H), 7.92 (d, 1H), 8.73 (d, 1H) Compound 2-15: 1.96 (s, 3H), 3.18 (s, 3H), 6.84 (m, 1H), 7.06 (m, 1H), 7.30-7.40 (m, 2H), 7.49-7.52 (m, 2H) , 7.64 (m, 1H), 8.77 (d, 1H, J = 2.7 Hz)
Compound 2-16: 1.92 (s, 3H), 3.29 (s, 3H), 6.97 (m, 1H), 7.28-7.41 (m, 3H), 7.50-7.53 (m, 2H), 7.65 (m, 1H) , 8.78 (d, 1H).
Compound 2-18: 1.99 (s, 3H), 4.26 (d, 1H), 5.62 (d, 1H), 6.67 (m, 1H), 6.95-7.06 (m, 4H), 7.18-7.23 (m, 3H) , 7.28-7.52 (m, 4H), 8.28 (d, 1H).
Compound 2-19: 3.39 (s, 3H), 6.68 (m, 1H), 7.01 (m, 1H), 7.31-7.44 (m, 2H), 7.48-7.58 (m, 2H), 7.77 (m, 1H) , 8.79 (d, 1H, J = 2.8 Hz)
Compound 2-21: 3.47 (s, 3H), 6.70 (m, 1H), 7.01 (m, 1H), 7.30-7.43 (m, 2H), 7.49-7.58 (m, 2H), 7.83 (m, 1H) , 8.86 (d, 1H, J = 2.4 Hz)
Compound a1-81: 1.35 (d, 6H), 3.77 (sep, 1H), 7.32 (m, 1H), 7.52 (m, 1H), 7.62-7.69 (m, 3H), 8.08 (m, 1H), 8.74 (s, 1H)
Compound a1-87: 0.91 (d, 6H), 2.19 (sep, 1H), 3.29 (d, 2H), 7.28 (dd, 1H), 7.54 (dd, 1H), 7.58-7.68 (m, 4H), 8.08 (dd, 1H), 8.75 (s, 1H)
Compound a1-94: 0.94 (d, 6H), 2.21 (sep, 1H), 3.29 (d, 2H), 7.28 (dd, 1H), 7.44 (m, 1H), 7.54 (dd, 1H), 7.61 (t , 1H), 7.67 (dd, 1H), 7.73 (dd, 1H), 8.75 (s, 1H)
Compound b2-53: 7.17 (s, 1H), 7.4-7.7 (m, 8H), 7.92 (d, 1H), 8.73 (d, 1H)
（製剤）
　次に、本発明に係る農園芸用殺菌剤の実施例を若干示すが、添加物および添加割合は、これら実施例に限定されるべきものではなく、広範囲に変化させることが可能である。また、製剤実施例中の部は重量部を示す。 (Formulation)
Next, some examples of the agricultural and horticultural fungicide according to the present invention are shown. However, the additive and the addition ratio are not limited to these examples, and can be changed in a wide range. Moreover, the part in a formulation Example shows a weight part.
製剤実施例１　　　　水和剤
　　本発明の含窒素ヘテロ環化合物　　　　　　　　　４０部
　　クレー　　　　　　　　　　　　　　　　　　　　４８部
　　ジオクチルスルホサクシネートナトリウム塩　　　　４部
　　リグニンスルホン酸ナトリウム塩　　　　　　　　　８部
　以上を均一に混合して微細に粉砕し、有効成分４０％の水和剤を得る。 Formulation Example 1 Wetting agent Nitrogen-containing heterocyclic compound of the present invention 40 parts Clay 48 parts Dioctyl sulfosuccinate sodium salt 4 parts Lignin sulfonic acid sodium salt 8 parts The above ingredients are uniformly mixed and finely pulverized, and the active ingredient 40 % Wettable powder is obtained.
