WO2008062878A1 - Nouveau dérivé de pyrazole, agent de lutte contre des organismes nuisibles et utilisation de l'agent de lutte contre des organismes nuisibles - Google Patents

Nouveau dérivé de pyrazole, agent de lutte contre des organismes nuisibles et utilisation de l'agent de lutte contre des organismes nuisibles Download PDF

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WO2008062878A1
WO2008062878A1 PCT/JP2007/072682 JP2007072682W WO2008062878A1 WO 2008062878 A1 WO2008062878 A1 WO 2008062878A1 JP 2007072682 W JP2007072682 W JP 2007072682W WO 2008062878 A1 WO2008062878 A1 WO 2008062878A1
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group
halo
alkyl
alkoxy
alkylthio
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PCT/JP2007/072682
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English (en)
Japanese (ja)
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Koji Tanaka
Motohiro Hasebe
Nobutaka Kuroki
Akiyuki Suwa
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Nihon Nohyaku Co., Ltd.
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Priority to JP2008545457A priority Critical patent/JP5205274B2/ja
Publication of WO2008062878A1 publication Critical patent/WO2008062878A1/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
    • C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Definitions

  • Novel pyrazole derivatives, pest control agents and methods of use thereof are novel pyrazole derivatives, pest control agents and methods of use thereof
  • the present invention relates to a novel pyrazole derivative, particularly an N-2- (substituted pyrazolyl) ethylcarboxamide derivative or a salt thereof, and a pest control agent, particularly a plant disease control agent or nematicide containing the compound as an active ingredient.
  • the present invention relates to an agent and a method for using the same.
  • Patent Document 1 International Publication No. 2006/108791 Pamphlet
  • Patent Document 2 Pamphlet of International Publication No. 2006/108792
  • N-2- (substituted pyrazolyl) ethylcarboxamide derivatives represented by the general formula (I) of the present invention or salts thereof are implanted. It has been found that it has not only an excellent control effect as a physical disease control agent, but also has an extremely wide bactericidal spectrum and nematicidal activity, and has completed the present invention. That is, this departure Akira
  • R and R may be the same or different
  • R 3 is
  • (2c) (i) pyridyl group, (ii) pyrimidinyl group, (iii) pyrazol group, (iv) pyrazolyl group, (V) furyl group, ( V i) cenyl group, ( V ii) oxazolyl group, (viii) A heterocyclic group selected from an isoxazolyl group, (ix) thiazolyl group, (X) isothiazolyl group, and (xi) a thiadiazolyl group.
  • X may be the same or different (Id) a halogen atom
  • (20d) may be the same or different (i) (C C) alkyl group, (ii) halo (C C) alkyl
  • a substituted piperidino group having one or more substituents having one or more substituents
  • (22d) may be the same or different, (0 halogen atom, (ii) cyano group, (iii) (C—C) alkyl
  • (24d) may be the same or different, (0 halogen atom, (ii) cyano group, (iii) (C—C) alkyl (Iv) a halo (CC) alkyl group, (v) a (C—C) alkoxy group, and (vi) a halo (C
  • n an integer of 0 to 5.
  • n is an integer of 2 to 5
  • two adjacent Xs are joined together.
