WO2002094766A1 - Derive de phtalamide, insecticide agricole et horticole et son utilisation - Google Patents

Derive de phtalamide, insecticide agricole et horticole et son utilisation Download PDF

Info

Publication number
WO2002094766A1
WO2002094766A1 PCT/JP2002/004744 JP0204744W WO02094766A1 WO 2002094766 A1 WO2002094766 A1 WO 2002094766A1 JP 0204744 W JP0204744 W JP 0204744W WO 02094766 A1 WO02094766 A1 WO 02094766A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
halo
alkyl
alkoxy
nono
Prior art date
Application number
PCT/JP2002/004744
Other languages
English (en)
Japanese (ja)
Inventor
Makoto Goto
Toshiaki Shimizu
Masanori Tohnishi
Akira Seo
Masayuki Morimoto
Shinsuke Fujioka
Original Assignee
Nihon Nohyaku Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nihon Nohyaku Co., Ltd. filed Critical Nihon Nohyaku Co., Ltd.
Publication of WO2002094766A1 publication Critical patent/WO2002094766A1/fr

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/72Nitrogen atoms
    • C07D213/75Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/30Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/45Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
    • C07C311/46Y being a hydrogen or a carbon atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/51Y being a hydrogen or a carbon atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/26Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/28Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/26Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C317/34Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
    • C07C317/38Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
    • C07C317/40Y being a hydrogen or a carbon atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/31Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/33Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring
    • C07C323/35Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group
    • C07C323/36Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group the sulfur atom of the sulfide group being further bound to an acyclic carbon atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/43Y being a hetero atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32One oxygen, sulfur or nitrogen atom
    • C07D239/42One nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D241/00Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
    • C07D241/20Nitrogen atoms