製剤実施例２　　　　乳剤
　　本発明の含窒素ヘテロ環化合物　　　　　　　　　１０部
　　ソルベッソ２００　　　　　　　　　　　　　　　５３部
　　シクロヘキサノン　　　　　　　　　　　　　　　２６部
　　ドデシルベンゼンスルホン酸カルシウム塩　　　　　１部
　　ポリオキシエチレンアルキルアリルエーテル　　　１０部
　以上を混合溶解し、有効成分１０％の乳剤を得る。 Formulation Example 2 Emulsion Nitrogen-containing heterocyclic compound of the present invention 10 parts Solvesso 200 53 parts Cyclohexanone 26 parts Calcium dodecylbenzenesulfonate 1 part Polyoxyethylene alkylallyl ether 10 parts An emulsion containing 10% active ingredient by mixing and dissolving the above. Get.
製剤実施例３　　　　粉剤
　　本発明の含窒素ヘテロ環化合物　　　　　　　　　１０部
　　クレー　　　　　　　　　　　　　　　　　　　　９０部
　以上を均一に混合して微細に粉砕し、有効成分１０％の粉剤を得る。 Formulation Example 3 Dust The nitrogen-containing heterocyclic compound of the present invention 10 parts Clay 90 parts The above is uniformly mixed and finely pulverized to obtain a powder of 10% active ingredient.
製剤実施例４　　　　粒剤
　　本発明の含窒素ヘテロ環化合物　　　　　　　　　　５部
　　クレー　　　　　　　　　　　　　　　　　　　　７３部
　　ベントナイト　　　　　　　　　　　　　　　　　２０部
　　ジオクチルスルホサクシネートナトリウム塩　　　　１部
　　リン酸カリウム　　　　　　　　　　　　　　　　　１部
　以上をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥して有効成分５％の粒剤を得る。 Formulation Example 4 Granules Nitrogen-containing heterocyclic compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctyl sulfosuccinate sodium salt 1 part Potassium phosphate 1 part The above was pulverized and mixed well, and water was added and kneaded well. Thereafter, granulation and drying are performed to obtain a granule containing 5% of the active ingredient.
製剤実施例５　　　　懸濁剤
　　本発明の含窒素ヘテロ環化合物　　　　　　　　　１０部
　　ポリオキシエチレンアルキルアリルエーテル　　　　４部
　　ポリカルボン酸ナトリウム塩　　　　　　　　　　　２部
　　グリセリン　　　　　　　　　　　　　　　　　　１０部
　　キサンタンガム　　　　　　　　　　　　　　　０．２部
　　水　　　　　　　　　　　　　　　　　　　　７３．８部
　以上を混合し、粒度が３ミクロン以下になるまで湿式粉砕し、有効成分１０％の懸濁剤を得る。 Formulation Example 5 Suspending agent Nitrogen-containing heterocyclic compound of the present invention 10 parts Polyoxyethylene alkyl allyl ether 4 parts Polycarboxylic acid sodium salt 2 parts Glycerin 10 parts Xanthan gum 0.2 parts Water 73.8 parts Wet mill until the particle size is 3 microns or less to obtain a 10% active ingredient suspension.
製剤実施例６　　　　顆粒水和剤
　　本発明の含窒素ヘテロ環化合物　　　　　　　　　４０部
　　クレー　　　　　　　　　　　　　　　　　　　　３６部
　　塩化カリウム　　　　　　　　　　　　　　　　　１０部
　　アルキルベンゼンスルホン酸ナトリウム塩　　　　　１部
　　リグニンスルホン酸ナトリウム塩　　　　　　　　　８部
　　アルキルベンゼンスルホン酸ナトリウム塩のホルムアルデヒド縮合物
　　　　　　　　　　　　　　　　　　　　　　　　　　５部
　以上を均一に混合して微細に粉砕後、適量の水を加えてから練り込んで粘土状にする。粘土状物を造粒した後乾燥し、有効成分４０％の顆粒水和剤を得る。 Formulation Example 6 Granule wettable powder Nitrogen-containing heterocyclic compound of the present invention 40 parts Clay 36 parts Potassium chloride 10 parts Alkylbenzenesulfonic acid sodium salt 1 part Ligninsulfonic acid sodium salt 8 parts Formaldehyde condensate of alkylbenzenesulfonic acid sodium salt 5 parts After the above is uniformly mixed and finely pulverized, an appropriate amount of water is added and then kneaded to form a clay. The clay-like product is granulated and then dried to obtain a granule wettable powder containing 40% of the active ingredient.
