WO2010018868A1 - Agent antiparasitaire contenant un dérivé triazolopyrimidine ou un sel de celui-ci - Google Patents

Agent antiparasitaire contenant un dérivé triazolopyrimidine ou un sel de celui-ci Download PDF

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Publication number
WO2010018868A1
WO2010018868A1 PCT/JP2009/064359 JP2009064359W WO2010018868A1 WO 2010018868 A1 WO2010018868 A1 WO 2010018868A1 JP 2009064359 W JP2009064359 W JP 2009064359W WO 2010018868 A1 WO2010018868 A1 WO 2010018868A1
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formula
alkyl
compound
reaction
optionally substituted
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PCT/JP2009/064359
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English (en)
Japanese (ja)
Inventor
一浩 山元
剛 上田
寿彦 植木
和久 桐山
幸太郎 吉田
久樹 田中
哲也 小玉
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石原産業株式会社
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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A61P33/06—Antimalarials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • A61P33/12—Schistosomicides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • the present invention relates to a novel pest control agent containing a triazolopyrimidine derivative or a salt thereof as an active ingredient.
  • Patent Documents 1 and 2 describe triazolopyrimidine derivatives used for the production of dyes. Non-Patent Documents 1 and 2 also describe that triazolopyrimidine derivatives have herbicidal activity. However, these documents do not describe the use of triazolopyrimidine derivatives as insecticides, acaricides, nematicides or soil insecticides or animal parasite control agents. Furthermore, there is no specific description of the triazolopyrimidine derivative represented by the following formula (I- ⁇ ).
  • An object of the present invention is to provide a pest control agent that can control various pests that cause problems in the field of agriculture and horticulture and pests that parasitize animals without any disadvantages such as limited use.
  • the present inventors have made various studies on triazolopyrimidine derivatives in order to find better pest control agents. As a result, the present inventors have found that the triazolopyrimidine derivative represented by the following formula (I) has a very high control effect against pests with a low dose, and completed the present invention.
  • the present invention has the formula (I):
  • R 1 is a hydrogen atom, alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen, cyano , Aryl optionally substituted with halogen, heterocyclic group optionally substituted with alkyl, C ⁇ NOR 2 , C ⁇ NNR 4 R 5 , COR 2 , COOR 2 , OR 2 , S (O) n R 3 , NR 4 R 5 , N 3 or CONR 4 R 5 ;
  • X is alkyl, hydroxyalkyl, alkenyl, alkynyl, aryl, halogen, haloalkyl, cyano, nitro, NR 4 R 5 , S (O) n R 3 , OR 2 , COR 2 , COOR 2 or CONR 4 R 5 ;
  • Y is a hydrogen atom or a fluorine atom;
  • Z is CH,
  • R 1 ⁇ is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen, cyano, halogen Aryl which may be substituted, heterocyclic group which may be substituted with alkyl, C ⁇ NOR 2 , C ⁇ NNR 4 R 5 , COR 2 , COOR 2 , OR 2 , S (O) n R 3 or CONR 4 R It is 5;
  • X is an alkyl, hydroxyalkyl, alkenyl, alkynyl, aryl, halogen, haloalkyl, cyano, nitro, NR 4 R 5, S ( O) n R 3, oR 2, COR 2, COOR 2 or CONR 4 R It is 5;
  • Y is a hydrogen atom or a fluorine atom;
  • Z is CH, CX or n;
  • A is a halogen, oR
  • M is an integer from 1 to 4; n is an integer from 0 to 2; provided that (1) when R 1 ⁇ is methyl, X is 4-methoxy, and Z is CH, (2 ) R 1 ⁇ is methyl, X is 3,4-dimethoxy, Z is CH, and (3) R 1 ⁇ is methyl, X is 4-methyl, and Z is CH.
  • New It relates rear triazolopyrimidine derivative or a salt thereof.
  • the pest control agent comprising the triazolopyrimidine derivative of the formula (I) or a salt thereof as an active ingredient has a very high control effect against pests at a low dose.
  • each X may be the same or different.
  • halogen in formula (I) or the halogen as a substituent examples include each atom of fluorine, chlorine, bromine or iodine.
  • the number of halogens as a substituent may be 1 or 2 or more, and in the case of 2 or more, each halogen may be the same or different. Further, the halogen substitution position may be any position.
  • the alkyl in the formula (I) may be linear or branched, for example, C 1-6 such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, etc. Can be mentioned.
  • cycloalkyl in formula (I) examples include C 3-6 such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • the alkenyl in the formula (I) may be linear or branched, such as vinyl, 1-propenyl, allyl, isopropenyl, 1-butenyl, 1,3-butadienyl, 1-hexenyl and the like. C 2-6 may be mentioned.
  • the alkynyl in the formula (I) may be linear or branched.
  • Examples of the aryl in the formula (I) include C 6-10 aryl such as phenyl and naphthyl.
  • the heterocyclic group in the formula (I) includes a condensed heterocyclic group in addition to a monocyclic heterocyclic group.
  • Monocyclic heterocyclic groups include, for example, 3-membered heterocyclic groups such as oxiranyl; furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, dioxolanyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl 5-membered heterocyclic groups such as pyrazolinyl, pyrazolidinyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl; 6-membered heterocyclic groups such as pyranyl, pyridyl, piperidinyl, dioxanyl,
  • a 5- or 6-membered heterocyclic group containing 1 to 4 atoms of at least one atom selected from the group consisting of O, S and N is desirable.
  • the condensed heterocyclic group include benzofuranyl, isobenzofuranyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, benzothienyl, isobenzothienyl, dihydrobenzothienyl, dihydroisobenzothienyl, tetrahydrobenzothienyl, indolyl, isoindolyl, Benzoxazolyl, benzothiazolyl, indazolyl, benzimidazolyl, benzodioxolanyl, benzodioxanyl, chromenyl, chromanyl, isochromanyl, chromonyl, chromanonyl, quinolyl, isoquinolyl, cin
  • Examples of the salt of the triazolopyrimidine derivative of the formula (I) include any agriculturally acceptable salt, for example, ammonium salts such as dimethylammonium salt and triethylammonium salt; Examples thereof include inorganic acid salts such as acid salts, sulfates and nitrates; organic acid salts such as acetates and methanesulfonates.
  • the present invention includes both isomers and isomer mixtures.
  • isomers are described as a mixture unless otherwise specified.
  • the present invention also includes various isomers other than those described above within the scope of technical common sense in the technical field.
  • the chemical structure may be different from that of the formula (I).
  • the scope of the present invention It is clear that it is within.
  • the triazolopyrimidine derivative of the formula (I) or a salt thereof can be produced according to the following production methods [1] to [19] and usual salt production methods. The reaction flow will be described in detail below for each production method. Manufacturing method [1]
  • R 1a is a hydrogen atom, alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen
  • R 6 and R 7 are each independently alkyl; A, X, Z and m are as defined above.
  • the production method [1] comprises the reaction steps of the above [1] -1 and [1] -2. From the compound of the formula (II), [1,2,4] triazolo [1,5 of the formula (I-1) -A] Pyrimidine derivatives can be produced. Each reaction step will be described in detail below.
  • an ⁇ , ⁇ -unsaturated ketone derivative of the formula (IV) can be produced by condensing the compound of the formula (II) and the compound of the formula (III).
  • the compound of formula (III) can be used at a ratio of 1 to 5 equivalents, preferably 1 to 3 equivalents, per 1 mol of the compound of formula (II).
  • This reaction can be performed in the presence of a solvent, if necessary.
  • the solvent is not particularly limited as long as it does not adversely influence the reaction.
  • alcohols such as methanol, ethanol, propanol and butanol
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • pentane and hexane Aliphatic hydrocarbons such as petroleum ether, heptane, petroleum ether, ligroin, petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran, dioxane; esters such as methyl acetate and ethyl acetate; acetonitrile Nitriles such as propionitrile; acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidinone; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; Heki Phosphoric acid amides such as methyl phosphoramide; chloroform, dich
  • the compound of formula (I-1) can be produced by condensing the compound of formula (IV) and the compound of formula (V).
  • the compound of the formula (V) can be used in a ratio of 1 to 10 equivalents, desirably 1 to 2.5 equivalents, per 1 mol of the compound of the formula (IV).
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as it does not adversely affect the reaction.
  • carboxylic acids such as acetic acid and propionic acid
  • alcohols such as methanol, ethanol, propanol and butanol
  • benzene, toluene and xylene for example, carboxylic acids such as acetic acid and propionic acid; alcohols such as methanol, ethanol, propanol and butanol; benzene, toluene and xylene.
  • Aromatic hydrocarbons such as pentane, hexane, heptane, petroleum ether, ligroin, petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran, dioxane; methyl acetate Esters such as ethyl acetate; nitriles such as acetonitrile and propionitrile; acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidinone; and dimethyl sulfoxide Sulfoxy Sulfones such as sulfolane; phosphoric acid amides such as hexamethylphosphoramide; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; and mixed solvents thereof Among them, carboxylic
  • R 1b is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, and halogen substituted.
  • R 8 is alkyl;
  • A, X, Z and m are as described above.
  • the production method [2] comprises the reaction steps of the above [2] -1 and [2] -2. From the compound of formula (II), [1,2,4] triazolo [1,5 of formula (I-2) -A] Pyrimidine derivatives can be produced. Each reaction step will be described in detail below.
  • the compound of formula (VII) can be produced by reacting the compound of formula (II) with the compound of formula (VI).
  • the compound of the formula (VI) can be used in an amount of 1 equivalent to a large excess, desirably 1 to 3 equivalents, relative to 1 mol of the compound of the formula (II). This reaction can usually be performed in the presence of a base and a solvent.
  • the base examples include metal hydrides such as sodium hydride and potassium hydride; metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metals such as sodium and potassium; sodium methoxide and sodium ethoxide And alkali metal alkoxides such as potassium tertiary butoxide;
  • the base can be used in an amount of 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to 1 mol of the compound of formula (II).
  • the solvent is not particularly limited as long as it does not adversely influence the reaction.
  • aromatic hydrocarbons such as benzene, toluene, xylene; pentane, hexane, heptane, petroleum ether, ligroin, petroleum benzine Aliphatic hydrocarbons; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran, dioxane; acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidinone; Examples thereof include sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane; and mixed solvents thereof. Ethers are desirable.
  • the reaction temperature is usually 0 to 70 ° C., preferably 10 to 50 ° C.
  • the reaction time is usually
  • the compound of formula (I-2) can be produced by condensing the compound of formula (VII) with the compound of formula (V).
  • the compound of the formula (V) can be used at a ratio of 1 to 10 equivalents, preferably 1 to 3 equivalents, relative to 1 mol of the compound of the formula (VII).
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as it does not adversely influence the reaction.
