WO2000037460A1 - Composes de 5-azolylpyrimidine, procede de preparation de ces composes et germicides a usage agricole et horticole - Google Patents

Composes de 5-azolylpyrimidine, procede de preparation de ces composes et germicides a usage agricole et horticole Download PDF

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Publication number
WO2000037460A1
WO2000037460A1 PCT/JP1999/007204 JP9907204W WO0037460A1 WO 2000037460 A1 WO2000037460 A1 WO 2000037460A1 JP 9907204 W JP9907204 W JP 9907204W WO 0037460 A1 WO0037460 A1 WO 0037460A1
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carbon atoms
group
atom
formula
compound
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PCT/JP1999/007204
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English (en)
Japanese (ja)
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Toshinobu Tanaka
Yoshinori Yamanaka
Shuji Yokoyama
Takehiko Asahara
Motoki Yuguchi
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Ube Industries, Ltd.
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Publication of WO2000037460A1 publication Critical patent/WO2000037460A1/fr

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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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • 5-Azolylpyrimidine compounds their preparation and fungicides for agricultural and horticultural use
  • the present invention relates to a novel 5-azolylpyrimidine compound useful as a fungicide for agricultural and horticultural use.
  • the 1-position of this derivative is fixed to an amino group and a thiol group, and no disclosure of a 5-azolylpyrimidine compound having a substituent introduced therein as in the present invention is found. Therefore, the 5-azolylpyrimidine compound of the present invention is a novel compound and has not been known to have a fungicidal activity for agricultural and horticultural purposes.
  • An object of the present invention is to provide a novel 5-azolylpyrimidine compound, a method for producing the same, and a fungicide for agricultural and horticultural use containing the same as an active ingredient. Disclosure of the invention
  • the present inventors have conducted studies to solve the above problems, and as a result, have found that a novel 5-azolyl bilimidine compound has remarkable bactericidal activity for agricultural and horticultural use, and have completed the present invention.
  • the present invention is as follows.
  • R 1 is SO m R 4 , a hydrogen atom, a halogen atom, a haloalkyl group having 16 carbon atoms, a haloalkoxy group having 16 carbon atoms, a cycloalkoxy group having 36 carbon atoms, Alkenyloxy group having 39 carbon atoms, alkynyloxy group having 39 carbon atoms, 0- (CH 2 ) n -R6, alkyl group having 16 carbon atoms or carbon atom having 1 20
  • R 4 represents an alkyl group having 16 carbon atoms or a pyridyl group;
  • R 6 represents a phenyl group, a phenoxy group, or a carbon atom which may have a substituent; 1 6 alkoxy group, a S i (CH 3) 3, CN, NO 2 , or N (R 7) R8; 1 ⁇ 7 and 8 represent a hydrogen atom, C 1 6 alkyl group having a
  • the present invention relates to a 5-azolylpyrimidine compound represented by the formula:
  • the second invention (synthesis method 1)
  • R 2 , 1 ⁇ 4 and ⁇ are as defined above.
  • R 3 is an alkoxy group having 1 to 20 carbon atoms, SO m R 5 or 0- (CH 2 ) n -R 6
  • the present invention relates to a method for producing a 5-azolylpyrimidine compound represented by the formula:
  • the third finding (synthesis method 2) is that
  • the fourth invention (synthesis method 3)
  • n ′ represents 0 or 1;
  • R 9 is SO m R 4, a hydrogen atom, a halogen atom, a haloalkyl group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms.
  • R 6 represents an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 20 carbon atoms;
  • R 2, R 5 and Y are as defined above,
  • R 10 in one XH (6) formula X is S or 0;
  • R 1 0 is a carbon atom number of 1-6 or a haloalkyl group, a cycloalkyl group having 3 to 6 carbon atoms, 3 carbon atoms Represents an alkenyl group of 9 to 9 carbon atoms, an alkynyl group of 3 to 9 carbon atoms,-(CH 2 ) n -R 6 or an alkyl group of 1 to 20 carbon atoms,
  • W represents a halogen atom
  • R 2 , 1-9 and ⁇ are as defined above.
  • the sixth kakimaki relates to a fungicide for agricultural and horticultural use containing the 5-azolylpyrimidine compound represented by the above formula (1) as an active ingredient.
