WO2004039783A1 - Compose a base de quinoline-3-carboxamide - Google Patents

Compose a base de quinoline-3-carboxamide Download PDF

Info

Publication number
WO2004039783A1
WO2004039783A1 PCT/JP2003/013417 JP0313417W WO2004039783A1 WO 2004039783 A1 WO2004039783 A1 WO 2004039783A1 JP 0313417 W JP0313417 W JP 0313417W WO 2004039783 A1 WO2004039783 A1 WO 2004039783A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
compound
substituted
quinoline
different
Prior art date
Application number
PCT/JP2003/013417
Other languages
English (en)
Japanese (ja)
Inventor
Hiroyuki Ito
Takeshi Takada
Harukazu Tanaka
Yasushi Tamagawa
Original Assignee
Sankyo Agro Company, Limited
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 Sankyo Agro Company, Limited filed Critical Sankyo Agro Company, Limited
Priority to JP2004548028A priority Critical patent/JP4511362B2/ja
Priority to AU2003273064A priority patent/AU2003273064A1/en
Publication of WO2004039783A1 publication Critical patent/WO2004039783A1/fr

Links

Classifications

    • 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
    • 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3

Definitions

  • the present invention relates to a quinoline-13-carboxamide compound or a salt thereof, and a pesticide containing the same as an active ingredient.
  • WO 0/0733283 includes N-cycloalkylquinolinecarboxamide as a therapeutic agent for diseases of the central nervous system.
  • N-cycloalkyl-1-oxoquinoline-3-carboxamide is described as a ligand of the GABA receptor, and cycloalkylamine having a substituent at the 1-position and 3-cycloalkylamine are described.
  • the compound to which quinoline carboxylic acid is bound is not described, and there is no description about an agricultural and horticultural fungicide.
  • a quinoline 13-carboxamide compound can be used as an agricultural and horticultural fungicide.
  • the present inventors have conducted intensive studies on quinoline-13-carboxamide compounds, and as a result, have found that quinoline-3 in which cycloalkylamine or cycloalkulamine having a substituent at the 1-position is bonded to 3-quinolinecarboxylic acid.
  • Carboxamide compound or quinoline 3-Carbothioamide compound has excellent bactericidal activity against various plant diseases and is useful as an active ingredient of pesticides.
  • plant mold diseases agricultural and horticultural crops
  • the present invention has been found to be able to control rice blast (Pyricularia oryzae), which often causes severe damage to rice, and gray mold (Botrytis cinerea) of tomatoes, cucumber, and kidney beans at low doses. completed. Disclosure of the invention
  • the present invention has the general formula
  • A is the same or different and may be substituted with 1 to 4 ano'alkyl groups.
  • R is a C i-C 6 alkyl group which may be substituted with the same or different 1 to 3 substituents selected from the group consisting of a halogen atom, a Ci Ce alkoxy group and a phenoxy group,
  • Halogen atom C 1 -C 6 Anorekokishi group, phenylene Honoré groups and identical or different ivy 1-3 amino substituted with a substituent which may C 2 to -C 6 alkenyl group selected from the group consisting of phenoxy group,
  • Halogen atom C 1 -C 6 alkoxy group and the same or different ivy .1 ⁇ 3 substituents ⁇ and which may be C 2 to C 6 alkynyl group with a group selected the group or al consisting of phenoxy group,
  • Ci Ce alkyl group which may be substituted by 1 to 3 identical or different halogen atoms, ⁇ , to 6 alkoxy group, 1 to 2 identical or different 1 to 2 alkyl groups
  • An aralkyl group which may be substituted with the same or different 1 to 6 substituent (s) selected from the group consisting of a diamino group, a nitro group, a cyano group, a hydroxyl group, a mercapto group and a Ci Ce alkylthio group, or
  • X represents an oxygen atom or a sulfur atom
  • Y is a halogen atom, substituted by 1 to 3 identical or different halogen atoms Alkyl group, C Cs alkoxy group which may be substituted with 1 to 3 identical or different halogen atoms, phenyl group, phenoxy group, -acyloxy group, 1 to 2 identical or different C 1 It represents substituted by -C 6 alkyl group Yoi Amino group, a nitro group, a hydroxyl group, a substituent selected from the group consisting of mercapto Moto ⁇ Pi C 1 -C 6 alkylthio group,
  • n an integer of 0 to 5
  • Cycloalkyl group is, for example, a monocyclic or bicyclic cycloalkyl having 3 to 10 carbon atoms such as a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a norbornyl group.
  • An alkyl group preferably a cyclopentyl group, a cyclohexyl group or a cycloheptyl group, and more preferably a cyclohexyl group.
  • Cycloalkyl group is the aforementioned rCsCt.
  • cycloalkyl group for example, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2,2-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group
  • cycloalkyl group substituted by 1 to 4 identical or different C 1 to C 6 alkyl groups such as a mouth hexyl group, preferably a methyl group.
  • the “optionally substituted ⁇ 3- to cycloalkyl group” represented by A is preferably a cyclopentyl group, a cyclohexynole group or a cycloheptyl group, more preferably a cyclohexyl group .
  • the “ ⁇ to cycloalkenyl group” is, for example, a monocyclic or bicyclic cycloalkenyl group having 3 to 10 carbon atoms, such as a cyclopentenyl group, a cyclohexenyl group, and the like.
  • a cyclohexenyl group is, for example, a monocyclic or bicyclic cycloalkenyl group having 3 to 10 carbon atoms, such as a cyclopentenyl group, a cyclohexenyl group, and the like.
  • a cyclohexenyl group is, for example, a monocyclic or bicyclic cycloalkenyl group having 3 to 10 carbon atoms, such as a cyclopentenyl group, a cyclohexenyl group, and the like.
  • "to 0 6 alkyl group” for example, a methyl group, Echiru group, a propyl group, an isopropyl group, a butyl group, Isopuchiru group, s- butyl, t-loop Chinore group, pentyl group, isopentyl group, 2-methylbutyl, neopentyl, 1-ethylpropyl, hexyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 3,3-dimethylbutyl, 2 1 carbon atoms such as 1,2-dimethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, and 2-ethylbutyl
  • the “C 2 -C 6 alkyl group” may be linear or branched, and may contain an arbitrary number of double bonds.
  • vinyl group propane-1-yl group, aryl group, isopropyl group, butadiene
  • the “C 2 -C 6 alkynyl group” may be linear or branched, and may contain an arbitrary number of triple bonds.
  • Examples thereof include a 1-yl group and the like.
  • the "Ararukiru group", wherein the one or more radicals substituted hydrogen atom is "Ariru group” of the " ⁇ ⁇ 6 alkyl group” is fist down.
  • examples of the “heteroarylalkyl group” include groups in which one or more hydrogen atoms of the aforementioned rCiCealkyl group have been substituted with a “heteroaryl group”.
  • the heteroaryl group constituting the heteroarylalkyl group may be either monocyclic or polycyclic, and includes a heteroaryl group containing one or more heterocyclic atoms having the same or different ring structures. Can be used.
  • the type of the hetero atom is not particularly limited, and examples thereof include a nitrogen atom, an oxygen atom, and a sulfur atom.
  • Examples of the monocyclic heteroaryl group constituting the heteroarylalkyl group include a furyl group, a chel group, a pyrrolyl group, an oxazolyl group, an isooxazolyl group, a dihydroisooxazolyl group, a thiazolyl group, and an isothiyl group.
  • Examples thereof include a 5- to 7-membered monocyclic heteroaryl group such as an azolyl group, an imidazolyl group, a bilazolyl group, an oxaziazolyl group, a thiaziazolyl group, a triazolyl group, a tetrazolyl group, a pyridyl group, an azepyr group, and an oxazepinyl group.
  • a 5- to 7-membered monocyclic heteroaryl group such as an azolyl group, an imidazolyl group, a bilazolyl group, an oxaziazolyl group, a thiaziazolyl group, a triazolyl group, a tetrazolyl group, a pyridyl group, an azepyr group, and an oxazepinyl group.