  • carboxylic acids such as acetic acid and propionic acid
  • alcohols such as methanol, ethanol, propanol and butanol
  • aromatic carbonization such as benzene, toluene and xylene Hydrogen: aliphatic hydrocarbons such as pentane, hexane, heptane, petroleum ether, ligroin, petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran, dioxane; esters such as methyl acetate and ethyl acetate Nitriles such as acetonitrile and propionitrile; acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidinone; sulfoxides such as dimethyl sulfoxide; sulfolane and the like Examples include sulfones; phosphoric acid amide
  • R 9 is alkyl; R 1b , X, Z and m are as described above.
  • the production method [3] comprises the reaction steps of the above [3] -1 and [3] -2. From the compound of the formula (VIII), [1,2,4] triazolo [1,5] of the formula (I-2) -A] Pyrimidine derivatives can be produced. Each reaction step will be described in detail below.
  • the compound of formula (VII) can be produced by reacting the compound of formula (VIII) with the compound of formula (IX).
  • the compound of the formula (IX) can be used in a proportion of 0.8 equivalent to a large excess, desirably 1 to 10 equivalent, relative to 1 mol of the compound of the formula (VIII).
  • This reaction can usually be performed in the presence of a base and a solvent.
  • the base include those similar to the reaction step [2] -1 in the above production method [2].
  • the base can be used in a proportion of usually 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to 1 mol of the compound of the formula (VIII).
  • the solvent is not particularly limited as long as it does not adversely influence the reaction.
  • the same solvents as those in the reaction step [2] -1 of the above production method [2] can be exemplified, and among these, ethers are desirable.
  • the reaction temperature is usually 0 to 70 ° C., preferably 10 to 50 ° C.
  • the reaction time is usually 0.1 to 24 hours.
  • This reaction step can be carried out in the same manner as in the reaction step [2] -2 of the production method [2]. Manufacturing method [4]
  • R 1c is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, cyano or halogen.
  • R 10 is alkyl;
  • R 11 is OH, alkyl, cycloalkyl P is 2 when R 11 is alkyl, cycloalkyl or alkoxy, and 3 when R 11 is a fluorine atom;
  • alkyl or alkoxy of R 11 is an adjacent boron atom May be bonded to each other to form a ring;
  • hal is a halogen;
  • R 2 , R 3 , R 4 , R 5 , A, X, Z and m are as described above. Examples of the halogen represented by hal include fluorine, chlorine, bromine or iodine atoms.
  • Production method [4] comprises the reaction steps of [4] -1, [4] -2, [4] -3 and [4] -4, and from the compound of formula (X) to formula (I-4) [1,2,4] Triazolo [1,5-a] pyrimidine derivatives can be produced. Each reaction step will be described in detail below.
  • This reaction step is a reaction step for halogenating the compound of the formula (XI), (A) reacting a compound of formula (XI) with a chlorinating agent or brominating agent to produce a compound of formula (XII) wherein hal is a chlorine or bromine atom; (B) If necessary, the compound of the formula (XII) formed in (a) and a fluorinating agent are reacted to give a compound of the formula (XII) (wherein hal is a fluorine atom) Manufacturing; and (C) If necessary, the compound of formula (XII) formed in (a) is reacted with ammonia and then reacted with an iodinating agent in the presence of a diazotizing agent to give a compound of formula (XII) ( Wherein at least one hal is an iodine atom).
  • the methods (a) to (c) will be described in detail below.
  • Examples of the chlorinating agent include phosphorus oxychloride, phosphorus trichloride, and phosphorus pentachloride.
  • Examples of the brominating agent include phosphorus oxybromide, phosphorus tribromide, and phosphorus pentabromide.
  • the chlorinating agent or brominating agent can be used usually in a proportion of 1 equivalent to a large excess with respect to 1 mol of the compound of the formula (XI). This reaction can be performed in the presence of a solvent, if necessary.
  • the solvent is not particularly limited as long as it does not adversely affect the reaction, and examples thereof include halogenated hydrocarbons such as dichloromethane.
  • the reaction temperature is usually 0 ° C. to the reflux temperature of the reaction mixture, preferably 20 ° C. to the reflux temperature of the reaction mixture.
  • the reaction time is usually 1 to 48 hours.
  • Examples of the fluorinating agent include fluorides of alkali metals, particularly potassium fluoride, antimony pentafluoride and diethylaminosulfur trifluoride.
  • the fluorinating agent can be used in an amount of 1 to 5 equivalents, preferably 1.5 to 3 equivalents, per mole of the compound of formula (XII) (wherein hal is a chlorine atom or a bromine atom).
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as it does not adversely influence the reaction.
  • aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile and propionitrile; sulfones such as sulfolane; And acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidinone; and mixed solvents thereof.
  • sulfones or acid amides are used as a solvent, it is advantageous to use toluene as a co-solvent to assist dehydration of the fluorinating agent.
  • the reaction temperature is usually 15 ° C. to the reflux temperature of the reaction mixture, preferably 40 ° C. to the reflux temperature of the reaction mixture.
  • the reaction time is usually 2 to 48 hours.
  • the reaction temperature is from 20 ° C. to the reflux temperature of the reaction mixture, preferably from 40 ° C. to the reflux temperature of the reaction mixture.
  • the reaction time is usually 2 to 48 hours.
  • the reaction is then carried out with an iodinating agent in the presence of a diazotizing agent.
  • a diazotizing agent include any alkyl ester of nitrous acid, and isopentyl nitrite is particularly preferable.
  • the diazotizing agent can be used usually in a ratio of 1 equivalent to 5 equivalents per 1 mol of the compound of the formula (XII) (wherein hal is a chlorine or bromine atom).
  • the iodinating agent include iodine and diiodomethane.
  • the iodinating agent can be used in an amount of 1 to 5 equivalents, preferably 1.5 to 3 equivalents, per mole of the compound of formula (XII) (wherein hal is a chlorine atom or a bromine atom).
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as it does not adversely influence the reaction.
  • aliphatic hydrocarbons such as pentane, hexane, heptane, petroleum ether, ligroin, petroleum benzine; diethyl ether, dipropyl ether, diethylene
  • ethers such as butyl ether, tetrahydrofuran and dioxane
  • esters such as methyl acetate and ethyl acetate
  • nitriles such as acetonitrile and propionitrile
  • the reaction of (c) can be carried out as a one-pot synthesis, and when an alkyl ester of nitrous acid is used as a diazotizing agent, diiodomethane can be used as a cosolvent as an iodinating agent. .
  • the reaction temperature is usually 60 ° C. to 120 ° C., desirably 70 ° C. to 110 ° C.
  • the reaction time is usually 1 to 48 hours.
  • R 11 is a fluorine atom
  • p is 3. Since the —BF 3 group is negatively charged, Forms trifluoroborate salts with alkali metals.
  • Examples of the substituted boron represented by B (R 11 ) p in formula (XIII) include hydroxyboron, alkylboron, alkoxyboron, and trifluoroborate potassium salt.
  • the boron compound of the formula (XIII) can be used at a ratio of 0.5 to 1 equivalent per 1 mol of the compound of the formula (XII).
  • the transition metal catalyst used in this reaction means a transition metal compound or a complex of a transition metal compound and an arbitrary ligand.
  • a transition metal compound or a complex of a transition metal compound and an arbitrary ligand for example, palladium-carbon (Pd / C), tetrakis (triphenylphosphine) palladium (0), bis (dibenzylideneacetone) palladium (0), tetrakis (dibenzylideneacetone) dipalladium (0), palladium (II)- Examples thereof include triphenylphosphine and palladium (II) acetate-tricyclohexylphosphine. .
  • transition metal catalyst can be used in a proportion of 0.001 to 0.2 equivalent, preferably 0.01 to 0.1 equivalent, relative to 1 mol of the compound of formula (XII).
  • This reaction can usually be performed in the presence of a base.
  • the base include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate; alkaline earth metal carbonates such as calcium carbonate; sodium hydroxide , Alkali metal hydroxides such as potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide; inorganic salts such as cesium fluoride and potassium fluoride, triethylamine, pyridine, 4- (N, N -Amines such as (dimethylamino) pyridine;
  • the base can be used usually in a proportion of 0.9 to 20 equivalents per 1 mol of the compound of the formula (XII).
  • this reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as it does not adversely influence the reaction.
  • water alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; pentane Aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin, petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether; acetonitrile, propionitrile Nitriles such as: halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; and mixed solvents thereof.
  • the reaction temperature is usually 15 ° C. to the reflux temperature of the reaction mixture, preferably 40 ° C. to the reflux temperature of the reaction mixture.
  • the reaction time is not constant depending on the reaction temperature, reaction amount, reaction pressure and the like, but is usually 1 to 96 hours.
  • the boron compound of formula (XIII) is commercially available or can be synthesized by a conventional method.
  • it can be synthesized from the corresponding halogen, preferably a bromine derivative, by the action of trimethyl borate in the presence of a base such as tert-butyllithium.
  • the compound of formula (I-4) can be produced by reacting the compound of formula (I-3) with a nucleophile.
  • nucleophile examples include amines represented by the general formula HNR 4 R 5 (wherein R 4 and R 5 are as described above); the general formula HOR 2 (wherein R 2 is the same as that described above).
  • alkali metal salts such as sodium cyanide and sodium azide; heterocyclic amines such as morpholine or alkali metal salts thereof; organometallic reagents such as methylmagnesium bromide, ethylmagnesium bromide and phenylmagnesium bromide; Can do. More specific examples include methylamine, dimethylamine, piperidine; sodium methoxide, sodium ethoxide; sodium mercaptan and the like.
  • the nucleophile can be used at a ratio of 1 to 30 equivalents per 1 mol of the compound of the formula (I-3).
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as it does not adversely influence the reaction.
  • alcohols such as methanol, ethanol and propanol
  • ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane and dimethoxyethane
  • Halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, trichloroethane and dichloroethylene
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • aliphatics such as pentane and hexane Hydrocarbons
  • Esters such as methyl acetate and ethyl acetate
  • Nitriles such as acetonitrile and propiononitrile
  • R 1d is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, and halogen substituted.
  • R 12 is alkyl; R 11 , A, X, Y, Z, hal, m and p are as described above.
  • Production method [5] comprises the reaction steps of [5] -1, [5] -2 and [5] -3 above, and the compound of formula (XIV) is converted to [1,2,4 of formula (I-5). ] A triazolo [1,5-a] pyrimidine derivative can be produced.
  • the compound of formula (XV) can be produced by condensing the compound of formula (XIV) with the compound of formula (V).
  • the compound of the formula (V) can be used in a proportion of usually 0.8 to 10 equivalents, desirably 0.8 to 3 equivalents, relative to 1 mol of the compound of the formula (XIV).
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as it does not adversely influence the reaction.
  • carboxylic acids such as acetic acid and propionic acid
  • alcohols such as methanol, ethanol, propanol, and butanol
  • methyl acetate, ethyl acetate and the like are examples of carboxylic acids such as acetic acid and propionic acid, alcohols such as methanol, ethanol, propanol, and butanol; methyl acetate, ethyl acetate and the like.