  • R 1 is SO m R 4 , a hydrogen atom, a halogen atom, a haloalkyl group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, a cycloalkoxy having 3 to 6 carbon atoms.
  • Group, alkenyloxy group having 3-9 carbon atoms, alkynyloxy group having 3-9 carbon atoms, ⁇ - (CH 2 ) n -R 6 , alkyl group having 1-6 carbon atoms, carbon atom number 1 to 20 alkoxy groups can be mentioned.
  • alkyl group examples include a linear or branched alkyl group; preferably an alkyl group having 1 to 4 carbon atoms; and more preferably an alkyl group having 1 to 3 carbon atoms. It is.
  • alkyl group having 1 to 6 carbon atoms examples include linear or branched ones; preferably 1 to 3 carbon atoms; and more preferably 1 to 3 carbon atoms; , it is CH 3.
  • alkoxy group having 1 to 20 carbon atoms examples include straight-chain or branched ones; preferably, the alkoxy group has 1 to 3 carbon atoms; Preferably, it is OCH 3 , ⁇ C 3 H 7 — n, ⁇ C 3 H 7 -iso.
  • halogen atom examples include a chlorine atom, an iodine atom, a bromine atom and a fluorine atom; preferably, a chlorine atom and a fluorine atom.
  • haloalkyl group examples include straight-chain or branched ones; preferably, it has 1 to 6 carbon atoms; more preferably, CF 3.
  • haloalkoxy group examples include linear or branched ones; preferably those having 1 to 6 carbon atoms; and more preferably OCH 2 CF 3 It is.
  • the cycloalkoxy group preferably has 3 to 6 carbon atoms; more preferably, cyclopropoxy.
  • alkenyloxy group examples include linear or branched ones; preferably those having 3 to 9 carbon atoms; and more preferably Roxy.
  • alkynyloxy group examples include linear or branched ones; preferably those having 3 to 9 carbon atoms; and more preferably propynyloxy.
  • R 6 (10) 0- (CH 2 ) n —
  • n is an integer of 1 to 4
  • R 6 is a phenyl group which may have a substituent, a phenoxy group, a carbon atom number of 1 to 6 alkoxy, S i (CH 3) 3 , CN, N0 2, N (R 7) can be exemplified R 8.
  • Examples of the substituent for the phenyl group and the phenoxy group include a halogen atom.o
  • substitution at the 4-position is preferred.
  • substituted halogen atom examples include a chlorine atom, an iodine atom, a bromine atom, a fluorine atom and the like; preferably, a chlorine atom and a fluorine atom.
  • Alkoxy groups include linear or branched ones; preferably those having 1 to 4 carbon atoms; and more preferably those having 1 to 3 carbon atoms. belongs to.
  • R 8 , 1 ⁇ 7 and 1 ⁇ 8 can be a hydrogen atom, a linear or branched alkyl group, preferably having 1 to 6 carbon atoms. And more preferably CH 3 .
  • R 2 examples include a phenyl group, a phenoxy group and a naphthyl group.
  • phenyl, phenoxy or naphthyl group examples include substituted or unsubstituted ones.
  • Examples of the substituent include a halogen atom, CN, NO ⁇ , an alkyl group having 1 to 6 carbon atoms, Examples thereof include an alkoxy group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, and a haloalkoxy group having 1 to 6 carbon atoms.
  • halogen atom examples include a halogen atom such as a chlorine atom, an iodine atom, a bromine atom, and a fluorine atom; preferably, a chlorine atom.
  • the position of the substitution is not particularly limited, but substitution at the 2-, Z- or 4-position is preferred.
  • Examples of the alkyl group having 1 to 6 carbon atoms include linear or branched ones; preferably 1 to 3 carbon atoms; and more preferably CH 3 It is.
  • the position of the substitution is not particularly limited, but substitution at the 4-position is preferable.
  • Examples of the alkoxy group having 1 to 6 carbon atoms include linear or branched ones; preferably 1 to 3 carbon atoms; and more preferably OCH 3
  • the position of the substitution is not particularly limited, but substitution at the 4-position is preferable.
