WO2007083411A1

WO2007083411A1 - Pest controlling composition containing diamine derivative

Info

Publication number: WO2007083411A1
Application number: PCT/JP2006/317935
Authority: WO
Inventors: Naofumi Tomura; Natsuko Araki; Hiroshi Ishimoto
Original assignee: Mitsui Chemicals, Inc.
Priority date: 2006-01-19
Filing date: 2006-09-05
Publication date: 2007-07-26
Also published as: WO2007083394A1

Abstract

A pest controlling composition characterized by containing, as the active ingredients, a diamine derivative which is represented by the general formula (1) [wherein R1 represents C1-6 alkyl, etc.; R2 and R5 independently represent each hydrogen, C1-6 alkyl, etc.; R3 and R4 independently represent each hydrogen, C1-6 alkyl, etc., or R3 and R4 are bonded together to form a C3-6 hydrocarbon ring; R6, R7, R8 and R9 independently represent each hydrogen, C1-6 alkyl, etc.; R10 represents hydrogen, C1-6 alkyl, etc.; A represents oxygen, etc.; and Q1 represents aryl or a heterocycle] together with one or more compounds selected from the group consisting of another bactericide, an insecticide and a miticide.

Description

'Makusho' Pest control composition containing diamine derivatives Technical Field

The present invention relates to a pest control composition comprising a diamine derivative. Background art

Disease control plays a major role in crop cultivation, and various fungicides have been developed and used. However, there is not always enough bactericidal activity or harm to useful crops. In recent years, the use of agricultural and horticultural fungicides has led to the emergence of resistant bacteria to drugs, and existing drugs may not exhibit sufficient activity. Furthermore, there is a need for new fungicides that are safe and can control harmful bacteria at low concentrations due to environmental problems. It has been disclosed in W 0 3 0 0 8 3 7 2 that diamine derivatives are useful as pest control agents so far. However, while WO 0 3 0 0 8 3 7 2 shows control activity only for rice blast, the diamine derivative of the compound of the present invention has a broad spectrum of disease control spectrum, and the structure is also disclosed in the publication. It is different from the compounds described in the description. ·

In addition, the second active ingredient in the present invention, the fungicide, insecticide, and acaricide, are each a pesticide manaure (The P e s t i c i c e d e Manu a l

It is a publicly known compound described in T hirte ent hE d i t i o n). However, these active compounds each have pests that cannot or cannot be controlled by themselves.

Patent Document 1: WO 0 0 3 0 0 8 3 7 2,

Non-Patent Document 1: Pesticide Manual (The P e s t i c i d e M a n u a 1 T h i r t e e nt e E d i t i o n 2 2 years) Disclosure of Invention

In the present invention, the compound represented by the general formula (1), and the fungicide, the insecticide or the acaricide each have pests that cannot or cannot be controlled by themselves. Accordingly, an object of the present invention is to provide a pest control composition for efficiently controlling pests. As a result of repeated studies to solve these problems, the present inventors have determined that one or more compounds represented by the general formula (1) and one or more compounds from the group consisting of a fungicide, an insecticide or an acaricide. The present inventors have found that pests can be efficiently controlled by mixing, and have completed the present invention.

That is, the present invention is as follows.

[1] General formula (1):

(Chemical 1)

[Wherein R 1 is an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or 2 to 6 carbon atoms. An alkynyl group, an aryl group, a heterocyclic ring, an aryl alkyl group having 1 to 6 carbon atoms in an alkyl group, or a heterocyclic alkyl group having 1 to 6 carbon atoms in an alkyl group,

R 2 and R 5 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or a cycloalkenyl group having 3 to 6 carbon atoms. An alkynyl group having 2 to 6 carbon atoms, an acyl group, an aryl group, a heterocyclic ring, an aryl group having 1 to 6 carbon atoms in the alkyl group, or a heterocyclic alkyl group having 1 to 6 carbon atoms in the alkyl group. Represents

R 3 and R 4 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or a cycloalkenyl group having 3 to 6 carbon atoms. , An alkynyl group having 2 to 6 carbon atoms, an aryl group, a heterocyclic ring, an aryl alkyl group having 1 to 6 carbon atoms in the alkyl group, or a heterocyclic alkyl group having 1 to 6 carbon atoms in the alkyl group. Or R 3 and R 4 may be bonded to each other to form a hydrocarbon ring having 3 to 6 carbon atoms,

R 6, R 7, R 8 and R 9 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or the number of carbon atoms. A cycloalkenyl group having 3 to 6 carbon atoms and an alkynyl group having 2 to 6 carbon atoms, provided that at least one substituent of R 6, R 7, R 8 and R 9 is an alkyl group having 1 to 6 carbon atoms, carbon A cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, and an alkynyl group having 2 to 6 carbon atoms- RIO is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. Group represents an acyl group, A represents an oxygen atom or a sulfur atom, and O represents an aryl group or a heterocycle. And a pesticide composition characterized by comprising as an active ingredient one or more compounds selected from the group consisting of other fungicides, insecticides, and acaricides. .

[2] Bactericides, insecticides, acaricides are triazimephone, hexaconazole, puccinazole, ipconazole, prochloraz, triflumizole, tebuconazol, epoxiconazole, diphenoconazole, funolesilazole, triazimenole, Ciproconazole, Metoconazonole, Funorequinconazonore, Vitalenolanol, Tetraconazonore, Triticonazol, Funoretrifofonore, Pencona Zonole, Giniconazonole, Fenbuconazonore, Microcone Ninore, Himexazonole, Imazalinole, Frametopil, Tifluzamide, Etridazole, Oxispoconazole, Oxyspoconazole fumarate, Azole fungicides such as furazoate, prothioconazole, pyrimidine fungicides such as pyriphenox, fenarimol, nuarimol, buprimate, a-linopyrimidine fungicides such as mepa-pyrim, cyprogel, pyrimethanil, diflumetrim Agents, Metalaxyl, Metalaxirux M, Oxazixil, Benaxylil and other asylalanine fungicides, thiophanate methyl, benominole, benzimidazole, carbendazir, thiabendazole and other benzimidazole fungicides, manzeb, provineb, dineb, methylum, Organic sulfur-based fungicides such as ambam, polycarbamate, thiadiazine, etc., organic chlorine-based fungicides such as tetraphthalic isophthalonitrile, ethaboxam, oxycanoloxy Carboxam fungicides such as carbene, carboxin, funoletranyl, sylthiophane, meproninole, boscalid, dimethomorph, fenprovidin, phenpropimorph, spiroxamine, morpholine fungicides such as tridemonolev, dodemorph, fulmol, methyl methoximus Tominos trobin, Olisas trobin, Funolexus trobin, Trifloxys trobin, Dimoxis trobin, Pyramlos trobin, Pixoxys trobin, etc. Dazomet, Methyli Sothiocynate, Cronolevicrin, Metasulfocarp, Hydroxyisoxazo Monore, Hydroxy Soxazo Monorecalium, Ecomezo Monore, D-D, Carbam, Methyl Iodide, Basic Copper Chloride, Basic copper sulfate, copper nonylphenol sulfonate, copper oxine, DBEDC, anhydrous copper sulfate, copper sulfate pentahydrate, cupric hydroxide and other copper-based fungicides, inorganic sulfur, hydrated sulfur agent, lime sulfur mixture, Inorganic fungicides such as zinc sulfate, phenthine, sodium hydrogen carbonate, potassium hydrogen carbonate, hypochlorite, metallic silver, etc.Organic phosphorus such as edifenphos, tonolecrofosmethyl, fosetyl, iprobenphos, dinocap, pyrazophos Fungicides, carpropamide, fusalide, tricyclazole, pyrokilone, diclocimet, fucolide Melanin biosynthesis inhibitor fungicides such as noxanil, kasugamycin, validamycin, polyoxin derivatives, blasticidin s, tech mouth phthalam, oxyte tracycline, mildomycin, streptomycin and other antibiotic fungicides, rapeseed oil , Natural oils such as machine oils, carbamate fungicides such as Bench Avari Carbuisopropyl, Yproval Calp, Propamo Calp, Dietofen Calp, pyrrole fungicides such as Fluoride, Fludioxonyl, Fenpicloel, Probenazole, A Brantactivators that induce plant disease resistance such as cibenzoral S-methyl and thiazinyl, quinolinic fungicides such as quinoxyphene and oxolucic acid, cyflufenamide, phenhexamide, and metrafue Non, Picobenzamide, Proquinazide, Famoxadone, Shiazophamide, Fuenamidon, Zoxamide, Chlorotamine Ninore, Shimoxaninole, Quabutane, Dithianon, Funoreazinam, Phonolepet, Diclofluanide, Triphorine, Isoprothione , Pencyclon, Quinomethionate, Imoctadine Acetate, Imoctadine Arbesylate, Guazatine, Chloroneb, Organonickel, Dodine, Kintozene, Trirylfunolide, Vanilladine, Nitrotalisopropyl, Fenitropan, Dichlorane, DPC, Dimethymol, Benjazonole, Full Metal Bar, Mandy Propamide, (RS) —N— [2— (1, 3-Dimethylbutyl) thiophene 3-yl] 1 1 —Metinore 3—Trifonoleolomethinole 1 H—Virazo One-Lou 4-Carboxamide (This compound is described in Japanese Patent No. 3 1 6 4 7 6 2; Yes. The general name of the pending application is pentiovir. ), General formula (2):

(Chemical 2)

(This compound is described in WO 0 1 1 08 25, and its bactericidal activity and production method are described.) General formula (3):

(Chemical 3) (3)

(This compound is described in U S 6 6 20 8 1 2 and describes its bactericidal activity and production method.) General formula (4):

(Chemical 4)

(This compound is described in WO 0 3 0 79 78 8 and describes the bactericidal activity and production method.) General formula (5):

(Chemical 5)

[Wherein R 11 represents an alkyl group having 1 to 6 carbon atoms, an alkyl group having 2 to 6 carbon atoms, an aryl alkyl group or a heterocyclic alkyl group, and R 12 and R 17 are Each represents a hydrogen atom, R 1 3 and R 14 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, R 15 and R 16 each represent a hydrogen atom, and R 1 8 represents an aryl group or a hetero ring. ] A compound represented by (This compound is W 02 00 3008 3 7 2, which describes the bactericidal activity and production method. ), Or general formula (6):

(Chemical 6)

[Wherein R 19 is an alkyl group having 1 to 6 carbon atoms substituted with halogen, an alkyl group having 3 to 6 carbon atoms substituted with halogen, or an alkyl group having 2 to 6 carbon atoms substituted with halogen. -R group, R 20 and R 25 each represent a hydrogen atom, R 2 1 and R 22 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, R 2 3 and R 24 Each represents a hydrogen atom, and R 26 represents an aryl group or a hetero ring. (This compound is described in WO 20050424 74, and its bactericidal activity and production method are described.);

Areslin, Tetramethrin, Resmethrin, Phenotrin, Frametrin, Penoremetrine, Cypermethrin, Deltamethrin, Cyhalothrin, Schiffrinrin, Fuenproprin Trinity, Tralometrine, Shikuguchi Protoline, Funolecitrinate, Full Variate, Acrinatrin, Tefnoretrin, Bifentrin, Empertoline, Beta Saino Resin, Fen / Kurereto, Esfen / Kureate, Funolev, Rositoline, Methonoleslin, Profnoreslin, Dimefnoreslin, Shiranoureofen, Insect Chrysanthemum Extract, Etofenprox, No, Norefenprox, etc. Pyrethroid insecticides, DDVP, sianophos, fenthion, phenylothio , Tetrachlorbinphos, Dimethylvinphos, Propafos, Methylparathion, Temefos, Hoxime, Acephete, Isophenfos, Salicion, DE P, EPN, Ethion, Mecarbam, Pyridafenthion, Diazinon, Pirimiphosmethyl, Etrifos, Isoxathion , Quinalfos, Chlorpyrifosmethyl, Chlorpyrifos, Josaron, Phosmet, Methidathion, Oxidebrophos, Bamidothion, Malathion, Fentoate, Dimethoate, Formothion, Thiometone, Ethylthiomethone, Phosphos, Prophos , Monochrome Tofos, Naredo, Phosthiazeto, Triclonolehon, Etoprofos, Kazusafos, Black Refenbinhosu, Diclofenthion, Ethylthiomethone, Metamidhos, Dichlorvos, Tebupirimfos, Ometoate, Triazofos, Oxidemethone monomethyl, Azinphos-Methinore, Clonoletoxifos, Diclotofos, Disunolefotone, Defenaphos, Methylphosphine Organophosphorus insecticides such as mevinphos, parathion, NAC, MTMC, MIPC, BPMC, XMC, PHC, MPMC, etiofencalp, bendiocarp, pirimicarb, carbosulfan, benfracarp, mesomil, oxamil, aldicarp, thiozi Calp, aranicanoleb, carbofuran, metiocarp, phenothiocalp, formetate, xylylmethylcarbamate, propoxal, isoprocarp, etc. Bamet insecticides, imidacloprid, nitenbiram, acetamiprid, dinotefuran, thiamethoxam, thiacloprid, neonicotinoid insecticides such as clothianidin, bromopropyrate, dichophor, endosulfan, Lindan, etc. Organochlorine pesticides, difluvenslon, chlorfluzuron, tefruvenslon, trifunolemuron, funolefuenoxuron, funolecycloxuron, hexafnorem mouth, funolezuron, difenthiuron, nono Insect growth control agents such as kunoreron, nobifremolem, bistriflugone, kuma mafuenozide, norofenozide, methoxifenozide, norephurelon, cyromazine, triazamate, nicotine sulfate, polynactin complex, abamectin, mi Bemectin, Repimectin, BT (Baci lus thuringiens is), Spinosad, Rotenone and other natural insecticides, Cartap, Tiocyclam, Benzenoletap, Pimetrozin, Fiproninole, Buprofezin, Phenoxycarp, Pyriproxyfen, Me Toprene, Hydroprene, Quinoprene, Endos / Lefan, Triazuron, Tebufenozide, Benzephine, Emamectin, Emamectin benzoate, Flupirazophos, Flucribilim, Flufendin, Indoxacalp, Tolenfenvirado, Gamma Cyhalothrin, Eth Prolol, Acetoprole, Amidofnoremet, Chronofenenavire, Flonicamid, Furfuranerim, Pyridalyl, Natrium oleate, Potassium oleate, Faza Dilactin, carbam, carbam sodium, propargite, azocyclothine, benzoximate, metaaldehyde, protrifen boot, penk mouth thiaz, flubenamide, metaflumizole, general formula (7):

[Wherein R 27 represents a methyl group or a chloro group, R 28 represents a methyl group, a chloro group, a bromo group or a cyano group, and R 29 represents a chloro group, a bromo group, a trifluoromethyl group or a cyanomethoxy group. R 30 represents a methyl group or an isopropyl group. (This compound is described in WO 2003 3 1 55 19 and describes the insecticidal activity and production method.) General formula (8):

(Chemical 8)

[Wherein R 3 1 represents 1, 1, 1, 2, 3, 3, 3-heptafluoro-2-propyl group or 1, 1, 2, 2, 3, 3, 3_heptafluoro-1-propyl group. The (This compound is described in Japanese Patent Application Laid-Open No. 2001-342 1 86, and describes the insecticidal activity and production method.) General formula (9):

[Wherein, X i is a hydrogen atom or a fluorine atom, R 3 2 and R 3 3 are a hydrogen atom and an alkyl group having 1 to 4 carbon atoms, respectively, and Q ₂ is a phenyl group or a halogen atom. An alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, a haloalkenyl group having 2 to 4 carbon atoms, an alkenoquinole group having 2 to 4 carbon atoms, a carbon number 2-4 haloanolequinyl group, cycloalkyl group having 3-6 carbon atoms, halocycloalkyl group having 3-6 carbon atoms, alkoxy group having 1-3 carbon atoms, haloalkoxy group having 1-3 carbon atoms, carbon number 1 ~ 3 alkylthio group, 1 ~ 3 carbon halo anoalkylthio group, 1 ~ 3 alkylsulfinyl group, carbon number :! ~ 3 haloalkylsulfier groups, carbon number; ~ 3 alkylsulfonyl group, 1 ~ 3 carbon haloalkylsulfonyl group, 1 ~ 4 carbon alkylamino group, 1 ~ 4 carbon dialkylamino group, cyano group, nitro group, hydroxy group, carbon number 1 to 4 alkylcarbonyl groups, carbon number :! A substituted phenyl group having one or more substituents which may be the same or different, selected from an alkylcarbonyloxy group having 4 to 4, an aralkoxycarbonyl group having 1 to 4 carbon atoms, a acetylamino group, and a phenyl group; Or a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, a haloalkenyl group having 2 to 4 carbon atoms, or 2 to 4 carbon atoms. Alkynyl group, haloalkynyl group having 2 to 4 carbon atoms, cycloalkyl group having 3 to 6 carbon atoms, halocycloalkyl group having 3 to 6 carbon atoms, alkoxy group having 1 to 3 carbon atoms, carbon number :! ~ 3 haloalkoxy group, 1 ~ 3 alkylthio group, 1 ~ 3 haloalkylthio group, 1 ~ 3 alkylsulfinyl group, carbon number :! ~ 3 haloalkyl sulrefinyl group, 1 ~ 3 alkyl sulfonyl group, carbon number :! -3 haloalkylsulfonyl groups, C1-C4 alkynoleamino groups, C1-C4 dialkylamino groups, Cyano groups, nitro groups, hydroxy groups, C1-C4 alkylcarbonyl groups, carbon A pyridyl group having one or more substituents which may be the same or different and selected from an alkylcarbonyloxy group having 1 to 4 carbon atoms, an alkoxycarbonyl group having 1 to 4 carbon atoms, an acetylamino group, and a phenyl group; ₃ is the general formula (A)

(In the formula, Y ₅ may be the same or different, and are a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or 1 to 4 carbon atoms. Haloalkoxy group, carbon number 1-3 alkylthio group, carbon number:! -3 haloalkinorethio group, carbon number 1-3 alkylsulfier group, carbon number:! -3 haloalkylsulfinyl group, carbon 1 to 3 ananolylsulfonyl group, 1 to 3 haloalkylsulfonyl group, cyano group, Υ ₃ is a 2 to 6 perfluoroalkyl group, 1 to 6 carbon perfluoro Oroarukiruchio group, Pas one full O b alkylsulfinyl groups of from 1 to 6 carbon showed Roh Funoreo port alkylsulfonyl Interview Le group of from 1 to 6 carbon, Upsilon _2, Upsilon ₄ is a hydrogen atom, a halogen atom, a carbon Represents an alkyl group of 1 to 4 ) Represented by. (This compound is described in WO 2 005-73 1 65, and describes the insecticidal activity and the production method), or the general formula (10):

(Chemical 1 1)

Wherein, chi ₂ is a hydrogen atom or a fluorine atom, R35, R36 are each a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, R34 is Kill group having 1 to 6 carbon atoms, carbon atoms A haloalkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a haloanolekenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a haloalkynyl group having 2 to 6 carbon atoms, and a 3 to 8 carbon atoms A cycloalkyl group, a halocycloalkyl group having 3 to 8 carbon atoms, —Ε — Zi— R3 7 (wherein is an alkylene group having 1 to 4 carbon atoms, carbon number A alkenylene group having 2 to 4 carbon atoms, an alkynylene group having 3 to 4 carbon atoms, a haloalkylene group having 1 to 4 carbon atoms, a haloalkenylene group having 2 to 4 carbon atoms, and a haloalkylene group having 3 to 4 carbon atoms. R 3 7 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, or 2 to 6 carbon atoms A haloalkenyl group having 2 to 6 carbon atoms, Zi is —O—, —S—, one SO—, one S0 ₂ —, one C (= 0) —, —C (= 0) 0—, -0C (= 0) one, — N (R 3 8) one, — C (= 0) N (R 3 8) —, — N (R 3 8) C (= 0)-(R 3 8 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkyl carbonyl group having 1 to 4 carbon atoms, a haloalkylcarbonyl group having 1 to 4 carbon atoms, or an alkoxycarbonyl group having 1 to 4 carbon atoms.) Indicates. ), -E ₂ -R 3 9 (wherein E ₂ is an alkylene group having 1 to 4 carbon atoms, an alkenylene group having 2 to 4 carbon atoms, an alkynylene group having 3 to 4 carbon atoms, or 1 to carbon atoms) 4 haloalkylene group, haloalkylene group having 2 to 4 carbon atoms, haloalkylene group having 3 to 4 carbon atoms, R 3 9 is a cycloalkyl group having 3 to 8 carbon atoms, and 3 to 8 carbon atoms A halocycloalkyl group, a cyano group, a nitro group, a hydroxy group, a phenyl group, or the same or different, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, Carbon number:! ~ 6 alkoxy group, C 1-6 haloalkoxy group, C 1-6 alkylthio group, C 1-6 haloalkylthio group, C 1-6 alkylsulfinyl group, Carbon number: ~ ~ 6 haloalkylsulfinyl group, carbon number :! 6 alkylsulfonyl groups, carbon number:! ~ 6 halo aralkylsulfonyl group, cyano group, nitro group, hydroxyl group, alkyl carbonyl group having 1 to 4 carbon atoms, haloalkyl carbonyl group having 1 to 4 carbon atoms A substituted phenyl group having one or more substituents selected from an alkylcarbonyloxy group having 1 to 4 carbon atoms, an alkoxycarbonyl group having 1 to 4 carbon atoms, a pyridyl group, Q ₄ represents a haloalkyl group having 1 to 6 carbon atoms, a substituted pyridyl group having one or more substituents selected from a haloalkoxy group having 1 to 6 carbon atoms, a phenyl group, and a tetrahydrofuran group. General formula (B):

(In the formula, 、 ₆ , and may be the same or different, halogen atom, carbon number 1

~ 4 alkyl groups, carbon number :! ~ 4 haloalkyl groups, carbon number :! ~ 4 anoalkoxy group, 1 ~ 4 carbon haloalkoxy group, 1 ~ 3 carbon alkylthio group, carbon number

1 to 3 haloalkylthio groups, 1 to 3 carbon alkylsulfifer groups, 1 to 3 haloalkinolesnorefiel groups, 1 to 3 alkynolesulfonyl groups, 1 to 3 haloalkyl groups sulfo - group, indicates Shiano group, Upsilon ₈ par full O b alkyl group having 2 to 6 carbon atoms, 1 to the number of carbon atoms of 6 Pas - full O b alkylthio group, the number of carbon atoms:! ~ 6 perfluoroanoleylsulfinyl group, carbon number :! It indicates Pafuruoro alkyl sulfonyl Le group ~ 6, Υ _7, Υ ₉ is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms. ) ] A compound represented by the formula (This compound is WO 2 0

0 5-2 1 4 8 8 and describes the insecticidal activity and production method. ) Chlorbendilate, Phenisobromolate, Tetradiphone, CPCBS (Chlorfenson), BPPS, Quinomethionate, Amitraz, Benzomate, Hexithiazox, Fenbutazin oxide, Sihexatin, Dienochlor, Clofentezine, Pyridamate, Fenpyrazate Pest control as described in paragraph [1], which is one or more compounds selected from tebufenpyrad, pyrimidifene, acequinosyl, bifenazate, etoxazole, spirodiclofen, spinomesifen, amidflumet and difluvidazine Composition.