  • Nitriles such as acetonitrile and propionitrile; acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidinone; sulfoxides such as dimethyl sulfoxide; sulfolane Examples thereof include sulfones such as: phosphoric acid amides such as hexamethylphosphoramide; and mixed solvents thereof, among which carboxylic acids are preferable.
  • the reaction temperature is usually 50 to 150 ° C., desirably 80 to 120 ° C.
  • the reaction time is usually 0.5 to 100 hours.
  • R 3 , X, Z, hal and m are as described above.
  • the production method [6] comprises the reaction steps of the above [6] -1 and [6] -2. From the compound of formula (II), [1,2,4] triazolo [1,5 of formula (I-6) -A] Pyrimidine derivatives can be produced. Each reaction step will be described in detail below.
  • an ⁇ , ⁇ -unsaturated ketone derivative of formula (XVIII) can be produced by reacting a compound of formula (II) with carbon disulfide and a compound of formula (XVII).
  • Carbon disulfide and the compound of formula (XVII) can be used in an amount of 1 to 5 equivalents, preferably 1 to 3 equivalents, per 1 mol of the compound of formula (II).
  • This reaction can usually be performed in the presence of a base and a solvent.
  • the base include metal hydrides such as sodium hydride and potassium hydride; metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metals such as sodium and potassium; sodium methoxide and sodium ethoxide. And alkali metal alkoxides such as potassium tertiary butoxide; and the like.
  • the base can be used in an amount of 1 to 10 equivalents, preferably 1 to 3 equivalents, relative to 1 mol of the compound of formula (II).
  • the solvent is not particularly limited as long as it does not adversely influence the reaction.
  • the same solvents as those in the reaction step [1] -1 of the above production method [1] can be exemplified, and among these, ethers are desirable.
  • the reaction temperature is usually 0 to 100 ° C., preferably 10 to 50 ° C.
  • the reaction time is usually 6 to 48 hours.
  • [6] -2 In this reaction step, the compound of the formula (I-6) can be produced by condensing the compound of the formula (XVIII) and the compound of the formula (V).
  • the compound of the formula (V) can be used in an amount of 1 to 5 equivalents, preferably 1 to 3 equivalents, relative to 1 mol of the compound of the formula (XVIII).
  • This reaction can usually be performed in the presence of a base and a solvent.
  • the base include metal hydrides such as sodium hydride and potassium hydride; metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metals such as sodium and potassium; sodium methoxide and sodium ethoxide Alkali metal alkoxides such as potassium tertiary butoxide; carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; organic bases such as triethylamine and pyridine; Can do.
  • the base can be used in a proportion of 1 to 5 equivalents, preferably 1 to 3 equivalents, relative to 1 mol of the compound of formula (V).
  • the solvent is not particularly limited as long as it does not adversely influence the reaction, and examples thereof include the same as those in the reaction step [1] -1 of the above production method [1]. desirable.
  • the reaction temperature is usually 100 to 200 ° C.
  • the reaction time is usually 0.1 to 10 hours. Manufacturing method [7]
  • R 3 , X, Z, m and n are as described above.
  • a [1,2,4] triazolo [1,5-a] pyrimidine derivative of the formula (I-7) is produced by reacting the compound of the formula (I-6) with an oxidizing agent. it can.
  • oxidizing agent used in this reaction examples include hydrogen peroxide, peracetic acid, m-chloroperbenzoic acid, and the like.
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as it does not adversely affect the reaction.
  • halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride and 1,2-dichloroethane, and ketones such as acetone and methyl ethyl ketone.
  • ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane; carboxylic acids such as acetic acid and propionic acid; and mixed solvents thereof.
  • the reaction temperature is usually 15 ° C. to reflux temperature.
  • the reaction time is usually 1 to 24 hours.
  • R 1e is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen, cyano, Aryl optionally substituted with halogen, heterocyclic group optionally substituted with alkyl, OR 2 , NR 4 R 5 or N 3 ; R 2 , R 4 , R 5 , A, X, Z and m are As described above.
  • a [1,2,4] triazolo [1,5-a] pyrimidine derivative of the formula (I-8) is reacted by reacting a compound of the formula (I-7) with a nucleophile.
  • a nucleophile include amines represented by the general formula HNR 4 R 5 (wherein R 4 and R 5 are as described above); the general formula HOR 2 (wherein R 2 is the same as that described above).
  • Alkali metal salts (metal alkoxides) of alcohols represented by the following formulas; various alkali metal salts such as sodium cyanide and sodium azide; heterocyclic amines such as morpholine or alkali metal salts thereof; And organic metal reagents such as ethylmagnesium bromide and phenylmagnesium bromide; fluorinating agents such as potassium fluoride, cesium fluoride and tetraammonium fluoride; More specific examples include methylamine, dimethylamine, piperidine; sodium methoxide, sodium ethoxide; and the like.
  • the nucleophilic agent can be used in an amount of 1 to 10 equivalents, preferably 1.5 to 3 equivalents, relative to 1 mol of the compound of formula (I-7).
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as it does not adversely influence the reaction.
  • alcohols such as methanol, ethanol, propanol and butanol
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • pentane and hexane Aliphatic hydrocarbons such as benzene, heptane, petroleum ether, ligroin, petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran, dioxane; chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride
  • Halogenated hydrocarbons such as chloroethane, dichloroethane, trichloroethane, dichloroethylene
  • esters such as methyl acetate and ethyl acetate
  • R 13 is alkyl; R 9 , X, Z, hal and m are as described above.
  • the production method [9] comprises the reaction steps of the above [9] -1 to [9] -5, and from the compound of the formula (VIII), the compound of the formula (I-9) or the formula (I-3) [1, 2, 4] A triazolo [1,5-a] pyrimidine derivative can be produced. Each reaction step will be described in detail below.
  • the compound of formula (XX) can be produced by reacting the compound of formula (VIII) with the compound of formula (XIX) in the presence of a base.
  • the compound of the formula (XIX) can be used in a proportion of 0.8 equivalent to large excess, desirably 1 to 30 equivalents, relative to 1 mol of the compound of the formula (VIII).
  • Examples of the base include those similar to the reaction in the reaction step [6] -1 of the production method [6].
  • the base can be used at a ratio of 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to 1 mol of the compound of the formula (VIII). This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as it does not adversely influence the reaction, and examples thereof include the same reaction as in the reaction step [2] -1 in the above production method [2]. desirable.
  • the reaction temperature is usually 0 to 70 ° C., preferably 10 to 50 ° C.
  • the reaction time is usually 0.1 to 24 hours.
  • the compound of the formula (XXI) can be produced by hydrolyzing the compound of the formula (XX) in the presence of a base and water.
  • the base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
  • the base can be used in an amount of 1 equivalent to large excess, desirably 2 to 10 equivalents, relative to 1 mol of the compound of formula (XX).
  • the reaction temperature is usually 0 to 70 ° C., preferably 10 to 50 ° C.
  • the reaction time is usually 0.1 to 24 hours.
  • the compound of the formula (XXII) can be produced by reacting the compound of the formula (XXI) with a halogenating agent.
  • a halogenating agent include thionyl chloride and oxalyl dichloride.
  • the halogenating agent can be used in a proportion of 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to 1 mol of the compound of formula (XXI). This reaction can be performed in the presence of a solvent, if necessary.
  • the solvent is not particularly limited as long as it does not adversely influence the reaction, and examples thereof include halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane.
  • the reaction temperature is usually 0 to 100 ° C., preferably 10 to 50 ° C.
  • the reaction time is usually 0.1 to 24 hours.
  • the same solvent as in the reaction step [2] -1 in the above production method [2] can be mentioned, and among them, acid amides are preferable.
  • the reaction temperature is usually 0 to 150 ° C., preferably 20 to 100 ° C.
  • the reaction time is usually 0.5 to 100 hours.
  • the compound of compound (I-9) is reacted with a halogenating agent to react with 5-halo [1,2,4] triazolo [1, 5-a] pyrimidine derivatives can be produced.
  • a halogenating agent include thionyl chloride, phosphorus oxychloride, phosphorus oxybromide and the like.
  • the halogenating agent can be used in a proportion of 1 to 20 equivalents, preferably 1 to 8 equivalents, relative to 1 mol of the compound of formula (I-9). This reaction can be performed in the presence of a solvent, if necessary.
  • the solvent is not particularly limited as long as it does not adversely influence the reaction, and examples thereof include halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane.
  • the reaction temperature is usually 0 to 150 ° C., preferably 20 to 100 ° C.
  • the reaction time is usually 0.1 to 24 hours. Manufacturing method [10]
  • Production method [10] is a production example of a [1,2,4] triazolo [1,5-a] pyrimidine derivative of the formula (I-12), for example, the above [10] -1 to [10] -3
  • the compound of the formula (I-12) can be produced by any reaction. Each reaction is described in detail below.
  • the compound of the formula (I-12) can be produced by reacting the compound of the formula (I-10) with an oxidizing agent.
  • the oxidizing agent include sodium periodate, selenium dioxide, potassium permanganate and the like.
  • the oxidizing agent can be used in a proportion of 0.8 equivalent to large excess, preferably 1 to 30 equivalents, relative to 1 mol of the compound of formula (I-10).
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as it does not adversely influence the reaction. Examples thereof include water; amides such as N, N-dimethylformamide; and the like.
  • the reaction temperature is 0 to 200 ° C., desirably 0 to 150 ° C.
  • the reaction time is 1 to 30 hours.
  • [10] -2 This reaction includes the above two reactions of (1) metalation and (2) formylation. That is, the compound of the formula (I-12) can be produced by metallizing the compound of the formula (I-3), reacting it with a formylating agent and then hydrolyzing it.
  • the reactions (1) and (2) can usually be carried out continuously.
  • the metalation in (1) means preparation of a lithium reagent by a halogen-lithium exchange reaction with a lithium reagent such as n-butyllithium or tert-butyllithium, or a Grignard reagent by a halogen-magnesium exchange reaction with a Grignard reagent.
  • the preparation of a Grignard reagent by reaction with metallic magnesium and the lithium reagent, Grignard reagent and magnesium used in this case are metallizing agents.
  • the metallizing agent can be used in a proportion of 1 equivalent to 1.5 equivalents relative to the compound of formula (I-3).
  • the reaction temperature is usually ⁇ 100 to 70 ° C., desirably ⁇ 30 to 50 ° C.
  • the reaction time is usually 0.1 to 24 hours.
  • Examples of the formylating agent in (2) include methyl formate, N, N-dimethylformamide, 4-formylmorpholine and the like.
  • the formylating agent can be used at a ratio of 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to 1 mol of the compound of formula (I-3).
  • the reaction temperature is usually ⁇ 20 to 50 ° C., desirably ⁇ 10 to 30 ° C.
