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WO2005068430A1 - Derives pyridylmethyles de l'acide 2,6-dichloroisonicotinique, leur procede de production, et agents de lutte contre des maladies pour utilisation en agriculture et en horticulture - Google Patents

Derives pyridylmethyles de l'acide 2,6-dichloroisonicotinique, leur procede de production, et agents de lutte contre des maladies pour utilisation en agriculture et en horticulture Download PDF

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Publication number
WO2005068430A1
WO2005068430A1 PCT/JP2005/000211 JP2005000211W WO2005068430A1 WO 2005068430 A1 WO2005068430 A1 WO 2005068430A1 JP 2005000211 W JP2005000211 W JP 2005000211W WO 2005068430 A1 WO2005068430 A1 WO 2005068430A1
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WO
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Prior art keywords
group
pyridylmethyl
substituted
atom
formula
Prior art date
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Ceased
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PCT/JP2005/000211
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English (en)
Japanese (ja)
Inventor
Tsumoru Watanabe
Nobuyuki Araki
Nobuyuki Kusano
Yuichi Kokaji
Yoshitaka Niizeki
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Kureha Corp
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Kureha Corp
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Priority to JP2005517028A priority Critical patent/JP4706482B2/ja
Publication of WO2005068430A1 publication Critical patent/WO2005068430A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

