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WO2007083411A1 - Composition pesticide contenant un derive de diamine - Google Patents

Composition pesticide contenant un derive de diamine Download PDF

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Publication number
WO2007083411A1
WO2007083411A1 PCT/JP2006/317935 JP2006317935W WO2007083411A1 WO 2007083411 A1 WO2007083411 A1 WO 2007083411A1 JP 2006317935 W JP2006317935 W JP 2006317935W WO 2007083411 A1 WO2007083411 A1 WO 2007083411A1
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group
carbon atoms
ipr
carbon
alkyl
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Japanese (ja)
Inventor
Naofumi Tomura
Natsuko Araki
Hiroshi Ishimoto
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Mitsui Chemicals Inc
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Mitsui Chemicals Inc
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    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring

Definitions

  • the present invention relates to a pest control composition comprising a diamine derivative.
  • WO 0 3 0 0 8 3 7 2 shows control activity only for rice blast
  • the diamine derivative of the compound of the present invention has a broad spectrum of disease control spectrum, and the structure is also disclosed in the publication. It is different from the compounds described in the description. ⁇
  • the second active ingredient in the present invention are each a pesticide manaure (The P e s t i c i c e d e Manu a l
  • Patent Document 1 WO 0 0 3 0 0 8 3 7 2,
  • Non-Patent Document 1 Pesticide Manual (The P e s t i c i d e M a n u a 1 T h i r t e e nt e E d i t i o n 2 2 years) Disclosure of Invention
  • an object of the present invention is to provide a pest control composition for efficiently controlling pests.
  • the present inventors have determined that one or more compounds represented by the general formula (1) and one or more compounds from the group consisting of a fungicide, an insecticide or an acaricide. The present inventors have found that pests can be efficiently controlled by mixing, and have completed the present invention.
  • the present invention is as follows.
  • R 1 is an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or 2 to 6 carbon atoms.
  • R 2 and R 5 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or a cycloalkenyl group having 3 to 6 carbon atoms.
  • R 3 and R 4 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or a cycloalkenyl group having 3 to 6 carbon atoms.
  • R 3 and R 4 may be bonded to each other to form a hydrocarbon ring having 3 to 6 carbon atoms,
  • R 6, R 7, R 8 and R 9 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or the number of carbon atoms.
  • a cycloalkenyl group having 3 to 6 carbon atoms and an alkynyl group having 2 to 6 carbon atoms provided that at least one substituent of R 6, R 7, R 8 and R 9 is an alkyl group having 1 to 6 carbon atoms, carbon
  • RIO is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms.
  • Group represents an acyl group
  • A represents an oxygen atom or a sulfur atom
  • O represents an aryl group or a heterocycle.
  • a pesticide composition characterized by comprising as an active ingredient one or more compounds selected from the group consisting of other fungicides, insecticides, and acaricides. .
  • Bactericides, insecticides, acaricides are triazimephone, hexaconazole, puccinazole, ipconazole, prochloraz, triflumizole, tebuconazol, epoxiconazole, diphenoconazole, funolesilazole, triazimenole, Ciproconazole, Metoconazonole, Funorequinconazonore, Vitalenolanol, Tetraconazonore, Triticonazol, Funoretrifofonore, Pencona Zonole, Giniconazonole, Fenbuconazonore, Microcone Ninore, Himexazonole, Imazalinole, Frametopil, Tifluzamide, Etridazole, Oxispoconazole, Oxyspoconazole fumarate, Azole fungicides such as furazoate, prothioconazole, pyrimidine fungicides
  • R 11 represents an alkyl group having 1 to 6 carbon atoms, an alkyl group having 2 to 6 carbon atoms, an aryl alkyl group or a heterocyclic alkyl group
  • R 12 and R 17 are Each represents a hydrogen atom
  • R 1 3 and R 14 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms
  • R 15 and R 16 each represent a hydrogen atom
  • R 1 8 represents an aryl group or a hetero ring.
  • a compound represented by (This compound is W 02 00 3008 3 7 2, which describes the bactericidal activity and production method. ), Or general formula (6):
  • R 19 is an alkyl group having 1 to 6 carbon atoms substituted with halogen, an alkyl group having 3 to 6 carbon atoms substituted with halogen, or an alkyl group having 2 to 6 carbon atoms substituted with halogen.
  • -R group, R 20 and R 25 each represent a hydrogen atom
  • R 2 1 and R 22 each independently represent a hydrogen atom
  • R 2 3 and R 24 Each represents a hydrogen atom
  • R 26 represents an aryl group or a hetero ring.
  • Pyrethroid insecticides DDVP, sianophos, fenthion, phenylothio , Tetrachlorbinphos, Dimethylvinphos, Propafos, Methylparathion, Temefos, Hoxime, Acephete, Isophenfos, Salicion, DE P, EPN, Ethion, Mecarbam, Pyridafenthion, Diazinon, Pirimiphosmethyl, Etrifos, Isoxathion , Quinalfos, Chlorpyrifosmethyl, Chlorpyrifos, Josaron, Phosmet, Methidathion, Oxidebrophos, Bamidothion, Malathion, Fentoate, Dimethoate, Formothion, Thiometone, Ethylthiomethone, Phosphos, Prophos , Monochrome Tofos, Naredo, Phosthiazeto, Triclonolehon,
  • Bamet insecticides imidacloprid, nitenbiram, acetamiprid, dinotefuran, thiamethoxam, thiacloprid, neonicotinoid insecticides such as clothianidin, bromopropyrate, dichophor, endosulfan, Lindan, etc.
  • Organochlorine pesticides difluvenslon, chlorfluzuron, tefruvenslon, trifunolemuron, funolefuenoxuron, funolecycloxuron, hexafnorem mouth, funolezuron, difenthiuron, nono Insect growth control agents such as kunoreron, nobifremolem, bistriflugone, kuma mafuenozide, norofenozide, methoxifenozide, norephurelon, cyromazine, triazamate, nicotine sulfate, polynactin complex, abamectin, mi Bemectin, Repimectin, BT (Baci lus thuringiens is), Spinosad, Rotenone and other natural insecticides, Cartap, Tiocyclam, Benzenoletap, Pimetrozin, Fiproninole, Buprof
  • R 27 represents a methyl group or a chloro group
  • R 28 represents a methyl group, a chloro group, a bromo group or a cyano group
  • R 29 represents a chloro group, a bromo group, a trifluoromethyl group or a cyanomethoxy group
  • R 30 represents a methyl group or an isopropyl group.
  • R 3 1 represents 1, 1, 1, 2, 3, 3, 3-heptafluoro-2-propyl group or 1, 1, 2, 2, 3, 3, 3_heptafluoro-1-propyl group.
  • the (This compound is described in Japanese Patent Application Laid-Open No. 2001-342 1 86, and describes the insecticidal activity and production method.)
  • X i is a hydrogen atom or a fluorine atom
  • R 3 2 and R 3 3 are a hydrogen atom and an alkyl group having 1 to 4 carbon atoms, respectively
  • Q 2 is a phenyl group or a halogen atom.
  • haloalkylsulfier groups carbon number; ⁇ 3 alkylsulfonyl group, 1 ⁇ 3 carbon haloalkylsulfonyl group, 1 ⁇ 4 carbon alkylamino group, 1 ⁇ 4 carbon dialkylamino group, cyano group, nitro group, hydroxy group, carbon number 1 to 4 alkylcarbonyl groups, carbon number :!
