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WO2010018853A1 - Dérivé pyridyle-triazolopyrimidine ou sel de celui-ci, et agent de lutte contre les organismes nocifs le comprenant - Google Patents

Dérivé pyridyle-triazolopyrimidine ou sel de celui-ci, et agent de lutte contre les organismes nocifs le comprenant Download PDF

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Publication number
WO2010018853A1
WO2010018853A1 PCT/JP2009/064275 JP2009064275W WO2010018853A1 WO 2010018853 A1 WO2010018853 A1 WO 2010018853A1 JP 2009064275 W JP2009064275 W JP 2009064275W WO 2010018853 A1 WO2010018853 A1 WO 2010018853A1
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alkyl
compound
optionally substituted
reaction
formula
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Japanese (ja)
Inventor
隆弘 芳賀
博彦 木村
雅之 森田
剛 上田
寿彦 植木
和久 桐山
幸太郎 吉田
卓 ▲濱▼本
哲也 小玉
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Ishihara Sangyo Kaisha Ltd
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Ishihara Sangyo Kaisha Ltd
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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
    • 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 pest control agent containing a novel pyridyl-triazolopyrimidine derivative or a salt thereof as an active ingredient.
  • Patent Document 1 discloses the use of a triazolopyrimidine derivative having a specific chemical structure as a nematicide. However, these compounds differ in chemical structure from the compounds of the present invention.
  • Patent Document 2 discloses a method for inhibiting or treating cancerous tumor cell proliferation and related diseases by administering an effective amount of a triazolopyrimidine derivative to a mammal. However, there is no description of the compounds of the present invention and the use of the compounds of the present invention as pest control agents.
  • the present inventors have made various studies on pyridyl-triazolopyrimidine derivatives in order to find better pest control agents. As a result, it was found that the novel pyridyl-triazolopyrimidine derivative has a very high control effect against pests at a low dosage, and also has safety against crops, pest natural enemies or mammals. The present invention has been completed.
  • R 1 is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen atom, cyano, aryl , A heterocyclic group which may be substituted with alkyl, CH ⁇ NOR 2 , CH ⁇ NNR 4 R 5 , COR 2 , COOR 2 , OR 2 , S (O) n R 3 , NR 4 R 5 or CONR 4 R 5 X is alkyl, alkenyl, alkynyl, aryl, heterocyclic group, halogen atom, haloalkyl, cyano, nitro, NR 4 R 5 , CONR 4 R 5 , S (O) n R 3 , OR 2 , COR 2 or COOR 2 ; A is a halogen atom, OR 2 , S (O) n R 3 , OS (O) n R 3 , NR 4 R 5
  • M is an integer of 1 to 4; n is an integer of 0 to 2], or a salt thereof.
  • the present invention also relates to a pest control agent comprising a pyridyl-triazolopyrimidine derivative of the formula (I) or a salt thereof as an active ingredient.
  • the pest control agent comprising the pyridyl-triazolopyrimidine derivative of the formula (I) or a salt thereof as an active ingredient has a very high control effect against pests with a low dose.
  • each X may be the same or different.
  • the halogen atom in the formula (I) or the halogen atom as a substituent include each atom of fluorine, chlorine, bromine or iodine.
  • the number of halogen atoms as a substituent may be 1 or 2 or more, and in the case of 2 or more, each halogen atom may be the same or different. Further, the halogen atom may be substituted at any position.
  • the alkyl in the formula (I) may be linear or branched, and specific examples thereof include C 1 such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl. -6 and so on.
  • Examples of cycloalkyl in formula (I) include C 3-6 such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • the alkenyl in the formula (I) may be linear or branched, and specific examples thereof include vinyl, 1-propenyl, allyl, isopropenyl, 1-butenyl, 1,3-butadienyl, -C 2-6 such as hexenyl.
  • the alkynyl in the formula (I) may be linear or branched, and specific examples thereof include ethynyl, 2-butynyl, 2-pentynyl, 3-methyl-1-butynyl, 2-pentene- Examples thereof include C 2-6 such as 4-ynyl and 3-hexynyl.
  • 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.
  • the monocyclic heterocyclic group includes, for example, a 3-membered heterocyclic group such as oxiranyl; furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, dioxolanyl, oxazolyl, oxazolinyl, isoxazolyl, thiazolyl, thiazolinyl, isothiazolyl, imidazolyl, imidazolinyl 5-membered heterocyclic groups such as imidazolidinyl, oxazolidinyl, oxazolidinyl, thiazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, triazolyl, oxadiazolyl, thiadiazol
  • 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
  • the salt of the pyridyl-triazolopyrimidine derivative of the formula (I) includes any agriculturally acceptable salt.
  • examples thereof include ammonium salts such as dimethylammonium salt and triethylammonium salt; hydrochloride Inorganic acid salts such as perchlorate, sulfate and nitrate; organic acid salts such as acetate and methanesulfonate.