  • ⁇ 2 and ⁇ 3 may be the same or different
  • (23e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) (C—C) alkyl
  • a substituted phenyl group having one or more substituents having one or more substituents
  • (25e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) (C—C) alkyl
  • (27e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) (C—C) alkyl
  • (32e) may be the same or different, (i) halogen atom, (ii) cyano group, (iii) (C C) alkyl
  • a substituted phenylthio group having:
  • (34e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) (C—C) alkyl
  • (36e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) (C—C) alkyl
  • (39e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) (C—C) alkyl
  • [0011] is a (2a) (C—C) alkyl group
  • R 2 is (la) a hydrogen atom
  • R 3 is (lb) hydrogen atom
  • Ar is a (lc) phenyl group
  • X may be the same or different
  • (20d) may be the same or different (i) (C C) alkyl group, (ii) halo (C C) alkyl
  • a substituted piperidino group having one or more substituents having one or more substituents
  • (22d) may be the same or different, (i) halogen atom, (ii) cyano group, (iii) (C C) alkyl
  • (24d) may be the same or different, (i) halogen atom, (ii) cyano group, (iii) (C C) alkyl
  • (26d) may be the same or different, (i) halogen atom, (ii) cyano group, (iii) (C C) alkyl
  • n is an integer from 0 to 3
  • X may be the same or different
  • N-2- (substituted pyrazolyl) ethylcarboxamide derivative or a salt thereof according to [1] or [2] above;
  • ⁇ 2 and ⁇ 3 may be the same or different
  • (23e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) (C—C) alkyl
  • (25e) may be the same or different, (i) halogen atom, (ii) cyano group, (iii) (C—C) alkyl
  • (27e) may be the same or different, (i) halogen atom, (ii) cyano group, (iii) (C—C) alkyl
  • (32e) may be the same or different, (i) halogen atom, (ii) cyano group, (iii) (C C) alkyl
  • a substituted phenylthio group having:
  • (34e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) (C—C) alkyl
  • (36e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) (C—C) alkyl
  • (39e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) (C—C) alkyl
  • a pest control agent comprising as an active ingredient the N-2 (substituted pyrazolyl) ethylcarboxamide derivative or a salt thereof according to any one of [1] to [5] above;
  • R and R may be the same or different.
  • ⁇ 2 and ⁇ 3 may be the same or different
  • (23e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) (C—C) alkyl
  • a substituted phenyl group having one or more substituents having one or more substituents
  • (25e) may be the same or different, (i) halogen atom, (ii) cyano group, (iii) (C—C) alkyl
  • (27e) may be the same or different, (i) halogen atom, (ii) cyano group, (iii) (C—C) alkyl
  • (32e) may be the same or different, (i) halogen atom, (ii) cyano group, (iii) (C C) alkyl
  • a substituted phenylthio group having:
  • (34e) may be the same or different, (i) halogen atom, (ii) cyano group, (iii) (C—C) alkyl
  • (36e) may be the same or different (i) halogen atom, (ii) cyano group, (iii) (C 1 -C 6) alkyl
  • (39e) may be the same or different (i) halogen atom, (ii) cyan group, (iii) (C 1 -C 6) alkyl
  • [lljR 1 is a (C —C) alkyl group
  • R 2 is a hydrogen atom
  • ⁇ 2 and ⁇ 3 may be the same or different
  • (23e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) (C—C) alkyl
  • (25e) may be the same or different, (i) halogen atom, (ii) cyano group, (iii) (C—C) alkyl
  • (27e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) (C—C) alkyl
  • (32e) may be the same or different, (i) halogen atom, (ii) cyano group, (iii) (C C) alkyl
  • a substituted phenylthio group having:
  • (34e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) (C—C) alkyl
  • (36e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) (C—C) alkyl
  • (39e) may be the same or different, (i) halogen atom, (ii) cyano group, (iii) (C—C) alkyl
  • the present invention provides a compound having excellent performance as compared with the prior art, in particular, a low amount of sterilized sputum lamb and nematicidal activity as a plant disease control agent.
  • Halogen atom refers to a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.
  • (C C) alkyl group means, for example, methyl group, ethyl group, normal propyl group, i
  • Linear or branched carbon atom number such as sopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, neopentyl group, and normal hexyl group;!
  • To 6 alkyl groups Indicates.
  • halo (C 1 -C 6) alkyl group is the same or different and may be one or more halogen atoms
  • (C—C) cycloalkyl includes cyclopropyl, cyclobutyl, cyclo A cycloalkyl group having 3 to 6 carbon atoms such as a pentyl group and a cyclohexyl group is shown.
  • (C 1 -C 6) alkoxy group means, for example, methoxy group, ethoxy group, normal propoxy
  • halo (C 1 -C 6) alkoxy group is the same or different and may be one or more halogen atoms
  • (C C) alkylthio group means, for example, methylthio group, ethylthio group, normal group
  • Linear or branched carbon atoms such as propylthio, isopropylthio, normal butylthio, secondary butylthio, tertiary butylthio, normal pentylthio, isopentylthio, normal hexylthio, etc. 1-6 alkylthio groups are shown.