  • a substituted phenyl group having one or more substituents which may be the same or different, selected from an alkylcarbonyloxy group having 4 to 4, an aralkoxycarbonyl group having 1 to 4 carbon atoms, a acetylamino group, and a phenyl group; Or a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, a haloalkenyl group having 2 to 4 carbon atoms, or 2 to 4 carbon atoms.
  • Y 5 may be the same or different, and are a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or 1 to 4 carbon atoms.
  • ⁇ 3 is a 2 to 6 perfluoroalkyl group, 1 to 6 carbon perfluoro Oroarukiruchio group, Pas one full O b alkylsulfinyl groups of from 1 to 6 carbon showed Roh Funoreo port alkylsulfonyl Interview Le group of from 1 to 6 carbon, Upsilon 2, Upsilon 4 is a hydrogen atom, a halogen atom, a carbon Represents an alkyl group of 1 to 4 ) Represented by. (This compound is described in WO 2 005-73 1 65, and describes the insecticidal activity and the production method), or the general formula (10):
  • chi 2 is a hydrogen atom or a fluorine atom
  • R35, R36 are each a hydrogen atom, an alkyl group having 1 to 4 carbon atoms
  • R34 is Kill group having 1 to 6 carbon atoms, carbon atoms
  • R 3 7 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, or 2 to 6 carbon atoms
  • E 2 is an alkylene group having 1 to 4 carbon atoms, an alkenylene group having 2 to 4 carbon atoms, an alkynylene group having 3 to 4 carbon atoms, or 1 to carbon atoms
  • 4 haloalkylene group haloalkylene group having 2 to 4 carbon atoms, haloalkylene group having 3 to 4 carbon atoms
  • R 3 9 is a cycloalkyl group having 3 to 8 carbon atoms, and 3 to 8 carbon atoms
  • halo aralkylsulfonyl group cyano group, nitro group, hydroxyl group, alkyl carbonyl group having 1 to 4 carbon atoms, haloalkyl carbonyl group having 1 to 4 carbon atoms
  • Q 4 represents a haloalkyl group having 1 to 6 carbon atoms, a substituted pyridyl group having one or more substituents selected from a haloalkoxy group having 1 to 6 carbon atoms, a phenyl group, and a tetrahydrofuran group.
  • ⁇ 6 and may be the same or different, halogen atom, carbon number 1
  • 1 to 3 haloalkylthio groups 1 to 3 carbon alkylsulfifer groups, 1 to 3 haloalkinolesnorefiel groups, 1 to 3 alkynolesulfonyl groups, 1 to 3 haloalkyl groups sulfo - group, indicates Shiano group, Upsilon 8 par full O b alkyl group having 2 to 6 carbon atoms, 1 to the number of carbon atoms of 6 Pas - full O b alkylthio group, the number of carbon atoms:! ⁇ 6 perfluoroanoleylsulfinyl group, carbon number :!
  • Pafuruoro alkyl sulfonyl Le group ⁇ 6, ⁇ 7, ⁇ 9 is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms. )
  • the mixed composition of the present invention exerts a remarkable control effect on a plurality of pests exhibiting a pest and a drug resistance, etc., each of which was not able to obtain a sufficient control effect with each single agent, It also has a remarkable control effect against pests that could not be controlled and multiple pests that show drug resistance. Therefore, the pest control composition of the present invention can greatly contribute to labor saving in agriculture.
  • the pest control composition of the present invention is a diamine represented by the following general formula (1). It is characterized by containing as an active ingredient a derivative and one or more compounds selected from the group consisting of other fungicides, insecticides, and acaricides.
  • R 1 is an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or 2 to 6 carbon atoms.
  • R 2 and R 5 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or a cycloalkenyl group having 3 to 6 carbon atoms.
  • R 3 and R 4 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or a cycloalkenyl group having 3 to 6 carbon atoms.
  • R 3 and R 4 may be bonded to each other to form a hydrocarbon ring having 3 to 6 carbon atoms,
  • R 6, R 7, R 8 and R 9 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or 3 carbon atoms.
  • R 10 is a hydrogen atom, an alkylenealkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or 2 to 6 carbon atoms.
  • Qi represents an aryl group or a hetero ring.
  • each substituent is not limited to the following, but typical examples thereof are as follows.
  • examples of typical substituents include the following.
  • examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group, and these may be substituted with a substituent, and have 3 to 6 carbon atoms.
  • examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like.
  • alkenyl group having 2 to 6 carbon atoms examples include A vinyl group, a propenyl group, a butyr group, a pentenyl group, a hexenyl group, etc., which may be substituted by a substituent, and as a cycloalkenyl group having 3 to 6 carbon atoms, cyclopropenyl Examples include a ninore group, a cyclobutenino group, a cyclopentenino group, a cyclohexenyl group, etc., and these may be substituted with a substituent, Examples of the alkynyl group having 2 to 6 primes include ethynyl group, propier group, butur group, pentur group, hexyl group and the like, and these may be substituted with a substituent, and as the aryl group, phenyl Group, naphthyl group, etc., and these may be substituted with a substituent, and as the aryl
  • arylcarbonyl such as alkylcarbonyl group or benzoyl group Bonyl group etc. are mentioned, These may be substituted by the substituent.
  • substituent for the alkyl group having 1 to 6 carbon atoms include an alkyl group such as a methyl group, an ethyl group, a propyl group, or a butyl group, and a cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group.
  • Halogen-substituted alkyl groups such as trifluoromethyl group, difluoromethyl group, bromodifluoromethyl group or trifluoroethyl group, alkoxy groups such as methoxy group, ethoxy group, propoxy group or butoxy group, trifluoromethoxy group Groups, halogen-substituted alkoxy groups such as difluoromethoxy group or trifluoroethoxy group, alkylthio groups such as methylthio group, ethylthio group, propylthio group or ptylthio group, trifluoromethylthio group, difluoromethylthio group or trifluoroethylthio group Alkyl sulfinyl groups such as halogen-substituted anololethio groups, methane sulfiel groups, ethane sulfiel groups, propane sulfinyl groups or butansno refinyl groups
  • substituent for an arylalkyl group having 1 to 6 carbon atoms or a heterocyclic alkyl group having 1 to 6 carbon atoms are alkyl groups such as a methyl group, an ethyl group, a propyl group, or a butyl group.
  • Cyclopropyl group, cyclobutyl group, cyclopentyl group or cyclohexyl A cycloalkyl group such as a syl group, a halogen-substituted alkyl group such as a trifluoromethyl group, a difluoromethyl group, a bromodifluoromethyl group or a trifluoroethyl group, an alkoxy such as a methoxy group, a ethoxy group, a propoxy group or a butoxy group Groups, halogen-substituted alkoxy groups such as trifluoromethoxy group, difluoromethoxy group or trifluoroethoxy group, alkylthio groups such as methylthio group, ethylthio group, propylthio group or butylthio group, trifluoromethylthio group, difluoromethylthio group or Halogen-substituted alkylthio groups such as a
  • Non-substituted guanolequinol groups such as alkylsulfinyl groups such as nsunorefinyl group or butansnorefinyl group, trifluoromethanes norefiel group, difluoroleomethanesnorefinyl group or trifluoroethanesulfininole group.
  • Finolyl group methanesulfoninole group, ethanesulfonyl group, propane sulphonylon group, butanesulfonyl group, etc., quinolenosenorephoninole group, trifluoromethanesulfonyl group, difluoromethanesulfonino group or tri Halogen-substituted alkylsulfonyl groups such as fluoroethanesulfonyl group, methanesulfonamide groups, ethanesulfonamide groups, propanesulfonamide groups, butanesulfonamide groups such as butanesulfonamide groups, triflides Olomethanesulfone Halide-substituted alkylsulfonamide groups such as amide group, difluoromethanesulfonamide group or trifluoroethanesulfonamide group, aryl groups such as phenyl group or naphthyl group
  • the compound of the present invention represented by the general formula (1) is a novel compound, and the compound represented by the general formula (1) can be produced by the method described in the following reaction formula (1).