  • the pyridyl-triazolopyrimidine derivative of the formula (I) may have isomers such as optical isomers and geometric isomers, but the present invention includes both isomers and isomer mixtures. It is. In the present specification, unless otherwise specified, isomers are described as a mixture. The present invention also includes various isomers other than those described above within the scope of technical common sense in the technical field. Depending on the type of isomer, there may be a chemical structure different from that of the formula (I). However, since those skilled in the art can fully recognize that they are related to isomers, the scope of the present invention. It is clear that it is within.
  • the pyridyl-triazolopyrimidine derivative of the formula (I) or a salt thereof can be produced according to the following production methods [1] to [9] and usual salt production methods, and is also produced according to the synthesis examples described later. be able to. Manufacturing method [1]
  • R 1a is optionally substituted by by alkyl which may be, cycloalkyl which may be substituted by A 1, alkenyl which may be substituted by A 1, A 1 substituted by A 1 alkynyl, A heterocyclic group which may be substituted with aryl or alkyl;
  • a 1 is a halogen atom, OR 2a , S (O) n R 3 , NR 4 R 5a , cyano, alkyl, cycloalkyl, aryl, heterocyclic group , SCH 2 COOR 2a , NHNR 4 R 5a or —CH (CN) 2 ;
  • R 2a is a hydrogen atom, alkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, acetyl, benzyl or aryl;
  • R 5a is a hydrogen atom , alkyl, cycloalkyl, haloalkyl, COR
  • the compound of the formula (II) and the compound of the formula (III) are condensed to obtain the ⁇ , ⁇ -unsaturated ketone derivative of the formula (IV), the reaction of the formula (IV)
  • the latter reaction consists of condensing the compound with the compound of formula (V) to obtain the [1,2,4] triazolo [1,5-a] pyrimidine derivative of formula (I-1).
  • the compound of formula (III) can be used at a ratio of 0.8 to 5 equivalents, preferably 1 to 3.5 equivalents, per 1 mol of the compound of formula (II).
  • This reaction can be performed in the presence of a solvent, if necessary. Any solvent may be used as long as it is inert to the reaction.
  • alcohols such as methanol, ethanol, propanol and butanol
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • pentane, hexane, heptane Aliphatic hydrocarbons such as petroleum ether, ligroin and petroleum benzine
  • ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane
  • esters such as methyl acetate and ethyl acetate
  • acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidinone
  • sulfoxides such as dimethyl sulfoxide
  • sulfones such as sulfolane
  • hexamethyl phosphorami Phosphoric acid amides such as;
  • the compound of formula (V) can be used in a proportion of 0.8 to 10 equivalents, preferably 1 to 2.5 equivalents, relative to 1 mol of the compound of formula (IV).
  • This reaction can be performed in the presence of a solvent, if necessary. Any solvent may be used as long as it is inert to the reaction, for example, 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 amides such as hexamethylphosphoramide; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane; and mixed solvents thereof. Acids are
  • Y is a halogen atom
  • R 3 X and m are as defined above.
  • Examples of the halogen atom for Y include fluorine, chlorine, bromine and iodine atoms.
  • the production method [2] includes a reaction in the first half to obtain an ⁇ , ⁇ -unsaturated ketone derivative of the formula (VII) by reacting a compound of the formula (II), carbon disulfide and a compound of the formula (VI).
  • the latter reaction consists of condensing the compound of formula (VII) with the compound of formula (V) to obtain the [1,2,4] triazolo [1,5-a] pyrimidine derivative of formula (I-2).
  • carbon disulfide and the compound of formula (VI) are used in an amount of 0.8 to 5 equivalents, preferably 1 to 3 equivalents, per 1 mol of the compound of formula (II). it can.
  • the compound of formula (VII) can be produced by reacting in the presence of a base and a solvent.
  • the base include alkali metal hydrides such as sodium hydride and potassium hydride; alkali 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; 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 may be any solvent as long as it is inert to the reaction, and examples thereof include the same ones as in the reaction in the first half of the production method [1].
  • the reaction temperature is usually 0 to 100 ° C., preferably 10 to 50 ° C.
  • the reaction time is usually 6 to 48 hours.
  • the compound of the formula (V) can be used in a proportion of 0.8 to 5 equivalents, preferably 1 to 3 equivalents, relative to 1 mol of the compound of the formula (VII).
  • This reaction can be performed in the presence of a base and a solvent, if necessary.
  • the base examples include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metals such as sodium and potassium; sodium methoxide and sodium Alkali metal alkoxides such as ethoxide and potassium tertiary butoxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; such as triethylamine and pyridine Organic bases; and the like.
  • the base can be used in an amount of 1 to 5 equivalents, preferably 1 to 3 equivalents, relative to 1 mol of the compound of formula (V).
  • the solvent may be any solvent as long as it is inert to the reaction, and examples thereof include the same ones as in the reaction in the first half of the production method [1].
  • the reaction temperature is usually 100 to 200 ° C.
  • the reaction time is usually 0.1 to 10 hours. Manufacturing method [3]
  • R 3 , X and m are as described above, and na is an integer of 1 to 2.
