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WO1998003272A1 - Procedes pour la preparation de composes de 4-amino-5-chloro-6-(1-fluoroethyle)pyrimidine - Google Patents

Procedes pour la preparation de composes de 4-amino-5-chloro-6-(1-fluoroethyle)pyrimidine Download PDF

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Publication number
WO1998003272A1
WO1998003272A1 PCT/JP1997/002475 JP9702475W WO9803272A1 WO 1998003272 A1 WO1998003272 A1 WO 1998003272A1 JP 9702475 W JP9702475 W JP 9702475W WO 9803272 A1 WO9803272 A1 WO 9803272A1
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WO
WIPO (PCT)
Prior art keywords
group
carbon atoms
compound
chloro
atom
Prior art date
Application number
PCT/JP1997/002475
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English (en)
Japanese (ja)
Inventor
Katsutoshi Fujii
Yoshinori Yamanaka
Yasushi Nakamoto
Original Assignee
Ube Industries, Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ube Industries, Ltd. filed Critical Ube Industries, Ltd.
Publication of WO1998003272A1 publication Critical patent/WO1998003272A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom

Definitions

  • the present invention relates to a method for producing a 4-amino-5-chloro-6-O-fluroyl pyrimidine compound which is useful as a medicament or a drug, and more particularly, to an industrially advantageous method for producing this compound.
  • a 4-amino-5-chloro-6-O-fluroyl pyrimidine compound which is useful as a medicament or a drug, and more particularly, to an industrially advantageous method for producing this compound.
  • Numerous compounds are known as the 4-amino-5-chloro-6- (1-1 full-year-old rotyl) pyrimidine compound produced by the present invention, and insecticides, acaricides, and? It is also known to be useful as an S fungicide, a nematicide, etc. (for example, Japanese Patent Application Laid-Open Nos. 5-194417, 5-23036, Japanese Unexamined Patent Publication No. Hei 6—2,5187, Japanese Unexamined Patent Publication No. Hei 6-116,247, Japanese Unexamined Patent Publication No. Hei 6-247939, Japanese Unexamined Patent Publication No. Hei 7-258,223, Japanese Patent Application Laid-Open No. H08-113135, etc.).
  • A represents an alkyl group, an aralkyl group, a cycloalkyl group, or the like, and is a method of reacting with various amines represented by.
  • reaction intermediate 4-halogeno 5-chloro-6- (1-1 full-year rotyl) pyrimidine, is disclosed in JP-A-5-194417.
  • R 2 represents a lower acyl group
  • M represents an alkali metal
  • the target compound can be produced by a method of reacting a fluorinating agent represented by
  • the target compound can be produced by a method of reacting with an alkali gold fluorine compound represented by the following formula.
  • this method uses N, N-dimethylformamide (DMF), N, N-dimethylacetamide (DMA), 1,3-dimethyl-2-imidazolidone, dimethylsulfoxide, sulfolane and mixtures thereof as solvents.
  • DMF N, N-dimethylformamide
  • DMA N, N-dimethylacetamide
  • 1,3-dimethyl-2-imidazolidone dimethylsulfoxide
  • sulfolane 1,3-dimethyl-2-imidazolidone
  • this manufacturing method is also not an industrial manufacturing method.
  • An object of the present invention is to provide an industrial production method of a 4-amino-5-chloro-6- (1 -full-year-old rotyl) pyrimidine compound useful as a medicine and a pesticide. Disclosure of the invention
  • the present invention is as follows.
  • R is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, an unsubstituted or halogen atom, a carbon atom having 1 to 4 alkyl groups, An alkoxy group having 1 to 4 carbon atoms, a benzoyl group having at least one of haloalkyl groups having 1 to 4 carbon atoms as a substituent, a haloalkyl group having 1 to 4 carbon atoms, Octoalkoxy, halo with 2 to 5 carbon atoms Alkylcarbonyl group, alkylsulfonyloxy group having 1 to 4 carbon atoms, haloalkylsulfonyloxy group having 1 to 4 carbon atoms, (alkoxy group having 1 to 4 carbon atoms) iminobenzyl group, 2-phenyl At least one of a 1,3-dioxolanyl group, an alkoxy
  • alkylcarbonyl group having 1 to 4 carbon atoms Represents an alkynyl group having 2 to 5 carbon
  • M represents an alkali metal
  • alkali metal fluorine compounds represented by
  • R 1 represents an alkyl group having 4 to 4 carbon atoms, a benzyl group or a phenyl group, and X is as defined above.
  • the present invention relates to a method for producing a 4-amino-5-chloro-6- (1-fluoroethyl) pyrimidine compound represented by the formula:
  • the invention further provides:
  • R ′ is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, a haloalkyl group having 1 to 4 carbon atoms, and a carbon atom having 1 to 4 carbon atoms.
  • M represents an alkali metal