The mixed composition of the present invention exerts a remarkable control effect on a plurality of pests exhibiting a pest and a drug resistance, etc., each of which was not able to obtain a sufficient control effect with each single agent, It also has a remarkable control effect against pests that could not be controlled and multiple pests that show drug resistance. Therefore, the pest control composition of the present invention can greatly contribute to labor saving in agriculture. BEST MODE FOR CARRYING OUT THE INVENTION

The present invention is described in detail below.

Further, the pest control composition of the present invention is a diamine represented by the following general formula (1). It is characterized by containing as an active ingredient a derivative and one or more compounds selected from the group consisting of other fungicides, insecticides, and acaricides.

(Chemical 1 3)

[Wherein R 1 is an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or 2 to 6 carbon atoms. An alkynyl group, an aryl group, a heterocycle, an arylalkyl group having 1 to 6 carbon atoms in the alkyl group, or a heterocyclic alkyl group having 1 to 6 carbon atoms in the alkyl group,

R 2 and R 5 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or a cycloalkenyl group having 3 to 6 carbon atoms. An alkynyl group having 2 to 6 carbon atoms, an acyl group, an aryl group, a hetero ring, an aryl group having an alkyl group having 1 to 6 carbon atoms, or a hetero ring having an alkyl group having 1 to 6 carbon atoms. Represents an alkyl group,

R 3 and R 4 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or a cycloalkenyl group having 3 to 6 carbon atoms. Group, an alkynyl group having 2 to 6 carbon atoms, an aryl group, a heterocyclic ring, an arylalkyl group having 1 to 6 carbon atoms in an alkyl group, or a heterocyclic alkyl group having 1 to 6 carbon atoms in the alkyl group R 3 and R 4 may be bonded to each other to form a hydrocarbon ring having 3 to 6 carbon atoms,

R 6, R 7, R 8 and R 9 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or 3 carbon atoms. A cycloalkenyl group having 6 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, provided that at least one substituent of R 6, R 7, R 8 and R 9 is an alkyl group having 1 to 6 carbon atoms, carbon A cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, and an alkynyl group having 2 to 6 carbon atoms,

R 10 is a hydrogen atom, an alkylenealkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or 2 to 6 carbon atoms. Represents an alkynyl group or a acyl group, and A represents an oxygen atom or a sulfur atom. And

Qi represents an aryl group or a hetero ring. ]

In the diamine derivative represented by the general formula (1), each substituent is not limited to the following, but typical examples thereof are as follows.

In the diamine derivative represented by the general formula (1) and the method for producing the same, although not limited to the following, examples of typical substituents include the following. Examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group, and these may be substituted with a substituent, and have 3 to 6 carbon atoms. Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like. These may be substituted by a substituent, and examples of the alkenyl group having 2 to 6 carbon atoms include A vinyl group, a propenyl group, a butyr group, a pentenyl group, a hexenyl group, etc., which may be substituted by a substituent, and as a cycloalkenyl group having 3 to 6 carbon atoms, cyclopropenyl Examples include a ninore group, a cyclobutenino group, a cyclopentenino group, a cyclohexenyl group, etc., and these may be substituted with a substituent, Examples of the alkynyl group having 2 to 6 primes include ethynyl group, propier group, butur group, pentur group, hexyl group and the like, and these may be substituted with a substituent, and as the aryl group, phenyl Group, naphthyl group, etc., and these may be substituted with a substituent, and the heterocycle has at least one carbon atom containing at least one of nitrogen atom, oxygen atom and sulfur atom 1 to 15 For example, furan, thiophene, oxazole, pyrrole, 1 H-pyrazole, 3 H-pyrazole, imidazole, thiazole, oxazole, isoxazole, isothiazole, [1,2,3] oxadiazole, [1, 2, 4] oxaziazole, [1, 3, 4] oxaziazole, furazane, [1, 2, 3] thiadiazole, [1, 2, 4] Thiadiazonole, [1, 2, 5] Thiadiazole, [1, 3, 4] Thiadiazol, 1 H— [1, 2, 3] Triazole, 2H— [1, 2, 3] Triazole, 1 H— [1, 2, 4] Triazole, 2H— [1, 2, 4] Triazole, 1 H-tetrazole, 5 H-tetrazole, 2, 3-dihydro 1 H-pyrrole, 2, 5-dihydro 1 H— Pyrrole, 3,4-dihydro-1,2H-pyrrole, pyrrolidine, 2,3-dihydrofuran, 2,5-dihydrofuran, tetrahydrofuran, 2,3-dihydrodrofen, 2,5-dihydrodrofen, tetrahydrodrothophen, virazolidine , Pyridine, pyran, thiopyran, Pyridazine, Pyrimidine, Pyrazine, [1, 2, 3] Triazine, [1, 2, 4] Triazine, [1, 3, 5] Triazine, 2H— [1, 2, 3]

2 H- [1, 2, 4] oxazidin, 2 H— [1, 2, 5] oxazini Γ gin,

2 H— [1, 2, 6] oxazidine, 4 H— [1, 2, 3] oxazi: gin,

4 H— [1,2,4] oxazidine, 4H— [1,2,5] oxazid: azine,

4 H— [1, 2, 6] oxazidin, 4 H— [1, 3, 4] oxazidin

4 H— [1,3,5] oxazidine, 2 H— [1,2,3] Chia,

H-[1, 2, 4] The -Asian Gin, 2 H— [1, 2, 5] Thiadiazine, 2 H-

[1, 2, 6] thiazazine, 4 H— [1, 2, 3]-I. Azine, 4 H--[1, 2, 4] thiadiazine, 4 H— [1, 2, 5] thiadiazine, 4 H— [1,2,6] thiadiazine, 4H_ [1,3,4] thiadiazine, 4H— [1,3,5] thiadiazine, 2,3-dihydropyridine, 3,4-dihydropyridine, 1, 3 1-dioxane, 1,4_dioxane, piperidine, 3, 4-dihydrodraw 2 H-pyran, 3,6-dihidraw 2 H-pyran, tetrahydropyran, 3, 4-dihydrone 1 2 H —Chiopyran, 3, 6—Dihi Draw 2 H—Chipiran, Tetrahydrochopyran, Morpholine, Piperazine, Chroman, Chromene, Isobenzofuran, Indolizine, Indole, 3 H—Indole, Dihydroindole, I Soindole, 1 H-indazole, 2 H-indazole, purine, kino , Isoquinoline, 4 H-quinolidine, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, carpazole, acridine, phenazine, phenanthorin, phenothiazine, phenoxazine, indoline, isoindoline, benzofuran, dibenzotropenzofuran , Benzo [c] thiophene, benzo [c] isothiazole, benzo [c] isoxazole, dihydrobenzothiophene, benzoxazonore, benzisoxazomonore, benzimidazole, benzothiazonore, benzoisothiazonole, 1H —Benzotriazolone, 2 H-benzotriazole, benzo [1,4] dioxane, 2,3-dihydrobenzo [1,4] dioxane, benzo [1,3] dioxole, β-carboline , Nzo [1,2,5] oxadiazole, benzo [1,2,5] thiadiazole, pteridine, imidazo [1,2-a] pyridine, imidazo [1,2-a] pyrimidine, pyrazo mouth [1, 5-a] pyrimidine, [1,2,4] triazolo [1,5-a] pyrimidine and the like, which may be substituted by a substituent, and as an acyl group, an acetyl group, etc. Of arylcarbonyl such as alkylcarbonyl group or benzoyl group Bonyl group etc. are mentioned, These may be substituted by the substituent. Examples of the substituent for the alkyl group having 1 to 6 carbon atoms include an alkyl group such as a methyl group, an ethyl group, a propyl group, or a butyl group, and a cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group. , Halogen-substituted alkyl groups such as trifluoromethyl group, difluoromethyl group, bromodifluoromethyl group or trifluoroethyl group, alkoxy groups such as methoxy group, ethoxy group, propoxy group or butoxy group, trifluoromethoxy group Groups, halogen-substituted alkoxy groups such as difluoromethoxy group or trifluoroethoxy group, alkylthio groups such as methylthio group, ethylthio group, propylthio group or ptylthio group, trifluoromethylthio group, difluoromethylthio group or trifluoroethylthio group Alkyl sulfinyl groups such as halogen-substituted anololethio groups, methane sulfiel groups, ethane sulfiel groups, propane sulfinyl groups or butansno refinyl groups, trifluoromethane sulfinyl groups, difluoro methane sulfinyl groups, or trifluoronorophane ethanesole Halogen-substituted alkylsulfinyl groups such as finyl groups, methanesulfonyl groups, ethanesulfonyl groups, prosulfonylamine groups or butanesulfonyl groups such as alkylsulfonyl groups, trifluoromethanesulfonyl groups, difluoromethanesulfonyl groups, or trifluoroethanesulfonyl Group-substituted guanolequinolsulfonyl group, methanesulfonamide group, ethanesulfonamide group, propanesulfonamide group or butanesulfonamide Alkylsulfone amide groups such as fluoride groups, trifluoromethanesulfonamide groups, difluoromethanesulfonamide groups, trifluoroethanesulfonamide groups, and other halogen-substituted alkylsulfonamide groups, methylamino groups, and ethylamino groups , Alkylamino group such as propylamino group, and arylamino group such as phenylamino group, amide group such as acetylamino group or benzoylamino group, halogen atom of fluorine atom, chlorine atom, bromine atom or iodine atom, acetyl group And an acyl group such as a benzoyl group can be exemplified, and does not include a case where an alkyl group having 1 to 6 carbon atoms is substituted with an aryl group or a heterocyclic ring. C 3-6 alkenyl group, C 2-6 alkenyl group, C 3-6 cycloalkenyl group, C 2-6 alkyl group, aryl group, heterocycle, alkyl group Examples of the substituent for an arylalkyl group having 1 to 6 carbon atoms or a heterocyclic alkyl group having 1 to 6 carbon atoms are alkyl groups such as a methyl group, an ethyl group, a propyl group, or a butyl group. , Cyclopropyl group, cyclobutyl group, cyclopentyl group or cyclohexyl A cycloalkyl group such as a syl group, a halogen-substituted alkyl group such as a trifluoromethyl group, a difluoromethyl group, a bromodifluoromethyl group or a trifluoroethyl group, an alkoxy such as a methoxy group, a ethoxy group, a propoxy group or a butoxy group Groups, halogen-substituted alkoxy groups such as trifluoromethoxy group, difluoromethoxy group or trifluoroethoxy group, alkylthio groups such as methylthio group, ethylthio group, propylthio group or butylthio group, trifluoromethylthio group, difluoromethylthio group or Halogen-substituted alkylthio groups such as rifluorethylthio group, methansnorefinino group, ethanesnorefinyl group, prono. Non-substituted guanolequinol groups such as alkylsulfinyl groups such as nsunorefinyl group or butansnorefinyl group, trifluoromethanes norefiel group, difluoroleomethanesnorefinyl group or trifluoroethanesulfininole group. Finolyl group, methanesulfoninole group, ethanesulfonyl group, propane sulphonylon group, butanesulfonyl group, etc., quinolenosenorephoninole group, trifluoromethanesulfonyl group, difluoromethanesulfonino group or tri Halogen-substituted alkylsulfonyl groups such as fluoroethanesulfonyl group, methanesulfonamide groups, ethanesulfonamide groups, propanesulfonamide groups, butanesulfonamide groups such as butanesulfonamide groups, triflides Olomethanesulfone Halide-substituted alkylsulfonamide groups such as amide group, difluoromethanesulfonamide group or trifluoroethanesulfonamide group, aryl groups such as phenyl group or naphthyl group, furan, thiophene, oxazole, 1-H-pyrazole, 1 H-pyrazole, 3 H-pyrazole, imidazo-inole, thiazole, oxazole, isoxazole, isothiazole, tetradihydrofuran, pyrazolidine, pyridine, pyran, pyrimidine, pyrazine Alkylamino groups such as methylamino group, ethylamino group, propylamino group, and arylamino groups such as phenylamino group, amide groups such as acetylamino group or benzoylamino group, fluorine atom, chlorine atom, bromine atom Or iodine atom halo Examples of the acyl group include a gen atom, a acetyl group and a benzoyl group.

Moreover, the compound of the present invention represented by the general formula (1) is a novel compound, and the compound represented by the general formula (1) can be produced by the method described in the following reaction formula (1).

(Chemical 14) Reaction formula (1)

/ —

[Where R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9, R 10,

A and are the same as those in the general formula (1), and X ₃ represents a leaving group. In the compound represented by the general formula (1 2), as the leaving group represented by X ₃ ,

2

A halogen atom typified by a chlorine atom, an alkoxy group typified by a methoxy group and an ethoxy group, an aryloxy group typified by a phenoxy group, an acyloxy group typified by a acetyloxy group and a benzoyloxy group, and a methoxycarbonyloxy group Representative examples of anoroxycarbonyloxy group, arylcarbonylcarbonyl group represented by phenylcarbonyloxy group, N-hydroxysuccinic acid imide, 1-hydroxybenzotriazole and imidazole group Each can be illustrated.

(\

In the reaction formula (1), the amine amide derivative represented by the general formula (11) or a salt thereof is mixed with a known carbonyl compound represented by the general formula (12) in a solvent-free or solvent-free manner with a base or base and By reacting in the presence of a metal reagent such as trialkylaluminum, the diamine derivative represented by the general formula (1) can be produced.

As the base of reaction formula (1), alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali hydroxides such as magnesium hydroxide and calcium hydroxide, earth metals such as sodium hydride and potassium hydride Alkali metal hydrides such as sodium methoxide, alkali metal alkoxides such as sodium metoxide, alkali metal oxides such as sodium oxide, carbonates such as potassium carbonate and sodium carbonate, triphosphate Phosphoric acid salts such as strong rhodium, trisodium phosphate, dihydrogen phosphate monobasic, phosphate monobasic phosphate, sodium acetate, acetates such as sodium acetate, pyridine, 4- (dimethylamino) pyridine, Organic bases such as triethylamine, imidazole, diazabicycloundecene and the like can be mentioned.

The amount of these bases used is not particularly limited, and can be used as a solvent when the above organic bases are used. When these bases are used, the solvents used in the reaction include water, methanol, ethanol, alcohols such as propanol and butanol, halogenated hydrocarbons such as dichloromethane and chloroform, benzene, toluene, and xylene. Aromatic hydrocarbons such as hexane, heptane and other aliphatic hydrocarbons, dimethylformamide (DMF), dimethylacetamide (DMA;), dimethylsulfoxide (DMSO), 1, 3 —Non-proton polar solvents such as dimethyl-2-imidazolidinone (DM I), 1-methyl-2-pyrrolidone (NMP), ethyl ether, isopropyl ether, 1,2-dimethoxetane (DME), tetrahydrofuran ( THF), ethers such as dioxane, and nitriles such as acetonitrile and propionitryl. That.

Examples of the metal reagent of the reaction formula (1) include Grignard reagent, alkylamine, and alkylamine aminomagnesium halide (Bodrou X reaction), lithium aluminum hydride, trimethylaluminum, triethylalminium, etc. be able to. The amount of these metal reagents used is not particularly limited.

When using these metal reagents, the solvents used in the reaction include halogenated hydrocarbons such as dichloromethane and chlorohonolem, aromatic hydrocarbons such as benzene, toluene and xylene, and aliphatic carbons such as hexane and heptane. Examples thereof include ethers such as hydrogen, ethyl ether, isopropyl ether, 1,2-dimethoxetane (DME), tetrahydrofuran (THF), and dioxane.

(2) The reaction temperature and reaction time of the above reaction can be varied over a wide range. In general, the reaction temperature is preferably 1 to 78-200 ° C, more preferably -78 to 100, and the reaction time is preferably 0.0 1 to 50 hours, more preferably 0.1 to 15 hours. It is.

The equivalent amount of the carbonyl compound represented by the general formula (12) is preferably 1 to 2 equivalents, more preferably 1 to 1.2 equivalents relative to the amine derivative represented by the general formula (11).

The amine derivative represented by the general formula (1 1) of the reaction formula (1) and a salt thereof can be produced by the method described in the reaction formula (2) under £ λ.

(Chemical 15) Reaction formula (2)

[Wherein R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9, RIO and A are the same as described above, R 40 is a t-butyl group Alternatively, it represents a benzyl group that may be substituted. ]

In reaction formula (2), the diamine derivative represented by general formula (11) can be produced by reacting the diamine derivative represented by general formula (13) with an acid or by hydrogenation reaction.

Examples of the acid used in this case include hydrogen chloride, hydrogen bromide, sulfuric acid, nitric acid, acetic acid, and trifluoroacetic acid. The amount of these acids used is not particularly limited, and can be used as a solvent. 'The hydrogenation reaction can be carried out in a suitable solvent, in the presence of a catalyst, at normal pressure or under pressure, in a hydrogen atmosphere. Examples of catalysts include palladium catalysts such as palladium-carbon, nickel catalysts such as Raney nickel, cobalt catalysts, ruthenium catalysts, rhodium catalysts, platinum catalysts, etc. Solvents include water, alcohols such as methanol and ethanol, benzene And aromatic hydrocarbons such as toluene, chain or cyclic ethers such as ether, dioxane and tetrahydrofuran, and esters such as ethyl acetate. The reaction temperature and reaction time for the above reaction can be varied over a wide range. In general, the reaction temperature may be appropriately selected from 120 ° C. to the reflux temperature of the solvent to be used, and the reaction time in the range of several minutes to 96 hours.

The diamine derivative represented by the general formula (13) of the reaction formula (2) and a salt thereof can be produced by the method described in the following reaction formula (3). Reaction formula (3)

1 6)

Wherein, R l, R 2, R 3, R4, R 5, R 6, R 7, R 8, R 9, R 1 0, R 40, A and X ₃ have the same meanings as defined above. ]

In the reaction formula (3), the amine derivative represented by the general formula (15) or a salt thereof is mixed with a known amino acid derivative represented by the general formula (14) in a solvent-free or solvent-free manner in a base, a base, and a trihydrate. By reacting in the presence of a metal reagent such as alkylaluminum, a diamine derivative represented by the general formula (13) can be produced.

In this case, the same base as that used in the method represented by the reaction formula (1) can be used. The amount of these bases used is not particularly limited, and can be used as a solvent when the above organic bases are used.

In this case, the same metal reagent as that used in the method represented by the reaction formula (1) can be used. The amount of these metal reagents used is not particularly limited.

In this case, the same organic solvent as that used in the method represented by the reaction formula (1) can be used.

The amount of the compound represented by the general formula (14) is 1 to 4 equivalents, preferably 1 to 2 equivalents relative to the amine derivative represented by the general formula (15).

The reaction temperature and reaction time for the above reaction can be varied over a wide range. Generally, the reaction temperature is 120 to 200 ° C, preferably 0 to 100 ° C. The reaction time is from 0.01 to 50 hours, preferably from 0.1 to 15 hours.

The compound represented by the general formula (14) in the reaction formula (3) is prepared by converting the amino acid derivative represented by the general formula (16) into thionyl chloride, oxalyl chloride, phosgene, oxychloride, Anti-phosphorus such as phosphorus chloride, phosphorus pentachloride, thionyl bromide, phosphorus tribromide, jetylaminosulfur trifluoride, 1, 1'-carbonylbis- 1H-imidazole, etc. It can be manufactured by the usual method of adapting.

In addition, the compound represented by the general formula (14) in the reaction formula (3) is obtained by converting the amino acid derivative represented by the general formula (16) into alcohols such as methyl alcohol and ethyl alcohol, phenol, nitrophenol. It can also be produced by a conventional method of reacting with phenols such as

In addition, the compound represented by the general formula (14) in the reaction formula (3) is a compound having an amino acid derivative represented by the general formula (16), such as methyl formate or phenyl formate. It can also be produced by a conventional method of reacting with lipates.

In addition, the compound represented by the general formula (14) in the reaction formula (3) is obtained by converting the amino acid derivative represented by the general formula (16) into N-hydroxysuccinic acid imide, 1-hydroxybenzazotriazole, etc. Can also be produced by a conventional method of reacting with.

The amine derivative represented by the general formula (15) of the reaction formula (3) and the salt thereof are other than those commercially available. For example, the Gabriel method, the Delpin method, the cyan group or amide, imine, oxime, etc. Can be easily prepared by the method described in Tetrahedron Asymmetry, 1st 1st, 1907 (2000). it can.

The diamine derivative represented by the general formula (13) can also be produced by the method described in the reaction formula (4).

(Chemical 1 7)

Reaction formula (4)

[Wherein, R 1, R 2, R 3, R 4., R 5, R 6, R 7, R 8, R 9, R 10, R 40 and A are the same as described above. ]

In the reaction formula (4), the amin derivative represented by the general formula (15) and a salt thereof are reacted with the known amino acid derivative represented by the general formula (16) in the absence of a solvent or in a solvent. As the condensing agent in the case where the diamine derivative represented by the formula (1 3) can be produced, N, N′-dicyclohexylcarbodiimide,

1 'monocarbonyl bis 1 H-imidazole, 1-ethyl 1- (3-dimethyl) Tylaminopropyl) Carposiimide hydrochloride, 2-chloro 1,3-dimethyl imidazole, etc. can be used.

The amount of the condensing agent to be used is 1 to 3 equivalents, preferably 1 to 1.5 equivalents, relative to the compound represented by the general formula (16).

The amount of the carboxylic acid derivative represented by the general formula (16) is 1 to 2 equivalents, preferably 1 to 1.2 equivalents relative to the amine derivative represented by the general formula (15). The reaction temperature and reaction time for the above reaction can be varied over a wide range. In general, the reaction temperature is 120 to 200 ° C, preferably 0 to 100 ° C. The reaction time is from 0.01 to 50 hours, preferably from 0.1 to 15 hours.

In the reaction formula (4), the compound represented by the general formula (16) reacts the corresponding amino acid with carboxylic acid formate, carbonates such as O-methyl-0_ (p-nitroxyphenyl) carbonate, etc. Can be produced by a conventional method.