Definitions

  • the present invention relates to a phthalamide derivative, an agricultural and horticultural insecticide containing the compound as an active ingredient, and a method for using the same.
  • Japanese Patent Application Laid-Open No. 60-82247 discloses that compounds similar to the phthalamide derivatives of the present invention are useful as fungicides for agricultural and horticultural use.
  • No. 4,636,863 discloses that compounds similar to the phthalamide derivatives of the present invention are useful as herbicides and plant growth regulators.
  • the present inventors have conducted intensive studies to develop a novel agricultural and horticultural drug.As a result, the phthalamide derivative represented by the general formula (I) of the present invention is a novel compound not described in the literature, The present invention has been found to be useful as an agent and has completed the present invention.
  • the present invention provides a compound represented by the general formula (I)
  • R 1 and R 2 may be the same or different; a hydrogen atom, a —c 6 alkyl group, a c 3 -alkyl group, c. -c 6 alkynyl group, c 3 -cycloalkyl group, c 6 arco Carboxymethyl - c 6 alkyl group, c r c 6 alkylthio c 6 alkyl group, Fueeru c r c 4 Al Kill group or the same or different and may a halogen atom, Shiano group, a nitro group,
  • R 3 represents a halogen atom, a cyano group, a —C 6 alkyl group, a halo Cfc 6 alkyl group, a c 6 alkoxy group, a nodro c 6 alkoxy group having a group on the ring.
  • the condensed rings may be the same or different, and include a halogen atom, a d-C 6 alkyl group, a nodro-C 6 alkyl group, and a Alkoxy group, a halo c 6 alkoxy group, - c 6 Arukiruchio group, halo c r c 6 alkylthio group, ( ⁇ C 6 alkyl sulfide El group, halo ( ⁇ al Kino less Luffy El group, C r C 6 ⁇ Rukirusuruho - Le It may have one or more substituents selected from a group or a halo-Ce alkylsulfol group Q 1 and Q 2 may be the same or different and represent a carbon atom or a nitrogen
  • X 1 is a halogen atom, a nitro group, an amino group, Shiano groups, C ⁇ c 6 alkyl group, Nono b - c 6 alkyl group, c 2 -c 6 alkenyl group, halo c 2 - c 6 alkenyl group, c 2 - c 6 alkynyl group, halo C 2 -C 6 alkyl group, -Cg alkoxy group, nodro C Factory c 6 alkoxy group, C 6 alkylthio group, halo-Cs alkylthio group, C 6 alkylsulfinyl group, halo c r c 6 ⁇ Roh gravel Angeles sulfide El group, a c r c 6 alkylsulfonyl group or halo c r c 6 ⁇ Rukirusuruhoeru group.
  • X 2 is hydrogen atom A, halogen atom, nitro group, amino
  • A is A 1 to A 4 No
  • Y may be the same or different, and a halogen atom, a cyano group, a nitro group,
  • R It is hydrogen, C r C 6 alkyl group, Nono port c r c 6 alkyl group, c 3 - c 6 alkenyl group, halo c 3 - c 6 Aruke - le group, c 3 - c 6 alkynyl group, a halo c 3 -c 6 alkynyl group, c 3 -c 6 cycloalkyl group,-c 6 alkoxy-c 6 alkyl group, cr c 6 alkylthio cr c fi alkyl group, phenyl group, same or different Connexion is good, a halogen atom, arsenic Dorokishi group, an amino group, a mercapto group, Shiano group, a nitro group, - c 6 alkyl group, halo c r c 6 alkyl group, - c 6 alkoxy group, Nono b c - c 6 alk
  • C 6 alkylsulfonyl group halo C Factory A substituted phenyl-alkyl group having at least one substituent selected from a C 6 alkylsulfonyl group or a c 6 alkoxycarbonyl group on the ring, a heterocyclic group, identical or different Halogen atom, hydroxy group, amino group, mecapto group, cyano group, nitro group, alkyl group, halo C 6 alkyl group, C factory C 6 alkoxy group, halo (: wide C 6 alkoxy group, C 6 Alkylthio group, nodro (Factory alkylthio group, cc 6 alkylsnolefinyl group, halo-c 6 alkylsulfuryl group, (Factory C 6 alkylsulfonyl group, halo-Cg alkylsulfonyl group or (wide alkoxycarbonyl substituted double heterocyclic group having one or more
  • R 8 is a hydrogen atom, a hydroxy group, an amino group, a —Cs alkyl group, a no, a C r C 6 alkyl group, a C 3 -C 6 alkenyl group, a halo C 3 —.
  • two adjacent Y's on the aromatic ring can form a condensed ring together, and the condensed rings may be the same or different, and include a halogen atom, a C 6 alkyl group, and a halo-C 6 alkyl.
  • n shows the integer of 0-3. ). And a method for using the same.
  • the phthalamide derivative of the present invention is suitable for controlling various pests such as agriculture, forestry, horticulture, stored grain pests, sanitary pests and nematodes, and exhibits excellent control activity.
  • halogen atom represents a chlorine atom, bromine atom, iodine atom or fluorine atom
  • n ⁇ represents normal
  • s ⁇ represents secondary.
  • t- represents tertiary
  • i- represents iso
  • C 6 alkyl represents, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, i —A linear or branched alkyl group having 1 to 6 carbon atoms such as -butyl, s-butyl, t-butyl, n-pentyl, neopentyl, n-hexyl, etc.
  • -C 6 haloalkyl Means the number of linear or branched carbon atoms substituted by one or more halogen atoms which may be the same or different:!
  • alkyl groups such as trifluoromethyl group, difluoromethyl group, perfluoroethyl group, norfluoroisopropyl group, chloromethyl group, bromomethyl group, 1-bromoethyl group, 2,3-dibromopropyl
  • Examples of such a group include “-Cg / alkylene”, which means a straight chain or a branched chain such as methylene, ethylene, propylene, trimethylene, dimethinolemethylene, tetramethylene, isoptylene, dimethylethylene, and hexamethylene.