Definitions

  • the present invention relates to a pyridylmethyl 2,6-dicyclomouth isonicotinate derivative, a method for producing the same, and an agricultural and horticultural disease control agent containing the pyridylmethyl 2,6-dichloromouth isonicotinate derivative as an active ingredient.
  • 2,6-dicyclomouth isonicotinic acid has been known to be used as a plant disease protective composition (see Patent Documents 14 to 14).
  • Patent Documents 14 to 14 For pyridylmethyl 2,6-dichloroisonicotinate, 2,2-dichloropyridyl methyl isonicotinate, 2,6-dichloropyridyl isonicotinic acid 3-pyridylmethyl ester,
  • Use of oral isonicotinic acid 4-pyridylmethyl ester as a plant disease protection composition is known (see Patent Document 5).
  • Patent Document 1 JP-A-63-93766
  • Patent Document 2 JP-A-1 283270
  • Patent Document 3 JP-A-8-208613
  • Patent Document 4 JP-A-10-95772
  • Patent Document 5 JP-A-1283270
  • an object of the present invention is to provide a pyridylmethyl 2,6-dichloroisonicotinate derivative exhibiting an excellent effect on plant disease control, a method for producing the same, and an agricultural and horticultural disease control agent.
  • a substituted pyridylmethyl amide derivative of 6-cyclomouth isonicotinic acid is a novel conjugate, and surprisingly, by introducing a substituent into the pyridine ring, it can be used as an agricultural and horticultural disease controlling agent. It has been found that the present invention exerts more excellent effects, and the present invention has been completed.
  • a first gist of the present invention is pyridylmethyl 2,6-dicyclomouth isonicotinate represented by the following formula (I). Derivatives exist.
  • A represents an oxygen atom or a nitrogen atom that is unsubstituted or substituted with a lower alkyl group.
  • Q represents a pyridine ring group of Ql, Q2 or Q3.
  • X represents Represents a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group, a cyano group, a hydroxyl group, a phenoxy group, a phenyl group or a halogen atom, and m is an integer of 0 to 4. When m is 2 or more, X may be the same or different.
  • a second gist of the present invention is to provide a 2,6-dichloroisonicotinic acid derivative represented by the following formula (II) and a substituted pyridylmethyl alcohol, amine or a substituted pyridylmethyl alcohol represented by the following formula ( ⁇ )
  • the present invention relates to a method for producing a pyridylmethyl 2,6-dicyclomouth isonicotinate derivative represented by the formula (I), characterized by reacting with a halide.
  • A represents an oxygen atom or a nitrogen atom which is unsubstituted or substituted with a lower alkyl group.
  • Q represents a pyridine ring group of Ql, Q2 or Q3.
  • X represents Represents a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group, a cyano group, a hydroxyl group, a phenoxy group, a phenyl group or a halogen atom, and m is an integer of 0 to 4.
  • X may be the same or different Y represents a hydroxyl group, a chlorine atom or a nitrogen atom which is unsubstituted or substituted by a lower alkyl group; Represents a hydroxyl group, a chlorine atom, or a nitrogen atom that is unsubstituted or substituted with a lower alkyl group.
  • a third gist of the present invention resides in an agricultural and horticultural disease control agent containing a pyridylmethyl 2,6-dichloromouth isonicotinate derivative represented by the above formula (I) as an active ingredient.
  • the pyridylmethyl 2,6-dicyclomouth isonicotinate derivative of formula (I) can be used as an active ingredient of an agricultural and horticultural disease controlling agent.
  • a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group and a lower alkylthio group usually have 116 carbon atoms, preferably 114 carbon atoms. Is included.
  • the lower alkyl group for X includes a methyl group, an ethyl group, a 1-methylethyl group, a 1,1-dimethylethyl group and an n-propyl group, and the lower alkoxy groups include methoxy, ethoxy, 1-methylethyl group. Tiloxy, 1,1-dimethylethyloxy and propyloxy are mentioned.
  • the lower haloalkyl group is a trifluoromethyl group.
  • the lower haloalkoxy group is a difluoromethoxy group and a trifluorooxy group.
  • Examples include a lomethoxy group and a 2,2,2-trifluoroethoxy group, and examples of the lower alkylthio group include a methylthio group.
  • examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. Preferred integers m are 1 and 2.
  • Examples of the diluent used in the production method described above include the following. Water, formic acid Organic acids such as acetic acid, propionic acid, hydrocarbons such as benzene, toluene, xylene, petroleum ether, pentane, hexane, heptane, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, and methanol Alcohols such as ethanol, isopropanol and t-butanol, ethers such as getyl ether, dimethoxyethane, diisopropyl ether, tetrahydrofuran, diglyme and dioxane, carbon disulfide, acetonitrile, acetone and ethyl acetate; Acetic anhydride, pyridine, dimethylformamide, dimethylacetamide, 1-methyl-2-pyrrolidinone, dimethylsulfoxide, hexamethylphosphoric amide