  • Examples of the polycyclic heteroaryl group constituting the heteroarylalkyl group include a benzofural group, an isobenzofurel group, a benzophenyl group, an indolyl group, an isoindolyl group, an indazolyl group, a benzoxazolyl group, and a benzoisozo.
  • Xazolyl group benzothiazolyl group, benzoisothiazolyl group, benzoxodiazolyl group, benzothiadiazolyl group, benzotriazolyl group, quinolyl group, isoquinolyl group, cinnolinyl group, quinazolinyl group, quinoxalinyl group, Phthalazul group, naphthyridinyl group, purinyl group, pteridinyl group, carpazolyl group, carbolinyl group, acridinyl group, 2-atarizyl, 3-ataridiel, 4-ataridinyl, 9-acrylidinyl, phenoxazinyl group, phenothiazil group , Huenajour And an 8- to 14-membered polycyclic heteroaryl group such as a group.
  • the “rCiCe alkoxy group” is, for example, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, an s-butoxy group, a t-butoxy group, a pentyloxy group , Isopentyloxy, 2-methylbutoxy, neopentyloxy, 1-ethylpropoxy, hexoxy, (4-methylpentyl) oxy, (3-methylpentyl) oxy, ( 2-methylpentyl) oxy group, (1-methylpentyl) oxy group, 3,3-dimethylbutoxy group, 2,2-dimethylbutoxy group, 1,1-dimethylbutoxy group, 1,2-dimethylbutoxy group, 1,3 — A straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms such as dimethylbutoxy, 2,3-dimethylbutoxy and 2-ethyl
  • the “-?? siloxy group” includes, for example, a formyloxy group, a carbonyloxy group (C 2 -C 7 alkyl carbonyloxy group) to which the above “ ⁇ alkyl group” is bonded, and a “C 2 -C S ” Carbonyl group attached to an alkenyl group A xy group (C 3 -C 7 alkenylcarbonyloxy group) or a carboxy group (C 2 -C 7 alkoxycarbonyloxy group) to which the above-mentioned rC i Ce alkoxy group is bonded.
  • a straight-chain or branched alkylcarbonyloxy group having 2 to 5 carbon atoms (C 2 -C 5 alkylcarbonyloxy group), a straight-chain or branched alkoxycarbonyloxy group having 2 to 5 carbon atoms ( (C 2 -C 5 alkoxycarberoxy group), and more preferably an acetooxy group or a methoxycarbonyloxy group.
  • the “halogen atom” is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a fluorine atom, a chlorine atom or a bromine atom, and more preferably a fluorine atom or a chlorine atom.
  • rCiCe alkylthio group is, for example, a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, an isopentylthio group, a neopentylthio group, a 3,3-dimethylbutylthio group, It is a straight-chain or branched-chain alkylthio group having 1 to 6 carbon atoms such as a 2-ethylbutylthio group, preferably a straight-chain or branched-chain alkylthio group having 1 to 4 carbon atoms, more preferably Is a methylthio group.
  • the same or different 1 to 3 halogen atoms which may be substituted with 1 to 3 halogen atoms includes, in addition to the above-mentioned alkyl group, for example, a trifluoromethyl group, a trichloromethyl group, a difluoromethyl group.
  • CA alkyl group which may be substituted by 1 to 3 identical or different “halogen atoms”. More preferably, it is the above-mentioned "-C. Alkyl group” which may be substituted by the same or different 1 to 3 "fluorine atoms or chlorine atoms", and even more preferably, it is a methyl group, a It is a tyl group, a propyl group, a chloromethyl group or a trifluoromethyl group, particularly preferably a methyl group, an ethyl group or a trifluoromethyl group.
  • the “C i Ce alkoxy group which may be substituted with the same or different 1 to 3 halogen atoms” includes, in addition to the above “C 1 to C 6 alkoxy group”, for example, a trifluoromethoxy group , Trichloromethoxy group, difluoromethoxy group, dichloromethoxy group, dibromomethoxy group, fluoromethoxy group, chloromethoxy group, bromomethoxy group, methoxymethoxy group, 2,2,2-trichloroethoxy group, 2, 2,2-trifluoroethoxy group, 2-bromoethoxy group, 2-chloroethoxy group, 2-fluoroethoxy group, 3-chloropropoxy group, 3,3,3-trifluoropropoxy group, 4-fluorobutoxy group Group, 3-fluoro-2-methylpropoxy group, 3,3,3_trifluoro-2-methylpropoxy group, 6,6,6-tricyclohexyloxy
  • a trifluoromethoxy group Trichlorome
  • ⁇ the same or different 1 to 3 substituents selected from the group consisting of a halogen atom, a C i Ce alkoxy group and a phenoxy group, which may be substituted with ⁇ to ⁇ 6 alkyl groups '' are the other " ⁇ ⁇ 0 6 alkyl group" ⁇ Pi the "same or different 1-3 amino which may be substituted ⁇ ⁇ 6 alkyl group with a halogen atom", for example, main Tokishimechiru group, ethoxymethyl group, An ethoxy group, a propoxymethyl group or the like, the same or different from the above-mentioned ⁇ ⁇ alkyl group '' substituted by 1 to 3 ⁇ ⁇ alkoxy groups '', a phenoxymethyl group, a phenoxymethyl group or the like substituted by a phenoxy group "C 1 -C 6 alkyl group", ⁇ Pi 2 main Tokishi 1 one chloromethyl group, 3-phenoxy,
  • a ⁇ C 2 -C 6 alkenyl group which may be substituted with the same or different 1 to 3 substituents selected from the group consisting of a halogen atom, a C 1 -C 6 alkoxy group, a phenyl group and a phenoxy group "the addition of the" C 2 -C 6 alkenyl group ", 3-chloroallyl group, 4-bromo-2-heptenyl group identical or different ivy like:!
  • the ⁇ C 2 -C 6 alkynyl group which may be substituted with the same or different 1 to 3 substituents selected from the group consisting of a halogen atom, a Ci Cs alkoxy group and a phenoxy group '' is the aforementioned ⁇ other C 2 -C 6 alkynyl group ", 3- black port - 2 Puropieru group, 4- promoter 2- heptynyl said substituted with same or different 1 to 3 halogen atoms such as the group" C 2 ⁇ Substituted by 1 to 3 identical or different “-alkoxy groups” such as a C 6 alkyl group, a 3-methoxy-12-propyl group, and a 4-ethoxy-3-butulyl group.
  • the "C 2 ⁇ C 6 alkynyl group” said substituted by phenoxy groups such as 3 Fuenokishi one 2-heptynyl group "C 2 -C 6 alkynyl group”, ⁇ Pi 4 main butoxy one 4 one black port one 2 - such heptynyl group, a halogen atom, a C 1 C 6 wherein substituted by two or more substituents selected from alkoxy and the group consisting of a phenoxy group "C 2 -C 6 ⁇ Rukiniru group” also includes.
  • phenoxy groups such as 3 Fuenokishi one 2-heptynyl group "C 2 -C 6 alkynyl group”, ⁇ Pi 4 main butoxy one 4 one black port one 2 - such heptynyl group, a halogen atom, a C 1 C 6 wherein substituted by two or more substituents selected from alkoxy and the group consisting of a phenoxy group "C 2 -C 6
  • an amino group which may be substituted with the same or different one or two Ci Ce alkyl groups includes, in addition to an amino group, one or two same or different Ci Ce alkyl groups.
  • r C i C e alkyl group is an amino group substituted, preferably, identical Wakashi Ku is different 1-2 amino wherein” ⁇ ⁇ 4 alkyl group "may amino der to be substituted And more preferably a dimethylamino group or a getylamino group.
  • a ⁇ halogen atom which may be substituted with 1 to 3 identical or different 1 to 3 halogen atoms, a 6 to 6 alkyl group, a CiCe alkoxy group, 1 to 2 identical or different ⁇ Substituted with 6 alkyl groups, substituted with 1 to 6 identical or different substituents selected from the group consisting of amino groups, nitro groups, cyano groups, hydroxyl groups, mercapto groups and alkylthio groups.
  • the “aralkyl group” includes, in addition to the “aralkyl group”, the “aralkyl group” substituted with the same or different 1 to 6 halogen atoms, and the same or different 1 to 6 identical or different And the same or different 1 to 6 of the above-mentioned ⁇ ⁇ ⁇ ⁇ ⁇ -alkoxy groups which are substituted with ⁇ ⁇ ⁇ ⁇ alkyl groups which may be substituted with 1 to 3 halogen atoms.
  • the "heteroarylalkyl group which may be substituted” includes the above-mentioned “heteroarylalkyl group", and the above-mentioned “heteroarylalkyl group” substituted with the same or different 1 to 6 halogen atoms, the same or different
  • One to five Y's can be substituted at any substitutable position on the quinoline ring. When two or more Y's are present, they may be the same or different.
  • Y's When two or more Y's are present, they may be the same or different.