  • Heterocyclic group refers to a 5- or 6-membered heterocyclic group having one or more heteroatoms selected from an oxygen atom, a sulfur atom or a nitrogen atom, such as a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group , Furyl, tetrahydrofuryl, chloro, tetrahydrochel, tetrahydrovillal, tetrahydrothioviranyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, imidazolyl Group, triazolyl group, pyrazolyl group and the like.
  • fused ring examples include naphthalene, tetrahydronaphthalene, indene, indane, quinoline, quinazoline, indo / le, indoline, chroman, isochroman, benzodioxane, benzodioxo / le, benzofuran, dihydrobenzofuran Benzothiophene, benzothiophene, dihydric benzothiazole, benzoxazole, benzothiazoles, benzimidazole, indazole and the like. .
  • R 1 and R 2 preferably represent a hydrogen atom or a (: alkyl group, particularly preferably a hydrogen atom.
  • R 3 preferably represents a halogen atom or a CrC 4 alkyl group.
  • IT preferably represents a halo C 6 alkyl group or a halo-C 6 anoreoxy group
  • R 5 preferably represents a hydrogen atom or a halogen atom
  • X 1 preferably represents a halogen atom
  • X 2 preferably represents a hydrogen atom.
  • Q 1 and Q 2 each preferably represent a carbon atom, A preferably represents A 1 or A 2, and Y preferably represents -alkylthio group, (1 ⁇ 2-C 6 alkylthio C 6 alkyl group, Represents a bamoyl group or a sulfamoyl group, and n preferably represents 1 or 2.
  • the phthalamide derivative represented by the general formula (I) of the present invention can be produced, for example, by the production method shown below.
  • a phthalic acid hydride derivative represented by the general formula (II-1) Reacting a phthalic acid hydride derivative represented by the general formula (II-1) with an amine derivative represented by the general formula (II I-1) in an inert solvent in the presence or absence of a base
  • an isimide derivative represented by the general formula (IV-1) which is isolated or not isolated and represented by the general formula (V) in the presence or absence of an acid or a base.
  • the phthalamide derivative represented by the general formula (I-1) can be produced by reacting the phthalamide derivative with an amine derivative in an inert solvent.
  • A represents A 1 to A 4 and ⁇ in 81 to 4 represents -G-R 7 , G represents -SO- or 1 S 0 2- compounds shown represents the Y guard E- R 6, E is - in a conventional manner a compound showing a S-, for example, m- black port perbenzoic acid, carrying out the oxidation reaction with an oxidizing agent such as hydrogen peroxide Can be manufactured. 1-1.
  • the inert solvent used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene, methylene chloride, chloroform, and carbon tetrachloride.
  • Halogenated hydrocarbons such as benzene, dichlorobenzene, etc., chain or cyclic ethers such as getyl ether, dioxane, tetrahydrofuran, etc., esters such as ethyl acetate, dimethyl
  • amides such as formamide and dimethylacetamide
  • acids such as acetic acid
  • inert solvents such as dimethyl sulfoxide and 1,3-dimethyl-2 midazolidinone.
  • the reaction can be carried out at a temperature ranging from room temperature to the boiling point of the inert solvent to be used.
  • the reaction time is not fixed depending on the reaction scale and the reaction temperature, but may be within a range from several minutes to 48 hours.
  • the desired product may be isolated from the reaction system containing the desired product by a conventional method. If necessary, the desired product can be produced by recrystallization, purification by column chromatography, or the like. It is also possible to provide the next reaction step without isolation from the reaction system.
  • the phthalic halides represented by the general formula (II-1) are Re ag e n t f o r
  • Examples of the acid that can be used in this reaction include organic acids such as acetic acid and trifluoroacetic acid, and inorganic acids such as hydrochloric acid and sulfuric acid.
  • the amount of the acid used is phthalisoimide represented by the general formula (IV-1). What is necessary is just to select and use suitably from the range of a catalyst amount or excess mol with respect to a derivative.
  • Examples of the base include organic bases such as triethylamine and pyridine, carbonated sodium carbonate, sodium hydrogencarbonate, sodium carbonate, and sodium hydroxide.
  • Inorganic bases such as lithium can be exemplified, and the amount of the inorganic base may be appropriately selected from the range of a catalytic amount or an excess molar amount with respect to the phthalisoimide derivative represented by the general formula (IV-1). .
  • the inert solvents exemplified in (1-1) can be mentioned.
  • the reactants may be used in an equimolar amount, but the amines represented by the general formula (V) may be used in excess.
  • the reaction can be carried out at a temperature from room temperature to the boiling point of the inert solvent to be used.
  • the reaction time is not fixed depending on the reaction scale and the reaction temperature, but may be within a range from several minutes to 48 hours.
  • the desired product may be isolated from the reaction system containing the desired product by a conventional method. If necessary, the desired product can be produced by recrystallization, purification by column chromatography, or the like.