  • halo (C 1 -C 6) alkylthio group is the same or different and may be one or more halogens
  • (C—C 6) alkylsulfinyl group means, for example, methylsulfinyl group, ethyls
  • Norefinyl group normal propyl sulfinyl group, isopropyl sulfinyl group, normal butyl sulfier group, secondary butyl sulfier group, tertiary butyl norpheel group, normal pentyl sulfier group, isopentyl sulfier group, normal hexyl sulfier group Or a straight-chain or branched-chain alkynolesulfier group having 1 to 6 carbon atoms.
  • Halo (C 1 -C 6) alkylsulfier group is the same or different and may be one or more groups Linear or branched alkyls of 1 to 6 carbon atoms substituted by a rogen atom
  • (C-C) alkylsulfonyl group means, for example, methylsulfonyl group, ethylsulfo group
  • Ninole group normal propyl sulfonyl group, isopropyl sulfonyl group, normal butyl sulfonyl group, secondary butyl sulfonyl group, tertiary butyl sulfonyl group, nonolemanolepentinores norehoninore group, isopentinores norehoninore group, nonore manole A straight or branched alkylsulfonyl group having 1 to 6 carbon atoms, such as a hexinolesnoyl group.
  • Halo (C 1 -C 6) alkylsulfonyl group is the same or different and may be one or more groups
  • (C C) alkylcarbonyl group means, for example, methylcarbonyl group (acetyl group)
  • a straight-chain or branched alkyl carbonyl group having 1 to 6 carbon atoms such as an ethylcarbonyl group, a normal propylcarbonyl group, an isopropylcarbonyl group, a normal butylcarbonyl group, and a tertiary butylcarbonyl group.
  • (C C) alkoxycarbonyl group means, for example, methoxycarbonyl group, ethoxycarbonyl
  • a linear or branched alkoxy carbonyl group having 1 to 6 carbon atoms such as a norebonyl group, a normal propoxycarbonyl group, an isopropoxycarbonyl group, a normal butoxycarbonyl group, a tertiary butoxycarbonyl group and the like.
  • (C—C) alkoxymino (C—C) alkyl group means, for example, methoxyiminomethyl
  • CC Straight chain or branched chain alkoxyimino (CC) groups such as a group, ethoxyiminomethyl group, normal propoxyiminomethyl group, isopropoxyiminoethyl group, etc. A norequinole group is shown.
  • (C—C) cycloalkane formed by combining R 1 and R 2 together is cyclopropane
  • the "(C—C) anoalkylene group” includes trimethylene group, tetramethylene group, pentamethylene group.
  • alkylenedioxy group having 1 to 3 carbon atoms such as 2 2 2 2 2 2; and the alkylenedioxy group substituted by one or more halogen atoms, which may be the same or different, such as —O— CF
  • a linear or branched alkylamino group having 16 carbon atoms such as a malpropylamino group, isopropylamino group, butylamino group, pentylamino group, hexylamino group and the like is shown.
  • Di (C—C 6) alkylamino group which may be the same or different” includes, for example, dimethylamino
  • Linear, branched, etc. which may be the same or different, such as N-group, jetylamino group, dinormalpropylamino group, diisopropylamino group, N-methyl-N-ethylamino group, N-methyl-N-isopropylamino group, N-methyl-N-xylamino group, etc.
  • Straight-chain or branched carbon atoms such as a group, ethylamino-carbonyl group, normal propylamino-carbonyl group, isopropylamino-carbonyl group, butylamino-carbonyl group, pentylamino-carbonyl group, hexylamino-carbonyl group, etc.