  • a halogen atom typified by a chlorine atom, an alkoxy group typified by a methoxy group and an ethoxy group, an aryloxy group typified by a phenoxy group, an acyloxy group typified by a acetyloxy group and a benzoyloxy group, and a methoxycarbonyloxy group
  • anoroxycarbonyloxy group, arylcarbonylcarbonyl group represented by phenylcarbonyloxy group, N-hydroxysuccinic acid imide, 1-hydroxybenzotriazole and imidazole group Each can be illustrated.
  • the amine amide derivative represented by the general formula (11) or a salt thereof is mixed with a known carbonyl compound represented by the general formula (12) in a solvent-free or solvent-free manner with a base or base and By reacting in the presence of a metal reagent such as trialkylaluminum, the diamine derivative represented by the general formula (1) can be produced.
  • alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali hydroxides such as magnesium hydroxide and calcium hydroxide, earth metals such as sodium hydride and potassium hydride
  • Alkali metal hydrides such as sodium methoxide, alkali metal alkoxides such as sodium metoxide, alkali metal oxides such as sodium oxide, carbonates such as potassium carbonate and sodium carbonate, triphosphate Phosphoric acid salts such as strong rhodium, trisodium phosphate, dihydrogen phosphate monobasic, phosphate monobasic phosphate, sodium acetate, acetates such as sodium acetate, pyridine, 4- (dimethylamino) pyridine, Organic bases such as triethylamine, imidazole, diazabicycloundecene and the like can be mentioned.
  • the amount of these bases used is not particularly limited, and can be used as a solvent when the above organic bases are used.
  • the solvents used in the reaction include water, methanol, ethanol, alcohols such as propanol and butanol, halogenated hydrocarbons such as dichloromethane and chloroform, benzene, toluene, and xylene.
  • Aromatic hydrocarbons such as hexane, heptane and other aliphatic hydrocarbons, dimethylformamide (DMF), dimethylacetamide (DMA;), dimethylsulfoxide (DMSO), 1, 3 —Non-proton polar solvents such as dimethyl-2-imidazolidinone (DM I), 1-methyl-2-pyrrolidone (NMP), ethyl ether, isopropyl ether, 1,2-dimethoxetane (DME), tetrahydrofuran ( THF), ethers such as dioxane, and nitriles such as acetonitrile and propionitryl. That.
  • DMF dimethylformamide
  • DMA dimethylacetamide
  • DMSO dimethylsulfoxide
  • 1, 3 —Non-proton polar solvents such as dimethyl-2-imidazolidinone (DM I), 1-methyl-2-pyrrolidone (NMP), ethyl
  • Examples of the metal reagent of the reaction formula (1) include Grignard reagent, alkylamine, and alkylamine aminomagnesium halide (Bodrou X reaction), lithium aluminum hydride, trimethylaluminum, triethylalminium, etc. be able to.
  • the amount of these metal reagents used is not particularly limited.
  • the solvents used in the reaction include halogenated hydrocarbons such as dichloromethane and chlorohonolem, aromatic hydrocarbons such as benzene, toluene and xylene, and aliphatic carbons such as hexane and heptane.
  • halogenated hydrocarbons such as dichloromethane and chlorohonolem
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • aliphatic carbons such as hexane and heptane.
  • ethers such as hydrogen, ethyl ether, isopropyl ether, 1,2-dimethoxetane (DME), tetrahydrofuran (THF), and dioxane.
  • reaction temperature and reaction time of the above reaction can be varied over a wide range.
  • the reaction temperature is preferably 1 to 78-200 ° C, more preferably -78 to 100, and the reaction time is preferably 0.0 1 to 50 hours, more preferably 0.1 to 15 hours. It is.
  • the equivalent amount of the carbonyl compound represented by the general formula (12) is preferably 1 to 2 equivalents, more preferably 1 to 1.2 equivalents relative to the amine derivative represented by the general formula (11).
  • the amine derivative represented by the general formula (1 1) of the reaction formula (1) and a salt thereof can be produced by the method described in the reaction formula (2) under £ ⁇ .
  • R 40 is a t-butyl group Alternatively, it represents a benzyl group that may be substituted.
  • the diamine derivative represented by general formula (11) can be produced by reacting the diamine derivative represented by general formula (13) with an acid or by hydrogenation reaction.
  • Examples of the acid used in this case include hydrogen chloride, hydrogen bromide, sulfuric acid, nitric acid, acetic acid, and trifluoroacetic acid.
  • the amount of these acids used is not particularly limited, and can be used as a solvent.
  • the hydrogenation reaction can be carried out in a suitable solvent, in the presence of a catalyst, at normal pressure or under pressure, in a hydrogen atmosphere.
  • catalysts include palladium catalysts such as palladium-carbon, nickel catalysts such as Raney nickel, cobalt catalysts, ruthenium catalysts, rhodium catalysts, platinum catalysts, etc.
  • Solvents include water, alcohols such as methanol and ethanol, benzene And aromatic hydrocarbons such as toluene, chain or cyclic ethers such as ether, dioxane and tetrahydrofuran, and esters such as ethyl acetate.
  • the reaction temperature and reaction time for the above reaction can be varied over a wide range. In general, the reaction temperature may be appropriately selected from 120 ° C. to the reflux temperature of the solvent to be used, and the reaction time in the range of several minutes to 96 hours.
  • reaction formula (3) The diamine derivative represented by the general formula (13) of the reaction formula (2) and a salt thereof can be produced by the method described in the following reaction formula (3).
  • R l, R 2, R 3, R4, R 5, R 6, R 7, R 8, R 9, R 1 0, R 40, A and X 3 have the same meanings as defined above.
  • the amine derivative represented by the general formula (15) or a salt thereof is mixed with a known amino acid derivative represented by the general formula (14) in a solvent-free or solvent-free manner in a base, a base, and a trihydrate.
  • a metal reagent such as alkylaluminum
  • a diamine derivative represented by the general formula (13) can be produced.
  • the same base as that used in the method represented by the reaction formula (1) can be used.
  • the amount of these bases used is not particularly limited, and can be used as a solvent when the above organic bases are used.
  • the same metal reagent as that used in the method represented by the reaction formula (1) can be used.
  • the amount of these metal reagents used is not particularly limited.
  • the amount of the compound represented by the general formula (14) is 1 to 4 equivalents, preferably 1 to 2 equivalents relative to the amine derivative represented by the general formula (15).
  • the reaction temperature and reaction time for the above reaction can be varied over a wide range.
  • the reaction temperature is 120 to 200 ° C, preferably 0 to 100 ° C.
  • the reaction time is from 0.01 to 50 hours, preferably from 0.1 to 15 hours.
  • the compound represented by the general formula (14) in the reaction formula (3) is prepared by converting the amino acid derivative represented by the general formula (16) into thionyl chloride, oxalyl chloride, phosgene, oxychloride, Anti-phosphorus such as phosphorus chloride, phosphorus pentachloride, thionyl bromide, phosphorus tribromide, jetylaminosulfur trifluoride, 1, 1'-carbonylbis- 1H-imidazole, etc. It can be manufactured by the usual method of adapting.