  • Examples of the base include the following. Alkali metal carbonates such as sodium carbonate, sodium bicarbonate, potassium carbonate and potassium bicarbonate; alkaline earth metal carbonates such as calcium carbonate and barium carbonate; alkalis such as sodium acetate, potassium acetate and sodium propionate Metal carboxylates, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkaline earth metal oxides such as magnesium oxide and calcium oxide, lithium, sodium, potassium, etc.
  • Alkali metal carbonates such as sodium carbonate, sodium bicarbonate, potassium carbonate and potassium bicarbonate
  • alkaline earth metal carbonates such as calcium carbonate and barium carbonate
  • alkalis such as sodium acetate, potassium acetate and sodium propionate
  • Metal carboxylates alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkaline earth metal oxides such as magnesium oxide and calcium oxide, lithium, sodium, potassium, etc.
  • Alkali earth metals such as magnesium, magnesium, etc., alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide, alkali metal hydrides such as sodium hydride, potassium hydride, methyllithium, ethyllithium, etc. n-Butyllithium, ferric Organic metal compounds of alkali metals, such as organic compounds, organic Grignard reagents such as methyl magnesium iodide, ethyl magnesium bromide, n-butyl magnesium bromide, organic metal compounds of alkali metals or Grignard reagents, and copper (I) salts.
  • alkali earth metals such as magnesium, magnesium, etc.
  • alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide
  • alkali metal hydrides such as sodium hydride, potassium hydride, methyllithium, ethyllith
  • alkali metal amides such as lithium disopropylamide, aqueous ammonia, ammonium hydroxides such as benzyltrimethylammonium hydroxide, tetramethylammonium hydroxide, and methylammonium.
  • organic amines such as min, ethylamine, n-propylamine, benzylamine, ethanolamine, dimethylamine, benzylmethylamine, dibenzylamine, triethylamine, triethanolamine, pyridine and the like.
  • the pyridylmethyl derivative of 2,6-dichloroisonicotinic acid (I) is obtained by substituting the derivative of 2,6-dichloroisonicotinic acid ( ⁇ ) with the substituted pyridylmethyl alcohol, substituted pyridylmethylamine or substituted pyridylmethylamine of the formula (III).
  • Pyridylmethylnodride can be advantageously produced in a diluent in the presence of a base .
  • a compound prepared by dissolving a 2,6-dichloroisonicotinic acid derivative (II) in the above-mentioned diluent is added, if necessary, to a compound represented by the formula Ability to convert substituted pyridylmethyl alcohol, substituted pyridylmethylamine or substituted pyridylmethyl halide of (III) by 0.5 to 1.5 equivalents, or conversely, substituted pyridylmethyl alcohol, substituted pyridylmethylamine or substituted of formula (III) It is advisable to react a 2,6-dichloroisonicotinic acid derivative (II) with a base dissolved in a solution of pyridylmethyl halide in a diluent.
  • 2,6-dichloroisonicotinic acid pyridylmethyl derivative (I) is a 2,6-dichloroisonicotinic acid derivative (II) and a substituted pyridylmethyl alcohol of formula (III), a substituted pyridylmethylamine or a substituted pyridylmethylnodide.
  • a substituted pyridylmethyl alcohol of formula (III) a substituted pyridylmethylamine or a substituted pyridylmethylnodide.
  • 2,3-dichloroisonicotinic acid derivative (II) is dissolved in the above-mentioned diluent, and if necessary, In the presence of a condensing agent such as hexylcarposimide or 1-ethyl-3- (3-dimethylaminopropyl) carposimide, the substituted pyridylmethyl alcohol, substituted pyridylmethylamine or substituted pyridylmethylhalide of the formula (III) is usually added in a concentration of 0.5.
  • a condensing agent such as hexylcarposimide or 1-ethyl-3- (3-dimethylaminopropyl) carposimide
  • the reaction temperature at this time may be any temperature up to the freezing point and boiling point of the diluent as a solvent, but it is practically preferable to carry out the reaction at a temperature in the range of -10 to 100 ° C. .
  • the reaction time is in the range of 0.5 to 10 hours, and it is desirable to carry out the reaction with stirring.
  • pyridylmethyl 2,6-dichloroisonicotinate derivative (I) After drying, the solvent is distilled off under reduced pressure, and the obtained residue is purified to give pyridylmethyl 2,6-dichloroisonicotinate derivative (I).
  • the purification treatment can be performed by recrystallization or silica gel column chromatography.
  • the pyridylmethyl 2,6-dichloroisonicotinate derivative of the formula (I) according to the present invention exhibits a controlling effect on a wide range of plant diseases described below.