  • A is preferably 1 to 4 and which may be ⁇ 3 ⁇ substituted with a methyl group.
  • a cycloalkyl group more preferably a cyclopentyl group, a cyclohexyl group or a cycloheptyl group, particularly preferably a cyclohexyl group,
  • R is preferably the same or different 1 to 6 halogen atoms, a C 6 alkyl group, an alkoxy group or a dialkyl group substituted with a hydroxyl group, and more preferably the same or different A benzyl group which may be substituted with 1 to 6 different halogen atoms, a C! ⁇ 6 alkyl group, a C! CS alkoxy group or a hydroxyl group, particularly preferably a benzyl group,
  • X is preferably an oxygen atom
  • Y n is preferably ⁇ is a fluorine atom, a hydroxyl group or a methyl group, ⁇ is 0 or 1, more preferably ⁇ is a methyl group, and ⁇ is 0 Or 1.
  • ⁇ is a fluorine atom, a hydroxyl group or a methyl group, ⁇ is 0 or 1, more preferably ⁇ is a methyl group, and ⁇ is 0 Or 1.
  • Y n is Upsilon is a fluorine atom, a hydroxyl group or a methyl group, eta is 0 or 1,
  • A is a cyclopentyl group, a cyclohexyl group or a cycloheptyl group
  • R are identical or different 1-6 halogen atoms, Ci Ce alkyl group, and 0 6 alkoxy group or a hydroxyl group in base may be substituted Njiru group, (b 3) X, Oxygen atom,
  • (c1) A is a cyclohexyl group
  • Y n is Upsilon is a methyl group, eta is 0 or 1,
  • N-C 1-(3,5-difluorobenzyl) cyclohexynole] quinoline is a 3- 3-boxylboxamide.
  • the compound (I) of the present invention can be converted into a salt such as a sulfate, a hydrochloride, a nitrate, and a phosphate.
  • a salt such as a sulfate, a hydrochloride, a nitrate, and a phosphate.
  • the compound (I) of the present invention and a salt thereof can be solvated, and these solvates are also included in the present invention.
  • a solvate is preferably a hydrate.
  • the compound (I) of the present invention there is also a compound having an asymmetric carbon.
  • the present invention includes a mixture of one kind of optically active substance and several kinds of optically active substances at an arbitrary ratio. .
  • c Pen is a cyclopentyl group
  • cHe x is a cyclohexyl group
  • cHe p is a cycloheptyl group
  • No is a norbornyl group
  • cHe xe is a cyclohexyl group.
  • -Me is a methyl group
  • Et is an ethyl group
  • Pr is a propyl group
  • iPr is an isopropyl group
  • Bu is a butyl group.
  • THIM represents a thiazolylmethyl group
  • ISDM represents 4,5-dihydroisoxazolylmethyl.
  • ⁇ BZTM '' represents a benzothiazolylmethyl group
  • ⁇ NAPM '' represents a naphthylmethyl group
  • ⁇ PYDM '' represents a pyridylmethyl group
  • preferred compounds are Compound Nos. 1-11, 1-15, 1-11-1,
  • the quinoline-13-carboxamide compound of the present invention can be produced by the methods A and B described below, and the quinoline-13-carpothioamide compound can be produced by the method C described below.
  • Step A-1 is a step of producing a halogenated 3-quinoline carbonyl compound represented by the general formula (III) by halogenating compound (II) with a halogenating agent in an inert solvent. .
  • the halogenating agent used in this step is not particularly limited as long as the carboxylic acid is converted into an acid halide, and examples thereof include inorganic halogens such as phosphoryl chloride, thiol chloride, phosphorus pentachloride, and phosphorus trichloride.
  • inorganic halogens such as phosphoryl chloride, thiol chloride, phosphorus pentachloride, and phosphorus trichloride.
  • Compound; or an organic halogen compound such as ⁇ , ⁇ -dihalogenoether, halogenated alkylamine, organic phosphorus halide, or the like, preferably an organic halogen compound, and more preferably oxalyl chloride.
  • the solvent used in this step is not particularly limited as long as it does not inhibit the reaction.
  • hydrocarbons such as hexane, cyclohexane, benzene, and toluene; dichloromethane, dichloroethane, chlorohonolem, Hydrogenated hydrocarbons such as tetrachloroethane; ethers such as dioxane, getyl ether, tetrahydrofuran (THF), ethylene glycolone resin, methyl ether, etc .; acetone, methyl ethino ethyl ketone, methyl isobutyl ketone, and the like Ketones such as xanone; nitriles such as acetonitrile and isoptyronitrile; or esters such as methyl acetate, ethyl acetate and propyl acetate, and are preferably hydrocarbons or halogenated hydrocarbons.
  • the reaction temperature varies depending on the starting compound, the reaction reagent, the solvent, and the like, but is usually from 120 ° C to 250 ° C, and preferably from 0 ° C to 140 ° C.
  • the reaction time varies depending on the starting compound, the reaction reagent, the solvent, the reaction temperature and the like, but is usually 10 minutes to 120 hours, preferably 30 minutes to 72 hours.
  • step A-2 compound (IV) is acylated with compound (III) in an inert solvent in the presence or absence of a base to produce compound (la) of the present invention. This is the step of doing.
  • the amount of the compound (III) to be used is usually 1 to 3 mol, preferably 1.1 to 1.5 mol, per 1 mol of the compound (IV).
  • the base to be used is not particularly limited as long as it is used as a base in a usual reaction.
  • alkali metal carbonates such as sodium carbonate and carbon dioxide
  • Alkali metal bicarbonates such as sodium hydrogen and hydrogen bicarbonate
  • alkali metal hydrides such as sodium hydride, lithium hydride and lithium hydride
  • sodium hydroxide, lithium hydroxide and palladium hydroxide Alkali metal hydroxides or alkaline earth metal hydroxides
  • Alkali metal alkoxides such as sodium methoxide, sodium methoxide, potassium t-butoxide
  • Triethylamine, triptylamine diisopropyl , N-methylmorpholine, pyridine, 4- (N, N-dimethylamino Pyridine, N, N-Dimethylaniline, N, N-Jetylaniline, 1,5-Diazabicyclo [4.3.0]
  • the solvent used in this step is not particularly limited as long as it does not inhibit the reaction.
  • hydrocarbons such as hexane, cyclohexane, benzene, and toluene; dichloromethane, dichloroethane, chloropho / REM, and tetrachloride Hydrogenated hydrocarbons such as ethane; ethers such as dioxane, getyl ether, tetrahydrofuran (THF) ethylene glycol dimethyl ether; dimethylformamide, dimethylacetamide, hexamethylphosphate triamide (HMPA) Amides; ketones such as acetone, methylethyl ketone, methyl / isobutyl ketone, and cyclohexanone; nitrinoles such as acetonitrile and isobutyronitrile; or amides such as methyl acetate, ethyl acetate and propyl acetate Esters,
  • the reaction temperature varies depending on the starting compound, the reaction reagent, the solvent, and the like, but is usually from 20 ° C to 150 ° C, and preferably from 0 ° C to 40 ° C.
  • the reaction time varies depending on the starting compound, reaction reagent, solvent, reaction temperature and the like, but is usually 10 minutes to 120 hours, preferably 30 minutes to 72 hours.
  • the 3-quinoline carboxylic acid compound (II) as a starting material in the above-mentioned Method A is a known compound or a known method (for example, Journal Off, Medicinal Chemistry J. Med Chem. , Vol. 22, p. 816 (1979) ⁇ .
  • the amine compound (IV) used in this step is a known compound or described in a known method ⁇ for example, Chemis * Berichte Chem. Ber., Vol. 12, p. 1875 (1879).
  • a transfer reaction from the carboxylic acid, or by hydrolyzing an amide compound obtained by a Ritter reaction from an alcohol compound described in Synthesis, Vol. 12, p. 179 (2000).
  • Method II is a method for producing compound (la) of the present invention by reacting nitrile with an alcohol.
  • Step B-1 is a step for producing compound '(la) of the present invention by reacting compound (V) with compound (VI) in a solvent or a non-solvent in the presence of an acid.
  • the amount of compound (VI) to be used is generally 1 to 6 mol, preferably 1.1 to 3.0 mol, per 1 mol of compound (V).
  • the solvent to be used is not particularly limited as long as it does not inhibit the reaction.