  • the reaction time is usually 0.1 to 24 hours.
  • the compound of formula (I-12) can be produced by hydrolyzing the reaction product in the presence of an acid and water.
  • the acid include inorganic acids such as hydrochloric acid and sulfuric acid.
  • the acid can be used in an amount of 1 equivalent to a large excess, desirably 2 to 10 equivalents, relative to the metallizing agent.
  • the reaction temperature is usually ⁇ 10 to 30 ° C., preferably 0 to 20 ° C.
  • the reaction time is usually 0.1 to 24 hours.
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as it does not adversely affect the reaction.
  • the same solvent as in reaction step [2] -1 of the above production method [2] can be mentioned, and among these, ethers are desirable.
  • the compound of the formula (I-12) can be produced by reacting the compound of the formula (I-11) with a reducing agent.
  • a reducing agent examples include diisobutylaluminum hydride (DIBAL), sodium bis (2-methoxyethoxy) aluminum hydride (SBMEA), and the like.
  • DIBAL diisobutylaluminum hydride
  • SBMEA sodium bis (2-methoxyethoxy) aluminum hydride
  • the reducing agent can be used in a proportion of 1 to 2 equivalents, preferably 1 to 1.5 equivalents, relative to 1 mol of the compound of formula (I-11). This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as it does not adversely affect the reaction, and examples thereof include ethers such as tetrahydrofuran, aromatic hydrocarbons such as benzene and toluene.
  • the reaction temperature is usually ⁇ 80 ° C. to 100 ° C., desirably ⁇ 30 to 50 ° C.
  • the reaction time is usually 0.1 to 24 hours. Manufacturing method [11]
  • R 14 represents alkyl or cycloalkyl, and X, Z and m are as described above.
  • the compound of the formula (I-11) is reacted with a nucleophile and then hydrolyzed to thereby react the [1,2,4] triazolo [1,5- (5) of the formula (I-13).
  • a] Pyrimidine derivatives can be produced.
  • the nucleophilic agent include Grignard reagents such as methylmagnesium bromide and cyclopropylmagnesium chloride.
  • the nucleophilic agent can be used in an amount of 1 to 2 equivalents, preferably 1 to 1.3 equivalents, relative to 1 mol of the compound of the formula (I-11). This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as it does not adversely influence the reaction, and examples thereof include ethers such as tetrahydrofuran; aliphatic hydrocarbons such as pentane hexane; and the like.
  • the reaction temperature is usually ⁇ 80 ° C. to 100 ° C., desirably ⁇ 30 to 50 ° C.
  • the reaction time is usually 0.1 to 24 hours.
  • the compound of formula (I-13) can be obtained by hydrolyzing the reaction product in the presence of an acid and water.
  • the acid include inorganic acids such as hydrochloric acid and sulfuric acid.
  • the acid can be used in an amount of 1 equivalent to a large excess relative to the nucleophile, preferably 2 to 10 equivalents.
  • the reaction temperature is usually ⁇ 20 to 30 ° C., preferably 0 to 20 ° C.
  • the reaction time is usually 0.1 to 24 hours.
  • R 1f is an alkyl which may be substituted with A or a heterocyclic group which may be substituted with alkyl; R 14 , X, Z and m are as described above. Examples of R 1f include dimethoxymethyl, diethoxymethyl, 1,3-dioxolan-2-yl and the like.
  • Examples of the alcohol include methanol, ethanol, and ethylene glycol.
  • the alcohol can be used in a proportion of 1 equivalent to a large excess with respect to 1 mol of the compound of the formula (I-12) or the formula (I-13).
  • This reaction can be performed in the presence of an acid catalyst, if necessary.
  • the acid catalyst include inorganic acids such as concentrated hydrochloric acid and concentrated sulfuric acid; organic acids such as acetic acid and p-toluenesulfonic acid.
  • the acid catalyst can be used in a proportion of 0.001 to 0.3 equivalent, desirably 0.01 to 0.2 equivalent, relative to 1 mol of the compound of formula (I-12) or formula (I-13).
  • This reaction can be performed in the presence of a solvent, if necessary.
  • the solvent is not particularly limited as long as it does not adversely influence the reaction, and examples thereof include aromatic hydrocarbons such as benzene and toluene.
  • the reaction temperature is usually 0 ° C. to 200 ° C., preferably 10 to 100 ° C.
  • the reaction time is usually 0.1 to 24 hours. Manufacturing method [13]
  • Production method [13] is an example of production of a [1,2,4] triazolo [1,5-a] pyrimidine derivative of formula (I-15).
  • the production methods [13] -1 to [13] -3 The compound of the formula (I-15) can be produced by any reaction. Each reaction is described in detail below.
  • the compound of formula (I-15) can be produced by hydrolyzing the compound of formula (I-11).
  • This reaction can be carried out according to a conventional method. For example, it can be carried out according to the method described in Org. Synth., III, 557 (1955).
  • As a kind of hydrolysis any of acid hydrolysis, alkali hydrolysis, and oxidative hydrolysis may be used.
  • the compound of formula (I-15) can be produced by oxidizing the compound of formula (I-12) with an oxidizing agent.
  • the oxidizing agent include manganese dioxide, potassium permanganate, sodium periodate, Jones reagent, pyridium dichromate, and the like.
  • the oxidizing agent can be used in an amount of 1 to 3 equivalents, preferably 1 to 2 equivalents, relative to 1 mol of the compound of the formula (I-12).
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as it does not adversely affect the reaction, and examples thereof include water, acetone, acetonitrile, methanol and the like.
  • the reaction temperature is usually 0 to 50 ° C.
  • the reaction time is usually 0 to 24 hours. Manufacturing method [14]
  • R 15 is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, cyano or halogen.
  • the production method [14] comprises the reaction steps of the above [14] -1 and [14] -2. From the compound of the formula (I-15), the [1,2,4] triazolo [1] of the formula (I-17) , 5-a] pyrimidine derivatives can be prepared. Each reaction step will be described in detail below.
  • the compound of the formula (I-16) can be produced by reacting the formula (I-15) with a halogenating agent.
  • a halogenating agent examples include thionyl chloride and oxalyl chloride.
  • the halogenating agent can be used in an amount of usually 1 equivalent to a large excess, desirably 1 to 5 equivalents, relative to 1 mol of the compound of the formula (I-15).
  • This reaction can be performed in the presence of a solvent, if necessary.
  • the solvent is not particularly limited as long as it does not adversely influence the reaction.
  • the same solvent as in reaction step [9] -3 of the above production method [9] can be mentioned.
  • the reaction temperature is usually 0 to 100 ° C., preferably 0 to 50 ° C.
  • the reaction time is usually 1 to 24 hours.
  • the compound of formula (I-17) can be produced by reacting the compound of formula (I-16) with a nucleophile. This reaction can be carried out according to the reaction step [4] -4 in the above production method [4]. Manufacturing method [15]
  • Production method [15] is a production example of a [1,2,4] triazolo [1,5-a] pyrimidine derivative of formula (I-19), for example, in the above [15] -1 or [15] -2
  • the compound of formula (I-19) can be produced by any method. Each reaction is described in detail below.
  • the compound of formula (I-19) can be produced by the rearrangement reaction of the compound of formula (I-15).
  • the compound of formula (I-15) and diphenyl phosphate azide are reacted by heating under reflux in the presence of triethylamine in a mixed solution of tert-butanol and toluene to obtain a tert-butyl carbamate derivative.
  • the compound of formula (I-19) can be produced by heating with a carbamate derivative and trifluoroacetic acid.
  • the compound of formula (I-19) can be produced by reacting the compound of formula (I-18) with a reducing agent.
  • the reducing agent include sodium borohydride.
  • the reducing agent can be used at a ratio of 1 to 2 equivalents relative to 1 mole of the formula (I-18).
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as it does not adversely affect the reaction, and examples thereof include alcohols; ethers.
  • the reaction temperature is usually 0 to 50 ° C.
  • the reaction time is usually 1 to 24 hours. Manufacturing method [16]
  • Q is a leaving group such as halogen, alkylcarbonyloxy, haloalkylcarbonyloxy, triflate or mesylate; R 4 , R 5 , X, Z and m are as described above.
  • the compound of the formula (XXIII) can be used usually in a proportion of 1 equivalent to a large excess, desirably 1 to 20 equivalents, relative to 1 mol of the compound of the formula (I-20).
  • This reaction can be performed in the presence of a base, if necessary.
  • the base include amines such as triethylamine and pyridine; inorganic bases such as potassium carbonate and sodium carbonate;
  • the base can be generally used in a proportion of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 mol of the compound of formula (I-20).
  • This reaction can be performed in the presence of a solvent, if necessary.
  • the solvent is not particularly limited as long as it does not adversely influence the reaction, and examples thereof include acetones; ethers; nitriles;
  • the reaction temperature is 0 to 50 ° C., desirably 0 to 30 ° C.
  • the reaction time is usually 1 to 24 hours. In this reaction, the reaction rate may be accelerated by using a catalytic amount of dimethylaminopyridine.
  • R 16 is OR 2 or NR 4 R 5 ;
  • R 2 , R 4 , R 5 , X, Z and m are as described above.
  • the compound of the formula (XXIV) can be used in an amount of 1 equivalent to a large excess, desirably 1 to 20 equivalents, relative to 1 mole of the compound of the formula (I-12).
  • This reaction can be performed in the presence of an acid catalyst, if necessary.
  • the acid catalyst include those similar to the above production method [12].
  • the acid catalyst can be used in a proportion of 0.001 to 0.3 equivalent, preferably 0.01 to 0.2 equivalent, relative to 1 mol of the compound of formula (I-12).
  • This reaction can be performed in the presence of a solvent, if necessary.
  • the solvent is not particularly limited as long as it does not adversely influence the reaction, and examples thereof include the same as in the above production method [12].
  • the reaction temperature is usually 0 to 150 ° C., preferably 10 to 100 ° C.
  • the reaction time is usually 0.1 to 24 hours. Manufacturing method [18]
  • R 16 , X, Z and m are as described above.
  • the compound of the formula (I-23) can be produced by reacting the compound of the formula (I-15) with the compound of the formula (XXV) in the presence of a catalyst or a condensing agent.
  • Examples of the compound of the formula (XXV) include alcohols such as methanol and ethanol; amines such as methylamine and dimethylamine; The compound of the formula (XXV) can be used usually in a proportion of 1 to 30 equivalents relative to 1 mol of the compound of the formula (I-15).
  • examples of the catalyst include inorganic acids and organic acids.
  • This reaction can be performed in the presence of a solvent, if necessary.
  • the solvent include alcohols; aromatic hydrocarbons; halogenated hydrocarbons;
  • the reaction temperature is usually 10 to 150 ° C., preferably 20 to 100 ° C.
  • the reaction time is usually 1 to 24 hours.
  • the condensing agent examples include dicyclohexylcarbodiimide, 1,1-carbonyldiimidazole, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide.
