WO2008053991A1 - Dérivé de pyrazolecarboxanilide substitué ou son sel, produit chimique agricole ou horticole, et son procédé d'utilisation - Google Patents

Dérivé de pyrazolecarboxanilide substitué ou son sel, produit chimique agricole ou horticole, et son procédé d'utilisation Download PDF

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Publication number
WO2008053991A1
WO2008053991A1 PCT/JP2007/071403 JP2007071403W WO2008053991A1 WO 2008053991 A1 WO2008053991 A1 WO 2008053991A1 JP 2007071403 W JP2007071403 W JP 2007071403W WO 2008053991 A1 WO2008053991 A1 WO 2008053991A1
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group
halo
alkyl
alkoxy
same
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PCT/JP2007/071403
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English (en)
Japanese (ja)
Inventor
Kozo Machiya
Yoshihiro Matsuzaki
Takashi Furuya
Akiyuki Suwa
Noriaki Yasokawa
Shinsuke Fujioka
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Nihon Nohyaku Co., Ltd.
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Priority to JP2008542197A priority Critical patent/JPWO2008053991A1/ja
Publication of WO2008053991A1 publication Critical patent/WO2008053991A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • 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

Definitions

  • the present invention relates to a substituted pyrazole carboxylic acid anilide derivative, an agricultural and horticultural agent containing the compound as an active ingredient, particularly an agricultural or horticultural insecticide or acaricide, and a method of using the same.
  • substituted pyrazolecarboxylic acid amide derivatives similar to the present invention are useful as agricultural and horticultural insecticides, fungicides or acaricides (see, for example, Patent Documents 1 and 2).
  • Patent Documents 1 and 2 disclose substituted pyrazole carboxylic acid anilide derivatives as part of a wide range of substituted anilides.
  • the 1-position substituent of pyrazole is limited to a hydrogen atom, an alkyl group, a haloalkyl group, and a phenyl group, and an acyl group at the 1-position of pyrazole described in the present invention.
  • substituted pyrazole carboxylic acid anilide derivatives into which a substituent such as an alkoxyalkyl group is introduced.
  • Patent Document 1 Japanese Patent Laid-Open No. 2003-48878
  • Patent Document 2 JP 2004-189738 A
  • the substituted pyrazole carboxylic acid anilide derivatives represented by the general formula (I) are novel compounds not described in the literature, and are found to be useful as agricultural and horticultural agents, in particular, agricultural and horticultural insecticides, fungicides or acaricides.
  • the present invention has been completed.
  • a substituted phenoxycarbonyl group having one or more substituents selected on the ring (49a) a phenoxy C 1 -C alkylcarbonyl group,
  • R 2 is
  • n an integer of 1 to 4.
  • X may be the same or different
  • a substituted phenyl group having one or more substituents selected on the ring having one or more substituents selected on the ring
  • Y 2 can be the same or different
  • n 1 or 2.
  • Z represents an oxygen atom or a sulfur atom.
  • R 1 is
  • a substituted pyrazole carboxylic acid anilide derivative or a salt thereof according to [1] or [2] above;
  • n 1
  • a sulfonyl group (n) a mono-C-Canolenoquinolamino group, (0) di-C-C-a which may be the same or different
  • An agricultural and horticultural agent characterized by treating an effective amount of the agricultural and horticultural agent according to [8] or [9] above with a target plant or soil in order to control pests from useful plants. how to use;
  • c 1 -c alkynyl and the like have the following meanings.
  • Halogen atom refers to a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.
  • C 1 -C alkyl refers to a linear or branched alkyl having 1 to 6 carbon atoms.
  • C 1 -C alkyl refers to a linear or branched alkyl having 1 to 8 carbon atoms.
  • methinore, ethinore, n-propinole, i-propinore, n-butinore, i-butinore, s-butinore, t-butinore, n-pentinore isopentinole, neopentinole, t-pentinole, 2-methylbutyl, n-hexyl, n-hexyl 1, 3-Dimethylol
  • examples include butyl, n-heptyl, n-octyl, 2-ethylhexyl and the like.
  • C_C alkyl represents a linear or branched alkyl having 1 to 10 carbon atoms
  • C 1 -C cycloalkyl refers to a cyclic alkyl having 3 to 6 carbon atoms, for example
  • C 1 -C alkoxy is an alkyl moiety having 1 straight or branched carbon atoms.