（生物試験例１）リンゴ黒星病防除試験
　素焼きポットで栽培したリンゴ幼苗（品種「国光」、３～４葉期）に、製剤実施例２において得られた乳剤を有効成分１２５ｐｐｍの濃度に希釈して散布し、室温で自然乾燥した。その後、リンゴ黒星病菌（Venturia inaequalis）の分生胞子を接種し、明暗を１２時間毎に繰り返す２０℃、高湿度の室内に２週間保持した。葉上の病斑出現状態を無処理と比較調査し、防除効果を求めた。
　化合物番号1-2、1-5、1-8、1-10、1-11、1-12、1-13、1-14、1-15、1-16、1-17、1-18、1-19、1-20、1-21、1-22、1-23、1-24、1-25、1-26、1-27、1-28、1-29、1-30、1-32、1-33、1-34、1-35、1-36、1-37、1-39、1-41、1-60、1-61、1-89、1-90、1-91、2-1、2-2、2-3、2-6、2-7、2-8、2-9、2-10、2-11、2-13、2-15、2-16、2-18、2-19、2-20、および2-21の化合物についてリンゴ黒星病防除試験を行った結果、いずれの化合物も７５％以上の防除価を示した。
　化合物番号a1-1、a1-2、a1-3、a1-4、a1-5、a1-10、a1-11、a1-12、a1-13、a1-14、a1-15、a1-16、a1-18、a1-32、a1-62、a1-74、a1-75、a1-76、a1-77、a1-78、a1-79、a1-80、a1-81、a1-82、a1-83、a1-84、a1-85、a1-86、a1-87、a1-88、a1-89、a1-90、a1-91、a1-92、a1-93、a1-94、a1-95、b3-2、およびb4-2の化合物についてリンゴ黒星病防除試験を行った結果、いずれの化合物も７５％以上の防除価を示した。 (Biological test example 1) Apple black spot disease control test Apple seedlings (variety “Kokumitsu”, 3-4 leaf stage) cultivated in an unglazed pot were diluted with the emulsion obtained in Formulation Example 2 to a concentration of 125 ppm active ingredient. Sprayed and air dried at room temperature. Then, conidia of apple scab (Venturia inaequalis) were inoculated, and the light and darkness was repeated every 12 hours and kept in a room at 20 ° C. and high humidity for 2 weeks. The lesion appearance state on the leaf was compared with no treatment, and the control effect was obtained.
Compound Nos. 1-2, 1-5, 1-8, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1- 32, 1-33, 1-34, 1-35, 1-36, 1-37, 1-39, 1-41, 1-60, 1-61, 1-89, 1-90, 1-91, 2-1, 2-2, 2-3, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-13, 2-15, 2-16, 2- As a result of the apple scab control test for the compounds 18, 2-19, 2-20, and 2-21, all the compounds showed a control value of 75% or more.
Compound Nos. A1-1, a1-2, a1-3, a1-4, a1-5, a1-10, a1-11, a1-12, a1-13, a1-14, a1-15, a1-16, a1-18, a1-32, a1-62, a1-74, a1-75, a1-76, a1-77, a1-78, a1-79, a1-80, a1-81, a1-82, a1- 83, a1-84, a1-85, a1-86, a1-87, a1-88, a1-89, a1-90, a1-91, a1-92, a1-93, a1-94, a1-95, As a result of the apple scab control test for the compounds b3-2 and b4-2, all compounds showed a control value of 75% or more.
