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WO2000029387A1 - Derives de 2- anilino (3h)- pyrimidone, intermediaires dans la production de ces derniers, procede de production de ces derniers et pesticides contenant ces derniers comme ingredient actif - Google Patents

Derives de 2- anilino (3h)- pyrimidone, intermediaires dans la production de ces derniers, procede de production de ces derniers et pesticides contenant ces derniers comme ingredient actif Download PDF

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Publication number
WO2000029387A1
WO2000029387A1 PCT/JP1999/006207 JP9906207W WO0029387A1 WO 2000029387 A1 WO2000029387 A1 WO 2000029387A1 JP 9906207 W JP9906207 W JP 9906207W WO 0029387 A1 WO0029387 A1 WO 0029387A1
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Prior art keywords
group
trifluoromethyl
pyrimidinone
amino
phenyl
Prior art date
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PCT/JP1999/006207
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English (en)
Japanese (ja)
Inventor
Kenji Hirai
Ryuta Ohno
Natsuko Okano
Maho Nagaoka
Atsushi Uchida
Yuriko Yoshino
Chikako Ota
Toshiki Fukuchi
Kazuhiko Kikutake
Shinji Kawaguchi
Original Assignee
Sagami Chemical Research Center
Mitsubishi Chemical Corporation
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Application filed by Sagami Chemical Research Center, Mitsubishi Chemical Corporation filed Critical Sagami Chemical Research Center
Priority to JP2000582374A priority Critical patent/JP4600620B2/ja
Priority to AU10790/00A priority patent/AU1079000A/en
Publication of WO2000029387A1 publication Critical patent/WO2000029387A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic 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
    • C07D239/28—Heterocyclic 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • the present invention relates to 2-anilino-4 (3H) -pyrimidinone derivatives and production intermediates, their production methods, and pesticides containing them as active ingredients.
  • the present invention relates to a pesticidal composition containing a 2-anilino-4 (3H) -pyrimidinone derivative as an active ingredient, and particularly to arthropods (insects) in the fields of agriculture and horticulture, clothing, food and shelter, and livestock * pets.
  • arthropods insects
  • nematodes nematodes
  • helminths and protozoa or diseases and weeds that are harmful to agricultural and horticultural crops.
  • pests that have acquired resistance to pesticides that have been widely used in the past.
  • various pesticides such as triazoles (triadimefon, etc.) and benzimidazols (benomyl,
  • triazoles triadimefon, etc.
  • benzimidazols benomyl
  • Various diseases that have acquired resistance to pesticides such as thiophanate methylate), dicarboxyimides (procymidone, iprodione, etc.), and phenylamides (metalaxyl, oxadixyl, etc.) have appeared in various places.
  • organophosphates dinitrothion, malathion, protiphos, DDVP, etc.
  • pirates Agrochemicals permethrin, cypermethrin, humvalerate, cyhalosulin, etc.
  • benzoylpereas difluvenzuron, tefluvenzuron, chlorfluazuron, etc.
  • nereistoxins cartap, bensultap, etc.
  • pesticides for which pests have not yet acquired resistance for example, dithio-potato-bamate-phthalimid-type pesticides.
  • these are generally large in the amount and frequency of application, and from the viewpoint of environmental pollution and the like. Not preferred. Therefore, it shows a sufficient control effect even at low doses against various pests that have acquired resistance to conventional general-purpose agricultural and horticultural fungicides, insecticides, and acaricides, and has a negative impact on the environment.
  • acaricides the development of highly safe acaricides is also expected, as they exhibit an excellent control effect on mites that have been resistant to conventional acaricides.
  • WO93 / 21162 includes a 2-anilino-4 (3H) -pyrimidinone derivative having a structure similar to the compound of the present invention.
  • 2-anilino-4 (3H) -pyrimidinone derivatives having an optionally substituted aryl group on the 3-position nitrogen atom and an optionally substituted vinyl group have been disclosed. There is no description at all.
  • herbicidal activity and physiological activity as a plant growth regulator are described.
  • other physiological activities such as insecticidal and acaricidal activities and bactericidal activities. Disclosure of the invention
  • An object of the present invention is to provide a high control effect on various pests that are resistant to conventional fungicides and insecticides, acaricides, nematicides and the like for agricultural and horticultural use, clothing and shelter-related or livestock and pets.
  • Another object of the present invention is to provide a novel pesticidal agent which exhibits high crop safety and excellent herbicidal activity against weeds.
  • the present inventors have conducted intensive studies in order to solve the above-mentioned problems, and as a result, as shown in the following general formula (1), an aryl group which may be substituted on the 3-position nitrogen atom or a substituted aryl group.
  • the present inventors have found that a novel 2-anilino-4 (3H) -pyrimidinone derivative having a vinyl group which may be a compound having the above characteristics has led to the completion of the present invention.
  • the present invention provides a compound represented by the general formula (1)
  • R 1 represents a halogen atom, ( ⁇ to (: 4 alkyl group, (! To haguchi alkyl group or a phenyl group which may be substituted), and R 2 represents a hydrogen atom or a halogen atom.
  • R 3 represents an optionally substituted aryl group, an optionally substituted 2 _ (-alkoxy) ethyl group or an optionally substituted vinyl group, represents a hydrogen atom, a C i -C 4 alkyl group, ⁇ Alkenyl group, ( ⁇ ⁇ (: 4 h alkyl group, (C i ⁇ alkoxy) ⁇ alkyl group, ⁇ alkoxy (C!
  • Represents a 4 alkyl) sulfonyl le radical X is a hydrogen atom, a halogen atom, ⁇ al kill group, ( ⁇ - (4 Ha port alkyl group, c 3 to c 6 alkenyl group, c 3 to c 6 alkynyl group, ⁇ C 5 Ashiru group, a carboxy group, (C i to alkoxy) carbonyl group, Shiano group, a hydroxyl group, ( ⁇ - (- 4 alkoxy group ⁇ Ha port alkoxy group, ⁇ alkoxy ( ⁇ C 4 alkoxy) group, a carboxy (C i to alkoxy) group,
  • R 1 and R 3 have the same meanings as described above. Represents a pyrimidinone derivative represented by ( ⁇ to (: 6 alkyl group, n is 0 or 2.)) and a general formula (3 )
  • R a -I (4) (wherein, R “is a C, to C 4 alkyl group, a C 3 to alkenyl group, ( ⁇ to ( 4 haloalkyl group, (( ⁇ to (: 4 alkoxy) to (: 4 Alkyl group, ⁇ alkoxy ( ⁇ (: 4 alkoxy) ⁇ alkyl group, (C! ⁇ Haloalkoxy) ⁇ alkyl Group, ( ⁇ ⁇ alkylthio) ( ⁇ ⁇ ( 4 alkyl group, (( ⁇ ⁇ acetyloxy) ( ⁇ ⁇ alkyl group, thiocyanato ( ⁇ ⁇ alkyl) group, ⁇ acetyl group, (d
  • the present invention provides a compound represented by the general formula (2b), which is an intermediate for producing the 2-anilino-4 (3H) -pyrimidinone derivative of the present invention:
  • R 1 represents a.
  • R 3 a may be a good Ariru or substituted also be substituted 2-(-C 4 alkoxy) Echiru group as defined above
  • R 5 a is represents a hydrogen atom or a ⁇ C 6 alkyl group.
  • n is 0 or 2. However, if R 5 a is a hydrogen atom, n represents relates pyridinium Mijinon derivative represented by a 0.).
  • the present invention provides a compound represented by the general formula (5):
  • R 3 a may be a good Ariru or substituted also be substituted 2 - ( ⁇ - where (: 4 alkoxy) Echiru represents a group) ⁇ Li one Ruisochioshi Ane Bok derivative represented by the And the general formula (6) NH 2 OR 1
  • the present invention relates to a method for producing a 2-alkylsulfonyl-4 (3H) -pyrimidinone derivative represented by
  • the present invention also provides a compound represented by the general formula (2f), which is an intermediate for producing the 2-anilino-4 (3H) -pyrimidinone derivative of the present invention.
  • R 3 b is optionally substituted ( ⁇ (:. 5 Ashiru) methyl group, optionally substituted 2-arsenide Dorokishechiru group, location Represents a 3-substituted-2-alkylthio-4 (3H) -pyrimidinone derivative represented by the following formula: ⁇ represents a 2-hydroxyethyl group or an optionally substituted vinyl group. It is.
  • R 1 and R 5 have the same meanings as described above; R 7 , and ⁇ each independently represent a hydrogen atom or a ⁇ alkyl group.
  • 3-alkenyl-4 (3H) ⁇ The double bond of the alkenyl group of the pyrimidinone derivative is oxidatively cleaved to obtain a compound of the general formula (2h)
  • R 1 represents a halogen atom such as a fluorine atom, a chlorine atom and a bromine atom; a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group and an isobutyl group.
  • Alkyl groups such as fluoromethyl group, chloromethyl group, bromomethyl group, trichloromethyl group, trifluoromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2,2,2-trifluoro (:!
  • ⁇ ⁇ C-alkyl groups such as chloroethyl group, pentafluoroethyl group, 3-chloropropyl group; halogen atom, ( ⁇ ⁇ (: 4 alkyl group or d ⁇ ⁇ alkyl group, etc.)
  • Examples include a phenyl group which may be substituted, and preferably a trifluoromethyl group, a pentafluoroethyl group or a trichloromethyl group.
  • R 2 and R 2a examples include a hydrogen atom; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and preferably a hydrogen atom, a fluorine atom, a chlorine atom, and a bromine atom. Can be mentioned.
  • the optionally substituted Ariru group represented by R 3 and R 3 a fluorine atom, chlorine atom, bromine atom, a halogen atom iodine atom; a methyl group, E ethyl group, a propyl group, an isopropyl group, a butyl (!
  • Haloalkylsulfinyl such as chloromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, etc.
  • C-alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, isopropylsulfonyl group, butylsulfonyl group, isobutylsulfonyl group, s-butylsulfonyl group, t-butylsulfonyl group; chloromethylsulfonyl group, Jifuruoromechi Rusuruhoniru group, triflate Ruo b methylsulfonyl group, a trichloromethyl scan Ruhoniru group, 2, 2, 2-triflate Ruo Roe such chill sulfonyl group ( ⁇ - (4 Haroaru alkylsulfonyl group; an amino group; Mechiruamino group, An ethylamino group, Propyl amino group, isopropylamino group, such Puchiru
  • a vinyl group optionally substituted represented by R 3 and R 3 b a vinyl group, Bok propenyl group, Bok propene - 2 I group, Bok butenyl group, Bok butene - 2-
  • examples thereof include a benzyl group, a 2-butene-2-yl group, a 3-methyl-1-butenyl group, and a toppentenyl group.
  • optionally substituted represented by R 3 b (( ⁇ ⁇ ( 5 Ashiru) methyl group, optionally substituted 2-arsenide Dorokishechiru group, 2 may be substituted - as Ha port Echiru group Are formylmethyl, triformylethyl, acetonyl, 1-formylpropyl, 2-butanone-1-yl, 2-butanone-3-yl, 3-methyl-2-butanone-1- Substituents such as 2-yl group and 2-pentanone-1-yl group; 2-hydroxyl, 2-hydroxypropyl, 1-hydroxy-2-propyl, 2-hydroxybutyl, 3 -Substituents such as -hydroxy-2-butyl, 2-hydroxypentyl, 2-hydroxy-3-methylbutyl; 2-chloroethyl, 2-bromoethyl, 2-chloropropyl, 2-propyl Bromopropyl group, 1-chloro-2-propyl group, 1-bromo-2-propyl
  • R 4 and R 4 a a methyl group, Echiru group, a propyl group, an isopropyl group, a butyl group, such as isobutyl ( ⁇ - (4 alkyl group; 2-propenyl group, 2 - C, such as butenyl 3 to C 4 alkenyl group; chloromethyl group, trifluoromethyl group, 2-chloroethyl group, 3-fluoropropyl group, etc.
  • the R 5, a methyl group, Echiru group, a propyl group, an isopropyl group, Petit group, an isobutyl group, S- butyl group, a C -C 6 alkyl group a t- butyl group and the like can ani gel.
  • the R 5 a and R 5 b a hydrogen atom; a methyl group, Echiru group, a propyl group, I an isopropyl group, a butyl group, an isobutyl group, S- butyl group, mention -C 6 alkyl group a t- butyl group and the like be able to.
  • R 6 examples include Ci to C 6 alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, an s-butyl group and a t-butyl group.
  • R ⁇ R ⁇ K s and R 1 "include a hydrogen atom; an alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, an S-butyl group and a t-butyl group. be able to.
  • X represents a hydrogen atom; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, an s-butyl group and a t-butyl group.
  • C t ⁇ alkyl group such as a group; Furuoromechiru group, chloromethyl group, bromomethyl group, trichloromethyl group, triflate Ruo Russia methyl, 1-black port Echiru group, 2-black port Echiru group, 3 -, such as click Roropuropiru group d to C 4 haloalkyl groups; such as 2-propenyl group, 3-methyl-2-propenyl group, 2-butenyl group, 3-methyl-2-butenyl group, 1-buten-3-yl group, etc.
  • ⁇ Alkoxy) carbonyl group cyano group; hydroxyl group; ⁇ alkoxy group such as methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, s-butoxy group, t-butoxy group; ⁇ (: Such as methoxy, difluoromethoxy, 2-chloroethoxy, 3-chloropropoxy, 2-chloro-1-methylethoxy, 2,2,2-trifluoroethoxy, etc.
  • acylamino groups such as methylsulfonylamino and ethylsulfonylamino groups
  • d-amino groups such as methylsulfonylamino and ethylsulfonylamino groups
  • a lucylsulfonylamino group A nitro group and the like.
  • Examples of the leaving group represented by L include a halogen atom such as a chlorine atom, a bromine atom and an iodine atom, a methylsulfonyloxy group, a trifluoromethylsulfonyloxy group, a phenylsulfonyloxy group, and a p-tolylsulfonyloxy group.
  • Examples thereof include a substituted sulfonyloxy group such as a xy group.
  • preferred compounds from the viewpoint of biological activity as a pesticide are those wherein X is a halogen atom, an alkyl group, a haloalkyl group or a nitro group; Is a hydrogen atom, an alkyl group, an alkoxyalkyl group, a haloalkoxyalkyl group, an alkoxyalkoxyalkyl group, an alkylthioalkyl group, an acyloxyalkyl group, an alkoxycarbonyl group or an alkylsulfonyl group.