  • C 1 -C alkoxy is an alkoxy whose alkyl moiety is the above “C 1 -C alkyl”.
  • methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, n-pentyloxy, isopentyl / reoxy, nepentyl / reoxy, t-pench / le examples include the following: xylose, 2-methy / lebutoxy, 1-ethy / reproboxy, hexyloxy, 2-ethylbutoxy.
  • C 1 -C alkoxy is an alkyl moiety having 1 straight or branched carbon atoms.
  • C_C alkoxy means that the alkyl moiety has 1 straight or branched carbon atom.
  • C_C alkoxy means that the alkyl moiety has 1 straight or branched carbon atom.
  • alkoxy which is ⁇ 16 alkyls, for example, methoxy, ethoxy, n-propoxy, i propoxy, n butoxy, isobutoxy, s butoxy, t butoxy, n pentenoreoxy, isopentyloxy, neopentyloxy, t-pentyloxy, 2-methinobutoxy, 1-ethinorepropoxy, hexenole-oxygen, 2-ethinolevoxy, n-heptanoloxy, n-octyloxy, 2-ethylhexyloxy, n-nonyloxy, n-desiloxy, n-undesyloxy / Reoxy, n-tridecyloxy, n-tetradecyloxy, n pentadecyloxy, n-hexadecyloxy, etc.
  • C 1 -C cycloalkoxy refers to a cyclic alkyl group having 3 to 6 carbon atoms.
  • Examples thereof include cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclooctynoleoxy and the like.
  • C 1 -C alkenyl refers to a straight or branched chain having at least one double bond
  • C 1 -C alkenyl refers to a straight or branched chain having at least one double bond.
  • alkenyl having 2 to 8 carbon atoms for example, butle, 1 propenyl, allyl, 1-butur, 2 butur, 3 butur, 2 pentul, 2 methyl-1 propenyl, 2, 4 pentagenyl, 3 Xenyl, 3 heptul, 3-octatur, etc. are listed.
  • C 1 -C alkynyl refers to a straight or branched chain having at least one triple bond
  • Alkynyl having 2 to 6 carbon atoms such as Etul, 2-Probule, 1-Butul, 2 Butur, 3 Butur, 2 Pentur, 3 Hexhur, etc.
  • C-c alkynyl is a straight or branched chain having at least one triple bond
  • An alkynyl having 2 to 6 carbon atoms is exemplified, and examples thereof include ethur, 2 probule, 1-butur, 2 butur, 3 butur, 2 pentur, 3 hexul, 3 heptynyl, and 3-otatur.
  • Heterocycle refers to a 5- or 6-membered heterocyclic group having one or more hetero atoms selected from an oxygen atom, a sulfur atom and a nitrogen atom, and includes, for example, a furyl group, a tetrahydrofuryl group, a thiyl group.
  • Examples include lyl group, isothiazolidinyl group, triazolyl group, triazolidinyl group, oxadiazolyl group, thiadiazolyl group, pyridyl group, pyridine N oxide group, pyrimidinyl group, pyrazyl group, tetrahydrobiranyl group, tetrahydrothiopyranyl group, etc. .
  • fused ring examples include naphthalene, tetrahydronaphthalene, indene, indane, quinoline, quinazoline, indanol, indoline, chroman, isochroman, benzodioxan, benzodioxanol, benzofuran, dihydrobenzofuran, benzothiophene, dihydrin benzothiophene, Benzoxazonore, benzothiazonole, benzimidazole, indazole and the like.
  • X and R 1 are combined to form a ring atom that contains one nitrogen atom in addition to the carbon atom; and !! to two identical or different oxygen atoms, sulfur atoms, and
  • the 5- to 8-membered ring which may have a hetero atom which also has a selected nitrogen atom force includes, for example, pyrrolinole, pyrrolidine, imidazole, imidazolidine, pyrazole, virazolidine, oxazolidine, thiazolidine, isoxazolidine, isothiazolidine , Triazole, triazolidine, piperidin, piperazine, morpholine, Chi-mono monoforin, homopiperidine, homopiperazine, homomonoreforin, homothiomonoreforin, azacyclooctane, 1,4-diazacyclooctane, 1 , 5-diazacyclooctane, 1 other 4-oxacyclooctane
  • C 1 -C:” and “C 2 -C” are carbon such as 2 to 6 carbon atoms and 1 to 10 carbon atoms.
  • halo C 1 -C alkyl one or more halogen atoms which may be the same or different may be used.
  • chloromethinole 2 chloroethinole, 2, 2, 2 trichloroethinole, 3 black mouth propinole, 2 chloro 1 , 1-Dimethylenoreethinole, 1-Bromo 1-Methinoreethinore, Difunoleolometinole, Trifunoleolomethinole, 2, 2, 2-Trifluoroethyl, Perfluoro oral hexyl, etc.
  • Salts of the substituted pyrazole carboxylic acid anilide derivatives represented by the general formula (I) of the present invention include alkali metal (lithium, sodium, potassium, etc.) salts, alkaline earth metals (calcium, magnesium, etc.). Salts, ammonium salts, salts of organic amines (methylamine, triethylamine, diethanolamine, piperidine, pyridine, etc.) or acid addition salts.
  • acid addition salts include acetates, propionates, Carboxylates such as oxalate, trifluoroacetate, benzoate, sulfonates such as methanesulfonate, trifluoromethanesulfonate, p-toluenesulfonate, hydrochloride, sulfate, nitrate, Examples include inorganic acid salts such as carbonates.