  • the compound represented by the general formula (14) in the reaction formula (3) is obtained by converting the amino acid derivative represented by the general formula (16) into alcohols such as methyl alcohol and ethyl alcohol, phenol, nitrophenol. It can also be produced by a conventional method of reacting with phenols such as
  • the compound represented by the general formula (14) in the reaction formula (3) is a compound having an amino acid derivative represented by the general formula (16), such as methyl formate or phenyl formate. It can also be produced by a conventional method of reacting with lipates.
  • the compound represented by the general formula (14) in the reaction formula (3) is obtained by converting the amino acid derivative represented by the general formula (16) into N-hydroxysuccinic acid imide, 1-hydroxybenzazotriazole, etc. Can also be produced by a conventional method of reacting with.
  • the amine derivative represented by the general formula (15) of the reaction formula (3) and the salt thereof are other than those commercially available.
  • the Gabriel method, the Delpin method, the cyan group or amide, imine, oxime, etc. Can be easily prepared by the method described in Tetrahedron Asymmetry, 1st 1st, 1907 (2000). it can.
  • the diamine derivative represented by the general formula (13) can also be produced by the method described in the reaction formula (4).
  • R 1, R 2, R 3, R 4., R 5, R 6, R 7, R 8, R 9, R 10, R 40 and A are the same as described above.
  • the amin derivative represented by the general formula (15) and a salt thereof are reacted with the known amino acid derivative represented by the general formula (16) in the absence of a solvent or in a solvent.
  • the condensing agent in the case where the diamine derivative represented by the formula (1 3) can be produced N, N′-dicyclohexylcarbodiimide,
  • the amount of the condensing agent to be used is 1 to 3 equivalents, preferably 1 to 1.5 equivalents, relative to the compound represented by the general formula (16).
  • the amount of the carboxylic acid derivative represented by the general formula (16) is 1 to 2 equivalents, preferably 1 to 1.2 equivalents relative to the amine derivative represented by the general formula (15).
  • the reaction temperature and reaction time for the above reaction can be varied over a wide range. In general, the reaction temperature is 120 to 200 ° C, preferably 0 to 100 ° C. The reaction time is from 0.01 to 50 hours, preferably from 0.1 to 15 hours.
  • the compound represented by the general formula (16) reacts the corresponding amino acid with carboxylic acid formate, carbonates such as O-methyl-0_ (p-nitroxyphenyl) carbonate, etc. Can be produced by a conventional method.
  • the known carboxylic acid derivatives represented by 1 7) are thionyl chloride, oxalyl chloride, phosgene, phosphorus oxychloride, phosphorus trichloride, phosphorus pentachloride, thionyl bromide, phosphorus trichloride, jetylaminosulfurate. It can be produced by a conventional method in which it is reacted with refluoride, 1,1 ′ monocarbonylbis-1,1H-imidazole or the like.
  • the compound represented by the general formula (12) in the reaction formula (1) is obtained by converting a known carboxylic acid derivative represented by the general formula (17) into alcohols such as methyl alcohol and ethyl alcohol, phenol, nitro It can also be produced by a conventional method of reacting with phenols such as phenol.
  • the compound represented by the general formula (1 2) in the reaction formula (1) is a known carboxylic acid derivative represented by the general formula (1 7), such as chloroformate such as methyl chloroformate and phenyl chloroformate. It can also be produced by a conventional method of reacting with esters.
  • the compound represented by the general formula (1 2) in the reaction formula (1) is obtained by reacting a known carboxylic acid derivative represented by the general formula (17) with N-hydroxysuccinic acid imide, 1-hydroxyl. It can also be produced by a conventional method of reacting with benzotriazole or the like.
  • the compound of the present invention represented by the general formula (1) can also be produced by the method described in the reaction formula (5).
  • the amine derivative represented by the general formula (11) and the salt thereof are reacted with the known carboxylic acid derivative represented by the general formula (17) in a solvent-free or solvent,
  • the diamine derivative represented by the general formula (1) can be produced.
  • the condensing agent includes N, N'-dicyclohexylcarbodiimide, 1, 1'-canolebonino lebis mono 1 H-imidazole 1-ethyl 3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 2-chloro-1,3-dimethylimidazole chloride, etc. can be used.
  • the amount of the condensing agent used is ⁇ 3 equivalents, preferably 1 ⁇ : 1.5 equivalents, relative to the compound represented by the general formula (17).
  • the amount of the carboxylic acid derivative represented by the general formula (17) is 1 to 2 equivalents, preferably 1 to 1.2 equivalents, relative to the amine derivative represented by the general formula (11).
  • the reaction temperature and reaction time for the above reaction can be varied over a wide range. In general, the reaction temperature is 120 to 200 ° C, preferably 0 to 100 ° C. The reaction time is from 0.01 to 50 hours, preferably from 0.1 to 15 hours.
  • the compound of the present invention represented by the general formula (1) can also be produced by the method described in the reaction formula (6).
  • the amine derivative represented by the general formula (18) or a salt thereof is mixed with a known compound represented by the general formula (14) in a solvent-free or solvent-free manner in a base or base.
  • a metal reagent such as trialkylaluminum
  • the same base as that used in the method represented by the reaction formula (1) can be used.
  • the amount of these bases used is not particularly limited, and can be used as a solvent when the above organic bases are used.
  • the same metal reagent as that used in the method represented by the reaction formula (1) can be used.
  • the amount of these metal reagents used is not particularly limited.
  • the amount of the compound represented by the general formula (14) is 1 to 4 equivalents, preferably 1 to 2 equivalents relative to the amine derivative represented by the general formula (18).
  • the reaction temperature and reaction time for the above reaction can be varied over a wide range.
  • the reaction temperature is -20 to 200 ° C, preferably 0 to 100 ° C.
  • the reaction time is from 0.01 to 50 hours, preferably from 0.1 to 15 hours.
  • the compound of the present invention represented by the general formula (1) can also be produced by the method described in the reaction formula (7).
  • the condensing agent includes N, N'-dicyclohexyl carpositimide, 1, 1'-canolebonino lebis 1 H-imidazole, 1-etenore 1- (3-dimethylaminopropyl) Carbodiimide 'hydrochloride, 2-chloro 1, 1-dimethyl imidazolium chloride, etc. can be used.
  • the amount of the condensing agent to be used is 1 to 3 equivalents, preferably 1 to 1.5 equivalents, relative to the compound represented by the general formula (16).
  • the amount of the carboxylic acid derivative represented by the general formula (16) is 1 to 2 equivalents, preferably 1 to 1.2 equivalents relative to the amine derivative represented by the general formula (18).
  • the reaction temperature and reaction time for the above reaction can be varied over a wide range. Generally, the reaction temperature is -20 to 200 ° C, preferably 0 to 100 ° C. The reaction time is from 0.01 to 50 hours, preferably from 0.1 to 15 hours.
  • the compound of the present invention represented by the general formula (1) can also be produced by the method described in the reaction formula (8).
  • R l, R 2, R 3, R4, R 5, R 6, R 7, R 8, R 9, R 1 0, A, X 3 and C have the same meanings as defined above.
  • the amine derivative represented by the general formula (19) and a salt thereof are mixed with a known compound represented by the general formula (20) in the absence of a solvent or a solvent in the presence of an abasic or base.
  • the diamine derivative represented by the general formula (1) can be produced by performing the reaction below.
  • the same base as that used in the method represented by the reaction formula (1) can be used.
  • the amount of these bases used is not particularly limited, and can be used as a solvent when the above organic bases are used.
  • the same organic solvent as that used in the method represented by the reaction formula (1) can be used.
  • the amount of the compound represented by the general formula (20) is 1 to 4 equivalents, preferably 1 to 2 equivalents relative to the diamine derivative represented by the general formula (19).