  • the compound represented by the general formula (VI-2) is obtained.
  • the phthalamic acid derivative (VI-2) in which R 1 represents a hydrogen atom is obtained by isolating or not isolating the phthalamic acid derivative (VI-2) in the presence of a base
  • a condensation reaction is carried out in the absence of a condensing agent in the presence of a condensing agent in an inert solvent to obtain an isoimide derivative represented by the general formula (IV-2).
  • the isoimide derivative (IV-2) is isolated or isolated.
  • a phthalamide derivative represented by the general formula CO is R 1 Of phthalamic acid derivative (VI-2) showing a substituent other than a hydrogen atom
  • the compound represented by the general formula (I) is condensed with an amine derivative represented by the general formula (III-2) in an inert solvent in the presence or absence of a base in the presence of a condensing agent.
  • a phthalamide derivative can be produced.
  • a condensation reaction is carried out in the presence or absence of a condensing agent in the presence of a condensing agent in an inert solvent to obtain an isoimide derivative represented by the general formula (IV-1), and isolating the isoimide derivative (IV-1) Phthalamide derivative represented by the general formula (I) by reacting the phthalamide derivative represented by the general formula (V) in the presence of an inert solvent without isolation or isolation.
  • R 3 is phthalamate derivatives showing a substituent other than a hydrogen atom - if (VI 1), the presence of a base
  • the phthalamide derivative represented by the general formula (I) can be produced by condensing with an amine derivative represented by the general formula (V) in an inert solvent in the absence of a condensing agent. it can.
  • A represents Al to A4, when showing the 1 input 4 ⁇ is _ G-R 7 in, G is - SO- or - S0 2 -
  • 2- General formula (II-2) ⁇ General formula (VI-1) or General formula (VI-2)
  • This reaction can be carried out in the same manner as in the production method (1_2) to produce the desired product.
  • phthalic anhydride derivatives represented by the general formula (I 1-2) are described in J. Org. Chem., _52_, 129 (1987), J. Am. Chem. Soc., 51, 1865 (1929), and J. Am. Chem. Soc., 63, 1542 (1941).
  • the inert solvent used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include halogenation such as methylene chloride, chloropho / rem, and carbon tetrachloride.
  • the solvent include chain or cyclic ethers such as hydrocarbons, getyl ether, dioxane, and tetrahydrofuran; and inert solvents such as nitriles such as acetonitrile. These inert solvents may be used alone or in combination of two or more. It can be mixed and used.
  • the condensing agent used in this reaction may be any one used in the usual amide production, such as Mukaiyama reagent (2-chloro-N-methylpyridinium iodide), DCC (1,3-dicyclopentadiene) Hexyl carbodiinide), CDI (carboediimidazole), DEPC (getyl cyanophosphate) and the like can be exemplified.
  • the amount of use is represented by the general formula (IV-1) or (IV-2).
  • the phthalamides to be used may be appropriately selected and used in the range of equimolar to excess molar.
  • Examples of the base that can be used in this reaction include organic bases such as triethylamine and pyridine, and inorganic bases such as potassium carbonate.
  • the amount of the base can be represented by the general formula (IV-1) or the general formula (IV-1).
  • the phthalamide represented by IV-2) may be appropriately selected and used in the range of equimolar to excess molar.
  • the reaction can be carried out at a temperature ranging from 0 ° C. to the boiling point of the inert solvent to be used.
  • the reaction time is not fixed depending on the reaction scale and the reaction temperature, but may be carried out within a range from several minutes to 48 hours.
  • the desired product may be isolated from the reaction system containing the desired product by a conventional method, and the desired product may be produced by recrystallization, column chromatography or the like, if necessary.
  • This reaction can be carried out, for example, according to the method described in Med. Chem., 10, 982 (1 967) to produce the desired product.
  • This reaction can be carried out in the same manner as in the production method (1-2) to produce the desired product.
  • Examples of typical compounds of the phthalamide derivatives represented by the general formula (I) below in Table 1 The present invention is not limited to these.
  • physical properties indicate melting point ° C or properties
  • Me represents a methyl group
  • E t represents an ethyl group
  • Bu represents a butyl group
  • Ph represents a phenyl group
  • Py r represents a pyridyl group
  • Thz represents a thiazolyl group.
  • the agricultural and horticultural insecticide containing the phthalamide derivative represented by the general formula (I) of the present invention as an active ingredient is useful for various agricultural, forestry, horticultural, and grain pests that damage rice, fruit trees, vegetables, other crops, flowers and the like. It is suitable for controlling pests such as sanitary pests and nematodes.
  • apple pests Adoxophyes orana fasciata
  • cyano pests Adoxophyes sp.
  • Apple plums Grapholita inopinata
  • pears Grapholita molesta
  • Mameshin iga Leguminivora glycinivorella
  • Kunodomaki Olethreutes mori
  • Tyanohosoga Caloptilia thevivora
