WO2013002205A1 - Composé hétérocyclique contenant un azote et bactéricide à visée agricole ou horticole - Google Patents

Composé hétérocyclique contenant un azote et bactéricide à visée agricole ou horticole Download PDF

Info

Publication number
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
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
unsubstituted
formula
represented
Prior art date
Application number
PCT/JP2012/066240
Other languages
English (en)
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
Original Assignee
日本曹達株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 日本曹達株式会社 filed Critical 日本曹達株式会社
Priority to JP2013522864A priority Critical patent/JP5753583B2/ja
Publication of WO2013002205A1 publication Critical patent/WO2013002205A1/fr

Links

Classifications

    • 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.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Cette invention concerne un composé hétérocyclique contenant un azote représenté par la formule (I) ou un sel de celui-ci ; et un bactéricide à visée agricole ou horticole, qui contient, à titre de principe actif, au moins une substance qui est choisie parmi les composés hétérocycliques contenant un azote représentés par la formule (I) ou leurs sels.
PCT/JP2012/066240 2011-06-28 2012-06-26 Composé hétérocyclique contenant un azote et bactéricide à visée agricole ou horticole WO2013002205A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2013522864A JP5753583B2 (ja) 2011-06-28 2012-06-26 含窒素ヘテロ環化合物および農園芸用殺菌剤

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2011-143479 2011-06-28
JP2011143479 2011-06-28
JP2012006279 2012-01-16
JP2012-006279 2012-01-16

Publications (1)

Publication Number Publication Date
WO2013002205A1 true WO2013002205A1 (fr) 2013-01-03

Family

ID=47424097

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2012/066240 WO2013002205A1 (fr) 2011-06-28 2012-06-26 Composé hétérocyclique contenant un azote et bactéricide à visée agricole ou horticole

Country Status (4)

Country Link
JP (1) JP5753583B2 (fr)
AR (1) AR086744A1 (fr)
TW (1) TW201304681A (fr)
WO (1) WO2013002205A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017072283A1 (fr) 2015-10-29 2017-05-04 Bayer Cropscience Aktiengesellschaft Hétérocycles silylphénoxy trisubstitués et analogues
WO2018197692A1 (fr) * 2017-04-27 2018-11-01 Bayer Aktiengesellschaft Hétéroarylphénylaminoquinoléines et analogues
WO2018202712A1 (fr) 2017-05-03 2018-11-08 Bayer Aktiengesellschaft Silylméthylphénoxyquinoléines trisubstitués et analogues
WO2018202706A1 (fr) 2017-05-03 2018-11-08 Bayer Aktiengesellschaft Silylhétéroaryloxyquinoléines trisubstituées et analogues
WO2019122319A1 (fr) 2017-12-21 2019-06-27 Bayer Aktiengesellschaft Silylméthylhétéroaryloxyquinoléines trisubstitués et analogues
WO2021209490A1 (fr) 2020-04-16 2021-10-21 Bayer Aktiengesellschaft Cyclaminephénylaminoquinoléines utiles en tant que fongicides

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3666814A (en) * 1970-03-03 1972-05-30 Delta W Gier Chloronitrophenyl ethers as herbicides
JPS6212759A (ja) * 1985-06-20 1987-01-21 イ−・アイ・デユポン・デ・ニモアス・アンド・カンパニ− 除草性アリ−ルオキシベンゼン酢酸誘導体
WO1988004294A2 (fr) * 1986-12-05 1988-06-16 E.I. Du Pont De Nemours And Company Derives de l'acide aryloxybenzene acetique a proprietes herbicides
WO1998023155A1 (fr) * 1996-11-26 1998-06-04 E.I. Du Pont De Nemours And Company Amides cycliques arthropodicides et fongicides
JP2002536446A (ja) * 1999-02-09 2002-10-29 ３−ディメンショナル ファーマシューティカルズ， インコーポレイテッド プロテアーゼ阻害剤としての、ヘテロアリールアミジン類、メチルアミジン類およびグアニジン類

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6097964A (ja) * 1983-11-02 1985-05-31 Nissan Chem Ind Ltd Ν−キノキザリルアニリン系化合物，その製造法および農園芸用殺菌，殺虫，殺ダニ剤
MX9710259A (es) * 1995-06-20 1998-03-29 Du Pont Amidas ciclicas fungicidas y artropodicidas.
DE10013318A1 (de) * 2000-03-17 2001-09-20 Merck Patent Gmbh Formulierung enthaltend Chinoxalinderivate
US7470712B2 (en) * 2004-01-21 2008-12-30 Bristol-Myers Squibb Company Amino-benzazoles as P2Y1 receptor inhibitors
ES2601178T3 (es) * 2005-09-01 2017-02-14 F. Hoffmann-La Roche Ag Diaminopirimidinas como moduladores de P2X3 y P3X2/3
GB0707704D0 (en) * 2007-04-20 2007-05-30 Glaxo Group Ltd Compounds
EP1990342A1 (fr) * 2007-05-10 2008-11-12 AEterna Zentaris GmbH Dérivés de pyridopyrazine, processus de fabrication et utilisations correspondantes
WO2009017838A2 (fr) * 2007-08-01 2009-02-05 Exelixis, Inc. Combinaisons d'inhibiteurs jak-2 et d'autres agents