Returning to the reaction formula (1), the compound represented by the general formula (1 2)

The known carboxylic acid derivatives represented by 1 7) are thionyl chloride, oxalyl chloride, phosgene, phosphorus oxychloride, phosphorus trichloride, phosphorus pentachloride, thionyl bromide, phosphorus trichloride, jetylaminosulfurate. It can be produced by a conventional method in which it is reacted with refluoride, 1,1 ′ monocarbonylbis-1,1H-imidazole or the like.

In addition, the compound represented by the general formula (12) in the reaction formula (1) is obtained by converting a known carboxylic acid derivative represented by the general formula (17) into alcohols such as methyl alcohol and ethyl alcohol, phenol, nitro It can also be produced by a conventional method of reacting with phenols such as phenol.

In addition, the compound represented by the general formula (1 2) in the reaction formula (1) is a known carboxylic acid derivative represented by the general formula (1 7), such as chloroformate such as methyl chloroformate and phenyl chloroformate. It can also be produced by a conventional method of reacting with esters.

In addition, the compound represented by the general formula (1 2) in the reaction formula (1) is obtained by reacting a known carboxylic acid derivative represented by the general formula (17) with N-hydroxysuccinic acid imide, 1-hydroxyl. It can also be produced by a conventional method of reacting with benzotriazole or the like.

The compound of the present invention represented by the general formula (1) can also be produced by the method described in the reaction formula (5).

(Chemical 1 8) Reaction formula (5)

[Where R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9, R 10,

A and are the same as described above. ]

In the reaction formula (5), the amine derivative represented by the general formula (11) and the salt thereof are reacted with the known carboxylic acid derivative represented by the general formula (17) in a solvent-free or solvent, The diamine derivative represented by the general formula (1) can be produced. In this case, the condensing agent includes N, N'-dicyclohexylcarbodiimide, 1, 1'-canolebonino lebis mono 1 H-imidazole 1-ethyl 3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 2-chloro-1,3-dimethylimidazole chloride, etc. can be used.

The amount of the condensing agent used is ˜3 equivalents, preferably 1˜: 1.5 equivalents, relative to the compound represented by the general formula (17).

′ The amount of the carboxylic acid derivative represented by the general formula (17) is 1 to 2 equivalents, preferably 1 to 1.2 equivalents, relative to the amine derivative represented by the general formula (11). The reaction temperature and reaction time for the above reaction can be varied over a wide range. In general, the reaction temperature is 120 to 200 ° C, preferably 0 to 100 ° C. The reaction time is from 0.01 to 50 hours, preferably from 0.1 to 15 hours.

The compound of the present invention represented by the general formula (1) can also be produced by the method described in the reaction formula (6).

(Chemical formula 1 9) Reaction formula (6)

(18) [Wherein, R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9, R 10, A, X ₃ and are the same as defined above. ]

In the reaction formula (6), the amine derivative represented by the general formula (18) or a salt thereof is mixed with a known compound represented by the general formula (14) in a solvent-free or solvent-free manner in a base or base. By reacting in the presence of a metal reagent such as trialkylaluminum, the diamine derivative represented by the general formula (1) can be produced.

The amount of the compound represented by the general formula (14) is 1 to 4 equivalents, preferably 1 to 2 equivalents relative to the amine derivative represented by the general formula (18).

The reaction temperature and reaction time for the above reaction can be varied over a wide range. Generally, the reaction temperature is -20 to 200 ° C, preferably 0 to 100 ° C. The reaction time is from 0.01 to 50 hours, preferably from 0.1 to 15 hours.

The compound of the present invention represented by the general formula (1) can also be produced by the method described in the reaction formula (7).

(Chemical 20)

Reaction formula (7)

A and Gh are the same as described above. ]

In the reaction formula (7), by reacting the amine derivative represented by the general formula (18) and its salt with the known carboxylic acid derivative represented by the general formula (16) in a solvent-free or solvent, A diamine derivative represented by the general formula (1) can be produced. In this case, the condensing agent includes N, N'-dicyclohexyl carpositimide, 1, 1'-canolebonino lebis 1 H-imidazole, 1-etenore 1- (3-dimethylaminopropyl) Carbodiimide 'hydrochloride, 2-chloro 1, 1-dimethyl imidazolium chloride, etc. can be used.

The amount of the carboxylic acid derivative represented by the general formula (16) is 1 to 2 equivalents, preferably 1 to 1.2 equivalents relative to the amine derivative represented by the general formula (18). The reaction temperature and reaction time for the above reaction can be varied over a wide range. Generally, the reaction temperature is -20 to 200 ° C, preferably 0 to 100 ° C. The reaction time is from 0.01 to 50 hours, preferably from 0.1 to 15 hours.

The compound of the present invention represented by the general formula (1) can also be produced by the method described in the reaction formula (8).

(Chemical formula 2 1) Reaction formula (8)

Wherein, R l, R 2, R 3, R4, R 5, R 6, R 7, R 8, R 9, R 1 0, A, X 3 and C have the same meanings as defined above. ]

In the reaction formula (8), the amine derivative represented by the general formula (19) and a salt thereof are mixed with a known compound represented by the general formula (20) in the absence of a solvent or a solvent in the presence of an abasic or base. The diamine derivative represented by the general formula (1) can be produced by performing the reaction below.

In this case, the same base as that used in the method represented by the reaction formula (1) can be used. The amount of these bases used is not particularly limited, and can be used as a solvent when the above organic bases are used. In this case, the same organic solvent as that used in the method represented by the reaction formula (1) can be used.

The amount of the compound represented by the general formula (20) is 1 to 4 equivalents, preferably 1 to 2 equivalents relative to the diamine derivative represented by the general formula (19).

The reaction temperature and reaction time for the above reaction can be varied over a wide range. In general, the reaction temperature is 120 to 200 ° C, preferably 0 to 100 ° C. The reaction time is from 0.01 to 50 hours, preferably from 0.1 to 15 hours.

The amine derivative represented by the general formula (19) of the reaction formula (8) and a salt thereof can be produced by the method described in the reaction formula (9).

(Chemical 2 2)

Reaction formula (9)

[Wherein R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9, R 10, A and Qi are the same as above, and R 1 is t-butyl] Represents a group or an optionally substituted benzyl group. ]

In reaction formula (9), the diamine derivative represented by general formula (19) can be produced by reacting the diamine derivative represented by general formula (1) with an acid or by hydrogenation reaction.

Examples of the acid used in this case include hydrogen chloride, hydrogen bromide, sulfuric acid, nitric acid, acetic acid, and trifluoroacetic acid. The amount of these acids used is not particularly limited, and can be used as a solvent.

As the catalyst for the hydrogenation reaction, the same catalyst as that used in the method represented by the reaction formula (2) can be used.

As the solvent in this case, the same solvent as that used in the method represented by the reaction formula (1) can be used.

The reaction temperature and reaction time for the above reaction can be varied over a wide range. In general, the reaction temperature may be appropriately selected from 120 ° C. to the reflux temperature of the solvent to be used, and the reaction time in the range of several minutes to 96 hours. The compound represented by the general formula (20) in the reaction formula (8) usually reacts the corresponding alcohols with phosgenes such as phosgene and triphosgene, and chloroformate esters such as phenol oleoresin. It can be manufactured by the method.

The diamine derivative represented by the general formula (1) may have an asymmetric carbon depending on the type of the substituent, and may exist as an optical isomer, a diastereoisomer, a racemate, and a mixture of any ratio. All isomers of this type, as well as mixtures thereof, are also encompassed by the diamine derivatives used in the present invention.

The diamine derivative represented by the general formula (1) of the present invention is particularly suitable for the pesticidal fungus of Plasmopara viticola (Pseudoperonospora cubensis), the fungus (Pseudoperonospora cubensis) Phytophthora infestans), lawn physium disease (

Pythium aphanidermatum other) such as the batter was for powerful sterilization operation in a number of eggs fungi to be representative, Plasmopara species, Pseuaoperonosporaft _s Peronospora, plague a wide variety of plants caused by pathogens Pythium spp., Base and the disease, seedling blight Exhibits a very good control effect against Pythium disease. It also has a strong bactericidal activity against rice blast fungus (Pyricularia oryzae), and exhibits excellent control effects against rice blast.

Examples of the bactericides used in the pest control composition of the present invention include industrial bactericides such as anti-corrosion and anti-bacterial agents, agricultural and horticultural bactericides, medical and disinfectant bactericides, etc. As an antibacterial agent, it exhibits an excellent control effect.

Such fungicides include triadimephone, hexaconazole, propiconazonole, ipconazonole, prochloraz, trifnoremizonole, tebuconazonole, epoxiconazonore, difuenoconazole, funoresilazole, triadimenole fol Quinconazole, Vitertanol

, Tetraconazole, triticonazonole, fur triafonore, penconazole, diniconasole, fenbuconazonole, bromconazonore, imibenconazonore, simeconazole, microbutanyl, himexazole, imazalil, framite Azol fungicides such as diazole, oxyspoconazole, oxyspoconazole fumarate, pefazoate and prothioconazole, pyrimidin fungicides such as pyriphenox, fenarimol, nurimol and buprimate, mepanipyrim, cyprodinil, pyrimethanil , Ailinopyrimidine fungicides such as diflumetrim, asylalanine fungicides such as metalaxyl, metalaxyl-M, oxadixil, benalaxyl, Ofanate methyl, Benomyl, Benzimidazole fungicides such as carbendazim, fuberidazolinole and thiabendazole, organic sulfur-based fungicides such as manzeb, proneb, zineb, methylam, mannebu, ziram, thiuram, ambam, polycarbamate, thiadiazine, tetracola mouth Organochlorine fungicides such as isophthalonitrile, ethaboxam, oxycarboxine, carboxin, funoletranil, sylthiofam, carboxam fungicides such as meproninole, boss strength lid, dimethomorph, fenprovidin, fenpropimonolev, spiroxamine, tridemorph Morpholine fungicides such as fulmorph, azoxis trobin, cresoxime methyl, metminos trobin, olisus trobin, funoleoxas trobin, to Diphlooxibic fungicides such as rifloxys trobin, dimoxis trobin, pyraclos trobin, picoxis trobin, etc., dicarboxymide sterilizers such as diplodione, procymidone, vinclozolin, and clozolineate , Methylisothiocyanate, Chlorpicrine, Metasulfocarp, Hydroxyisoxazole, Hydroxyisoxazolinolecalium, Ecomezonole, DD, Carbam, Methyl iodide, Basic Copper fungicides such as copper chloride, basic copper sulfate, copper nonylphenol sulfonate, copper oxine, DBEDC, anhydrous copper sulfate, copper sulfate pentahydrate, cupric hydroxide, inorganic sulfur, hydrated sulfur agent, Lime sulfur mixture, zinc sulfate, fern, sodium hydrogen carbonate, carbonated water Inorganic fungicides such as phyllium, hypochlorite and metallic silver, organic fungicides such as edifenphos, tonolecrophosmethinole, Josetinore, iprovenfos, dinocap and pyrazophos, carpropamide, fusalide and Melanin biosynthesis inhibitors such as riccyclazole, pyroxylone, diclocimet, and phenoxanil, bactericides such as kasugamycin, validamycin, polyoxin derivatives, blasticidin S, tech mouth phthalam, oxytratracycline, mildiomycin, streptomycin, etc. Antibiotics such as rapeseed oil, natural product fungicides such as rapeseed oil and machine oil, carbamate fungicides such as Benchavalycarb isopropyl, iprovarial carp, propamocalp, and dietofencalp, fluoride, fludioxonil Pyrrole fungicides such as fenpiclonil, plant activators that induce plant disease resistance such as probenazole, cibenzolral S-methyl, thiazinyl, quinoline fungicides such as quinoxyphene, oxolinic acid, cyflufenamide, Fenhexamide, metrafenone, picobenzamide, proquinazide, famoxadone, cyazofamide, fenamidone, zoxamide, chlorothalonil, simoxanyl, quibutane, dithianone, fluazinam, phorpet, diclof Ruanide, trifolin, isoprothiolane, fueliszone, dichromedin, pencyclon, quinomethionate, iminoctadine acetate, iminoctadine albylate, guazatine, chloroneb, organonickel, dodine, quintozene, tolylfluanid, anilazine, Nitrotal isopropyl, Phenitropane, Dichlorane, DPC, Dimethylyl monole, Benchazolene, Frumethnoin, Mandipropamide, (RS) — N— [2— (1,3-Dimethylbutyl) thiophene 3-Inole] 1-methyl 3-trifluoromethyl 1 1 H-pyrazole 1- 4 carboxamide (This compound is described in Japanese Patent No. 3 1 64 7 6 2, and describes its bactericidal activity and production method. In addition, the common name for which the application is pending is Pentiovir. ), And the following general formula (2), the general formula (3), the general formula (4), the general formula (5), sterilization agents such as compounds represented by the general formula (6) below.

(Chemical 2 3)

The compound of the general formula (2) is described in WO 0 1 1 0 8 25 and describes the bactericidal activity and the production method.

(Chemical 24

The compound of the general formula (3) is described in U S 6 6 20 8 12 and describes the bactericidal activity and the production method.

(Chemical 2 5)

The compound of the general formula (4) is described in WO 0 3 0 7 9 78 8 and describes the bactericidal activity and the production method. (Chemical 26)

[Wherein R 11 represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an arylalkyl group or a heterocyclic alkyl group, and R 12 and R 17 are R 1 3 and R 14 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, R 15 and R 16 each represent a hydrogen atom, R 1 8 Represents an aryl group or a hetero ring. ]

The compound of the general formula (5) is described in W 0 200 3 008 372, and the bactericidal activity and production method are described.

(Chemical 2)

[Wherein R 19 is an alkyl group having 1 to 6 carbon atoms substituted with halogen, a cycloalkyl group having 3 to 6 carbon atoms substituted with halogen, or an alkenyl group having 2 to 6 carbon atoms substituted with halogen. R 20 and R 25 each represent a hydrogen atom, R 21 and R 22 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, and R 23 and R 24 each represent hydrogen. R 26 represents an aryl group or a heterocyclic ring. ]

—The compound of the general formula (6) is described in WO 200 504 24 74, and the bactericidal activity and production method are described.

Further, as insecticides that can be used in the pest control composition of the present invention, aresulin, tetramethrin, resmethrin, phenothrin, furametrin, permethrin, cypermethrin, Deltamethine, Cihalothrin, Siflutrin, Fuengpro No. Toluene, tralomethrin, cycloprotorin, flucitrinate, full variate, actinolin, teflurin, bifentolin, empentolin, beta-saifu norelin, fennorelate, esfenolate, funolebrosi Pyrethroid insecticides such as trinate, methonoreslin, profuzoleslin, dimefnoreslin, shiranovolefen, insecticide chrysanthemum extract, etofenprox, no, norefenprox, DDVP, cyanofos, fenthion, phenyltrothion Tetrachlorvinfos, Dimethinolevinephos, Propafos, Methinoreparathion, Temefos, Hoxime, Acepheto, Isofenfos, Salicion, DEP, EPN, Ethion, Mecarbam, Pyridafen ON, diazinon, pyrimifosmethyl, etrimphos, isoxathion, quinalphos, chronolepyrifosmethyl, chronoleviriophos, hosalon, phosmet, methidathion, oxidized mouth phos, bamidotion, malathion, fentoate, dimethoate, formothion , Thiomethone, etizolethiomethone, holate, tenolebufos, profenofos, prothiofos, surprofos, pyracrofos, monocrotofos, naredo, phostiazate, triglycol norephone, etoprophos, kazusafos, chronofenmethionone, diclofenthione tho , Methamidophos, dichlorvos, tebupyrimfos, ometoate, triazofos, oxydemeton-methyl, azinephos-methyl, Chronoretoxifos, dicrotofos, disnorefothone, fenamifos, phosphaamidon, chlormefos, demethonone s-methyl, mevinphos, parathion and other organophosphorus insecticides, NAC, MTMC, MIPC, BPMC, XMC, PHC, MPMC, Ethiophene Kanoleb, Vendano Canoleb, Piri Mikanoleb, Force Nore Bosnorefan, Benfuracarb, Mesominore, Oxamil, Aldicarp, Tiosikarp, Alani Kanoleb, Force / Repofuran, Meticanoreb, Fenoticanoleto, Hono Carbamate insecticides such as methyl carbamate, propoxal, isoprocarb, imidacloprid, nitenbiram, acetamiprid, dinotefuran, chiametoxam, thiacloprid, neonico such as clothianidin Organic chlorinated insecticides such as chinoid insecticides, bromopropyrate, dicophore, endsulfan, and Linda, difnolevenzron, cronorenozuron, tefnorezuron, trifnolem mouth, ph / Lefenotaslon, Funolecycloxuron, Hexafunoremron, Funores mouth, Difenthiuron, Nonokuneron, Novifunolemlon, Bistolynorelon, Kuma Mahenozide, Norofenozide, Metoxifenadron, Norelone Insect growth regulators such as triazamate, nicotine sulfate, polynactin complex , Abamethatin, milbemectin, repimectin, BT (Bacillus thuringiensis) agent, natural insecticides such as spinosad, rotenone, cartap, thiocyclam, vensnoretap, pimetrozin, fiproninole, buprofezin, phenoxyfenol Metoprene, Hyde Mouth Plain, Quinoprene, Endos Norephan, Triazuron, Tebufenozide, Benzopine, Emamectin, Emamectin Benzoate, Funorepyrazofos, Funore Acribium, Funorefu Engine, Indoxacarp, Tolenfenhalod, Gamma Lin, Ethiprole, Acetoprole, Amidoflumet, Chlorfenavir, Phroniform Mid, Funolefenem, Pyridalyl, Sodium Oleate, Potassium oleate, azadeiractin, carbam, carbam sodium, propargite, azocyclotin, benzoximate, methanolide, protrifen boot, benclothiaz, flubenzamide, metaflumizole, and the following general formula (7), general formula (8), Insecticides such as compounds represented by general formula (9) and general formula (10) can be mentioned.

(Chemical 2)

[In the formula, R 27 represents a methyl group or a chloro group, R 28 represents a methyl group, a chloro group, a bromo group, or a cyano group, and R 29 represents a chloro group, a bromo group, a trifluoromethyl group, or a cyanomethoxy group. R 30 represents a methyl group or an isopropyl group. ]

The compound of the general formula (7) is described in WO 2003 3 1 5 5 19 and describes the insecticidal activity and the production method.

(Chemical 29)

(8)

[Wherein R 3 1 is 1, 1, 1, 2, 3, 3, 3—heptafnoroleol 2-propyl group or 1, 1, 2, 2, 3, 3, 3—heptafluoro 1— Represents a propyl group. ]

The compound of the general formula (8) is described in Japanese Patent Application Laid-Open No. 2001-342 186, and describes the insecticidal activity and the production method.

(Chemical 3)

[Wherein, Xi is a hydrogen atom or a fluorine atom, R3 2 and R3 3 are a hydrogen atom and an alkyl group having 1 to 4 carbon atoms, respectively, Q ₂ is a phenyl group, a halogen atom, or a carbon number An alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, a haloalkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms, and 2 to 4 carbon atoms Haloanolequinyl group, cycloalkyl group having 3 to 6 carbon atoms, halocycloalkyl group having 3 to 6 carbon atoms, alkoxy group having 1 to 3 carbon atoms, haloalkoxy group having 1 to 3 carbon atoms, 1 to 3 carbon atoms Alkylthio group, haloalkylthio group having 1 to 3 carbon atoms, carbon number; ~ 3 Anolequinolesulphinyl group, carbon number :! A haloalkylsulfinyl group having 3 to 3, an alkylsulfonyl group having 1 to 3 carbon atoms, a haloalkylsulfonyl group having 1 to 3 carbon atoms, an alkylamino group having 1 to 4 carbon atoms, and a carbon number 1 ~ 4 dialkylamino group, cyano group, nitro group, hydroxyl group, alkylcarbonyl group having 1 to 4 carbon atoms, alkylcarbonyloxy group having 1 to 4 carbon atoms, alkoxycarbonyl group having 1 to 4 carbon atoms, acetylamino A substituted phenyl group having one or more substituents which may be the same or different selected from a phenyl group, a pyridyl group, or a halogen atom, an alkyl group having 1 to 4 carbon atoms, and having 1 to 4 carbon atoms A macroalkyl group, an alkenyl group having 2 to 4 carbon atoms, a haloalkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms, a haloalkynyl group having 2 to 4 carbon atoms, a cycloalkyl having 3 to 6 carbon atoms Group, halocycloalkyl group having 3 to 6 carbon atoms, alkoxy group having 1 to 3 carbon atoms, haloalkoxy group having 1 to 3 carbon atoms, alkylthio group having 1 to 3 carbon atoms, and 1 to 3 carbon atoms Haloalkylthio group, C1-C3 alkylsulfinole group, Carbon number! ~ 3 halo anole kirs no refinil group, carbon number :! ~ 3 alkyls / rehoninole group, carbon number :! ~ 3 halo anorequinoles norephonyl group, carbon number :! C-4 alkylolamino group, C1-C4 dialkylamino group, Cyano group, nitro group, hydroxyl group, C1-C4 alkylcarbonyl group, C1-C4 alkylcarboninoleoxy group, carbon Q ₁ is a pyridyl group having one or more substituents which may be the same or different and is selected from an alkoxy group, a noblenyl group, a acetylamino group, a phenyl group, and the like represented by formula (A).

(Chemical 3 1)

(In the formula, Y i and Y ₅ may be the same or different, halogen atom, carbon number 1

~ 4 alkyl group, 1 ~ 4 carbon haloalkyl group, carbon number :! -4 alkoxy group, haloalkoxy group having 1 to 4 carbon atoms, alkylthio group having 1 to 3 carbon atoms, haloalkylthio group having 1 to 3 carbon atoms, alkylsulfinyl group having 1 to 3 carbon atoms, 1 to 3 carbon atoms Haloalkylsulfinyl group, an alkylsulfonyl group having 1 to 3 carbon atoms, a haloalkylsulfonyl group having 1 to 3 carbon atoms, and a cyano group, Υ ₃ is a perfluoroalkyl group having 2 to 6 carbon atoms, and 1 to 6 carbon atoms Perfluoroalkylthio group, perfluoroalkylsulfininole group having 1 to 6 carbon atoms, and 1 to 6 carbon atoms. Represents a fluoroalkylsulfonyl group, and Υ ₂ and Υ ₄ are a hydrogen atom, a halogen atom, and a carbon number of 1 to 4 represents an alkyl group. ) ]

The compound of the general formula (9) is described in WO 2005-73 165, and describes the insecticidal activity and production method.