  • rice blast (Pyricularia oryzae), rice sesame leaf blight (Cochliobolus miyabeanus), rice is a power seedling;) hei I ⁇ KGibberella fujikuroi), ⁇ , J ⁇ ⁇ (Helminthosporium sigmoideum), ⁇ Rhizoctonia solanu, 3 ⁇ from various crops (Botrytis cinerea), sclerotium; ⁇ ⁇ (Sclerotinia sclerotiorum), Sui power vine damage 1 Fusarium oxysporum f.sp.niveum (1) Fusanum oxysporum f.sp.cucumerinum, P.
  • anthracnose fungus (Colletotnchum lagenarium, Anzai brown ⁇ ⁇ K and ercospora beticola, Cercospora 31 ⁇ (Cercospora ki uchn) ), Peach J fire disease! 3 ⁇ 4 (bclerotinia cinerea, alternata, maili), Nan black 3 ⁇ 4 ⁇ (Alternaria alternata (kikuchiana)), grape rot (Glomerella cingulata, cucumber and disease (Pseudoperonosora cubensis), tomato throw (Phytophthra infestans), cucumber gray rot (Phytophthora capsici) , Rice seedling blight fungus (Pythium
  • E. coli scab Erisiphe graminis f. sp. tntic.
  • the compound in order to apply the pyridylmethyl 2,6-dichloroisonicotinate derivative (I) of the present invention as an agricultural and horticultural disease controlling agent as described above, the compound can be used as it is, but usually, the compound is used as a preparation. It is formulated and used in various forms such as powders, wettable powders, granules and emulsions together with adjuvants. At this time, one or more pyridylmethyl 2,6-dichloroisonicotinate derivatives (I) are usually 0.1 to 95% by weight, preferably 0.5 to 90% by weight, more preferably 0.5 to 90% by weight in the preparation. Preferably, it is formulated so as to contain 2 to 70% by weight.
  • Examples of the carriers, diluents, and surfactants used as formulation aids include talc, kaolin, benite, diatomaceous earth, white carbon, and clay as solid carriers, and liquid diluents. Examples thereof include water, xylene, toluene, benzene, cyclohexane, cyclohexanone, dimethyl sulfoxide, dimethylformamide, alcohol and the like.
  • Emulsifiers which can be used properly depending on their effect include polyoxyethylene alkylaryl ether and polyoxyethylene sorbitan monolaurate.
  • Dispersants such as ligne sulfonate and dibutyl naphthalene sulfonate
  • Examples of the wetting agent include alkyl sulfonates and alkyl phenyl sulfonates.
  • the above-mentioned preparations include those used as they are and those used after being diluted to a predetermined concentration with a diluent such as water.
  • concentration of the compound of the present invention when diluted and used is preferably in the range of 0.001 to 1.0%.
  • the amount of the compound of the present invention is preferably 20 to 5000 g, more preferably 50 to 100 g per hectare of an agricultural or horticultural land such as a field, a field, an orchard, and a greenhouse. Since the concentration and amount of use vary depending on the dosage form, time of use, method of use, place of use, target crop, and the like, it is of course possible to increase or decrease the amount without being limited to the above range.
  • the compounds of the present invention can be used in combination with other active ingredients, for example, fungicides, insecticides, acaricides, herbicides.
  • the compounds of I4, I6, I9, 1-11 and I13 were synthesized by the operation according to Production Example 18 above.
  • the melting points and NMR data for these compounds are shown in Table 12 along with the data for the compounds 1-1, I5, I7, I8, I10 and I12.
  • Test example 1
  • Transplant rice (variety: Koshihikari) at the 3 leaf stage into a 1/1 Oo Wagner pot filled with paddy soil, and after 20-35 days, the granules adjusted according to Formulation Example 3 have a predetermined concentration (500g / 10a) The surface was applied as shown. Ten to twenty days after the chemical treatment, a spore suspension of the rice blast fungus formed on the rice disease was sprayed and inoculated, and kept at high humidity in a vinyl tunnel in a glass greenhouse.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention a trait à des dérivés pyridylméthyles de l'acide 2,6-dichloroisonicotinique de formule (I) : dans laquelle : A est oxygène ou azote substitué ou non substitué avec alkyle inférieur ; Q est un groupe cyclique pyridine de formule (Q1), (Q2) ou (Q3) ; X est alkyle inférieur, haloalkyle inférieur, alcoxy inférieur, haloalcoxy inférieur, alkylthio inférieur, cyano, hydroxy, phényle, phénoxy, ou halogéno ; et m est un nombre entier de 0 à 4, à condition que lorsque m est égal ou supérieur à 2, les X peuvent être identiques les uns aux autres ou différents les uns des autres. L'invention a également trait à leur procédé de production, et à des agents de lutte contre des maladies pour utilisation en agriculture et en horticulture Le dérivés de formule (I) présentent des effets de contrôle efficace contre des maladies végétales.
PCT/JP2005/000211 2004-01-13 2005-01-12 Derives pyridylmethyles de l'acide 2,6-dichloroisonicotinique, leur procede de production, et agents de lutte contre des maladies pour utilisation en agriculture et en horticulture Ceased WO2005068430A1 (fr)

