WO2021193432A1 - Procédé de production d'un intermédiaire de production de cyclaniliprole - Google Patents

Procédé de production d'un intermédiaire de production de cyclaniliprole Download PDF

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Publication number
WO2021193432A1
WO2021193432A1 PCT/JP2021/011379 JP2021011379W WO2021193432A1 WO 2021193432 A1 WO2021193432 A1 WO 2021193432A1 JP 2021011379 W JP2021011379 W JP 2021011379W WO 2021193432 A1 WO2021193432 A1 WO 2021193432A1
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WIPO (PCT)
Prior art keywords
compound
salt
formula
compound represented
cyclaniliprol
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PCT/JP2021/011379
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English (en)
Japanese (ja)
Inventor
堅一 浅川
祐介 熊倉
祐樹 高橋
大介 森戸
美樹 菅田
文浩 福井
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石原産業株式会社
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Application filed by 石原産業株式会社 filed Critical 石原産業株式会社
Priority to JP2022510423A priority Critical patent/JPWO2021193432A1/ja
Priority to KR1020227032717A priority patent/KR20220157967A/ko
Priority to CN202180022473.XA priority patent/CN115335368A/zh
Publication of WO2021193432A1 publication Critical patent/WO2021193432A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/04—Insecticides

Definitions

  • the present invention relates to a method for producing an intermediate for producing cyclaniliprol. Furthermore, the present invention also relates to a method for producing cyclaniliprol using the intermediate for producing cyclaniliprol.
  • Cycraniliprole (3-bromo-N- [2-bromo-4-chloro-6-[[(1-cyclopropylethyl) amino] carbonyl] phenyl] -1- (3-chloropyridin-2-) (Il) -1H-pyrazole-5-carboxamide; a compound represented by the formula (IV) described later) is described as Compound No. 16 in Patent Document 1, and is useful as an active ingredient of a commercially available agricultural pesticide.
  • Compound. As a method for producing cyclaniliprol, for example, Patent Documents 2 to 4 are known. Further, a compound having a structure similar to that of cyclaniliprol and a method for producing the same are also known (for example, Patent Documents 5 to 10).
  • cyclaniliprol When cyclaniliprol is industrially manufactured as an active ingredient for pesticides, it must comply with the prescribed standards.
  • the problem to be solved by the present invention is to produce high-purity cyclaniliprol in high yield and at low cost. More specifically, it is intended to suppress the inclusion of the impurity (B) described later in cyclaniliprol as an active ingredient of pesticides, and to produce cyclaniliprol with high yield and high purity.
  • Patent Document 1 describes a method that can be used for producing cyclaniliprol as reaction [A].
  • the present inventors produce cyclaniliprol represented by the formula (IV) according to the following scheme according to this reaction [A]
  • the compounds represented by the formula (B) which are impurities hereinafter referred to as “B”.
  • Impurity (B) is produced as a by-product, and it is very difficult to remove this impurity (B) from the obtained cyclaniliprol. It was found that it is not suitable for the production of high-purity cyclaniliprol that meets the above standards.
  • Patent Document 2 discloses a method for producing cyclaniliprol via reaction [N] as a method for producing cyclaniliprol using a raw material having no Br on the benzene ring. ..
  • the yield of Example 17 (4) is very low, about 14%
  • the yield of Example 19 (2) is very low, about 37%.
  • the problem concerning the generation of the impurity (B) is not described in Patent Document 2 and is not recognized.
  • the present invention is a compound represented by the formula (I) or a salt thereof (hereinafter, also simply referred to as a compound (I)):
  • R is OH or halogen
  • compound (I) useful for producing cyclaniliprol can be produced in high yield and high purity. Furthermore, from the compound (I) obtained by the present invention, high-purity cyclaniliprol satisfying the specifications as an active ingredient for pesticides can be produced.
  • the method for producing compound (I) of the present invention is characterized by reacting compound (II) with compound (III) in the presence of a condensing agent and / or a base.