  • the substituted pyrazolecarboxylic acid anilide derivative represented by the general formula (I) of the present invention may contain one or more asymmetric centers in the structural formula, and two or more optical isomers may be present. And diastereomers may exist, and the present invention includes all of the optical isomers and mixtures containing them in an arbitrary ratio.
  • substituted pyrazole carboxylic acid anilide derivative represented by the general formula (I) of the present invention may have two kinds of geometric isomers derived from a carbon-carbon double bond in the structural formula.
  • the invention encompasses all geometric isomers and mixtures containing them in any proportion.
  • R 1 is preferably
  • R 2 is preferably
  • X is preferably
  • Particularly preferred is a C 1 -C alkyl group.
  • n is particularly preferably 1.
  • a substituted phenoxycarbonyl group having one or more substituents selected on the ring having one or more substituents selected on the ring,
  • Halo C 1 -C alkyl group
  • n is particularly preferably 2.
  • Z is particularly preferably an oxygen atom.
  • the Q represents a halogen atom.
  • the substituted pyrazole carboxylic acid anilide derivative (I 1) in which Z is an oxygen atom is the 1-position unsubstituted represented by the general formula (III 1).
  • a substituted pyrazole carboxylic acid ester represented by the general formula (III 2) is reacted with a pyrazole carboxylic acid ester derivative represented by the general formula (IV-1) in the presence or absence of a base in an inert solvent.
  • the substituted pyrazole carboxylic acid ester derivative is isolated or hydrolyzed without isolation to obtain a substituted pyrazole carboxylic acid represented by the general formula ( ⁇ -3), and the substituted pyrazole carboxylic acid is isolated.
  • it can be produced by reacting with a substituted aniline derivative represented by the general formula ( ⁇ ) in the presence of a condensing agent, a base and an inert solvent without isolation.
  • the substituted pyrazole carboxylic acid represented by the general formula (III 3) is reacted with a halogenating agent in the presence of an inert solvent to obtain an acid halide represented by the general formula ( ⁇ -4).
  • the acid halide is isolated or not isolated, and reacted with a substituted aniline derivative represented by the general formula (II) in the presence of a base and an inert solvent to give a compound represented by the general formula (I 1).
  • the substituted pyrazole carboxylic acid anilide derivative can be produced.
  • Examples of the base used in this reaction include inorganic bases and organic bases.
  • Examples of inorganic bases include hydroxides of alkali metal atoms such as sodium hydroxide and potassium hydroxide; sodium hydride and potassium hydride.
  • Alkali metal hydrides such as sodium ethoxide, potassium t-butoxide and other alcohols; carbonates such as sodium carbonate, potassium carbonate and sodium bicarbonate; triethylamine, pyridine, 1,8-diazabicyclo
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction, for example, aromatic hydrocarbons such as benzene, toluene and xylene; methylene chloride, black mouth form, Halogenated hydrocarbons such as carbon tetrachloride; Halogenated aromatic hydrocarbons such as black benzene and dichlorobenzene; Chain or cyclic ethers such as jetyl ether, dioxane, and tetrahydrofuran; Ethyl acetate, etc.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • methylene chloride black mouth form
  • Halogenated hydrocarbons such as carbon tetrachloride
  • Halogenated aromatic hydrocarbons such as black benzene and dichlorobenzene
  • Chain or cyclic ethers such as jetyl ether, dioxane, and tetrahydrofuran
  • Esters Amides such as dimethylformamide and dimethylacetamide; Ketones such as acetone and methylethylketone; Aprotic polar solvents such as dimethylsulfoxide and 1,3 dimethyl-2-imidazolidinone
  • inert solvents can be used alone or in combination of two or more.
  • each reactant may be used in an equimolar amount, but any one of the reactants can be used in excess, and the reaction temperature ranges from room temperature to the inert solvent used.
  • the reaction can be performed in the boiling range, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be performed in the range of several minutes to 48 hours.