  • reaction temperature and reaction time for the above reaction can be varied over a wide range.
  • the reaction temperature is 120 to 200 ° C, preferably 0 to 100 ° C.
  • the reaction time is from 0.01 to 50 hours, preferably from 0.1 to 15 hours.
  • the amine derivative represented by the general formula (19) of the reaction formula (8) and a salt thereof can be produced by the method described in the reaction formula (9).
  • R 2 R 3, R 4, R 5, R 6, R 7, R 8, R 9, R 10, A and Qi are the same as above, and R 1 is t-butyl
  • R 1 is t-butyl
  • the diamine derivative represented by general formula (19) can be produced by reacting the diamine derivative represented by general formula (1) with an acid or by hydrogenation reaction.
  • Examples of the acid used in this case include hydrogen chloride, hydrogen bromide, sulfuric acid, nitric acid, acetic acid, and trifluoroacetic acid.
  • the amount of these acids used is not particularly limited, and can be used as a solvent.
  • the same catalyst as that used in the method represented by the reaction formula (2) can be used.
  • the same solvent as that used in the method represented by the reaction formula (1) can be used.
  • the reaction temperature and reaction time for the above reaction can be varied over a wide range.
  • the reaction temperature may be appropriately selected from 120 ° C. to the reflux temperature of the solvent to be used, and the reaction time in the range of several minutes to 96 hours.
  • the compound represented by the general formula (20) in the reaction formula (8) usually reacts the corresponding alcohols with phosgenes such as phosgene and triphosgene, and chloroformate esters such as phenol oleoresin. It can be manufactured by the method.
  • the diamine derivative represented by the general formula (1) may have an asymmetric carbon depending on the type of the substituent, and may exist as an optical isomer, a diastereoisomer, a racemate, and a mixture of any ratio. All isomers of this type, as well as mixtures thereof, are also encompassed by the diamine derivatives used in the present invention.
  • the diamine derivative represented by the general formula (1) of the present invention is particularly suitable for the pesticidal fungus of Plasmopara viticola (Pseudoperonospora cubensis), the fungus (Pseudoperonospora cubensis) Phytophthora infestans), lawn physium disease (Pseudopara viticola (Pseudoperonospora cubensis), the fungus (Pseudoperonospora cubensis) Phytophthora infestans), lawn physium disease (Psmopara viticola (Pseudoperonospora cubensis), the fungus (Pseudoperonospora cubensis) Phytophthora infestans), lawn physium disease (Psmopara viticola (Pseudoperonospora cubensis),
  • Pythium aphanidermatum other such as the batter was for powerful sterilization operation in a number of eggs fungi to be representative
  • Plasmopara species, Pseuaoperonosporaft s Peronospora plague a wide variety of plants caused by pathogens Pythium spp., Base and the disease, seedling blight Exhibits a very good control effect against Pythium disease. It also has a strong bactericidal activity against rice blast fungus (Pyricularia oryzae), and exhibits excellent control effects against rice blast.
  • bactericides used in the pest control composition of the present invention include industrial bactericides such as anti-corrosion and anti-bacterial agents, agricultural and horticultural bactericides, medical and disinfectant bactericides, etc. As an antibacterial agent, it exhibits an excellent control effect.
  • Such fungicides include triadimephone, hexaconazole, propiconazonole, ipconazonole, prochloraz, trifnoremizonole, tebuconazonole, epoxiconazonore, difuenoconazole, funoresilazole, triadimenole fol Quinconazole, Vitertanol
  • Tetraconazole triticonazonole, fur triafonore, penconazole, diniconasole, fenbuconazonole, bromconazonore, imibenconazonore, simeconazole, microbutanyl, himexazole, imazalil, framite
  • Azol fungicides such as diazole, oxyspoconazole, oxyspoconazole fumarate, pefazoate and prothioconazole, pyrimidin fungicides such as pyriphenox, fenarimol, nurimol and buprimate, mepanipyrim, cyprodinil, pyrimethanil , Ailinopyrimidine fungicides such as diflumetrim, asylalanine fungicides such as metalaxyl, metalaxyl-M, oxadixil, benalaxyl, Ofanate methyl, Benomyl, Benzimidazole,
  • Antibiotics such as rapeseed oil, natural product fungicides such as rapeseed oil and machine oil, carbamate fungicides such as Benchavalycarb isopropyl, iprovarial carp, propamocalp, and dietofencalp, fluoride, fludioxonil Pyrrole fungicides such as fenpiclonil, plant activators that induce plant disease resistance such as probenazole, cibenzolral S-methyl, thiazinyl, quinoline fungicides such as quinoxyphene, oxolinic acid, cyflufenamide, Fenhexamide, metrafenone, picobenzamide, proquinazide, famoxadone, cyazofamide, fenamidone, zoxamide, chlorothalonil, simoxanyl, quibutane, dithianone, fluazinam, phorpet, diclof Ruanide, tri
  • the compound of the general formula (2) is described in WO 0 1 1 0 8 25 and describes the bactericidal activity and the production method.
  • the compound of the general formula (3) is described in U S 6 6 20 8 12 and describes the bactericidal activity and the production method.
  • R 11 represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an arylalkyl group or a heterocyclic alkyl group
  • R 12 and R 17 are R 1 3 and R 14 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms
  • R 15 and R 16 each represent a hydrogen atom
  • R 1 8 Represents an aryl group or a hetero ring.
  • the compound of the general formula (5) is described in W 0 200 3 008 372, and the bactericidal activity and production method are described.
  • R 19 is an alkyl group having 1 to 6 carbon atoms substituted with halogen, a cycloalkyl group having 3 to 6 carbon atoms substituted with halogen, or an alkenyl group having 2 to 6 carbon atoms substituted with halogen.
  • R 20 and R 25 each represent a hydrogen atom
  • R 21 and R 22 each independently represent a hydrogen atom
  • R 23 and R 24 each represent hydrogen.
  • R 26 represents an aryl group or a heterocyclic ring.
  • R 27 represents a methyl group or a chloro group
  • R 28 represents a methyl group, a chloro group, a bromo group, or a cyano group
  • R 29 represents a chloro group, a bromo group, a trifluoromethyl group, or a cyanomethoxy group
  • R 30 represents a methyl group or an isopropyl group.
  • the compound of the general formula (7) is described in WO 2003 3 1 5 5 19 and describes the insecticidal activity and the production method.
  • R 3 1 is 1, 1, 1, 2, 3, 3, 3—heptafnoroleol 2-propyl group or 1, 1, 2, 2, 3, 3, 3—heptafluoro 1— Represents a propyl group.
  • the compound of the general formula (8) is described in Japanese Patent Application Laid-Open No. 2001-342 186, and describes the insecticidal activity and the production method.
  • Xi is a hydrogen atom or a fluorine atom
  • R3 2 and R3 3 are a hydrogen atom and an alkyl group having 1 to 4 carbon atoms, respectively
  • Q 2 is a phenyl group, a halogen atom, or a carbon number
  • Haloanolequinyl group cycloalkyl group having 3 to 6 carbon atoms, halocycloalkyl group having 3 to 6 carbon atoms, alkoxy group having 1 to 3 carbon atoms, haloalkoxy group having 1 to 3 carbon atoms, 1 to 3 carbon atoms Alkylthio group,
  • a substituted phenyl group having one or more substituents which may be the same or different selected from a phenyl group, a pyridyl group, or a halogen atom, an alkyl group having 1 to 4 carbon atoms, and having 1 to 4 carbon atoms
  • C-4 alkylolamino group, C1-C4 dialkylamino group, Cyano group, nitro group, hydroxyl group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarboninoleoxy group, carbon Q 1 is a pyridyl group having one or more substituents which may be the same or different and is selected from an alkoxy group, a noblenyl group, a acetylamino group, a phenyl group, and the like represented by formula (A).