  • a condensing agent and / or a base when R is OH, the compound (II) and the compound (III) are preferably reacted in the presence of a condensing agent and a base, and when R is a halogen, the compound (II) and the compound (II) are reacted. It is preferable to react with compound (III) in the presence of a base. This reaction may be carried out in the presence of a solvent.
  • the salt of the compound (I), the compound (II) or the compound (III) includes any pesticide-acceptable salt, for example, an alkali metal salt (sodium salt, potassium salt, etc.), alkaline earth.
  • Metal salts magnesium salts, calcium salts, etc.
  • ammonium salts alkylammonium salts (dimethylammonium salts, triethylammonium salts, etc.)
  • acid addition salts salts, perchlorates, sulfates, nitrates, acetates, methanesulfones) (Salt, etc.) and the like.
  • the halogen represented by R include chlorine, bromine, iodine and the like, and chlorine is preferable.
  • the amount of compound (II) and compound (III) to be used is not particularly limited as long as the reaction proceeds, but is, for example, 0.8 to 1.2 mol, preferably 0. 9 to 1.1 mol, more preferably 0.95 to 1.05 mol of compound (III) can be used.
  • the compound (II) and the compound (III) in the present invention can be produced by a method known in the art, for example, the method described in Patent Documents 2, 5, 7 or the like, or a method similar thereto, or commercially available. Goods can also be used.
  • a compound (III) in which R is halogen is used
  • the compound (III) in which R is halogen is a halogenating agent (III) in which R is OH according to a method well known in the art. It can also be obtained by reacting with an acid halide such as thionyl chloride or oxalyl chloride).
  • sulfonyl chloride methanesulfonyl chloride, p-toluenesulfonyl chloride, etc.
  • acid halide thionyl chloride, oxalyl chloride, etc.
  • the amount of the condensing agent used is not particularly limited as long as the reaction proceeds, but is, for example, 1 to 2 mol, preferably 1 to 1.8 mol, more preferably 1 to 1 to 1 mol of the compound (II). It is 1.5 mol.
  • the bases used in this reaction include organic bases such as pyridine and picoline (for example, 2-picoline, 3-picoline, 4-picoline), alkali metal carbonates or alkali metal hydrogen carbonates, and alkaline earths.
  • organic bases such as pyridine and picoline (for example, 2-picoline, 3-picoline, 4-picoline), alkali metal carbonates or alkali metal hydrogen carbonates, and alkaline earths.
  • Inorganic bases such as metal carbonates or alkaline earth metal carbonates are preferred, among which pyridine, picoline (eg, 2-picoline, 3) are preferred from the standpoint of yield and purity of the resulting compound (I).
  • -Picoline, 4-picoline alkali metal carbonates or alkali metal carbonates are more preferred, and pyridine or picoline (eg 2-picoline, 3-picoline, 4-picoline) are even more preferred, among which 3-picoline. Is particularly preferable.
  • the above-mentioned base used in this reaction may be one kind or two or more kinds.
  • the amount of the base used is not particularly limited as long as the reaction proceeds, but is, for example, 0 to 10 mol, preferably 1 to 7 mol, and more preferably 1 to 4 mol with respect to 1 mol of the compound (II). be.
  • the solvent that may be used in this reaction is not particularly limited as long as it does not adversely affect the reaction, and is, for example, ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), nitriles (acetoyl, propionitrile, etc.). ), Ethers (tetratetra, diethyl ether, etc.), halogenated hydrocarbons (dichloromethane, dichloroethane, chloroform, chlorobenzene, etc.), esters (ethyl acetate, isopropyl acetate, etc.), polar solvents (dimethylformamide, dimethylacetamide, N.
  • ketones acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.
  • nitriles acetoyl, propionitrile, etc.
  • Ethers
  • -Methylpyrrolidone dimethylsulfoxide, etc.
  • aromatic hydrocarbons toluene, xylene, etc.
  • pyridines pyridine, picolin, etc.
  • the number is preferably two or more, and more preferably one or two or more selected from the group consisting of ketones, nitriles, ethers, polar solvents, and pyridines.
  • the amount of the solvent used is not particularly limited as long as the reaction proceeds, but is, for example, 0 to 50 times the amount (V / W), preferably 0 to 30 times the amount (V / W) of the compound (II). It is more preferably 0 to 20 times the amount (V / W), and further preferably 1 to 20 times the amount (V / W).