  • hydrocarbons such as hexane, cyclohexane, and octane; dichloromethane, chloroform, Halogenated hydrocarbons such as carbon tetrachloride; ethers such as dioxane, getyl ether, tetrahydrofuran (THF), and dibutyl ether; or carboxylic acids such as acetic acid and propionic acid; Acid, more preferably acetic acid.
  • the acid used in this step is not particularly limited as long as it is used as an acid in a usual Ritter reaction.
  • inorganic acids such as sulfuric acid, formic acid, phosphoric acid, and perchloric acid; benzenesulfonic acid; It can be an organic acid such as toluenesulfonic acid; or a Lewis acid such as tin tetrachloride or trifluoroboron, preferably an inorganic acid, more preferably sulfuric acid.
  • the amount of the acid to be used is generally 1 to 6 mol, preferably 1.1 to 3 mol, per 1 mol of compound (V).
  • the reaction temperature varies depending on the starting compound, the reaction reagent, the solvent, and the like, but is usually from 20 ° C to 100 ° C, and preferably from 0 ° C to 80 ° C.
  • the reaction time varies depending on the starting compound, reaction reagent, solvent, reaction temperature and the like, but is usually 15 minutes to 120 hours, preferably 30 minutes to 72 hours.
  • the 3-quinolinecarbonitrile compound (VI), which is a starting material of the above-mentioned Method B, is a known compound or a known method (for example, Journal of Medicinal Chemistry J. Med Chem., 22 Vol. 816 (1 979) ⁇ .
  • the alcohol compound (V) used in this step is a known compound or is prepared according to a known method ⁇ for example, a method described in Tetraedron, 55, 4595 (1999) ⁇ . be able to.
  • step C-11 the compound (Ib) of the present invention is produced by reacting the compound (Ia) with a thiocarbonylating agent in a solvent or a non-solvent in the presence or absence of a base. This is the step of doing.
  • the thiocarbolating agent used in this step is not particularly limited as long as it is used in a usual thiocarbonylation reaction.
  • phosphorus pentasulfide, Lawson's reagent (2,4-bis (4- (Methoxyphenyl) 1,3-dithia-1,2,4-diphosphethane-1,2,4-disulfide), bis (dimethylamino) thiophosphoric acid or getyldithiophosphoric acid, preferably phosphorus pentasulfide Or Lawson's reagent.
  • the amount of the thiocarbolating agent to be used is generally 0.5 to 6 mol, preferably 0.5 to 3.0 mol, per 1 mol of compound (la).
  • the solvent to be used is not particularly limited as long as it does not inhibit the reaction.
  • hydrocarbons such as hexane, cyclohexane, benzene, and toluene xylene; dichloromethane; Halogenated hydrocarbons such as form and carbon tetrachloride; or ethers such as dioxane, getyl ether, tetrahydrofuran (THF), and dibutyl ether, preferably hydrocarbons, and more preferably Is toluene.
  • hydrocarbons such as hexane, cyclohexane, benzene, and toluene xylene
  • dichloromethane Halogenated hydrocarbons such as form and carbon tetrachloride
  • ethers such as dioxane, getyl ether, tetrahydrofuran (THF), and dibutyl ether, preferably hydrocarbons, and more preferably Is toluene
  • the base to be used is not particularly limited as long as it is used as a base in a usual reaction.
  • examples thereof include alkali metal carbonates such as sodium carbonate and potassium carbonate; Alkali metal bicarbonates such as sodium hydrogen, potassium bicarbonate; alkali metal hydrides such as sodium hydride, lithium hydride, lithium hydride; sodium hydroxide, lithium hydroxide, water Alkali metal hydroxides or alkaline earth metal hydroxides, such as barium oxide; alkaline metal alkoxides, such as sodium methoxide, sodium methoxide, potassium tertoxide; triethylamine, triptylamine, diisopropylethinorea Min, N-Methynolemorpholine, Pyridine, 4- (N, N-dimethylamino) pyridine, N, N-Dimethyla-line, N, N-Jetylaniline, 1,5-Diazabicyclo [4.3.0] Nonar Organic bases
  • the amount of the base to be used is usually 1 to 6 mol per 1 mol of the compound (la). ⁇ 3 moles.
  • the reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually 0 ° C to 200 ° C, and preferably 20 ° C to 180 ° C.
  • reaction time varies depending on the starting compound, reaction reagent, solvent, reaction temperature and the like, but is usually 1 hour to 120 hours, preferably 3 hours to 72 hours.
  • the target compound of each reaction can be collected from the reaction mixture according to a conventional method.
  • the reaction mixture is appropriately neutralized, and if insolubles are present, they are removed by filtration, and then an immiscible organic solvent such as water and ethyl acetate is added. It is obtained by separating the layer, drying over anhydrous magnesium sulfate or the like, and distilling off the solvent.
  • the obtained target compound can be further purified, if necessary, by a conventional method, for example, recrystallization, reprecipitation or chromatography.
  • an extraction concentrate of the reaction mixture containing the compound (I) produced in each step or a solution obtained by dissolving the compound (I) in an appropriate solvent is added to an acid.
  • Acids used in the reaction are inorganic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydrohalic acid such as hydroiodic acid, nitric acid, perchloric acid, sulfuric acid, phosphoric acid, etc .; Lower alkyls such as acid, trifluoromethanesulfonic acid and ethanesulfonic acid
  • Organic acid salts such as aryl sulfonic acid, succinic acid, and oxalic acid such as sulfonic acid, benzene sulfonic acid, and p-tonolene sulfonic acid
  • organic acid amide compounds such as saccharin.
  • the acid is used usually in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents.
  • the solvent used in the reaction is not particularly limited as long as it does not inhibit the reaction, but is preferably an ether such as ether, diisopropyl ether, tetrahydrofuran (THF) or dioxane, or an alcohol such as methanol or ethanol. Can be mentioned.
  • the reaction temperature is from 120 ° C. to 50 ° C., preferably from ⁇ 10 ° C. to 30 ° C.
  • the reaction time varies depending on the type and temperature of the solvent used, but is usually from 10 minutes to 1 hour.
  • the resulting salt is isolated by a conventional method. In other words, if it precipitates as crystals, it is isolated by filtration, and if it is water-soluble, it is isolated as an aqueous solution by separation of an organic solvent and water.
  • the compound of the present invention is useful as an active ingredient of a pesticide.
  • a pesticide for example, as an agricultural and horticultural fungicide, it has an excellent control effect on diseases caused by various plant pathogens.
  • the compound of the present invention When using the compound of the present invention, it can be formulated in various forms such as emulsions, powders, wettable powders, liquids, liquids, granules, and suspensions together with a scavenger as in the case of conventional agricultural chemicals. Can be. In the actual use of these preparations, they can be used as they are, or can be used after being diluted to a predetermined concentration with a diluent such as water.
  • the adjuvant used examples include a carrier, an emulsifier, a suspending agent, a dispersing agent, a spreading agent, a penetrating agent, a wetting agent, a thickening agent, and a stabilizer, and these can be added as needed.
  • Carriers used are divided into solid carriers and liquid carriers.
  • Solid carriers are starch, sugar, Animal and plant powders such as cellulose powder, cyclodextrin, activated carbon, soy flour, wheat flour, rice flour, wood flour, fish meal, milk powder; or tanolek, kaolin, bentonite, organic bentonite, calcium carbonate, calcium sulfate, bicarbonate Sodium, zeolite, diatomaceous earth, white carbon, clay, alumina, silica, mineral powders such as sulfur powders and the like, and the liquid carrier is water; animal and vegetable oils such as soybean oil, cottonseed oil, corn oil; Alcohols such as ethyl alcohol and ethylene glycol; Ketones such as acetone and methyl ethyl ketone; Ethers such as dioxane and tetrahydrofuran; kerosene, kerosene, liquid paraffin, xylene, trimethylbenzene, tetramethynobenzene, and cyclohexane