(Chemical 32)

Wherein, X ₂ is a hydrogen atom or a fluorine atom, R35, R36 are each a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, R34 is Kill group having 1 to 6 carbon atoms, carbon atoms A haloalkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a haloalkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a haloalkynyl group having 2 to 6 carbon atoms, and 3 to 3 carbon atoms An cycloalkyl group having 8 carbon atoms, a halocycloalkyl group having 3 to 8 carbon atoms, one — Zi— R37 (wherein is an alkylene group having 1 to 4 carbon atoms, an alkylene group having 2 to 4 carbon atoms, 3 to 3 carbon atoms) 4 alkylene groups, haloalkylene groups having 1 to 4 carbon atoms, haloalkylene groups having 2 to 4 carbon atoms, haloalkylene groups having 3 to 4 carbon atoms, R37 is a hydrogen atom, 1 to carbon atoms 6 alkyl groups, alkenyl groups having 2 to 6 carbon atoms, alkynyl groups having 2 to 6 carbon atoms, 1 to 6 carbon atoms A haloalkenyl group having 2 to 6 carbon atoms, a haloalkenyl group having 2 to 6 carbon atoms, Zi being —O—, — S—, one SO_, one S0 ₂ —, _C (= 0) _, One C (= 0) O—, One OC (= 0) One, — N (R38) ―, — C (= 0) N (R38) —, One N (R38) C (= 0)-(R 38 Represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkylcarbonyl group having 1 to 4 carbon atoms, a haloalkylcarbonyl group having 1 to 4 carbon atoms, or an alkoxycarbonyl group having 1 to 4 carbon atoms. -E ₂ -R39 (wherein E2 is an alkylene group having 1 to 4 carbon atoms, an alkylene group having 2 to 4 carbon atoms, an alkynylene group having 3 to 4 carbon atoms, or 1 to 4 carbon atoms) A haloalkylene group having 2 to 4 carbon atoms, a haloalkynylene group having 3 to 4 carbon atoms, R39 represents a cycloalkyl group having 3 to 8 carbon atoms, a halocycloalkyl group having 3 to 8 carbon atoms, Ciano group, D Toro group, hydroxyl group, phenyl group, or the same or different, halogen atom, carbon number :! ~ 6 anoalkyl group, 1 ~ 6 carbon haloalkyl group,! An alkoxy group having 6 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, a haloalkylthio group having 1 to 6 carbon atoms, an alkylsulfinyl group having 1 to 6 carbon atoms, and a carbon number of 1 to 6 no-guchi alkinores norefinyl group, carbon number :! C 6 alkylsulfonyl group, C 1-6 haloalkylsulfonyl group, cyano group, nitro group, hydroxyl group, C 1-4 alkylcarbonyl group, C 1-4 haloalkyl carbonyl group, carbon number A substituted fluor having one or more substituents selected from an alkylcarbonyloxy group having 1 to 4 carbon atoms and an alkoxycarbonyl group having 1 to 4 carbon atoms: diaryl group, pyridyl group, or halogen atom, carbon number 1 A substituted pyridyl group having one or more substituents selected from a haloalkyl group having ˜6, a haloalkoxy group having 1 to 6 carbon atoms, a phenyl group, and a tetrahydrofuran group; Q ₄ is a general formula (B):

(Chemical 3 3)

(Wherein Y ₆ and may be the same or different, a halogen atom, carbon number 1

~ 4 alkynole groups, carbon number :! ~ 4 haloalkyl group, 1 ~ 4 carbon anoalkoxy group, 1 ~ 4 carbon haloalkoxy group, 1 ~ 3 carbon alkylthio group, carbon number:! ~ 3 haloalkylthio group, 1 ~ 3 carbon atom Alkylsulfier group, carbon number:! ~ 3 halo anorequinolesulphinyl group, carbon number :! 1-3 of § Honoré Kill sulfonyl group, haloalkylsulfonyl groups of from 1 to 3 carbon atoms, indicates Shiano group, Upsilon ₈ par full O b alkyl group having 2 to 6 carbon atoms, Pafuruoro 1 to 6 carbon atoms An alkylthio group, a perfluoroalkylsulfininole group having 1 to 6 carbon atoms, or a monofluoroalkylsulfonyl group having 1 to 6 carbon atoms, Υ ₇ and Υ ₉ are a hydrogen atom, a halogen atom, carbon This represents an alkyl group of the number 1 to 4. ) ]

The compound of the general formula (1 0) is described in W 2O 2 0 5-2 1 4 8 8 and describes the insecticidal activity and the production method.

As an acaricide that can be used in the pest control composition of the present invention, chlorbendilate, phenisobromolate, tetradiphone. CPCBS (chlorfenson) , BPPS, Quinomethionate, Amitraz, Benzomate, Hexithiazox, Fenbutazin oxide, Sihexatin, Dienochlor, Clofuentezin, Pyridaben, Fenpyroximate, Fuanazaquine, Tebufenvirado, Pyrimidinophene, Tosechinose Examples include etoxazolinole, spirodiclofen, spinomesifen, amidfulmete, and diflovidazine.

As mentioned above, some of the compounds mentioned as fungicides, insecticides and acaricides can take stereoisomers, but these isomers are also included in the present invention.

The pest control composition of the present invention contains at least one compound of one or more other fungicides, insecticides, and acaricides in an amount of 0.001 to 95% by weight, preferably 0.01 to 80% by weight. % contains. In addition, the amount of active ingredient of the pest control composition of the present invention is usually 0.5 to 20% by weight for powders, 5 to 50% by weight for emulsions, 10 to 90% by weight for wettable powders, granules 0.1 to 20% by weight for agents and 10 to 90% by weight for flowable formulations. On the other hand, the amount of carrier in each dosage form is usually 60 to 99% by weight for powders, 40 to 95% by weight for emulsions, and 10 to 90% for wettable powders. /. 80 to 99% by weight for granules and 10 to 90% for flowable formulations. It is. The amount of adjuvant is usually 0.1 to 20 weight for powders. /. 1 to 20% by weight for emulsions, 0.1 to 20% by weight for wettable powders, 0.1 to 20% by weight for granules, and 0.1 to 20% by weight for flowable formulations.

The agent containing the pest control composition of the present invention as an active ingredient is algae

(Oomycetes), ascomycetes (Ascomycetes), non-generic fungi (Deuteromycetes), basidiomycetes, vegetables caused by other pathogenic fungi (Plasmodiophoromycetes) and other pathogens, fruit trees, rice, Suitable for controlling a wide variety of plant diseases including moss, flower buds and turfgrass.

Next, specific disease names (bacteria names) are given as non-limiting examples. For example, rice potato pattern (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), coat blight

(Rhizoctonia solani, 'Idiot--Disease (Gibberella f yiKuroi Yahhi, Num 禹 (seed AL blight caused by if (Pythium graminicola, etc.)), Mussels (Erysiphe graminis f.sp.hordei! I.sp. tntici), macula;) 丙 (Pyrenophora graminea), Pyrenophora teres, red force, Gibberella zeae, rust ί 丙 (Puccinia struformis; P. graminis; P. recondita; P. hordei) ), Snow rot (Typhula sp .; Micronectriella nivalis), Bare smut (Ustilago tritici; U. nuda), Eye spot disease (Pseudocercosporella herpotrichoides), Cloud rot (Rhynchosporium secalis), Leaf blight (Septoria tritici), Blight (Leptosphaeria) nodorum), Brown snow rot caused by Pythium spp. (Pythium iwayamai etc.) Grape downy mildew (Plasmopara viticola), Tsudonko ί 丙 (Uncinula necator), Black and Tsutsu; ^ (Elsinoe ampelina), 晚腐;) 丙(Glomerella cingulata), bi;) 丙 (Phakopsora ampelopsidis), apple tsutonko; / 丙 (Podosphaera leucotricha), black scab (Venturia inaequalis), spotted deciduous bud (Alternaria mail eight scab (Gymnosporangium yamadae), moni S disease (Sclerotinia mali), rot (Valsa mali), pear black spot (Alternaria kikuchiana), black star (Venturia nashicola), red star (Gymnosporangium)

haraeanum), pear plague (Phytophthora cactorum), peach blight

(Sclerotinia cinerea), black star ¾ (Cladosporium carpophiium), fomopsis spoilage;) op (Phomopsis sp.), Epilepsy lye (Phytophthora sp.), Ash rot (Gloeosporium kaki), deciduous disease (Cercospora kaki; Mycosphaer nawae), cucumber downy mildew (

Pseudoperonospora cubensis) Epidemic 3 (Phytophthora melonis, Phytophthora nicotianae, Phytophthora drechsleri), powdery mildew (Sphaerotheca fuliginea) ΪΖ · Bird 3 丙 (Pythium vezans, hizoctonia solani), Ring-root disease (Alternaria solani), Leaf force, Bite;) 丙 (Cladosporium fulvam, Root i¾ disease (Pythium myriotylum, Pythium dissotocum) _s eggplant powdery mildew ( Erysiphe cichoracoarum), plague (Phytophthora infestans), rot (;) (Phytophthora capsici), black spot of Brassicaceae (Alternaria japonica), white spot (Cercosporella brassicae), root-knot (Plasmodiophora brassicae) (Peronospora brassicae), white onion throwing;) 丙 (Phytophthora porri), blight (Puccinia allii), Guise throw (Phytophthora megasperma) Black depression (Elsin oe glycines), black spot disease (Diaporthe phaseololum), green bean anthracnose (Colletotrichum lindemuthianum), lacquered black astringent 丙 (Mycosphaerella personatum), spotted rice cake (Cercospora arachidicola), endowed powdery mildew (Erysiphe pisi), downy mildew (Peronospora pisi), Phytophthora infestans, 复 ¾ 炳 (Alternaria solani), exobasidium reticulatum, white star;! 丙 (Elsinoe leucospila, Tano) Red Star Disease (Alternaria longipes), Tsutonto Disease (Erysiphe cichoracearum eight

(Colletotrichum tabacum), sugar beet (Cercospora beticola), bee; Peronospora schachtii, black leaf disease (Diplocarpon rosae), downy mildew (Peronospora sparsa), plague (Phytophthora megasperma), Tsuton # 3 (Sphaerotheca pannosa) , Chrysanthemum brown spot (Septoria chrysanthemi-indici)> White rust (Puccinia horiana), Phytophthora cactorum ^ Tycho no Uto / * 丙 (Sphaerotheca humuli), Phytophthora (Phytophthora nicotianae), Fruit rot Pythium ultimum), cucumbers, tomatoes, strawberries, grapes, etc. Gray mold disease (Botrytis cinerea), mycorrhizal disease (Sclerotinia sclerotiorum), cynomolgus: 7, lacunno tuchi f (Hhizoctonia solani), evening, -Laspot (Sclerotinia homoeocarpa) ヽ Calf, Curdularia geniculata (Puccinia zoysiae), Helmintosporium leaf blight (Cochiliobolus sp.), Rhynchosporium secalis, Les, b Disease (Pyricularia oryzae A / 1 blight (Gaeumannomyces graminis), ash rot (Colletotrichum graminicola) ^ snow rot brown microtuberculosis (Typhula incarnata), snow rot black sclerotia nuclear disease (Typhula ishikariensis), snow rot large fungus Nuclear disease (Sclerotinia borealis), Fairy Ring (Marasmius oreades, etc..), Pishiumu disease (Pythium aphanidermatum, etc.) and the like.

Moreover, the pest control composition of the present invention is effective for pest control. Such pests include, for example, Lepidoptera (LEPIDOPTERA), Bat power (Endoclyta excrescens), Black bat (Endoclyta sinensis), White bat (Palpifer sexnotata Acleris comariana), Lingo cockatoo (Adoxophyes orana iasciata), Teyanoko Kakumon no Maki (Adoxophyes sp.), Lingomon no Maki Maki (Archips breviplicanus), Mitare Kakumon no Maki (Archips fuscocupreanus), Kakmon no Maki (Archips xylosteanus) fur 7ヽノロノ、マキ (Cnephasia cinereipalpana), クロミガ (Cydia kurokoi), クロミ DRINSHINGA (Eucoenogenes aestuosa), RINGCO SINQUI (Grapholita inopinata), NASHHIME Sinchoi (Grapholita molesta) nan Hoya mona Rinko talented hoshinoa adumbratana, mameshin iga (L eguminivora giycinivorella mura Eupoecillia ambiguella, Phalonidia mesotypa, Momo ³ rhohosono maki (Phtheochroides clandestina), Kodlinga (Cydia pomonella), Grape himeno ヽ maki (Endopiza viteana), minoa. (Eumeta japonica), Tamino sword (Eumeta minuscula), Kokuka (Nemapogon granellus) Λ sword (Tinea translucens), Nashichibiga (Bucculatrix) pyrivorella), mosquito moth (Lyonetia clerkella), gypsum moth (Lyonetia prunifoliella), bean moth (Caloptilia soyella), caloptilia theivora, lyngohosaga (Caloptilia zachrysa), phodes ), Nashihoso Katana

(Spulerina astaurota), Myrtle humminga (Phyllocnistis citrella), Grape moth mog riga (Pylylnisnistis toparcha) off Dousu force Shinoku (Paranthrene regalis Kosukashinoku (Synanthedon hector), Tamushika (Stathmopoaa masinissa to force Kino), Imokinoヽmoth (Brachmia triannulella), Wataaka ^ Musi (Pectmophora gossypiella) _N Shah Gaimo (Phthorimaea opercu丄ella), Momon'nkui .Power, Carposina niponensis), Lingophyllum (IUiberis pruni), Blackeye moth (Latoia sinica), Ilaga (Monema flavescens), Nashila 7 (Narosoideus flavidorsalis), Aila katana (Parasa consocia), Himecrofica contracus), Chihiro suppressalis, Cnaphalocrocis medinalis, Conogethes punctiferalis, Conegethes punctiferalis 77, Diap ania indica, Ectomyelois pyrivorella, Ephestia elutella, Ephestia ella e Tumon Mataraiga (Euzophera batangensis), Glyphodes pyloalis, Hellulla undalis, Marasmia exigua, Maruca testulalis, Furatri

(Ostrmia scapulalis), Funomeiga (Ostrinia zaguliaevi), Shino-Kuttoga

(Parapediasia teterrella), turquoise (Pleuroptya ruralis), 7 (Plodia interpunctella), Sancamera 77 (Scirpophaga incertulas), Λ Papilio xuthus, Colias erate poliographus, Pieris rapae crucivora, Lampides boeticus, Angerona prunaria, Ascotis seist, B ), Cystidia couaggaria, Dendroiimus spectabilis, Malocasoma neustna testacea, Odonestis pruni japonensis Cephonodes hylas, grape sparrow (Acosmeryx castanea), crested killer whale (Clostera anachoreta), cecro killer whale (lostera anastomosis), monk killer whale (Phalera flavescens),

(Phalerodonta manleyi), killer whale (Stauropus mgi persimilis), chia doku force '(Euproctis pseudoconspersa 8 monsi mouth doku 7 (Euproctis similis dokuga (Euproctis subflava) 8 Hyphantria cunea, Spilosoma imparilis, Acanthoplusia agnata, Aedia leucomelas Agrotis ipsilon, Agrotis segetum flava (Agrotis segetum flava) Anomis mesogona, Autographa nigrisigna, Trichoplusia ni, Ohkokuga (Helicoverpa.armigera), Tanokokuga (Helicoverpa assulta), lio maritima Mamestra brassicae, Naranera aenescens, Pseudaletia sep arata, Inesou (Sesamia inferens), Spodoptera depravata (Spodoptera depravata)

(Spodoptera exigua), Spodoptera litura, Lingokenmon (Triaena intermedia Nykenmon (V minia rumicis xymonya y Xestia nigrum)), Hemiptera, etc ) _s lewisi, Togeshirahoshimushi (Eysarcoris parvus), Shirahoshi beetle (Eysarcoris ventralis), Glaucias subpunctatus, Akasun sword beetle (Graphosoma rubrolineatum), Kusa ³ r force;> ^ Nezara antennata, Nezara viridula, Tymon Mosquito Memushi (Piezodorus hybneri), Chiyanoku Neaokamemushi (Plautia stali), Inekuro force Memushi (Scotinophara lurida), Iwasaki stink bug (Starioides iwasakii), nightshade Kamemu

sordidus sword (Anacanthocoris striicornis), horned beetle (Cletus punctiger), beetle beetle (Cletus trigonus), horned beetle (Molipteryx fulginosa) To the Thai Wan Spider Leptocorisa oratorius, Riptortus clavatus, Aeschynteles maculatus, Scarlet beetle

(Liorhyssus hyalinus), squeaker moth (Cavelerius saccharivorus), giant beetle (Macropes obnubilus), hiratahi yotanagamemushi (Pachybrachius luridus), Snorkele (Dysdercus cingulatus), Scarlet beetle (Dysdercus poecilus), Kikugunbai

(Galeatus spinifrons), Yanagi Gumbai (Metasalis populi), Cuzgunbai

(Stephanitis fasciicarina), Nashigumbai (Stephanitis nashi), Sedgegumbai (Stephanitis pyrioides), Himegumbai (Uhlerites debile), Knorememi Gumbai

(Uhlerites latius), Adelphocoris lineolatus, Velphocoris triannulatus, _N polyf iucorum, Apolygus spinola, A pal. (Cyrtopeltis tennuis), Black-headed turtle (Ectometopterus micantulus), Black-headed turtle (Halticiellus insularis) (Heterocordylus flavipes); ) Mukikasumikame (Stenodema calcaratum), Futasushikasu turtle (Stenotus binotatus), Akasushikasu ^ turtle (Stenotus rubrovittatus) _N Usumon Mi Dorikasumikame (Taylorilygus pallidulus), Akahigehosomi Dorikasumikame (Trigonotylus coelestialium), etc., the same Orthoptera (Homoptera) Abrazemi

(GraotoDsaltria nigrofuscata), Maeki ヮ fuki (Aphrophora costalis), Maza ヮ fuki (Aphrophora flavipes), Grafia fuki (Aphrophora vitis), Himefta tena (Clovia punctata), Ps. ) 、 Cofana spectra 、 Aguriahana quercus 、 Alnetoidia alneti 、 Akiliona ferruginea 、 Apiona , Midori Himeokono-kui (Edwardsiana flavescens), Nokurahimeyo Kono-kui (Edwardsiaha rosae), Matsuhimeyo Kono-kui

(Empoasca abietis), Chiyanomi Dori Himekonokui (Empoasca onukii), Inekii Himekobi (Thaia subrufa), Zi ginella citri, Phutaten 3 nokui (Macrosteles fascifrons) Nephotettix cincticeps), Nephotettix nigropictus, Nephotettix virescens orientus ishidai, Recilia dorsalis, Sorhoan tritic, Sorhoan tri Sneusotettix subfusculus Laodelphax striatellus _N Toi Lounka (Nilaparvata lugens), Satono Usuironuka (Numata muiri), Toro Sokosiki (Peregrinus maidis), Kurofutsunounka (Perkinsiella)

saccharicida), white-spotted planthopper (Sogatella furcifera), hyunka (Sogatella panicicola), black-headed lice (Anomoneura mori), black-headed squirrels (Calophya nigridorsalis), red-headed lice (Diaphorina citri)

(Mesohomotoma camphorae)> Psylla abieti, Nounnonrami

Psylla alni, Psylla jamatonica, Psylla mali, Psylla malivorella, Psylla pyrisuga, Psylla tobirae Litho Gall lice (Trioza quercicola), Mikantogukuna lice (Aleurocanthus spiniferus), Grape white lice (Aleurolobus taonabae), Dandelion coconut lice (Bemisia tabaci), Cigarette lice (Dialeurodes citri), Onrum valenium des Reef Konasif (Bemisia argentifolii), Grape Aphid (Viteus vitifolii), Lingone Aphid (Aphidounguis mali), Apple Root Beetle (Eriosoma lanigerum), Sugarcane Root Beetle (Geoica lucifuga), Endohige pi (Aphis citricola Aphis craccivora, Janagiab, Aphis farinose yanagicola, Aphis gossypii, Shagaimohikenaka, Aulacorthum solani, Brachycaude brich , Chulip diaphragmphid (Dysaphis tulipae), cynomolgus toafkin arab, aphid (Euceraphis punctipennis), peach beetle (Hyalopterus pruni), narcissus aphid (Lipaphis erysimi), kakuhimehi Aphids (Macrosiphoniella sanborni), Zurip genus / "Frams (Macrosiphum euphorbiae), Sola bean aphid (Megoura crassicauda), Nasikova aphid

(Melanaphis siphonella), My zus malisuctus, Myzus mumecola, Myzus persicae, Neotoxoptera formosana, Orimus len Rhualosiphum nymphaeae, Rhualosiphum padi (Rhopalosiphum padi)

rufiabdominalis), Nasimanolea beetle (Sappaphis piri)

(Schizaphis piricola), wheat beetle aphid (Sitobion akebiae), wild boar bean aphid (Sitobion ibarae), citrus aphid (Toxoptera aurantii), citrus aphid (Toxoptera citricidus), peach beetle (Tmonro aus) Uroleucon formosanum ヽ Barbet aphid (Schizaphis graminum), Drosicha corpulenta, Icerya purchasi, Matsumotoi criscus, oc Scale insects (Dysmicoccus wistariae) (Planococcus citri); riferus), Noreby weevil (Ceroplastes rubens), Citrus discrepans, Coccus hesperidum, Coccus pseudomagnoliarum, Scallop (Ericerus pela) Lecanium corni), Chiyanoka scale insect (Lecanium persicae), mandarin orange sword beetle (Pulvinaria aurantii), mandarin orange crow (Pulvinaria citricola), cola quatia (Pulvinaria kuwaole) Aonidiella aurantii, Aonidiella citrina, Aspidiotus destructor, Aspidiotus hederae, Akahosh marsh moth Scale insects (

Comstockaspis perniciosa), Duplaspidiotus claviger, Lepidosaphes beckii, Lepidosaphes ulmi, Nashironakafu- / Z J humushi (apopulucaspis) Hawkworm (Parlatoreopsis pyri), camellia Hawkworm (Parlatoria camelliae), chinosa black-headed bug (Parlatoria theae), stag beetle (Parlatoria ziziphi, 7 Aphids (Pseudaonidia paeoniae), Pseudaulacaspis pentagona), Pseudaulacaspis prunicola, Unaspis yanonensis etc. , Eucetonia pilifera (Eucetonia roelofsi), Heptophylla picea, Kofukikogane