（生物試験例２）キュウリ灰色かび病防除試験
　素焼きポットで栽培したキュウリ幼苗（品種「相模半白」、子葉期）に、製剤実施例２において得られた乳剤を有効成分１００ｐｐｍの濃度に希釈して散布し、室温で自然乾燥した。その後、キュウリ灰色かび病菌（Botrytis cinerea）の分生胞子懸濁液を滴下接種し、２０℃、高湿度の暗室内に４日間保持した。葉上の病斑出現状態を無処理と比較調査し、防除効果を求めた。
　化合物番号1-3、1-8、1-9、1-10、1-12、1-14、1-15、1-16、1-17、1-18、1-19、1-20、1-21、1-22、1-23、1-24、1-25、1-26、1-27、1-28、1-29、1-30、1-31、1-32、1-33、1-34、1-35、1-41、1-60、1-61、1-62、1-63、1-64、1-65、1-66、1-67、1-68、1-69、1-70、1-71、1-72、1-89、1-90、1-91、2-2、2-3、2-6、2-8、2-9、2-16、2-18、2-19、および2-21の化合物についてキュウリ灰色かび病防除試験を行った結果、いずれの化合物も７５％以上の防除価を示した。
　化合物番号a1-2、a1-3、a1-4、a1-5、a1-6、a1-7、a1-10、a1-11、a1-12、a1-13、a1-14、a1-15、a1-16、a1-17、a1-18、a1-19、a1-20、a1-21、a1-32、a1-62、a1-74、a1-75、a1-76、a1-77、a1-78、a1-79、a1-80、a1-81、a1-82、a1-83、a1-84、a1-85、a1-86、a1-87、a1-88、a1-89、a1-90、a1-91、a1-92、a1-93、a1-94、a1-95、b3-2、b3-12、およびb4-2の化合物についてキュウリ灰色かび病防除試験を行った結果、いずれの化合物も７５％以上の防除価を示した。 (Biological Test Example 2) Cucumber Gray Mold Control Test A cucumber seedling (cultivar "Sagamihanjiro", cotyledon stage) cultivated in an unglazed pot was diluted with the emulsion obtained in Formulation Example 2 to a concentration of 100 ppm active ingredient. Sprayed and air dried at room temperature. Thereafter, a conidial spore suspension of Botrytis cinerea was inoculated dropwise and kept in a dark room at 20 ° C. and high humidity for 4 days. The lesion appearance state on the leaf was compared with no treatment, and the control effect was obtained.
Compound numbers 1-3, 1-8, 1-9, 1-10, 1-12, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1- 33, 1-34, 1-35, 1-41, 1-60, 1-61, 1-62, 1-63, 1-64, 1-65, 1-66, 1-67, 1-68, 1-69, 1-70, 1-71, 1-72, 1-89, 1-90, 1-91, 2-2, 2-3, 2-6, 2-8, 2-9, 2- As a result of the cucumber gray mold control test for the compounds 16, 2-18, 2-19, and 2-21, all compounds showed a control value of 75% or more.
Compound Nos. A1-2, a1-3, a1-4, a1-5, a1-6, a1-7, a1-10, a1-11, a1-12, a1-13, a1-14, a1-15, a1-16, a1-17, a1-18, a1-19, a1-20, a1-21, a1-32, a1-62, a1-74, a1-75, a1-76, a1-77, a1- 78, a1-79, a1-80, a1-81, a1-82, a1-83, a1-84, a1-85, a1-86, a1-87, a1-88, a1-89, a1-90, As a result of conducting a cucumber gray mold control test on the compounds a1-91, a1-92, a1-93, a1-94, a1-95, b3-2, b3-12, and b4-2, all the compounds were A control value of 75% or more was exhibited.