  • the order of addition of compound (II), compound (III), condensing agent and base, and optionally solvent is not particularly limited, and may be added and mixed in any order.
  • the addition of these components to the reaction system may be carried out all at once or in portions, or may be continuous.
  • all the components may be mixed at once, or some components may be added later, and specific examples of such addition include, for example, (i). ) Mix compound (II), base and solvent, and add compound (III) and condensing agent to it.
  • (Ii) Mix compound (II), compound (III) base and solvent, and add condensing agent there. Addition and the like can be mentioned.
  • the temperature of this reaction is usually about 0 to 50 ° C, preferably about 0 to 30 ° C.
  • the reaction time is usually about 1 to 24 hours, preferably about 1 to 5 hours.
  • room temperature usually means about 0 to 40 degreeC, more specifically, 10 to 30 degreeC.
  • compound (I) can be isolated by performing post-treatment by a conventional method such as neutralization, extraction, washing and drying, if necessary. Then, if necessary, compound (I) may be purified by a conventional method such as recrystallization and repulp. Alternatively, it can be used as it is in the next reaction without isolating compound (I) or purifying the isolated compound (I).
  • the purity of compound (I) obtained by this reaction is usually 95% by weight or more, preferably 97% by weight or more, and more preferably 98.5% by weight or more.
  • a compound represented by the following formula (A) or a salt thereof hereinafter, also simply referred to as an impurity (A) contained as an impurity:
  • the content of the compound is usually 1% by weight or less, preferably 0.3% by weight or less, based on the total amount of the compound represented by the formula (I) or a salt thereof and the impurity (A).
  • it is substantially free of impurities (A).
  • substantially not contained means that an amount of an impurity or the like may be mixed, and for example, the content ratio of the impurity (A) is less than 0.1% by weight.
  • Cyclaniliprol can be produced by reacting the compound (I) obtained as described above with a brominating agent. This reaction may be carried out in the presence of a base and a solvent. Examples of the brominating agent used in this method include bromine and hypobromous acid, and bromine is particularly preferable.
  • the amount of the brominating agent used is not particularly limited as long as the reaction proceeds, but for 1 mol of compound (I), for example, 0.5 to 5 mol, preferably 1 to 3 mol, more preferably 1 mol. Up to 2 moles of brominating agent can be used.
  • Bases that may be used in this reaction include metal hydroxides (sodium hydroxide, potassium hydroxide, calcium hydroxide, etc.), metal hydrides (sodium hydride, potassium hydride, etc.), and metal alkoxides (sodium methoxy). Do, sodium ethoxyoxide, potassium t-butoxide, etc.) are preferable, among these, metal hydroxide is more preferable, and sodium hydroxide and potassium hydroxide are further preferable.
  • the above-mentioned base used in this reaction may be one kind or two or more kinds. The amount of the base used is not particularly limited as long as the reaction proceeds, but is, for example, 1 to 10 mol, preferably 1.5 to 5 mol, more preferably 1.5 mol, per 1 mol of compound (I). ⁇ 3.5 mol.
  • the solvent that may be used in this reaction is not particularly limited as long as it does not adversely affect the reaction, but ethers (diethyl ether, butylmethyl ether, tetrahydrofuran, dioxane, dimethoxyethane, etc.) and halogenated hydrocarbons (chlorobenzene).
  • esters More preferably, it is one kind or two or more kinds selected from the group consisting of the kind.
  • the amount of the solvent used is not particularly limited as long as the reaction proceeds, but is, for example, 0 to 50 times the amount (V / W), preferably 1 to 30 times the amount (V / W) of the compound (I). The amount is 3 to 20 times (V / W).
  • the order of adding the compound (I), the brominating agent, and if necessary, the base and the solvent is not particularly limited, and the compounds may be mixed in any order.
  • the addition of these components to the reaction system may be carried out all at once or in portions, or may be continuous.
  • the order of addition is as follows: (i) compound (I) and a brominating agent, if necessary, a solvent is mixed and a base is added thereto, or (ii) compound (I) and a base, and if necessary, a solvent is mixed. Then, a brominating agent may be added thereto.