(Melolontha japonica), Scarab beetle (Mimela splendens), Coreono, Oxycetonia jucunda, Japanese beetle (Popillia japonica), Japanese beetle (Anthrenus verbasci), Japanese beetle (Attagenus unicolor jas) (Lasioderma serricorne), Hyctus brunneus, Carpophilus dimidiatus, Carpophilus hemipterus, Ponach "Epilachna vigmtioctomaculata, Tentou (Epilachna varivestis), Japanese sword beetle (Alphitobius laevigatus), Nongus pipe (Neatus picipes), Japanese red-spotted toad (Palorus ratzeburgii)

(Tenebrio molitor), Tribolium castaneum, Tribolium confusum, Epicauta gorhami, Aeolesthes chrysothrix, mai Long-horned beetle (Monochamus alternatus), Long-horned beetle (Psacothea hilaris), Grape, Long-horned beetle (Xylotrechus pyrrhoderus), White-eye Beetle

(Xystrocera globosa), Λ Root beetle (Acanthoscelides obtectus), / Callosobruchus chinensis, Callosobruchus maculatus, Urino, Aulacophora femoralis, Tyba sano Glutida (Gassida nebulosa), "7" Nasa Tohi, Nohemun (Hetocnema concinna), Imaspanorenurimu (Colasposoma dauricum), Diyuushi Hoshikubana-no-Mushi (Crioceris quatuoraecimpunctata), D Mussels (Linaeidea aenea, Kisino-Luperomorpha tunebrosa), Medythia nigrobilineata, Oulema oryzae, Himekinoku Nesano-no-Mushi (Pagria signata) Wild boar, worm (Phyllotreta striolata), colorado moth

Leptinotarsa decemlineata) Corn nolate worms. (Diabrotica sp.) Involvulus cupreus, Rhynchites heros), Cylas formicarius, apple beetle

(Anthonomus pomorum Eight Daikonsa / Rezomushi (Ceuthorhynchidius

albosuturalis), Curculio sikkimensis, stubble

(Echinocnemus squameus), Ezocepes postfasciatus, Hypera nigrirostris, Hypera postica, Lissorhoptrus orresophile zolist Paramecium (Phyllobius armatus), Chibikofukizomuushi (Sitona japonicus), ヮ Tami nozomuushi (Anthonomus grandis), Coconut beetle (Sitophilus oryzae), Kokuzoumushi (Sitophilus zeamais) , THYSANOPTERA, Asaphothrips obscurus, Chirothrips manicatus, Dendrothrips minowai, F. Frankliniella lilivora, black Nine thrips (Heliothrips haemorrhoidalis), Cosmos thrips (Microcephalothrips abdominalis), Mycterot'hrips glycines (Pseudodendrothrips mori), Cynthia thrips , 不アサ S (Stenchaetothrips bifornus), ィ, ザキザ (Thrips alliorum), ヮnigropilosus), Thrips palmi, Thrips palmos, Franklinella occidentalis, Thrips setosus, Thrips simplex, Thrips tabaci Inopudaazamuma (Haplothrips aculeatus), Sinakuda Haplothrips chinensis, Haplothrips kurdjumovi, Haplothrips niger, Shionaga Kudaazamuma

(Leeuwenia pasanii), task dazamuma (Liothrips floridensis), urinuta kazamuma (Liothrips vaneeckei), shimanorekkusamuma (Litotetothrips pasaniae), force chrysanthemum (Ponticulothrips diospyros)

As (ORTHOPTERA), the cockroach (Periplaneta americana), the cockroach (Periplaneta fuliginosa), the cockroach (Periplaneta japonica), the Blattella germanica, Mesamaki (Homorocoryphus jezoensis), Hemocory (Homorocoryphus lineosus), Kera (Gryllotalpa sp.), Coago (Oxya hyla intricata), Oxya. Yezoensis, Tonosama mikutoria (Locusta migratoria)

Diptera includes the following species: Tipula aino, Bradysia agrestis, Asphondylia sp. Dacus cucurbitae, Micus dorsalis), Dacus tsuneonis, Ohtono, Madaraminokue (Rhacochlaena japonica), Hydrellia griseola ゝ Hydrellia sasakii, Oh Toshou Drosophila suzukii, Chlorops oryzae, Meromyza nigriventris, Agromyza oryzae)

(Chromatomyia horticola), Lars /, Mokuri Nokue (Liriomyza bryoniae), Nino, Mokuri Nokue (Liriomvza chinensis), Mameno Mokuri Mokuno (Liriomyza trifoiuno, Tomato no Momo (Liriomyza sativae) (Musca domestica), Culex pipiens pallens, Shinano, Magura (Anopheles sinensis), Aedes albopictus, Chilex-pipiens molestus, etc., HYMENOPTERA Two-handed Brab wasp (Athalia japonica) ^ Cuff ,, Rano ヽ nochi, Athalia rosae ruiicornis), Zincono ヽ nochi (Arge mali), Churenshino ヽ nochichi (Arge pagana) us kuriphilus, such as Formica japonica, Ascarid (ACARINA) ), Muda 'Penthaleus major, Bredopalpus lewisi, Brevipalpus obovatus, Ninappnorehimeno

(Dolichotetranychus floridanus), Tenkipalpus zhizhiiasnvniae, Minamihimenotata, Brevipalpus phoenicis, uckerella pavoniformis, Kyoichi Ichipra Nisokuchi-no-Kuno-no-Tatsuri (Bryobia rubrioculus), Ansno-no-Gugu (Eotetranychus geniculatus), Kino-Nota-Gino, Two (Eotetranychus pruni) Eotetranychus sexmanaculatus, Eotetranychus smithi, Eotetranychus uncatus, Oligonychus hondoensis , Oligonychus ticis, Oligonychus karamatus, Panonychus citri, Panonychus ulmi, Tetranychus cinnabariny , Namino ヽ ta, 'Two (Tetranychus urticae, Outu-no-Tota-(Tetranychus viennensis), Teyano-nagasabida- (Acaphylla theae), Tulip-sabi tick (Aceria tulipae), Mikansabidai (Aculops pelekassi), Mosa fockeui), Lingosabida ii (Aculus schlechtendali), Chiasano sabidaji (Calacarus carinatus)

(Aleuroglyphus ovatus), Robinhigni (Rhizoglyphus robini), Tyrophagus putrescentiae, Ornithonyssus bacoti, Akats; Y :

Bentgrass centu as TYLENCHIDA

(Anguina agrostis), Anguina tritici, Ditylenchus destructor no, Tylenchorhynchus claytoni, Tylenchorhynchus claytoni, n , Imamanemo Grisenchu

(Hirschmanniella imamuri), Nemoku Lisenchu (turschmanruella oryzae ノ, Southern Nemusaresentyuyu (Pratylenchus coffeae), Suzuran Negusasencentu (Pratylenchus convallariae), ■ loosi, Pseylenchus neglectus, Pratylenchus penetrans, Pratylenchus sp., Helicotylenchus dihystera, Helicothylrina Yuli (Helicotylenchus sp.), Holylaimus (Hoplolaimus sp.), Nisefukuguchi Senchu (Rotylenchulus reniformis)

(Scutellonema brachyurum), Bidera avenae, Cactodera cacti, Cryphodera sp., Globodera rostochiensis, Inesis

(Heterodera elachista), Gussis Tosenchu (Heterodera erlycines), Clover cistocentiyu (Heterodera trifolii), Alena ria (Meloidogyne arenaria), Tsuno Kinekop 'Sentiyu (Meloidogyne camelliae), Shinobu Nekobusenchu (Meloidogyne graminis), Tanekpusenteyu

(Meloidogyne hapla) Samomai Nekobu Sentiyu (Meloidogyne incognita), Nekobusenchu (Meloidogyne sp.), Mikannesenchu (Tylenchulus)

semipenetrans), Aphelenchus avenae, etc., as DORYLAIMIDA, Longidorus martini, Longidorus sp., American lily americanum X , Oono, licenteyu (Xiphinema sp. Trichodorus sp.), Etc., as THYSANURA,

(Ctenolepisma villosa), Sea lion ^ (Lepisma saccharina), Mata, Fushi ^

(Thermobia domestica), etc., Termites (ISOPTERA), Diptero termites (Crvptotermes domesticus VIII Coptotermes iormosanus), Sharon ants (Reticulitermes speratus), Taiwan termites (Odontoter es formosanus) OPT, OC PS Hiratachiyate (Liposcelis bostrychophilus), flea eyes (SIPHONAPTERA),

(Ctenocephalides canis), lice (ANOPLURA), head lice (Pediculus humanus humanus), arthropod labrum (CHILOPODA), geji (Thereuronema tuberculata), etc., arthropod double leg (DIPLOPODA) Examples of molluscs (MOLLUSCA) such as oyster (Oxidus gracilis) include slugs (Incilaria bilineata).

· The pest control composition of the present invention is used as it is to control various pests, or is diluted appropriately with water or suspended or suspended in an amount effective for pest control. It can be used for plants that are expected to occur.For example, in addition to spraying pests on pests that occur in fruit trees, cereals, vegetables, etc., soaking seeds in chemicals, seed dressing, Seed treatment such as calper treatment, soil all-layer treatment, crop application, floor soil mixing, cell seedling treatment, planting hole treatment, plant root treatment, top dressing, rice box treatment, water surface treatment, etc. And can be absorbed from the roots. In addition, it can also be applied to nutrient solution in nutrient solution (hydroponic) cultivation, smoke, or trunk injection. Furthermore, for example, in addition to spraying on storage insects, house pests, sanitary pests, forest pests, etc., it can also be used for application to house building materials, smoke, baits and the like.

The pest control composition of the present invention is generally used in a form convenient for use in accordance with a conventional formulation method for agricultural and horticultural drugs. That is, these Is mixed with an appropriate inert carrier or an auxiliary agent that imparts a desired function if necessary, and dissolved, separated, suspended, mixed, impregnated, adsorbed or adhered, as appropriate. What is necessary is just to formulate and use for a dosage form, for example, a suspension agent, an emulsion, a liquid agent, a wettable powder, a granule, a powder agent, a tablet.

The inert carrier that can be used in the present invention may be either solid or liquid. Examples of materials that can be used as a solid inert carrier include soybean flour, cereal flour, wood flour, bark flour, saw flour, Tobacco stem powder, tarmi shell powder, bran, fiber powder, residues after extraction of plant extracts, synthetic polymers such as ground synthetic resin, clays (for example, kaolin, bentonian straw, acidic clay), talc (for example, talc) ), Silicas (for example, diatomaceous earth, silica sand, mica, white carbon (hydrous finely divided silicon, hydrous silicic acid is a synthetic highly dispersed silicic acid, and some products contain calcium silicate as the main component)), activated carbon Inorganic minerals such as powder, pumice, calcined diatomaceous earth, ground brick, fly ash, sand, calcium carbonate, calcium phosphate End, ammonium sulfate, ammonium phosphate, nitric weaker, urea, can be exemplified chemical fertilizers such as salts depreciation, compost and the like, they alone if Ku is used in the form of mixtures of two or more.

The material which can be a liquid inert carrier is selected from those having solvent ability itself and those which can disperse the active ingredient compound with the aid of an auxiliary agent without having solvent ability. As examples, the following carriers can be exemplified, but these are used alone or in the form of a mixture of two or more, for example, water, alcohols (for example, methanol, ethanol, isopropanol, butanol, ethylene glycol). ), Ketones (eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.), ethers (eg, jetinoleether, dioxane, cellosolve, diisopropyl ether, tetrahydrofuran, etc.), fat Group hydrocarbons (eg kerosene, mineral oil, etc.) ), Aromatic hydrocarbons (eg benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, etc.), halogenated hydrocarbons (eg dichloromethane, black mouth form, tetrachlorocarbon, black mouth benzene, etc.), esters (Eg, ethyl acetate, butyl acetate, ethyl propionate, diisobutyl phthalate, dibutyl phthalate, dioctyl phthalate, etc.), amides (eg, dimethylformamide, jetylformamide, dimethylacetamide, etc.), two And tolyls (for example, acetonitrile).

As the auxiliary agent, the following typical auxiliary agents can be exemplified, and these Adjuvants are used depending on the purpose and can be used alone, in some cases with two or more adjuncts, and in some cases, no adjuncts can be used at all.

For the purpose of emulsifying, dispersing, solubilizing and wet or wet the active ingredient compound, a surfactant is used as an auxiliary agent, for example, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxy Ethylene higher fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkyl aryl sulfonate, naphthalene sulfonate, lignin sulfonate, higher alcohol Surfactants such as oleyl sulfate can be indicated.

Further, for the purpose of stabilizing the dispersion of the active ingredient compound, sticking and Z or binding, the following auxiliary agents can be used as auxiliary agents, such as casein, gelatin, starch, methyl cellulose, carboxy Adjuvants such as methyl cellulose, arabia gum, polybutyl alcohol, pine oil, coconut oil, bentonite, xanthan gum and lignin sulfonate can be used.

In order to improve the flowability of solid products, the following adjuvants can be used as auxiliary agents, for example, auxiliary agents such as wax, stearate, alkyl phosphate ester and the like can be used. As a peptizer for suspension products, for example, auxiliary agents such as naphthalene sulfonic acid condensate and condensed phosphate can be used. As the antifoaming agent, for example, an auxiliary agent such as silicone oil can be used.

The pest control composition of the present invention is stable to light, heat, oxidation, etc., but if necessary, an antioxidant or an ultraviolet absorber such as BHT (2, 6-dibutyl butyl 4- Methylphenol), phenol derivatives such as BHA (Butylhydroxyanisole), bisphenol derivatives, phenyl naphthylamine, phenyl-β-naphthylamine, and condensates of phenetidine and acetone. Alternatively, a more stable composition can be obtained by adding an appropriate amount of a benzophenone compound as a stabilizer.

The pest control composition of the present invention can be used to control the various pests as they are, appropriately diluted with water or the like, or suspended in an amount effective for pest control. It can be used by applying it to a place where the expected crop or occurrence is not desirable. The amount used varies depending on various factors such as the purpose, target pests, crop growth status, pest generation tendency, weather, environmental conditions, dosage form, application method, application location, application timing, etc. As an active ingredient per arel .lg ~ 1 0 It may be applied by appropriately selecting from the range of 00 g, preferably in the range of 1 g to 500 g.

The pest control composition of the present invention can be mixed with plant protection agents and materials such as herbicides, fertilizers, soil conditioners, plant growth regulators, etc. to make a multipurpose composition with further excellent efficacy.

(Example)

In the following, this description will be described in more detail with reference to examples and test examples.

(Example 1)

N— [1,1-Dimethyl-2-[(4-methylbenzoyl) amino] ethyl] [(1-methylethyloxycarbonyl) amino] Acetate amide (Compound No. 14)

2- [(1-methylethyloxycarbonyl) amino] acetic acid (0.24 g, 1.49 mm o 1) in THF solution (3 m 1) 1, 1 '—Carbonylbis- 1 H— Imidazole (0.25 g, 1.54 mm o 1) was added at room temperature and stirred for 1 hour. N- (2-Amino-2-methylpropyl) 4-methylbenzoic acid amide (0.25 g, 1.2 1 mm o 1) was added to the reaction solution at room temperature, and the mixture was stirred for 12 hours at room temperature. The reaction solution was washed successively with 5% aqueous citrate solution, saturated brine, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 1) to obtain 0.29 g of the desired product as a white solid. (Yield 69%).

(Example 2)

N— [2—Methyl mono 1 _ (, S) — [[(4-Methylbenzoyl) amino] methyl] propyl] 2— (S) mono [(1,1, dimethyldimethyloxycarbonyl) amino] Manufacture of valeric acid amide (Compound No. 40)

2- (S) 1 [(1, 1-Dimethyl ヱ tyoxycarbonyl) amino] 1 in 1 mL of dichloromethane solution (50 m 1) of valeric acid (2.54 g, 1 1.69 mmol) '—Canolepo / Levis 1 H—imidazole (1.90 g, 11.72 mm o 1) was added at room temperature and stirred for 1 hour. N— [2-(S) —Amino-1-methylbutyl] 4 monomethylbenzoic acid amid hydrochloride (2.00 g, 7. 79 mm o 1), triethylamine (0.88 7) g, 8.60 mm o 1) was added at room temperature, and the mixture was stirred for 12 hours at room temperature. The reaction solution was mixed with 5% aqueous citrate solution, saturated brine, saturated bicarbonate. The extract was washed successively with an aqueous sodium solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 2.86 g of the desired product as a white solid (yield 88%).

(Example 3)

N— [2—Methyl 1 1— (S) — [[(4-Methylbenzoyl) amino] methyl] pyl] 2 — (S) 1 [(1, 1-dimethylethyloxycarbonyl) amino] 1 Production of 2-phenylacetamide (Compound No. 60)

2- (S)-[(1, 1-Dimethylethyloxycarbonyl) amino] — 2-phenylacetic acid (2.93 g, 1 1.6 6 mm o 1) solution in dichloromethane (50m To 1) was added 1,1′-carboninolebis-1-H-imidazole (1.990 g, 11.72 mm o 1) at room temperature and stirred for 1 hour. In the reaction mixture, N— [2— (S) -amino 3-methylbutyl] 4-methylbenzoic acid hydrochloride (2.00 g, 7.79 mmo 1), triethylamine (0.87 g, 8. 60 mm o 1) was added at room temperature and stirred for 12 hours at room temperature. The reaction solution was washed successively with 5% aqueous citrate solution, saturated brine, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 3.06 g of the desired product as a white solid (yield 8 7%)

(Example 4)

N— [2-Methyl-1— (S) — [[(4-Methylbenzoyl) amino] methyl] propyl] 2— (RS) — [(1,1-dimethylethyloxycarbonyl) amino] — 2— (Tetrahydrofranfuran 3-yl) Acetamide (Compound No. 6 9) Production-

2-(RS)-[(1, 1-Dimethylethyloxycarbonyl) amino] — 2— (Tetrahydrofuran-3-yl) Acetic acid (1.44 g, 5.87 7 mm o 1), N— [2— (S) —Amino—3-methylbutyl] 4 monomethylbenzoic acid amid hydrochloride (1.26 g, 4. 89 mmol), N—hydroxysuccinic acid imide (0.64 g, 6. 3 6 mm o 1), dicyclohexylcarbodiimide (1.30 g, 6. 36 mm o 1) in dichloromethane solution (50 ml) at room temperature with triethylamine (0.59 g , 5.87 7mmo 1) was added and stirred at room temperature for 5 hours. The resulting crystals of dicyclohexylurea were removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (n-xan: ethyl acetate = 1) The product was purified in 1) to obtain 1.23 g of the target product as a white solid (yield 56%). (Example 5)

N- [2-Methyl-1— (S) — [[(4-Methylbenzoyl) amino] methyl] propyl] 2— (S) One [(2-Methylpropyloxycarbonyl) amino] — 4-pentynoic acid amide (Compound No. 7 6) Production

2— (S) 1 [(2_Methylpropyloxycarbonyl) amino] 1-4 Into a solution of pentanoic acid (0.50 g, 2.30 mm o 1) in dichloromethane (1 0 ml), 1 , 1 'carbonino lebis 1 H-imidazole (0 · 41 g, 2.5 50 mm o 1) was added at room temperature and stirred for 2 hours. N- [2- (S) monoamino-3-methylbutyl] 4monomethylbenzoic acid (0.27 g, 1. l O mmol) and imidazole (0.22 g, 3.2 mm) o 1) was added and the reaction was stirred at room temperature for one day. Ethyl acetate was added to the reaction solution, which was then washed successively with 5% aqueous citrate solution, water, 2N aqueous sodium hydroxide solution and water, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 0.20 g of the desired product as a white solid (yield: 43%).

(Example 6)

N- [2 -Methyl 1 1 1 (S) _ [[(2 _Methylbenzoyl) amino] methyl] propyl] 3 -Methyl-2- (S) 1 [(1 Methylethyloxycarbonyl) amino] Butyric acid Manufacture of mid (compound number 1 4 3)

3-methyl-2- (S) 1 [(1-methylethyloxycarbonyl) amino] butyric acid (0.5 1 g, 2.49 mm o 1) in tetrahydrofuran solution (5 ml) , 1 ′ monocarbonyl bis 1 1H-imidazole (0.40 g, 2.49 mm o 1) was added, and the mixture was stirred at room temperature for 30 minutes. N_ [2-(S) monoamino-3-methylbutyl] 2-methylbenzoic acid amid hydrochloride (0.58 g, 2.27 mmo 1) and triethylamine (0.34 g, 3. 4 1 mm o 1) Tetrahydrofuran solution (10 ml) was added and stirred overnight. After concentrating the solvent under reduced pressure, the residue was dissolved in ethyl acetate (20 ml), washed successively with 5% aqueous citrate solution, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then dried over anhydrous sodium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 0.55 g of the desired product as a white solid (yield 60%).

(Example 7)

N— [2 -Methyl 1 1 1 (RS)-[[(4 Methylbenzoyl) amino] Methyl] Propyl] 3-methyl-2- (S) ― [(1-methylethyloxycarbonyl) amino] Butyric acid amide (Compound No. 1 5 1)

3-Methyl-1- (S)-[(1-Methylethyloxycarbonyl) amino] 1, 1 'in a THF solution (5 ml) of butyric acid (0.50 g, 2. 46 mm o 1) Monocarbonyl bis-1 H-imidazole (0.41 g, 2.53 mm o 1) was added at room temperature, and the mixture was stirred for 1.5 hours. N— [2- (RS) —Amino-3 _methyl butyl] 4-methylbenzoic acid amide hydrochloride (0.64 g, 2.4 9 mm o 1), triethylamine (0.29 g, 2. 87 mm o 1) was added at room temperature, and the mixture was stirred for 12 hours at room temperature. The reaction solution was washed successively with 5% aqueous citrate solution, saturated brine, 1N aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the residue obtained by concentration under reduced pressure is purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 1) to obtain 0.6 g of the desired product as a white solid. (Yield 6 2%).

(Example 8)

N- [1-(S)-[[(2 _Black Benzoyl) amino] Methyl] One 2-Methyl Propyl] 3-Methyl-2-— (S) One [(1 _Methylethyloxycarboxyl Amino] Production of butyric acid amide (Compound No. 1 96)

3—Methyl mono 2— (S) ― [(1_Methylethyloxycarbonyl) amino] in one dichloromethane solution (10 ml) of butyric acid (0.30 g, 1.58 mm o 1) 1 5. N-methylmorpholine (0.17 ml, 1.58 mm o 1) was added to C, and 2-methylolpropyloxycarbonyl chloride (0.2 2 ml, 1.73 mmol) was added at the same temperature. 1) was added. After stirring for 5 minutes, the reaction mixture was mixed with N— [2-(S) —amino-3 —methylbutyl] 2-chlorobenzoic acid amide hydrochloride (0.40 g, 1.44 mm o 1) and tritylamine ( To this was added 0.29 g, 2.88 mm o 1) dioctome solution (5 ml), stirred at the same temperature for 20 minutes, and then returned to room temperature. The reaction solution was washed successively with water, 5% aqueous citrate solution, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then dried over anhydrous sodium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 0.56 g of the desired product as a white solid (yield 91%).