  • Y i and Y 5 may be the same or different, halogen atom, carbon number 1
  • the compound of the general formula (9) is described in WO 2005-73 165, and describes the insecticidal activity and production method.
  • X 2 is a hydrogen atom or a fluorine atom
  • R35, R36 are each a hydrogen atom, an alkyl group having 1 to 4 carbon atoms
  • R34 is Kill group having 1 to 6 carbon atoms, carbon atoms
  • E2 is an alkylene group having 1 to 4 carbon atoms, an alkylene group having 2 to 4 carbon atoms, an alkynylene group having 3 to 4 carbon atoms, or 1 to 4 carbon atoms
  • a haloalkylene group having 2 to 4 carbon atoms, a haloalkynylene group having 3 to 4 carbon atoms, R39 represents a cycloalkyl group having 3 to 8 carbon atoms, a halocycloalkyl group having 3 to 8 carbon atoms, Ciano group, D Toro group, hydroxyl group, phenyl group, or the same or different, halogen atom, carbon number :!
  • Q 4 is a general formula (B):
  • Y 6 and may be the same or different, a halogen atom, carbon number 1
  • the compound of the general formula (1 0) is described in W 2O 2 0 5-2 1 4 8 8 and describes the insecticidal activity and the production method.
  • chlorbendilate As an acaricide that can be used in the pest control composition of the present invention, chlorbendilate, phenisobromolate, tetradiphone.
  • CPCBS chlorfenson
  • BPPS BPPS
  • Quinomethionate Amitraz
  • Benzomate Hexithiazox
  • Fenbutazin oxide Sihexatin, Dienochlor
  • Clofuentezin Pyridaben
  • Fenpyroximate Fuanazaquine
  • Tebufenvirado Pyrimidinophene
  • Tosechinose Examples include etoxazolinole, spirodiclofen, spinomesifen, amidfulmete, and diflovidazine.
  • the pest control composition of the present invention contains at least one compound of one or more other fungicides, insecticides, and acaricides in an amount of 0.001 to 95% by weight, preferably 0.01 to 80% by weight. % contains.
  • the amount of active ingredient of the pest control composition of the present invention is usually 0.5 to 20% by weight for powders, 5 to 50% by weight for emulsions, 10 to 90% by weight for wettable powders, granules 0.1 to 20% by weight for agents and 10 to 90% by weight for flowable formulations.
  • the amount of carrier in each dosage form is usually 60 to 99% by weight for powders, 40 to 95% by weight for emulsions, and 10 to 90% for wettable powders. /.
  • the amount of adjuvant is usually 0.1 to 20 weight for powders. /. 1 to 20% by weight for emulsions, 0.1 to 20% by weight for wettable powders, 0.1 to 20% by weight for granules, and 0.1 to 20% by weight for flowable formulations.
  • the agent containing the pest control composition of the present invention as an active ingredient is algae
  • bacteria names are given as non-limiting examples.
  • rice potato pattern Panes oryzae
  • sesame leaf blight sesame leaf blight
  • coat blight sesame leaf blight
  • Gray mold disease (Botrytis cinerea), mycorrhizal disease (Sclerotinia sclerotiorum), cynomolgus: 7, lacunno tuchi f (Hhizoctonia solani), evening, -Laspot (Sclerotinia homoeocarpa) ⁇ Calf, Curdularia geniculata (Puccinia zoysiae), Helmintosporium leaf blight (Cochiliobolus sp.), Rhynchosporium secalis, Les, b Disease (Pyricularia oryzae A / 1 blight (Gaeumannomyces graminis), ash rot (Colletotrichum graminicola) ⁇ snow rot brown microtuberculosis (Typhula incarnata), snow rot black sclerotia nuclear disease (Typhula ishikariensis), snow rot large fungus Nuclear
  • the pest control composition of the present invention is effective for pest control.
  • pests include, for example, Lepidoptera (LEPIDOPTERA), Bat power (Endoclyta excrescens), Black bat (Endoclyta sinensis), White bat (Palpifer sexnotata Acleris comariana), Lingo cockatoo (Adoxophyes orana iasciata), Teyanoko Kakumon no Maki (Adoxophyes sp.), Lingomon no Maki Maki (Archips breviplicanus), Mitare Kakumon no Maki (Archips fuscocupreanus), Kakmon no Maki (Archips xylosteanus) fur 7 ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ (Cnephasia cinereipalpana), ⁇ ⁇ ⁇ ⁇ (Cydia kurokoi), ⁇ ⁇ ⁇ DRINSHINGA (Eucoenogenes aestu)
  • Nezara antennata Nezara viridula, Tymon Mosquito Memushi (Piezodorus hybneri), Chiyanoku Neaokamemushi (Plautia stali), Inekuro force Memushi (Scotinophara lurida), Iwasaki stink bug (Starioides iwasakii), nightshade Kamemu
  • Stepphanitis fasciicarina Nashigumbai (Stephanitis nashi), Sedgegumbai (Stephanitis pyrioides), Himegumbai (Uhlerites debile), Knorememi Gumbai
  • Rhualosiphum padi Rhualosiphum padi
  • Leptinotarsa decemlineata Corn nolate worms. (Diabrotica sp.) Involvulus cupreus, Rhynchites heros), Cylas formicarius, apple beetle
  • Echinocnemus squameus Ezocepes postfasciatus, Hypera nigrirostris, Hypera postica, Lissorhoptrus orresophile zolist Paramecium (Phyllobius armatus), Chibikofukizomuushi (Sitona japonicus), ⁇ Tami nozomuushi (Anthonomus grandis), coconut beetle (Sitophilus oryzae), Kokuzoumushi (Sitophilus zeamais) , THYSANOPTERA, Asaphothrips obscurus, Chirothrips manicatus, Dendrothrips minowai, F.
  • the cockroach As (ORTHOPTERA), the cockroach (Periplaneta americana), the cockroach (Periplaneta fuliginosa), the cockroach (Periplaneta japonica), the Blattella germanica, Mesamaki (Homorocoryphus jezoensis), Hemocory (Homorocoryphus lineosus), Kera (Gryllotalpa sp.), Coago (Oxya hyla intricata), Oxya. Yezoensis, Tonosama mikutoria (Locusta migratoria)
  • Diptera includes the following species: Tipula aino, Bradysia agrestis, Asphondylia sp. Dacus cucurbitae, Micus dorsalis), Dacus tsuneonis, Ohtono, Madaraminokue (Rhacochlaena japonica), Hydrellia griseola ⁇ Hydrellia sasakii, Oh Toshou Drosophila suzukii, Chlorops oryzae, Meromyza nigriventris, Agromyza oryzae)
  • Nemoku Lisenchu (turschmanruella oryzae ⁇ , Southern Nemusaresentyuyu (Pratylenchus coffeae), Suzuran Negusasencentu (Pratylenchus convallariae), ⁇ loosi, Pseylenchus neglectus, Pratylenchus penetrans, Pratylenchus sp., Helicotylenchus dihystera, Helicothylrina Yuli (Helicotylenchus sp.), Holylaimus (Hoplolaimus sp.), Nisefukuguchi Senchu (Rotylenchulus reniformis)
  • Heterodera elachista Gussis Tosenchu (Heterodera erlycines), Clover cistocentiyu (Heterodera trifolii), Alena ria (Meloidogyne arenaria), Tsuno Kinekop 'Sentiyu (Meloidogyne camelliae), Shinobu Nekobusenchu (Meloidogyne graminis), Tanekpusenteyu
  • Thermobia domestica etc., Termites (ISOPTERA), Diptero termites (Crvptotermes domesticus VIII Coptotermes iormosanus), Sharon ants (Reticulitermes speratus), Taiwan termites (Odontoter es formosanus) OPT, OC PS Hiratachiyate (Liposcelis bostrychophilus), flea eyes (SIPHONAPTERA),
  • molluscs such as oyster (Oxidus gracilis) include slugs (Incilaria bilineata).