  • the reaction After completion of the reaction, it can be isolated from the reaction system containing the target compound by conventional methods. If necessary, it can be purified by recrystallization, silica gel column chromatography, etc.
  • the l-position unsubstituted pyrazole carboxylic acid ester derivative represented by the general formula (ml) is known (see, for example, Chem. Ber., 1935 (1913) and Ann., 279, 239 (1894)). It can be produced according to the method described.
  • This reaction can be carried out according to the method described in known literature (for example, see the Chemical Society of Japan, “New Experimental Chemistry Course”, Volume 14 ( ⁇ ), p. 9 31-940, 1977, Maruzen Co., Ltd.). good.
  • This reaction can be carried out according to the method described in known literature (for example, see the Chemical Society of Japan, “Experimental Chemistry Course 4th Edition”, Vol. 22, p. 115-; 127, 1991, Maruzen Co., Ltd.). good.
  • the condensing agent used in this reaction for example cyanophosphonate Jechiru (DEPC), carboxymethyl sulfonyl diimidazole (CDI), 1, 3- dicyclo hexyl Cal positive imide (DCC), black hole carbonate esters, iodide 2-chloro 1
  • Examples include methylpyridinium and the like.
  • Examples of the base used in this reaction include inorganic bases and organic bases.
  • inorganic bases include hydroxides of alkali metal atoms such as sodium hydroxide and potassium hydroxide; sodium hydride and potassium hydride.
  • Alkali metal hydrides such as sodium ethoxide, potassium t-butoxide and other alcohols
  • carbonates such as sodium carbonate, potassium carbonate and sodium bicarbonate
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction, for example, aromatic hydrocarbons such as benzene, toluene and xylene; methylene chloride, black mouth form, Halogenated hydrocarbons such as carbon tetrachloride; Halogenated aromatic hydrocarbons such as black benzene and dichlorobenzene; Chain or cyclic ethers such as jetyl ether, dioxane, and tetrafuran furan; Ethyl acetate, etc.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • methylene chloride black mouth form
  • Halogenated hydrocarbons such as carbon tetrachloride
  • Halogenated aromatic hydrocarbons such as black benzene and dichlorobenzene
  • Chain or cyclic ethers such as jetyl ether, dioxane, and tetrafuran furan
  • Esters include Amides such as dimethylformamide and dimethylacetamide; Ketones such as acetone and methylethylketone; Aprotic polar solvents such as dimethylsulfoxide and 1,3 dimethyl-2-imidazolidinone
  • the inert solvent can be used alone, or two or more of these inert solvents can be used in combination.
  • each reactant may be used in an equimolar amount, but any of the reactants can be used in excess, and the reaction temperature ranges from room temperature to the inert solvent used.
  • the reaction can be carried out in the boiling range, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be carried out in the range of several minutes to 48 hours.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne un dérivé de pyrazolecarboxanilide substitué représenté par la formule générale (I) : (I) {où R1 représente un H, alkyle, alkylcarbonyle, alcénylcarbonyle, cycloalkyle, phénylalkyle (substitué), phénylcarbonyle (substitué), etc.; R2 représente un H, halogéno, alkyle, CN, OH, alcoxy, phénoxy (substitué), phénylthio (substitué), phénylsulfonyle (substitué), etc.; Z représente O ou S; X représentent un H, halogéno, CN, alkyle, etc.; Y1 représente un alkylcarbonyle, cycloalkylcarbonyle, alcoxyalkyle, alcoxycarbonyle, phénoxycarbonyle (substitué), alcoxyalkylcarbonyle, alkylcarbonyloxyalkyle, alkylsulfonyle, phénylsulfonyle (substitué), mono- ou dialkylaminocarbonyle, mono- ou dialkylaminothiocarbonyle, phénylcarbonyle (substitué), phénylalkyle (substitué), dialcoxy(thio)phosphoryle, etc.; Y2 représente un halogéno, CN, NO2, alkyle, phényle (substitué), phénoxy (substitué), etc.; m est égal à 1 ou 2; et n est égal à 1-4} ou un sel du dérivé. On fournit également un produit chimique agricole ou horticole contenant le composé en tant qu'ingrédient actif et un procédé d'utilisation du produit chimique. Avec ce composé, un nouveau produit chimique agricole ou horticole, en particulier un insecticide ou un acaricide, est produit.
PCT/JP2007/071403 2006-11-02 2007-11-02 Dérivé de pyrazolecarboxanilide substitué ou son sel, produit chimique agricole ou horticole, et son procédé d'utilisation WO2008053991A1 (fr)