  • the oxidizing agent used in the above reaction examples include hydrogen peroxide, peracetic acid, m-chloroperbenzoic acid, and the like.
  • the solvent may be any solvent that is inert to the reaction, for example, halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane; ketones such as acetone and dimethyl ethyl ketone; Mention may be made of 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 oxidizing agent can be used in a ratio of 1 to 3 equivalents per 1 mol of the compound of the formula (I-2).
  • the reaction temperature is usually room temperature to reflux temperature.
  • the reaction time is usually 1 to 24 hours. Manufacturing method [4]
  • R 1b is optionally substituted by by alkyl which may be, cycloalkyl which may be substituted by A 1, alkenyl which may be substituted by A 1, A 1 substituted by A 1 alkynyl, A halogen atom, cyano, aryl, an optionally substituted heterocyclic group, OR 2a or NR 4 R 5a ; R 2a , R 4 , R 5a , A 1 , X and m are as defined above.
  • the compound of the formula (I-3) is reacted with a nucleophile in the presence of a solvent to thereby react [1,2,4] triazolo [1,5- a] Pyrimidine derivatives can be produced.
  • nucleophile examples include alkali metal alkoxides such as sodium methoxide and sodium ethoxide; alkali metal mercaptides such as sodium methyl mercaptan; primary or secondary amines such as methylamine, dimethylamine and piperidine; And organometallic reagents such as bromide, ethylmagnesium bromide, and phenylmagnesium bromide; fluorinating agents such as potassium fluoride, cesium fluoride, and tetrabutylammonium fluoride;
  • the nucleophilic reagent can be used in a ratio of 1 to 5 equivalents, preferably 1 to 3 equivalents, relative to 1 mol of the compound of formula (I-3).
  • Any solvent may be used as long as it is inert to the reaction.
  • alcohols such as methanol, ethanol, propanol and butanol
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • Aliphatic ethers such as petroleum ether, ligroin and petroleum benzine
  • ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane
  • esters such as methyl acetate and ethyl acetate
  • acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidinone
  • sulfoxides such as dimethyl sulfoxide; and mixed solvents thereof.
  • the reaction temperature is usually ⁇ 100 to
  • R 8 is alkyl; R 1a , X and m are as described above.
  • the compound of formula (VIII) can be used in a proportion of 0.8 equivalent to large excess, preferably 1 to 10 equivalents, relative to 1 mol of the compound of formula (II).
  • the compound of formula (IX) can be produced by reacting in the presence of a base and a solvent.
  • the base include those similar to the reaction in the first half of the above production method [2].
  • the base can be used in a proportion of 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to the compound of formula (II). Any solvent may be used as long as it is inert to the reaction.
  • alcohols such as methanol, ethanol, propanol and butanol
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • pentane, hexane, heptane Aliphatic hydrocarbons such as petroleum ether, ligroin and petroleum benzine
  • ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane
  • N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl Acid amides such as pyrrolidinone
  • sulfoxides such as dimethyl sulfoxide
  • sulfones such as sulfolane
  • halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; and a mixed solvent thereof.
  • You can gel, among others ethers are
  • the compound of the formula (V) can be used in a proportion of 0.8 to 10 equivalents, preferably 1 to 2.5 equivalents, relative to 1 mol of the compound of the formula (IX).
  • the compound of formula (I-5) can be produced in the presence of a solvent.
  • the solvent may be any solvent as long as it is inert to the reaction, and examples thereof include the same ones as in the reaction in the latter half of the above production method [1]. Among them, carboxylic acids are preferable.
  • Formula (IX) is a liquid at normal temperature
  • the reaction in the latter half of the production method [5] can be carried out without isolating the compound.
  • the reaction temperature is usually 50 to 150 ° C., desirably 80 to 120 ° C.
  • the reaction time is usually 0.5 to 100 hours. Manufacturing method [6]
  • R 1c is a halogen atom
  • R 9 and R 10 are each independently alkyl
  • X, Y, and m are as described above.
  • Examples of the halogen atom for R 1c include fluorine, chlorine and bromine atoms.
  • the compound of the formula (I-6) can be produced by the reactions (a) to (e) above. Each reaction is described in detail below.
  • the compound of the formula (XII) can be produced by reacting the compound of the formula (X) with the compound of the formula (XI) in the presence of a base and a solvent.
  • the compound of the formula (XI) can be used in a proportion of 0.8 equivalent to a large excess, desirably 1 to 30 equivalent, relative to 1 mol of the compound of the formula (X).
  • Examples of the base include those similar to the reaction in the first half of the above production method [2].
  • 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 (X).
  • the solvent may be any solvent as long as it is inert to the reaction, and examples thereof include those similar to the reaction in the first half of the above production method [5]. Among them, 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.
  • the compound of the formula (XIII) can be produced by hydrolyzing the compound of the formula (XII) 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 a proportion of 1 equivalent to a large excess with respect to the compound of the formula (XII).