  • Examples of the haloalkyl group having 1 to 6 carbon atoms include linear or branched ones; preferably 1 to 3 carbon atoms; and more preferably CF 3 It is.
  • the substitution position is not particularly limited, but the 4-position substitution is preferred.
  • haloalkoxy group having 1 to 6 carbon atoms examples include straight-chain or branched ones; preferably having 1 to 3 carbon atoms; more preferably Is OCF 3 .
  • the position of the substitution is not particularly limited, but substitution at the 4-position is preferable.
  • alkoxy group having 1 to 20 carbon atoms examples include a linear or branched alkoxy group; preferably, the alkoxy group has 1 to 6 carbon atoms; is favored properly, OCH 3, OC 2 H 5 , OC 3 H 7 -n, OC 4 H 9 - n, OC 6 H 1 3 - n, ⁇ _C 20 H 4 i - a n.
  • m is an integer from 0 to 2; the R5, mention may be made 1-6 alkyl group carbon atoms.
  • alkyl group examples include a linear or branched one; Has 1 to 4 carbon atoms; more preferably CH 3 and C 2 H 5 . '
  • n is an integer of 1-4;
  • R 6 is a phenyl group, a phenoxy group, an alkoxy group, S i (CH 3 ) 3, CN, N ⁇ 2 , N (R7) R8.
  • n is preferably 2 when R 6 is a phenyl group, a phenoxy group, an alkoxy group, N 0 2 , N (R 7) R 8 and CN; and 3 when S 6 is S i (CH 3 ) 3. It is.
  • Examples of the phenyl group and the phenoxy group include substituted and unsubstituted ones.
  • substituents examples include a halogen atom such as a chlorine atom, an iodine atom, a bromine atom, and a fluorine atom; preferably, a chlorine atom.
  • a halogen atom such as a chlorine atom, an iodine atom, a bromine atom, and a fluorine atom; preferably, a chlorine atom.
  • the position of the substitution is not particularly limited, but substitution at the 4-position is preferable.
  • Alkoxy groups include straight-chain or branched ones; preferably they have 1 to 4 carbon atoms; and more preferably 1 to 3 carbon atoms. belongs to.
  • N (R7) R 8, 1 ⁇ 7 ⁇ Pi 1 ⁇ 8 is a hydrogen atom, a linear or can be given branched alkylene Le groups but, preferably, the number is 1-6 carbon atoms And more preferably CH 3 .
  • halogen atom examples include a chlorine atom, an iodine atom, a bromine atom and a fluorine atom; preferably, a chlorine atom.
  • haloalkoxy groups having 1 to 6 carbon atoms include straight-chain or branched alkoxy groups having a halogen atom such as a chlorine atom, an iodine atom, a bromine atom and a fluorine atom as a substituent. But preferably has 1 to 4 carbon atoms; more preferably OCH 2 CF 3 .
  • Examples of the alkynyloxy group having 3 to 9 carbon atoms include straight-chain or branched ones; preferably, the alkynyloxy group has 3 to 5 carbon atoms; Preferably, OCH 2 C ⁇ CH.
  • the cycloalkoxy group preferably has 3 to 6 carbon atoms; more preferably, cyclopropoxy. ⁇
  • Examples of Y include CH and N.
  • Examples of the compound (1) include compounds obtained by combining the above-mentioned various substituents.
  • Preferred compounds from the viewpoint of drug efficacy are as follows.
  • a compound wherein 1 ⁇ 1 is 50 111 1 ⁇ 4, R 2 is a phenyl group, 1 ⁇ 3 is an alkoxy group having 1 to 12 carbon atoms, and Y is CH.
  • R 1 is a hydrogen atom
  • R 2 is a phenyl group
  • R 3 is an alkoxy group having ⁇ to ⁇ 2 carbon atoms
  • Y is CH.
  • R 1 is an alkyl group having 1 to 6 carbon atoms
  • R 2 is a phenyl group
  • 1 ⁇ 3 is 30 111 1 ⁇ 5
  • Y is CH.
  • R 1 is SO m R 4
  • R2 is a phenyl group
  • R3 is S_ ⁇ ra R 5
  • R 1 is an alkoxy group having 1 to 6 carbon atoms
  • R 2 is a phenyl group
  • 3 is an alkoxy group having 1 to 12 carbon atoms
  • Y is CH.