  • the pest control composition of the present invention is used as it is to control various pests, or is diluted appropriately with water or suspended or suspended in an amount effective for pest control. It can be used for plants that are expected to occur.For example, in addition to spraying pests on pests that occur in fruit trees, cereals, vegetables, etc., soaking seeds in chemicals, seed dressing, Seed treatment such as calper treatment, soil all-layer treatment, crop application, floor soil mixing, cell seedling treatment, planting hole treatment, plant root treatment, top dressing, rice box treatment, water surface treatment, etc. And can be absorbed from the roots. In addition, it can also be applied to nutrient solution in nutrient solution (hydroponic) cultivation, smoke, or trunk injection. Furthermore, for example, in addition to spraying on storage insects, house pests, sanitary pests, forest pests, etc., it can also be used for application to house building materials, smoke, baits and the like.
  • the pest control composition of the present invention is generally used in a form convenient for use in accordance with a conventional formulation method for agricultural and horticultural drugs. That is, these Is mixed with an appropriate inert carrier or an auxiliary agent that imparts a desired function if necessary, and dissolved, separated, suspended, mixed, impregnated, adsorbed or adhered, as appropriate. What is necessary is just to formulate and use for a dosage form, for example, a suspension agent, an emulsion, a liquid agent, a wettable powder, a granule, a powder agent, a tablet.
  • the inert carrier that can be used in the present invention may be either solid or liquid.
  • materials that can be used as a solid inert carrier include soybean flour, cereal flour, wood flour, bark flour, saw flour, Tobacco stem powder, tarmi shell powder, bran, fiber powder, residues after extraction of plant extracts, synthetic polymers such as ground synthetic resin, clays (for example, kaolin, bentonian straw, acidic clay), talc (for example, talc) ), Silicas (for example, diatomaceous earth, silica sand, mica, white carbon (hydrous finely divided silicon, hydrous silicic acid is a synthetic highly dispersed silicic acid, and some products contain calcium silicate as the main component)), activated carbon Inorganic minerals such as powder, pumice, calcined diatomaceous earth, ground brick, fly ash, sand, calcium carbonate, calcium phosphate End, ammonium sulfate, ammonium phosphate, nitric weaker,
  • the material which can be a liquid inert carrier is selected from those having solvent ability itself and those which can disperse the active ingredient compound with the aid of an auxiliary agent without having solvent ability.
  • the following carriers can be exemplified, but these are used alone or in the form of a mixture of two or more, for example, water, alcohols (for example, methanol, ethanol, isopropanol, butanol, ethylene glycol).
  • Ketones eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.
  • ethers eg, jetinoleether, dioxane, cellosolve, diisopropyl ether, tetrahydrofuran, etc.
  • fat Group hydrocarbons eg kerosene, mineral oil, etc.
  • Aromatic hydrocarbons eg benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, etc.
  • halogenated hydrocarbons eg dichloromethane, black mouth form, tetrachlorocarbon, black mouth benzene, etc.
  • esters Eg, ethyl acetate, butyl acetate, ethyl propionate, diisobutyl phthalate, dibutyl phthalate, di
  • auxiliary agent As the auxiliary agent, the following typical auxiliary agents can be exemplified, and these Adjuvants are used depending on the purpose and can be used alone, in some cases with two or more adjuncts, and in some cases, no adjuncts can be used at all.
  • a surfactant is used as an auxiliary agent, for example, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxy Ethylene higher fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkyl aryl sulfonate, naphthalene sulfonate, lignin sulfonate, higher alcohol Surfactants such as oleyl sulfate can be indicated.
  • auxiliary agents can be used as auxiliary agents, such as casein, gelatin, starch, methyl cellulose, carboxy Adjuvants such as methyl cellulose, arabia gum, polybutyl alcohol, pine oil, coconut oil, bentonite, xanthan gum and lignin sulfonate can be used.
  • auxiliary agents such as wax, stearate, alkyl phosphate ester and the like can be used.
  • auxiliary agents such as wax, stearate, alkyl phosphate ester and the like can be used.
  • auxiliary agents such as naphthalene sulfonic acid condensate and condensed phosphate can be used.
  • antifoaming agent for example, an auxiliary agent such as silicone oil can be used.
  • the pest control composition of the present invention is stable to light, heat, oxidation, etc., but if necessary, an antioxidant or an ultraviolet absorber such as BHT (2, 6-dibutyl butyl 4- Methylphenol), phenol derivatives such as BHA (Butylhydroxyanisole), bisphenol derivatives, phenyl naphthylamine, phenyl- ⁇ -naphthylamine, and condensates of phenetidine and acetone.
  • BHT 2, 6-dibutyl butyl 4- Methylphenol
  • phenol derivatives such as BHA (Butylhydroxyanisole)
  • bisphenol derivatives bisphenol derivatives
  • phenyl naphthylamine phenyl- ⁇ -naphthylamine
  • condensates of phenetidine and acetone condensates of phenetidine and acetone.
  • a more stable composition can be obtained by adding an appropriate amount of a benzophenone compound as a stabilizer
  • the pest control composition of the present invention can be used to control the various pests as they are, appropriately diluted with water or the like, or suspended in an amount effective for pest control. It can be used by applying it to a place where the expected crop or occurrence is not desirable. The amount used varies depending on various factors such as the purpose, target pests, crop growth status, pest generation tendency, weather, environmental conditions, dosage form, application method, application location, application timing, etc. As an active ingredient per arel .lg ⁇ 1 0 It may be applied by appropriately selecting from the range of 00 g, preferably in the range of 1 g to 500 g.
  • the pest control composition of the present invention can be mixed with plant protection agents and materials such as herbicides, fertilizers, soil conditioners, plant growth regulators, etc. to make a multipurpose composition with further excellent efficacy.
  • the reaction solution was mixed with 5% aqueous citrate solution, saturated brine, saturated bicarbonate.
  • the extract was washed successively with an aqueous sodium solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 2.86 g of the desired product as a white solid (yield 88%).
  • reaction solution was washed successively with 5% aqueous citrate solution, saturated brine, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 3.06 g of the desired product as a white solid (yield 8 7%)
  • the aqueous layer was adjusted to pH 12 using sodium hydroxide and extracted with dichloromethane.
  • the organic layer was washed with 2N aqueous sodium hydroxide solution and then dried over anhydrous magnesium sulfate.
  • the inorganic salt was filtered and concentrated under reduced pressure to obtain 0.67 g of the desired product as a yellow oily substance (yield 87%).
  • reaction solution was washed successively with 5% aqueous citrate solution, saturated brine, 2N aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate.
  • the inorganic salt was filtered and concentrated under reduced pressure.
  • the resulting crude product was washed with diisopropyl ether to obtain 2.5 g of the desired product as a white solid (yield 47%).
  • reaction solution was washed successively with 5% aqueous citrate solution, saturated brine, 2N aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 1.25 g of the desired product as a white solid (yield 44%).