  • the 2-anilino-4 (3H) -pyrimidinone derivative (1) of the present invention and intermediates for the production thereof can be produced by the methods exemplified in the following Production Methods 11 to 3.
  • the production method 1 uses the 2-alkylthiopyrimidinone derivative (2d) and the 2-alkylsulfonylpyrimidinone derivative (2a) as raw materials, and reacts with the aniline derivative (3) to obtain the 2-anilino derivative of the present invention.
  • -4 (3H) -Pyrimidinone derivative (la) is produced, and halogenation of the 5-position of the pyrimidine ring (Step 1) and introduction of a substituent on the nitrogen atom at the 2-position lead to 2-anilino-4 ( 3H) -This is a method for producing a pyrimidinone derivative (Id). [Production method 1]
  • Step 1 is to react a 2-alkylthio-4 (3H) -pyrimidinone derivative and a 2-alkylsulfonyl-4 (3H) -pyrimidinone derivative with a aniline derivative (3) as a starting material.
  • This is a process for producing a 2-anilino-4 (3H) -pyrimidinone derivative (la).
  • the reaction of Step 11 is preferably carried out in the presence of a base from the viewpoint of good yield.
  • a base examples include sodium hydride, potassium hydride, lithium amide, sodium amide, lithium diisopropylamide (LM), butyllithium, t-butyllithium, trimethylsilyllithium, lithium hexamethyldisilazide, sodium carbonate, and carbonated lithium.
  • alkali metal bases such as potassium-1-butoxide, triethy
  • This reaction can be carried out in a solvent, and any solvent that does not harm the reaction can be used.
  • the solvent include amide solvents such as ⁇ , ⁇ -dimethylformamide (DMF), N, N-dimethylacetamide, N-methylpyrrolidone, nitrile solvents such as acetonitrile and propionitrile, Aromatic hydrocarbon solvents such as benzene, toluene, xylene, and benzene, aliphatic hydrocarbon solvents such as pentane, hexane, and octane; getyl ether, disopropyl ether, tetrahydrofuran (THF), Solvents that do not hinder the reaction, such as ether solvents such as toxetane (DME) and 1,4-dioxane, dimethyl sulfoxide (DMS0), or a mixed solvent thereof can be used.
  • amide solvents such as ⁇ , ⁇ -dimethylform
  • the reaction can be carried out at a temperature appropriately selected from the range of -78 ° C to the reflux temperature of the solvent, whereby the desired product can be obtained in high yield.
  • Step 1 is a process for preparing a 2-anilino-4 (3H) -pyrimidinone derivative of the present invention by halogenating the 5-position of the pyrimidine ring using a 2-anilino-4 (3H) -pyrimidinone derivative (la) as a raw material. (Lb).
  • This step 12 can be carried out by using a halogenating agent.
  • halogenating agent examples include chlorine, bromine, iodine, potassium fluoride, sulfuryl chloride, N-chloro mouth succinic acid imid, and N-bromo.
  • Halogens such as succinic acid imid, N-iodine succinic acid imid, t-butyl hypochlorite, getylaminosulfur trifluoride, carbon tetrachloride / triphenylphosphine, carbon tetrabromide / triphenylphosphine Chemical agents can be used. At this time, the target compound can be obtained in good yield by using 1 to 2 equivalents of the base with respect to the substrate.
  • This reaction can be carried out in a solvent, and any solvent that does not harm the reaction can be used.
  • the solvent include aromatic hydrocarbon solvents such as benzene and dichlorobenzene, aliphatic hydrocarbon solvents such as pentane, hexane and octane, getyl ether, diisopropyl ether, THF, ME, 1,4 Ether solvents such as dioxane; halogen solvents such as chloroform, dichloromethane and carbon tetrachloride; organic acid solvents such as acetic acid and propionic acid; and mixed solvents thereof.
  • the reaction can be carried out at a temperature appropriately selected from the range of ⁇ 20 ° C. to the solvent reflux temperature to obtain the desired product in good yield.
  • Step 13 is a process for reacting 2-anilino-4 of the present invention using 2-anilino-4 (3H) -pyrimidinone derivative (la) or (lb) as a raw material and reacting with reagent (4) in the presence of a base. This is a step of producing a 4 (3H) -pyrimidinone derivative (Id).
  • This reaction is performed in the presence of a base.
  • a base examples include sodium hydride, potassium hydride, lithium amide, sodium amide, LDA, butyllithium, t-butyllithium, trimethylsilyllithium, lithium hexamethyldisilazide, sodium carbonate, carbonated lithium, sodium acetate.
  • Alkali metal bases such as potassium acetate, sodium methoxide, sodium methoxide, sodium ethoxide, sodium phosphate-t-butoxide, triethylamine, diisopropylethylamine, tributylamine, N-methylmorpholine, DMA, N, N-methylethylaniline
  • Organic bases such as, 4-t-butyl- ⁇ , ⁇ -dimethylaniline, pyridine, DMAP, picoline, lutidine, DBU, MBC0, and imidazole can be used. By using 1 to 2 equivalents of the base relative to the substrate, the desired product can be obtained in good yield.
  • This reaction can be carried out in a solvent, and any solvent that does not harm the reaction can be used.
  • the solvent include amide solvents such as MF, ⁇ , ⁇ -dimethylacetamide and ⁇ -methylpyrrolidone, nitrile solvents such as acetonitrile and propionitrile, benzene, toluene, xylene, and chlorobenzene.
  • Lipstick Aromatic solvents such as benzene, aliphatic hydrocarbon solvents such as pentane, hexane, and octane; ether solvents such as dimethyl ether, diisopropyl ether, THF, DME, 1,4-dioxane; MS0, Alternatively, a mixed solvent thereof or the like can be used.
  • the reaction can be carried out at a temperature appropriately selected from the range of -20 to the reflux temperature of the solvent to obtain the desired product in good yield.
  • catalysts such as polyethers such as 18-crown-6, 15-crown-5, 12-crown-4, tetrabutylammonium bromide, tetrabutylammonium sulfate,
  • a quaternary ammonium salt such as thiammonium monoxide, or an alkali metal halide such as potassium iodide, potassium bromide, or sodium iodide
  • reagent represented by the general formula (4) used in Step 13 include methyl bromide, methyl iodide, butyl bromide, isopropyl iodide, aryl chloride, aryl bromide, methallyl chloride, and aryl methanesulfonate.
  • a part of the derivative (2e) is produced by the method exemplified in Production Method 12 below.
  • Production Method 1 is a method for producing a 2-mercapto-4 (3H) -pyrimidinone derivative (2c) by reacting an isothiocyanate (5) with a 3-amino acrylate derivative (6). Then, an alkylating agent (7) is reacted to give a 2-alkylthio-4 (3H) -pyrimidinone derivative (2d), and the sulfur atom is oxidized to give a 2-alkylsulfonyl-4 (3H) -pyrimidinone This is a method for producing the derivative (2e).
  • Step 1-4 Isothiocyanates (5) and 3-aminoacrylate In this step, the derivative (6) is reacted to produce a 2-mercaptopyrimidinone derivative (2c).
  • the reaction can be carried out in the presence of a base.
  • a base examples include triethylamine, diisopropylethylamine, tributylamine, N-methylmorpholine, DMA, ⁇ , ⁇ -getylaniline, and 4-t-butyl- Organic bases such as N, N-dimethylaniline, pyridine, DMAP, picoline, lutidine, DBU, MBC0, imidazole, sodium carbonate, carbonated lime, sodium hydrogencarbonate, hydrogenated lime, sodium hydride, hydrogenated Chemical lithium, lithium amide, sodium amide, LM, butyllithium, t-butyllithium, trimethylsilinolelithium, lithium hexamethyldisilazide, sodium acetate, potassium acetate, sodium methoxide, sodium Alkali metal bases such as trium ethoxide and potassium 1-butoxide can be used.
  • the base By reacting the base with 0.1 to 2 equivalents of the substrate
  • This reaction is preferably performed in a solvent.
  • a solvent any solvent that does not harm the reaction can be used.
  • Aromatic hydrocarbon solvents such as benzene, toluene, xylene, and chlorobenzene, and aliphatic hydrocarbons such as pentane, hexane, and octane can be used.
  • Hydrogen solvents such as getyl ether, diisopropyl ether, tetrahydrofuran (THF), dimethoxetane (DME), and 1,4-dioxane, acetone, methyl ethyl ketone (MEK), and hexanone Ketones, halogen solvents such as chloroform, dichloromethane, etc., nitrile solvents such as acetonitrile and propionitrile, and ester solvents such as ethyl acetate, propyl acetate, butyl acetate and methyl propionate.
  • ether solvents such as getyl ether, diisopropyl ether, tetrahydrofuran (THF), dimethoxetane (DME), and 1,4-dioxane
  • acetone methyl ethyl ketone
  • MEK methyl ethyl ketone
  • ester solvents
  • isothiocyanates (5) used as raw materials in this step are commercially available and can be easily obtained. Also, a method of reacting the corresponding anilines with, for example, thiophosgene, a method of reacting with carbon disulfide in the presence of tertiary amine, and then treating with methyl chloroformate [J. Am. Chera. Soc, 81, 4328, 1959, (WO 92/13835, EP 523244, US 5274166)] and the like.
  • the 3-aminoacrylic acid ester derivative (6) which is a raw material of this step, is commercially available and can be easily obtained, but can be obtained by a known method [for example, Japan Kokai Tokkyo Koho JP05 / 140060 (Chemical Abstracts 119: 249
  • step 1 the 2-mercapto-4 (3H) -pyrimidinone derivative (2c) is reacted with an alkylating agent (7) in the presence of a base to alkylate the sulfur atom to form a 2-alkylthio-4 ( This is a step of producing a 3H) -pyrimidinone derivative (2d).
  • Bases include sodium hydride, lithium hydride, lithium amide, sodium amide, LM, butyllithium, t-butyllithium, trimethylsilyllithium, lithium hexamethyldisilazide, sodium carbonate, potassium carbonate, Alkali metal bases such as sodium bicarbonate, sodium bicarbonate, sodium acetate, sodium acetate, sodium methoxide, sodium ethoxide, sodium-1-butoxide, triethylamine, diisopropylethylamine, tributylamine, Use organic bases such as N-methylmorpholine, ⁇ , ⁇ , ⁇ -getylaniline, 4-1-butyl- ⁇ , ⁇ -dimethylaniline, pyridine, DMAP, picoline, lutidine, DBU, DABC0, imidazole, etc. be able to. Although the stoichiometric amount of the base is sufficient for the substrate, there
  • This reaction is preferably performed in a solvent.
  • a solvent it does not harm the reaction. Any solvent that does not have an effect can be used, such as aromatic hydrocarbon solvents such as benzene, toluene, xylene, and benzene, aliphatic hydrocarbon solvents such as pentane, hexane, and octane; getyl ether; Ether solvents such as diisopropyl ether, THF, E, and 1,4-dioxane; ketones such as acetone, MEK and cyclohexanone; halogen solvents such as chloroform, dichloromethane and the like; acetonitrile, propioni Nitril solvents such as toryl, ester solvents such as ethyl acetate, propyl acetate, butyl acetate, and methyl propionate; amide solvents such as MF, N, N-dimethylacetamide, N-methylpyrrolidon
  • the reaction can be carried out at a temperature appropriately selected from the range of o ° C to the reflux temperature of the solvent, although it varies depending on the base used and the reaction conditions.
  • alkylating agent (7) used in this step examples include, for example, methyl iodide, methyl bromide, chloroiodide, chlorobromide, propyl iodide, propyl bromide, isopropyl iodide, isopropyl bromide, and isopropyl iodide.
  • Alkyl halides such as butyl, butyl bromide, isobutyl iodide, isobutyl bromide, s-butyl iodide, s-butyl bromo, and hexyl iodide are commercially available and easily available. preferable.
  • alkylating agents such as dimethyl sulfate and getyl sulfate can be used.
  • Step 1 is a step of oxidizing the 2-alkylthio-4 (3H) -pyrimidinone derivative (2d) to produce a 2-alkylsulfonyl-4 (3H) -pyrimidinone derivative (2e).
  • the oxidation can be carried out using an oxidizing agent, and the oxidizing agent used is an oxidizing agent generally used for oxidizing a sulfur atom, for example, a peracid such as peracetic acid, perbenzoic acid, m-chloroperbenzoic acid, or the like.
  • an oxidizing agent such as hydrogen peroxide, nitric acid, and potassium permanganate can be used.
  • This reaction is preferably carried out in a solvent, for example, aromatic hydrocarbon solvents such as benzene, toluene, xylene, and benzene, aliphatic hydrocarbon solvents such as pentane, hexane, and octane; Ether solvents such as diisopropyl ether, THF, DME and 1,4-dioxane; ketones such as acetone, MEK and cyclohexanone; halogen solvents such as chloroform and dichloromethane; water; or a mixture thereof. Any solvent that does not harm the reaction such as a solvent can be used.
  • aromatic hydrocarbon solvents such as benzene, toluene, xylene, and benzene
  • aliphatic hydrocarbon solvents such as pentane, hexane, and octane
  • Ether solvents such as diisopropyl ether, THF, DME and 1,4-dio
  • the reaction can be carried out at a temperature appropriately selected from the range of -20 ° C to the reflux temperature of the solvent, depending on the oxidizing agent used and the reaction conditions.
  • Production Method 13 is based on the reaction of an alkenyl isothiosinate derivative (5 ') with a 3-aminoacrylic acid ester derivative (6) to produce 3-alkenyl-2-mercapto-4 (3H)-
  • the pyrimidinone derivative (2) is prepared, and then alkylated on the sulfur atom using an alkylating agent (7) in the presence of a base, and then 3-alkenyl-2-alkylthio-4 (3H)-
  • the alkenyl group double bond of the pyrimidinone derivative (2g) is oxidatively cleaved to produce a 2-alkylthio-3-acylalkyl-4 (3H) -pyrimidinone derivative (2h).
  • 2-alkylthio-4 (3H) -pyrimidinone derivative (2 g) was obtained from WO 93/21 162 (CN 1079736, EP 636615, US 5518994, Japan Kokai Tokkyo Koho JP 06/321913), Japan Kokai Tokkyo Koho JP07 / 89941.
  • Step 17 is a reaction between an alkenyl isothiosineates (5 ') and a 3-amino acrylate derivative (6) to form a 3-alkenyl-2-mercapto-4 (3H) -pyrimidinone derivative (2 g ).