（生物試験例３）水稲いもち病水面施用試験（１４日後接種）
　市販培土を詰め湛水状態にしたポットで栽培したイネ幼苗（品種「コシヒカリ」、１葉期）に、製剤実施例２において得られた乳剤を有効成分４００ｐｐｍの濃度で水面への点滴処理した。点滴処理後１４日経過時にイネいもち病菌（Magnaporthe grisea）の分生胞子懸濁液を噴霧接種した。２５℃、高湿度の暗室内に２日間保持した。その後、１２時間毎に明暗を繰り返す２５℃の室内に８日間保持した。葉上の病斑出現状態を無処理苗と比較調査し、防除効果を求めた。
　化合物番号a1-4、a1-5、a1-10、a1-11、a1-12、およびa1-13の化合物について水稲いもち病水面施用試験を行った。その結果、いずれの化合物も６０％以上の防除価を示した。 (Biological test example 3) Paddy rice blast disease water surface application test (inoculated 14 days later)
Rice seedlings (cultivar “Koshihikari”, 1-leaf stage) cultivated in pots filled with commercial soil and submerged in water were instilled onto the water surface at a concentration of 400 ppm active ingredient in the emulsion of Formulation Example 2. After 14 days from the instillation, a conidial spore suspension of rice blast fungus (Magnaporthe grisea) was spray-inoculated. It was kept in a dark room at 25 ° C. and high humidity for 2 days. Then, it was kept for 8 days in a room at 25 ° C. where light and dark were repeated every 12 hours. The lesion appearance on the leaves was compared with the untreated seedlings to determine the control effect.
A paddy rice blast disease water surface application test was conducted on the compounds of compound numbers a1-4, a1-5, a1-10, a1-11, a1-12, and a1-13. As a result, all the compounds showed a control value of 60% or more.
（生物試験例４）水稲いもち病水面施用試験（２日後接種）
　市販培土を詰め湛水状態にしたポットでイネ幼苗を栽培したイネ幼苗（品種「コシヒカリ」、1葉期）に、製剤実施例２において得られた乳剤を有効成分４００ｐｐｍの濃度で水面へ点滴処理した。点滴処理後２日経過時にイネいもち病菌（Magnaporthe grisea）の分生胞子懸濁液を噴霧接種した。２５℃、高湿度の暗室内に２日間保持した。その後、１２時間毎に明暗を繰り返す２５℃の室内に８日間保持した。葉上の病斑出現状態を無処理と比較調査し、防除効果を求めた。
６０％以上の防除価を示した化合物番号：　a1-88、a1-91 (Biological test example 4) Paddy rice blast disease water surface application test (inoculated 2 days later)
Rice seedlings (variety “Koshihikari”, 1-leaf stage) cultivated in a pot filled with commercial soil and submerged in water are instilled onto the water surface at a concentration of 400 ppm active ingredient in the formulation example 2 did. Two days after the drip treatment, a conidial spore suspension of rice blast fungus (Magnaporthe grisea) was spray-inoculated. It was kept in a dark room at 25 ° C. and high humidity for 2 days. Then, it was kept for 8 days in a room at 25 ° C. where light and dark were repeated every 12 hours. The lesion appearance state on the leaf was compared with no treatment, and the control effect was obtained.
Compound numbers showing control values of 60% or more: a1-88, a1-91
（生物試験例５）キュウリつる割病種子処理試験
　キュウリつる割病菌（Ｆｕｓａｒｉｕｍ　ｏｘｙｓｐｏｒｕｍ）によって汚染されたキュウリ種子（品種「相模半白」）に対して本発明化合物の乳剤を有効成分１g/kg種子となるように種子処理した。これらの種子を播種し、３週間後に発病程度を無処理と比較調査し、防除効果を求めた。
７５％以上の防除価を示した化合物番号：a1-88、a1-91、a1-93 (Biological Test Example 5) Cucumber vine split seed treatment test The cucumber seeds contaminated by cucumber vine split fungus (Fusarium oxysporum) (variety “Sagamihanjiro”) were treated with an emulsion of the compound of the present invention at 1 g / kg seed. The seeds were treated so that These seeds were sown, and after 3 weeks, the disease severity was compared with no treatment to determine the control effect.
Compound numbers showing control values of 75% or more: a1-88, a1-91, a1-93
　効果が確実で安全に使用できる農園芸用殺菌剤、および農園芸用殺菌剤の有効成分として有用な含窒素ヘテロ環化合物またはその塩を提供することができる。 It is possible to provide an agricultural and horticultural fungicide that has a certain effect and can be used safely, and a nitrogen-containing heterocyclic compound or a salt thereof useful as an active ingredient of the agricultural and horticultural fungicide.