  • "Di (C-C) alkylamino-carbonyl group which may be the same or different" includes, for example,
  • Heterocycle refers to a 5- or 6-membered heterocyclic group having one or more heteroatoms selected from an oxygen atom, a sulfur atom and a nitrogen atom, for example, a furyl group (1 or 2 Furyl group), tetrahydrofuryl group (1 1- or 2-tetrahydrofuryl group), cenyl group (1 1- or 2-phenyl group), tetrahydrocenyl group (1 1- or 2-tetrahydrocenyl group), pyrrolyl group ( 11-, 2- or 3-pyrrolyl group), pyrrolidinyl group (11, 2- or 3-pyrrolidinyl group), imidazolyl group (11, 2 or 4 imidazolyl group), imidazolidinyl group, pyrazolyl group (11, 3 Or 4 pyrazolyl group), virazolidinyl group, oxazolyl group (2—, 4 1 or 5 oxazolyl group), oxazolidinyl group
  • the heterocyclic group represented by Ar is selected from a pyridyl group, a pyrimidinyl group, a pyradyl group, a pyrazolyl group, a furyl group, a chenyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isooxazolyl group, and a thiadiazolyl group.
  • Expressions such as “(CC)”, “(CC)”, and “(CC)” are carbon atoms of various substituents. Indicates a range of numbers. Further, the above definition can be given for the group to which the above substituent is linked. For example, in the case of “(CC) alkoxy (CC) alkyl group”, linear or branched
  • (C—C) alkoxy (C—C) alkylthio group includes methoxymethyl
  • Thio group 1 1- or 2-methoxyethylthio group, 1 2- or 3-methoxypropylthio group, ethoxymethylthio group, 1 1 or 2 ethoxysylthio group, 1 2 or 3 ethoxypropylthio group, etc. Can be mentioned.
  • N-2 (substituted pyrazolyl) ethyl carboxamide derivatives represented by the general formula (I) N- [2- (3-trifluoromethylenole 5-methoxypyrazole 1-inole) ethyl] 2- Bromobenzamide is excluded from the compounds of the present invention.
  • Examples of the salt of the N-2 (substituted pyrazolyl) ethyl carboxamide derivative represented by the general formula (I) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate, acetic acid, and the like.
  • Organic salts such as salts, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, paratoluenesulfonate, sodium ion, potassium ion, calcium ion, trimethylammonium Exemplify salts with inorganic or organic bases.
  • N-2 (substituted pyrazolyl) ethylcarboxamide derivative represented by the general formula (I) of the present invention may contain one or more asymmetric centers in its structural formula. More than one species of optical isomers and diastereomers may exist, and the present invention includes all of the optical isomers and mixtures containing them in an arbitrary ratio.
  • N-2- (substituted pyrazolyl) ethylcarboxamide derivative represented by the general formula (I) of the present invention has two geometric isomers derived from a carbon-carbon double bond in the structural formula.
  • the present invention includes all the geometric isomers and the mixtures in which they are contained in an arbitrary ratio.
  • N-2 (substituted pyrazolyl) ethylcarboxamide derivative represented by the general formula (I) of the present invention In the body,
  • R 1 and R 2 are preferably
  • R 1 and R 2 are a hydrogen atom, and the (S) isomer that is one of the enantiomers of the optically active substance that is generated as a result is more preferable.
  • R 3 is preferably
  • Ar is N
  • X is preferably
  • (20d) may be the same or different (i) (C C) alkyl group, (ii) halo (C C) alkyl
  • a substituted piperidino group having one or more substituents having one or more substituents
  • (22d) may be the same or different, (i) halogen atom, (ii) cyano group, (iii) (C C) alkyl
  • (24d) may be the same or different, (i) halogen atom, (ii) cyano group, (iii) (C C) alkyl
  • (26d) may be the same or different, (i) halogen atom, (ii) cyano group, (iii) (C C) alkyl
  • X is preferably (Id) a halogen atom
  • n is preferably an integer of 0 to 3, more preferably an integer of 1 to 3.