  • reaction solution was washed successively with 5% aqueous citrate solution, saturated brine, 1N aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. Filter inorganic salt and concentrate under reduced pressure The crude product thus obtained was washed with diisopropyl ether to obtain 0.35 g of the desired product as a white solid (yield 66%).
  • N- [2- (RS) -aminopropyl] benzofuran mono-2-carboxylic acid amide hydrochloride (0.50 g, 1.96 mm o 1), imidazonole (0.44 g, 6. 4 7 mm o 1) was added and stirred at room temperature for 5 hours.
  • the reaction solution was washed successively with 5% aqueous citrate solution, saturated brine, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate.
  • the reaction solution was washed successively with 5% aqueous citrate solution, saturated brine, 2N aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with a mixed solution of diisopropyl ether and n-hexane to obtain 3.60 g of the target product as light yellow crystals (yield 74%) .
  • reaction solution was washed successively with 5% aqueous citrate solution, saturated brine, 2N aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 0.58 g of the desired product as white crystals (yield: 58%).
  • reaction solution was washed successively with 5% aqueous citrate solution, saturated Japanese salt water, 2N aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 0.74 g of the desired product as white crystals (yield 8 9
  • reaction solution was washed successively with 5% aqueous citrate solution, saturated brine, 2N aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 0.33 g of the desired product as white crystals (yield 49%).
  • reaction solution was washed successively with 5% aqueous citrate solution, saturated aqueous sodium hydrogen carbonate solution and water, and then dried over anhydrous sodium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 0.52 g of the desired product as a white solid (yield 82%).
  • the aqueous layer was adjusted to pH 12 using sodium hydroxide (10.40 g), extracted with dichloromethane (500 ml), and 2 N aqueous sodium hydroxide solution (500 ml). After washing with, it was dried over anhydrous sodium sulfate. The inorganic salt was filtered and then concentrated under reduced pressure to obtain the target product 2.1.95 g as a white solid (yield 88%).
  • reaction solution was washed successively with water, 5% aqueous citrate solution, and saturated aqueous sodium hydrogen carbonate solution, and then dried over anhydrous sodium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was recrystallized using n-hexane and ethyl acetate to give 3.05 g of the desired product as a white solid (yield: 93% ).
  • the reaction mixture was washed successively with 5% aqueous citrate solution, water, saturated aqueous sodium hydrogen carbonate solution and water, and the organic layer was dried over anhydrous sodium sulfate. After the inorganic salt was filtered off, the crude product obtained by concentration under reduced pressure was recrystallized using disopropyl ether to obtain 26.9 g of the desired product as a white solid (yield 84%).
  • Table 1 The compounds represented by the formula (1) that can be produced in the same manner as those described above including the compounds of Examples 1 to 30 are shown in Table 1 as compounds 1 to 1 1 5 6.
  • Table 2 shows some of the physical properties.
  • Me is a methyl group
  • Et is an ethyl group
  • nPr is a normalpropyl group
  • iPr is an isopropyl group
  • nBu is a noremanolebutinore group.
  • I B u is an isobutynol group
  • s B u is a secondary butyl group
  • t B u is a tertiary butyl group
  • neo Pen is a 2,2-dimethylol propyl group
  • 2-E t Hex is 2 —Ethylhexyl group
  • MO E represents a methoxetyl group
  • cP r—CH 2 represents a cyclopropylmethyl group
  • c H ex—CH 2 represents a cyclohexylmethyl group
  • CF 3 represents trifluoromethyl.
  • CF 3 CH 2 is 2, 2, 2-trifluoroethyl group, C 1 CH 2 is chloromethyl group, CH 3 CHC 1 is chloroethyl group, CC 1 3 CH 2 is 2, 2, 2— Trichloroethyl group, 'CC 1 3 C (Me) 2 is 2, 2, 2— Trichloro 1, 1-dimethyl ethynole group, 2— Boc AE is 2— (N— Tasari -Butyloxycarbonyl) aminoethyl group, POC E t is 1_ (isopropoxycarbonyl) ethyl group, 1 — Me e — 1— Me S—E t is 1-methyl-1-methylthioethyl group , Ph is a phenyl group, 4-Me Ph is a 4-methylphenyl group, Bn is a benzyl group , O; _M e— B n is a single methinolevendinore group, 1—NP is a 1 naph
  • the diamine derivative represented by the formula (1) may have an asymmetric carbon depending on the type of the substituent, and may exist as an optical isomer, a diastereoisomer, a racemate, and a mixture of any ratio.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
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  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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Abstract

L'invention concerne une composition pesticide contenant comme principe actif, un dérivé de diamine, de formule (1), dans laquelle R1 représente un alkyle C1-6, etc.; R2 et R5 indépendamment l'un de l'autre représentent hydrogène, alkyle C1-6, etc.; R3 et R4 représentent indépendamment hydrogène, alkyle C1-6, etc., ou R3 et R4 sont liés ensemble de manière à former un noyau d'hydrocarbure C3-6 ; R6, R7, R8 et R9 représentent indépendamment hydrogène, alkyle C1-6 , etc.; R10 représente hydrogène, alkyle C1-6, etc.; A représente oxygène, etc.;et Q1 représente aryle ou un hétérocycle. La composition comprend également un ou plusieurs composés sélectionnés à partir du groupe constitué d'un autre bacéricide, d'un insecticide, et d'un acaricide.
PCT/JP2006/317935 2006-01-19 2006-09-05 Composition pesticide contenant un derive de diamine Ceased WO2007083411A1 (fr)

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US8466180B2 (en) 2006-09-11 2013-06-18 Syngenta Crop Protection Llc Insecticidal compounds
US8686044B2 (en) 2008-08-13 2014-04-01 Mitsui Chemicals Agro, Inc. Amide derivative, pest control agent containing the amide derivative, and use of the amide derivative
CN102119143B (zh) * 2008-08-13 2017-07-21 三井化学Agro株式会社 酰胺衍生物、含有该酰胺衍生物的有害生物防除剂及其使用方法
CN111164076A (zh) * 2017-09-13 2020-05-15 先正达参股股份有限公司 杀微生物的喹啉(硫代)甲酰胺衍生物

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EP2322502B1 (fr) 2008-08-13 2019-09-18 Mitsui Chemicals Agro, Inc. Procédé de production d un dérivé amide
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CN110583653A (zh) * 2019-10-15 2019-12-20 中国农业科学院棉花研究所 一种杀虫组合物及其用途

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Cited By (7)

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US8466180B2 (en) 2006-09-11 2013-06-18 Syngenta Crop Protection Llc Insecticidal compounds
US8686044B2 (en) 2008-08-13 2014-04-01 Mitsui Chemicals Agro, Inc. Amide derivative, pest control agent containing the amide derivative, and use of the amide derivative
US9237745B2 (en) 2008-08-13 2016-01-19 Mitsui Chemicals Agro, Inc. Amide derivative, pest control agent containing the amide derivative, and use of the amide derivative
CN102119143B (zh) * 2008-08-13 2017-07-21 三井化学Agro株式会社 酰胺衍生物、含有该酰胺衍生物的有害生物防除剂及其使用方法
US9756856B2 (en) 2008-08-13 2017-09-12 Mitsui Chemicals Agro, Inc. Amide derivative, pest control agent containing the amide derivative, and use of the amide derivative
US10582708B2 (en) 2008-08-13 2020-03-10 Mitsui Chemicals Agro, Inc. Amide derivative, pest control agent containing the amide derivative, and use of the amide derivative
CN111164076A (zh) * 2017-09-13 2020-05-15 先正达参股股份有限公司 杀微生物的喹啉(硫代)甲酰胺衍生物

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