  • R 1 is an alkoxy group having 1 to 6 carbon atoms
  • R 2 is a phenyl group
  • R 3 is a hydrogen atom
  • Y is CH.
  • R 1 is a hydrogen atom
  • R 2 is a phenyl group
  • R 3 is an alkynyloxy group having 3 to 9 carbon atoms
  • Y is CH.
  • R 1 is a hydrogen atom
  • R 2 is a phenyl group
  • 1 ⁇ 3 is 50 111 1 ⁇ 5
  • R 1 is a hydrogen atom
  • R 2 is a phenyl group
  • R 3 is an alkynyloxy group having 3 to 9 carbon atoms
  • Y is N.
  • R 1 is S_ ⁇ m R 4
  • R2 is a phenyl group
  • R3 is located at S_ ⁇ m R5
  • Y is N.
  • Preferred methods for producing compound (1) include the following two methods (Synthesis methods 5 and 5) in addition to Synthetic methods 1, 2, 3 and 4 described as the second, third, fourth and fifth kaki. 6) can be listed.
  • R 2 , R 9 and Y are as defined above,
  • a method for producing a compound (7) represented by the above formula (7) comprising reacting the compound represented by the formula (1) with a halogenating agent without using a solvent or in the presence of a base.
  • a method for producing a compound (8) represented by the above formula (8) comprising reacting the compound (7) with a hydroxide of an alkali metal in a solvent.
  • Synthesis method 1 is a method in which compound (1) is obtained by reacting compound (2) with compound (3) in a solvent in the presence of a base.
  • the type of the solvent is not particularly limited as long as it does not directly participate in the reaction, and examples thereof include benzene, toluene, xylene, methylnaphthalene, petroleum ether, rigoin, hexane, chlorobenzene, dichlorobenzene, Chlorinated or unchlorinated aromatic, aliphatic and cycloaliphatic hydrocarbons such as formaldehyde, dichloroethane, trichloroethylene; ethers such as getyl ether, tetrahydrofuran, dioxane, etc.
  • Alcohols such as methanol, ethanol, ethylene glycol and the like; Aprotic polar solvents such as N, N-dimethylformamide, dimethylsulphoxide, N, N-dimethylimidazolidinone, N-methylpyrrolidone; and mixtures of the above solvents.
  • the amount of the solvent to be used, the compound (2) can be used as becomes 5-8 0% by weight; 1 0-7 0 weight 0/0 are preferred.
  • the reaction temperature is not particularly limited, but is in the range of from room temperature to the boiling point of the solvent used or less; 10 to L 10 ° C is preferable.
  • the type of base is not particularly limited, and organic and inorganic bases, for example, organic bases such as triethylamine, pyridine, 4- (N, N-dimethylamino) pyridine, N, N-dimethylaniline, DBU; sodium methoxide, Alkali metal alkoxides such as potassium-t-butoxide; and inorganic bases such as hydroxides, hydrides, carbonates, and hydrogencarbonates of alkali metal and alkaline earth metal. it can.
  • organic bases such as triethylamine, pyridine, 4- (N, N-dimethylamino) pyridine, N, N-dimethylaniline, DBU; sodium methoxide, Alkali metal alkoxides such as potassium-t-butoxide
  • inorganic bases such as hydroxides, hydrides, carbonates, and hydrogencarbonates of alkali metal and alkaline earth metal. it can.
  • the amount of the base to be used is 1 to 5 moles relative to compound (2); preferably 2 to 3.5 moles.
  • the reaction temperature is not particularly limited, but is in the range of room temperature to the boiling point of the solvent used or lower;
  • reaction time varies depending on the concentration and temperature in the previous period; it is usually 0.5 to 7 hours.
  • Compound (3) is used in an amount of 1.0 to 5 moles, preferably 1.0 to 3 moles, based on Compound (2).
  • the compound (2) used in the present invention is produced according to the method described in Tetrahedron. Lett., 1973, 30 (372), p. 420. Can o
  • the target compound (1) produced as described above is subjected to ordinary post-treatments such as extraction, concentration and filtration, and if necessary, recrystallization, various chromatography and other known means. And can be appropriately refined.