  • the condensing agent can be used in a proportion of usually 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to 1 mol of the formula (I-15).
  • This reaction can be performed in the presence of a solvent, if necessary.
  • the solvent include alcohols; aromatic hydrocarbons; halogenated hydrocarbons;
  • the reaction temperature is usually 0 to 100 ° C., preferably 0 to 50 ° C.
  • the reaction time is usually 1 to 24 hours. Manufacturing method [19]
  • R 17 is a hydrogen atom, OR 2 or NR 4 R 5 ; R 2 , R 4 , R 5 , X, Z, hal and m are as described above.
  • a compound of the formula (I-3) is reacted with a compound of the formula (XXVI) and carbon monoxide in the presence of a transition metal catalyst, a phosphine ligand and a base, thereby producing a compound of the formula (I -24) [1,2,4] triazolo [1,5-a] pyrimidine derivatives can be produced.
  • Examples of the compound of the formula (XXVI) include water; hydrogen; alcohols such as methanol and ethanol; amines such as methylamine and dimethylamine; The compound of the formula (XXVI) can be generally used at a ratio of 1 to 5 equivalents per 1 mol of the compound of the formula (I-3).
  • Carbon monoxide can be used in an amount of usually 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 mol of the compound of formula (I-3).
  • the transition metal catalyst include a palladium or cobalt catalyst.
  • the phosphine ligand can be selected according to the reaction system such as the type of transition metal catalyst. Examples of the combination of the transition catalyst and the ligand include palladium acetate and diphenylphosphinopropane.
  • the base examples include inorganic salts such as sodium carbonate and cesium carbonate; trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6-dimethylpyridine, 4-pyrrolidinopyridine, N -Methylmorpholine, N, N-dimethylaniline, N, N-diethylaniline, N-ethyl-N-methylaniline, 1,8-diazabicyclo [5.4.0] -7-undecene, 1,4-diazabicyclo [ 2.2.2] amines such as octane;
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as it does not adversely influence the reaction, and examples thereof include polar aprotic solvents such as N, N-dimethylformamide, dimethyl sulfoxide and N-methylpyrrolidone.
  • the reaction temperature is usually 25 to 120 ° C., preferably 50 to 70 ° C.
  • the reaction time is usually about 1 to 24 hours, preferably 3 to 7 hours. If necessary, the reaction can be carried out under pressure.
  • production method [1], production method [3], production method [4], production method [5], production method [9], production method [10], production method [12], production method [15] or production method [ 16] is a particularly desirable embodiment.
  • the pest control agent of the present invention includes, for example, various pest control agents that are problematic in the field of agriculture and horticulture, that is, agricultural and horticultural pest control agents, and pest control agents that parasitize animals, that is, animal parasite control agents. As particularly useful.
  • the pest control agent of the present invention is particularly useful for controlling pests among various pests, and the pest control agent is one of desirable embodiments.
  • Pesticides for agricultural and horticultural use are useful, for example, as insecticides, acaricides, nematicides or soil insecticides.
  • Plant parasitic mites such as rustic mites, mites, aphids such as peach aphids and cotton aphids; diamondback moths, weevil, scallops, codling moths, ball worms, tobacco worms, mai moths, yellow moths, prickly winged clams, Colorado Agricultural pests such as leaf beetle, cucumber beetle, ball weevil, planthoppers, leafhoppers, scale insects, stink bugs, whitefly, thrips, grasshoppers, fly flies, scarab beetles, Tamanayaga, Kaburayaga, ants, etc .; Parasitic nematodes such as mosquitoes, cyst nematodes, nesting nematodes, rice scented nematodes, strawberry nema
  • the agricultural and horticultural pest control agent of the present invention is particularly effective for controlling plant parasitic mites, agricultural pests, plant parasitic nematodes and the like. Among them, it is most useful as an insecticidal or acaricidal agent because it exhibits a further excellent effect in controlling plant parasitic mites and agricultural pests.
  • the agricultural and horticultural pest control agent of the present invention is also effective in controlling various resistant pests against drugs such as organic phosphorus agents, carbamate agents, and synthetic pyrethroid agents.
  • the compound of the formula (I) has an excellent osmotic transfer property
  • soil harmful insects, mites, nematodes It is possible to control pests in the foliage at the same time as the control of mosses, gastropods, and isopods.
  • pest control agent of the present invention there are agricultural and horticultural harmful substances that comprehensively control the above-mentioned plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods, soil pests, etc. Biological control agents are mentioned.
  • the agricultural and horticultural pest control agent of the present invention is usually a powder, granule, granule wettable powder, wettable powder, aqueous suspension, oily suspension by mixing the compound and various agricultural adjuvants.
  • a powder, granule, granule wettable powder, wettable powder, aqueous suspension, oily suspension by mixing the compound and various agricultural adjuvants.
  • Used in various forms, such as an agent, an aqueous solvent, an emulsion, a liquid, a paste, an aerosol, and a microdispersion but is generally used in the art as long as it meets the purpose of the present invention. Any formulation can be used.
  • Adjuvants used in the formulation include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch; water , Toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, alcohol, etc.
  • solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite,
  • Solvent fatty acid salt, benzoate, alkylsulfosuccinate, dialkylsulfosuccinate, polycarboxylate, alkylsulfate, alkylsulfate, alkylarylsulfate, alkyldiglycolethersulfate, al Sulfuric acid ester salt, alkyl sulfonate, alkyl aryl sulfonate, aryl sulfonate, lignin sulfonate, alkyl diphenyl ether disulfonate, polystyrene sulfonate, alkyl phosphate ester salt, alkyl aryl phosphate, Styryl aryl phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl
  • each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention.
  • it can be used by appropriately selecting from those known in the art.
  • a bulking agent for example, a bulking agent, a thickening agent, an anti-settling agent, an antifreezing agent, a dispersion stabilizer, a phytotoxicity reduction.
  • Various commonly used adjuvants such as agents, antifungal agents and the like can also be used.
  • the compounding ratio (weight ratio) of the compound of the formula (I) and various adjuvants is 0.001: 99.999 to 95: 5, preferably 0.005: 99.995 to 90:10. In actual use of these preparations, use them as they are, or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. Can be used.
  • the application of the agricultural and horticultural pest control agent of the present invention cannot be defined unconditionally due to differences in weather conditions, formulation form, application time, application location, type of pests and occurrence status, but generally 0.05 to 800,000 ppm, preferably 0.5
  • the active ingredient concentration is ⁇ 500,000 ppm
  • the application amount per unit area is 0.05 to 50,000 g, preferably 1 to 30,000 g, of the compound of formula (I) per hectare.
  • application of the agricultural and horticultural pest control agent which is another desirable embodiment of the pest control agent of the present invention, is performed according to the application of the pest control agent.
  • the present invention includes a method for controlling pests by such an application method, particularly a method for controlling plant parasitic mites, agricultural pests, and plant parasitic nematodes.
  • the various formulations of the pesticide for agricultural and horticultural use according to the present invention, or the dilutions thereof are usually applied by a commonly used application method, that is, spraying (for example, spraying, spraying, misting, atomizing, dusting, Water surface application, etc.), soil application (mixing, irrigation, etc.), surface application (application, powder coating, coating, etc.), immersion poison bait, etc.
  • spraying for example, spraying, spraying, misting, atomizing, dusting, Water surface application, etc.
  • soil application mixtureing, irrigation, etc.
  • surface application application, powder coating, coating, etc.
  • immersion poison bait etc.
  • the agricultural and horticultural pest control agent of the present invention can be used in combination or in combination with other agricultural chemicals, fertilizers, safeners, etc., and in this case, more excellent effects and activities may be exhibited.
  • Other agrochemicals include herbicides, insecticides, acaricides, nematicides, soil insecticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, plant growth regulators, etc. It is done.
  • a composition for controlling mixed pests in which a compound of formula (I) and one or more active ingredient compounds of other agricultural chemicals are mixed or used in combination is applicable range, timing of chemical treatment, control activity, etc. Can be improved in a preferred direction.
  • the compound of formula (I) and the active ingredient compound of other agricultural chemicals may be used by mixing separately formulated ones at the time of spraying, or by formulating both together.
  • the present invention includes such a composition for controlling mixed pests.
  • the mixing ratio (weight ratio) between the compound of formula (I) and the active ingredient compound of other pesticides cannot be specified unconditionally due to differences in weather conditions, formulation form, application time, application location, pest type or occurrence status. However, it is generally 1: 300 to 300: 1, preferably 1: 100 to 100: 1.
  • the appropriate amount to be applied is 0.1 to 50000 g, preferably 1 to 30000 g as the total amount of active ingredient compounds per hectare.
  • the present invention also includes a method for controlling pests by a method for applying such a composition for controlling mixed pests.
  • active ingredient compounds of insecticides, acaricides, nematicides or soil pesticides in the above other pesticides
  • active ingredient compounds include, for example, profenofos , Dichlorvos, fenamiphos, fenitrothion, EPN, diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, prothiofos, fothiaz , Cadusafos, dislufoton, isoxathion, isofenphos, ethion, etrimfos, quinalphos, dimethylvinphos, dimethoate, sulfophos ( sulprofos), thiometon, bamidithione (vamidot) hion), pyraclofos, pyridaphenthion, pirimiphos-methyl, propaphos, phosalone, formothion, malathion
  • Organometallic compounds such as fenbutatin oxide and cyhexatin; Fenvalerate, permethrin, cypermethrin, deltamethrin, cyhalothrin, tefluthrin, etofenprox, flufenprox, cyfluthrin , Fenpropathrin, flucytrinate, fluvalinate, cycloprothrin, lambda-cyhalothrin, pyrethrin, esfenvalerate, Tetramethrin, resmethrin, protrifenbute, bifenthrin, zeta-cypermethrin, acrinathrin, alpha-cypermethri n), allethrin, gamma-cyhalothrin, theta-cypermethrin, tau-fluvalinate, tralomethrin, profluthrin
  • Pyridine compounds such as pyridalyl, flonicamid and the like; Tetronic acid compounds such as spirodiclofen; Strobilurin-based compounds such as fluacrypyrim; Pyridinamine compounds such as flufenerim; Dinitro compounds; organic sulfur compounds; urea compounds; triazine compounds; hydrazone compounds; and other compounds such as buprofezin, hexythiazox, amitraz, chlordimeform, silafluofen ), Triazamate, pymetrozine, pyrimidifen, chlorfenapyr, indoxacarb, acequinocyl, etoxazole, cyromazine, 1,3-dichloropropene (1,3-dichloropropene), diafenthiuron, benclothiaz, bifenazate, spiromesifen, spirotetramat, propargi Propargite, clofentezine, metaflum
  • Bacillus thuringienses aizawai, Bacillus thuringienses kurstaki, Bacillus thuringienses israelensis, Bacillus thuringienses japonensis, Bacillus thuringienses tenebrionis, crystalline protein toxins produced by Bacillus thuringienses, entomopathogenic fungi, nematode pathogenic fungi, etc.