(Example 9)

N- [1 1 (S) 1 [[(4—Black Benzoyl) amino] Methyl] — 2-Methyl Propyl] 3-Methyl 1 2— (S) 1 [(2-Methylpropyloxycarbonyl) Amino] Production of butyric acid amide (Compound No. 205)

N- [2— (S) —Amino-3-methylbutyl] 4 monochlorobenzoic acid amide hydrochloride (0.50 g, 1.80 mm o 1), 3-methyl mono 2-— (S) — [( 2-Methylpropyloxycarbonyl) amino] butyric acid (0.59 g, 2.70 mm o 1), N-hydroxysuccinic acid imide (0.33 g, 2.88 mmol), dicyclohexane Add triethylamine (0.27 g, 2.70 mm o 1) to a dichloromethane solution (20 ml) of xinolecarbodiimide (0.60 g, 2.88 mm o 1) at room temperature. Stir overnight. The resulting precipitate of dicyclohexylurea was filtered, and the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 1). The obtained crude product was washed with diisopropyl ether to obtain 0.36 g of the desired product as a white solid (yield 46%).

(Example 1 0)

N- [3—Methyl-2- (R) — [(4-methylbenzoyl) amino] butyl] 3 Monomethyl-1- (S)-[(2-methylpropyloxycarbonyl) amino] Butyric acid amide (compound No. 2 74)

(a) N- [3-Methyl _ 2— (R) ― [(4 Methylbenzoyl) amino] Butinole] 2— (S) —Amino-1-Methylbutyric acid amide

N- [3-Methyl-1- (R)-[(4-Methylbenzoyl) amino] butyl] 2- (S)-[(benzyloxycarbonyl) amino] — 3-methylbutyric acid amide (Compound No. 276, 0.93 g, 2.05 mmol), 10% palladium on carbon (0.14 g, 15 wt%), concentrated hydrochloric acid (3 ml) in methanol (50 ml) under a hydrogen atmosphere The mixture was stirred at 40 ° C for 5 hours. After replacing the reactor with nitrogen, the catalyst was removed by celite filtration. The residue obtained by concentrating the filtrate under reduced pressure was dissolved in 2N aqueous hydrochloric acid and washed with dichloromethane. The aqueous layer was adjusted to pH 12 using sodium hydroxide and extracted with dichloromethane. The organic layer was washed with 2N aqueous sodium hydroxide solution and then dried over anhydrous magnesium sulfate. The inorganic salt was filtered and concentrated under reduced pressure to obtain 0.67 g of the desired product as a yellow oily substance (yield 87%).

(b) N— [3-Methyl-2- (R)-[(4-methylbenzoyl) amino] butyl] 3-methyl-1- (S)-[(2-methylpropyloxycarbonyl) amino] butyric acid Manufacture of Amide (Compound No. 274)

N— [3-Methyl-1- (R)-([(4-Methylbenzoyl) amino] butyl] 2- (S) —Amino-3-methylbutyrate (0.2 7 g, 0.7 6 mm) o 1) , Triethylamine (0.09 g, 0.91 mm o 1) in a dichloromethane solution (30 ml) under ice-cooling with 2-methylpropyloxychloride (0.1

2 g, 0.84 mm o 1) was added dropwise, and the mixture was stirred at room temperature for 5 hours. The reaction solution was washed successively with 5% aqueous citric acid solution, saturated brine, 2N aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with n-hexane and diisopropyl ether to obtain 0.08 g of the desired product as a white solid (yield 25%).

(Example 1 1)

N— [3-Methyl-1- (R) — [(4-Methylbenzoyl) amino] butyl] 2– (S) — [(Benzyloxycarbonyl) amino] — 3-Methylbutyric acid amide (Compound number) 2 7 6)

(a) N- [3-Methyl-1- (R) — [(1,1-dimethylethyloxycarbonyl) amino] butyl] 2- (S)-[(benzyloxycarbonyl) amino ] —

3-Methylbutyrate production

2-(S)-[(Benzyloxycarbonyl) amino] — 3-methylbutyric acid (4.

6 6 g, 1 8.54 mmol) in a dichloromethane solution (1 00 ml), 1, 1 '-carbonylbis 1 H-imidazole (3.0 0 g, 1 8.54 mm o 1 ) Was added at room temperature and stirred for 1 hour. N— [1- (R)-(Aminomethyl) 1 -2-methylpropyl] strength rubamic acid 1,1-dimethylethyl ester (2 · 50 g, 1 2.3 6 mm o 1) was added to the reaction solution And stirred at room temperature for 5 hours. The reaction solution was washed successively with 5% aqueous citrate solution, saturated brine, 2N aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. The inorganic salt was filtered and concentrated under reduced pressure. The resulting crude product was washed with diisopropyl ether to obtain 2.5 g of the desired product as a white solid (yield 47%).

(b) N— [2- (R) —Amino-3-methylbutyl] 2— (S)-[(Benzyloxycarbonyl) amino] — Production of 3-methylbutyric acid amide

N— [3-Methyl-2- (R) — [(1,1-Dimethylethyloxycarbonyl) amino] butyl] 2- (S) ― [(Benzyloxycarbonyl) amino] 1 3— To a solution of methylbutyric acid amide (2.50 g, 5.74 mm o 1) in ethyl acetate (30 m 1), add 4 N hydrogen chloride in ethyl acetate (30 ml) at room temperature and stir for 5 hours. did. The reaction solution was extracted with water, and the aqueous layer was washed with ethyl acetate. The aqueous layer was adjusted to PH 1 2 using sodium hydroxide and extracted with dichloromethane. Organic layer with 2 N hydroxide After washing with an aqueous solution of sodium hydroxide, it was dried over anhydrous magnesium sulfate. The inorganic salt was filtered and concentrated under reduced pressure to obtain 1.83 g of the desired product as a yellow solid (yield 86%).

(c) N- [3-Methyl-2- (R)-[(4-methylbenzoyl) amino] butyl] 2- (S)-[(benzyloxycarbonyl) amino] -13-methylbutyric acid amide (compound Number 2 76)

N- [2- (R) —amino-1-methylbutyl] 2— (S) — [(benzyloxycarbonyl) amino] — 3-methylbutyric acid amide (1.80 g, 5.37 mmol), To a solution of triethylamine (0.6 1 g, 5.91 mm o 1) in dichloromethane (50 ml) under ice-cooling, 4-methylbenzoyl chloride (0.91 g, 5.91 mm o 1) was added. ) In dichloromethane (10 ml) was added dropwise. After stirring the reaction solution at room temperature for 2 hours, the reaction solution was washed with water. After drying the organic layer with saturated magnesium sulfate, inorganic salts were removed by filtration. The crude product obtained by concentrating the filtrate under reduced pressure was crystallized from n-hexane to obtain 1.16 g of the desired product as a white solid (yield 48%).

(Example 1 2)

N- [3 -Methyl 1 2-(S) 1 [(4 1 Methylbenzoyl) amino] Butyl] 2 1 (S) — [(Benzyloxycarbonyl) amino] 1 3 -Methylbutyric acid amide (Compound No. 28 1) Manufacturing

(a) N- [3-methyl-1- (S)-[(1,1, -dimethylethyloxycarboxyl) amino] ptyl] 2- (S)-[(benzyloxycarbonyl) amino] one

3.Methyl butyric acid amide production

2— (S) 1 [(Benzyloxycarbonyl) amino] — 3-methylbutyric acid (4.5 1 g, 1 7. 94 mm o 1) '—Carbonino Levis mono 1 H—imidazole (2.91 g, 17.79 mm o 1) was added at room temperature and stirred for 1 hour. In the reaction mixture, N— [1-(S) 1 (aminomethyl) 1 2 _methylpropyl] rubamic acid 1, 1-dimethylethyl ester (2.

4 2 g, 1 1.96 6 ramo 1) was added at room temperature, and the mixture was stirred at room temperature for 5 hours. The reaction solution was washed successively with 5% aqueous citrate solution, saturated brine, 2N aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. The inorganic salt was filtered and concentrated under reduced pressure. The resulting crude product was washed with diisopropyl ether to obtain 2.96 g of the desired product as a white solid (yield 57%).

(b) N— [2-(S) —Amino-3-methylbutyl] 2— (S) Ziroxycarbonyl) amino] Preparation of 3-methylbutyric acid amide

N— [3-Methyl-1- (S) ― [(1, 1-dimethylethyloxycarbonyl) amino] butyl] 2- (S) ― [(Benzyloxycarbonyl) amino] — 3 — To a solution of methylbutyric acid amide (2.73 g, 6.27 mm o 1) in ethyl acetate (30 ml), add 4 N hydrogen chloride ethyl acetate solution (30 ml) at room temperature. Stir for hours. The reaction solution was extracted with water, and the aqueous layer was washed with ethyl acetate. The aqueous layer was adjusted to pH 12 using sodium hydroxide and extracted with dichloromethane. The organic layer was washed with 2N aqueous sodium oxide solution and then dried over anhydrous magnesium sulfate. The inorganic salt was filtered and concentrated under reduced pressure to obtain 1.89 g of the desired product as a pale yellow solid (yield 90%).

(c) N— [3-Methyl-1-2- (S)-[(4-Methylbenzoyl) amino] butyl] 2- (S)-[[benzyloxycarbonyl) amino] — 3-methylbutyric acid , (Compound No. 2 8 1)

To 1,2-monocarbonylbis-1H-imidazole (1.19) in 4-dichlorobenzoic acid (1.00 g, 7. 33 mm o 1) in dichloromethane solution (50 ml). g, 7.33 mm o 1) was added at room temperature and stirred for 2 hours. N— [2— (S) -amino 3-Methylenobutyl] 2-— (S) One [(Benzyloxycarbonyl) amino] — 3-methylbutyric acid amide (1. 8 9 g, 5.64 mmol) was added, and the reaction solution was stirred at room temperature for 5 hours. The reaction solution was washed successively with 5% aqueous citrate solution, saturated brine, 2N aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 1.25 g of the desired product as a white solid (yield 44%).

(Example 1 3)

N— [2-(S) —Methyl mono 1 (S) — [[(4-Methylbenzoyl) amino] methyl] butyl] 3-methyl-2- (S) mono [(methyloxycarbonyl) amino] butyric acid Manufacture of Amide (Compound No. 3 0 6)

N— [2— (S) Monomethyl 1 1 1 (S) — [[(4-Methylbenzoyl) amino] methyl] butyl] 2— (S) —Amino-3-methylbutyric acid hydrochloride (0.5 0 g, 1. 35 mm ol) in dichloromethane (10 ml) and methyloxycarboninolecide (0.15 g, 1.59 mm o 1), triethylamine (0.36 g , 3.5 6 mm o 1) was added at room temperature, and the mixture was stirred for 12 hours at room temperature. The reaction solution was washed successively with 5% aqueous citrate solution, saturated brine, 1N aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. Filter inorganic salt and concentrate under reduced pressure The crude product thus obtained was washed with diisopropyl ether to obtain 0.35 g of the desired product as a white solid (yield 66%).

(Example 1 4)

N- [1- (S)-[[(Benzofuran-2-carbonyl) amino] methyl]-2-methylpropyl] 2- (S)-[((1, 1-dimethylethyloxycarbonyl) amino] Production of propionate amide (Compound No. 6 0 1)

2-(S) 1 [(1,1-dimethylethyloxycarbonyl) amino] propionate (0.46 g, 2.44 mm ol) in a dichloromethane solution (20 ml) 1′-Carbonino Lebis-1-H-imidazole (0.40 g, 2.44 mm o 1) was added and stirred at room temperature for 30 minutes. N— [2- (S) -Amino-3-methylbutyl] benzofuran 2-carboxylic acid amide (0.50 g, 2.0 2 mm o 1) was added to the reaction solution and stirred overnight. After concentrating the solvent under reduced pressure, the residue was dissolved in ethyl acetate (20 ml), washed successively with 5% aqueous citrate solution, saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 0.59 g of the desired product as a white solid (yield 70%).

(Example 15)

N— [1— (S) — [[((benzofuran-2-carbonyl) amino] methyl] — 2 —methylpropyl] 2 — (S) 1 [(1-methylethyloxycarbonyl) amino] propionic acid Manufacture of amide (Compound No. 5 9 9)

(a) N- [1— (S) — [[(Benzofuran-2-carbon) amino] methyl

1 — 2—Methylpropyl 2-— (S) -aminopropionate amide production

N- [1 1 (S) ― [[(Benzofuran 1 2-carbonyl) amino] methyl]

2-methylpropyl] 2- (S)-[[(1,1-dimethylethyloxycarbonyl) amino] propionic acid amide (Compound No. 1, 2, 1. 7 1 g, 4. 1 0 mm o 4) Hydrogen chloride solution in ethyl acetate (11 ml) was added to the ethyl acetate solution (5 ml) in 1) at room temperature and stirred overnight. The reaction solution was extracted with water, and the resulting aqueous layer was washed with ethyl acetate. The aqueous layer was adjusted to pH 12 using sodium hydroxide, extracted with dichloromethane, and the resulting organic layer was dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the filtrate was concentrated under reduced pressure to obtain 1.24 g of the desired product as a white solid (yield 95%)

(b) N— [1— (S)-[[(Benzofuran 2-carbonyl) amino] meth Nole] — 2-methylpropyl] 2— (S) ― [(1-methylethyloxycarbonyl 2-amino) amino] Propionic acid amide (Compound No. 5 99)

N— [1— (S) — [[(Benzofuran-2-carbonyl) amino] methyl] — 2-methylpropyl 2- (S) — aminopropionic acid amide (0.23 g, 0.7 2 mm 1-Methylethyloxycarbonyl chloride (0.10 g, 0.79 mm o 1) was added to the dichloromethane solution (5 ml) of o 1). To the reaction solution, a dichloromethane solution (1 ml) of triethylenamine (0.08 g, 0.79 mm o 1) was added dropwise, and the mixture was stirred at room temperature for 2 hours. The reaction solution was washed successively with 5% aqueous citrate solution and water, and then dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was purified by silica gel column chromatography (n-xan: ethyl acetate = 1: 1) to obtain 0.28 g of the desired product as a white solid ( (Yield 96%)

(Example 1 6)

N— [1— (S) — [[(Benzofuran-2-carbonyl) amino] methyl] — 2-monomethylpropyl] 2-— [(1,1-dimethylethyloxycarbonyl) amino] 1-2-methylpropion Production of acid amide (Compound No. 605)

2 — [(1,1-Dimethylethynoleoxycarbonyl) amino] — 2-Methylpropionic acid (2.80 g, 1 3.78 mm o 1), N— [2— (S) —Amino 1 — Methylbutyl] benzofuran 2-strong rubonic acid amide (2.26 g, 9.18 mm o 1), N-hydroxysuccinic acid imide (1.69 g, 1 4.6 9 mm o 1) ) In dichloromethane solution (50 ml), dicyclohexylcarbodiimide (DC C: 3.03 g, 14.69 mmol), triethylamine (1.39 g, 1 3.78 mmol) Was added and stirred. The produced dicyclohexylurea crystals were removed by filtration, and the filtrate was washed successively with 5% aqueous quesuccinic acid solution, saturated aqueous sodium hydrogen carbonate solution and water, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was purified by silica gel column chromatography (n-hexane: ethyl acetate = 1: 1) to obtain 3.39 g of the target product in white. Obtained as a solid (yield 86%).

(Example 1 7)

N- [2— (RS)-[[(Benzofuran-2-carbonyl) amino] 1-methyl] ethyl] [3-methyl-1-2— (S) — [N- (1, 1-dimethylethylo] Xylonyl) amino]] Butyric acid amide (Compound No. 64 9) 3-Methyl-1- (S) ― [(1, 1-Dimethylethyloxycarbonyl) amino] Butyric acid (0.5 5 g, 2.5 5 mm o 1) in dichloromethane solution (50 ml) 1, 1′-carbonylbis 1 H-imidazole (0.4 1 g, 2.5 5 mmol 1) was added and stirred at room temperature for 1 hour. N- [2- (RS) -aminopropyl] benzofuran mono-2-carboxylic acid amide hydrochloride (0.50 g, 1.96 mm o 1), imidazonole (0.44 g, 6. 4 7 mm o 1) was added and stirred at room temperature for 5 hours. The reaction solution was washed successively with 5% aqueous citrate solution, saturated brine, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with a mixed solution of diisopropyl ether and n-hexane to obtain 0.60 g of the desired product as white crystals (yield 73%).

(Example 1 8)

N— [3-Methylenole 2— (S)-[(Benzofuran-2-carbonyl) amino] Butyl] 2-— (S) One [(Benzyloxycarbonyl) amino] — 3-Methylbutyric acid amide (compound Number 6 7 5)

To a dichlorofuran solution (50 ml) of benzofuran-2-carboxylic acid (1.73 g, 1 0.6. 8 mm o 1) at room temperature, 1, 1′-carbonylbis 1 H-imidazole (1 7 6 g, 1 0. 6 8 mm o 1) was added, and the mixture was stirred at room temperature for 1 hour. N— [2— (S) —Amino-3-methylbutyl] 2— (S) One [(Benzyloxycarbonyl) amino] — 3-Methylbutyric acid amide (3.41 g, 1 0.17 mm o 1) was added, and the mixture was stirred at room temperature for 5 hours. The reaction solution was washed successively with 5% aqueous citrate solution, saturated brine, 2N aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with a mixed solution of diisopropyl ether and n-hexane to obtain 3.60 g of the target product as light yellow crystals (yield 74%) .

(Example 1 9)

N- [[2— (S) 1 [(Benzofuran 1 2-carbol) amino] — 3-methyl] butyl] [2— (S) 1 [(1-methylethyloxycarbonyl) amino] 1 3-Methyl] butyric acid amide (Compound No. 6 7 2)

(a) N- [3-Methyl-1- (S) — [(Benzofuran-2-carbonyl) amino] butyl] 2- (S) Preparation of monoamino-3-methylbutyric acid amide

N— [3-Methyl-2- (S) 1 [(Benzofuran 1 2_carbonyl) amino] Butyl] 2- (S)-[[(Benzyloxycarbonyl) amino]-3-methylbutyric acid amide (Compound No. 8 6, 3.4 0 g, 7.09 mm ol), 10% palladium on A methanol solution (50 ml) of carbon (0.5 1 g, 15 wt%) and concentrated hydrochloric acid (3 m 1) was stirred at 40 ° C. for 5 hours in a hydrogen atmosphere. After replacing the reactor with nitrogen, the catalyst was removed by celite filtration. The residue obtained by concentrating the filtrate under reduced pressure was dissolved in 2N aqueous hydrochloric acid and washed with dichloromethane. The aqueous layer was adjusted to pH 12 using sodium hydroxide and extracted with dichloromethane. The organic layer was washed with 2N aqueous sodium hydroxide solution and then dried over anhydrous magnesium sulfate. The inorganic salt was filtered and concentrated under reduced pressure to obtain 1.82 g of the desired product as a white solid (yield 74%).

(b) N- [[2— (S)-[(Benzofuran-2-carbonyl) amino] — 3

—Methyl] butyl] [2— (S)-[(1-methylethyloxycarbonyl) amino] 1-methyl-butyric acid amide (Compound No. 6 7 2)

N- [3-methyl-1- (S)-[[(benzofuran-2-carbonyl) amino] butyl] 2- (S) -amino-3-methylbutyric acid (0.80 g, 2.3) 2 mm o 1), triethreolamine (0.26 g, 2.5 5 mm ol) in diclonal methane solution (50 ml), 1_methylethyloxycarboxyl chloride (0 3 1 g, 2.5 5 mm o 1) was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. The reaction solution was washed successively with 5% aqueous citrate solution, saturated brine, 2N aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 0.58 g of the desired product as white crystals (yield: 58%).

(Example 2 0)

N— [1 — (S)-[[(Quinolin_ 2-carbonyl) amino] Methyl] — 2— (S) -Methylbutyl] 2 — (S) — (Methyloxycarbonylamino) — 3— Methyl Manufacture of butyric acid amide (Compound No. 6 9 5)

3-methyl-1-2-[(methyloxycarbonyl) amino] butyric acid (0.30 g, 1.7 1 mmol), N— [2- (S) —amino-1-methylpentyl] quinoline- 1— (3-Dimethylaminopropyl) 1-ethyl carbonate in 2-dichloromethane solution (10 ml) of 2—force rubonic acid amide (0.46 g, 1.70 mm o 1) Do hydrochloride (EDC: 0.33 g, 1.72 mm o 1) was added at room temperature, and the mixture was stirred for 5 hours and allowed to stand. The reaction solution was washed with water, and then the organic layer was dried over anhydrous sodium sulfate. After the inorganic salt is filtered off, the crude product obtained by concentration under reduced pressure is diluted with diisopropyl P-pyrue. -Washing with tella to obtain 0.51 g of the desired product as a white solid (yield 70%

) o

(Example 2 1)

N— [1— (S) 1 [[(Benzofuran 1 2-carbonyl) amino] methyl] 1 2, 2-dimethylpropyl] [3-methyl-2- (S) 1 [N— (ethyloxycarbonyl) amino]] Manufacture of butyric acid amide (Compound No. 7 1 1)

3-Methyl-2- (S)-[[(Ethyloxycarboxyl) amino] Butyric acid (0.47 g, 2.50 mmol) in dichloromethane solution (50 ml) 'One strength nolevonyl bis 1 H-imidazole (0.38 g, 2.50 mm o 1) was added and stirred at room temperature for 1 hour. Add N— [2— (S) —Amino_ 3, 3,3-dimethylmethyl] benzofuran 2-carboxylic acid amide (0.50 g, 1.92 mm o 1) to the reaction mixture. Stir at room temperature for 5 hours. The reaction solution was washed successively with 5% aqueous citrate solution, saturated Japanese salt water, 2N aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 0.74 g of the desired product as white crystals (yield 8 9

%).