  • the compounding mass ratio of the compound of the present invention and the adjuvant is usually 0.05: 99.95 to 90:10, preferably 0.2: 99.8 to 80:20.
  • the concentration or amount used of the compound of the present invention varies depending on the target crop, the method of use, the formulation, the amount applied, and the like.
  • it is usually 0.1 to 10,000 ppm per active ingredient, and is preferably l to 1000 ppm, and in the case of soil treatment, usually 10 to 1 OOOOO g Zha, preferably 200 to 20000 g / ha.
  • the compound of the present invention may be mixed with or used in combination with other pesticides, if necessary, such as insecticides, acaricides, attractants, nematicides, fungicides, antiviral agents, herbicides, plant growth regulators, etc. It is preferably an insecticide, acaricide, nematicide or fungicide.
  • the insecticide, acaricide or nematicide used is, for example, ⁇ - (4-promo 2-chlorophenyl) O-ethyl S-propylphosphorothioate (generic name: prophenophos), O— (2 , 2-dichloro vinyl) O, di-dimethyl phosphate (general name: dichlorvos), O-ethyl O— ⁇ 3-methyl-4- (methylthio) phenyl ⁇ N-isopropyl phosphoramidate Name: Fenamiphos), O, O—Dimethyl O— (4-Etro-1 m—Tolyl) phosphorothioate (generic name: uetrothion), O—ethyl O— (4-nitrophenyl) phenylphosphonothioate (generic name: EPN), O, O— Jetyl ⁇ -I (2-Isopropyl -1-6-Methylpyrimidine 4-1yl) phosphorot
  • the fungicides used are, for example, 2-anilino-4-methyl-16- (1-propyl) pyrimidine (generic name: mepanipyrim), 4,6-dimethyl-1-N-phenyl-12-pyrimidinamine (generic name: Pyrimidinamine-based compounds such as pyrimesanil); 1- (4-chlorophenoxy) _3, "3-dimethyl-11- (1H-1,2,4-triazole-11-yl) butanone (generic name: Triadimefon), 1-(biphenyl-1-yloxy) -1,3,3-Dimethylyl 1-1 (1H, 1,2,4-triazole-1-yl) Butan-1-ol (generic name: bitertanol), 1 1 ⁇ N— (4-black mouth _ 2—trifluoromethylphenol) 1 2—propoxyacetoimidone ⁇ imidazole (generic name: triflumizone), 1 1 ⁇ 2-(2, 4-dich
  • N-halogenothioalkyl compounds such as (generic name: captaphore), N- (trichloromethylthio) phthalimid (generic name: phthalate);
  • iprodione such as (RS) —3- (3,5-dichlorophenyl) -1-methyl-5-vinyl-1,1,3-oxazolidine-1,4-dione (generic name: vinclozolin)
  • Dicarboxyimide compounds ⁇ , a, ⁇ ; -trifluoro-3'-isopropoxy_ ⁇ -tolu-lide (generic name: flutranil), 3'-isopropoxy- ⁇ -toluanilide (generic name: mepronil) N, N '— [piperazine-1,4-diylbis ⁇ (trichloromethyl) methylene ⁇ ] piperazine-based compound such as diformamide (generic name: trifolin); 2', 4 ' Pyridine compounds such as —dichloro-2- (3-pyridyl) acetophenone ⁇ —methyloxime (generic name: pyrifenox);
  • Morpholin compounds such as 2,6-dimethylmorpholine (generic name: fenpropimorph); trifruerutin hydroxide (generic name: fentinhi) Organotin compounds such as droxide) and trifenyltin acetate (generic name: fentin acetate); 1- (4-cyclopentene) 1-cyclopentinole 3-phenylphenylrea
  • Cinamic acid-based compounds such as (4-—mouth opening) 1-3— (3,4-dimethoxyphenyl) acryloyl ⁇ morpholine (generic name: dimethomorph); Phenylcarbamate-based compounds such as propyl 3,4-diethoxycarbarate (generic name: diethofencarp); 3-cyano 4- (2,2-divinyl 1,3-benzodioxol-4-4-) G) Pyranol (generic name: fludioxonil), 3- ⁇ 2 ', 3'-dichloromouth phenyl), and cyanovirol-based compounds such as 4-cyanovirol (generic name: fenpicrol).
  • Example 1 Cinamic acid-based compounds such as (4-—mouth opening) 1-3— (3,4-dimethoxyphenyl) acryloyl ⁇ morpholine (generic name: dimethomorph); Phenylcarbamate-based compounds such as propyl 3,4
  • Example 2 The compound of Example 2 (10 parts by mass) was dissolved in a mixed solution of xylene (40 parts by mass, manufactured by Wako Pure Chemical Industries, Ltd.) and DMSO (35 parts by mass, manufactured by Wako Pure Chemical Industries, Ltd.).
  • An arako 1 KPS mixture of anionic surfactant and Noun surfactant, manufactured by Nippon Emulsifier Co., Ltd., 25 parts by mass was added and mixed to obtain an emulsion.
  • the obtained granules are dried with a shelf type dryer (PERFECT OVEN PS-222, manufactured by Tabai Co., Ltd., 60 ° C), and then sieved to 600 to 1,180 m to obtain granules.
  • a shelf type dryer (PERFECT OVEN PS-222, manufactured by Tabai Co., Ltd., 60 ° C)
  • a test plant for pot cultivation (rice: Kofu) at the 3rd to 4th leaf stage was sprayed and inoculated with a suspension of pathogenic spores, and the pot was placed in an inoculation room at room temperature of 20 to 23 ° C to promote the disease.
  • the compound of the present invention was dissolved in a mixed solution of dimethyl sulfoxide methanol (volume ratio: 7Z3), and a spray liquid containing the compound of the present invention at 30 Oppm was prepared and uniformly sprayed on the pot. The severity of the disease 7 days after the inoculation was investigated. The test was performed in duplicate.
  • the degree of disease was determined by observing the degree of disease of the test plant with the naked eye, judging based on the following criteria, and expressed in four stages from 0 to 3.
  • Severity 0 No disease at all.
  • Example 1 (Compound No. 1-111), Example 2 (Compound No. 1-117), Example 3 (Compound No. 1-152), Example 5 (Compound No. 1-112) ), Example 6 (Compound No. 11-13), Example 7 (Compound No. 11-14), Example 9 (Compound No. 1-116), Example 10 (Compound No. 11-30) ), Example 11 (Compound No. 1-132), Example 14 (Compound No. 1-144), Example 17 (Compound No. 1-167), Example 18 (Compound No. 1-171) , Example 19 (Compound No. 1-173), Example 20 (Compound No. 1-174), Example 24 (Compound No. 1-135), Example 26 (Compound No. 1-18), Example 2 7 (Compound No. 1-19), Example
  • the compound of 90 (Compound No. 1-1246) had no disease onset.
  • Test example 2 The compound of 90 (Compound No. 1-1246) had no disease onset.
  • the degree of disease was determined by observing the degree of disease of the test plant with the naked eye, judging based on the following criteria, and expressed in four stages from 0 to 3.
  • Severity 0 No disease at all.
  • Example 1 (Compound No. 1-11), Example 2 (Compound No. 1-117), Example 3 (Compound No. 1-152), Example 4 (Compound No. 1-11), Example 5 (Compound Nos. 1-112), Example 7 (Compound No. 1-114), Example 8 (Compound No. 1-115), Example 9 (Compound No. 1-116), Example 10 (Compound No. No. 1-30), Example 11 (Compound No. 1-32), Example 14 (Compound No. 1-144), Example 17 (Compound No. 1-167), Example 18 (Compound No. 1-171) , Example 19 (Compound No. 1-173), Example 20 (Compound No. 1-174), Example 22 (Compound No. 1-123), Example 24 (Compound No.
  • Example 27 Example 27 Compound No. 1-119
  • Example 28 Compound No. 1-120
  • Example 30 Compound No. 1-28)
  • Example 36 Compound No. 1-15
  • Example 39 Compound No. 1
  • Example 75 Compound No. 1-177
  • Example 41 Compound No. 1-178
  • Example 45 Compound No. 1-139
  • Example 46 Compound No. 1-146
  • Example 49 Compound No. 1-156
  • Example 62 Compound No. 1-156
  • Compound No. 1-199 Example 63 (Compound No. 1-1200)
  • Example 67 Compound No. 1-208
  • Example 68 Compound No. 1-1210
  • Example 71 Compound No. 1-121) 3
  • Example 72 Compound No.
  • Example 73 (Compound No. 1-219), Example 74 (Compound No. 1-1220), Example 75 (Compound No. 1-221), Example 76 (Compound No. 1-222), Example 8 1 (Compound No. 1-235) ), Example 87 (Compound Nos. 1-1241), Example 91 (Compound Nos. 1-247), and Example 92 (Compound Nos. 1-248) had no disease onset.
  • the compound of the present invention can be used as a fungicide for agricultural and horticultural use, and has excellent effects on various phytopathogenic fungi, especially rice blast, without damaging host plants. It is excellent.
  • plant diseases on which the compound of the present invention exerts excellent efficacy include, for example, rice blast (Pyricularia oryzae) and gray mold (Botrytis cinerea) of cucumber, tomato and kidney bean. Cultrums are not limited to these.