  • the temperature of this reaction is usually about ⁇ 20 to 120 ° C., preferably about 0 to 50 ° C.
  • the reaction time is generally about 0.5 to 48 hours, preferably about 1 to 24 hours.
  • cyclaniliprol can be isolated by performing post-treatment by a conventional method such as neutralization, extraction, washing and drying, if necessary. Further, due to the conditions of the reaction and / or post-treatment, cyclaniliprol may be isolated as a salt or a solvate, in which case, for example, a conventional method such as neutralization and solvation. Can be converted into a free cyclaniliprol. Then, if necessary, cyclaniliprol can be purified by a conventional method such as recrystallization or repulp. The purity of cyclaniliprol obtained by this reaction is usually 90% by weight or more, preferably 95% by weight or more, and more preferably 97% by weight or more. In addition to the cyclaniliprol obtained by this reaction, the compound represented by the following formula (B) or a salt thereof contained as an impurity:
  • the content of is usually 1% by weight or less, preferably 0.3% by weight or less, and more preferably impurities, based on the total amount of cyclaniliprol and the compound represented by the formula (B).
  • (B) is substantially not contained.
  • substantially not contained means that an amount of impurities may be mixed, and for example, the content ratio of impurities (B) is less than 0.1% by weight.
  • the various components in the method of the present invention are appropriately selected from the above-mentioned plurality of examples and conditions, for example, not only the above-mentioned examples and conditions in the normal range but also the examples and conditions in a preferable range. Can be combined with each other.
  • R is OH or halogen
  • R is OH
  • the compound represented by the formula (II) or a salt thereof is reacted with the compound represented by the formula (III) or a salt thereof in the presence of a condensing agent and a base.
  • R is a halogen
  • the compound represented by the formula (II) or a salt thereof is reacted with the compound represented by the formula (III) or a salt thereof in the presence of a base [1]. ]
  • the content ratio of [1] to [15] is 1% by weight or less based on the total amount of the compound represented by the formula (I) or a salt thereof and the compound represented by the formula (A) or a salt thereof.
  • a compound represented by the formula (I) obtained by the production method according to any one of [1] to [17] or a salt thereof is reacted with a brominating agent to form cyclaniliprol.
  • Production method [19] The production method according to [18], wherein the brominating agent is bromine or hypobromous acid.
  • the production method according to [18] or [19], wherein the reaction is carried out in the presence of a base.
  • the base is one or more selected from the group consisting of metal hydroxides, metal hydrides and metal alkoxides.
  • the production method according to [20] wherein the base is a metal hydroxide.
  • HPLC analysis conditions in this example are as follows.
  • Mobile phase Liquid A: 0.1% aqueous formic acid solution
  • Liquid B acetonitrile Gradient conditions are as follows.
  • the purity (content ratio) is indicated by an area% value by high performance liquid chromatography (HPLC) and / or a weight% value converted from the area%.
  • the area% value is obtained by measuring the reaction product obtained by the synthetic experiment by HPLC.
  • the weight% value is calculated by, for example, the conversion method described below.
  • a measurement solvent is added to the cyclaniliprol standard product to prepare a cyclaniliprol standard solution, and the standard solution is measured three times by HPLC.
  • the average value of the area values obtained by the HPLC measurement is calculated, and the average value is divided by the weight of the cyclaniliprol standard product used in the measurement to calculate the unit area value.
  • the unit area value of the compound (I) standard product, the impurity (A) standard product, or the impurity (B) standard product is calculated respectively.
  • the unit area value is calculated in the same manner.
  • the unit area value of the reaction product and the unit area value of the standard product are compared, the ratio is calculated, and the weight% value is calculated. It is also possible to calculate the sensitivity ratio from the unit area value of each of the above standard products and convert it from the sensitivity ratio to obtain the impurity content.