(Example 2 2)

N- [2—Methyl-1 _ (S) — [[(Benzofuran-2-carbonyl) amino] methyl] propyl] [3-Methyl-2- (S) -I [N- (ethyloxycarbonyl) amino ]] Manufacture of butyric acid amide (compound no. 7 6 9)

3—Methyl— 2— (S) ― [(Ethyloxycarbonyl) amino] Butyric acid (0.40 g, 2. ll mmo l) in dichloromethane solution (50 ml) 'One strength nolevonyl bis 1 H-imidazole (0: 32 g, 1.94 mm o 1) was added and stirred at room temperature for 2 hours. To the reaction mixture, N— [2- (S) -amino-3-methylpetitanol] benzofuran-2-carboxylic acid amide (0.40 g, 1.6 2 mm o 1) was added and stirred at room temperature for 5 hours. did. The reaction solution was washed successively with 5% aqueous citrate solution, saturated brine, 2N aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 0.33 g of the desired product as white crystals (yield 49%).

(Example 2 3)

N- [2—Methyl- 1— (S) — [[(Benzofuran-2-carbonyl) amino] methyl] propyl] [3-Methyl-2- (S) 1 [N- (1-methylethyl Oxycarbonyl) amino]] Preparation of butyric acid amide (Compound No. 7 7 2)

3-methyl-1- (S) — [(1-Methylethyloxycarbonyl) amino] butyric acid (0.39 g, 1.92 mmo 1), N— [2— (S) — Amino-3-methylbutyl] benzofuran 2-carboxylic acid amide hydrochloride (0.50 g, 1.77 mm o 1), N-hydroxysuccinic acid imide (0.21 g, 2.1) 2 mm o 1), dicyclohexylcarbodiimide (0.44 g, 2. 1 2 mm o 1) in a methane solution (50 ml) of triethylamine (0.35 g, 3.5 4 mm) o 1) was added at room temperature and stirred at room temperature. The produced precipitate-hexylurea precipitate was filtered and then concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 4: 1). The obtained crude product was washed with diisopropyl ether to obtain 0.38 g of the desired product as white crystals (yield 50%)

(Example 24)

N— [1 — (S)-[[(Benzofuran-2-carbonyl) amino] methyl] — 2-methylpropyl] 3-methyl-2- (S) — [(vinyloxycarbonyl) amino] butyric acid Manufacture of mid (compound number 7 7 9)

(a) N— [1 (S)-[[(Benzofuran-2-carbonyl) amino] methyl] — 2-methylpropyl [3-methyl-2- (S) amino] Preparation of butyric acid amide

N— [1 — (S) — [[(benzofuran-2-carbonyl) amino] methyl] ―

2-methylpropyl] 3-methyl-2- (S)-[(1,1-dimethylethyloxycarbonyl) amino] butyric acid amide (19.5 3 g, 4 3.83 mmo 1) To the solution (100 ml) was added 4N hydrogen chloride Z ethyl acetate solution (1 17 ml) at room temperature and stirred overnight. The reaction solution was extracted with water, and the aqueous layer was washed with ethyl acetate. The aqueous layer was adjusted to pH 12 using sodium hydroxide, extracted with dichloromethane, and dried over anhydrous magnesium sulfate. The inorganic salt was filtered and concentrated under reduced pressure to obtain 1 2.63 g of the desired product as a white solid (yield 83%).

(b) N— [1— (S) One [[(Benzofuran-2-carbonyl) amino] Methyl]] 2-Methylpropyl] 3-Methyl-1-2- (S) — [(vinyloxycarbonyl) Amino] Production of butyric acid amide (Compound No. 7 7 9)

N— [1 — (S) 1 [[(Benzofuran 1 2-carbonyl) amino] methyl] 1 2-methylpropyl [3-methyl-2 _ (S) —amino] Butyric acid amide (0.4 Triethylamine (0.41 g, 4.0 2 mm o 1) was added to 6 g, l. To the reaction solution was added dropwise dichloromethane solution (10 ml) of bioxycarbon chloride (0.17 g, 1.6 1 mm o 1) under ice cooling and stirred at room temperature for 2 hours. . The reaction solution was washed successively with 5% aqueous citrate solution, saturated aqueous sodium hydrogen carbonate solution, and water, and then dried over anhydrous sodium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 0.46 g of the desired product as a white solid (yield 83%).

(Example 2 5)

N— [1 1 (S) — [[(Benzofuran 1 2-carbonyl) amino] methyl] — 2 —Methylpropyl] 3—Methyl-2-— (S) 1 [[((Tetrahydrofurofuran 2-methyl) oxy Carbonyl] amino] butyric acid amide (Compound No. 78-3)

N— [1 1 (S) 1 [[(Benzofuran 1 2-carbonyl) amino] methyl] ― 2-methylpropyl 3-methyl-2- (S) monoaminobutyric acid amide (0. 46 g, 1. 34 mm o 1) in dichloromethane solution (10 ml), O— [tetrahydrofuran 1 2-methyl] O— [4-nitrophenolene] carbonate (0.4 3 g, 1. 6 1 A solution of mm o 1) in dichloromethane (10 m 1) was added dropwise under ice-cooling, and the mixture was stirred at room temperature for 5 days. The reaction solution was washed successively with 5% aqueous citrate solution, saturated aqueous sodium hydrogen carbonate solution and water, and then dried over anhydrous sodium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 0.52 g of the desired product as a white solid (yield 82%).

(Example 26)

N— [1— (S) — [[(Benzofuran-2-carbonyl) amino] methyl] 1-2-methylpropyl] [3-methyl-1- (S)-(ethylthiocarbonylamino)] butyric acid Manufacture of mid (compound no. 7 90)

N— [1 1 (S) — [(Benzoxazole-2-yl) carbonylaminomethyl] _ 2-methylpropyl] 3-methyl-2- (S) — aminobutyric acid amide hydrochloride (0 30 g, 0. 79 mm o 1), ethylthiocarbonyl chloride (0.10 g, 0.80 mm o 1) in dichloromethane solution (15 ml) and triethylamine (0.24). g, 2. 37 mm o 1) 5 liters of dichloromethane solution (5 ml). Added in C. Stir at room temperature for 5 hours and let stand overnight. Ethyl acetate was added to the reaction solution, washed with water, and dried over anhydrous sodium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to give 0.21 g of the desired product. Obtained as a white solid (60% yield).

(Example 27)

N- [2—Methyl- 1— (S) — [[[(1,4-Benzodioxane) 1 2— (RS) —Carbonyl] amino] Methyl] propyl] [3—Methyl 1 2— (S)-[N -(1-Methylethyloxycarbol) amino]] Preparation of butyric acid amide (Compound No. 8 9 7)

3-Methyl-1- (S) — [(1-Methylethyloxycarbonyl) amino] Butyric acid (0.37 g, 1. 8 3 mm o 1), N— [2— (S) — Amino _ 3—Methylbutyl] 1,3—Benzodioxane—2— (RS) —Strong rubonic acid hydrochloride (0.50 g, 1.66 mmol), N—Hydroxysuccinic acid (0.20) g, 1.99 mm o 1), dicyclohexylcarbodiimide (0.41 g, 1.99 mmo 1) in dichloromethane solution (50 ml) and triethylamine (0.33 g, 3. 3 2 mm o 1) was added at room temperature and stirred at room temperature. The resulting precipitate of dicyclohexylurea was filtered and then concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 4: 1). The obtained crude product was washed with diisopropyl ether to obtain 0.7 l g of the desired product as a white semi-solid (yield 95%).

(Example 28)

N— [1— (S) 1 [(Benzoxadiazole 4-yl) carbonylaminomethyl] 1 2-methylpropyl] 3-methyl 1 2-— (S) — [(1-methylethyl) Oxycarbonylamino] Butyric acid amide (Compound No. 9 2 7)

(a) Production of N— [2— (S)-(2,2-dimethylethyloxycarbonyl) amino-1-methyl] butyl phthalimide

N — [(1-Hydroxymethyl-2-methyl) propyl] Powered 1,1 —Dimethylethyl (30. 00 g, 1 4 7. 58 mm o 1), Phthalimide (2 1. 7 2 g, 1 4 7. 58 mm o 1 Triphenylphosphine (42. 36 g, 1 62.34 mm o 1) in tetrahydrofuran solution (300 ml) with azodicarboxylate jetyl (DEAD) (28. 3 2 g , 16 2.34 mm o 1) Tetrahydrofuran solution (50 ml) was added dropwise under ice-cooling, and the reaction mixture was gradually warmed and stirred at room temperature for 5 hours. Concentration gave a white solid 4 5.91 1 g The obtained white solid was purified by silica gel column chromatography to obtain the desired product 34.40 g as white crystals (yield 70%). (b) Manufacture of N- [2— (S) —amino-3-methyl] butyl phthalimide hydrochloride

Suspension of N— [2— (S)-(2,2-dimethylethyloxycarbonyl) amino-3-methyl] butyl phthalimide (2 3.05 g, 69. 34 mm o 1) in ethyl acetate To the liquid (50 ml) was added a 4 N hydrogen chloride ethyl acetate solution (150 ml, 600 mm o 1 as hydrogen chloride) at room temperature, and the mixture was stirred at room temperature for 5 hours. Precipitated white crystals were collected by filtration, and the obtained crystals were overwashed with ethyl acetate (100 ml). The obtained crystals were dried under reduced pressure to obtain 1.74 g of the objective product as white crystals.

(c) N- [2—Methyl 1 1 1 (S) — [(phthalimide 1 1 —yl) Methyl

] Propyl [3-methyl-2- (S)-[N- (1-methylethyloxycarbonyl) amino]] Preparation of butyric acid amide

3-Methyl-1-2- (S)-[(1-Methylethyloxycarbonyl) amino] butyric acid (1 7. 06 g, 8 3. 95 mmol) in dichloromethane solution (350 ml) 1, 1 'monocarbonylbis 1 H-imidazole (11.6 2 g, 8 3.95 mm o 1) was added at room temperature, and the mixture was stirred at room temperature for 2 hours. N_ [2-(S) —Amino-3-methyl] butyl phthalimide hydrochloride (15. 00 g, 64. 5 8 mm o 1), imidazonole (1 4.4 2 2 g, 2 1 3.1 1 mm o 1) was added, and the mixture was stirred at room temperature for 7 hours. The reaction solution was washed with 5% aqueous citrate solution, water and saturated aqueous sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate. After filtering the inorganic salt, the white crystals obtained by concentration under reduced pressure were washed with diisopropyl ether to obtain 18.667 g of the desired product as white crystals (yield 69%, melting point 240.9 ° C). ).

(d) N— [1— (S) — Aminomethyl 2-methylpropyl] 3-methyl — 2— (S)-[(1-methylethyl) oxycarbonylamino] Preparation of butyric acid amide

N- [2—Methyl-1 1- (S) _ [(phthalimide 1 1-yl) methyl] propyl [3-methyl-2- (S) 1 [N— (1-methylethyloxycarbonyl ) Amino]] Butylamide (10.00 g, 23. 95 mm o 1) in ethanol solution (250 m 1) at room temperature with hydrazine monohydrate (2.52 g, 50. 30 mm o 1) was added, and the mixture was stirred for 5 hours under heating to reflux. The reaction solution was returned to room temperature, and the precipitated crystals were removed by filtration and washed with ethanol. The residue obtained by concentrating the filtrate washing under reduced pressure was dissolved in dichloromethane and washed with 2N aqueous sodium hydroxide. Insoluble The white precipitate was removed by celite filtration. Extraction was performed with a 5% aqueous citrate solution, and the extract was washed with dichloromethane. Under ice-cooling, the aqueous layer was adjusted to pH 2 or higher with 2N aqueous sodium hydroxide solution and extracted with dichloromethane. The organic layer was washed with 2N aqueous sodium hydroxide solution and dried over anhydrous magnesium sulfate. The inorganic salt was filtered and concentrated under reduced pressure to obtain 5.88 g of the desired product as white crystals (yield 85%, melting point 106. 3 ° C).

(e) N- [1— (S) One [(Benzoxadiazol-4-yl) Carbonyl aminomethyl] One 2-methylpropyl] 3 _Methyl _ 2— (S) One [(1-Meth N- [1— (S) —Aminomethyl-2-methylpropinole] 3-methyl-1- (S)-[(1-methylethyl)]. Preparation of butyric acid amide (Compound No. 9 2 7) ) Oxycarbonylamino] Butyric acid amide (0.50 g, 1.99 mm o 1), Triethylamine (0.26 g, 2.5 7 mmo l) in dichloromethane (10 ml) A diclonal methane solution (10 ml) of xadiazol-41-carbohydrate (0.37 g, 2.03 mm o 1) was added at 5 ° C. After returning to room temperature, the mixture was stirred for 5 hours and allowed to stand. Ethyl acetate was added to the reaction solution, washed with water and then dried over anhydrous sodium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with disopropyl ether to obtain 0.60 g of the desired product as a white solid (yield 88%).

(Example 29)

N— [1— (S) — [[(6—Chronopyridine 1-carbonyl) amino] Methyl] — 2-Methylpropinole] 3-Methyl-1-2- (S) — [(1-Methylethyloxycarbonyl) amino ] Production of butyric acid amide (Compound No. 9 5 1)

3-methyl-1- (S)-[(1-methylethyloxycarbonyl) amino] butyric acid (0.20 g, 0.99 mm o 1) in dichloromethane solution (5 m 1) 1'-force nolevonyl bis 1H-imidazole (0.16 g, 0.99 mm o 1) was added and stirred at room temperature for 30 minutes. Add N— [2- (S) -Amino-1-methylbutyl] 6-chloropyridine pyridine-2-strong rubonic acid amide (0.20 g, 0.83 mmo 1) to the reaction mixture and stir overnight. did. After concentrating the solvent under reduced pressure, the residue was dissolved in ethyl acetate (20 ml), washed successively with 5% aqueous citrate solution, saturated aqueous sodium hydrogen carbonate solution, water, and saturated Japanese brine, and then dried over anhydrous sodium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 0.20 g of the desired product as a white solid (yield 56%). (Example 30)

N— [1-(S)-[[(Theophene-2-carbonyl) amino] methyl] 1-2-methylpropyl] 3-methyl to 2- (S)-[(2-methylpropyloxycarbonyl) amino ] Production of butyric acid amide (Compound No. 1 0 1 8)

3-Methyl-2- (S)-[(2-Methylpropyloxycarbonyl) amino] Butyric acid (0.5 2 g, 2. 42 mm o 1) in dichloromethane solution (10 ml) At 1 5 ^^ — methylmorpholine (0.27 ml, 2.42 mm o 1) was added. 2-Methylpropyloxycarbonyl chloride (0.33 ml, 2.58 mm o 1) was added dropwise, and the mixture was stirred at 115 ° C. for 5 minutes. N- [2- (S) Monoamino 3-methylbutyl] thiophene 2-carboxamide hydrochloride (0.40 g, 1.6 1 mm o 1) and triethylamine (0.33 g, 3. 22 mm o 1) in dichloromethane (5 ml) was added at 115 ° C. and stirred for 20 minutes. After the reaction solution was concentrated under reduced pressure, the residue was dissolved in ethyl acetate (20 ml), washed successively with water, 5% aqueous citrate solution, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then dried over anhydrous sodium sulfate. . After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was washed with diisopropyl ether to obtain 0.54 g of the desired product as a white solid (yield 82%). It shows as a reference example.

[Reference Example 1]

N— [1— (S) — (Aminomethyl) 1-2 methylpropyl] Preparation of 1,3-dimethylethyl ester of rubamic acid

Tetrahydrofuran solution of N- [1-(S)-(Hydroxymethyl) 1-2-Methylpropyl] Powered Lubamic acid 1,1-Dimethylethyl ester (25. 00 g, 1 2 2. 98 mm o 1) (250 m 1) 'and phthalimide (1 8. 10 g, 1 2 3. 02 mm o 1), triphenylphosphine (3 5.50 g, 1 3 5. 35 mm o 1) After stirring under ice-cooling, a tetrahydrofuran solution (10 ml) of azodicarboxylic acid jetyl ester (23.60 g, 1 3 5.5 1 mm o 1) was added dropwise for 1 hour under ice-cooling. Stir at room temperature for 4 hours. The solvent was concentrated under reduced pressure and dried. The obtained N— [2— (S)-[[(1,1, -dimethylethyloxycarbonyl) amino] — 3-methylbutyl] phthalimide was added to a white solid with ethanol (500 m 1), hydrazine 1 Hydrate (13.1 g, 26 1.69 mm o 1) was added, and the mixture was refluxed at 100 ° C. for 2 hours. The precipitated white crystals of phthaloyl hydrazide are removed by filtration, and the reaction solution is dissolved. The liquid was allowed to stand overnight, and the precipitated phthaloyl hydrazide was removed by filtration. The solvent was concentrated under reduced pressure and dried. Dichloromethane (500 ml) was added to the residue, washed with 2N aqueous sodium oxide solution (500 ml), the organic layer was extracted with 5% aqueous citrate solution (500 ml), and the aqueous layer was then washed with dichloromethane ( 500 ml). The aqueous layer was adjusted to pH 12 using sodium hydroxide (10.40 g), extracted with dichloromethane (500 ml), and 2 N aqueous sodium hydroxide solution (500 ml). After washing with, it was dried over anhydrous sodium sulfate. The inorganic salt was filtered and then concentrated under reduced pressure to obtain the target product 2.1.95 g as a white solid (yield 88%).

[Reference Example 2]

N- [3-Methyl-2- (S)-[[(1,1-dimethylethyloxycarbonyl) amino] ptyl] 4 Preparation of Cyananobenzoic acid amide

N- [1 (S)-(Aminomethyl) 1-2-methylpropyl] Forced rubamic acid 1,1-dimethylethyl ester (2.00 g, 9.89 mm o 1) in dichloromethane (20m l) was added to triethylamine (2.00 g, 2.76 ml) and ice-cooled to 0 ° C. A dichloromethane solution (20 ml) of 4_cianobenzoyl chloride (2.59 g, 14.84 4 mm o 1) was added dropwise to the reaction solution, and the mixture was allowed to return to room temperature and stirred for 2 hours. The reaction solution was washed successively with water, 5% aqueous citrate solution, and saturated aqueous sodium hydrogen carbonate solution, and then dried over anhydrous sodium sulfate. After filtering the inorganic salt, the crude product obtained by concentration under reduced pressure was recrystallized using n-hexane and ethyl acetate to give 3.05 g of the desired product as a white solid (yield: 93% ).

[Reference Example 3]

N— [2 _ (S) — Amino-3-methylbutyl] 4-Cyanobenzoic acid amid hydrochloride

N- [2— (S)-[[(1,1-Dimethylethyloxycarboxyl) amino] — 3-methylbutyl] 4-cyananobenzoic acid amide (2.85 g, 8.60 mm) o 1) was dissolved in ethyl acetate (10 ml), 4N hydrogen chloride ethyl acetate solution (13 ml) was added, and the mixture was stirred overnight at room temperature. The precipitated salt was washed with ethyl acetate and collected by filtration and dried to obtain 2.03 g of the desired product as a white solid (yield 88%).

[Reference Example 4]

N- [3-Methyl-2- (S)-[(1,1-dimethylethyloxycarbonyl) amino] butyl] Preparation of benzofurancarboxylic acid amide

Dichroic mouth of benzofuran 2-carboxylic acid (15.0 g, 92.5mmol) To a methane solution (300 ml), .1, 1 ′ monocarbonyl bis 1 H-imidazole (15.8 g, 97.6 mm o 1) was added at room temperature and stirred for 2 hours. N- [1- (S)-(Aminomethyl) 1-2-methylpropyl] -force rubamic acid .1,1-dimethylethyl ester (19.7 g, 92.5 mmol) was added to the above reaction solution. In addition, it was left overnight after stirring for 5 hours. The reaction mixture was washed successively with 5% aqueous citrate solution, water, saturated aqueous sodium hydrogen carbonate solution and water, and the organic layer was dried over anhydrous sodium sulfate. After the inorganic salt was filtered off, the crude product obtained by concentration under reduced pressure was recrystallized using disopropyl ether to obtain 26.9 g of the desired product as a white solid (yield 84%).

[Reference Example 5]

N- [3-Methyl _ 2— (S) Monoaminobutyl] Benzofurancarboxylic acid amide hydrochloride

N— [3-Methyl-1- (S)-[[(1,1-dimethylethynoleoxycarbonyl) amino] butyl] benzofurancarboxylic acid amid (28.2 g, 7 7.5 mmo 1 ) Was dissolved in ethyl acetate (50 ml), 4N hydrogen chloride ethyl acetate solution (200 ml) was added, and the mixture was stirred at room temperature for 6 hours. The precipitated salt was washed with ethyl acetate, collected by filtration, and dried to obtain 20.8 g of the desired product as a white solid (yield 95%).

The compounds represented by the formula (1) that can be produced in the same manner as those described above including the compounds of Examples 1 to 30 are shown in Table 1 as compounds 1 to 1 1 5 6. Table 2 shows some of the physical properties. In Table 1, Me is a methyl group, Et is an ethyl group, nPr is a normalpropyl group, iPr is an isopropyl group, and nBu is a noremanolebutinore group. , I B u is an isobutynol group, s B u is a secondary butyl group, t B u is a tertiary butyl group, neo Pen is a 2,2-dimethylol propyl group, and 2-E t Hex is 2 —Ethylhexyl group, MO E represents a methoxetyl group, cP r—CH 2 represents a cyclopropylmethyl group, c H ex—CH 2 represents a cyclohexylmethyl group, and CF 3 represents trifluoromethyl. CF 3 CH 2 is 2, 2, 2-trifluoroethyl group, C 1 CH 2 is chloromethyl group, CH 3 CHC 1 is chloroethyl group, CC 1 3 CH 2 is 2, 2, 2— Trichloroethyl group, 'CC 1 3 C (Me) 2 is 2, 2, 2— Trichloro 1, 1-dimethyl ethynole group, 2— Boc AE is 2— (N— Tasari -Butyloxycarbonyl) aminoethyl group, POC E t is 1_ (isopropoxycarbonyl) ethyl group, 1 — Me e — 1— Me S—E t is 1-methyl-1-methylthioethyl group , Ph is a phenyl group, 4-Me Ph is a 4-methylphenyl group, Bn is a benzyl group , O; _M e— B n is a single methinolevendinore group, 1—NP is a 1 naphthinore group, 2—NP is a 2-naphthyl group, cP en is a cyclopentyl group, c He x is Hexyl group, A c is acetyl group, B z is benzoyl group, Viny 1 is ethenyl group, a 1 1 y 1 is 2-propenyl group, propargyl is 2-probel 2-THF is the tetrahydrofuran-2-yl group, 3-THF is the tetrahydrofuran-1-yl group, THF-2-CH2 is the tetrahydrofuran-2-ylmethyl group, THF- 3—CH 2 represents tetrahydrofuran-1-ylmethyl group, 2-TP represents thiophene-2-yl group, 4-Py represents pyridine-4-yl group, and Pyr—2-CH2 represents Pyrrolidine 1-ylmethyl group, B oc— P yr — 2— CH 2 is (N-tertiary butyloxycarbonylpyrrolidine) — 2— Inolemethyl group, (1) Ment is (1 R, 2 S, 5 R) — 2-Isopropyl-5-methinoresic mouth hexane 1-11 group, (+) Ment is (IS, 2 R, 5 S) 1-Isopropyl-1-5-methyl hexane 1-yl group, 3-furanyl — CH2 is (furan 3-yl) methyl group, 4, 5-DE P— 2—CH 2 is ( 4,5-Diethoxypyrimidine 1-yl) It shall represent a methyl group.