  • Y 2 and Y 3 are preferably
  • (23e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) (C—C) alkyl
  • (25e) may be the same or different, (i) halogen atom, (ii) cyano group, (iii) (C—C) alkyl
  • (27e) may be the same or different, (i) halogen atom, (ii) cyano group, (iii) (C—C) alkyl
  • (32e) may be the same or different, (i) halogen atom, (ii) cyano group, (iii) (C C) alkyl
  • a substituted phenylthio group having:
  • (34e) may be the same or different (i) halogen atom, (ii) cyano group, (iii) (C 1 -C 6) alkyl
  • (36e) may be the same or different (i) halogen atom, (ii) cyano group, (iii) (C 1 -C 6) alkyl
  • (39e) may be the same or different (i) halogen atom, (ii) cyan group, (iii) (C 1 -C 6) alkyl
  • (23e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) (C—C) alkyl
  • (23e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) (C—C) alkyl
  • N-2 (substituted pyrazolyl) ethylcarboxamide derivative represented by the general formula (I) of the present invention is produced, for example, according to the following production method, but is not limited thereto. Manufacturing method 1
  • the condensing agent used in this reaction for example, decyl cyanophosphate (DEPC), carbonyldiimidazole (CDI), 1,3-dicyclohexylcarbodiimide (DCC), black carbonates, iodine of 2 black 1-methyl pyridinylbenzoyloxy ⁇ beam or the like can be exemplified, the amount of that general formula (pi-1) represented by (hetero) 0.8 moles to 1 with respect to cyclic carboxylic acid It may be used by appropriately selecting from a range of 5 times mole.
  • DEPC decyl cyanophosphate
  • CDI carbonyldiimidazole
  • DCC 1,3-dicyclohexylcarbodiimide
  • black carbonates iodine of 2 black 1-methyl pyridinylbenzoyloxy ⁇ beam or the like
  • Examples of the base include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; acetates such as sodium acetate and potassium acetate; potassium — T Alkali metal alkoxides such as butoxide, sodium methoxide, sodium ethoxide; Triethylamine, diisopropylethylamine, 1,8 diazabicyclo [5.4.0] undec-7 tertiary amine such as pyridine; pyridine And nitrogen-containing aromatic compounds such as dimethylaminopyridine, etc., and the amount used is usually 0.5 with respect to the (hetero) cyclic carboxylic acid represented by the general formula ( ⁇ -1). Used in the range of double mole to 10 moles.
  • inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate
  • acetates such as sodium acetate and potassium acetate
  • 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, 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, 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 examples include esters; amides such as dimethylformamide and dimethylacetamide; ketones such as acetone and methylethyl; and inert solvents such as dimethylol sulfoxide and 1,3-dimethyl-2-imidazolidinone.
  • inert solvents can be used alone or in admixture of two or more.
  • each reactant may be used in an equimolar amount, but any of the reactants can be used in excess.
  • the reaction temperature can be from room temperature to the boiling point of the inert solvent to be used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be in the range of several minutes to 48 hours. After completion of the reaction, it can be isolated from the reaction system containing the target product by a conventional method.
  • the (hetero) cyclic carboxylic acid halide represented by the general formula ( ⁇ -2) is reacted with 2- (substituted pyrazolyl) ethylamine represented by the general formula (III) in the presence of a base and an inert solvent.
  • 2- (substituted pyrazolyl) ethylamine represented by the general formula (III) is reacted with 2- (substituted pyrazolyl) ethylamine represented by the general formula (III) in the presence of a base and an inert solvent.
  • an N-2- (substituted pyrazolyl) ethylcarboxamide derivative of the present invention represented by the general formula (I).
  • Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, and potassium hydrogen carbonate; acetic acid such as sodium acetate and potassium acetate.
  • Salts Potassium-alkali metal alkoxides such as t-butoxide, sodium methoxide, sodium ethoxide; Triethylamine, diisopropenoreethinoleamine, 1,8-diazabicyclo [5.4.0] undec-7-en Tertiary amines: Nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine can be mentioned, and the amount used is a (hetero) cyclic carboxylic acid halogen represented by the general formula ( ⁇ -2). It is usually used in the range of 0.5 to 10 moles per mole of the compound.
  • 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 chlorobenzene and dichlorobenzene; Jetyl ether, Dioxane, Tetrahydride Chain or cyclic ethers such as furan; Esters such as ethyl acetate; Amides such as dimethylformamide and dimethylacetamide; Ketones such as acetone and methylethyl; Dimethylol sulfoxide, 1, 3-dimethyl-2- Inert solvents such as imidazolidinone can be exemplified, and these inert solvents can be used alone or in admixture of two or more.
  • aromatic hydrocarbons such as benzene, toluene and
  • reaction temperature can be from room temperature to the boiling point of the inert solvent to be used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be in the range of several minutes to 48 hours.