  • Apple hosoga Caloptilia zachrysa
  • Nemonhosoga Physicalllonorycter ringoniella
  • Ootano Koga Heliothis sp.
  • Kodlinga Laspey resia pomonella
  • Kona Moth Plutella xylostella
  • Apple turtle ArArgyresthia conjugella
  • Momosingiga Carposina niponensis
  • Nikame 77
  • Cro suppressalis Cobb (Cnaphalocrocis medinalis) N )
  • Sanka San
  • the agricultural and horticultural insecticide comprising a phthalamide derivative represented by the general formula (I) of the present invention as an active ingredient is useful for the above-mentioned pests that damage paddy crops, field crops, fruit trees, vegetables, other crops, flowers and the like. It has a remarkable control effect, and is suitable for paddy fields, fields, fruit trees, wild vegetables, other crops, flowers, etc. before or at the time when the pest is confirmed
  • the desired effects of the agricultural and horticultural insecticide of the present invention can be obtained by treating seeds, paddy water, foliage or soil.
  • the agricultural and horticultural insecticide of the present invention is generally used after being formulated into a convenient form in accordance with a conventional method for agricultural chemical formulation.
  • the phthalamide derivatives represented by the general formula (I) may be dissolved, separated, suspended, mixed, mixed in a suitable inert carrier or, if necessary, in an appropriate ratio together with an auxiliary. Impregnated, adsorbed or adhered to the appropriate dosage form, such as a suspending agent,? Tablets, liquids, wettable powders, wettable powders, granules, powders, tablets, packs and the like.
  • the inert carrier that can be used in the present invention may be either solid or liquid. Examples of the material that can be a solid carrier include soybean flour, cereal flour, wood flour, bark flour, saw flour, and tobacco stem flour.
  • Materials that can be liquid carriers are selected from those that themselves have a solvent function and those that can disperse the active ingredient compounds with the aid of auxiliaries without having a solvent function.
  • Examples thereof include the following carriers, which may be used alone or in the form of a mixture of two or more. Examples thereof include water, alcohols (for example, methanol, ethanol, isopropanol, butanol, ethylene glycol).
  • Ketones for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.
  • ethers for example, ethyl ether, dioxane, cenote sonolev, dipropyl ether, tetrahydrofuran) Etc.
  • aliphatic hydrocarbons eg kerosene, mineral oil, etc.
  • aromatic hydrocarbons for example, benzene, toluene, xylene, sonoleventnaphtha, anolequinolenaphthalene, etc.
  • halogenated hydrocarbons for example, dichloroethane, chloroform, carbon tetrachloride, chlorinated benzene, etc.
  • esters for example, acetic acid
  • Examples of the other adjuvants include the following representative adjuvants. These adjuvants are used according to the purpose, and may be used alone or in combination of two or more kinds. In some cases, it is possible to use no auxiliaries at all.
  • Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and / or wetting active compounds, such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene higher grades.
  • Fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylaryl sulfonate, naphthalene sulfonic acid condensate, ligone sulfonate, higher alcohol sulfate ester, etc. Can be exemplified.
  • adjuvants for the purpose of stabilizing the dispersion of the active ingredient compound, sticking and bonding or binding,
  • adjuvants such as casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum arabic, polyvinyl alcohol, pine oil, bran oil, bentonite, and lignin sulfonate. Can also be used.
  • the following adjuvants can be used to improve the flowability of the solid product.
  • a scavenger such as wax, stearate, alkyl phosphate, etc.
  • auxiliary agents such as, for example, naphthalenesulfonic acid condensate and condensed phosphate can be used.
  • an antifoaming agent for example, an auxiliary agent such as silicone oil can be used.
  • an auxiliary agent such as silicone oil
  • preservatives 1,2-benzisothiazolin-3-one, parachlorometa-xylenol, butyl para-oxybenzoate and the like can also be added.
  • a functional spreading agent such as a metabolic decomposition inhibitor such as piperonyl butoxide, an antifreezing agent such as propylene glycol, an antioxidant such as BHT, an ultraviolet absorber, and the like. Additives can also be added.
  • the compounding ratio of the active ingredient compound can be adjusted as needed, and the agricultural and horticultural insecticide in 100 parts by weight may be appropriately selected and used from the range of 0.01 to 90 parts by weight, For example, when it is used as a powder or granules, it is 0.01 to 50% by weight, and when it is used as an emulsion or a wettable powder, it is also 0.01 to 50% by weight. / 0 is appropriate.
  • the agricultural and horticultural insecticide of the present invention is used for controlling various pests, or in an appropriately diluted or suspended form with water or the like, in an amount effective for controlling the pests, in which the occurrence of the pest is predicted. Alternatively, it may be used by applying it to a place where generation is not preferable.