  • 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 formula (XIV) can be produced by reacting the compound of formula (XIII) with a halogenating agent in the presence of a solvent.
  • 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 the formula (XIII).
  • the solvent may be any solvent that is inert to 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.
  • (d) 4,5-dihydro-5-oxo [1,2,4] triazolo [1,5-a] pyrimidine derivative of formula (XV) is a compound of formula (XIV) and a compound of formula (V) Can be produced by condensation.
  • the compound of the formula (V) can be used in a ratio of 0.8 to 10 equivalents, desirably 1 to 2.5 equivalents, relative to 1 mol of the compound of the formula (XIV).
  • This reaction can be performed in the presence of a solvent, if necessary. Any solvent may be used as long as it is inert to the reaction. For example, the same reaction as in the first half of the above production method [5] can be mentioned, but acid amides are particularly desirable.
  • 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 5-halo [1,2,4] triazolo [1,5-a] pyrimidine derivative of formula (I-6) is produced by reacting the compound of compound (XV) with a halogenating agent.
  • 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 the formula (XV). This reaction can be performed in the presence of a solvent, if necessary.
  • the solvent may be any solvent that is inert to 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.
  • R 9 , R 1a , X and m are as described above.
  • the compound of formula (X) is reacted with the compound of formula (XVI) to obtain the compound of formula (IX), and the compound of formula (IX) and formula (V)
  • the latter reaction consists of condensing the compound to obtain the [1,2,4] triazolo [1,5-a] pyrimidine derivative of formula (I-5).
  • the compound of the formula (XVI) can be used in a proportion of 0.8 equivalent to a large excess, preferably 1 to 10 equivalents, relative to 1 mol of the compound of the formula (X).
  • the compound of formula (IX) can be produced in the presence of a base and a solvent.
  • the base include those similar to the reaction in the first half of the above production method [5].
  • 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 (X).
  • the solvent may be any solvent as long as it is inert to the reaction, and examples thereof include those similar to the reaction in the first half of the above production method [5].
  • 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 reaction in the latter half of the production process [7] can be carried out in the same manner as the reaction in the latter half of the production process [5]. Manufacturing method [8]
  • R 11 and R 12 are each independently hydrogen, alkyl or cycloalkyl; X, Y and m are as described above.
  • the compound of the formula (I-7) and the halogenating agent are reacted in the presence of a solvent and a small amount of a radical initiator to thereby produce [1,2,4 of the formula (I-8).
  • a triazolo [1,5-a] pyrimidine derivative can be produced. This reaction can be performed under light irradiation as needed.
  • halogenating agent examples include N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide and the like.
  • the halogenating agent can be used in a proportion of 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to the compound of formula (I-7).
  • radical initiator examples include benzoyl peroxide and azobisisobutyronitrile. Any solvent may be used as long as it is inert to the reaction.
  • 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 80 ° C.
  • the reaction time is usually 0.1 to 24 hours. Manufacturing method [9]
  • R 13 is optionally substituted by by alkyl which may be, cycloalkyl which may be substituted by A 1, alkenyl which may be substituted by A 1, A 1 substituted by A 1 alkynyl, A heterocyclic group which may be substituted with a halogen atom, cyano, aryl or alkyl, OR 14 , SR 14 or NR 15 R 16 , wherein R 14 , R 15 and R 16 may each independently be substituted with A 1 ; alkyl, cycloalkyl which may be substituted by A 1, is substituted with an alkenyl or A 1 may be substituted by A 1 be also good alkynyl; R 11, R 12, A 1, X and m are described above It is as follows.
  • the compound of the formula (I-8) is reacted with a nucleophile in the presence of a solvent to give [1,2,4] triazolo [1,5- a] Pyrimidine derivatives can be produced.
  • nucleophiles examples include alkali metal alkoxides such as sodium methoxide and sodium ethoxide; alkali metal haloalkoxides such as sodium trifluoromethyl ethoxide; alkali metal mercaptides such as sodium methyl mercaptan; methylamine and dimethylamine Primary or secondary amines such as pyridine, piperidine, morpholine; organometallic reagents such as methylmagnesium bromide, ethylmagnesium bromide, phenylmagnesium bromide; fluorine such as potassium fluoride, cesium fluoride, tetrabutylammonium fluoride A cyanating agent such as potassium cyanide and sodium cyanide; and the like.
  • alkali metal alkoxides such as sodium methoxide and sodium ethoxide
  • alkali metal haloalkoxides such as sodium trifluoromethyl ethoxide
  • the nucleophilic reagent can be used in a ratio of 1 to 5 equivalents, preferably 1 to 3 equivalents, relative to 1 mol of the compound of the formula (I-8).
  • the solvent may be any solvent as long as it is inert to the reaction, and examples thereof include the same ones as in the reaction of the above production method [4].
  • the reaction temperature is usually ⁇ 100 to 50 ° C., desirably ⁇ 70 to 20 ° C.
  • the reaction time is usually 6 to 48 hours.