  • the target product After completion of the reaction, it can be isolated from the reaction system containing the target product by a conventional method. If necessary, the target product can be manufactured by recrystallization, column chromatography, etc. Manufacturing method 3
  • the aldehyde derivative (VI) is isolated or not isolated and reacted with t-butyl carbazate represented by the formula (VII) in the presence of an inert solvent.
  • VIII) represented by the general formula (IX) by reducing the carbon-nitrogen double bond in the presence of an inert solvent with or without isolating the hydrazone derivative (VIII).
  • the carbazic acid derivative (IX) is isolated as a carbazic acid derivative. Without isolating the t-butoxycarbonyl group in the presence of an inert solvent to obtain a hydrazine derivative represented by the general formula (X), and isolating or isolating the hydrazine derivative (X).
  • N-2- (substituted pyrazolyl) ester of the present invention represented by the general formula (I 1) is reacted with the diketone represented by the general formula (XI) in the presence of an inert solvent.
  • a tilcarboxamide derivative can be produced.
  • This reaction may be performed in the same manner as in production method 2.
  • oxidizing agent examples include manganese dioxide, chromic acid, cerium ammonium nitrate (CAN), silver carbonate, pyridine, anhydrous sulfuric acid, activated DMSO (dimethyl sulfoxide), and the like.
  • Known literature used for the conversion of alcohols to aldehydes or ketones eg, Chemical Society of Japan, “New Experimental Chemistry Course”, 15 (1), p. 71-84, 120-123, 804-843, 923, 1004-1006, 1977, Maruzen Co., Ltd. and Chem. Pharm. Bull., 30 (5), ⁇ 1921 ⁇ ; see 1924 (1982)).
  • This reaction may be carried out according to the method described in known literature (for example, J. Org. Chem., 46, ⁇ 5413-5414 (see 1981).
  • an inert solvent As an inert solvent, the progress of this reaction is remarkably inhibited.
  • methanol, ethanol, propanol, butanol Alcohols such as benzene, toluene, xylene, etc .
  • Halogenated hydrocarbons such as methyl chloride, chloroform, carbon tetrachloride
  • Halogenated aromatic carbon such as chloroform, dichlorobenzene, etc.
  • each reactant may be used in an equimolar amount, but any of the reactants can be used in excess.
  • the reaction temperature can be from room temperature to the boiling point of the inert solvent to be used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be in the range of several minutes to 48 hours.
  • a catalytic amount of acid such as formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, hydrochloric acid, sulfuric acid and the like can be added.
  • the target product After completion of the reaction, it can be isolated from the reaction system containing the target product by a conventional method. If necessary, the target product can be produced by recrystallization, column chromatography, etc.
  • Reducing agents that can be used in this reaction include diborane, borane-THF (tetrahydrofuran) complex, borane-dioxane complex, lithium borohydride, sodium borohydride, lithium aluminum hydride, hydrogen metal catalyst (catalytic hydrogenation; metal Examples of catalysts include Raney Nickel, Noradium, Platinum, Rhodium, etc.
  • hydrazine derivative represented by the general formula (X) is free of hydrochloride, sulfate, nitrate, etc. It can also be isolated as an organic acid salt such as an acid salt, a formate salt, an acetate salt, a trifluoroacetate salt, and a methanesulfonate salt and used for the next reaction.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • examples thereof include alcohols such as methanol, ethanol, propanol, and butanol; aromatic hydrocarbons such as benzene, toluene, and xylene.
  • Halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride; Halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; Chain or cyclic ethers such as jetyl ether, dioxane and tetrahydrofuran Esters such as ethyl acetate; amides such as dimethylformamide and dimethylacetamide; and inert solvents such as 1,3-dimethyl-2-imidazolidinone. Or use with a mixture of two or more.
  • each reactant may be used in an equimolar amount, but any of the reactants can be used in excess.
  • the reaction temperature can be from room temperature to the boiling point of the inert solvent to be used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be in the range of several minutes to 48 hours.
  • a catalytic amount of acid such as formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, hydrochloric acid, sulfuric acid and the like can be added.
  • the target product After completion of the reaction, it can be isolated from the reaction system containing the target product by a conventional method. If necessary, the target product can be produced by recrystallization, column chromatography, etc.