  • the amount of the agricultural and horticultural pesticide used in the present invention depends on various factors, such as the purpose, the target pest, the growth status of the crop, the pest occurrence tendency, the weather, the environmental conditions, the dosage form, the application method, the application place, and the application time.
  • the active ingredient compound may be appropriately selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, per 10 ares as the active ingredient compound.
  • the agricultural and horticultural insecticide of the present invention further includes other agricultural and horticultural insecticides, acaricides, nematicides, and the like for the purpose of controlling pests to be controlled, extending the suitable period of control, or reducing the amount of medicine. It can be used in combination with fungicides, biological pesticides, etc. It can be used as a mixture with herbicides, plant growth regulators, and fertilizers.
  • Other agricultural and horticultural insecticides, acaricides, and nematicides used for this purpose include, for example, ethion, triclonolefone, methamidophos, acephate, dichlorvos, mevinphos, monocrotophos, malathion, dimethoate, hoslemothion, mechanorebam.
  • Pamidthione Thiometone, Disulfoton, Oxideprofos, Nared, Methylparathion, Hue-Throthione, Cyanophos, Propaphos, Fentione, Proti-Shophos, Prophenophos, Isofenphos, Temephos, Fentate, Dimethinolevinphos, Chronolefclovinhos , Phoxime, isoxathion, pyraclophos, methidathion, clopyridifos, chlorpyrifos' methyl, pyridafenthion, diazinon, pyrimid Phosmethyl, hosalon, phosmet, dioxabenzophos, quinanolephos, terbufos, etoprophos, dyssaphos, mesulfenphos, DPS (NK-0 795), phosphocarp, fenamiphos, isoamidoho,
  • Trin Trin, cypermethrin, a / refascinolemetrin, cyhalothrin, lambda 'sinopurintrin, denoletametrin, aclinatrin, fenvalerate, esfenvalerate, flucitrinate, fluvalinate, cycloprothrin, etofenprox, hanole Fenprox, Silabrofen, F / Recitrinate, Fulvalinate, Mesomyl, Oxamil, Zodicalp, Aldicarp, Arani-Lup, Cartap, Mettlecalp, Kilica / Rev, Proboxur, Fenoxy-Lub, Fenobu-Lup, Echioffen-Lev Huenotiokanoreb, Bifenazate, BP MC, Kyrubaliril, Pirimicarb, Carbofuran, Carbosulfan, Fratiocanoleb, Benfracarb, Al
  • Agricultural and horticultural fungicides include, for example, sulfur, lime-sulfur mixtures, basic copper sulfate, iprobenphos, edifenphos, turquoise phos'methyl, chiram, polycarbamate, zineb, manzep, manco.
  • herbicides include, for example, glyphosate, sulfosate, gnorefosinate, vialaphos, ptamiphos, esprocanoleb, Sulfocalp, Benchiokarb, Pilipuchikarp, Ashram, Linuron, Daimlon, Bensnoreflon-Mechinore, Cycrosnorefamron, Synosnoreflon, Pyrazosulfronethyl, Azimus / Refron, Imazos noreflon, teninoleculol, aralkrol, pretilacronole, clomeprop, etobenzanide, mefenacet, pendimethalin, bifenox, asifnoleofen, lactofen, cyhalofop-butyl, ioxynil, promobutide, aroxydim, aroxydim Do, Indanofan, Pyrazo
  • biological pesticides for example, nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), insect box virus (Entomopox virus, EPV), etc .; Monoclosporium 'Fimatonogam' (Monacrosporium phymatophagum); Steinernema carpocapsae; Steinernema kushidai; Trichoderma, a microbial pesticide used as an insecticide ⁇ Trichoderma lignorum, Agrobacterium radiobactor, non-pathogenic Erwinia carovora, Erwinia carotovora, Killing of Bacillus subtilis A similar effect can be expected by mixing and using a microbial pesticide used as a fungicide, a biological pesticide used as a herbicide such as Zanthomonas campestris (Xanthomonas campestris), and the like.
  • NPV nuclear polyhedrosis virus
  • biopesticides for example, encarsia bees (Encarsia formosa), koreman ablanoch (Aphidius colemani), shoku power, tamae (Aphidoletes aphidimyza), isahia himekono, ji (Diglyphus isaea), Chile; v Natural enemy organisms such as vegetative mites (Phytoseiulus persimilis), kucumeri risukaburidani (Amblyseius cucumeris), Namihimenokekamushi (Orius sauteri), etc.
  • Diatomaceous earth powder 15 parts The above is uniformly mixed and pulverized to obtain a powder.
  • the above is uniformly mixed and pulverized to obtain a wettable powder.
  • Test example 1 Insecticidal test against Japanese moth (Plutella xylostella)
  • the adult Chinese moth is released to Chinese cabbage seedlings to lay eggs, and two days after the release, the Chinese cabbage seedlings with spawning eggs are diluted to 50 ppm with a drug containing the compounds listed in Tables 1 to 3 as active ingredients. It was immersed in the solution for about 30 seconds, air-dried, and allowed to stand in a constant temperature room at 25 ° C. Six days after the immersion in the drug solution, the number of hatching insects was investigated, the mortality was calculated by the following formula, and the judgment was made according to the following criteria. 1 ward 1 0 3 triple
  • Test example 2 Insecticidal test against Anemonium japonicus (Adoxophyes sp.)
  • Drugs containing the compounds listed in Tables 1 to 3 as active ingredients were diluted to 50 ppm. After immersing the leaf in a chemical solution for about 30 seconds, air-dry it, put it in a plastic dish with a diameter of 9 cm, inoculate the larvae of Antrodia japonicus, and leave it in a constant temperature room at 25 ° C and 70% humidity. . Eight days after the inoculation, the number of live and dead insects was investigated, the mortality was calculated according to the following formula, and the judgment was made according to the judgment criteria of Test Example 1. 1 ward 1 0 3 triple