  • X a is alkyl, aryl, halogen atom, haloalkyl, cyano, nitro, OR 2b , COR 2b or COOR 2b ;
  • R 2b is alkyl, alkenyl, alkynyl, haloalkyl, cyanoalkyl, alkoxyalkyl, acetyl, Benzyl or aryl;
  • m is as described above), and one or more methods are appropriately selected from the same methods as those described in Synthesis Examples 1 to 13 below.
  • the methyl group at the 5-position on the triazolopyrimidine ring can be appropriately converted to another substituent selected from R 1 .
  • the following formula (I-11) which can be produced by the production method [1], the production method [4] or the production method [5] or the same method as in Synthesis Examples 14 (1) to (4) described later;
  • X b is alkyl, halogen atom, haloalkyl, cyano, OR 2a , COOR 2a acetyl, S (O) n R 3a , NR 4 R 5a or CONR 4 R 5b ;
  • R 3a is alkyl R 1a , R 2a , R 4 , R 5a , m and n are as described above), and the synthesis examples 18 (1), 18 (2), and 18 A specific substituent on the pyridine ring can be appropriately converted to another substituent selected from X by appropriately selecting and executing one or more methods from the same methods as in Example 19.
  • the compound represented by the formula (I-12) may be selected from X by selecting a specific substituent on the pyridine ring by a known substituent conversion reaction in addition to the method similar to the synthesis example described later. Can be appropriately converted to the above substituent.
  • the desirable mode of the pest control agent containing the compound of the present invention is described below.
  • the pest control agent containing the compound 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 parasitics. It is particularly useful as a biocontrol agent.
  • 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, leafhoppers, leafhoppers, scale insects, stink bugs, whitefly, thrips, grasshoppers, fly flies, scarab beetles, tamanayaga, kaburagaga, ants, etc .; Plant parasitic nematodes such as cucumbers, cyst nematodes, nesting nematodes, rice scented nematodes, strawberry nem
  • the agricultural and horticultural pest control agent containing the compound 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. Moreover, the agricultural and horticultural pesticide containing the compound of the present invention is also effective for controlling various resistant pests against drugs such as organic phosphorus agents, carbamate agents, and synthetic pyrethroid agents.
  • the compound of the present invention has excellent osmotic transfer properties, soil harmful insects, mites, nematodes by treating agricultural and horticultural pesticides containing the compound of the present invention on the soil It is possible to control pests on the foliage at the same time as the control of gastropods and isopods.
  • Another desirable embodiment of the pest control agent containing the compound of the present invention is a farm that comprehensively controls the aforementioned plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods, soil pests, etc. Examples include horticultural pest control agents.
  • the agricultural and horticultural pest control agent containing the compound of the present invention is usually a powder, granule, granule wettable powder, wettable powder, aqueous suspension, by mixing the compound with various agricultural adjuvants, Used in various forms such as oil suspensions, aqueous solvents, emulsions, solutions, pastes, aerosols, microdispersions, etc. It can be in any formulation form.
  • 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 Cole sulfate ester salt, alkyl sulfonate salt, alkyl aryl sulfonate salt, aryl sulfonate salt, lignin sulfonate salt, alkyl diphenyl ether disulfonate salt, polystyrene sulfonate salt, alkyl phosphate ester salt, alkyl aryl phosphate salt, styryl Aryl phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl ether
  • 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.
  • auxiliary agents they can be appropriately selected from those known in the art.
  • various commonly used adjuvants such as extenders, thickeners, anti-settling agents, antifreeze agents, dispersion stabilizers, safeners, and antifungal agents can be used.
  • the compounding ratio of the compound of the present invention and various adjuvants is 0.001: 99.999 to 95: 5, preferably 0.005: 99.995 to 90:10.
  • a diluent such as water
  • various spreading agents surfactants, vegetable oils, mineral oils, etc.
  • the active ingredient concentration is preferably 0.5 to 500,000 ppm, and the application amount per unit area is 0.05 to 50,000 g, preferably 1 to 30,000 g of the compound of the present invention per hectare.
  • application of the agricultural and horticultural pest control agent which is another desirable embodiment of the pest control agent containing the compound of the present invention, is performed according to the application of the pest control agent.
  • the present invention also 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.
  • Application of various preparations or dilutions of agricultural and horticultural pesticides containing the compound of the present invention is usually performed by a commonly used application method, that is, spraying (for example, spraying, spraying, misting, atomizing, It can be carried out by powder application, water surface application, etc.), soil application (mixing, irrigation, etc.), surface application (application, powder coating, coating, etc.), immersion poison bait, etc. It is also possible to feed livestock with the above-mentioned active ingredient mixed with feed to inhibit the occurrence and growth of harmful insects, particularly harmful insects, in the excreta. It can also be applied by the so-called ultra-low concentration low volume method. In this method, it is possible to contain 100% of the active ingredient.
  • the agricultural and horticultural pest control agent containing the compound of the present invention can be mixed or used in combination with other agricultural chemicals, fertilizers, safeners, etc.