  • Synthesis method 2 is a method of reacting compound (4) with compound (3) in a solvent in the presence of a base to obtain compound (1).
  • solvent examples include ethers described in Synthesis Method 1, chlorinated or unaromatic aromatic, aliphatic, alicyclic hydrocarbons, alcohols, aprotic polar solvents, and And mixtures of the above-mentioned solvents.
  • the reaction temperature is not particularly limited, but is in the temperature range from room temperature to the boiling point of the solvent used or less; preferably from 10 to 110 "C.
  • the reaction time varies depending on the concentration and temperature in the previous period; it is usually 0.5 to 5 hours.
  • the compound (3) is used in an amount of 1.0 to 5 times the molar amount of the compound (4); the amount of the starting compound used is preferably 1.0 to 3 times the molar amount.
  • Compound (4) can be produced by the method described in Journal of the American Chemical Society, 1980, Vol. 102, page 2838.
  • the target compound (1) produced as described above is subjected to ordinary post-treatments such as extraction, concentration, filtration, and the like, and if necessary, known means such as recrystallization and various types of chromatography. And can be appropriately refined.
  • Synthesis method 2 is a method in which compound (5) and compound (6) are reacted in a solvent in the presence of a base to obtain compound (1).
  • Examples of the type of the solvent include the ethers described in Synthesis Method 1, chlorinated or unaromatic aromatic, aliphatic, alicyclic hydrocarbons, alcohols, aprotic polar solvents, and the above. Mixtures of solvents can be mentioned.
  • the amount of the solvent to be used, the compound (5) can be used in such a manner that 5 to 80 wt%; 1 0-70 weight 0/0 are preferred.
  • the reaction temperature is not particularly limited, but is in a temperature range from room temperature to the boiling point of the solvent used or lower; preferably from 10 to 110.
  • the reaction time varies depending on the concentration and temperature in the previous period; it is usually 0.5 to 5 hours.
  • the compound (3) is used in an amount of 1.0 to 10 times the amount of the compound (5); the amount of the starting compound used is preferably 1.0 to 8 times.
  • As the compound (6) a commercially available product can be used.
  • the target compound (1) produced as described above is subjected to ordinary post-treatments such as extraction, concentration, filtration, and the like, and if necessary, known means such as recrystallization and various types of chromatography. And can be appropriately refined.
  • Synthetic method 4 is a method of obtaining compound (1) by reacting compound (7) with compound (6) in a solvent in the presence of a base.
  • Examples of the type of the solvent include those described in Synthesis Method 1 and water.
  • the solvent can be used in such an amount that the compound (7) is 5-80% by weight; however, it is preferably 10-70% by weight.
  • the type of base is not particularly limited, and organic and inorganic bases, for example, organic bases such as triethylamine, pyridine, 4- (N, N-dimethylamino) pyridine, N, N-dimethylaniline, DBU; sodium methoxide, Alkali metal alkoxides such as potassium-t-ptide and the like; inorganic bases such as hydroxides, hydrides, carbonates and hydrogencarbonates of alkali metal and alkaline earth metal can be mentioned. .
  • organic bases such as triethylamine, pyridine, 4- (N, N-dimethylamino) pyridine, N, N-dimethylaniline, DBU; sodium methoxide, Alkali metal alkoxides such as potassium-t-ptide and the like
  • inorganic bases such as hydroxides, hydrides, carbonates and hydrogencarbonates of alkali metal and alkaline earth metal can be mentioned. .
  • the amount of the base to be used is 1 to 5 moles compared to Compound (7); preferably, it is 1.2 to 2.0 moles.
  • the reaction temperature is not particularly limited, but is in the range of 100 ° C. to a temperature not higher than the boiling point of the solvent used; ⁇ 80 to ⁇ 10 ° C. is preferable.
  • the reaction time varies depending on the concentration and temperature in the previous period; it is usually 0.5 to 5 hours.
  • the amount of the starting compound used is 1.0 to 5 times the molar amount of the compound (6) relative to the compound (7); preferably 1.0 to 3 times the molar amount.
  • Compound (7) can be produced by (Synthesis method 5).