Claims (7)

  1. 　式（I）で表される含窒素ヘテロ環化合物またはその塩。
    Figure JPOXMLDOC01-appb-C000001
     〔式（I）中、Ｒは、ＯＲ1で表される基、ＮＲ1Ｒ2で表される基、ＳＲ1で表される基、Ｓ（＝Ｏ）Ｒ3で表される基、ＳＯ2Ｒ3で表される基、Ｓ(＝Ｏ)(＝ＮＲ4)Ｒ5で表される基、Ｎ＝Ｓ(＝Ｏ)Ｒ4Ｒ5で表される基、またはニトロ基を示す。
    　Ｒ1は、水素原子、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、置換基を有するスルホニル基、または無置換の若しくは置換基を有するアミノ基を示す。
    　Ｒ2は、水素原子、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、置換基を有するスルホニル基、無置換の若しくは置換基を有する水酸基、または無置換の若しくは置換基を有するアミノ基を示す。
    　Ｒ3は、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有するメルカプト基、無置換の若しくは置換基を有する水酸基、または無置換の若しくは置換基を有するアミノ基を示す。
    　Ｒ4およびＲ5は、それぞれ独立に、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、または無置換の若しくは置換基を有するヘテロ環基を示す。
    　ＮＲ1Ｒ2で表される基において、Ｒ1とＲ2とが一緒になって、無置換の若しくは置換基を有する３～８員環、＝ＣＲaＲb、または＝Ｎ－Ｒcを形成してもよい。
    　ＲaおよびＲbは、それぞれ独立に、水素原子、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、置換基を有するスルホニル基、無置換の若しくは置換基を有するメルカプト基、無置換の若しくは置換基を有する水酸基、または無置換の若しくは置換基を有するアミノ基を示す。
    　Ｒcは、無置換の若しくは置換基を有する水酸基、または無置換の若しくは置換基を有するＣ１～８アルキル基を示す。
    　Ｎ＝Ｓ(＝Ｏ)Ｒ4Ｒ5で表される基において、Ｒ4とＲ5とが一緒になって、無置換の若しくは置換基を有する５～８員環を形成してもよい。
    　Ｘ1は、それぞれ独立に、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有する（１－イミノ）Ｃ１～８アルキル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、無置換の若しくは置換基を有する水酸基、無置換の若しくは置換基を有するアミノ基、無置換の若しくは置換基を有するメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、またはニトロ基を示す。
    　ｍは、Ｘ1の個数を示し且つ０～５のいずれかの整数である。
    　Ｂは、炭素原子または窒素原子を示す。
    　Ｄは、無置換の若しくはＸ1で置換された５～７員炭化水素環、または無置換の若しくはＸ1で置換された５～７員ヘテロ環を示す。
    　Ｘ2は、それぞれ独立に、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有する（１－イミノ）Ｃ１～８アルキル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、無置換の若しくは置換基を有する水酸基、無置換の若しくは置換基を有するアミノ基、無置換の若しくは置換基を有するメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、またはニトロ基を示す。
    　ｎは、Ｘ2の個数を示し且つ０～３のいずれかの整数である。
    　Ｘ2のいずれかひとつと、Ｒとが一緒になって、無置換の若しくは置換基を有する５～８員環を形成してもよい。
    　Ｅは、無置換の若しくはＸ２で置換された５～７員炭化水素環、または無置換の若しくはＸ２で置換された５～７員ヘテロ環を示す。
    　Ｘは、酸素原子、窒素原子、またはＣ１～８アルキル基で置換された窒素原子を示す。〕     A nitrogen-containing heterocyclic compound represented by the formula (I) or a salt thereof.
    Figure JPOXMLDOC01-appb-C000001
     [In the formula (I), R represents a group represented by OR 1 , a group represented by NR 1 R 2 , a group represented by SR 1 , a group represented by S (═O) R 3 , SO 2 represents a group represented by R 3 , a group represented by S (═O) (═NR 4 ) R 5 , a group represented by N═S (═O) R 4 R 5 , or a nitro group.
    R 1 is a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, A substituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted group; An unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted carboxyl group, an unsubstituted or substituted carbamoyl group, a substituted sulfonyl group, or An amino group having a substituent or a substituent is shown.