  • Other agrochemicals include herbicides, insecticides, acaricides, nematicides, soil insecticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, plant growth regulators, etc. It is done.
  • a mixed pest control composition in which the compound of the present invention and one or more active compound compounds of other agricultural chemicals are used in combination or in combination is preferred in terms of application range, timing of chemical treatment, control activity, etc. It is possible to improve.
  • the compound of the present invention and the other active ingredient compounds of other agricultural chemicals may be prepared separately and mixed at the time of spraying, or both may be used together.
  • the present invention includes such a composition for controlling mixed pests.
  • the mixing ratio between the compound of the present invention and the active ingredient compound of other agricultural chemicals cannot be defined unconditionally due to differences in weather conditions, formulation form, application time, application location, type of pests and occurrence, etc., but generally from 1: 300 to 300: 1, preferably 1: 100 to 100: 1.
  • the appropriate amount to be applied is 0.1 to 50,000 g, preferably 1 to 30,000 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.
  • 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;
  • bactericidal active ingredient compounds in the above-mentioned other agricultural chemicals include, for example, mepanipyrim, pyrimethanil, cyprodinil 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, metconazole, ep
  • 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 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-based compounds such as pyraclostrobin, fluoxastrobin, fluacrypyrin;
  • 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 present invention is effective for controlling fleas belonging to the family Flea, particularly 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 present invention 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 present invention When used as an animal parasite control agent, it may be used as it is. In addition, it can be used in the form of various forms such as powders, granules, tablets, powders, capsules, liquids, emulsions, aqueous suspensions, oily suspensions and the like together with appropriate auxiliary agents. 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. Examples of the adjuvant used in the preparation 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 of the compound of the present invention 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 the present invention 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 the present invention.
  • the compound of the present invention is prepared into an appropriate preparation and then taken into the body by intravenous administration, intramuscular administration, intradermal administration, subcutaneous administration, etc .; spot-on For example, a method of administering to the body surface by treatment, pour-on treatment, spray treatment, etc .; a method of embedding a resin piece containing the compound of the present invention under the skin of a host animal, and the like.
  • the dose of the compound of the present invention to the host animal varies depending on the administration method, administration purpose, disease symptoms, etc., but is usually a ratio of 0.01 mg to 100 g, preferably 0.1 mg to 10 g, per 1 kg body weight of the host animal. Is suitable for administration.
  • 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 parasitic animal diseases containing the compound of the present invention as an active ingredient, and a method for preventing or treating parasitic 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.
  • X is alkyl, alkenyl, alkynyl, aryl, halogen atom, haloalkyl, cyano, nitro, NR 4 R 5 , S (O) n R 3 , OR 2 , COR 2 or COOR 2 A is a halogen atom, OR 2 , S (O) n R 3 , OS (O) n R 3 ,
  • R 1 is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen atom, substituted with alkyl
  • An optionally heterocyclic group CH ⁇ NOR 2 , CH ⁇ NNR 4 R 5 , COR 2 , COOR 2 , OR 2 , S (O) n R 3 , NR 4 R 5 or CONR 4 R 5 ; Alkyl, aryl, halogen atom, haloalkyl or OR 2 ;
  • A is a halogen atom, OR 2 , S (O) n R 3 , OS (O) n R 3 , NR 4 R 5 , alkyl, cycloalkyl, heterocycle A group, NHNR 4 R 5 , COOR 2 or nitro;
  • R 2 is a hydrogen atom, alkyl, haloalkyl or cyanoalkyl;
  • R 3
  • A is OR 2 , S (O) n R 3 , OS (O) n R 3 , NR 4 R 5 or nitro;
  • R 5 is haloalkyl, COR
  • (5) The pyridyl-triazolopyrimidine derivative or a salt thereof according to (1), wherein X is OR 2 .
  • Synthesis example 1 Synthesis of 7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] -5-formyl [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 18)
  • 2-acetyl-3-chloro-5- (trifluoromethyl) pyridine 1.0 g
  • N, N-dimethylacetamide dimethylacetal 715 mg
  • Synthesis example 3 Synthesis of 7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] -5-dimethoxymethyl [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 7) 7 -[3-Chloro-5- (trifluoromethyl) pyridin-2-yl] -5-formyl [1,2,4] triazolo [1,5-a] pyrimidine in a mixed solution of 220 mg and methanol Paratoluenesulfonic acid was added and heated to reflux for 7 hours.
  • the mixture was neutralized by adding a saturated aqueous sodium hydrogen carbonate solution, extracted twice with ethyl acetate, the organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate.
  • Synthesis example 4 Synthesis of 7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] -5-hydroxymethyl [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 36) 7 A mixed solution of 710 mg of [3-chloro-5- (trifluoromethyl) pyridin-2-yl] -5-formyl [1,2,4] triazolo [1,5-a] pyrimidine and 10 ml of methanol was ice-cooled. 164 mg of sodium borohydride was added and stirred for 30 minutes.