  • the target compound (1) produced as described above is subjected to usual post-treatments such as extraction, concentration, and filtration, and if necessary, recrystallization, various chromatographic methods, and other known means. And can be appropriately refined.
  • Synthesis method 5 is a method for obtaining compound (7) by reacting compound (8) with a halogenating agent in the absence of a solvent or in the presence of a base.
  • halogenating agent examples include chlorinating agents such as oxychloride phosphorus, a mixture of oxychloride quinoline and pentachloroaniline, phosphorus oxybromide, and a mixture of phosphorus oxybromide and phosphorus tribromide.
  • chlorinating agents such as oxychloride phosphorus, a mixture of oxychloride quinoline and pentachloroaniline, phosphorus oxybromide, and a mixture of phosphorus oxybromide and phosphorus tribromide.
  • Brominating agents can be mentioned.
  • the amount of the halogenating agent to be used is about 10-fold the molar amount of compound (8)], but preferably about 1- to 2-fold the molar quantity.
  • Examples of the type of the base include tertiary amines such as diisopropylethylamine, dimethylaniline and getylaniline.
  • the amount of the base to be used is 1 to 10 moles relative to compound (8); preferably, it is 1.2 to 10 moles.
  • the reaction temperature is not particularly limited, but is in the range of room temperature to the boiling point of the solvent to be used or lower; preferably from room temperature to 150 ° C.
  • reaction time varies depending on the concentration and temperature in the previous period; it is usually 0.5 to 5 hours.
  • Compound (8) can be produced by synthetic method (6).
  • the target compound (7) produced as described above is subjected to ordinary post-treatments such as extraction, concentration, and filtration, and if necessary, known means such as recrystallization and various types of chromatography. And can be appropriately refined.
  • the synthesis method (6) is a method for obtaining the compound (8) according to the synthesis method (5) by reacting the compound (7) with a hydroxide of an alkali metal in a solvent.
  • alkali metal hydroxides examples include sodium hydroxide and potassium hydroxide.
  • the amount of the alkali metal hydroxide to be used is 1 to 10 moles relative to compound (7); preferably 1 to 3 moles.
  • Examples of the type of the solvent include the solvent and water described in Synthesis Method 1, a mixture of these solvents, and the like.
  • the amount of the solvent to be used may be such that the amount of the compound (7) is 5 to 80% by weight; however, it is preferably 10 to 70% by weight.
  • the reaction temperature is not particularly limited, but is in the range of from 20 to the boiling point of the solvent to be used; it is preferably from 110 to 100 ° C.
  • the reaction time varies depending on the concentration and temperature described above; it is usually 1.6 to 5 hours.
  • the target compound (8) produced as described above is subjected to ordinary post-treatments such as extraction, concentration, and filtration, and if necessary, recrystallization, various chromatography, and other known means. And can be appropriately refined.
  • Examples of the compound (1) include compounds 1 to 71 shown in Table 1 below.
  • Examples of the pathogenic bacteria for agricultural and horticultural use which are effective in controlling the compound (1) of the present invention include wheat rust, barley powdery mildew, wheat powdery mildew, cucumber powdery mildew, cucumber gray mold, cucumber and cucumber bacterium. , Rice blast fungus and tomato late blight fungus.
  • the agricultural and horticultural fungicide of the present invention contains at least one compound (1) as an active ingredient.
  • Compound (1) depending also can force 5 , usually conventional methods can be used alone, carrier, interfacial active agents, dispersing agents, adjuvants, formulation and the like (e.g., powders, emulsions, microgranules, granules Agents, wettable powders, oily suspensions, aerosols and the like).
  • carrier usually conventional methods can be used alone, carrier, interfacial active agents, dispersing agents, adjuvants, formulation and the like (e.g., powders, emulsions, microgranules, granules Agents, wettable powders, oily suspensions, aerosols and the like).