  • R ′ is as defined above
  • the present invention relates to a method for producing a 4-amino-5-chloro- (11-full-year rotyl) pyrimidine compound represented by the formula: BEST MODE FOR CARRYING OUT THE INVENTION
  • R represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, a benzoyl group, a haloalkyl group having 1 to 4 carbon atoms, a carbon atom of 1 to 4 carbon atoms.
  • alkyl group examples include a linear or branched alkyl group; preferably an alkyl group having 1 to 4 carbon atoms; and more preferably CH 3 and t-C 4 H 9 .
  • Alkoxy groups include linear or branched ones; preferably those having 1 to 4 carbon atoms; more preferably —OCH 3 and 1 OC 2 H 5 .
  • halogen atom examples include a fluorine atom, a chlorine atom, an iodine atom and an iodine atom; preferred are a fluorine atom and a chlorine atom.
  • Examples of the benzoyl group include unsubstituted and substituted groups.
  • Examples of the S-substituent include a halogen) atom, an alkyl group having 4 to 4 carbon atoms, an alkoxy group having 4 to 4 carbon atoms, and a haloalkyl group having 1 to 4 carbon atoms. it can.
  • the position of the substituent in the benzoyl group is not particularly limited; however, the 3_ position or the 4 position is preferable.
  • Substituted halogen atoms in the benzoyl group include fluorine, chlorine, bromine and iodine; fluorine and chlorine are preferred.
  • the dialkyl group in the benzoyl group may be linear or branched; preferably it has 1 to 4 carbon atoms; and more preferably CH 3 .
  • Examples of the substituted alkoxy group in the benzoyl group include straight-chain or branched ones; preferably one having 1 to 4 carbon atoms; more preferably —OCH 3 T.
  • alkyl has 1 to 4 carbon atoms.
  • examples thereof include linear or branched ones having a halogen atom such as a fluorine atom, a chlorine atom, a bromine urine, and an iodine atom; preferably, CF 3 is used.
  • the haloalkyl group include those in which alkyl is linear or branched having 1 to 4 carbon atoms and has a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. ; it is preferably CF 3.
  • haloalkoxy group examples include those in which alkoxy is straight or branched having 4 to 4 carbon atoms and having a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; preferably an OC F 3, -OCH F 2, - O CH 2 CF 3, -OC F 2 CHFCF 3, -OCH FCH F 2, - a OC F 2 CH FC I and single OC B r F 2.
  • a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom
  • haloalkylcarbonyl group examples include those in which alkyl is linear or branched having 1 to 4 carbon atoms and having an octagen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; preferably an COC F 3.
  • alkylsulfonyl group examples include those having a linear or branched alkyl group; preferably, it is OS 2 CH 3 .
  • haloalkylsulfonyloxy group examples include those in which the alkyl is linear or branched having 1 to 4 carbon atoms and has a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. But preferably one OS 0 2 CF 3 .
  • iminobenzyl group examples include those having an alkoxy group having 1 to 4 carbon atoms. And, as this alkoxy group, preferably one OCH
  • Examples of the 2-phenyl-3-dioxolanyl group include unsubstituted and those having a halogen atom as a substituent.
  • the position of the substituent in the 2-phenyl 1,3-dioxolanyl group is not particularly limited; however, the 4-position of the phenyl moiety is preferred.
  • Examples of the substituted halogen atom in the 2-phenyl-1,3-dioxolanyl group include a fluorine atom, a chlorine atom, an iodine atom and an iodine atom; a chlorine atom is preferred.
  • Examples of the benzyl group include unsubstituted and substituted ones.
  • the substituent includes a halogen atom and a hydroxyl group.
  • the position of the substituent in the benzyl group is not particularly limited; the ⁇ -position is preferred.
  • Examples of the substituted halogen atom in the benzyl group include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; a fluorine atom and a chlorine atom are preferred.
  • phenoxy groups include unsubstituted and substituted groups.
  • substituents include a halogen atom and a haloalkyl group having 1 to 4 carbon atoms.
  • Substituted halogen atoms in the phenoxy group include fluorine, chlorine, bromine and iodine; fluorine and chlorine are preferred.
  • haloalkyl group in the phenoxy group examples include those in which the alkyl is a linear or branched alkyl group having 1 to 4 carbon atoms and has a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom and an iodine atom. Although it is; Ru preferably CF 3 der.