  • Synthesis example 5 7- [3-Chloro-5- (trifluoromethyl) pyridin-2-yl] -5-methanesulfonyloxymethyl [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 51)
  • Synthesis 7- [3-Chloro-5- (trifluoromethyl) pyridin-2-yl] -5-hydroxymethyl [1,2,4] triazolo [1,5-a] pyrimidine 136 mg, triethylamine 0.23 ml and chloroform 5 ml of the mixed solution was ice-cooled, 0.05 ml of methanesulfonyl chloride was added, and the mixture was stirred for 1 hour under ice-cooling.
  • Synthesis example 7 7- [3-Chloro-5- (trifluoromethyl) pyridin-2-yl] -5- (oxiran-2-yl) [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 1) 21) Synthesis 7- [3-Chloro-5- (trifluoromethyl) pyridin-2-yl] -5-formyl [1,2,4] triazolo [1,5-a] pyrimidine 200 mg, trimethyl sulfoiodide 110 mg of potassium tert-butoxide was added to a mixed solution of 215 mg of xsonium and 5 ml of dimethyl sulfoxide, and stirred at room temperature for 20 hours.
  • Synthesis example 8 Synthesis of 7- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] [1,2,4] triazolo [1,5-a] pyrimidine-5-carboxylic acid (Compound No. 48) 7 A mixed solution of 1.0 g of 10- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] -5-formyl [1,2,4] triazolo [1,5-a] pyrimidine and 10 ml of acetone was added to ice. After cooling, 3 ml of Jones reagent was slowly added dropwise, and the mixture was stirred for 1 hour under ice cooling.
  • the reaction solution was returned to room temperature, and the precipitated solid was filtered to obtain a filtrate containing 2-fluoro-3-iodo-5- (trifluoromethyl) pyridine.
  • a filtrate containing 2-fluoro-3-iodo-5- (trifluoromethyl) pyridine.
  • 22.3 g of sodium cyanide and 6.7 g of tetrabutylammonium bromide were added and stirred at 50 ° C. for 6 hours.
  • the reaction solution was poured into 4,000 ml of water, and the precipitated solid was filtered.
  • reaction mixture was acidified with 1N hydrochloric acid, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to remove crude 1-cyclopropyl-3- [ 3-Iodo-5- (trifluoromethyl) pyridin-2-yl] propane-1,3-dione was obtained as a liquid.
  • 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 the radish leaves, the parasitic radish leaves were immersed in a chemical solution adjusted to a concentration of 200 ppm of the present compound 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.
  • Death rate (%) (1 ⁇ (number of surviving insects / number of treated insects)) ⁇ 100
  • Test Example 2 Effect test on green planthopper Rice seedlings were immersed in a chemical solution adjusted to have a concentration of the present compound of 200 ppm for about 10 seconds. 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 No.
  • Test Example 3 Effect test on silver leaf whitefly A potted cucumber seedling infested with silver leaf whitefly 1-2 larvae was sprayed with a chemical solution adjusted to a concentration of 200 ppm of the compound of the present invention using a hand spray. 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. Compound No.
  • 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 the present invention.
  • about 50 young mites were collected from the ear of the dog. Let go through and 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 the present invention drops or kills the parasitic spider mite.
  • Test Example 5 Medicinal Efficacy Test Using a Dog against a Cat Flea A gelatin capsule containing 10 mg / kg body weight of the compound of the present invention was administered to a dog (beagle, 8 months old), and immediately after that about 100 cat flea non-blood-sucking adults were covered in the back Let go on and let it infest. The compound of the present invention exhibits a hatching-inhibiting effect on the treated eggs of treated adults. Test Example 5 Drug efficacy test using dogs against cat fleas
  • Formulation Example 1 (1) Compound of the present invention 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 alkylnaphthalene sulfonate 2 parts by weight or more To make a wettable powder.
  • Formulation Example 2 (1) Compound of the present invention 5 parts by weight (2) Talc 60 parts by weight (3) Calcium carbonate 34.5 parts by weight (4) Liquid paraffin 0.5 parts by weight or more are uniformly mixed to obtain a powder.
  • Formulation Example 3 (1) Compound of the present invention 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 A mixture of more than parts by weight is uniformly mixed and dissolved to obtain 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 the present compound Mix at a weight ratio of 4: 1 to make a wettable powder.
  • Formulation Example 5 (1) Compound of the present invention 50 parts by weight (2) Sodium alkylnaphthalene sulfonate formaldehyde condensate 2 parts by weight (3) Silicone oil 0.2 parts by weight (4) Water 47.8 parts by weight or more uniformly mixed (5) 5 parts by weight of sodium polycarboxylate (6) 42.8 parts by weight of anhydrous sodium sulfate are further added to the crushed stock solution, and the mixture is uniformly mixed, granulated and dried to obtain a granulated wettable powder.
  • Formulation Example 6 (1) Compound of the present invention 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 (1 ) To (3) are mixed uniformly in advance and diluted with an appropriate amount of acetone, and then sprayed onto (4) to remove acetone and form granules.