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JP2008542197A JPWO2008053991A1 (ja) 2006-11-02 2007-11-02 置換ピラゾールカルボン酸アニリド誘導体又はその塩類、及び農園芸用薬剤並びにその使用方法

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8987470B2 (en) 2010-10-27 2015-03-24 Solvay Sa Process for the preparation of pyrazole-4-carboxamides
WO2019224143A1 (fr) 2018-05-24 2019-11-28 Bayer Aktiengesellschaft Combinaisons de substances actives à propriétés insecticides, nématicides et acaricides

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001064258A (ja) * 1999-06-24 2001-03-13 Nippon Nohyaku Co Ltd 複素環ジカルボン酸ジアミド誘導体及び農園芸用殺虫剤並びにその使用方法
JP2003048878A (ja) * 2001-05-31 2003-02-21 Nippon Nohyaku Co Ltd 置換アニリド誘導体、その中間体及び農園芸用薬剤並びにその使用方法
JP2004189738A (ja) * 2002-11-29 2004-07-08 Nippon Nohyaku Co Ltd 置換アニリド誘導体、その中間体及び農園芸用薬剤並びにその使用方法
WO2005004606A2 (fr) * 2003-07-10 2005-01-20 Bayer Cropscience Ag Pyridinylanilides
WO2005074686A1 (fr) * 2004-02-06 2005-08-18 Bayer Cropscience Aktiengesellschaft Derives de n-(2-(hydroxymethyl)phenyl)-1h-pyrazolo-4-carboxamide et composes apparentes utilises comme substances actives microbicides dans la protection phytosanitaire et la protection des materiaux
WO2007020986A1 (fr) * 2005-08-12 2007-02-22 Nihon Nohyaku Co., Ltd. Dérivé anilide d'acide pyrazolecarboxylique substitué ou son sel, son intermédiaire, agent pour utilisation horticole et agricole, et son utilisation

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001064258A (ja) * 1999-06-24 2001-03-13 Nippon Nohyaku Co Ltd 複素環ジカルボン酸ジアミド誘導体及び農園芸用殺虫剤並びにその使用方法
JP2003048878A (ja) * 2001-05-31 2003-02-21 Nippon Nohyaku Co Ltd 置換アニリド誘導体、その中間体及び農園芸用薬剤並びにその使用方法
JP2004189738A (ja) * 2002-11-29 2004-07-08 Nippon Nohyaku Co Ltd 置換アニリド誘導体、その中間体及び農園芸用薬剤並びにその使用方法
WO2005004606A2 (fr) * 2003-07-10 2005-01-20 Bayer Cropscience Ag Pyridinylanilides
WO2005074686A1 (fr) * 2004-02-06 2005-08-18 Bayer Cropscience Aktiengesellschaft Derives de n-(2-(hydroxymethyl)phenyl)-1h-pyrazolo-4-carboxamide et composes apparentes utilises comme substances actives microbicides dans la protection phytosanitaire et la protection des materiaux
WO2007020986A1 (fr) * 2005-08-12 2007-02-22 Nihon Nohyaku Co., Ltd. Dérivé anilide d'acide pyrazolecarboxylique substitué ou son sel, son intermédiaire, agent pour utilisation horticole et agricole, et son utilisation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8987470B2 (en) 2010-10-27 2015-03-24 Solvay Sa Process for the preparation of pyrazole-4-carboxamides
WO2019224143A1 (fr) 2018-05-24 2019-11-28 Bayer Aktiengesellschaft Combinaisons de substances actives à propriétés insecticides, nématicides et acaricides

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