  • Examples of the tri (C 4 alkyl) silylalkoxy group include those in which the alkyl and alkoxy groups are linear or branched; preferably, the alkyl and alkoxy have carbon atoms! And more preferably 4 CH 2 S i (CH 3 ) 3 .
  • alkylthio group having 1 to 4 carbon atoms examples include those having a linear or branched alkyl group; one SCH 3 is preferable.
  • Examples of the pyridyl group include unsubstituted and substituted groups.
  • Examples of the substituent include a halogen atom and a haloalkyl group having 1 to 4 carbon atoms.
  • Examples of the substituted halogen atom in the pyridyloxy group include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; a fluorine atom is preferred.
  • Examples of the substituted haloalkyl group in the pyridyloxy group include those in which the alkyl is linear or branched having 1 to 4 carbon atoms and having a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. But preferably CF3.
  • Preferred pyridyl radicals include pyridine-12-yl and pyridine-13-yl, and most preferably pyridine-12-isole.
  • the position of the substituent in the pyridyloxy group is not particularly limited; however, the 3-position and the 5-position are preferred.
  • alkylsulfonyl group examples include those having a linear or branched alkyl group; preferably, one is SO 2 CH 3 .
  • alkylsulfinyl group there may be mentioned also have a linear or branched alkyl group; preferably an S 0 CH 3.
  • alkyl is a straight-chain or
  • haloalkylthio group include those in which alkyl is linear or branched having 4 to 4 carbon atoms and having a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom and an iodine atom.
  • Alkylcarbonyl groups include straight or branched ones having 2 to 5 carbon atoms; preferably one COCH 3 .
  • the alkynyloxy group may be a straight-chain or branched one having 2 to 5 carbon atoms; preferably one OCH 2 C ⁇ CH.
  • n an integer of 1 to 5, preferably 1, 2 or 3.
  • M examples include alkali metals such as sodium, potassium, and cesium; potassium or cesium is preferred.
  • R ′ is hydrogen atom, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, halogen atom, number of haloalkyl groups having up to 4 carbon atoms, number of carbon atoms Examples thereof include 1 to 4 haloalkoxy groups and a nitro group.
  • alkyl group examples include linear or branched ones having 1 to 4 carbon atoms; preferably, a methyl group and an ethyl group.
  • alkoxy group examples include straight or branched ones having 1 to 4 carbon atoms; preferably, a methoxy group or an ethoxy group.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; preferably, a fluorine atom and a chlorine atom.
  • octaalkyl group examples include those in which the alkyl is a straight-chain or branched-chain alkyl group having 1 to 4 carbon atoms and having a halogen atom such as poly, a fluorine atom, a chlorine atom, an iodine atom and an iodine atom. it can but; is preferably an CF 3.
  • haloalkoxy group examples include those in which alkoxy has a straight or branched chain having 1 to 4 atoms, and has a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. But preferably with one OCF 3 , one OCH F 2 , —OCH 2 CF 3 , —OC F 2 CH FC F 3 , one OCH FCHF 2 , —OCF 2 CH FC I and one OC B r F 2 Yes; more preferably one OCF 3 and one CH 2 CF 3 .
  • R 1 examples include an alkyl group having 1 to 4 carbon atoms, a benzyl group and a phenyl group; an alkyl group having 1 to 4 carbon atoms; and an n-butyl group is more preferable.
  • X is an octogen atom, and may include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; and preferably a chlorine atom and a bromine atom.
  • alkali metal fluorine compound MF examples include sodium fluoride, potassium fluoride, and cesium fluoride, with preference given to fluorinated lithium.
  • phase transfer catalyst (R 1 ), ⁇ ; compound (3) include triethyl benzylammonium chloride, tetramethylammonium chloride, triethylbenzylammonium bromide, tributylbenzylammonium chloride, Trimethylbenzylammonium chloride, trimethylphenylammonium bromide, tetramethylammonium bromide, tetraethylammonium bromide, tetra-bromoammonium bromide, tetramethylammonium iodide, tetramethylammonium iodide, tetra-bromoiodide -Petit ammonium.
  • the compound (1) used in the present invention is disclosed in Compound (7) and compound (12) can be produced by reacting compound (7) with compound (12) in the presence or absence of a solvent in the same manner as described in JP-A-8223.
  • R, X and n are as defined above.
  • the present invention relates to a method for producing a compound (1A) and a compound (2) by reacting the compound (1A) and the compound (2) in the absence of a solvent or in a solvent in the presence of a phase transfer catalyst (R 1 ) 4 NX; Can be.