  • Formulation Example 7 (1) Compound of the present invention 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 give a trace amount of spray ( ultra low volume formulation).
  • Formulation Example 8 (1) Compound of the present invention 40 parts by weight (2) Polyoxyethylene tristyryl phenyl ether potassium phosphate 4 parts by weight (3) Silicone oil 0.2 part by weight (4) Xanthan gum 0.1 part by weight (5) Ethylene glycol 5 Part by weight (6) Water 50.7 parts by weight or more are uniformly mixed and pulverized to obtain an aqueous suspension.
  • Formulation Example 9 (1) Compound of the present invention 10 parts by weight (2) 80 parts by weight of diethylene glycol monoethyl ether (3) Polyoxyethylene alkyl ether 10 parts by weight or more of ingredients are mixed uniformly to obtain an aqueous solution.
  • novel pyridyl-triazolopyrimidine derivatives or salts thereof of the present invention are useful as pest control agents.
  • the entire contents of the specification, claims, and abstract of Japanese Patent Application No. 2008-208708, filed on August 13, 2008, are incorporated herein as the disclosure of the specification of the present invention. Is.

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

Abstract

La présente invention concerne un nouvel agent de lutte contre les organismes nocifs. L'agent de lutte contre les organismes nocifs comprend un dérivé pyridyl-triazolopyrimidine représenté par la formule (I) [dans laquelle R1 représente un alkyle éventuellement substitué, un cycloalkyle éventuellement substitué, un alcényle éventuellement substitué, un alcynyle éventuellement substitué, un atome d'halogène, un cyano, un aryle, un groupe hétérocyclique éventuellement substitué par un alkyle, CH=NOR2, CH=NNR4R5, COR2, COOR2, OR2, S(O)nR3, NR4R5 ou CONR4R5 ; X représente un alkyle, un alcényle, un alcynyle, un aryle, un groupe hétérocyclique, un atome d'halogène, un halogénoalkyle, un cyano, un nitro, NR4R5, CONR4R5, S(O)nR3, OR2, COR2 ou COOR2 ; m représente un entier de 1 à 4 ; et n représente un entier de 0 à 2] ou un sel de celui-ci comme principe actif.
PCT/JP2009/064275 2008-08-13 2009-08-12 Dérivé pyridyle-triazolopyrimidine ou sel de celui-ci, et agent de lutte contre les organismes nocifs le comprenant Ceased WO2010018853A1 (fr)

Applications Claiming Priority (2)

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JP2008208708 2008-08-13
JP2008-208708 2008-08-13

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WO2010018853A1 true WO2010018853A1 (fr) 2010-02-18

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Publication number Priority date Publication date Assignee Title
CN106905231A (zh) * 2015-12-23 2017-06-30 联化科技股份有限公司 3-氯-5-三氟甲基吡啶类化合物及中间体的制备方法
US10287286B2 (en) 2015-03-18 2019-05-14 Takeda Pharmaceutical Company Limited Compounds
CN115427411A (zh) * 2020-02-18 2022-12-02 Pi工业有限公司 作为农作物保护用杀虫剂的5-(3-(乙基磺酰基)吡啶-2-基)-吡唑并[1,5-a]嘧啶衍生物及相关化合物

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JPS4835456B1 (fr) * 1970-12-28 1973-10-27
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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
WO2004082383A1 (fr) * 2003-03-17 2004-09-30 Basf Aktiengesellschaft Utilisation de triazolopyrimidines pour combattre les nematodoses de vegetaux
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
WO2008099902A1 (fr) * 2007-02-15 2008-08-21 Ishihara Sangyo Kaisha, Ltd. Dérivé de pyridyl-triazolopyrimidine ou son sel, pesticide la contenant et son procédé de production

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JPS4835456B1 (fr) * 1970-12-28 1973-10-27
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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
WO2004082383A1 (fr) * 2003-03-17 2004-09-30 Basf Aktiengesellschaft Utilisation de triazolopyrimidines pour combattre les nematodoses de vegetaux
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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 (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10287286B2 (en) 2015-03-18 2019-05-14 Takeda Pharmaceutical Company Limited Compounds
CN106905231A (zh) * 2015-12-23 2017-06-30 联化科技股份有限公司 3-氯-5-三氟甲基吡啶类化合物及中间体的制备方法
CN115427411A (zh) * 2020-02-18 2022-12-02 Pi工业有限公司 作为农作物保护用杀虫剂的5-(3-(乙基磺酰基)吡啶-2-基)-吡唑并[1,5-a]嘧啶衍生物及相关化合物
EP4107159B1 (fr) 2020-02-18 2024-04-17 PI Industries Ltd. Dérivés de 5-(3-(éthylsulfonyl)pyridin-2-yl)-pyrazolo[1,5-a]pyrimidine et composés similaires en tant qu'agents pésticides et insecticides pour la protection de cultures
CN115427411B (zh) * 2020-02-18 2025-09-02 Pi工业有限公司 稠合杂环化合物及其作为害虫防治剂的用途

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