  • Microbial pesticides such as: avermectin, emamectin-benzoate, milbemectin, milbemycin, spinosad, ivermectin, lepimectin, DE-175, abamectin and antibiotics such as abamectin and emamectin; semi-synthetic antibiotics; natural products such as azadirachtin and rotenone; repellents such as deet;
  • the bactericidal active ingredient compound includes, for example, mepanipyrim, pyrimethanil, cyprodinil ( cyprodinil) and anilinopyrimidine compounds such as ferimzone; Tria such as 5-chloro-6- (2,4,6-trifluorophenyl) -7- (4-methylpiperidin-1-yl) [1,2,4] triazolo [1,5-a] pyrimidine Zolopyrimidine compounds; Pyridinamine compounds such as fluazinam; Triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, microbutanil, cyproconazole cyproconazole), tebuconazole, hexaconazole, furconazole-cis, prochloraz
  • Quinoxaline compounds such as quinomethionate; Dithiocarbamate compounds such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb, thiram; Organochlorine compounds such as fthalide, chlorothalonil, quintozene; Imidazole compounds such as benomyl, thiophanate-methyl, carbendazim, thiabendazole, fuberiazole, cyazofamid; Cyanoacetamide compounds such as cymoxanil; Metalaxyl, metalaxyl-M, mefenoxam, oxadixyl, offurace, benalaxyl, benalaxyl-M, also known as kiralaxyl, chiax ), Phenylamide compounds such as furalaxyl, cyprofuram;
  • Sulfenic acid compounds such as dichlofluanid; Copper-based compounds such as cupric hydroxide and oxine copper; isoxazole-based compounds such as hymexazol; Fosetyl aluminum (fosetyl-Al), tolclofos-methyl, edifenphos, iprobenfos, S-benzyl O, O-diisopropyl phosphorothioate, O-ethyl S, S-diphenyl phosphorodithioate, aluminum Organophosphorus compounds such as ethyl hydrogen phosphonate; N-halogenothioalkyl compounds such as captan, captafol, folpet; Dicarboximide compounds such as procymidone, iprodione, vinclozolin;
  • Benzanilide compounds such as flutolanil, mepronil, zoxamid, tiadinil; Carboxin (carboxin), oxycarboxin, thifluzamide, penthiopyrad, boscalid, isothianil, bixafen, 3- (difluoromethyl) -1-methyl-N- [(1RS, 4SR, 9RS) -1,2,3,4-Tetrahydro-9-isopropyl-1,4-methanonaphthalen-5-yl] pyrazole-4-carboxamide and 3- (difluoromethyl) -1-methyl- Of a mixture of N-[(1RS, 4SR, 9SR) -1,2,3,4-tetrahydro-9-isopropyl-1,4-methanonaphthalen-5-yl] pyrazole-4-carboxamide (isopyrazam) Such anilide compounds; Piperazine compounds such as triforine; Pyridine compounds such as pyrif
  • Organotin compounds such as fentin hydroxide and fentin acetate; Urea-based compounds such as pencycuron; Synamic acid compounds such as dimethomorph and flumorph; Phenyl carbamate compounds such as dietofencarb; Cyanopyrrole compounds such as fludioxonil and fenpiclonil; Azoxystrobin, kresoxim-methyl, metominofen, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin Strobilurin compounds such as pyraclostrobin, fluoxastrobin, fluacrypyrim;
  • Oxazolidinone compounds such as famoxadone; Thiazole carboxamide compounds such as ethaboxam; Silylamide compounds such as silthiopham; Iprovalicarb, Benthiavalicarb-isopropyl, methyl [S- (R, S)]-[3- (N-isopropoxycarbonylvalinyl) -amino] -3- (4-chloro Aminoacid amide carbamate compounds such as -phenyl) propionate (valiphenal); Imidazolidine compounds such as fenamidone; Hydroxyanilide compounds such as fenhexamid; Benzenesulfonamide compounds such as flusulfamide; Oxime ether compounds such as cyflufenamid; Phenoxyamide compounds such as fenoxanil; Antibiotics such as validamycin, kasugamycin, polyoxins; Guanidine compounds such as iminoctadine and dodine
  • animal parasite control agents include ectoparasites that parasitize on the body surface of the host animal (back, armpit, lower abdomen, inner thigh, etc.) and the host animal body (stomach, intestinal tract, lung, heart, liver). , Vascular, subcutaneous, lymphoid tissue, etc.) are effective in controlling endoparasites, and in particular, are effective in controlling ectoparasites.
  • ectoparasites examples include animal parasitic mites and fleas. There are so many of these types that it is difficult to list them all.
  • the animal parasitic mites for example Boophilus microplus (Boophilus microplus), Rhipicephalus sanguineus (Rhipicephalus sanguineus), Haemaphysalis longicornis (Haemaphysalis longicornis), Haemaphysalis flava (Haemaphysalis flava), Adenophora chima tick (Haemaphysalis campanulata), Isukachimadani (Haemaphysalis concinna), Yamatochimadani (Haemaphysalis japonica), H.
  • kitaokai Haemaphysalis kitaokai
  • Iyasuchimadani Haemaphysalis ias
  • Ixodes ovatus Ixodes ovatus
  • I. nipponensis Ixodes nipponensis
  • Schulze ticks Ixodes persulcatus
  • Takasago testudinarium Amblyomma testudinarium
  • Ootogechimadani Haemaphysalis megaspinosa
  • tick such as Dermacentor reticulatus , Dermacentor taiwanesis ; duck ( Dermanyssus gallinae ); Shidani (Ornithonyssus sylviarum), Torisashidani, such as Southern tri sand mite (Ornithonyssus bursa); Nan iodine tsutsugamushi (Eutromb
  • chiggers such as Miyagawa Tama chiggers (Helenicula miyagawai); Inutsumedani (Cheyletiella yasguri), rabbit Tsumedani (Cheyletiella parasitivorax), Nekotsumedani (Cheyletiella blakei) Tsumedani, such as; rabbits 9,000 mite (Psoroptes cuniculi), Ushishokuhidani (Chorioptes bovis), dog ear mites (Otodectes cynotis), mange mites (Sar coptes scabiei ), mite mites like Notoedres
  • fleas examples include ectoparasite worms belonging to the order Flea ( Siphonaptera ), and more specifically fleas belonging to the family Flea family ( Pulicidae ), Nagano family ( Ceratephyllus ) and the like.
  • fleas belonging to the family flea family include, for example, dog fleas ( Ctenocephalides canis ), cat fleas ( Ctenocephalides felis ), human fleas ( Purex irritans ), elephant fleas ( Echidnophaga gallinacea ), keops mouse fleas ( Xenopsylla cheopis ) Leptopsylla segnis ), European mud minnow ( Nosopsyllus fasciatus ), and Yamato mud mink ( Monopsyllus anisus ).
  • the animal parasite control agent containing the compound of the formula (I) is effective for controlling fleas belonging to the family flea family, especially dog fleas, cat fleas and the like.
  • ectoparasites include, for example, lice such as bovine lice, foal lice, sheep lice, bovine white lice, head lice; lice such as dog lice; blood-sucking dipterous pests such as bovine abs, quail sharks, .
  • endoparasites include nematodes such as lungworms, benthic worms, tuberous worms, gastric parasites, roundworms, and filamentous worms; Tapeworms such as real tapeworms, multi-headed tapeworms, single-banded tapeworms, multi-banded tapeworms; Japanese schistosomiasis, fluke like liver fluke; coccidium, malaria parasite, intestinal granulocyst, toxoplasma, chestnut Protozoa such as Ptosporidium, and the like.
  • nematodes such as lungworms, benthic worms, tuberous worms, gastric parasites, roundworms, and filamentous worms
  • Tapeworms such as real tapeworms, multi-headed tapeworms, single-banded tapeworms, multi-banded tapeworms
  • Japanese schistosomiasis fluke like liver fluke
  • Examples of host animals include various pet animals, livestock, poultry, etc., and more specifically dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (eg, pigeons, parrots, (E.g., nine-bird, bird, parakeet, juvenile pine, canary, etc.), cattle, horses, pigs, sheep, ducks, chickens, etc.
  • the animal parasite control agent containing the compound of the formula (I) is effective for controlling pests parasitic on pet animals or livestock, particularly ectoparasites.
  • pet animals or domestic animals it is particularly effective for dogs, cats, cows or horses.
  • the compound of the formula (I) when used as an animal parasite control agent, it may be used as it is, and together with suitable adjuvants, powders, granules, tablets, powders, capsules, liquid agents, emulsions, aqueous suspensions. It can also be formulated and used in various forms such as a suspending agent and an oily suspension. In addition to the above-mentioned preparation forms, any preparation forms used in the normal field can be used as long as the object of the present invention is met.
  • adjuvant used in the preparation examples include anionic surfactants and nonionic surfactants exemplified as the above-mentioned preparation adjuvants for agricultural and horticultural pest control agents; positive agents such as cetyltrimethylammonium bromide.
  • Ionic surfactants water, acetone, acetonitrile, N-methylacetamide, N, N-dimethylacetamide, N, N-dimethylformamide, 2-pyrrolidone, N-methyl-2-pyrrolidone, kerosene, triacetin, methanol, Ethanol, isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, polyethylene glycol, liquid polyoxyethylene glycol, butyl diglycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl Solvents such as ether, diethylene glycol normal butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol normal butyl ether; oxidations such as butylhydroxyanisole, butylhydroxytoluene, ascorbic acid, sodium metabisulfite, propyl gallate, sodium thiosulfate Inhibitors; Film
  • each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention.
  • it can be used by appropriately selecting from those known in the field, and further, selected from various adjuvants used in the above-mentioned agricultural and horticultural fields. You can also
  • the compounding ratio (weight ratio) of the compound of formula (I) and various adjuvants is usually about 0.1: 99.9 to 90:10. In actual use of these preparations, use them as they are, or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. Can be used.
  • Administration of the compound of formula (I) to the host animal is performed orally or parenterally.
  • the oral administration method include a method of administering tablets, liquid agents, capsules, wafers, biscuits, minced meat, and other feeds containing the compound of formula (I).
  • a parenteral administration method for example, a compound of formula (I) is prepared into an appropriate formulation and then taken into the body by intravenous administration, intramuscular administration, intradermal administration, subcutaneous administration, etc .; spot-on (spot -on) treatment, pour-on treatment, spray treatment, and the like; and a method of embedding a resin piece containing the compound of formula (I) under the skin of a host animal.
  • the dose of the compound of formula (I) to the host animal varies depending on the administration method, administration purpose, disease symptoms, etc., but is usually 0.01 mg to 100 g, preferably 0.1 mg to 1 kg body weight of the host animal. It is appropriate to administer at a rate of 10 g.