  • the reaction can also be carried out in the presence of a base.
  • Examples of the base include triethylamine, diisopropylethylamine, triptylamine, N-methylmorpholine, DMA, ⁇ , ⁇ -methylethylaniline, and 4-1-butyl- Organic bases such as ⁇ , ⁇ -dimethylaniline, pyridine, DMAP, picoline, lutidine, DBU, DABC0, imidazole, sodium carbonate, sodium carbonate, sodium carbonate, sodium carbonate, sodium hydrogencarbonate, sodium hydrogencarbonate, hydrogen hydrogen Sodium hydride, potassium hydride, lithium amide, sodium amide, LM, butyllithium, t-butyllithium, trimethylsilyllithium, lithiumhexamethyldisilazide, sodium acetate, potassium acetate, sodium methoxide, sodium Alkali metal bases such as methoxide and potassium 1-butoxide can be used.
  • the base By reacting the base with 0.1 to 2.0 equivalents of the substrate, the desired product can be
  • This reaction can be carried out in a solvent, and any solvent that does not harm the reaction can be used.
  • the solvent include aromatic hydrocarbon solvents such as benzene, toluene, xylene, and benzene, aliphatic hydrocarbon solvents such as pentane, hexane, and octane, dimethyl ether, and diisopropyl ether.
  • —Ether solvents such as ter, THF, DME, 1,4-dioxane, etc .; ketones such as acetone, methyl ethyl ketone (MEK), cyclohexanone; halogen solvents such as chloroform and dichloromethane; acetonitrile, propionitrile Ethyl acetate, propyl acetate, butyl acetate, ester solvents such as methyl propionate, etc., DMF, amide solvents such as ⁇ , ⁇ -dimethylacetamide, ⁇ -methylpyrrolidone, etc.
  • An alcoholic solvent such as methanol, methanol (MeOH), ethanol (EtOH), and isopropyl alcohol, S0, water, or a mixed solvent thereof can be used.
  • the reaction may be carried out at a temperature appropriately selected from the range of -78 ° C to the reflux temperature of the solvent, depending on the base used and the reaction conditions.
  • the alkenyl isothiocyanate derivative ') used as a raw material in this process is partially Is commercially available and can be easily obtained. Also, a method in which the corresponding amines are reacted with, for example, thiophosgene, and a method in which the corresponding halogenated alkenyls are reacted with thiocyanic acid potassium or sodium thiocyanate (J. Am. Chem. So, 59, 2012, 1937). ) Or by reacting with carbon disulfide in the presence of a tertiary amine, followed by treatment with methyl chloroformate [J. Am. Chem. Soc., 81, 4328, 1959, (WO 92/13835, EP 523244, US 527 4166)].
  • Step-18 is to react a 3-alkenyl-2-mercapto-4 (3H) -pyrimidinone derivative (2 g) with an alkylating agent (7) in the presence of a base to alkylate the sulfur atom, This is a step of producing an alkenyl-2-alkylthio-4 (3H) -pyrimidinone derivative (2 g).
  • Bases include sodium carbonate, carbon dioxide, sodium bicarbonate, sodium bicarbonate, sodium acetate, sodium acetate, sodium methoxide, sodium ethoxide, sodium l-butoxide, sodium hydride, sodium hydride Alkali metal bases such as lithium, sodium amide, butyllithium, t-butyllithium, LDA, trimethylsilyllithium, lithiumhexamethyldisilazide, triethylamine, disopropylethylamine, tributylamine, Use organic bases such as N-methylmorpholine, DMA, ⁇ , ⁇ -getylaniline, 4-t-butyl- ⁇ , ⁇ -dimethylaniline, pyridine, DMAP, picoline, lutidine, DBU, MBC0, imidazole, etc. Can be. Although the stoichiometric amount of the base is sufficient for the substrate, there is no problem even if it is
  • This reaction is preferably performed in a solvent.
  • a solvent any solvent that does not harm the reaction can be used.
  • Aromatic hydrocarbon solvents such as benzene, toluene, xylene, and chlorobenzene, and aliphatic hydrocarbons such as pentane, hexane, and octane can be used.
  • Hydrogen solvent getyl ether, diisopropyl Ether solvents such as ether, THF, ME, and 1,4-dioxane; ketones such as acetone, MEK, cyclohexanone; halogen solvents such as chloroform and dichloromethane; nitriles such as acetonitrile and propionitrile Solvent, ester solvents such as ethyl acetate, propyl acetate, butyl acetate, and methyl propionate; amide solvents such as DMF, N, N-dimethylacetamide and N-methylpyrrolidone; MeOH, EtOH, An alcoholic solvent such as isopropyl alcohol, DMS0, water, or a mixed solvent thereof can be used.
  • ketones such as acetone, MEK, cyclohexanone
  • halogen solvents such as chloroform and dichloromethane
  • nitriles such as acetonitrile and propionit
  • the reaction may be carried out at a temperature appropriately selected from the range of -78 ° C to the reflux temperature of the solvent, depending on the base used and the reaction conditions.
  • alkylating agent (7) used in this step examples include, for example, methyl iodide, methyl bromide, chloroiodide, chlorobromide, propyl iodide, propyl bromide, isopropyl iodide, isopropyl bromide, and isopropyl iodide.
  • Alkyl halides such as butyl, butyl bromide, isobutyl iodide, isobutyl bromide, s-butyl iodide, s-butyl bromide and hexyl iodide are commercially available and easily available. preferable.
  • alkylating agents such as dimethyl sulfate and getyl sulfate can be used.
  • the alkenyl group double bond of (2g) is oxidatively cleaved to produce a 2-alkylthio-3-acylalkyl-4 (3H) -pyrimidinone derivative (2h).
  • Step 19 can be carried out using an oxidizing agent.
  • the oxidizing agent used is an oxidizing agent used for the oxidative cleavage reaction of the double bond, for example, osmium tetroxide / sodium periodate, tetroxide
  • An oxidizing agent such as osmium / hydrogen peroxide, a lead tetraacetate / trimethylsilyl azide complex, ruthenium tetroxide, or a combination of oxidizing agents can be used.
  • the amount of the oxidizing agent used varies depending on the oxidizing agent used, but by using the oxidizing agent within 10 equivalents relative to the substrate, the desired product can be obtained in high yield.
  • the oxidizing agent when osmium tetroxide / sodium periodate is used as an oxidizing agent, It is preferable to use 0.005 to 5 equivalents of osmium oxide with respect to the substrate and 0.5 to 10 equivalents of sodium periodate with respect to the substrate from the viewpoint of good yield of the target product.
  • osmium tetroxide and sodium periodate are simultaneously added to the reaction system, and the reaction is carried out to produce the desired 2-alkylthio-3-acylalkyl-4 (3H) -pyrimidinone derivative (2h).
  • osmium tetroxide is reacted with a starting material, 3-alkenyl-2-alkylthio-4 (3H) -pyrimidinone derivative (2 g), to give a diol form represented by the following general formula (2h ′).
  • a starting material 3-alkenyl-2-alkylthio-4 (3H) -pyrimidinone derivative (2 g)
  • a diol form represented by the following general formula (2h ′ By reacting with sodium periodate, it can be converted to the desired 2-alkylthio-3-acylalkyl-4 (3H) -pyrimidinone derivative (2h).
  • the diol form (2h ') can be isolated, but there is no problem even if it is reacted with sodium periodate in the system as it is.
  • This reaction varies depending on the oxidizing agent used, but is preferably performed in a solvent.
  • the solvent include water, ether solvents such as dimethyl ether, diisopropyl ether, THF, and dioxane; nitrile solvents such as acetonitrile and propionitol; dichloromethane, chloroform, carbon tetrachloride; Any solvent that does not hinder the reaction, such as a halogenated solvent such as 1,2-dichloroethane, a solvent such as acetic acid or propionic acid, or a mixed solvent thereof can be used.
  • the reaction may be carried out at a temperature appropriately selected from the range of ⁇ 30 ° C. to the reflux temperature of the solvent, depending on the oxidizing agent used and the reaction conditions.
  • Step—10 is to reduce the formyl group of the 2-alkylthio-3-acylalkyl-4 (3H) -pyrimidinone derivative (2h) to give a 2-alkylthio-3- (2-hydroxyalkyl
  • This is a process for producing a 4) (3H) -pyrimidinone derivative (2i ').
  • the reduction can be performed using a reducing agent.
  • the reducing agent used include a reducing agent used for a reduction reaction of a carbonyl group, for example, lithium aluminum hydride, sodium aluminum hydride, and lithium trimethoxyaluminum hydride.
  • a reducing agent capable of reducing a normal carbonyl group such as sodium, triisopropoxyborohydride, tetrabutylammonium borohydride, diisobutylaluminum hydride and diborane can be used.
  • This reaction is preferably carried out in a solvent.
  • Alcohol solvents such as methanol, ethanol, propanol, isopropanol and butanol
  • ether solvents such as diethyl ether, diisopropyl ether, THF, DME and dioxane, benzene, toluene
  • Any solvent that does not hinder the reaction such as an aromatic hydrocarbon solvent such as benzene benzene, a solvent such as water, or a mixed solvent thereof can be used.
  • the reaction can be carried out at a temperature appropriately selected from the range of 0 ° C. to the solvent reflux temperature, although it varies depending on the reducing agent used and the reaction conditions.
  • Step 11 The 2-alkylthio-3- (2-hydroxyalkyl) -4 (3H) _pyrimidinone derivative (2) is obtained by substituting the hydroxyl group of the 3-position hydroxyalkyl group with a halogen atom. -(2-haloalkyl) -4 (3H) -pyrimidinone derivative (2j).
  • a usual hydroxylating reagent such as triphenyl phosphine / carbon tetrachloride, triphenyl phosphine / carbon tetrabromide, phosphorus trichloride, Phosphorus bromide, phosphorus pentachloride, phosphorus oxychloride, thionyl chloride, thionyl bromide, dimethyl bromosulfonate Mbromide or the like can be used.
  • hydroxyl group is substituted with a P-tolylsulfonyl group ⁇ methylsulfonyl group, it can be halogenated by reacting with a metal halide such as lithium bromide ⁇ bromide rim.
  • This reaction is preferably carried out in a solvent, such as a halogenated solvent such as dichloromethane, chloroform or carbon tetrachloride; a nitrile solvent such as acetonitrile and propionitrile; an amide solvent such as MF; pyridine; A pyridine-based solvent such as picoline, or a mixture of these solvents can be used as long as it does not harm the reaction.
  • a solvent such as a halogenated solvent such as dichloromethane, chloroform or carbon tetrachloride; a nitrile solvent such as acetonitrile and propionitrile; an amide solvent such as MF; pyridine; A pyridine-based solvent such as picoline, or a mixture of these solvents can be used as long as it does not harm the reaction.
  • the reaction can be carried out at a temperature appropriately selected from the range of o ° c to the reflux temperature of the solvent, although it varies depending on the halogenating agent used and the reaction conditions.
  • Step 1 The 2-haloalkyl group is obtained by directly halogenating the 2-alkoxyalkyl group at the 3-position of the 2-alkylthio-3- (2-alkoxyalkyl) -4 (3H) -pyrimidinone derivative (2i). This is a step of converting to 2-alkylthio-3- (2-haloalkyl) -4 (3H) -pyrimidinone derivative (2j).
  • a halogenating agent such as phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, or phosphorus oxychloride can be used.
  • This reaction can also be carried out in a solvent, such as halogenated solvents such as dichloromethane, chloroform, carbon tetrachloride, nitrile solvents such as acetate nitrile and propionitrile, and amide solvents such as DMF.
  • a solvent such as halogenated solvents such as dichloromethane, chloroform, carbon tetrachloride, nitrile solvents such as acetate nitrile and propionitrile, and amide solvents such as DMF.
  • a solvent such as halogenated solvents such as dichloromethane, chloroform, carbon tetrachloride, nitrile solvents such as acetate nitrile and propionitrile, and amide solvents such as DMF.
  • Any solvent that does not hinder the reaction such as pyridin-based solvents such as pyridine, pyridine and picoline, or a mixed solvent thereof can be used.
  • the reaction can be carried out at a temperature appropriately selected from the range of 0 ° C to the reflux temperature of the solvent, although it varies depending on the halogenating agent used and the reaction conditions.
  • Step 13 is a process in which 2-alkylthio-3- (2-haloalkyl) -4 (3H) -pyrimidinone derivative (2;) ′) is dehydrogenated in the presence of a base to give 2- A
  • This is a step of producing an alkylthio-4 (3H) -pyrimidinone derivative (2k).
  • This step is performed in the presence of a base.
  • the base include alkali metal bases such as sodium hydride, sodium methoxide, sodium methoxide, potassium-t-butoxide, alkali metal bases such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; triethylamine; Diisopropylethylamine, tributylamine, N-methylmorpholine, DMA, ⁇ , ⁇ -getylaniline, 4-1-butyl- ⁇ , ⁇ -dimethylaniline, pyridine, ⁇ , picoline, lutidine, DBU, DABC0, imidazo Organic bases such as toluene can be used.
  • the amount of the base used is 1 to 5 equivalents, preferably 1 to 2 equivalents, based on the raw material substrate, whereby the desired product can be obtained in good yield.
  • This reaction is preferably carried out in a solvent, and ether solvents such as getyl ether, diisopropyl ether, THF, DME, 1,4-dioxane, ketones such as acetone, MEK, cyclohexanone, and benzene , Toluene, xylene, benzene, etc., aromatic hydrocarbon solvents, pentane, hexane, octane, etc., aliphatic hydrocarbon solvents, methanol (MeOH), ethanol (EtOH), t-butanol, etc. Any solvent that does not harm the reaction such as alcoholic solvent, DMS0, water, or a mixed solvent thereof can be used.
  • ether solvents such as getyl ether, diisopropyl ether, THF, DME, 1,4-dioxane, ketones such as acetone, MEK, cyclohexanone, and benzene , Tolu
  • the pest control agent containing the compound of the present invention as an active ingredient is useful for repelling, controlling, and controlling pests in a wide range of fields such as agriculture, forestry, livestock industry, fisheries, and product preservation and public health in these industries. It is effective for etc.
  • the compound of the present invention is particularly useful for repelling and controlling pests in agriculture, forestry, etc., specifically when cultivating crops, harvests, trees, ornamental plants, etc., and in public health situations. Excellent effect as an insecticide, acaricide, fungicide used for control, etc., and as a herbicide against weeds of agricultural and horticultural crops and other useful plants (for example, urban greening, afforestation, tree planting, etc.) .