  • the 2- (substituted pyrazolyl) ethylamine represented by the general formula (III), which is an intermediate of the present invention, can be produced, for example, according to the following intermediate production methods 1 to 3.
  • 2- (Substituted pyrazolyl) represented by the general formula ( ⁇ -1) is obtained by Mitsunobu reaction of the ethanolamine represented by the general formula (IV-1) and the pyrazole represented by the general formula (XII). It is represented by the general formula (III), which is an intermediate of the present invention, by deprotecting the Boc group as an ethyl chloride and isolating the carbamate ( ⁇ -1) or without isolating it.
  • 2- (Substituted pyrazolyl) ethylamine can be prepared.
  • This reaction may be performed according to a method described in known literature (for example, see Bull. Chem. Soc. Jpn., 40, p2380 to 2382 (1967)).
  • This reaction may be performed in the same manner as 3-5).
  • L represents a leaving group such as a halogen atom, methanesulfonyloxy group, p-toluenesulfonyloxy group.
  • a compound represented by the general formula (IV-2) and a pyrazole represented by the general formula (XII) are reacted in the presence of a base and an inert solvent to represent the general formula ( ⁇ -1).
  • 2- (Substituted azolinol) ethyl carbamates, and the B oc group is deprotected with or without isolating the carbamates () -1), whereby the intermediate of the present invention is represented by the general formula III))
  • a substituted pyrazolyl) ethylamine can be prepared.
  • This reaction may be carried out according to production method 2.
  • This reaction may be performed in the same manner as 3-5).
  • a haloketone represented by the general formula (XIII) and a pyrazole represented by the general formula (XII) are reacted in the presence of a base and an inert solvent to obtain a virazolyl ketone represented by the general formula (XIV).
  • the pyrazolyl ketones (XIV) are isolated or not isolated, and reacted with methoxyamine in the presence of an inert solvent to obtain oximes represented by the general formula (XV), and the oximes are isolated.
  • 2- (substituted pyrazolyl) ethylamine represented by the general formula (III 2) can be produced by reduction in the presence of an inert solvent without isolation.
  • This reaction may be carried out according to production method 2.
  • This reaction may be carried out in the same manner as 3-3).

Abstract

L'invention concerne un dérivé de N-2-(pyrazolyl substitué)éthylcarboxamide représenté par la formule générale (I) ou un sel de celui-ci. L'invention concerne également un agent de lutte contre des organismes nuisibles comprenant le dérivé ou le sel de celui-ci en tant qu'ingrédient actif. (I) [Dans la formule, R1 et R2 représentent chacun indépendamment un atome d'hydrogène, un groupe alkyle ou similaire; R3 représente un atome d'hydrogène ou similaire; Ar représente un groupe phényle ou similaire; X représente un atome d'halogène, un groupe (halogéno)alkyle, un groupe (halogéno)alcoxy, un groupe (halogéno)alkylthio, un groupe (halogéno)alkylsulfinyle, un groupe (halogéno)alkylsulfonyle, un groupe amino, un groupe pipéridino éventuellement substitué, un groupe phényle éventuellement substitué, un groupe alcoxyiminoalkyle ou similaire; n représente un nombre entier de 0 à 5; et Y1, Y2 et Y3 représentent chacun indépendamment un atome d'hydrogène, un atome d'halogène, un groupe cyano, un groupe (halogéno)alkyle, un groupe alkylcarbonyle, un groupe (halogéno)alcoxy, un groupe alcoxyalkyle, un groupe (halogéno)alkylthio, un groupe phényle éventuellement substitué, un groupe alcoxycarbonyle, un groupe phénylalcoxycarbonyle éventuellement substitué, un groupe alcoxyiminoalkyle, un groupe phényl(alcoxyimino en C1-C6)(alkyle en C1-C6) éventuellement substitué ou similaire].
PCT/JP2007/072682 2006-11-22 2007-11-22 Nouveau dérivé de pyrazole, agent de lutte contre des organismes nuisibles et utilisation de l'agent de lutte contre des organismes nuisibles WO2008062878A1 (fr)

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