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3666814A (en) * 1970-03-03 1972-05-30 Delta W Gier Chloronitrophenyl ethers as herbicides
JPS6212759A (ja) * 1985-06-20 1987-01-21 イ−・アイ・デユポン・デ・ニモアス・アンド・カンパニ− 除草性アリ−ルオキシベンゼン酢酸誘導体
WO1988004294A2 (fr) * 1986-12-05 1988-06-16 E.I. Du Pont De Nemours And Company Derives de l'acide aryloxybenzene acetique a proprietes herbicides
WO1998023155A1 (fr) * 1996-11-26 1998-06-04 E.I. Du Pont De Nemours And Company Amides cycliques arthropodicides et fongicides
JP2002536446A (ja) * 1999-02-09 2002-10-29 ３−ディメンショナル ファーマシューティカルズ， インコーポレイテッド プロテアーゼ阻害剤としての、ヘテロアリールアミジン類、メチルアミジン類およびグアニジン類

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017072283A1 (fr) 2015-10-29 2017-05-04 Bayer Cropscience Aktiengesellschaft Hétérocycles silylphénoxy trisubstitués et analogues
US11457629B2 (en) 2017-04-27 2022-10-04 Bayer Aktiengesellschaft Heteroarylphenylaminoquinolines and analogues
CN110603253A (zh) * 2017-04-27 2019-12-20 拜耳公司 杂芳基苯基氨基喹啉及类似物
KR20190141734A (ko) * 2017-04-27 2019-12-24 바이엘 악티엔게젤샤프트 헤테로아릴페닐아미노퀴놀린 및 유사체
JP2020517685A (ja) * 2017-04-27 2020-06-18 バイエル・アクチエンゲゼルシヤフト ヘテロアリールフェニルアミノキノリン類及び類似体
WO2018197692A1 (fr) * 2017-04-27 2018-11-01 Bayer Aktiengesellschaft Hétéroarylphénylaminoquinoléines et analogues
JP7157077B2 (ja) 2017-04-27 2022-10-19 バイエル・アクチエンゲゼルシヤフト ヘテロアリールフェニルアミノキノリン類及び類似体
CN110603253B (zh) * 2017-04-27 2023-01-20 拜耳公司 杂芳基苯基氨基喹啉及类似物
KR102554993B1 (ko) 2017-04-27 2023-07-12 바이엘 악티엔게젤샤프트 헤테로아릴페닐아미노퀴놀린 및 유사체
WO2018202712A1 (fr) 2017-05-03 2018-11-08 Bayer Aktiengesellschaft Silylméthylphénoxyquinoléines trisubstitués et analogues
WO2018202706A1 (fr) 2017-05-03 2018-11-08 Bayer Aktiengesellschaft Silylhétéroaryloxyquinoléines trisubstituées et analogues
WO2019122319A1 (fr) 2017-12-21 2019-06-27 Bayer Aktiengesellschaft Silylméthylhétéroaryloxyquinoléines trisubstitués et analogues
WO2021209490A1 (fr) 2020-04-16 2021-10-21 Bayer Aktiengesellschaft Cyclaminephénylaminoquinoléines utiles en tant que fongicides

Also Published As

Publication number Publication date
JPWO2013002205A1 (ja) 2015-02-23
JP5753583B2 (ja) 2015-07-22
TW201304681A (zh) 2013-02-01
AR086744A1 (es) 2014-01-22

Similar Documents

Publication Publication Date Title
JP5483485B2 (ja) 含窒素ヘテロ環化合物ならびに農園芸用殺菌剤
JP5775574B2 (ja) 含窒素ヘテロ環化合物および農園芸用殺菌剤
JP5729889B2 (ja) 含窒素ヘテロ環化合物および農園芸用殺菌剤
JP5442021B2 (ja) 含窒素ヘテロ環化合物およびその塩ならびに農園芸用殺菌剤
JP5281647B2 (ja) 含窒素ヘテロ環化合物およびその塩並びに農園芸用殺菌剤
JP5753583B2 (ja) 含窒素ヘテロ環化合物および農園芸用殺菌剤
WO2010137302A1 (fr) Dérivés hétéroaryles contenant de l'azote et fongicides pour utilisation agricole et horticole
JP6277501B2 (ja) ピリジン化合物および農園芸用殺菌剤
JP2014221747A (ja) 含窒素ヘテロ環化合物および農園芸用殺菌剤
WO2015060378A1 (fr) Dérivé d'aminopyridine et fongicide agricole et horticole
WO2012165305A1 (fr) Composé bipyridine et bactéricide
JP2014125441A (ja) 含窒素ヘテロ環化合物および農園芸用殺菌剤
JP2011162472A (ja) 含窒素ヘテロ環化合物またはその塩、ならびに農園芸用殺菌剤

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 12804741

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2013522864

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 12804741

Country of ref document: EP

Kind code of ref document: A1