  • the present invention includes a method for controlling pests according to the administration method or dosage as described above, particularly a method for controlling ectoparasites or endoparasites.
  • the present invention includes a prophylactic or therapeutic agent for parasite-derived animal diseases containing the compound of formula (I) as an active ingredient, and a method for preventing or treating parasite-derived animal diseases.
  • the present invention includes a composition for controlling mixed pests in which various components as described above are mixed or used together, and a method for controlling pests using the composition, particularly a method for controlling ectoparasites or endoparasites. Is also included.
  • R 1 is a hydrogen atom, alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, optionally substituted with A Alkynyl, halogen, cyano, aryl optionally substituted with halogen, heterocyclic group optionally substituted with alkyl, C ⁇ NOR 2 , C ⁇ NNR 4 R 5 , COR 2 , COOR 2 , OR 2 , S (O ) n R 3 , NR 4 R 5 , N 3 or CONR 4 R 5 ;
  • X is alkyl, hydroxyalkyl, alkenyl, alkynyl, aryl, halogen, haloalkyl, cyano, nitro, NR 4 R 5 , S (O) n R 3 , OR 2 , COR 2 or COOR 2 ;
  • Y is
  • R 1 is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen , Cyano, OR 2 , S (O) n R 3 or NR 4 R 5 ;
  • X is alkyl, alkenyl, alkynyl, halogen, haloalkyl, cyano or nitro;
  • A is halogen, OR 2 , S (O) n R 3 , NR 4 R 5 , cyano, cycloalkyl, aryl or a heterocyclic group;
  • R 2 is a hydrogen atom, alkyl, alkenyl, alkynyl, haloalkyl or aryl, a triazolopyrimidine derivative or a salt thereof as an active ingredient Contains pest control agents.
  • R 3 , R 4 , R 5 , Y, Z, m, and n have
  • R 1 ⁇ is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A , Halogen, cyano, OR 2 or S (O) n R 3 ;
  • X is alkyl, alkenyl, alkynyl, halogen, haloalkyl, cyano or nitro;
  • A is halogen, OR 2 , S (O) n R 3 , NR 4 R 5 , cyano, cycloalkyl, aryl or heterocyclic group;
  • R 2 is a hydrogen atom, alkyl, alkenyl, alkynyl, haloalkyl or aryl; and
  • m is an integer of 2 to 4, a triazolopyrimidine derivative Or its salt.
  • R 3 , R 4 , R 5 , Y, Z, and n are as defined in (1) above.
  • Synthesis example 1 Synthesis of 7- [2-chloro-5- (trifluoromethyl) phenyl] -5-methyl [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 18)
  • 2-Chloro A mixed solution of 1.19 g of methyl -5-trifluoromethylbenzoate, 2 ml of acetone and 10 ml of tetrahydrofuran was ice-cooled, and 432 mg of solid sodium ethoxide was added little by little.
  • Synthesis example 2 Synthesis of 5-chloro-7- [2-chloro-4- (trifluoromethyl) phenyl] [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 21) (1) 5,7 A suspension of 919 mg of dihydroxy [1,2,4] triazolo [1,5-a] pyrimidine and 3 ml of phosphorus oxychloride was refluxed for 3 hours. After completion of the reaction, excess phosphorus oxychloride was distilled off from the obtained transparent reaction solution, 10 ml of ice water was carefully added, and the mixture was extracted with ethyl acetate.
  • Synthesis example 4 Synthesis of 7- [2-chloro-6- (trifluoromethyl) pyridin-3-yl] -5-methyl [1,2,4] troazolo [1,5-a] pyrimidine (Compound No. 29) ) 1.18 g of 3-acetyl-2-chloro-6- (trifluoromethyl) pyridine and 843 mg of N, N-dimethylacetamide dimethylacetal were reacted overnight at 100 ° C. in 11 ml of toluene.
  • Synthesis example 5 Synthesis of 7- [2-chloro-4- (trifluoromethyl) phenyl] -6-fluoro-5-methyl [1,2,4] troazolo [1,5-a] pyrimidine (Compound No. 34) ) 4.2 g of ethyl 2-fluoro-3-oxobutanoate was dissolved in 8 mL of acetic acid, and 2 g of 3-amino-1H-1,2,4-triazole was added and reacted at 100 ° C. for 2 hours.
  • reaction solution is returned to room temperature, the precipitated solid is filtered, washed with methanol, and washed with 6-fluoro-7-hydroxy-5-methyl [1,2,4] troazolo [1,5-a] pyrimidine (intermediate No. XV- 4) 407 mg was obtained as white crystals.
  • Table 3 lists representative examples of the compound of the formula (IV) in the above production method [1]. These compounds can be synthesized based on the above synthesis examples or the various production methods described above.
  • No. represents intermediate No.
  • Me represents methyl
  • i-Bu represents isobutyl.
  • 1 H-NMR is shown in Table 4 for the compounds described in Table 3.
  • Table 5 shows representative examples of the compound of formula (XV) in the production method [5]. These compounds can be synthesized based on the above synthesis examples or the various production methods described above.
  • No. represents intermediate No.
  • Me represents methyl
  • Et represents ethyl
  • i-Pr represents isopropyl
  • Table 1 shows the 1 H-NMR for the compounds whose physical properties in Table 5 are amorphous.
  • Table 7 lists representative examples of the compound of formula (XVI) in the above production method [5]. These compounds can be synthesized based on the above synthesis examples or the various production methods described above. In Table 7, No. represents intermediate No., Me represents methyl, Et represents ethyl, i-Pr represents isopropyl, and the temperatures shown as physical properties are melting points. Table 8 shows the 1 H-NMR for the compounds whose physical properties in Table 7 are solid or oil.
  • Table 9 shows representative examples of the compound of formula (VII) in the above production method [2]. These compounds can be synthesized based on the above synthesis examples or the various production methods described above. In Table 9, No. indicates intermediate No. Further, 1 H-NMR is shown in Table 10 for the compounds described in Table 9.
  • Test Example 1 Effect test on peach aphid Japanese radish leaves were inserted into a test tube containing water, and about 20 first-instar larvae were released on the leaves. The next day, after counting the number of larvae parasitic on radish leaves, the parasitic radish leaves were immersed in a chemical solution adjusted to a concentration of 200 ppm of the compound of formula (I) for about 10 seconds. After the chemical solution was air-dried, it was left in a constant temperature room at 25 ° C. with illumination. Five days after the treatment, the viability of the peach aphid was determined, and the mortality rate was determined by the following formula. The detached insects and abnormal insects were regarded as dead insects. When the compound Nos. 13, 20, 32, 33, 48, 49 and 53 were tested, all the compounds showed a death rate of 90% or more.
  • Test Example 2 Effect test on green planthopper Rice seedlings were immersed for about 10 seconds in a chemical solution adjusted so that the concentration of the compound of formula (I) was 200 ppm. After the chemical solution was air-dried, the root was wrapped with wet absorbent cotton and placed in a test tube. Ten 10-year-old larvae of the green planthopper were released into this, and the tube mouth was covered with gauze and left in a constant temperature room at 25 ° C. Five days after the insect release, the dead planthopper was judged to be alive or dead, and the mortality rate was determined by the following formula. Compound Nos.
  • Death rate (%) (Number of dead insects / Number of dead insects) ⁇ 100
  • Test example 3 Effect test on silver leaf whitefly Silver leaf whitefly 1-2 years old infested cucumber seedlings infested with a chemical solution adjusted so that the concentration of the compound of formula (I) is 200 ppm using a hand spray Processed. After the chemical solution was air-dried, it was left in a constant temperature room at 25 ° C. with illumination. Seven days after the treatment, the number of old larvae was examined, and the control efficiency (%) was determined by the following formula. When the compound Nos. 1, 5, 7, 13, 18, 29, 32, 33, 48 and 49 were tested, all the compounds showed a control efficiency of 80% or more.
  • Control efficiency (%) (1 ⁇ (Ta ⁇ Cb) / (Tb ⁇ Ca)) ⁇ 100
  • Ta old larvae after treatment in treated cucumber seedlings
  • Tb Number of 1-2 instar larvae before treatment in treated cucumber seedlings
  • Ca number of old larvae after treatment in untreated cucumber seedlings
  • Cb Number of 1-2 instar larvae before treatment in untreated cucumber seedlings
  • Test Example 4 Medicinal Efficacy Test Using Dogs against Phytophyllum Tick
  • a dog (beagle, 8 months old) was administered a gelatin capsule containing 10 mg / kg body weight of the compound of formula (I), and immediately after that about 50 young mite mites were collected. Release to the pinna of the dog and let it artificially infest. After the treatment, observe the number of infestations, the number of drops, and the life and death of the fallen spider mites. As a result, the compound of formula (I) drops or kills the parasitic spider mite.
  • Test Example 5 Medicinal Efficacy Test Using Dogs for Cat Fleas A dog (beagle, 8 months old) was administered a gelatin capsule containing 10 mg / kg body weight of the compound of formula (I), and immediately after that about 100 cat flea non-blood-sucking adults were administered. Let go on the back coat and let it artificially infest. The compound of the formula (I) exhibits a hatching-inhibiting effect on the treated laying eggs of adults.
  • Formulation Example 1 (1) Compound of formula (I) 20 parts by weight (2) Clay 70 parts by weight (3) White carbon 5 parts by weight (4) Sodium polycarboxylate 3 parts by weight (5) Sodium alkylnaphthalenesulfonate 2 parts by weight or more Mix things uniformly to make a wettable powder.
  • Formulation Example 2 (1) Compound of formula (I) 5 parts by weight (2) Talc 60 parts by weight (3) Calcium carbonate 34.5 parts by weight (4) Liquid paraffin To do.
  • Formulation Example 3 (1) Compound of formula (I) 20 parts by weight (2) N, N-dimethylacetamide 20 parts by weight (3) Polyoxyethylene tristyryl phenyl ether 10 parts by weight (4) Calcium dodecylbenzenesulfonate 2 parts by weight (5 ) Xylene 48 parts by weight or more are uniformly mixed and dissolved to prepare an emulsion.
  • Formulation Example 4 (1) Clay 68 parts by weight (2) Sodium lignin sulfonate 2 parts by weight (3) Polyoxyethylene alkylaryl sulfate 5 parts by weight (4) White carbon 25 parts by weight A mixture of each component and formula (I) The compound is mixed at a weight ratio of 4: 1 to obtain a wettable powder.
  • Formulation Example 5 (1) Compound of formula (I) 50 parts by weight (2) Sodium alkylnaphthalenesulfonate formaldehyde condensate 2 parts by weight (3) Silicone oil 0.2 part by weight (4) Water 47.8 parts by weight or more uniform (5) 5 parts by weight of sodium polycarboxylate (6) 42.8 parts by weight of anhydrous sodium sulfate are added to the stock solution mixed and pulverized, and mixed uniformly, granulated, and dried to obtain a granulated wettable powder.