  • the compound of the present invention can be used for agricultural crops such as food crops (rice, wheat, corn, potatoes, sweet potatoes, beans, etc.), vegetables (brassaceae crops, sea urchins, eggplant, tomatoes, leeks, etc.), fruit trees (citrus fruits, apples, Grapes, thighs, etc., special crops (tobacco, tea, sugar beet, sugar cane, cotton, olive, etc.), pasture and forage crops (sorghum, grass, legumes, etc.) and ornamental plants It is effective for repelling and controlling pests such as arthropods, molluscs, nematodes, various fungi, etc. that may damage them when growing (herbs, flowers, garden trees, etc.) .
  • agricultural crops such as food crops (rice, wheat, corn, potatoes, sweet potatoes, beans, etc.), vegetables (brassaceae crops, sea urchins, eggplant, tomatoes, leeks, etc.), fruit trees (citrus fruits, apples, Grapes, thighs, etc., special crops
  • the compounds of the present invention are harmful when storing harvested products from the above-mentioned crops, such as cereals, fruits, tree nuts, spices and tobacco, and products that have been subjected to drying, powdering, etc. It is also effective for repelling and extermination of living things. It is also effective in protecting standing trees, fallen trees, processed timber, and stored timber from damage by pests such as termites and beetles.
  • Specific pests include, for example, those belonging to the arthropod phylum, mollusc phylum, and linear animal phylum as follows.
  • arthropod phylum Insecta examples include the following.
  • Lepidoptera for example, the family Noctuidae such as Lotus sycamore, Tobacco beetle, Totoga moth, and Evening managinaba; Suga family such as Konaga; Coleoptera such as Cyanococcus terrestris, Papilio persicae; Moth moth family such as moth; moth moth moth etc .; moth moth moth such as stag moth moth; moth moth family such as scotch moth; moth moth moth moth family such as cynophyta; Iridaceae such as moths; Kobumemeiga, Nikameichiyu, Petaherikuronomeiga Pterodaceae such as Ichimon disseri; Papilionidae such as Papilio epsilon; Family: Dermatophagidae such as stag beetle; Hitrigidae such as sword bee
  • the Coleoptera for example, Scarabaeidae, such as Scarabaeidae, Koohanamuguri, and Mamekogane; Tamabidae, such as Citrus beetle; Scarabaeidae, such as Marc beetle beetle; Longicorn beetles, such as beetles; beetles, beetles, beetles, and beetles; it can.
  • Hemiptera for example, stink bugs such as Coleoptera and Stinging bugs; Pingidae family such as pear bugs; Helicopteridae family such as P. terrestrial bugs; Dermatidae such as Nashigumbai, etc .; Dermatidae, such as Usumi dori-mekuragame; Cicada, such as Nichinisemi; Dermatidae, such as grapevine; Lepidoptera, such as Leafhoppers; Lepidoptera, such as brown beetle powers, and Tonidae, such as brown squirrels; Abahagoromo, such as Abahagoromo; Phyllidae, such as pear lice; Whitefly, silverleaf whitefly; Lamiaceae; Filophyceae, such as Cryophyla aphid; Lycoperidae, etc .; Aphid, Acer aphid, Acacia aphid, etc .; Stag beetles, such
  • a thrips family such as Citrus thrips, Chrysanthemum thrips, and a thrips thrips
  • a thrips family such as Kikuzama thrips and Inechida thrips.
  • the Hymenoptera include honeybees such as forceps and honeybees; honeybees such as apple honeybees; honeybees such as chestnut wasps; and honeybees such as barnacles.
  • the diptera include, e.g., soybean flies such as soybean flies; flies and fly flies; Engineering can be mentioned.
  • the Orthoptera includes, for example, Grasshoppers such as Kusakidiri; Crickets such as Amatsumushi; Laceae such as Kera; Examples of the order Collembiidae include, for example, the bryozoan family, such as the brown bryozoan; and the bryozoan family, such as matsumotoshibomibushi. Examples of the termites include termites, such as the termites, and examples of the earwigs include, eg, the earwigs such as the earworms.
  • arthropod phylum crustaceae and spider webs The following can be exemplified as arthropod phylum crustaceae and spider webs.
  • the crustacean isopods for example, there may be mentioned the family Oxodidae, such as the okadan cadaver.
  • the acarid mites of the order of the Arachnida include, for example, Cyprididae, Cyclamenidae, etc .; Dermatophagoides, such as Rhipicephalus; Dermatidae, such as Bud ⁇ Himehada2; Rust mites; apple rust mites; apple rust mites; As the mollusc phylum gastropods, the gastropods of the gastropods include, for example, Scutellaria mussels, and the peduncles include, for example, African snails, slugs, Nycophora methaji, Chacolana slugs, and U.S. it can.
  • the following can be exemplified as the nematode phantom net and the tail net.
  • Examples of the genus Coleoptera include, for example, Anguinaceae such as Imogusarecentiuyu; Tirencholinexes such as Namiishikusenshiyu; Platyrenxaceae such as Kitanegu Salenchiyu and Minaminexarecentiyu; Heparodelidae such as potato cysts; meloidoids such as sweet potato cysts; Cliconemataceae such as ⁇ ⁇ ; ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ And the like.
  • Examples of the order Causticidae include Longiduraceae, such as Ooharicentiyu, and Trichodulaceae, such as Yumiharisenyu.
  • the compound of the present invention is also effective for repelling, controlling and controlling pests that damage trees or affect the vigor of natural forests, plantations and urban green spaces.
  • specific pests include the following.
  • arthropod insects and spider webs examples include the following.
  • Scutellidae such as Sugidokuga and Gypsy moth
  • Kalehagaceae such as Makakareha and Gigakareha
  • Meigataceae such as Larix sylvestris
  • Gyagaceae such as L. brajaga
  • Kamamatsui Tohikihamaki Kurimiga and Sugigasa, etc.
  • Crickets such as Amerika shirohitori
  • moglitivigas such as shimoglitibiga
  • Wear for example, Scutellidae such as Sugidokuga and Gypsy moth
  • Kalehagaceae such as Makakareha and Gigakareha
  • Meigataceae such as Larix sylvestris
  • Gyagaceae such as L. brajaga
  • Kamamatsui Tohikihamaki Kurimiga and Sugigasa
  • Crickets such as Amerika shirohitori
  • moglitivigas such as shimoglitibiga
  • Wear
  • the Coleoptera for example, Scarabaeidae, for example, Scarabaeidae and P. terrestris; Coleoptera, such as Pseudocarabidae; Psychiatricidae, such as pine beetle; Pteridophyceae, such as cedar beetle; Etc .; Ossomopterae such as P. elegans; Lentinaceae such as scrofa beetle and stag beetle;
  • Hemiptera for example, aphid family such as Adomachio aphid; scorpionaceae family such as esomakasabura; marsupialidae family such as cedar marcay aphid; Can be mentioned.
  • Hymenoptera include, for example, honeybees, such as the stag beetle; honeybees, such as the pine sawfly; and honeybees, such as the chestnut wasp.
  • Examples of the dipterans include the genus Dermatidae, such as P. terrestris, the genus Dermatidae, such as L. japonicus, and the flies that include adults, larvae, and eggs.
  • spiders of the order Acarina examples include Suginohadani and Todoma nohadani.
  • the order of the Nematodes of the Nematodes of the Nematoda there may be mentioned, for example, Parasitadulenids, such as P. japonicus.
  • pests belonging to fungi include the following:
  • Ascomycetes such as powdery mildew fungi on various crops, rust fungi on various crops, basidiomycetes such as rice sheath blight fungi, oak fungi such as downy mildew fungi on various crops, plague fungi on various crops, Examples include incomplete fungi parasitic on various crops such as blast fungi and gray mold fungi.
  • the pesticidal composition containing the compound of the present invention as an active ingredient is a formulation effective in the agricultural and forestry situations described above, and any use form prepared by the formulation. It can be used alone or in combination with other active compounds such as insecticides, acaricides, nematicides, fungicides, synergists, plant regulators, herbicides, baits and the like, or as a mixture.
  • the form of use is arbitrary, for example, wettable powder, wettable powder, aqueous solvent, emulsion, liquid, suspension in water, flowable such as emulsion in water, capsule, powder, granule, aerosol, etc. Can be mentioned.
  • the content of the active ingredient compound such as the compound of the present invention in these preparations is arbitrary, but usually 0.001 to 95% by weight of the total amount of the active ingredients! 3 ⁇ 4, preferably 0.1 to 60% by weight.
  • the method of use depends on the type and amount of pests, the target crop, trees and other species, the cultivation form, and the state of growth.For example, for arthropods, gastropods, nematodes, etc.
  • 0.1 to 1000 g, preferably 1 to 100 g, of the active ingredient per 10 ares for the place where damage by these pests or the place where damage is likely to occur May be applied.
  • Specific application methods include, for example, the above-mentioned wettable powders, wettable powders for granules, aqueous solvents, emulsions, solutions, suspensions in water, and flowables such as emulsions in water, capsules, etc. It may be diluted and sprayed on crops, trees, etc. in the range of 10 to 1000 liters per 10 ares, depending on the type of crop, tree, etc., cultivation form, and growth condition. In the case of powders and aerosols, the preparations may be applied to crops, trees, etc. within the range of the above-mentioned usage.
  • the target pest mainly infects crops, trees, etc. in the soil, for example, wettable powder, wettable powder, aqueous solvent, emulsion, liquid, suspension in water, emulsion in water, etc.
  • the flowables, capsules, etc. can be diluted with water and applied generally in the range of 5 to 500 liters per 10 ares.
  • the medicine may be sprayed on the soil surface so as to be evenly applied to the entire application area, or the medicine may be irrigated into the soil.
  • the preparation When the preparation is in the form of a powder or granules, the preparation may be sprayed as it is on the soil surface so as to be uniform over the entire area to be applied. Seeds, crops and trees that you want to protect from pest damage during spraying or irrigation Or the like, or may be plowed during or after spraying to mechanically disperse the active ingredient.
  • a pesticidal composition containing the compound of the present invention as an active ingredient may be adhered around plant seeds by a known method. Such treatment not only prevents damage by pests in the soil after sowing the seeds, but also reduces the foliage, flowers, fruits, etc. of the plant from pest damage after growth. It can also be protected.
  • the pesticidal composition containing the compound of the present invention as an active ingredient may be used alone or with other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents, and synergists. Can be used in combination or as a mixture.
  • the content of the active ingredient compound such as the compound of the present invention in these preparations is arbitrary, but is usually 0.0001 to 95% by weight in total of the active ingredient, and is 0 in oils, powders, granules and the like. 005 to 10% by weight, preferably 0.01 to 50% by weight in emulsions, wettable powders, sols and the like. Specifically, for example, in the case of controlling and controlling termites and beetles, 0.01 to 100 g of the active ingredient compound per lm 2 may be sprayed on the soil or wood surface.
  • the pesticidal composition containing the compound of the present invention as an active ingredient is infested internally or externally with animals such as pets bred in the livestock industry, the fishery industry, and the home, and eats and sucks blood from the skin.
  • animals such as pets bred in the livestock industry, the fishery industry, and the home, and eats and sucks blood from the skin.
  • Effective for repelling, controlling and controlling pests such as arthropods, nematodes, trematodes, tapeworms, protozoa, etc. that cause direct harm such as spreading disease, etc. It can also be used to prevent and treat diseases associated with these pests.
  • Target animals include vertebrates, such as warm-blooded vertebrates such as cattle, sheep, goats, horses, pigs, and other livestock and farmed fish; and poultry, dogs, cats, etc., mice, rats, and hamsters. And rodents such as squirrels; carnivores such as felerets;
  • the following can be exemplified as the arthropod phylum Insecta and spider webs.
  • dipterans examples include flies of the order Aphid, such as Yamato-abu, ummet-gebubu, and akausiab; houseflies of the flies, such as blowfly, housefly and sandfly; engineering of the flies, such as the flies; Klopa's Technical Department; Oki Monno fruit fly and other flea fly departments; Families;
  • examples of the Laminoptera include fleas such as cat flea and flea flea.
  • examples of the lice include lice of the family Lepidoptera nits such as porcine lice and lice; lice of the genus Lepidoptera such as maji lice;
  • Examples of the acarids of the arthropod spiders include the family Acarinae, such as the ticks, Haemaphysalis longicornis, Ixodidae ticks, Oxodid ticks, Takasago Killing ticks, etc .; Examples of the family include the family Dermatophagoides, such as Cat Dermatophagoids and Pterodactyla;
  • the following can be illustrated as examples of the nematodes of the nematode phylum.
  • Examples of the order Coleoptera include hookworms, pig nematodes, pig lungworms, ciliate nematodes, and caterpillar nodules.
  • As roundworms for example, roundworm, roundworm, etc. Can be mentioned.
  • Examples of the flatworm fluke include, for example, Schistosoma japonicum, Hepatic fluke, Schistosoma japonicum, P. westermani, and Japanese egg fluke.
  • Examples of the tapeworm include foliate tapeworms, tapeworms, Beneden tapeworms, square tapeworms, striated tapeworms, and tapered tapeworms.
  • the order of the root flagellates is, for example, Histomonas
  • the order of the protoflagellate is, for example, Leishmania, Trypanosoma, etc.
  • the order of the multiflagellate is, for example, Giardia, etc., which is the order of Trichomonas. Is, for example, Trichomonas etc. ⁇
  • amoebices of the fleshytes for example, Entamoeba and the like
  • sporeworm Piroplasma subclasses for example, Theilaria, Babesia, and the like
  • live sporangial subclasses for example, Eimeria, Plasmodium ⁇ Toxoplasma, and the like.
  • the pesticidal composition containing the compound of the present invention as an active ingredient can be used alone or in another active compound such as an insecticide in a formulation effective in the livestock industry or the aquatic industry described above, and in any use form prepared by the formulation. It can be used in combination or as a mixture with acaricides, nematicides, fungicides, fungicides, synergists, plant regulators, herbicides and poison baits.
  • Specific methods of application include, for example, a mixed drug composition that can be mixed with feed for livestock pets or the like, or that can be orally ingested, such as tablets containing a pharmaceutically acceptable carrier and a coating substance, and pills. Tablets, capsules, pastes, gels, beverages, medicated feed, medicinal drinking water, medicated bait, sustained-release large pills, and other forms of oral administration such as sustained-release devices that are retained in the gastrointestinal tract It can be administered transdermally as a spray, powder, grease, cream, ointment, emulsion, lotion, spot-on, pore-on, shampoo and the like.