Landscapes

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

Abstract

L'invention concerne un composé présentant une excellente activité bactéricide contre diverses maladies végétales, ou un de ses sels, pouvant être utilisé comme ingrédient actif dans un produit chimique agricole destiné à la lutte contre la piriculariose du riz, etc., lorsqu'il est utilisé à petite dose. Ce composé est représenté par la formule générale (I) dans laquelle A désigne un cycloalkyle C3-10 ou un cycloalcényle C3-10 ; R désigne un alkyle C1-6, un alcényle C2-6, un alcynyle C2-6, un aralkyle, ou un hétéroarylalkyle ; X désigne un atome d'oxygène ou de soufre ; Y désigne un substituant sélectionné dans le groupe comprenant un halogéno, un alkyle C1-6, un alcoxy C1-6, un phényle, un phénoxy, un acyloxy C1-7, un amino, un nitro, un hydroxy, un mercapto et un alkylthio C1-6 ; et n désigne un entier compris entre 0 et 5.
PCT/JP2003/013417 2002-10-21 2003-10-21 Compose a base de quinoline-3-carboxamide WO2004039783A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2004548028A JP4511362B2 (ja) 2002-10-21 2003-10-21 キノリン−３−カルボキサミド化合物
AU2003273064A AU2003273064A1 (en) 2002-10-21 2003-10-21 Quinoline-3-carboxamide compound

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2002305696 2002-10-21
JP2002-305696 2002-10-21

Publications (1)

Publication Number Publication Date
WO2004039783A1 true WO2004039783A1 (fr) 2004-05-13

Family

ID=32211560

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2003/013417 WO2004039783A1 (fr) 2002-10-21 2003-10-21 Compose a base de quinoline-3-carboxamide

Country Status (4)

Country Link
JP (1) JP4511362B2 (fr)
AU (1) AU2003273064A1 (fr)
TW (1) TWI314041B (fr)
WO (1) WO2004039783A1 (fr)

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005206517A (ja) * 2004-01-22 2005-08-04 Sankyo Agro Kk １−アラルキルシクロヘキサン化合物
WO2009057668A1 (fr) * 2007-10-31 2009-05-07 Sumitomo Chemical Company, Limited Composé d'amide et agent d'élimination d'une maladie des plantes l'utilisant
US8101767B2 (en) 2004-06-24 2012-01-24 Vertex Pharmaceuticals Incorporated Modulators of ATP-binding cassette transporters
US8354427B2 (en) 2004-06-24 2013-01-15 Vertex Pharmaceutical Incorporated Modulators of ATP-binding cassette transporters
US8410274B2 (en) 2005-12-28 2013-04-02 Vertex Pharmaceuticals Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
US8802700B2 (en) 2010-12-10 2014-08-12 Vertex Pharmaceuticals Incorporated Modulators of ATP-Binding Cassette transporters
US9701639B2 (en) 2014-10-07 2017-07-11 Vertex Pharmaceuticals Incorporated Co-crystals of modulators of cystic fibrosis transmembrane conductance regulator
US9751839B2 (en) 2009-03-20 2017-09-05 Vertex Pharmaceuticals Incorporated Process for making modulators of cystic fibrosis transmembrane conductance regulator
WO2017153380A1 (fr) 2016-03-10 2017-09-14 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
WO2018054721A1 (fr) * 2016-09-26 2018-03-29 Basf Se Composés de pyridine pour lutter contre des champignons phytopathogenes nocifs
WO2018054711A1 (fr) * 2016-09-26 2018-03-29 Basf Se Composés de pyridine pour lutter contre des champignons nocifs phytopathogènes
EP3447048A1 (fr) 2017-08-23 2019-02-27 Syngenta Participations Ag Dérivés de quinoline (thio)carboxamide microbiocides
WO2019053010A1 (fr) 2017-09-13 2019-03-21 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
WO2019053019A1 (fr) 2017-09-13 2019-03-21 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
WO2019053026A1 (fr) 2017-09-13 2019-03-21 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
WO2019053024A1 (fr) 2017-09-13 2019-03-21 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
WO2019052930A1 (fr) 2017-09-13 2019-03-21 Syngenta Participations Ag Compositions fongicides
WO2019053015A1 (fr) 2017-09-13 2019-03-21 Syngenta Participations Ag Dérivés microbiocides de quinoline (thio)carboxamide
WO2019053027A1 (fr) 2017-09-13 2019-03-21 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
WO2019053016A1 (fr) 2017-09-13 2019-03-21 Syngenta Participations Ag Dérivés microbiocides de quinoline (thio)carboxamide
US10272046B2 (en) 2012-02-27 2019-04-30 Vertex Pharmaceuticals Incorporated Pharmaceutical composition and administrations thereof
WO2020064696A1 (fr) 2018-09-26 2020-04-02 Syngenta Crop Protection Ag Compositions fongicides
US10646481B2 (en) 2008-08-13 2020-05-12 Vertex Pharmaceuticals Incorporated Pharmaceutical composition and administrations thereof
WO2023112056A1 (fr) 2021-12-17 2023-06-22 Pi Industries Ltd. Nouveaux composés de pyridine carboxamide bicycliques fusionnés substitués pour lutter contre des champignons phytopathogènes