  • Carriers include, for example, solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, bamboo silicate, bamboo silicate, bamboo sand, ammonium sulfate, urea, etc .; hydrocarbons (kerosene, mineral oil, etc.), aromatics Group hydrocarbons (benzene, toluene, xylene, etc.), chlorinated hydrocarbons (chloroform, carbon tetrachloride, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, cyclohexanone, isophorone, etc.) , Esters (ethyl acetate, ethylene glycol acetate, dibutyl maleate, etc.), alcohols (methanol, n-hexanol, ethylene glycol, etc.), polar solvents (dimethylformamide, dimethyl sulfoxide, etc.), liquids such as
  • surfactants and dispersants that can be used to improve the performance of this agent, such as adhesion to animals and plants, improved absorption, and dispersion, emulsification, and spreading of drugs, include, for example, alcohol sulfate esters, alkyls Sulfonates, ligninsulfonates, polyoxyethylene glycol ethers and the like can be mentioned.
  • alcohol sulfate esters alkyls Sulfonates
  • ligninsulfonates polyoxyethylene glycol ethers and the like
  • polyoxyethylene glycol ethers and the like can be mentioned.
  • carboxymethylcellulose, polyethylene glycol, gum arabic and the like can be used as adjuvants.
  • the above-mentioned carrier, surfactant, dispersant and auxiliary agent can be used alone or in an appropriate combination, respectively, according to the respective purposes.
  • the concentration of the active ingredient is usually from 1 to 50 in an emulsion.
  • % For powders, usually 0.3 to 25% by weight, for wettable powders, usually 1 to 90% by weight 6, for granules, usually 0.5 to 5% by weight 96, for oils, usually 0.5 to 5% by weight, the aerosol is usually from 0.1 to 5 weight 0/0.
  • reaction solution was extracted twice with 30 ml of ethyl acetate, and the combined organic layers were washed with brine, dried over sodium sulfate, and evaporated under reduced pressure.
  • reaction solution was extracted twice with 30 ml of ethyl acetate, and the combined organic layers were washed with brine, dried over sodium sulfate, and evaporated under reduced pressure.
  • Table 1 shows the compounds (1) synthesized as described above and their physical properties.
  • toxanone (trade name; manufactured by Sanyo Chemical Industry Co., Ltd.) was added, mixed uniformly, and dissolved to obtain an emulsion.
  • Compound (1) was uniformly mixed with 5 parts by weight of powder, 50 parts by weight of talc, and 45 parts by weight of kaolin to obtain a powder.
  • Pyricularia oryzae partial resistance spore suspension (3 X 1 0 5 spores Roh m 1) was prepared, which was uniformly inoculated by spraying the plants.
  • the plants were cultivated in a moist chamber (dark for the first three days and under light for one day) at 25, and the degree of rice blast lesions on the leaves was examined.
  • Example 2 In a 6 cm diameter plastic flowerpot, 10 varieties of wheat (cultivar: chromium) were grown per pot, and the seedlings at the 1.5-leaf stage were prepared according to Example 2 according to Table 2.
  • the wettable powder of the compound (1) was diluted to 500 ppm with water containing a surfactant (0.01%) and sprayed at 2 Om1 per pot.
  • the plants were grown in a glass greenhouse for 10 days, and the degree of the powdery mildew spot on the first leaf was examined.
  • One cucumber (cultivar: Sagami Hanshiro) is grown per pot in a plastic flower pot with a diameter of 6 cm.
  • the seedlings at the 5-leaf stage are prepared as described in Table 1 according to Example 2.
  • the wettable powder of the compound (1) was diluted to 500 ppm with water containing a surfactant (0.01%) and sprayed at 20 ml per pot. After spraying, the cells were cultured in a glass greenhouse for 2 days. Then, cucumber and zoospores of the fungus were prepared from the diseased leaves.
  • the plants were kept in the dark at 20 ° C for 2 days, then grown in a glass greenhouse for 5 days, and the extent of the cucumber and the lesions appearing on the first leaf were examined.
  • Paper towels moistened with distilled water were spread in a plastic case (35 cm x 25 cm), and the cut leaves of Japanese cucumber (variety: Sagami Hanjiro) cotyledons were lined up.
  • the plastic case was closed, closed with vinyl tape, and kept in a constant temperature oven at 20 ° C for 4 days, and the degree of the fungus spots on the cotyledon that appeared on the cotyledon was examined.
  • the novel 5-azolyl pyrimidine compound of Honkiaki has an excellent agricultural and horticultural bactericidal effect.