  • Methods for dermal and topical administration include devices attached to animals to control arthropods locally or systemically (eg, collars, medallion jars). —Tags) can also be used.
  • the amount of the active ingredient compound is generally 0.01 to 1.0 weight! 3 ⁇ 4, preferably 0.01 to 0.1% by weight.
  • capsules, pills or tablets containing a predetermined amount of the active ingredient are usually employed. These forms are used by uniformly mixing the active ingredient with a suitably comminuted diluent, filler, disintegrant and / or binder such as starch, lactose, talc, magnesium stearate, vegetable rubber, and the like. Manufactured.
  • a unit-use prescription may be determined by appropriately setting the weight and content of the anthelmintic according to the type of host animal to be treated, the degree of infection and the type of parasite, and the weight of the host.
  • the active ingredient compound When administered via feed, there may be mentioned, for example, a method in which the active ingredient compound is homogeneously dispersed in the feed, and a method in which the drug is used as a top dressing or in the form of a pellet.
  • the active ingredient compound is usually 0.0001 to 0.05% by weight in the final feed! 3 ⁇ 4, preferably 0.0005 to 0.01% by weight.
  • the active ingredient compound When dissolved or dispersed in a liquid carrier excipient, it may be administered parenterally to animals by intraruminal, intramuscular, intratracheal or subcutaneous injection. Because of parenteral administration, the active ingredient compound is preferably mixed with vegetable oils such as peanut oil and cottonseed oil. Such a formulation generally contains the active ingredient compound in an amount of 0.05 to 50% by weight, preferably 0.1 to 0.2% by weight. Preparations mixed with carriers such as dimethyl sulfoxide or hydrocarbon solvents may be sprayed or sprayed. By direct injection, it can be directly and locally administered to the external surface of a livestock animal.
  • the pesticidal agent containing the compound of the present invention as an active ingredient has adverse effects on clothes, food, and living environment, further harms the human body, and carries and transmits pathogens in public health situations and the like. It is also effective in repelling, controlling and controlling pests for maintaining public health.
  • the pesticidal composition containing the compound of the present invention as an active ingredient is, for example, a wood product such as a house itself or wood inside and outside thereof, wooden furniture, stored food, clothing, books, animal products (skin, hair, etc.). , Wool, feathers, etc.) and plant products (clothing, paper, etc.), etc., which have an adverse effect on hygienic life.
  • a wood product such as a house itself or wood inside and outside thereof, wooden furniture, stored food, clothing, books, animal products (skin, hair, etc.). , Wool, feathers, etc.) and plant products (clothing, paper, etc.), etc.
  • Lepidoptera beetles, spots, cockroaches, flies, mites, etc. It is effective for repelling, extermination and control.
  • Specific examples of pests in such a public health situation include the following.
  • arthropod phylum Insecta examples include the following.
  • Lepidoptera examples include, for example, the stag beetles such as P. sylvestris; the scrophaceae such as P. serrata; the stag beetles such as Aoiraga; the scrophulariaceae such as bamboo spiders; the scrophulariaceae such as scrophulariformes, s. And the family Kiroga, such as Iga and Koiga.
  • Pterodactylidae such as Akagamikirimidoki; Tsuchihanmidae such as Mamehanmyo; Scorpionidae such as Aobarigatahanekushi; Beetles, such as broad beetles; beetles, such as beetles; Beetles, etc .; Pterodactylidae, such as Coleoptera; Pterodactylidae, such as Coleoptera cricket, and Coleoptera cricket, and Pterodactylidae, such as Pterodactyla.
  • Hymenoptera examples include hornets, such as the wasp, hornet, etc .;
  • dipteran include dipteranaceae, such as japonicus, etc .; brassicaceae, such as brassicae; seriformes, such as sesjusuri force; buds, such as ashmadarabhu; fubs, such as housefly; houseflies, such as housefly; Rubiaceae; blowfly such as black fly; dirt fly technology such as cynomolgus fly; technical fly technology such as Drosophila melanogaster; cheesepa such as cheese fly;
  • Examples of the order Lepidoptera include a flea family such as flea flea.
  • the order of the viscera there may be mentioned, for example, the family Pentatomidae, such as purple pit viper.
  • the cockroaches include, for example, cockroaches such as German cockroaches and European cockroaches; cockroaches such as cockroaches, black cockroaches, and black cockroaches.
  • the Orthoptera includes, for example, the family Corrugidae, such as Madara Powered Madoma and Camadidae.
  • the louse includes, for example, lice of the head lice such as head lice; lice of the lice such as lice. Examples of the order Hemiptera include bed bugs such as bed bugs; and bugs such as red turtles.
  • the termites include, for example, the termites of the termites such as the termites and termites; the termites of the termites such as the termites; the termites of the termites, such as the termites of the termites. Department.
  • Examples of the order Staphylococcus include the family Staphylococci, such as black spots and sea lions.
  • arthropod spiders for example, ticks such as Schulz ticks; sarcastic mites such as house mites; sick mites such as Minamimite; two families of lice such as lice mites; two families of acrids such as two-spotted mites; Oxodidae; Dermatidae such as Akatsugamushi; Dermatidae such as Dermatophagoides farinae and Dermatophagoides farinae;
  • Examples of the genus Araneae include, for example, the spider family, such as the birch spider; the spider family, such as the spider spider; the spider family, such as the spider spider; the spider family; be able to.
  • the scorpiones there may be mentioned, for example, the scorpion family such as the scorpion.
  • examples of the order of the order Cymbiformes of the order of the order of the order Cymbiformes include the family Pseudopodaceae, such as Tobiz-mukade and Aozumkade.
  • Examples of the arthropod phylum, Ophiaceae include, for example, Phytopodaceae, etc.
  • examples of the arthropod phylum, Crustacea include, for example, Coleoptera, Coleoptera.
  • examples of the annelid fauna of the order Lepidoptera include, for example, the Lamaviridae such as Lamavir.
  • the pesticidal composition containing the compound of the present invention as an active ingredient can be used alone or in combination with other active compounds such as insecticides, acaricides in any of the above-mentioned preparations effective in public health, and in any use form prepared by the preparation. It can be used in combination or as an admixture with agents, nematicides, fungicides, synergists, plant regulators, herbicides, baits and the like.
  • the form of use is optional.For example, when protecting the above-mentioned animal products and plant products, apply oils, emulsions, wettable powders, powders, etc., install resin vaporizers, etc. It can be controlled by methods such as treatment, placement of granules, tablets and baits, and spraying of aerosol. Amount of active ingredient compound in these preparations Is preferably 0.0001 to 95% by weight.
  • Application methods include pests, such as arthropods that directly harm or arthropods that are vectors of disease, etc. Spraying, injection, irrigation, application, dusting, etc., fumigants, mosquito coils, self-burning type smokers, heating fogs such as chemical reaction type aerosols, fogging etc., ULV agents, etc. And the method of treatment with such a preparation. In addition, they are applied in other forms such as granules, tablets or poison bait, or by dripping floating powder, granules, etc. into waterways, wells, reservoirs, water tanks and other running or stationary water. Just do it.
  • mites which are pests that are also pests in agriculture and forestry, in the same manner as described above. It is also effective to mix the active ingredient, and for power, etc., to volatilize into the air with an electric mosquito trap.
  • formulations in these forms of use can also be present as a mixture with other active compounds, for example insecticides, acaricides, nematicides, fungicides, repellents or synergists, These preparations preferably contain the active ingredient compound in a total amount of 0.0001 to 95% by weight.
  • the compounds of the present invention may be used alone or in combination with other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents, synergists and the like or as a mixture. You can do it.
  • the content of the active ingredient compound such as the compound of the present invention in these preparations is arbitrary, but is usually 0.0001 to 95% by weight of the total amount of the active ingredient, and For powders, granules, etc. 005 ⁇ 10 weight! 3 ⁇ 4, emulsions, wettable powders, sols and the like are preferably used in an amount of 0.01 to 50% by weight. Specifically, for example, in the case of controlling and controlling termites and beetles, 0.01 to 100 g of the active ingredient compound per im 2 may be sprayed around or directly on the surface.
  • Repelling and controlling pests such as causing harm to the human body or carrying or transmitting pathogens *
  • appropriate orally ingestible preparations such as pharmaceutical compositions Tablets, pills, capsules, pastes, gels, beverages, medicated feed, medicated drinking water, medicated bait, sustained-release large pills, and other drugs that contain an acceptable carrier-coating substance It can be administered orally as a sustained-release device or the like, or transdermally as a spray, powder, grease, cream, ointment, emulsion, mouth lotion, spot-on, pour-on, sham, etc.
  • the compound of the present invention can be used in combination with other active compounds or as a mixture.
  • the following compounds can be exemplified as more specific active compounds.
  • organic phosphorus agents include, for example, dichlorvos, phennitrothion, malathion, naled, chlorpyrifos, diazinon, tetrachlorvinphos, fenthion, isoxathion, methidathion, salithion, acephite, Dimethon-S-methyl, disulfone, monocrotophos, azinphosmesyl, parathion, hosalone, pirimiphosmethyl, prothiophos and the like.
  • carbamate examples include metocalp, fenobucalp, propoxur, carbaryl, ethiofencalp, pirimicarb, vendiocalp, carbosulfan, carbofuran, mesomil, thiodicarp and the like.
  • Organic chlorine agents include, for example, lindane, DDT, endosulfan, aldo Phosphorus, chlordane and the like can be mentioned.
  • Pyrethroids include, for example, permethrin, cypermethrin, deltamethrin, cyhalothrin, sifnoretrin, aclinatrin, fenvalerate, ethoplumprox, silafluofon, fulvalinate, flucitrinate, biphentrin, arrestrin, phenothrin, phenothrin, phenothrin, and phenothrin .
  • Trilin, siphenothrin, framethrin, resmethrin, transfluthulin, prauretrin, funoreffenprox, halofanprox, imiprotrin and the like can be mentioned.
  • neonicotinoid agents include imidacloprid, nitrene bilam, acetamiprid, tefuranitodine, thiamethoxam, thiacloprid and the like.
  • insect growth regulators such as phenylbenzoyl perea agents include diflubenzuron, black fluazuron, triflumuron, flufenox, hexaflumuron, norefopenuron, tefluvenzuron, buprofezin, tebufenozide, chromafufenozide, methoxifozinozide And the like.
  • juvenile hormone preparations include pyriproxyphen, fanoxycarb, mesoprene, and hydroprene.
  • Insecticidal substances produced by microorganisms include, for example, abamectin, minorebemectin, nikkomycin, emamectin benzoate, ibenoremectin, spinosad and the like.
  • insecticides include, for example, cartap, bensultap, chlorfenapyr, diafanturon, nicotine sulfate, metaldehyde, fipronil, pimetrozine, indoxacarp, tolfenpyrad and the like.
  • Active compounds for acaricides include, for example, dicophor, phenylisobromolate, benzomate, tetradiphone, polynactin complex, amitraz, propargyl, fenbutatin oxide, tricyclohexyltin hydroxide, tebufe
  • Examples include pyridine, pyridaben, fenpyroximate, pyrimidifene, fenazaquin, clofentezine, hexthiazox, acequinosyl, quinomethionate, pentochalp, ethoxazole, and bifenazetate.
  • nematicide active compound examples include, for example, methyl isocyanate, phosphatiazetate, oxamil, mesulfonphos and the like.
  • Examples of the bait include monofluoroacetic acid, perfurin, coumatetralyl, difacine and the like.
  • Active compounds of fungicides include, for example, inorganic copper, organocopper, sulfur, maneb, thiuram, thiadiazine, capbutane, chlorothalonil, iprobenphos, thiophanate methyl, benomyl, thiabendazole, iprodione, prosimidon, pencyclon, metalaxyl, sandphan, Niletone, triflumizole, finarimol, triforine, dithianone, triazine, fluazinam, probenazole, dietophanolcap, isoprothiolane, pyroquilon, iminoctadine acetate, echromezol, dazomet, cresoxime methyl, etc. .
  • active compounds such as herbicides include bialaphos, sethoxydim, trifluralin, mefunaset and the like.
  • active compounds for plant regulators include indolebutyric acid, ethephon, 4-CPA and the like.
  • Active compounds of repellents include, for example, karan-3,4-diol, N, N-ethyl-m-triamide (Deet), limonene, linalool, citronellal, menthone, hinokitiol, menthol, graniol, eucalyptol And the like.
  • Examples of the active compound of the synergist include bis- (2,3,3,3-tetrachloropropyl) ether and N- (2-ethylhexyl) bisc [2,1,1] hept-5- 2,3-dicarboxyimide, ⁇ - [2- (2-butoxyethoxy) ethoxy] -4,5-methyl And Rhenoxy-2-propyltoluene.
  • the compound of the present invention when used as an active ingredient of a herbicide, the compound of the present invention may be administered as it is, but usually, the active ingredient and an agricultural chemical adjuvant commonly used in the art are used. It is preferably formulated and used in the form of a composition.
  • the form of the preparation is not particularly limited, but is preferably in the form of, for example, emulsion, wettable powder, powder, floor pull, fine granule, granule, jumbo, tablet, oil, spray, aerosol, etc. It is. Incidentally, a mixture of two or more optical isomers may be used as the active ingredient.
  • a pesticide adjuvant may be used for the purpose of improving the effect of the herbicide, stabilizing it, improving the dispersibility, and the like.
  • the pesticidal auxiliary include a carrier (diluent), a spreading agent, an emulsifier, a wetting agent, a dispersant, a disintegrant, and the like. More specifically, the carrier includes a liquid carrier and a solid carrier.
  • liquid carrier examples include aromatic hydrocarbons such as water, toluene, and xylene; alcohols such as methanol, butanol, and glycol; ketones such as acetone; amides such as dimethylformamide; and sulfoxides such as dimethyl sulfoxide. And the like; methylnaphthalene, cyclohexane, animal and vegetable oils, fatty acids and the like.
  • solid carrier sauce, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, arabia rubber and the like can be used.
  • Usable surfactants can be used as emulsifiers and dispersants.
  • anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkyl phenyl ether, lauryl betaine, cationic surfactant, nonionic surfactant, amphoteric An ionic surfactant or the like can be used.