  • Formulation Example 6 (1) Compound of formula (I) 5 parts by weight (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) Polyoxyethylene alkyl ether phosphate 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight Parts (1) to (3) are mixed uniformly in advance, diluted with an appropriate amount of acetone, sprayed onto (4), and acetone is removed to form granules.
  • Formulation Example 7 (1) Compound of formula (I) 2.5 parts by weight (2) N, N-dimethylacetamide 2.5 parts by weight (3) Soybean oil 95.0 parts by weight or more are uniformly mixed and dissolved to form a trace amount Use as an ultra low volume formulation.
  • Formulation Example 8 (1) Compound of formula (I) 40 parts by weight (2) Polyoxyethylene tristyryl phenyl ether potassium phosphate 4 parts by weight (3) Silicone oil 0.2 parts by weight (4) Xanthan gum 0.1 parts by weight (5) Ethylene glycol 5 parts by weight (6) Water 50.7 parts by weight or more are uniformly mixed and ground to obtain an aqueous suspension.
  • Formulation Example 9 (1) Compound of formula (I) 10 parts by weight (2) Diethylene glycol monoethyl ether 80 parts by weight (3) Polyoxyethylene alkyl ether 10 parts by weight or more of ingredients are mixed uniformly to obtain an aqueous solution.
  • the pest control agent containing the triazolopyrimidine derivative or salt thereof of the present invention as an active ingredient is sufficiently effective at a low dose, and is used as a control agent for various pests in the field of agriculture and horticulture, and is harmful to animals. It is useful as an animal parasite control agent that is a biological control agent.

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  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Engineering & Computer Science (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne un nouvel agent antiparasitaire. L'agent antiparasitaire contient un dérivé triazolopyrimidine représenté par la formule (I) ou un sel de celui-ci comme principe actif. (Dans la formule, R1 représente un atome d’hydrogène, un alkyle qui peut être substitué par A, un cycloalkyle qui peut être substitué par A, un alcényle qui peut être substitué par A, un alcynyle qui peut être substitué par A, ou équivalents ; X représente un alkyle, un hydroxyalkyle, un alcényle, un alcynyle, un aryle ou équivalents ; Y représente un atome d'hydrogène ou de fluor ; Z représente CH, CX ou N ; A représente un halogène, un cyano, un nitro ou équivalents ; et m représente un entier de 1 à 4).
PCT/JP2009/064359 2008-08-14 2009-08-14 Agent antiparasitaire contenant un dérivé triazolopyrimidine ou un sel de celui-ci WO2010018868A1 (fr)

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018154133A1 (fr) 2017-02-27 2018-08-30 Janssen Pharmaceutica Nv Dérivés de [1,2,4]-triazolo [1,5-a]-pyrimidinyle substitués par de la pipéridine, de la morpholine ou de la pipérazine utilisés en tant qu'inhibiteurs d'oga
US10287286B2 (en) 2015-03-18 2019-05-14 Takeda Pharmaceutical Company Limited Compounds
CN109890824A (zh) * 2016-11-02 2019-06-14 詹森药业有限公司 作为pde2抑制剂的[1,2,4]三唑并[1,5-a]嘧啶化合物
US10336775B2 (en) 2014-08-28 2019-07-02 Asceneuron Sa Glycosidase inhibitors
US10556902B2 (en) 2016-02-25 2020-02-11 Asceneuron Sa Glycosidase inhibitors
US10696668B2 (en) 2016-02-25 2020-06-30 Asceneuron Sa Acid addition salts of piperazine derivatives
US11213525B2 (en) 2017-08-24 2022-01-04 Asceneuron Sa Linear glycosidase inhibitors
US11261183B2 (en) 2016-02-25 2022-03-01 Asceneuron Sa Sulfoximine glycosidase inhibitors
CN115605482A (zh) * 2020-06-01 2023-01-13 优迈特株式会社（Jp） 含氟稠环嘧啶化合物及其制造方法
US11612599B2 (en) 2016-02-25 2023-03-28 Asceneuron Sa Glycosidase inhibitors
US11731972B2 (en) 2018-08-22 2023-08-22 Asceneuron Sa Spiro compounds as glycosidase inhibitors
US11795165B2 (en) 2018-08-22 2023-10-24 Asceneuron Sa Tetrahydro-benzoazepine glycosidase inhibitors
US11814734B2 (en) 2019-05-13 2023-11-14 Ecolab Usa Inc. 1,2,4-triazolo[1,5-a] pyrimidine derivative as copper corrosion inhibitor

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2443136A (en) * 1946-04-11 1948-06-08 Gen Aniline & Film Corp Photographic elements containing 1, 3, 4-triazaindolizine cyanine dyes
JPS4835456B1 (fr) * 1970-12-28 1973-10-27
US4444774A (en) * 1982-07-29 1984-04-24 American Cyanamid Company 7-Heteroaryl[1,2,4]triazolo[1,5-a]pyrimidines
JP2002503664A (ja) * 1998-02-11 2002-02-05 アメリカン・サイアナミド・カンパニー 殺菌剤７−アルキル−トリアゾロピリミジン
JP2002308879A (ja) * 2001-04-13 2002-10-23 Nippon Soda Co Ltd ５−ハロアルキル−アゾロピリミジン化合物、製造方法及び有害生物防除剤
WO2004108136A1 (fr) * 2003-06-04 2004-12-16 Vernalis (Cambridge) Limited Triazolo`1,5-a!pyrimidines et leur utilisation en medecine
WO2006092428A2 (fr) * 2005-03-02 2006-09-08 Basf Aktiengesellschaft 7-amino-azolopyrimidine 2-substituee, son procede de fabrication et son utilisation pour lutter contre les champignons nuisibles, et agents renfermant ce compose
JP2007505077A (ja) * 2003-09-12 2007-03-08 ビーエーエスエフ　アクチェンゲゼルシャフト 動物害虫を駆除するために用いる６−ハロゲノ−［１，２，４］トリアゾロ［１，５−ａ］ピリミジン類

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2443136A (en) * 1946-04-11 1948-06-08 Gen Aniline & Film Corp Photographic elements containing 1, 3, 4-triazaindolizine cyanine dyes
JPS4835456B1 (fr) * 1970-12-28 1973-10-27
US4444774A (en) * 1982-07-29 1984-04-24 American Cyanamid Company 7-Heteroaryl[1,2,4]triazolo[1,5-a]pyrimidines
JP2002503664A (ja) * 1998-02-11 2002-02-05 アメリカン・サイアナミド・カンパニー 殺菌剤７−アルキル−トリアゾロピリミジン
JP2002308879A (ja) * 2001-04-13 2002-10-23 Nippon Soda Co Ltd ５−ハロアルキル−アゾロピリミジン化合物、製造方法及び有害生物防除剤
WO2004108136A1 (fr) * 2003-06-04 2004-12-16 Vernalis (Cambridge) Limited Triazolo`1,5-a!pyrimidines et leur utilisation en medecine
JP2007505077A (ja) * 2003-09-12 2007-03-08 ビーエーエスエフ　アクチェンゲゼルシャフト 動物害虫を駆除するために用いる６−ハロゲノ−［１，２，４］トリアゾロ［１，５−ａ］ピリミジン類
WO2006092428A2 (fr) * 2005-03-02 2006-09-08 Basf Aktiengesellschaft 7-amino-azolopyrimidine 2-substituee, son procede de fabrication et son utilisation pour lutter contre les champignons nuisibles, et agents renfermant ce compose

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
"ACS Symposium Series, Synth. Chem. Agrochem. III", vol. 504, 1992, article SELBY, T.P ET AL.: "7-Phenyl-1, 2, 4-triazolo [1, 5-a]pyrimidines and related heterocycles. A new family of bleaching herbicides", pages: 91 - 102 *
DESENKO, S.M. ET AL.: "Fluorine-containing dihydro derivatives of 1, 2, 4-triazolo[l, 5-a] pyrimidine", DOPOVIDI AKADEMII NAUK UKRAINI, vol. 8, 1993, pages 122 - 125 *
PETRICH, S.A ET AL.: "The application of unsymmetrical vinylogous iminium salts and related synthons to the preparation of monosubstituted triazolo[l, 5-a]pyrimidines", TETRAHEDRON, vol. 50, no. 42, 1994, pages 12113 - 12124 *

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10336775B2 (en) 2014-08-28 2019-07-02 Asceneuron Sa Glycosidase inhibitors
US11046712B2 (en) 2014-08-28 2021-06-29 Asceneuron Sa Glycosidase inhibitors
US10287286B2 (en) 2015-03-18 2019-05-14 Takeda Pharmaceutical Company Limited Compounds
US11591327B2 (en) 2016-02-25 2023-02-28 Asceneuron Sa Acid addition salts of piperazine derivatives
US11261183B2 (en) 2016-02-25 2022-03-01 Asceneuron Sa Sulfoximine glycosidase inhibitors
US10696668B2 (en) 2016-02-25 2020-06-30 Asceneuron Sa Acid addition salts of piperazine derivatives
US10995090B2 (en) 2016-02-25 2021-05-04 Asceneuron Sa Substituted dihydrobenzofuran glycosidase inhibitors
US10556902B2 (en) 2016-02-25 2020-02-11 Asceneuron Sa Glycosidase inhibitors
US11612599B2 (en) 2016-02-25 2023-03-28 Asceneuron Sa Glycosidase inhibitors
CN109890824A (zh) * 2016-11-02 2019-06-14 詹森药业有限公司 作为pde2抑制剂的[1,2,4]三唑并[1,5-a]嘧啶化合物
CN109890824B (zh) * 2016-11-02 2022-05-24 詹森药业有限公司 作为pde2抑制剂的[1,2,4]三唑并[1,5-a]嘧啶化合物
WO2018154133A1 (fr) 2017-02-27 2018-08-30 Janssen Pharmaceutica Nv Dérivés de [1,2,4]-triazolo [1,5-a]-pyrimidinyle substitués par de la pipéridine, de la morpholine ou de la pipérazine utilisés en tant qu'inhibiteurs d'oga
US11213525B2 (en) 2017-08-24 2022-01-04 Asceneuron Sa Linear glycosidase inhibitors
US11731972B2 (en) 2018-08-22 2023-08-22 Asceneuron Sa Spiro compounds as glycosidase inhibitors
US11795165B2 (en) 2018-08-22 2023-10-24 Asceneuron Sa Tetrahydro-benzoazepine glycosidase inhibitors
US11814734B2 (en) 2019-05-13 2023-11-14 Ecolab Usa Inc. 1,2,4-triazolo[1,5-a] pyrimidine derivative as copper corrosion inhibitor
CN115605482A (zh) * 2020-06-01 2023-01-13 优迈特株式会社（Jp） 含氟稠环嘧啶化合物及其制造方法
CN115605482B (zh) * 2020-06-01 2024-01-05 优迈特株式会社 含氟稠环嘧啶化合物及其制造方法

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