  • Example 1 Synthesis of compound (I) A mixture of 0.5 g of compound (II), 0.6 g of compound (IIIa), 0.59 g of 3-picoline and 10 mL of tetrahydrofuran is ice-cooled, and 0.31 g of methanesulfonyl chloride is used. Was slowly added dropwise under ice cooling. After completion of the dropping, the temperature was raised to room temperature, the mixture was stirred overnight at the same temperature, and then the reaction was checked by HPLC. As a result, compound (I) was produced in an area% of 88.1. At that time, no impurity (A) was detected.
  • Example 2 Synthesis of compound (I) A mixture of 0.5 g of compound (II), 0.6 g of compound (IIIa), 0.59 g of 3-picoline and 10 mL of N-methylpyrrolidone is ice-cooled and methanesulfonyl chloride. 0.31 g was slowly added dropwise under ice cooling. After completion of the dropping, the temperature was raised to room temperature, the mixture was stirred overnight at the same temperature, and then the reaction was checked by HPLC. As a result, compound (I) was produced in an area% of 98.6. At that time, no impurity (A) was detected.
  • the calculated average value was divided by 15.41, which is the mass value of the standard cyclaniliprol product, to calculate the unit area value of 66069.
  • the unit area values 72447, 91829 and 81242 of the compound (I), the impurity (A) and the impurity (B) were calculated.
  • the compound (I) obtained by synthesis is also calculated by comparing the area value obtained by the HPLC measurement with the unit area value of the standard product in the same manner, and the weight% value indicating the content ratio of impurities is calculated.
  • the weight% value indicating the content ratio of impurities is calculated.
  • Example 8 Synthesis of compound (I) 0.45 g of methanesulfonyl chloride at room temperature was slowly added to a mixed solution of 0.79 g of compound (II), 1.0 g of compound (IIIa), 0.39 g of sodium carbonate and 10 mL of acetone. Dropped. When the reaction was checked by HPLC after stirring at the same temperature for 1 hour, compound (I) was produced in 75.5 area%. At that time, no impurity (A) was detected. Subsequently, 0.15 g of sodium carbonate and 0.15 g of methanesulfonyl chloride were added to the reaction solution, and the mixture was stirred overnight at room temperature. As a result, compound (I) was produced in an area% of 97.2. At that time, no impurity (A) was detected.
  • Example 9 Synthesis of cyclaniliprol A mixed solution of 11.6 g of compound (I) and 58 mL of ethyl acetate obtained according to Example 3 was ice-cooled, and 5.2 g of bromine was slowly added dropwise. Next, 13.8 g of an aqueous sodium hydroxide solution was slowly added dropwise, and the mixture was stirred at the same temperature for 1 hour. After confirming that the reaction was completed, 12.7 g of an aqueous sodium sulfite solution under an ice bath was added dropwise, and the mixture was stirred at the same temperature for 1 hour. The slurry was filtered and the solid was washed with 11.6 g of water.
  • Example 11 Synthesis of compound (I) A mixture of 0.5 g of compound (II), 0.63 g of compound (IIIa), 0.39 g of 3-picoline, and 5 mL of pyridine as a solvent is ice-cooled and methanesulfonyl chloride. 0.26 g was slowly added dropwise under ice cooling. After completion of the dropping, the temperature was raised to room temperature, the mixture was stirred at the same temperature for 1 hour, and then the reaction was checked by HPLC. As a result, compound (I) was produced in an area% of 96.8. At that time, no impurity (A) was detected.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Insects & Arthropods (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Un procédé de production d'un intermédiaire de production de cyclaniliprole de pureté élevée est divulgué.　Selon ce procédé, un intermédiaire de production de cyclaniliprole de pureté élevée peut être produit à un rendement élevé par réaction d'un composé représenté par la formule (II) ou un sel de celui-ci avec un composé représenté par la formule (III) ou un sel de celui-ci en présence d'un agent de condensation et/ou d'une base. En utilisant cet intermédiaire, un cyclaniliprole de haute pureté peut être produit.
PCT/JP2021/011379 2020-03-25 2021-03-19 Procédé de production d'un intermédiaire de production de cyclaniliprole WO2021193432A1 (fr)