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991014677A1 (fr) * 1990-03-28 1991-10-03 Otsuka Pharmaceutical Co., Ltd. Derive de quinoline, medicament anti-ulcereux contenant ce derive et production de ce derive
US5346907A (en) * 1988-04-05 1994-09-13 Abbott Laboratories Amino acid analog CCK antagonists
WO1995014668A1 (fr) * 1993-11-26 1995-06-01 Tanabe Seiyaku Co., Ltd. Derive de 2-oxoindoline
JPH0940557A (ja) * 1995-05-25 1997-02-10 Tanabe Seiyaku Co Ltd 医薬組成物
WO2000073283A1 (fr) * 1999-06-02 2000-12-07 Nps Pharmaceuticals, Inc. Antagonistes du recepteur de glutamate metabotropique et leur utilisation pour le traitement de maladies du systeme nerveux central
WO2002088086A1 (fr) * 2001-04-24 2002-11-07 Sankyo Company, Limited Derive de n-(3-quinolyl)amide

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61126071A (ja) * 1984-11-22 1986-06-13 Hokko Chem Ind Co Ltd 農園芸用殺菌剤
DE3814505A1 (de) * 1988-04-29 1989-11-09 Bayer Ag Substituierte cycloalkyl- bzw. heterocyclyl-carbonsaeureanilide
US5399564A (en) * 1991-09-03 1995-03-21 Dowelanco N-(4-pyridyl or 4-quinolinyl) arylacetamide and 4-(aralkoxy or aralkylamino) pyridine pesticides
TW200409757A (en) * 2002-07-08 2004-06-16 Sankyo Agro Co Ltd 1-aralkyl-N-(3-quinolyl)-1-cyclohexancarboxamide derivatives

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5346907A (en) * 1988-04-05 1994-09-13 Abbott Laboratories Amino acid analog CCK antagonists
WO1991014677A1 (fr) * 1990-03-28 1991-10-03 Otsuka Pharmaceutical Co., Ltd. Derive de quinoline, medicament anti-ulcereux contenant ce derive et production de ce derive
WO1995014668A1 (fr) * 1993-11-26 1995-06-01 Tanabe Seiyaku Co., Ltd. Derive de 2-oxoindoline
JPH0940557A (ja) * 1995-05-25 1997-02-10 Tanabe Seiyaku Co Ltd 医薬組成物
WO2000073283A1 (fr) * 1999-06-02 2000-12-07 Nps Pharmaceuticals, Inc. Antagonistes du recepteur de glutamate metabotropique et leur utilisation pour le traitement de maladies du systeme nerveux central
WO2002088086A1 (fr) * 2001-04-24 2002-11-07 Sankyo Company, Limited Derive de n-(3-quinolyl)amide

Cited By (71)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4511201B2 (ja) * 2004-01-22 2010-07-28 三井化学アグロ株式会社 １−アラルキルシクロヘキサン化合物
JP2005206517A (ja) * 2004-01-22 2005-08-04 Sankyo Agro Kk １−アラルキルシクロヘキサン化合物
US8829204B2 (en) 2004-06-24 2014-09-09 Vertex Pharmaceuticals Incorporated Modulators of ATP-binding cassette transporters
US10662192B2 (en) 2004-06-24 2020-05-26 Vertex Pharmaceuticals Incorporated Modulators of ATP-binding cassette transporters
US8101767B2 (en) 2004-06-24 2012-01-24 Vertex Pharmaceuticals Incorporated Modulators of ATP-binding cassette transporters
US8324242B2 (en) 2004-06-24 2012-12-04 Vertex Pharmaceutical Incorporated Modulators of ATP-binding cassette transporters
US8354427B2 (en) 2004-06-24 2013-01-15 Vertex Pharmaceutical Incorporated Modulators of ATP-binding cassette transporters
US8614327B2 (en) 2004-06-24 2013-12-24 Vertex Pharmaceuticals Incorporated Modulators of ATP-binding cassette transporters
US8629162B2 (en) 2004-06-24 2014-01-14 Vertex Pharmaceuticals Incorporated Modulators of ATP-binding cassette transporters
US8741925B2 (en) 2004-06-24 2014-06-03 Vertex Pharmaceuticals Incorporated Modulators of ATP-binding cassette transporters
US9090619B2 (en) 2004-06-24 2015-07-28 Vertex Pharmaceuticals Incorporated Modulators of ATP-binding cassette transporters
US8410274B2 (en) 2005-12-28 2013-04-02 Vertex Pharmaceuticals Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
US9931334B2 (en) 2005-12-28 2018-04-03 Vertex Pharmaceuticals Incorporated Solid forms of N[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
US8754224B2 (en) 2005-12-28 2014-06-17 Vertex Pharmaceuticals Incorporated Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
US9139530B2 (en) 2005-12-28 2015-09-22 Vertex Pharmaceuticals Incorporated Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
US9670163B2 (en) 2005-12-28 2017-06-06 Vertex Pharmaceuticals Incorporated Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
US10537565B2 (en) 2005-12-28 2020-01-21 Vertex Pharmaceuticals Incorporated Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
US11291662B2 (en) 2005-12-28 2022-04-05 Vertex Pharmaceuticals Incorporated Solid forms of n-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
WO2009057668A1 (fr) * 2007-10-31 2009-05-07 Sumitomo Chemical Company, Limited Composé d'amide et agent d'élimination d'une maladie des plantes l'utilisant
US11564916B2 (en) 2008-08-13 2023-01-31 Vertex Pharmaceuticals Incorporated Pharmaceutical composition and administrations thereof
US10646481B2 (en) 2008-08-13 2020-05-12 Vertex Pharmaceuticals Incorporated Pharmaceutical composition and administrations thereof
US9751839B2 (en) 2009-03-20 2017-09-05 Vertex Pharmaceuticals Incorporated Process for making modulators of cystic fibrosis transmembrane conductance regulator
US8802700B2 (en) 2010-12-10 2014-08-12 Vertex Pharmaceuticals Incorporated Modulators of ATP-Binding Cassette transporters
US11752106B2 (en) 2012-02-27 2023-09-12 Vertex Pharmaceuticals Incorporated Pharmaceutical composition and administrations thereof
US11147770B2 (en) 2012-02-27 2021-10-19 Vertex Pharmaceuticals Incorporated Pharmaceutical composition and administrations thereof
US10272046B2 (en) 2012-02-27 2019-04-30 Vertex Pharmaceuticals Incorporated Pharmaceutical composition and administrations thereof
US9701639B2 (en) 2014-10-07 2017-07-11 Vertex Pharmaceuticals Incorporated Co-crystals of modulators of cystic fibrosis transmembrane conductance regulator
WO2017153380A1 (fr) 2016-03-10 2017-09-14 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
JP2019509291A (ja) * 2016-03-10 2019-04-04 シンジェンタ パーティシペーションズ アーゲー 殺微生物性キノリン（チオ）カルボキサミド誘導体
TWI713704B (zh) * 2016-03-10 2020-12-21 瑞士商先正達合夥公司 殺微生物的喹啉（硫代）羧醯胺衍生物
WO2018054721A1 (fr) * 2016-09-26 2018-03-29 Basf Se Composés de pyridine pour lutter contre des champignons phytopathogenes nocifs
WO2018054711A1 (fr) * 2016-09-26 2018-03-29 Basf Se Composés de pyridine pour lutter contre des champignons nocifs phytopathogènes
WO2019038189A1 (fr) 2017-08-23 2019-02-28 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
JP7184875B2 (ja) 2017-08-23 2022-12-06 シンジェンタ パーティシペーションズ アーゲー 殺微生物性キノリン（チオ）カルボキサミド誘導体
US11185073B2 (en) 2017-08-23 2021-11-30 Syngenta Participations Ag Microbiocidal quinoline (thio)carboxamide derivatives
EP3447048A1 (fr) 2017-08-23 2019-02-27 Syngenta Participations Ag Dérivés de quinoline (thio)carboxamide microbiocides
JP2020531534A (ja) * 2017-08-23 2020-11-05 シンジェンタ パーティシペーションズ アーゲー 殺微生物性キノリン（チオ）カルボキサミド誘導体
US11129386B2 (en) 2017-09-13 2021-09-28 Syngenta Participations Ag Microbiocidal quinoline (thio)carboxamide derivatives
CN111107745B (zh) * 2017-09-13 2021-12-07 先正达参股股份有限公司 杀真菌组合物
CN111107745A (zh) * 2017-09-13 2020-05-05 先正达参股股份有限公司 杀真菌组合物
CN111148736A (zh) * 2017-09-13 2020-05-12 先正达参股股份有限公司 杀微生物的喹啉（硫代）甲酰胺衍生物
WO2019053010A1 (fr) 2017-09-13 2019-03-21 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
CN111093372A (zh) * 2017-09-13 2020-05-01 先正达参股股份有限公司 杀微生物的喹啉(硫代)羧酰胺衍生物
CN111050558A (zh) * 2017-09-13 2020-04-21 先正达参股股份有限公司 杀微生物的喹啉(硫代)羧酰胺衍生物
JP2020533390A (ja) * 2017-09-13 2020-11-19 シンジェンタ パーティシペーションズ アーゲー 殺微生物性キノリン（チオ）カルボキサミド誘導体
JP2020533355A (ja) * 2017-09-13 2020-11-19 シンジェンタ パーティシペーションズ アーゲー 殺微生物性キノリン（チオ）カルボキサミド誘導体
JP2020533388A (ja) * 2017-09-13 2020-11-19 シンジェンタ パーティシペーションズ アーゲー 殺微生物性キノリン（チオ）カルボキサミド誘導体
WO2019052930A1 (fr) 2017-09-13 2019-03-21 Syngenta Participations Ag Compositions fongicides
US11744246B2 (en) 2017-09-13 2023-09-05 Syngenta Participations Ag Preparation of mammalian oocyte for fertilization via a soluble human PH20 hyaluronidase polypeptide
WO2019053024A1 (fr) 2017-09-13 2019-03-21 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
WO2019053019A1 (fr) 2017-09-13 2019-03-21 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
US11178869B2 (en) 2017-09-13 2021-11-23 Syngenta Participations Ag Microbiocidal quinoline (thio)carboxamide derivatives
US11185074B2 (en) 2017-09-13 2021-11-30 Syngenta Participations Ag Microbiocidal quinoline (thio)carboxamide derivatives
WO2019053026A1 (fr) 2017-09-13 2019-03-21 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
CN111094247A (zh) * 2017-09-13 2020-05-01 先正达参股股份有限公司 杀微生物的喹啉(硫代)甲酰胺衍生物
US11234437B2 (en) 2017-09-13 2022-02-01 Syngenta Participations Ag Fungicidal compositions
US11266146B2 (en) 2017-09-13 2022-03-08 Syngenta Participations Ag Microbiocidal quinoline (thio)carboxamide derivatives
WO2019053016A1 (fr) 2017-09-13 2019-03-21 Syngenta Participations Ag Dérivés microbiocides de quinoline (thio)carboxamide
CN111050558B (zh) * 2017-09-13 2022-05-27 先正达参股股份有限公司 杀微生物的喹啉(硫代)羧酰胺衍生物
CN111093372B (zh) * 2017-09-13 2022-05-27 先正达参股股份有限公司 杀微生物的喹啉(硫代)羧酰胺衍生物
JP7150009B2 (ja) 2017-09-13 2022-10-07 シンジェンタ パーティシペーションズ アーゲー 殺微生物性キノリン（チオ）カルボキサミド誘導体
TWI780224B (zh) * 2017-09-13 2022-10-11 瑞士商先正達合夥公司 殺真菌組成物
WO2019053027A1 (fr) 2017-09-13 2019-03-21 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
JP7258859B2 (ja) 2017-09-13 2023-04-17 シンジェンタ パーティシペーションズ アーゲー 殺微生物性キノリン（チオ）カルボキサミド誘導体
JP7202367B2 (ja) 2017-09-13 2023-01-11 シンジェンタ パーティシペーションズ アーゲー 殺微生物性キノリン（チオ）カルボキサミド誘導体
WO2019053015A1 (fr) 2017-09-13 2019-03-21 Syngenta Participations Ag Dérivés microbiocides de quinoline (thio)carboxamide
US11584740B2 (en) 2017-09-13 2023-02-21 Syngenta Participations Ag Microbiocidal quinoline (thio)carboxamide derivatives
CN112770632B (zh) * 2018-09-26 2022-12-27 先正达农作物保护股份公司 杀真菌组合物
CN112770632A (zh) * 2018-09-26 2021-05-07 先正达农作物保护股份公司 杀真菌组合物
WO2020064696A1 (fr) 2018-09-26 2020-04-02 Syngenta Crop Protection Ag Compositions fongicides
WO2023112056A1 (fr) 2021-12-17 2023-06-22 Pi Industries Ltd. Nouveaux composés de pyridine carboxamide bicycliques fusionnés substitués pour lutter contre des champignons phytopathogènes