    R 2 represents a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, A substituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted group; Having a heterocyclic group, an unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted carboxyl group, an unsubstituted or substituted carbamoyl group, a substituted sulfonyl group, unsubstituted Or a hydroxyl group having a substituent, or an amino group having no substituent or a substituent.
    R 3 is an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, unsubstituted or A substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted heterocycle A group, an unsubstituted or substituted mercapto group, an unsubstituted or substituted hydroxyl group, or an unsubstituted or substituted amino group.
    R 4 and R 5 are each independently an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 An alkynyl group, an unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, or unsubstituted Or a heterocyclic group having a substituent.
    In the group represented by NR 1 R 2 , R 1 and R 2 are taken together to form an unsubstituted or substituted 3- to 8-membered ring, ═CR a R b , or ═N—R c . It may be formed.
    R a and R b each independently have a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted group A C2-8 alkynyl group, an unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted or substituted C6-10 aryl group, Unsubstituted or substituted heterocyclic group, unsubstituted or substituted C1-8 acyl group, unsubstituted or substituted carboxyl group, unsubstituted or substituted carbamoyl group, substituted group A sulfonyl group having, an unsubstituted or substituted mercapto group, an unsubstituted or substituted hydroxyl group, or unsubstituted Or an amino group having a substituent.
    R c represents an unsubstituted or substituted hydroxyl group, or an unsubstituted or substituted C1-8 alkyl group.
    In the group represented by N═S (═O) R 4 R 5 , R 4 and R 5 may be combined to form an unsubstituted or substituted 5- to 8-membered ring.
    X 1 is each independently an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, Unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C4-8 cycloalkenyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted An unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted (1-imino) C1-8 alkyl group, an unsubstituted or substituted carboxyl group, Unsubstituted or substituted carbamoyl group, unsubstituted or substituted hydroxyl group, unsubstituted or substituted amino group Mercapto group with an unsubstituted or substituted group, a sulfonyl group having a substituent, a halogeno group, a cyano group or a nitro group.
    m represents the number of X 1 and is an integer from 0 to 5.
    B represents a carbon atom or a nitrogen atom.
    D represents a 5- to 7-membered heterocycle substituted with been 5-7 membered hydrocarbon ring or an unsubstituted or X 1, substituted by unsubstituted or X 1.
    X 2 each independently represents an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, Unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C4-8 cycloalkenyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted An unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted (1-imino) C1-8 alkyl group, an unsubstituted or substituted carboxyl group, Unsubstituted or substituted carbamoyl group, unsubstituted or substituted hydroxyl group, unsubstituted or substituted amino group Mercapto group with an unsubstituted or substituted group, a sulfonyl group having a substituent, a halogeno group, a cyano group or a nitro group.
    n represents the number of X 2 and is an integer from 0 to 3.
    Any one of X 2 and R may be combined with each other to form an unsubstituted or substituted 5- to 8-membered ring.
    E shows unsubstituted or 5- to 7-membered hydrocarbon ring substituted with X 2, or unsubstituted or a 5-7 membered heterocyclic ring substituted with X 2.
    X represents an oxygen atom, a nitrogen atom, or a nitrogen atom substituted with a C1-8 alkyl group. ]
  2. 　請求項１に記載された式(I)が、式（II）で表されることを特徴とする含窒素ヘテロ環化合物またはその塩。
    Figure JPOXMLDOC01-appb-C000002
     （式（II）中、Ｒ、Ｘ1、ｍ、Ｘ2、ｎ、Ｄ、Ｂ、およびＸは、請求項１に記載の式（I）中のそれぞれと同じ意味を示す。
    　Ａ１、Ａ２、Ａ３、およびＡ４は、それぞれ独立して、炭素原子または窒素原子を示す。）     A nitrogen-containing heterocyclic compound or a salt thereof, wherein the formula (I) according to claim 1 is represented by the formula (II).
    Figure JPOXMLDOC01-appb-C000002
     (In the formula (II), R, X 1 , m, X 2 , n, D, B, and X have the same meaning as in the formula (I) according to claim 1.