Abstract

L'invention concerne un dérivé de phtalamide représenté par la formule générale (I) (dans laquelle R1 et R2 peuvent être identiques ou différents et représentent chacun hydrogène, alkyle C¿1?-C6, etc.; R?3¿ représente halogéno, cyano, etc.; R4 représente halogéno, haloalkyle C¿1?-C6, etc.; R?5¿ représente hydrogène, halogéno, etc.; Q1 et Q2 peuvent être identiques ou différents et représentent chacun carbone ou azote; X1 représente halogéno, nitro, etc. et X2 représente hydrogène, halogéno, etc., à condition que X1 et X2 en combinaison puissent former un cycle fusionné; et A représente n'importe lequel de A1 à A4); ainsi qu'un insecticide agricole ou horticole contenant le composé en tant qu'ingrédient actif.
PCT/JP2002/004744 2001-05-18 2002-05-16 Derive de phtalamide, insecticide agricole et horticole et son utilisation WO2002094766A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2001149407 2001-05-18
JP2001-149407 2001-05-18

Publications (1)

Publication Number Publication Date
WO2002094766A1 true WO2002094766A1 (fr) 2002-11-28

Family

ID=18994583

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2002/004744 WO2002094766A1 (fr) 2001-05-18 2002-05-16 Derive de phtalamide, insecticide agricole et horticole et son utilisation

Country Status (1)

Country Link
WO (1) WO2002094766A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004018415A1 (fr) * 2002-08-26 2004-03-04 Nihon Nohyaku Co., Ltd. Derives sulfonamide, insecticides a usage agricole et horticole, et leurs applications
WO2006024523A1 (fr) * 2004-09-01 2006-03-09 Syngenta Participation Ag Dérivés de phtalamide s'utilisant comme insecticides
EP1974606A2 (fr) 2004-07-20 2008-10-01 Bayer CropScience AG Insecticides sélectifs à base de phtalamides et de phytoprotecteurs
US7432281B2 (en) 2003-10-07 2008-10-07 Renovis, Inc. Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same
US7576099B2 (en) 2005-02-28 2009-08-18 Renovis, Inc. Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same
US7795303B2 (en) 2003-07-08 2010-09-14 Bayer Cropscience Ag Active agents combination exhibiting insecticidal and acaricide properties
US8143193B2 (en) 2003-07-08 2012-03-27 Bayer Cropscience Ag Active agents combination exhibiting insecticidal and acaricide properties
US10391094B2 (en) 2010-11-07 2019-08-27 Impact Biomedicines, Inc. Compositions and methods for treating myelofibrosis
US10752594B2 (en) 2013-03-14 2020-08-25 Sumitomo Dainippon Pharma Oncology, Inc. JAK1 and ALK2 inhibitors and methods for their use
US11040038B2 (en) 2018-07-26 2021-06-22 Sumitomo Dainippon Pharma Oncology, Inc. Methods for treating diseases associated with abnormal ACVR1 expression and ACVR1 inhibitors for use in the same

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4842209B1 (fr) * 1970-10-12 1973-12-11
EP0919542A2 (fr) * 1997-11-25 1999-06-02 Nihon Nohyaku Co., Ltd. Derives diamide de l'acide phthalique, insecticides pour l'agriculture et horticulture, et leur utilisation

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4842209B1 (fr) * 1970-10-12 1973-12-11
EP0919542A2 (fr) * 1997-11-25 1999-06-02 Nihon Nohyaku Co., Ltd. Derives diamide de l'acide phthalique, insecticides pour l'agriculture et horticulture, et leur utilisation