Also Published As

Publication number Publication date
TWI314041B (en) 2009-09-01
JP4511362B2 (ja) 2010-07-28
JPWO2004039783A1 (ja) 2006-03-02
TW200410633A (en) 2004-07-01
AU2003273064A1 (en) 2004-05-25

Similar Documents

Publication Publication Date Title
WO2004039783A1 (fr) Compose a base de quinoline-3-carboxamide
TW577883B (en) Tetrazoyloxime derivative and agricultural chemical comprising the same as active ingredient
EP2030971B1 (fr) Agent de lutte antiparasite contenant un nouveau dérivé de pyridyl-méthanamine ou un sel de celui-ci
JP2009143951A (ja) 酸アミド誘導体、それらの製造方法及びそれらを含有する有害生物防除剤
JP6133907B2 (ja) 縮合環ピリミジン化合物及びそれを含む有害生物防除剤
JPH10324687A (ja) ピロール化合物、製法および農園芸用殺菌剤
WO2021085370A1 (fr) Dérivé azole et son utilisation
JP2606720B2 (ja) イミダゾール系化合物及びそれらを含有する有害生物防除剤
JP4300009B2 (ja) 酸アミド誘導体、それらの製造方法及びそれらを含有する有害生物防除剤
JP6895187B2 (ja) 新規ベンジルアミド化合物、その製造方法、及び殺ダニ剤
JP2007001944A (ja) ３，４−ジヒドロ−１，３’−ビキノリン−２−オン誘導体
KR20110082175A (ko) 피리딘 유도체 또는 그의 염, 이들을 함유하는 유해 생물 방제제 및 이의 제조 방법
JP2008088139A (ja) ３−置換キノリン化合物
JPWO2004005261A1 (ja) １−アラルキル−ｎ−（３−キノリル）−１−シクロヘキサンカルボキサミド誘導体
JP6847858B2 (ja) 除草化合物
TW201127291A (en) Diaryltriazole derivative or its salt; insecticide, miticide, nematicide or soil pesticide containing it; and process for its production
JP2004269449A (ja) ベンズアミド誘導体、それらの製造方法及びそれらを含有する有害生物防除剤
JP4511201B2 (ja) １−アラルキルシクロヘキサン化合物
AU2019278527C1 (en) Pyrazole derivative and harmful organism-controlling agent
WO2021068815A1 (fr) Composé ester d'acide carboxylique et son application
WO2002064566A1 (fr) Composes d'oxime o-ether et fongicides a usage agricole et horticole
JP2004143045A (ja) Ｎ−（３−キノリル）アミド誘導体を含有する農薬
JP2006232814A (ja) アントラニルアミド系化合物、それらの製造方法及びそれらを含有する有害生物防除剤
JP2004091474A (ja) １−アラルキル−ｎ−（３−キノリル）−１−シクロヘキサンカルボキサミド誘導体
WO2022107724A1 (fr) Dérivé d'azétidinone et herbicide en contenant en tant que principe actif

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2004548028

Country of ref document: JP

122 Ep: pct application non-entry in european phase