Abstract

L'invention concerne des composés de 5-azolylpyrimidine de formule générale (1), dans laquelle R1 représente SO¿mR?4, hydrogène, alcoxy C¿1?-C20 ou analogues (où R?4¿ représente pyridyle ou alkyle C¿1?-C6 et m représente un entier compris entre 0 et 2); R?2¿ représente halogéno, alcoxy C¿1?-C6, haloalcoxy C1-C6, phénoxy ou analogues; R?3¿ représente alcoxy C¿1?-C20, SOmR?5¿, O-(CH¿2)n-R?6, hydrogène, alcényloxy C¿3?-C9, halogéno, haloalcoxy C1-C6, alkynyloxy C3-C9 ou analogues (où R?5¿ représente alkyle C¿1?-C6 et n représente un entier compris entre 1 et 4); et Y représente CH ou N. L'invention concerne également un procédé de préparation de ces composés et des germicides à usage agricole et horticole, contenant ces composés.
PCT/JP1999/007204 1998-12-22 1999-12-22 Composes de 5-azolylpyrimidine, procede de preparation de ces composes et germicides a usage agricole et horticole WO2000037460A1 (fr)

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JP10364097A JP2000186089A (ja) 1998-12-22 1998-12-22 ５−アゾリルピリミジン誘導体、その製法及び農園芸用の殺菌剤
JP10/364097 1998-12-22

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WO2000037460A1 true WO2000037460A1 (fr) 2000-06-29

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005012286A1 (fr) * 2003-07-25 2005-02-10 Amgen Inc. Pyridones et pyrimidinones substituees a proprietes anti-inflammatoires

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5613461B2 (ja) * 2010-06-02 2014-10-22 日本農薬株式会社 ピリミジン誘導体及び該誘導体を含有する農園芸用殺虫剤並びにその使用方法
JP2012102090A (ja) * 2010-10-15 2012-05-31 Sumitomo Chemical Co Ltd ピリミジン化合物およびその有害生物防除用途

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5536402A (en) * 1978-06-22 1980-03-14 Hokko Chem Ind Co Ltd Derivative of pyrazolylpyrimidine
EP0249938A2 (fr) * 1986-06-19 1987-12-23 Nissan Chemical Industries Ltd. Dérivés d'imidazolesulfonamides, herbicides et méthode pour inhiber la croissance de plantes indésirables
EP0417875A2 (fr) * 1989-09-14 1991-03-20 Schering Aktiengesellschaft Nitroanilides de l'acide 1-méthoxypyrimidinyl-1H-1,2,4-triazole-3-sulfonique, procédé pour leur préparation et leur application comme agents à activité herbicide
EP0484750A1 (fr) * 1990-11-06 1992-05-13 Bayer Ag Sulfonylaminotriazolylpyrimidines substituées
WO1999065897A1 (fr) * 1998-06-19 1999-12-23 Chiron Corporation Inhibiteurs de glycogene synthase kinase 3

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5536402A (en) * 1978-06-22 1980-03-14 Hokko Chem Ind Co Ltd Derivative of pyrazolylpyrimidine
EP0249938A2 (fr) * 1986-06-19 1987-12-23 Nissan Chemical Industries Ltd. Dérivés d'imidazolesulfonamides, herbicides et méthode pour inhiber la croissance de plantes indésirables
EP0417875A2 (fr) * 1989-09-14 1991-03-20 Schering Aktiengesellschaft Nitroanilides de l'acide 1-méthoxypyrimidinyl-1H-1,2,4-triazole-3-sulfonique, procédé pour leur préparation et leur application comme agents à activité herbicide
EP0484750A1 (fr) * 1990-11-06 1992-05-13 Bayer Ag Sulfonylaminotriazolylpyrimidines substituées
WO1999065897A1 (fr) * 1998-06-19 1999-12-23 Chiron Corporation Inhibiteurs de glycogene synthase kinase 3

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005012286A1 (fr) * 2003-07-25 2005-02-10 Amgen Inc. Pyridones et pyrimidinones substituees a proprietes anti-inflammatoires
AU2004261587B2 (en) * 2003-07-25 2008-02-21 Amgen Inc. Substituted pyridones and pyrimidinones with antiinflammatory properties

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