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7161032B2 (en) 2002-08-26 2007-01-09 Nihon Nohyaku Co., Ltd. Sulfonamide derivatives, insecticides for agricultural and horticultural use, and usage thereof
WO2004018415A1 (fr) * 2002-08-26 2004-03-04 Nihon Nohyaku Co., Ltd. Derives sulfonamide, insecticides a usage agricole et horticole, et leurs applications
US7795303B2 (en) 2003-07-08 2010-09-14 Bayer Cropscience Ag Active agents combination exhibiting insecticidal and acaricide properties
US8143193B2 (en) 2003-07-08 2012-03-27 Bayer Cropscience Ag Active agents combination exhibiting insecticidal and acaricide properties
US7432281B2 (en) 2003-10-07 2008-10-07 Renovis, Inc. Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same
EP1974606A2 (fr) 2004-07-20 2008-10-01 Bayer CropScience AG Insecticides sélectifs à base de phtalamides et de phytoprotecteurs
US8017632B2 (en) 2004-07-20 2011-09-13 Bayer Cropscience Ag Selective insecticides based on haloalkylnicotinic acid derivatives, anthranilic acid diamides, or phthalic acid diamides and safeners
US8685985B2 (en) 2004-07-20 2014-04-01 Bayer Cropscience Ag Selective insecticides based on anthranilic acid diamides and safeners
US8841328B2 (en) 2004-07-20 2014-09-23 Bayer Cropscience Ag Selective insecticides based on anthranilic acid diamides and safeners
WO2006024523A1 (fr) * 2004-09-01 2006-03-09 Syngenta Participation Ag Dérivés de phtalamide s'utilisant comme insecticides
US7576099B2 (en) 2005-02-28 2009-08-18 Renovis, Inc. Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same
US10391094B2 (en) 2010-11-07 2019-08-27 Impact Biomedicines, Inc. Compositions and methods for treating myelofibrosis
US10752594B2 (en) 2013-03-14 2020-08-25 Sumitomo Dainippon Pharma Oncology, Inc. JAK1 and ALK2 inhibitors and methods for their use
US11040038B2 (en) 2018-07-26 2021-06-22 Sumitomo Dainippon Pharma Oncology, Inc. Methods for treating diseases associated with abnormal ACVR1 expression and ACVR1 inhibitors for use in the same

Similar Documents

Publication Publication Date Title
JP4355991B2 (ja) 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
JP5311072B2 (ja) 複素環アミン誘導体
KR100523718B1 (ko) 방향족 디아미드 유도체, 농원예용 약제 및 이의 사용방법
JPWO2008044713A1 (ja) 置換ピリジン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
US20040097595A1 (en) Phthalamide derivatives, insecticides for agricultural and horticultural use and method for application thereof
WO2002094766A1 (fr) Derive de phtalamide, insecticide agricole et horticole et son utilisation
JP4993049B2 (ja) 芳香族ジアミ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
JP4671079B2 (ja) フタラミド誘導体、その中間体及び農園芸用殺虫剤並びにその使用方法
JP4853759B2 (ja) 置換ピラジンカルボン酸アニリド誘導体又はその塩類、その中間体及び農園芸用薬剤並びにその使用方法
JP5077523B2 (ja) 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、その中間体及び農園芸用薬剤並びにその使用方法
US20040116299A1 (en) Phthalamide derivates, insecticides for agricultural and horticultural use and method for application thereof
WO2001000599A1 (fr) Derives de benzamide, insecticides pour l&#39;agriculture/l&#39;horticulture, et utilisation
JP4798410B2 (ja) ベンズアミド誘導体及び農園芸用殺虫剤並びにその使用方法
WO2003093228A1 (fr) Derive de phtalamide, insecticide agricole ou horticole, et son procede d&#39;utilisation
JP4217948B2 (ja) 置換芳香族アミド誘導体、その中間体及び農園芸用殺虫剤並びにその使用方法
JP4706810B2 (ja) ピリジン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
JP2001240580A (ja) 芳香族ジアミド誘導体及び農園芸用薬剤並びにその使用方法
JP4389243B2 (ja) フタルアミド誘導体及び農園芸用殺虫剤並びにその使用方法
JP4217947B2 (ja) フタルアミド誘導体及び農園芸用殺虫剤並びにその使用方法
JP2002326980A (ja) ジアミド誘導体及び農園芸用薬剤並びにその使用方法
JP2805256B2 (ja) ヒドラジンカルボキサミド誘導体及びその製造方法、その用途ならびにその使用方法
JPWO2008053991A1 (ja) 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
JP2003012636A (ja) フタルアミド誘導体及び農園芸用殺虫剤並びにその使用方法
KR20050018812A (ko) 프탈아미드 유도체, 농원예용 살충제 및 그의 용도

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS KE KG KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SD SE SG SI SK SL TJ TM TN TR TT TZ UA UG US UZ VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

122 Ep: pct application non-entry in european phase