  • spreading agent for example, polyoxyethylene nonylphenyl ether, polyoxyethylene lauryl ether, etc., as a wetting agent, polyoxyethylene nonylphenyl ether, dialkyl sulfosuccinate, etc., and as a fixing agent, carboxymethyl cellulose, polyvinyl chloride.
  • Alcohol and the like can be used, and as a disintegrant, sodium lignin sulfonate, sodium lauryl sulfate and the like can be used.
  • As other pesticidal auxiliaries for example, those described in Japan Kokai Tokkyo Koho JP60 / 25986 (Chemical Abstracts 103: 87762s) can be used.
  • the content of the active ingredient in the formulation is usually 0.5 to 90% by weight, and the content of the pesticide adjuvant is 10 to 99.5% by weight! 3 ⁇ 4, which may be appropriately selected depending on various conditions such as the form of the preparation and the method of application.
  • Herbicides containing the compound of the present invention as an active ingredient include, in addition to the active ingredient and the aforementioned pesticide adjuvants, other fungicides for agricultural and horticultural use, insecticides, herbicides, plant growth regulators, fertilizers, soil conditioners, and pesticides.
  • An arbitrary active ingredient such as an acaricide may be contained. Further, it may be mixed or applied simultaneously with such other pesticides.
  • the application rate of the herbicide of the present invention may be appropriately selected depending on conditions such as the type of the active ingredient, the target weed, the treatment period, the treatment method, or the properties of the soil, but is usually 1 hectare.
  • the active ingredient may be used in an amount of 10 to 5000 g, preferably 50 to 2000 g.
  • the treatment method of the herbicide containing the compound of the present invention as an active ingredient is also optional.
  • weeds can be controlled by any method such as soil treatment before germination, foliage treatment at the growing stage, and flooding treatment.
  • the herbicide of the present invention may be a weed of interest, for example, an annual weed such as Mehishiba, Ohishiba, Nobie, Inubie, Tainubie, Enokorogusa, etc .; a weed of the family Calypsa, Tamagayari, Firefly, Matsubai, etc .; , Inubu, Aobu, Inuyu-de, No, Le Tade, Hakobe, Hotokenoza, Ichibi, Onamomi, Wild Asagao, Chiyosen Asagao, Wild Karasina, Yaemdara, Seiyosumire, Oroshagiku, It is effective against annual and perennial broadleaf weeds such as kosendangusa, azen
  • the herbicide containing the compound of the present invention as an active ingredient has high selectivity to cultivated crops such as the aforementioned food crops, vegetables and special crops.
  • the herbicide containing the compound of the present invention as an active ingredient can significantly increase the width of herbicidal spectrum when used in combination with other herbicides. This can provide, for example, a herbicide that effectively acts on the growing annual broadleaf weeds and perennial weeds, and further stabilizes the herbicidal effect.
  • Examples of the herbicide that can be suitably mixed with the herbicide of the present invention include the following herbicides (generic names or development code numbers). However, the herbicides that can be suitably mixed are not limited to these.
  • chloroacetamide herbicides such as arlacrol, metrachlor, and acetochlor
  • carbamate herbicides such as trialate
  • dinitroaniline herbicides such as trifluralin and pendimethalin
  • diclohop-methinole such as Trifluralin and pendimethalin
  • ⁇ ⁇ Phenoxypropionate herbicides such as Noxaprop-ethyl, Fluazifop-butyl, and Quizalofop-ethyl
  • cyclohexandione herbicides such as sethoxydim, clesodime, tralkoxydim, butroxydim
  • herbicides such as diflufenican and UBH-820 Amide herbicides
  • Sulfonamide herbicides such as Flumelam
  • Sulfonyl perrea herbicides such as halosulfo-methyl
  • Imidazolinone herbicides such as imazaquin
  • triazine herbicides such as atrazine, cyanadine, metrifudine, etc .
  • urea herbicides such as chlorotoluron, isoprolon, diuron, linuron, and flumelam
  • Sulfonylprea herbicides Sulfonylprea herbicides; imidazolinone herbicides such as imazethapyr, imazamox and imazameyu pill; amide herbicides such as dimethenamid; flumioxazine, isoxaflutol, sul'cotrione, norflurazon, cromazone, JV485 Herbicides such as (isopropazole) can be exemplified.
  • organophosphorus herbicides such as glyphosate, glufosinate, and bialaphos
  • herbicides such as paraquat
  • chloroacetamide herbicides such as butachlor, pretilachlor, and tenylchlor
  • mefenacet, fenfentrol Amide herbicides such as ethobenzanide, NBA-061 (pentrazamide) and propanil
  • phenoxypropionate herbicides such as cyhalofop-butyl
  • carbamates such as benthiocarb, esprocalp, molineto and piribuchicarb Herbicides
  • Herbicides such as oxadiclomefone and pyrimino-noc-methyl can be exemplified.
  • sulfonylurea herbicides such as bensulfuron-methyl, birazosulfuron-ethyl, imazosulfuron, cyclosulfamuron, sinosulfuron, ethoxysulfuron, azimsulfuron, and halosulfuron-methyl; nabroanilide, clomeprop, MCP, MCP Penoxy herbicides such as MCPA; pyrazolates, birazoxifen, benzophenap, etc .; virazolate herbicides such as bifenox; diphenyl ether herbicides such as bifenox; herbicides such as oxaziargyl and pentoxazone; and promob Examples include amide herbicides such as tide; urea herbicides such as Daimlon and cumyluron; and herbicides such as Benfreset and SB-500.
  • Example Example 1 1 To a suspension of sodium hydride (60 oily, 8.00 g, 0.20 mol) in DMF (150 mL) was added ethyl 3-ethylamino-4-, 4,4-trifluorochlorotonate while stirring under ice-cooling. 36.6 g, 0.20 mol was added, and the mixture was stirred at the same temperature for 30 minutes.
  • Example one 3 A suspension of sodium hydride (60% oil, 2.35 g, 59. Ommol) in DMF (60 mL) was stirred at 0 ° C while stirring 3-ethylamino-4,4,4-trifluoroethyl mouth tolate (7.33 g). , 49. lMiol). After keeping the reaction solution at 0 ° C and stirring for 30 minutes, slowly add 4-chlorophenylisothiocyanate (10. Og, 59. Ommol) overnight while slowly returning the reaction temperature to room temperature. Stirred.
  • Example 1 4 While stirring a suspension of sodium hydride (60% oily, 0.62 g, 15.4 mmol) in DMF (50 mL) at 0 ° C, the mixture was stirred with 3-amino-4,4,5,5,5-pentafluoro-2-. Pentenoic acid Nore (3.00 g, 12.9 mmol) was added slowly. After keeping the reaction solution at 0 ° C and stirring for 30 minutes, 4-chlorophenylisothiocyanate (2.62 g, 15.4 mmol) was slowly added, and the reaction temperature was gradually raised to room temperature. Stirred overnight.
  • reaction solution was poured into dilute hydrochloric acid (50 mL), and the aqueous layer was extracted with ethyl acetate (100 mL). The extract was washed with water (50 raL) and a saturated aqueous sodium chloride solution (30 mL), and dried over anhydrous magnesium sulfate. After the desiccant was removed by filtration, the filtrate was concentrated under reduced pressure to obtain a crude product of 2,6-dichloro-4- (trifluoromethyl) phenylisothiocyanate.
  • Example 11 As in Example 1, 3-amino-4,4,4-trifluorochlorotonate (3.65 g, 24.5 dragonol) and 2-chloro-5-isothiocyanatoethyl benzoate (7.10 g, 29.4 mniol) ) To give 3- ⁇ 4-chloro-3- (ethoxycarbonyl) phenyl ⁇ -2-mercapto-6-trifluoromethyl-4 (3H) -pyrimidinone as a white solid (4.20 g). Was. Yield: 45%; Melting point: ⁇ . ; 1 !!
  • Example one 32 Example one 32
  • Example—Similar to Example 30, 3- (4-bromophenyl) -2-mercapto-6-trifluoromethyl-4 (3H) -pyrimidinone (10.7 g, 30.4 mmol) was reacted with methyl iodide (2.8 4 mL). The resulting crude product was purified by a silica gel column (Co-gel C-200, ethyl acetate: hexane 1: 8) to give 3- (4-promophenyl) -2-methylthio-6- A white solid (10.5 g) of trifluoromethyl-4 (3H) -pyrimidinone was obtained. Yield: 94%; Melting point: a ⁇ ⁇ . ; 1 !!
  • Example 1 Similarly to 30, 3- (2,4-dichlorophenyl) -2-mercapto-6-trifluoromethyl-4 (3H) -pyrimidinone (3.18 g, 9.33 mmol) and methyl iodide (0.90 ), And the resulting crude product is recrystallized from toluene to give 3- (2,4-dichlorophenyl) -2-methylthio-6-trifluoromethyl-4 (3H) -pyri A white solid of midinone (2.83 g) was obtained.
  • Example 1 In the same manner as in Example 30, 3- (3,5-dichlorophenyl) -2-mercapto-6-trifluoromethyl-4 (3H) -pyrimidinone (1.88 g, 5.51 bandol) and methyl iodide (0.52 mL) ), And the resulting crude product is recrystallized from toluene to give 3- (3,5-dichlorophenyl) -2-methylthio-6-trifluoromethyl-4 (3H) -pyri A white solid of midinone (1.91 g) was obtained. Yield: 98%; mp: 167 ⁇ 170 ° C; 1 !!
  • Example 1 Similarly to 30, 3- (5-indanyl) -2-mercapto-6-trifluoromethyl-4 (3H) -pyrimidinone (4.00 g, 12.8 marl) and methyl iodide (1.04 mL)
  • Example-30 Except that acetonitrile was used as the solvent, the procedure of Example-30 was repeated, except that 2-mercapto-3- (2-methyl-4-ditrophinyl) -6-trifluoromethyl-4 (3H) -pyrimidinone ( By reacting 3.69 g, 11.1 ol) with methyl iodide (0.83 DIL), 3- (2-methyl-4-nitrophenyl) -2-methylthio-6-trifluoromethyl-4 (3H) -pyrimidinone was blackened. A solid (3.84 g) was obtained. Yield: 983 ⁇ 4; mp: 14 ⁇ ⁇ :; 1 !!
  • Example 1 Similarly to 30, 2-mercapto-3- ⁇ 4- (trifluoromethyl) phenyl ⁇ -6-trifluoromethyl-4 (3H) -pyrimidinone (3.31 g, 9.71 mmol) Methyl dioxide (0.90 mL) was reacted, and the obtained crude product was recrystallized from toluene to give 2-methylthio-3- ⁇ 4- (trifluoromethyl) phenyl ⁇ -6-trifluoromethyl-4 A white solid (3. Olg) of (3H) -pyrimidinone was obtained. Yield: 88; 3 ⁇ 4; melting point 24-127. ?
  • Example 1 In the same manner as in Example 30, 2-mercapto-3- (4-phenyloxyphenyl) -6-trifluoromethyl-4 (3H) -pyrimidinone (4.89 g, 13.4 bandol) and methyl iodide (1.25 mL), and the resulting crude product was recrystallized from toluene to give 2-methylthio-3- (4-phenoxyphenyl) -6-trifluoromethyl-4 (3H) -pyrimidinone A white solid (4.62 g) was obtained.
  • Example 13 Except that acetonitrile was used as the solvent, the procedure of Example 13 was repeated, except that 3- (3-methylthiophenidyl) -2-mercapto-6-trifluoromethyl-4 (3H) -pyrimidinone (5.00 g) was used. , 15.7 mmol) and methyl iodide (1.27 mL) to give 2-methylthio-3- (3-methylthiopheninole) -6-trifluoromethyl-4 (3H) -pyrimidinone black. An oil was obtained.
  • Example 30 Except that acetonitrile was used as the solvent, the same procedure was followed as in Example 30 to give the 2-meth- By reacting rucapto-3-(trifluoromethylthio) phenyl ⁇ -6-trifluoromethyl-4 (3H) -pyrimidinone (3.OOg, 8.06mmol) with methyl iodide (0.65mL), A black oil (2.74 g) of methylthio-3- ⁇ 3- (trifluoromethylthio) phenyl) -6-trifluoromethyl-4 (3H) -pyrimidinone was obtained. Yield ⁇ ⁇ ; 1 !!
  • Example 30 Except that acetonitrile was used as the solvent, the procedure of Example 30 was repeated, except that 2-mercapto-3- ⁇ 3- (trifluoromethylsulfonyl) phenyl ⁇ -6-trifluoromethyl-4 (3H) -pyrimidinone (2 OOg, 4.95 mmol) and methyl iodide (0.40 mL) to give 2-methylthio-3_ ⁇ 3- (trifluoromethylsulfonyl) phenyl ⁇ -6-trifluoromethyl-4 (3H).
  • -A yellow oily substance of pyrimidinone (1.16 g) was obtained. Yield:! ⁇ ⁇ 1 !!
  • Example 1 In the same manner as in Example 30, 2-mercapto-3- (4-nitrophenyl) -6-trifluoromethyl-4 (3H) -pyrimidinone (5.40 g, 17.0 ol) and methyl iodide (1.6 OniL) were used. The resulting crude product was recrystallized from toluene to give 2-methylthio-3- (4-ditrophenyl) -6-trifluoromethyl-4 (3H) -pyrimidinone as a white solid (3.63 g). I got Yield: 64%; mp:!
  • 2,5-Bis (trifluoromethinole) aniline (3.00 g, 13.2 mmol) was dissolved in DMF (30 mL), sodium hydride (0.56 g, 14.1 mmol) was added, and the mixture was stirred at room temperature. After 30 minutes, 2-methylsulfonyl-3-phenyl-6-trifluoromethyl-4 (3H) -pyrimidinone (3.00 g, crude) was added, and the mixture was further reacted for 4 hours. After completion of the reaction, the reaction solution was diluted with ether, and excess sodium hydride was neutralized with a saturated aqueous solution of ammonium chloride, and the aqueous layer was removed.
  • the aqueous layer was extracted with ether, and the organic layers were combined, washed twice with a saturated aqueous sodium hydrogen carbonate solution and sequentially with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After filtering off the drying agent, the solvent was distilled off from the filtrate under reduced pressure.
  • Example 1 Similarly to 63, 4-ditroaniline (0.55 g, 4.00 mmol) and 2-methylthio-3-phenyl-6-trifluoromethyl-4 (3H) -pyrimidinone (1.60 g, Five .59 mmol), and the resulting crude product was recrystallized from toluene to give 2- (4-ditropheninole) amino-3-phenyl-6-trifluoromethyl-4 (3H) -pyrimidinone A pale yellow solid (1.13g) was obtained. Yield: 75!