  • the compound (2) can be used in an amount of 1 to 10 moles per mole of the compound (1A); preferably 3 to 5 moles.
  • the compound (3) can be used in an amount of 0.01 to 2 times mol of the compound (1A); preferably 0.3 to 0 times mol.
  • 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, ligroin, hexane, chlorobenzene, dichlorobenzene, and methylene chloride. , Chlorinated or non-chlorinated aromatic, aliphatic, and lipophilic hydrocarbons, such as chloroform, dichloroethane, trichloroethylene, and cyclohexane; such as getyl ether, tetrahydrofuran, and dichlorohexane.
  • DMI 1,3-dimethyl-2-imidazolidone
  • the amount of the solvent to be used may be such that the amount of the compound (3) is 5 to 100% by weight; it is preferably 10 to 50% by weight.
  • the reaction temperature is in the temperature range from room temperature to the boiling point of the solvent to be used, but it is preferably from 110 to 130 ° C.
  • the reaction time varies depending on the concentration and temperature described above; it can be usually carried out for 2 to 5 hours.
  • the target compound (1A) produced as described above is subjected to ordinary post-treatments such as extraction, concentration, filtration, etc., and, if necessary, recrystallization and various chromatographic methods. It can be appropriately purified by known means such as.
  • the compound (1B) used in the present invention is obtained by dissolving the compound (14) and the compound (15) in the presence of a base in the same manner as described in JP-A-7-258223, as shown below. It can be easily produced by reacting in a medium or a solvent. '
  • the compound (2) used in the present invention is the same as described above, and a commercially available product (for example, spray-dried potassium difluoride) can be used.
  • a commercially available product for example, spray-dried potassium difluoride
  • the target compound (4B) can be produced by reacting the compound (1B) with the compound (2) in a solvent.
  • Examples of the type of the solvent include formamide, N-methylformamide, or a mixture of formamide or N-methylformamide and 1,3-dimethyl-2-imidazolidone (DMI).
  • the amount of the solvent to be used may be such that the amount of the compound (1B) is 5 to 80% by weight; however, it is preferably 0 to 50% by weight.
  • the compound (2) can be used in such an amount that it is used in an amount of up to 10-fold the molar amount of the compound (1B); preferably a 2- to 5-fold molar amount.
  • the reaction temperature is within the temperature range from room temperature to the boiling point of the solvent used or less; preferably 50 to 10 CTC.
  • reaction time varies depending on the degree of rheology and the degree of the above; it can be generally carried out for about 1 to 3 hours.
  • the target compound (4B) produced as described above is subjected to ordinary post-treatments such as extraction, concentration, and oxidation, and, if necessary, recrystallization and various chromatographies. It can be appropriately purified by known means such as.
  • reaction mixture was cooled to room temperature, water (20 ml) and acetic acid ethyl (20 ml) were added, and the mixture was stirred.
  • the aqueous layer was extracted again with ethyl sulphate, combined with the ethyl sulphate ring, washed with water, dried over anhydrous sodium sulfate, and the ethyl sulphate was distilled off under reduced pressure, and the resulting oil was subjected to column chromatography.
  • Table 1 shows the compounds synthesized as described above and their physical properties.
  • Table 2 shows the compounds synthesized as described above and their physical properties.
  • the mixture was heated and stirred for 1 hour.
  • Table 3 shows a comparison of the production results of the compound (4) in the present invention and Comparative Examples.
  • the total yield of all steps is 24.0%.
  • 4,5-Dichloro-6-ethylpyrimidine (270 g) was dissolved in dichloromethane (750 ml), heated at 30 to 35, and blown with chlorine gas for 2 hours with stirring. After completion of the reaction, nitrogen gas was blown into the reaction solution to remove excessively dissolved chlorine gas. Then, dichloromethane was distilled off under reduced pressure, and the obtained oil was distilled under reduced pressure to obtain 240 g of the target substance as a pale yellow liquid.
  • 2-Phenylethylamine (1.2 g) and triethylamine (1.2 g) were dissolved in toluene (30 ml), and then 4-promo 6- (1-promoethyl) -15-chloropyrimidine (3.0 g) and stirred at about 40 for 4 hours.
  • Table 4 shows the compounds synthesized as described above and their physical properties.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