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JP2005517028A JP4706482B2 (ja) 2004-01-13 2005-01-12 ２，６−ジクロロイソニコチン酸ピリジルメチル誘導体、その製造方法および農園芸用病害防除剤

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012053186A1 (fr) * 2010-10-18 2012-04-26 Raqualia Pharma Inc. Dérivés d'arylamide en tant qu'agents bloquants de ttx-s
WO2014006945A1 (fr) * 2012-07-04 2014-01-09 アグロカネショウ株式会社 Dérivé d'ester d'acide 2-aminonicotinique et bactéricide le contenant comme principe actif
WO2017126197A1 (fr) * 2016-01-21 2017-07-27 アグロカネショウ株式会社 Procédé de production de dérivé d'ester benzylique d'acide 2-aminonicotinique
WO2018169038A1 (fr) 2017-03-17 2018-09-20 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 Agent de lutte contre les maladies des plantes
WO2020054531A1 (fr) * 2018-09-14 2020-03-19 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 Agent de lutte contre les maladies des plantes

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JPH01283270A (ja) * 1988-03-25 1989-11-14 Ciba Geigy Ag 植物を病気から保護するための組成物
JPH08208615A (ja) * 1995-02-03 1996-08-13 Dainippon Ink & Chem Inc ２，６−ジクロロイソニコチン酸ベンジルアミド誘導体及び植物病害防除剤
WO2002022583A2 (fr) * 2000-09-18 2002-03-21 E. I. Du Pont De Nemours And Company Pyridinyl-amides et pyridinyl-imides utilisés comme fongicides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01283270A (ja) * 1988-03-25 1989-11-14 Ciba Geigy Ag 植物を病気から保護するための組成物
JPH08208615A (ja) * 1995-02-03 1996-08-13 Dainippon Ink & Chem Inc ２，６−ジクロロイソニコチン酸ベンジルアミド誘導体及び植物病害防除剤
WO2002022583A2 (fr) * 2000-09-18 2002-03-21 E. I. Du Pont De Nemours And Company Pyridinyl-amides et pyridinyl-imides utilisés comme fongicides

Non-Patent Citations (1)

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Title
DATABASE CHEMCATS [online] 24 February 2005 (2005-02-24), XP002986320, Database accession no. 2004:533092 *

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9302991B2 (en) 2010-10-18 2016-04-05 Raqualia Pharma Inc. Arylamide derivatives as TTX-S blockers
WO2012053186A1 (fr) * 2010-10-18 2012-04-26 Raqualia Pharma Inc. Dérivés d'arylamide en tant qu'agents bloquants de ttx-s
JP2014177450A (ja) * 2010-10-18 2014-09-25 Raqualia Pharma Inc Ｔｔｘ−ｓ遮断薬としてのアリールアミド誘導体
JPWO2014006945A1 (ja) * 2012-07-04 2016-06-02 アグロカネショウ株式会社 ２−アミノニコチン酸エステル誘導体およびこれを有効成分とする殺菌剤
CN104520273B (zh) * 2012-07-04 2016-08-24 阿格罗－金正株式会社 2-氨基烟酸酯衍生物及以其为有效成分的灭菌剂
US9096528B2 (en) 2012-07-04 2015-08-04 Agro-Kanesho Co., Ltd. 2-aminonicotinic acid ester derivative and bactericide containing same as active ingredient
AU2013284775B2 (en) * 2012-07-04 2015-09-17 Agro-Kanesho Co., Ltd. 2-aminonicotinic acid ester derivative and bactericide containing same as active ingredient
CN104520273A (zh) * 2012-07-04 2015-04-15 阿格罗－金正株式会社 2-氨基烟酸酯衍生物及以其为有效成分的灭菌剂
WO2014006945A1 (fr) * 2012-07-04 2014-01-09 アグロカネショウ株式会社 Dérivé d'ester d'acide 2-aminonicotinique et bactéricide le contenant comme principe actif
KR101629767B1 (ko) 2012-07-04 2016-06-13 아구로카네쇼 가부시키가이샤 2-아미노니코틴산에스테르 유도체 및 이를 유효 성분으로 하는 살균제
KR20150042781A (ko) * 2012-07-04 2015-04-21 아구로카네쇼 가부시키가이샤 2-아미노니코틴산에스테르 유도체 및 이를 유효 성분으로 하는 살균제
RU2599725C2 (ru) * 2012-07-04 2016-10-10 Агро-Канесо Ко., Лтд. Производное соединение сложного эфира 2-аминоникотиновой кислоты и бактерицид, содержащий то же самое в качестве активного ингредиента
WO2017126197A1 (fr) * 2016-01-21 2017-07-27 アグロカネショウ株式会社 Procédé de production de dérivé d'ester benzylique d'acide 2-aminonicotinique
JPWO2017126197A1 (ja) * 2016-01-21 2018-11-15 アグロカネショウ株式会社 ２−アミノニコチン酸ベンジルエステル誘導体の製造方法
RU2702121C1 (ru) * 2016-01-21 2019-10-04 Агро-Канесо Ко., Лтд. Способ получения производного бензилового эфира 2-аминоникотиновой кислоты
WO2018169038A1 (fr) 2017-03-17 2018-09-20 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 Agent de lutte contre les maladies des plantes
KR20190136016A (ko) 2017-03-17 2019-12-09 메이지 세이카 파루마 가부시키가이샤 식물병 방제제
US12156523B2 (en) 2017-03-17 2024-12-03 Mmag Co., Ltd. Plant disease control agent
WO2020054531A1 (fr) * 2018-09-14 2020-03-19 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 Agent de lutte contre les maladies des plantes

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JPWO2005068430A1 (ja) 2008-04-24

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