  • Example 1 Similarly to 66, 2- (4-ditrophenyl) amino-3-phenyl-6-trifluoromethyl-4 (3 ⁇ ) -pyrimidinone (0.38 g, 1, OO mmol) and sulfuryl chloride (0.08 mL) And the resulting crude product is recrystallized from toluene to give 5-chloro-2- (4-ditrophenyl) amino-3-phenyl-6-trifluoromethyl-4 (3H) -pyrimidinone. A pale yellow solid (0.28 g) was obtained. Yield: 67; mp:!?
  • Example 1 As in Example 66, 2- ⁇ 2,4-bis (trifluoromethylinole) phenyl ⁇ amino-3- (4-fluorophenyl) -6-trifluoromethyl-4 (3H ) -Pyrimidinone (0.60 g, 1,24 ol) and sulfuryl chloride (0.09 raL) were reacted, and the resulting crude product was converted to a silica gel column ( ⁇ -gel C-200, ethyl acetate).
  • Example 1 As in Example 6, 6- ⁇ 2-chloro-3,5-bis (trifluoromethyl) phenyl ⁇ amino-3- (4-chloropheninole) -6-trifluoro Orthomethyl-4 (3H) -pyrimidinone (0.70 g, 1.31 mmol) is reacted with sulfuryl chloride (0.10 mL), and the resulting crude product is subjected to a silica gel column (Co-gel C-200, chromatography).
  • Example 1 Similarly to 63, 2,4-bis (trifluoromethyl) aniline (1.24 g, 5.4211111101) and 3- (4-chloro-2-fluoro-5-methoxyphenyl) -2-methylthio- 6-Trifluoromethyl_4 (3H) -pyrimidinone (2.00 g, 5.42 mmol) was reacted, and the resulting crude product was subjected to a silica gel column (cogel C-200, ethyl acetate: hexane).
  • Example 1 As in the case of 3, 2-bromo-3,5-bis (trifluoromethyl) aniline (2.60 g, 8.66 mmol) and 3- (2,4-dichlorophenyl) -2-methylthio -6-Trifluoromethyl-4 (3H) -pyrimidinone (4.00 g, 11.3 mmol) is reacted and the resulting crude product is subjected to silylation gel ram ( ⁇ co-gel C-200, ethyl acetate: hexane).
  • Example 1 As in Example 6, 2- ⁇ 2-bromo-3,5-bis (trifluoromethyl) phenyl) amino-3- (2,4-dichlorophenyl) -6-trifluoromethyl -4 (3H)-Pyrimidinone (0.66 g, 1.07 mmol) is reacted with sulfuryl chloride (0.09 mL), and the resulting crude product is subjected to a silylation gel column ( ⁇ -gel C-200, ethyl acetate: hexyl).
  • Example 1 As in 66, 2- ⁇ 2,4-bis (trifluoromethyl) phenyl ⁇ amino-3- (3,4-dichlorophenyl) -6-trifluoromethyl-4 (3H ) -Pyrimidinone (0.56 g, 1.04 mmol) is reacted with sulfuryl chloride (0.08 mL), and the resulting crude product is subjected to silylation gel ram ( ⁇ Ko-gel C-200, ethyl acetate: hexane).
  • Example 1 As in Example 66, 2- ⁇ 2,4-bis (trifluoromethyl) phenyl) amino-3- (3,5-dichlorophenyl) -6-trifluoromethyl-4 (3H) -pyri
  • Example 1 As in Example 63, 2-nitro-4- (trifluoromethyl) aniline (0.45 g, 2.34 ol) and 3- ⁇ 2,6-dichloro-4- (trifluoromethyl) phenyl) -2 -Methylthio-6-trifluoromethyl-4 (3H) -pyrimidinone (1.00 g, 2.36 bandol), and the resulting crude product was subjected to a silica gel column (Kieselgel 60, Merck).
  • Example 1 As in Example 6, 2- ⁇ 2,4-bis (trifluoromethyl) phenyl ⁇ amino-3- (2-cyclo-4-methylsulfonylphenyl) -6-trifluoromethyl-4
  • sulfuryl chloride 350 mg, 2.59 mrao 1
  • Example 106 except that N-bromosuccinimide was used as the halogenating agent 2- ⁇ 2,4-bis (trifluoromethyl) phenyl ⁇ amino-3- (2-chloro-4-methylsulfonylphenyl) -6-trifluoromethyl-4 (3H) -Pyrimidinone (l.OOg, 1.73 mmol) is reacted with N-bromosuccinic acid imide (460 mg, 2.59 dragonol), and the resulting crude product is subjected to a silica gel column (Merck Kieselgel 60, acetate).
  • Example 1 Similarly to 63, 2,4-bis (trifluoromethyl) aniline (0.67 g, 2.94 bandol) and 3- ⁇ 4-chloro-3- (ethoxycarbonyl) phenyl ⁇ -2- Methylthio O-6-Trifluoromethyl-4 (3H) -pyrimidinone (3.82 g, 3.82 bandol) was reacted with the resulting crude product, and the resulting crude product was treated with a silica gel ram ( ⁇ ⁇ -gel C-200).
  • a silica gel ram ⁇ ⁇ -gel C-200
  • Example 1 As in 63, 2,4-bis (trifluoromethyl) aniline (1.69 g, 7.38 mmol) and 3- (4-1-butylphenyl) -2-methylthio-6_trifluoromethyl- 4 (3H) -Pyrimidinone (2.68 g, 7.77 mmol) and the resulting crude product was recrystallized from a toluene-hexane mixed solution to give 2- (2,4-bis (trifluoromethyl).
  • Example 1 As in 66, 2- ⁇ 2,4-bis (trifluoromethyl) phenyl ⁇ amino-3- (4-t-butylphenyl) -6-trifluoromethyl-4 (3H) -pyrimidino (700 mg, 1.33 mmol) and sulfuryl chloride (270 mg, 2.00 mmol), and the resulting crude product was recrystallized from a toluene-hexane mixed solution to give 2- ⁇ 2,4 A white solid (600 mg) of -bis (trifluoromethyl) phenyl ⁇ amino-3- (4- 1-butylphenyl) -5-chloro-6-trifluoromethyl-4 (3H) -pyrimidinone was obtained. Yield:.
  • 2- ⁇ 2,4-bis (trifluoromethyl) phenyl ⁇ amino-3- (4-t) was prepared in the same manner as in Example-106 except that N-bromosuccinimide was used as the halogenated compound.
  • N-bromosuccinimide was used as the halogenated compound.
  • -Butylphenyl) -6-trifluoromethyl-4 (3H) -pyrimidinone (700 mg, 1.33 minol) and N-bromosuccinic acid imide (360 mg, 2.0 mmol) are obtained.
  • the resulting crude product was recrystallized from a mixed solution of toluene and hexane to give 2- ⁇ 2,4-bis (trifluoromethyl) phenylinole) amino-5-bromo-3- (4-butylbutylinole).
  • Example 1 Similarly to 66, 2- ⁇ 2,4-bis (trifluoromethyl) phenyl ⁇ amino-3- (4- (ethoxycarbonyl) phenyl ⁇ _6-trifluoromethyl_4 (3H) -pyrimidino ( 700 mg, 1.30 bandol) and sulfuryl chloride (260 mg, 1.94 mmol) were reacted with each other, and the resulting crude product was recrystallized from a mixed solution of toluene and hexane to give 2- ⁇ 2,4-bis (toluene).
  • Example 1 As in 66, 2- ⁇ 2,4-bis (trifluoromethyl) phenyl) amino-3- (4-methoxyphenyl) -6-trifluoromethyl-4 (3H)
  • 2- ⁇ 2,4-bis (trifluoromethyl) was obtained.
  • a white solid (0.39 g) of methinole) phenyl) amino-5-chloro-3- (4-methoxyphenyl) -6-trifluoromethyl-4 (3H) -pyrimidinone was obtained.
  • Example 1 As in 63, 2-nitro-4- (trifluoromethyl) aniline (0.65 g, 3.16 face ol) and 3- (4-methoxyphenyl) -2-methylthio-6-trifluoromethyl -4 (3H) -pyrimidinone (1.49 g, 4.74 ol) and the resulting crude product was recrystallized from toluene to give 3- (4-methoxyphenyl)-2- ⁇ A yellow solid (1.06 g) of 2-nitro-4- (trifluoromethyl) phenyl ⁇ amino-6-trifluoromethyl-4 (3H) -pyrimidinone was obtained.
  • Example 1 Similar to 66, 2- ⁇ 2-nitro-4- (trifluoromethyl) phenyl ⁇ amino-3- (4-phenyloxy) -6-trifluoromethyl-4 (3H) -Pyrimidinone (0.75g, 1.31mfflol) is reacted with sulfuryl chloride (0.1mL), and the resulting crude product is purified using a silica gel ram ( ⁇ ⁇ Ko-Igel C-200, toluene). To give 5-chloro-2--2- ⁇ 2-nitro-4- (trifluoromethyl) phenyl ⁇ amino-3- (4-phenoxyphenyl) -6-trifluoromethyl-4 (3H A yellow solid of () -pyrimidinone was obtained (0.36 g).
  • Example 1 Similarly to 63, 2,4-bis (trifluoromethyl) aniline (3.28 g, 14.3 mmol) and 2-methylthio-3- (4-methylthiophenidyl) -6-trifluoromethyl-4 (3H ) -Pyrimidinone (5.00 g, 15.1 mmol), and the resulting crude product was recrystallized from aqueous ethanol and isopropyl alcohol to give 2- ⁇ 2,4-bis (trifluoro A white solid (4.80 g) of (trifluoromethyl) phenyl ⁇ amino-3- (4-methylthiophenyl) -6-trifluoromethyl-4 (3H) -pyrimidinone was obtained. Yield: 62%; Melting point: 180.
  • Example 1 In the same manner as in 63, 2-methylthio-3- ⁇ 4- (trifluoromethylthio) phenyl ⁇ -6-trifluoromethyl-4 (3H) -pyrimidinone (1.20 g, 3.11 mmol) and 2 , 4-bis (trifluoromethyl) aniline (712 mg, 3.
  • Example 1 Similarly to 63, 2-methylthio-3- ⁇ 3- (trifluoromethylsulfonyl) phenyl ⁇ -6-trifluoromethyl-4 (3H) -pyrimidinone (1.28 g, 3. 06 t) and 2,4-bis (trifluoromethyl) aniline (701 mg, 3.06 IMIO1), and the resulting crude product is converted to a silica gel column ( ⁇ -gel C-200, ethyl acetate: 2- (2,4-bis (trifluoromethyl) phenyl) amino-3- (3- (trifluoromethylsulfonyl) phenyl) -6-trifluoromethyl A white solid of -4 (3H) -pyrimidinone was obtained (548 mg).
  • Example 1 Similarly to 66, 2- ⁇ 2,4-bis (trifluoromethyl) phenyl ⁇ amino-3- (4-ditrophenyl) -6-trifluoromethyl-4 (3H) -pyrimidinone (0.30 g, 0.59 ramol) and sulfuryl chloride (0.05 mL).
  • 2- (2,4-bis (trifluoromethylinole) phenol A white solid (0.23 g) of ⁇ amino-5-chloro-3- (4-ditrophenyl) -6-trifluoromethyl-4 (3H) -pyrimidinone was obtained.
  • Example 1 As in Example 66, 2- ⁇ 2-chloro-3,5-bis (trifluoromethyl) phenyl) amino-3-(-naphthyl) -6-trifluoromethyl-4 (3H) -pyri Reaction of midinone (l.OOg, 1.81 mmol) with sulfuryl chloride (0.15 mL) and purification of the resulting crude product on a silica gel column ( ⁇ -gel C-200, toluene).
  • Example—Similar to 16.1, 4-fluoroaniline (470 mg, 4.65 mmol) and 2-methylthio-16-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone (l.OOg, 4.23 mmol), and the resulting crude product is treated with silica. Purification with a gel column ( ⁇ -gel C-200, ethyl acetate: hexane 1: 2) yields 2- (4-fluorophenyl) amino-6-trifluoromethyl-3-vinyl-4 (3H) 1-pyrimidinone brown A solid was obtained.
  • Example 1 As in the case of 61, 3,5-difluoroaniline (1.09 g, 8.44 mmol) and 2-methylthio-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone (2. 00g, 8.47 mmol), and the obtained crude product was recrystallized from ethanol to give 2- (3,5-difluorophenyl) amino-6-trifluoromethyl-3-vinyl-4 ( Light yellow crystals of 3H) -pyrimidinone were obtained.
  • Example 16 As in the case of 61, 4-bromo-2-fluoroaniline (374 mg, 4.65 mmol) and 2-methylthio-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone (1.00 mg) g, 4.23 mmol) to give a brown solid of 2- (4-bromo-2-fluorophenolinole) amino-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone.
  • Example 16 As in the case of 61, 4-fluoro-2-nitroaniline (1.32 g, 8.47 mmol) and 2-methylthio-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone ( 2.00 g, 8.47 mmol), and the obtained crude product was recrystallized from ethanol to give 2- (4-fluoro-2--2-nitrophenyl) amino-6-trifluoromethyl-3-vinyl- 4 (3H) -Pyrimidinone yellow crystals were obtained. Yield: 60%; Melting point: a ⁇ . . ; 1 !!
  • Example 1 As in the case of 61, 2,4-dichloroaniline (689 mg, 4.65 mmol) and 2-methylthio-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone (1.00 g, 4.23 mmol) To give 2- (2,4-dichlorophenyl) amino-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone as a pink solid. Yield: 50%; mp: ⁇ ⁇ ⁇ ⁇ ; 1 !!
  • Example 1 As in the case of 61, 2,6-dichloroaniline (685 mg, 4.65 marl ol) and 2-methylthio-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone (1.00 g, 4.23 ramol), and the resulting crude product was recrystallized from ethanol to give 2- (2,6-dichlorophenyl) amino-6-trifluoromethyl-3-vinyl-4 (3H White crystals of) -pyrimidinone were obtained. Yield: 34%; mp: 162 ⁇ 16 ⁇ ⁇ ; 1 !!