    A 1 , A 2 , A 3 , and A 4 each independently represent a carbon atom or a nitrogen atom. )
  3. 　請求項２に記載された式(II)が、式（III）で表されることを特徴とする含窒素ヘテロ環化合物またはその塩。
    Figure JPOXMLDOC01-appb-C000003
     （式（III）中、Ｒ、Ｘ1、ｍ、Ｘ2、ｎ、Ａ１、Ａ２、Ａ３、Ａ４、Ｂ、およびＸは、請求項２に記載の式（II）中のそれぞれと同じ意味を示す。）     A nitrogen-containing heterocyclic compound or a salt thereof, wherein the formula (II) according to claim 2 is represented by the formula (III).
    Figure JPOXMLDOC01-appb-C000003
     (In the formula (III), R, X 1 , m, X 2 , n, A 1 , A 2 , A 3 , A 4 , B, and X are each in the formula (II) according to claim 2. Indicates the same meaning.)
  4. 　請求項１に記載された式(I)が、式（IV）で表されることを特徴とする含窒素ヘテロ環化合物またはその塩。
    Figure JPOXMLDOC01-appb-C000004
     （式（IV）中、Ｒ、Ｘ1、ｍ、Ｘ2、ｎ、Ｂ、およびＸは、請求項１に記載の式（I）中のそれぞれと同じ意味を示す。）     A nitrogen-containing heterocyclic compound or a salt thereof, wherein the formula (I) according to claim 1 is represented by the formula (IV).
    Figure JPOXMLDOC01-appb-C000004
     (In the formula (IV), R, X 1 , m, X 2 , n, B, and X have the same meanings as in the formula (I) according to claim 1.)
  5. 　請求項１に記載された式(I)が、式（V）で表されることを特徴とする含窒素ヘテロ環化合物またはその塩。
    Figure JPOXMLDOC01-appb-C000005
     （式（V）中、Ｒ、Ｘ1、ｍ、Ｘ2、ｎ、Ｄ、Ｂ、およびＸは、請求項１に記載の式（I）中のそれぞれと同じ意味を示す。
    　Ａ５、Ａ６、およびＡ７は、それぞれ独立して、炭素原子、窒素原子、酸素原子、または硫黄原子を示す。ただし、酸素原子同士、硫黄原子同士、酸素原子と硫黄原子の組合わせが隣接することはない。）     A nitrogen-containing heterocyclic compound or a salt thereof, wherein the formula (I) according to claim 1 is represented by the formula (V).
    Figure JPOXMLDOC01-appb-C000005
     (In the formula (V), R, X 1 , m, X 2 , n, D, B, and X have the same meaning as in the formula (I) according to claim 1.
    A 5 , A 6 , and A 7 each independently represent a carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom. However, oxygen atoms, sulfur atoms, or a combination of oxygen atoms and sulfur atoms are not adjacent to each other. )
  6. 　請求項５に記載された式(V)が、式（VI）で表されることを特徴とする含窒素ヘテロ環化合物またはその塩。
    Figure JPOXMLDOC01-appb-C000006
     （式（VI）中、Ｒ、Ｘ1、ｍ、Ｘ2、ｎ、Ａ５、Ａ６、Ａ７、Ｂ、およびＸは、請求項５に記載の式（V）中のそれぞれと同じ意味を示す。）     A nitrogen-containing heterocyclic compound or a salt thereof, wherein the formula (V) according to claim 5 is represented by the formula (VI).
    Figure JPOXMLDOC01-appb-C000006
     (In the formula (VI), R, X 1 , m, X 2 , n, A 5 , A 6 , A 7 , B, and X have the same meaning as in the formula (V) according to claim 5. Is shown.)
  7. 　請求項１～６のいずれか１項に記載の含窒素ヘテロ環化合物またはその塩から選ばれる少なくとも１種を有効成分として含有する農園芸用殺菌剤。 An agricultural and horticultural fungicide containing, as an active ingredient, at least one selected from the nitrogen-containing heterocyclic compound or a salt thereof according to any one of claims 1 to 6.
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