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JP2022510423A JPWO2021193432A1 (fr) 2020-03-25 2021-03-19
KR1020227032717A KR20220157967A (ko) 2020-03-25 2021-03-19 시클라닐리프롤의 제조 중간체의 제조 방법
CN202180022473.XA CN115335368A (zh) 2020-03-25 2021-03-19 环溴虫酰胺的制造中间体的制造方法

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JP2020054157 2020-03-25

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JP2009013158A (ja) * 2006-12-15 2009-01-22 Ishihara Sangyo Kaisha Ltd アントラニルアミド系化合物の製造方法
US20100317864A1 (en) * 2008-04-01 2010-12-16 Bin Li Preparation Method of Phenylcarboxamides
WO2020117493A1 (fr) * 2018-12-03 2020-06-11 Fmc Corporation Procédé de préparation de n-phénylpyrazole-1-carboxamides

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TWI356822B (en) 2001-08-13 2012-01-21 Du Pont Novel substituted dihydro 3-halo-1h-pyrazole-5-car
TWI343376B (en) 2002-07-31 2011-06-11 Du Pont Method for preparing 3-halo-4, 5-dihydro-1h-pyrazoles
DK1717237T3 (da) 2004-02-18 2011-03-07 Ishihara Sangyo Kaisha Anthranilamid, fremgangsmåde til fremstilling deraf samt skadedyrsbekæmpelsesmidler indeholdende samme
TWI363756B (en) * 2004-12-07 2012-05-11 Du Pont Method for preparing n-phenylpyrazole-1-carboxamides
TWI395728B (zh) 2006-12-06 2013-05-11 Du Pont 製備２-胺基-５-氰基苯甲酸衍生物之方法
ZA200903986B (en) * 2006-12-15 2010-08-25 Ishihara Sangyo Kaisha Process for producing anthranilamide compound
CN104496901B (zh) * 2006-12-15 2016-05-25 石原产业株式会社 邻氨基苯甲酰胺系化合物的制造方法
JP2009001541A (ja) 2006-12-15 2009-01-08 Ishihara Sangyo Kaisha Ltd 新規ピラゾール化合物を中間体として用いるアントラニルアミド系化合物の製造方法
JP2009023991A (ja) 2007-06-20 2009-02-05 Ishihara Sangyo Kaisha Ltd アントラニルアミド系化合物の製造方法
WO2019207595A1 (fr) 2018-04-23 2019-10-31 Natco Pharma Limited Procédé amélioré pour la préparation de dérivés d'anthranilamide

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009013158A (ja) * 2006-12-15 2009-01-22 Ishihara Sangyo Kaisha Ltd アントラニルアミド系化合物の製造方法
US20100317864A1 (en) * 2008-04-01 2010-12-16 Bin Li Preparation Method of Phenylcarboxamides
WO2020117493A1 (fr) * 2018-12-03 2020-06-11 Fmc Corporation Procédé de préparation de n-phénylpyrazole-1-carboxamides

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CN115335368A (zh) 2022-11-11
KR20220157967A (ko) 2022-11-29

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