  • Example 1 As in the case of 61, 3-amino-4-chlorobenzobenzotrifluoride (827 mg, 4.65 mmol) and 2-methylthio-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone (1.00g, 4.23 ⁇ 1) to give 2- ⁇ 2- A light yellow solid of lolo-5- (trifluoromethylinole) pheninole ⁇ amino-6-trifluoromethylizole-3-vinyl-4 (3H) -pyrimidinone was obtained. Yield: 61%; mp: 125 ⁇ 12 ⁇ ⁇ ; 1 !!
  • Example 1 In the same manner as in 18-5, 5-chloro-2--2- ⁇ 2-chloro-3,5-bis (trifluoromethyl) phenyl ⁇ amino-6-trifluoromethyl-3-vinyl-4 (3H)- Pyrimidinone (l.OOg, 2.06 inmol) and chloromethyl (ethyl) ether (0.50 mL, 5.
  • Example 1 As in the case of 61, 4-chloro-2,5-bis (trifluoromethyl) aniline (2.23 g, 8.47 mmol) and 2-methylthio-6-trifluoromethyl-3-vinyl
  • Example 1 As in Example 1-64, 2- ⁇ 4-chloro-2,5-bis (trifluoromethyl) pheninole) amino-6-trifluoromethyl-3-vinyl-4 (3H) -pyri
  • the reaction of midinone (440 mg, 0.97 ol) and sulfuryl chloride (0.08 mL) was carried out, and the resulting crude product was subjected to silylation gel ram ( ⁇ co-gel C-200, ethyl acetate: hexane 1).
  • Example 1 In the same manner as in 1-64, 2- ⁇ 2,6-dibromo-3,5-bis (trifluoromethyl) phenylinole) amino-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidi The reaction of 2- (2,6-dibromo-3,5-bis (trifluoromethyl) phenyl) amino-5-chloro by reacting nonyl (900 mg, 1.57 mmol) with sulfuryl chloride (0.13 mL) Mouth-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone was obtained as a white solid. Yield: 55%; mp: ⁇ ⁇ ; 1 !!
  • a saturated saline solution (100 mL) and ethyl acetate (70 mL) were added to the solution, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate (70 mL). The organic layers were combined, washed with saturated saline (150 mL), and dried over anhydrous sodium sulfate.
  • Example 16-Bromo-2,5-bis (trifluoromethylinole) aniline (5.00 g, 16.2 mmol) and 2-methylthio-6-trifluoromethyl-3-vinyl And 4-4 (3H) -pyrimidinone (4.25 g, 17.9 mmol), and the resulting crude product was subjected to a silylation gel ram (Merck Kieselgel 60, ethyl acetate: hexane 1: 9).
  • Example 1 As in the case of 61, 2-amino-5-toluene toluene (644 mg, 4.65 mmol 1) and 2-methylthio-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone (L.OOg, 4.23 cafe ol) to give 2- (2-methyl-4-nitrophenyl) amino-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone yellow. A colored solid was obtained. Yield: 57%; mp: lSS Si ⁇ C; 1 !!
  • Example 1 In the same manner as in 164, 2- (2-methyl-4-ditrophenyl) amino-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone (486 mg, 1.43 mmol) and sulfuryl chloride (0. llraL) to give 5-chloro-2- (2-methyl-4-ditrophenyl) amino-6-trifluoromethyl-3-vinyl-4 (3H) -pyri. A yellow solid of midinone was obtained. ! Yield: 52 3 ⁇ 4; mp: WS Si ⁇ C; 1 !!
  • reaction solution was poured into water (180 mL) and extracted with ethyl acetate (150 mL ⁇ 2). The organic layer was washed with saturated saline (200 mL), and dried over anhydrous sodium sulfate. After filtering off the drying agent, the filtrate was concentrated under reduced pressure.
  • Example 1 As in 1 64, 2- (4-methyl-2-nitrophenyl) amino-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone (800 mg, 2.35 mmol) and sulfinole chloride (0.19 mL) to give the yellow color of 5-chloro-2- (4-methyl-2-dinitrophenyl) amino-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone. A solid was obtained. Yield: 34%; mp: ⁇ ⁇ ⁇ ; 1 !!
  • Example 1 185 Similar to 85, 2- ⁇ 2,4-bis (trifluoromethyl) phenyl ⁇ amino-5-chloro-6_trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone (5 OOmg, 1. llmmol) and acetyl iodide (693mgx2, 4.44mmolx2) were reacted with each other, and the resulting crude product was subjected to a silylation gel column ( ⁇ -cogel C-200, ethyl acetate: hexane).
  • Example 1 Similarly to 1885, 2- ⁇ 2,4-bis (trifluoromethyl) phenyl ⁇ amino-5-chloro-6-trifluoromethyl-3-vinyl-4 (3H) -pyri
  • the reaction between midinone (720 mg, 1.59 mmol) and 2-chloroethyl (chloromethyl) ether (820 + 410 rag, 6.20 + 3.1 mmol) was carried out, and the resulting crude product was subjected to a silica gel column ( ⁇ CO-1).
  • reaction solution was poured into water (70 m and extracted with ethyl acetate (70 mL ⁇ 2). The organic layer was washed with saturated saline (100 mL), and dried over anhydrous sodium sulfate.
  • Example 1 In a manner similar to 1 85, 2- ⁇ 2,4-bis (trifluoromethyl) phenyl ⁇ amino-5-bromo-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone ( (0.75 g, 1.51 mmol) and chloromethyl (propyl) ether (0.66 g, 6.05 bandol), and the resulting crude product is subjected to a silylation gel column (Kiesel gel 60, Merck Kiesel gel 60, ethyl acetate: hexane).
  • Example 1 2- ⁇ 2,4-bis (trifluoromethyl) phenyl ⁇ amino-5-chloro-6-trifluoromethyl-3-vinyl-4 (3H) -pyri Midinone (1.00 g, 2.21 ol) and butyl (chloromethyl) ether (1.08 g, 8.86 mmol)
  • Example 1 Similarly to 61, methyl anthranilate (639 mg, 4.65 IMO1) and 2-methylthio-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone (1.00 g, 4.23 mmol) To give 2- ⁇ 2- (methoxycarbonyl) phenyl ⁇ amino-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone as a white solid. Yield: 26%; mp: ⁇ ⁇ ⁇ ; 1 !!
  • Example 16 Similarly to 61, ethyl anthranilate (2.80 g, 16.9 mmol) and 2-methylthio-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone (4.00 g, 16.9 mmol) To give 2- ⁇ 2- (ethoxycarbonyl) phenyl ⁇ amino-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone as a white solid. Yield: 30%; mp: ⁇ ⁇ Ryo; 1 !!
  • Example 16 Similarly to 61, 4-aminobenzonitrile (500 mg, 4.65 mmol) and 2-methylthio-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone (1.
  • Example 1 As in the case of 61, 2-methoxy-4-ditroaniline (1.42 g, 8.47 mmol) and 2-methylthio-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidino (2.00 g, 8.47 mmol) to give 2- (2-methoxy-4--2-trophininole) amino-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone as a yellow solid.
  • Example-As in 164, 2- (2-Methoxy-4-nitrotropinole) amino-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone (1. OOrag, 2.81 mmol ) And sulfuryl chloride (0.23 mL) to give 5-chloro-2- (2-methoxy-4-ditrophenyl) amino-6-trifluoromethyl-3-vinyl-4 (3H) -A pale yellow solid of pyrimidinone was obtained. Yield: 74%; melting point: ; 1 !! - NMR (C DC1 3, TMS, ppm): 04.04 (s, 3H), 5.86 (d, J 15.9Hz, 1H), 6.05 (.
  • Example 1 As in the case of 61, 3-amino-4-nitroacetanilide (1.09 g, 8.44 mmol) and 2-methylthio-6-trifluoromethyl-3-vinyl-4 (3H)- By reacting with pyrimidinone (2.00 g, 8.47 mmol) and recrystallizing the obtained crude product from a mixed solution of ethanol and acetone, 4-nitro-3- (6-trifluoromethyl-3-vinyl) was obtained. Yellow crystals of -4 (3H) -pyrimidinone-2-yl ⁇ aminoacetanilide were obtained. Yield: 22!

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Abstract

L'invention concerne des dérivés de 2-anilino-4(3H)-pyrimidone représentés par la formule générale suivante (1). Ces dérivés permettent de repousser, d'exterminer ou de contrôler des pesticides comme des arthropodes (insectes et acariens), nématodes, helminthes et protozoaires qui endommagent les cultures et le bétail dans les cultures en croissance et récoltées. Ces dérivés présentent une grande utilité dans l'agriculture et l'élevage des animaux, les bois, les plantes d'ornement et permettent de traiter des maladies et des mauvaises herbes nuisibles pour l'agriculture et l'horticulture.
PCT/JP1999/006207 1998-11-12 1999-11-08 Derives de 2- anilino (3h)- pyrimidone, intermediaires dans la production de ces derniers, procede de production de ces derniers et pesticides contenant ces derniers comme ingredient actif WO2000029387A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2000582374A JP4600620B2 (ja) 1998-11-12 1999-11-08 ２−アニリノ−４（３ｈ）−ピリミジノン誘導体及び製造中間体、それらの製造方法、並びにそれらを有効成分とする有害生物防除剤
AU10790/00A AU1079000A (en) 1998-11-12 1999-11-08 2-anilino-4(3h)-pyrimidinone derivatives, intermediates in the production thereof, process for producing the same and pesticides containing the same as the active ingredient

Applications Claiming Priority (4)

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JP2001131156A (ja) * 1999-11-08 2001-05-15 Sagami Chem Res Center ２−置換アミノピリミジノン誘導体、それらの製造方法並びにそれらを有効成分とする殺虫、殺ダニ剤
JP2002338551A (ja) * 2001-05-22 2002-11-27 Sagami Chem Res Center ２−アニリノ−４（３ｈ）−ピリミジノン誘導体及び製造中間体、それらの製造方法、並びにそれらを有効成分とする有害生物防除剤
JP2004143172A (ja) * 2002-10-21 2004-05-20 Wyeth 恒温動物における外部寄生虫を調節するためのニューロンナトリウムチャネルアンタゴニストの使用
CN102718665A (zh) * 2003-08-29 2012-10-10 三井化学株式会社 农园艺用杀虫剂的制备中间体
WO2016031987A1 (fr) * 2014-08-29 2016-03-03 国立大学法人東京大学 Dérivé de pyrimidone ayant une activité inhibitrice de l'autotaxine
WO2016052247A1 (fr) * 2014-10-03 2016-04-07 住友化学株式会社 Composé pyrimidinone
WO2017090654A1 (fr) * 2015-11-26 2017-06-01 住友化学株式会社 Composition antiparasitaire et son utilisation
US10183949B2 (en) 2014-08-29 2019-01-22 The University Of Tokyo Pyrimidinone derivative having autotaxin-inhibitory activity
CN110183386A (zh) * 2016-06-02 2019-08-30 华中师范大学 地克珠利衍生物及其应用和含有该衍生物的杀菌剂

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EP0636615A1 (fr) * 1992-04-15 1995-02-01 Nissan Chemical Industries, Limited Derive de 2-arylaminopyrimidinone, et herbicide et regulateur de la croissance vegetale contenant ce compose
JPH072799A (ja) * 1993-06-18 1995-01-06 Nissan Chem Ind Ltd ２−アリールイミノピリミジノン誘導体および除草剤、植物生長調節剤
WO1998051675A1 (fr) * 1997-05-15 1998-11-19 Sagami Chemical Research Center Derives de l'anilinopyrimidinone, leur procede de production, et insecticides/acaricides dont ils constituent le principe actif
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Cited By (19)

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JP4674676B2 (ja) * 1999-11-08 2011-04-20 公益財団法人相模中央化学研究所 ２−置換アミノピリミジノン誘導体、それらの製造方法並びにそれらを有効成分とする殺虫、殺ダニ剤
JP2001131156A (ja) * 1999-11-08 2001-05-15 Sagami Chem Res Center ２−置換アミノピリミジノン誘導体、それらの製造方法並びにそれらを有効成分とする殺虫、殺ダニ剤
JP2002338551A (ja) * 2001-05-22 2002-11-27 Sagami Chem Res Center ２−アニリノ−４（３ｈ）−ピリミジノン誘導体及び製造中間体、それらの製造方法、並びにそれらを有効成分とする有害生物防除剤
JP2004143172A (ja) * 2002-10-21 2004-05-20 Wyeth 恒温動物における外部寄生虫を調節するためのニューロンナトリウムチャネルアンタゴニストの使用
CN102718665A (zh) * 2003-08-29 2012-10-10 三井化学株式会社 农园艺用杀虫剂的制备中间体
US9089133B2 (en) 2003-08-29 2015-07-28 Mitsui Chemicals, Inc. Insecticide for agricultural or horticultural use and method of use thereof
US9101135B2 (en) 2003-08-29 2015-08-11 Mitsui Chemicals, Inc. Agricultural/horticultural insecticide and method for using the same
EP3187492A4 (fr) * 2014-08-29 2018-05-09 The University of Tokyo Dérivé de pyrimidone ayant une activité inhibitrice de l'autotaxine
WO2016031987A1 (fr) * 2014-08-29 2016-03-03 国立大学法人東京大学 Dérivé de pyrimidone ayant une activité inhibitrice de l'autotaxine
US10183949B2 (en) 2014-08-29 2019-01-22 The University Of Tokyo Pyrimidinone derivative having autotaxin-inhibitory activity
JPWO2016031987A1 (ja) * 2014-08-29 2017-07-13 国立大学法人 東京大学 オートタキシン阻害活性を有するピリミジノン誘導体
WO2016052247A1 (fr) * 2014-10-03 2016-04-07 住友化学株式会社 Composé pyrimidinone
CN107074781A (zh) * 2014-10-03 2017-08-18 住友化学株式会社 嘧啶酮化合物
US9802930B1 (en) 2014-10-03 2017-10-31 Sumitomo Chemical Company, Limited Pyrimidinone compound
JPWO2016052247A1 (ja) * 2014-10-03 2017-07-13 住友化学株式会社 ピリミジノン化合物
CN107074781B (zh) * 2014-10-03 2020-01-17 住友化学株式会社 嘧啶酮化合物
WO2017090654A1 (fr) * 2015-11-26 2017-06-01 住友化学株式会社 Composition antiparasitaire et son utilisation
CN110183386A (zh) * 2016-06-02 2019-08-30 华中师范大学 地克珠利衍生物及其应用和含有该衍生物的杀菌剂
CN110183386B (zh) * 2016-06-02 2022-07-29 华中师范大学 地克珠利衍生物及其应用和含有该衍生物的杀菌剂

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