On peut préparer à l'échelle industrielle des composés de 4-amino-5-chloro-6-(1-fluoroéthyle)pyrimidine représentés par la formule générale (1), utiles comme agents de lutte contre les parasites en agriculture et en horticulture, en faisant réagir de la 5-chloro-6-(1-chloroéthyle)-4-(2-phényléthylamino)pyrimidine avec du fluorure de potassium en présence de bromure de n-tétrabutylammonium, ou en faisant réagir de la 5-chloro-6-(1-bromoéthyle)-4-(2-phényléthylamino)pyrimidine avec du fluorure de potassium.
PCT/JP1997/002475 1996-07-19 1997-07-17 Procedes pour la preparation de composes de 4-amino-5-chloro-6-(1-fluoroethyle)pyrimidine WO1998003272A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP19028096A JPH1036355A (ja) 1996-07-19 1996-07-19 ４−アミノ−５−クロロ−６−（１−フルオロエチル）ピリミジン誘導体の製法
JP8/190280 1996-07-19

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WO1998003272A1 true WO1998003272A1 (fr) 1998-01-29

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013113787A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés de pyrimidine fongicides
WO2013113776A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés de pyrimidine fongicides
WO2013113720A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés de pyrimidine fongicides
WO2013113778A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés de pyrimidine fongicides
WO2013113863A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés de pyrimidine fongicides
WO2013113773A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés fongicides de pyrimidine
WO2013113719A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés de pyrimidine fongicides ii
WO2013113782A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés de pyrimidine fongicides
WO2013113781A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés de pyrimidine fongicides i
WO2013113716A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés de pyrimidine fongicides
US9072301B2 (en) 2012-02-03 2015-07-07 Basf Se Fungicidal pyrimidine compounds

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999052880A1 (fr) * 1998-04-14 1999-10-21 Ube Industries, Ltd. Derives 5-iodo-4-phenethylaminopyrimidine, leurs intermediaires, procede de production associe, et pesticides agricoles et horticoles
CN103772369B (zh) 2012-10-25 2016-12-21 沈阳中化农药化工研发有限公司 胡椒乙胺类化合物及其用途
US9770026B2 (en) * 2012-10-25 2017-09-26 Shenyang Sinochem Agrochemicals R&D Co., Ltd. Substituted pyrimidine compound and uses thereof
CN103772293B (zh) * 2012-10-25 2015-09-09 中国中化股份有限公司 含氟嘧啶类化合物及用途
CN103772294B (zh) * 2012-10-25 2015-09-09 中国中化股份有限公司 苯氧基嘧啶胺类化合物及用途
CN104710409B (zh) 2013-12-13 2019-06-04 沈阳中化农药化工研发有限公司 吡唑基嘧啶胺类化合物及用途

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JPH01301636A (ja) * 1988-05-31 1989-12-05 Central Glass Co Ltd １，２，２，２−テトラフルオロエチルジフルオロメチルエーテルの製造法
JPH04164068A (ja) * 1990-10-26 1992-06-09 Asahi Glass Co Ltd フッ素化ピリジン類の製造方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01301636A (ja) * 1988-05-31 1989-12-05 Central Glass Co Ltd １，２，２，２−テトラフルオロエチルジフルオロメチルエーテルの製造法
JPH04164068A (ja) * 1990-10-26 1992-06-09 Asahi Glass Co Ltd フッ素化ピリジン類の製造方法

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013113787A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés de pyrimidine fongicides
WO2013113776A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés de pyrimidine fongicides
WO2013113720A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés de pyrimidine fongicides
WO2013113778A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés de pyrimidine fongicides
WO2013113788A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés de pyrimidine fongicides
WO2013113863A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés de pyrimidine fongicides
WO2013113791A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés de pyrimidine fongicides
WO2013113773A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés fongicides de pyrimidine
WO2013113719A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés de pyrimidine fongicides ii
WO2013113782A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés de pyrimidine fongicides
WO2013113781A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés de pyrimidine fongicides i
WO2013113716A1 (fr) 2012-02-03 2013-08-08 Basf Se Composés de pyrimidine fongicides
US9055750B2 (en) 2012-02-03 2015-06-16 Basf Se Fungicidal pyrimidine compounds
US9072301B2 (en) 2012-02-03 2015-07-07 Basf Se Fungicidal pyrimidine compounds

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