The diamine derivative represented by the formula (1) may have an asymmetric carbon depending on the type of the substituent, and may exist as an optical isomer, a diastereoisomer, a racemate, and a mixture of any ratio.

[Table 1-1 1]

[Table 2]

Table 1.Compounds of formula (1) (2)

Compound

R1 A R2 R3 4 R5 R6 R7 R8 R9 R10 Q

15 iBu 0 H H H H Me Me H H H

16 tBu 0 H H H H Me Me H H H

17 Et 0 H Me H H H iPr H H H

18 iPr 0 H Me H H H iPr H H H

19 iBu 0 H Me H H H iPr H H H ~

20 tBu 0 H Me H H H iPr H H H

21 Et 0 H Me Me H H iPr H H H

22 iPr 0 H Me Me H H iPr H H H

23 iBu 0 H Me Me H H iPr H H H

24 tBu 0 H Me Me H H iPr H H H

25 Et 0 H Me Me H Me Me H H H

26 iPr 0 H Me Me H Me Me H H H

27 iBu 0 H Me Me H Me Me H H H

28 tBu 0 H Me Me H Me Me H H H

CF3, H

29 Et 0 H H H iPr H H H

(Racemic)

CF3. H

30 iPr 0 H H H iPr H H H

(Racemic) [Table 1-3]

Table 1 Compounds of Formula (1) (3) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 10 Q number

CF3, H

31 iBu 0 H H H iPr H H H

(Racemic)

CF3, H

32 tBu 0 H H H iPr H H H

(Racemic)

33 Et 0 H Et H H H iPr H H H

34 iPr 0 H Et H H H iPr H H H

35 iBu 0 H Et H H H iPr H H H

36 tBu 0 H Et H H H iPr H H H

37 Et 0 H nPr H H H iPr H H H

38 iPr 0 H nPr H H H iPr H H H

39 iBu 0 H nPr H H H iPr H H H

40 tBu 0 H nPr H H H iPr H H H

41 Et 0 H iBu H H H iPr H H H

42 iPr 0 H iBu H H H iPr H H H

43 iBu 0 H iBu H H H iPr H H H

44 tBu 0 H tBu H H H iPr H H H

45 Et 0 H tBu H H H iPr H H H

46 iPr 0 H tBu HHH iPr HHH- [Table 1-4] Table 1 Compounds of formula (1) (4)

[Table 1-5]

Table 1 Compounds of Formula (1) (5) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q

Number

Bn, H

63 iPr 0 H H H iPr H H H

(Racemic)

Βη, Η

64 iBu 0 H H H iPr H H H

(Racemic)

Bn, Η

65 tBu 0 H H H iPr H H H

(Racemic)

3-THF, H

66 Et 0 H H H iPr H H H

(Racemic)

3-THF, H

67 iPr 0 H H H iPr H H H

(Racemic)

3-THF, H

68 iBu 0 H H H iPr H H H

(Racemic)

3-THF, H

69 tBu 0 H H H iPr H H H

(Racemic)

70 Et 0 H allyl H H H iPr H H H

71 iPr 0 H allyl H H H iPr H H H-

72 iBu 0 H allyl H H H iPr H H H

73 tBu 0 H allyl H H H iPr H H H props

74 Et 0 H H H H iPr H H H

rgyl ~ "" ^CH3 propa

75 iPr 0 H H H H iPr H H H

rgyl

propa

76 iBu 0 H H H H iPr H H H

rgyl ~ propa

77 tBu 0 H H H H iPr H H H

rgyl-^ Q

(9) ^^) (L) ¥

[9 1 L¾]

S £ 6LU / 900Zd £ / 13d nW80 contract o / A [Table 1-7]

Table 1 Compounds of Formula (1) (7) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q number

94 Et 0 H iPr H H H H H H H

95 iPr 0 H iPr H H H H H H H

96 iBu 0 H iPr H H H H H H H → Q

97 tBu 0 H iPr H H H H H H H

98 Et 0 H iPr H iPr H H H H H

99 iPr 0 H iPr H iPr H H H H H

100 iBu 0 H iPr H iPr H H H H H

101 tBu 0 H iPr H iPr H H H H H

102 Et 0 H iPr H H Me H H H H

103 iPr 0 H iPr H H Me H H H H

104 iBu 0 H iPr H H Me H H H H

105 tBu 0 H iPr H H Me H H H H

106 Et 0 H iPr H H H Me H H H

107 iPr 0 H iPr H H H Me H H H

108 iBu 0 H iPr H H H Me H H H

109 Et 0 H iPr HHHH Me HH ~ [Table 1-8]

Table 1 Compounds of Formula (1) (8) Compounds

yr port R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q

110 iPr 0 H iPr H H H H Me H H

111 iBu 0 H iPr H H H H Me H H ~

112 tBu 0 H iPr H H H H Me Me H

CF3. H

113 Et 0 H iPr H H H H H

(Racemic)

CF3. H

114 iPr 0 H iPr H H H H H

(Racemic)

CF3, H

115 iBu 0 H iPr H H H H H

(Racemic)-^ y

CF3, H

116 tBu 0 H iPr H H H H H

(Racemic)

CF3, H

117 Et 0 H iPr H H H H H

(Racemic)

CF3. H

118 iPr 0 H iPr H H H H H

(Racemic)

CF3. H

119 iBu 0 H iPr H H H H H

(Racemic)

CF3. H

120 tBu 0 H iPr H H H H H

(Racemic) ^ D

121 Me 0 H iPr H H Me Me H H H ~

122 Et 0 H iPr H H Me Me H H H ~

123 iPr 0 H iPr H H Me Me H H H

124 allyl 0 H iPr H H Me Me H H H

125 iBu 0 H iPr HH Me Me HHH ~} r [Table 1-9]

Table 1 Compounds of Formula (1) (9)

Compound

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q

w

126 tBu 0 H iPr H H Me Me H H H

THF-2

127 0 H iPr H H Me Me H H H

-CH2

THF-3

128 0 H iPr H H Me Me H H H

-CH2 ~ ir a

129 0 H iPr H H Me Me H H H

-MeBn

130 Et 0 HH iPr H Me Me HHH ~ ~ ^CH 3

131 iPr 0 H H iPr H Me Me H H H

132 iBu 0 H H iPr H Me Me H H H

133 tBu 0 H H iPr H Me Me H. H H

134 Et 0 H iPr HHH Et HHH - ch 3

135 iPr 0 H iPr HHH Et HHH ~ " ^CH 3

136 iBu 0 H iPr H H H Et H H H

137 tBu 0 H iPr HHH Et HHH-" ^CH 3

138 Et 0 H iPr H H H iPr H H H

139 iPr 0 H iPr H H H iPr H H H

140 iBu 0 H iPr H H H iPr H H H

141 tBu 0 H iPr HHH iPr HHH [Table 1-10] Table 1 Compounds of formula (1) (10)

[Table 1 1 1 1]

Table 1 Compounds of Formula (1) (1 1) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q

¾ ·

H, iPr

153 tBu 0 H iPr H H H H H

(Racemic)

CF3C H, iPr

154 0 H iPr H H H H H

H2 (racemic)

155 Et 0 H iPr H H iPr H H H H

156 iPr 0 H iPr H H iPr H H H H

157 iBu 0 H iPr H H iPr H H H H

158 tBu 0 H iPr H H iPr H H H H

159 Me 0 H iPr H H H iPr H H H

160 Et 0 H iPr H H H iPr H H H

161 Et S H iPr H H H iPr H H H

162 vinyl 0 H iPr H H H iPr H. H H

163 nPr 0 H iPr H H H iPr H H H

164 iPr 0 H iPr H H H iPr H H H

165 iPr S H iPr H H H iPr H H H

166 allyl 0 H iPr H H H iPr H H H propar

167 0 H iPr H H H iPr H H H

gyl

168 nBu 0 H iPr HHH iPr HHH [Table 1-12]

Table 1 Compounds of Formula (1) (1 2)

^ 5:

Compound

R1 A R2 R3 4 R5 6 R7 R8 R9 R10 Q number

169 iBu 0 H iPr H H H iPr H H H

170 iBu S H iPr H H H iPr H H H

171 tBu 0 H iPr H H H iPr H H H

172 sBu 0 H iPr H H H iPr H H H

2-EtH

173 0 H iPr H H H iPr H H H

ex

Boc-P

174 yi ~ 2- 0 H iPr H H H iPr H H H

CH2

175 MOE 0 H iPr H H H iPr H H H

NeoPe

176 0 H iPr H H H iPr H H H

n

CCI3C

177 0 H iPr H H H iPr H H H

H2

CCI3C

178 0 H iPr H H H iPr H H H

(Me) 2-

Pyr-2-

179 0 H iPr H H H iPr H H H

CH2

(-) Men

180 0 H iPr H H H iPr H H H

t

181 0 H iPr H H H iPr H H H ~

182 Ph 0 H iPr H H H iPr H H H ~

4-MeP

183 0 H iPr H H H iPr H H H

h

184 Bn 0 H iPr HHH iPr HHH [Table 1-13] Table 1 Compounds of formula (1) (13)

[Table 1-14] Table 1 Compounds of formula (1) (14)

[Table 1 1 1 5]

Table 1 Compounds of Formula (1) (1 5) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q

213 iBu 0 H iPr H H H iPr H H H

^ CH ₃

214 tBu 0 H iPr H H H iPr H H H

^ CH ₃

215 Et 0 H iPr H H H iPr H H H

216 iPr 0 H iPr H H H iPr H H H

217 iBu 0 H iPr H H H iPr H H H

218 tBu 0 H iPr H H H iPr H H H

219 Et 0 H iPr H H H iPr H H H

220 iPr 0 H iPr H H H iPr H H H

221 iBu 0 H iPr H H H iPr H H H

222 tBu 0 H iPr H H H iPr H H H

223 Et 0 H iPr H H H iPr H H H

224 iPr 0 H iPr H H H iPr H H H

225 iBu 0 H iPr H H H iPr H H H

226 tBu 0 H iPr H H H iPr H H H

_ / = \ CH ₃

227 Et 0 H iPr H H H iPr H H H

O-CH ₃ [Table 1-11 16] Table 1 Compounds of formula (1) (16)

[Table 1 1 1 7]

Table 1 Compounds of Formula (1) (1 7)

Compound

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q

237 iPr 0 H iPr H H H iPr H H H

238 iBu 0 H iPr H H H iPr H H H 飞 ')

239 tBu 0 H iPr H H H iPr H H H

240 Et 0 H iPr H H H iPr H H H

241 iPr 0 H iPr H H H iPr H H H

242 iBu 0 H iPr H H H iPr H H H

243 tBu 0 H iPr H H H iPr H H H

244 Me 0 Me iPr H H H iPr H H H ~

245 Et 0 Me iPr H H H iPr H H H

246 iPr 0 Me iPr H H H iPr H H H ~

247 iBu 0 Me iPr H H H iPr H H H

248 tBu 0 Me iPr H H H iPr H H H

249 iPr 0 Ac iPr HHH iPr HHH ~ ^ [Table 1 1 1 8]

Table 1 Compounds of Formula (1) (1 8) Compounds

R1 A R2 R3 R4 R5 R6 7 R8 R9 R10 Q number

250 iBu 0 Ac iPr H H H iPr H H H

251 tBu 0 Ac iPr H H H iPr H H H

252 Et 0 Bz iPr H H H iPr H H H

253 iPr 0 Bz iPr H H H iPr H H H

254 iBu 0 Bz iPr H H H iPr H H H

255 tBu 0 Bz iPr H H H iPr H H H

256 Et 0 H H iPr H H iPr H H H

257 iPr 0 H H iPr H H iPr H H H

258 iBu 0 H H iPr H H iPr H H H

259 tBu 0 H H iPr H H iPr H H H

260 Et 0 H iPr H Me H iPr H H H

261 iPr 0 H iPr H Me H iPr H H H

262 iBu 0 H iPr H Me H iPr H H H

263 tBu 0 H iPr H Me H iPr H H H

264 Et 0 H iPr H Ac H iPr H H H

265 iPr 0 H iPr H Ac H iPr HHH [Table 1-1 19]

Table 1.Compounds of formula (1) (19)

Compound

R1 A R2 R3 R4 R5 6 R7 R8 R9 R10 Q

266 iBu 0 H iPr H Ac H iPr H H H ~

267 tBu 0 H iPr H Ac H iPr H H H

268 Et 0 H iPr H Bz H iPr H H H

269 iPr 0 H iPr H Bz H iPr H H H

270 iBu 0 H iPr H Bz H iPr H H H

271 tBu 0 H iPr H Bz H iPr H H H

272 Et 0 H iPr H H H H iPr H H

273 iPr 0 H iPr H H H H iPr H H

274 iBu 0 H iPr H H H H iPr H H

275 tBu 0 H iPr H H H H iPr H H

276 Bn 0 H iPr H H H H iPr H H

277 Et 0 H iPr H H H H H iPr H

278 iPr 0 H iPr H H. H H H iPr H

279 iBu 0 H iPr H H H H H iPr H ~

280 tBu 0 H iPr H H H H H iPr H

281 Bn 0 H iPr HHHHH iPr H [Table 1-120]

Table 1 Compounds of Formula (1) (20) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q number

282 Et 0 H iPr H H H nPr H H H

283 iPr 0 H iPr H H H nPr H H H

284 iBu 0 H iPr H H H nPr H H H

285 tBu 0 H iPr H H H nPr H H H

286 Et 0 H H iPr H H nPr H H H

287 iPr 0 H H iPr H H nPr H H H.

288 iBu 0 H H iPr H H nPr H H H

289 tBu 0 H H iPr H H nPr H H H

290 Et 0 H iPr H H H iBu H H H

291 iPr 0 H iPr H H H iBu H H H

292 iBu 0 H iPr H H H iBu H H H

293 tBu 0 H iPr H H H iBu H H H

294 Et 0 H iPr H H H sBu H H H O

295 iPr 0 H iPr H H H sBu H H H

296 iBu 0 H iPr H H H sBu H H H

.

297 tBu 0 H iPr HHH sBu HHH [Table 1-21]

Table 1.Compounds of formula (1) (21)

[Table 1-22]

Table 1 Compounds of Formula (1) (22) Compounds

R1 A R2 R3 R4 R5 6 R7 R8 R9 R10 Q number

312 tBu 0 H iPr H H H sBu H H H

313 Ph 0 H iPr H H H sBu H H H

314 4-MePh 0 H iPr H H H sBu H H H ~

315 Bn 0 H iPr H H H sBu H H H

2-EtHe

316 0 H iPr H H H sBu H H H

X

317 POCEt 0 H iPr H H H sBu H H H

318 3-THF 0 H iPr H H H sBu H H H

319 Et 0 H iPr H H H sBu H H Ac

320 iPr 0 H iPr H H H sBu H H Ac

321 iBu 0 H iPr H H H sBu H H Ac

322 tBu 0 H iPr H H H sBu H H Ac

323 Et 0 H iPr H H H sBu H H Bz ~

324 iPr 0 H iPr H H H sBu H H Bz

325 iBu 0 H iPr HHH sBu HH Bz-<G ^ ^CH =

326 tBu 0 H iPr H H H sBu H H Bz

327 Et 0 Me iPr HHH sBu HHH [Table 1-23]

Table 1 Compounds of Formula (1) (23) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q number

328 iPr 0 Me iPr H H H sBu H H H

329 iBu 0 Me iPr H H. H sBu H H H

330 tBu 0 Me iPr H H H sBu H H H

331 Et 0 H H iPr H H sBu H H H

332 iPr 0 H H iPr H H sBu H H H

333 iBu 0 H H iPr H H sBu H H H

334 tBu 0 H H iPr H H sBu H H H

335 Et 0 H iPr H H H sBu H H H

336 iPr 0 H iPr H H H sBu H H H

337 iBu 0 H iPr H H H sBu H H H

338 tBu 0 H iPr H H H sBu H H H

339 Et 0 H iPr H H H sBu H H H

340 iPr 0 H iPr H H H sBu H H H

341 tBu 0 H iPr H H H sBu H H H

342 iBu 0 H iPr H H H sBu H H H

343 Et 0 H iPr HHH sBu HHH ~ [Table 1-124]

Table 1 Compounds of Formula (1) (24) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q

w

344 iPr 0 H iPr H H H sBu H H H

345 iBu 0 H iPr H H H sBu H H H

346 tBu 0 H iPr H H H sBu H H H

347 Et 0 H iPr H H H sBu H. H H

CH ₃

348 iPr 0 H iPr H H H sBu H H H

^ CH ₃

349 iBu 0 H iPr H H H sBu H H H

^ CH ₃

350 tBu 0 H iPr H H H sBu H H H

^ CH ₃

351 Et 0 H iPr H H H tBu H H H

352 iPr 0 H iPr H H H tBu H H H

353 iBu 0 H iPr H H H tBu H H H

354 tBu 0 H iPr HHH tBu HHH

[Table 1-25]

Table 1 Compounds of Formula (1) (25) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q w

367 Et 0 H iPr H H H H H Ph H

368 iPr 0 H iPr H H H H H Ph H

369 iBu 0 H iPr H H H H H Ph H

370 tBu 0 H iPr H H H H H Ph H

379 Et 0 H iPr H H H al! Yl H H H

380 iPr 0 H iPr H H H allyl H H H

381 iBu 0 H iPr H H H allyl H H H

382 tBu 0 H iPr H H H allyl H H H

387 Et 0 H iPr H H H H H H iPr

H ₃ C

388 iPr 0 H iPr H H H H H H iPr

H ₃ C

389 iBu 0 H iPr H H H H H H iPr

H ₃ C

[Table 1-126] Table 1 Compounds of formula (1) (26)

1 1 27] Table 1 Compounds of formula (1) (27)

[Table 1-128] Table 1 Compounds of formula (1) (28)

[Table 1-29]

Table 1 Compounds of Formula (1) (29) Compounds

R1 A R2 3 R4 R5 R6 R7 R8 R9 R10 Q

431 Et 0 H iPr H H H iPr H H H

432 iPr 0 H iPr H H H iPr H H H

433 iBu 0 H iPr H H H iPr H H H

434 tBu 0 H iPr H H H iPr H H H

435 Et 0 H iPr H H H sBu H H H

436 iPr 0 H iPr H H H sBu H H H

437 iBu 0 H iPr H H H sBu H H H

438 tBu 0 H iPr H H H sBu H H H

439 Et 0 H iPr H H H iPr H H H

OH

440 iPr 0 H iPr H H H iPr H H H. OH

441 iBu 0 H iPr H H H iPr H H H

442 tBu 0 H iPr H H H iPr H H H

OH

3-pe

443 Et 0 H iPr H H H H H H

ntyl

3-pe

444 iPr 0 H iPr H H H H H H

ntyl [Table 1-30]

Table 1 Compounds of Formula (1) (30) Compounds

R1 A R2 R3 R4 R5 R6 R7 8 R9 R10 Q number

3-penty

445 iBu 0 H iPr H H H H H H

I

3-penty

446 tBu 0 H iPr H H H H H H

I

447 Me 0 H iPr H H H iPr H H H

CI

448 Et 0 H iPr HHH iPr HHH-^- ^ci

CI

449 iPr 0 H iPr H H H iPr H H H

CI

450 iBu 0 H iPr H H H iPr H H H

CI

451 tBu 0 H iPr H H H iPr H H H

CI

452 Me 0 H iPr H H H sBu H H H

CI

453 Et 0 H iPr H H H sBu H H H

CI

454. IPr 0 H iPr HHH sBu HHH -Q- ^Cl

CI

455 iBu 0 H iPr HHH sBu HHH -Q- ^ci

CI

456 tBu 0 H iPr H H H sBu H H H

CI

457 Et 0 H iPr H H H iPr H H H

CF 厂 [Table 1-131] Table 1 Compounds of formula (1) (31)

[Table 1-32] Table 1 Compounds of formula (1) (32)

[Table 1-33] Table 1 Compounds of formula (1) (33)

[Table 1-134]

Table 1 Compounds of Formula (1) (34) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q

491 iBu 0 H iPr H H H iPr H H H

F

492 tBu 0 H iPr H H H iPr H H H

F

493 Et 0 H iPr H H H iPr H H H

494 iPr 0 H iPr H H H iPr H H H

495 iBu 0 H iPr H H H iPr H H H

496 tBu 0 H iPr H H H iPr H H H

CI

497 Et 0 H iPr H H H iPr H H H

CI

498 iPr 0 H iPr H H H iPr H H H

CI

499 iBu 0 H iPr H H H iPr H H H

CI

500 tBu 0 H iPr H H H iPr H H H ^

CN

501 Et 0 H iPr H H H iPr H H H

CN

502 iPr 0 H iPr HHH iPr HHH -ό [Table 1-35] Table 1 Compounds of formula (1) (35)

[Table 1-1 36] Table 1 Compounds of formula (1) (36)

[Table 1-37] Table 1 Compounds of formula (1) (37)

[Table 1-38]

Table 1 Compounds of Formula (1) (38) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 mo Q number

Br

537 Et 0 H iPr H H H iPr H H H

Br

538 iPr 0 H iPr H H H iPr H H H ~ _

Br

539 iBu 0 H iPr H H H iPr H H H

Br

540 tBu 0 H iPr H H H iPr H H H

541 Et 0 H iPr H H H iPr H H H

H ₃ C,

542 iPr 0 H iPr H H H iPr H H H

H ₃ C

543 Old u 0 H iPr H H H iPr H H H

544 tBu 0 H iPr H H H iPr H H H

545 Et 0 H iPr H H H iPr H H H

F F

546 iPr 0 H iPr H H H iPr H H H

F F

547 iBu 0 H iPr H H H iPr H H H

F F

548 tBu 0 H iPr H H H iPr H H H

FF [Table 1-139] Table 1 Compounds of formula (1) (39)

[Table 1-140] Table 1 Compounds of formula (1) (40)

[Table 1-41] Table 1 Compounds of formula (1) (41)

[Table 1-42]

Table 1 Compounds of Formula (1) (42) Compounds

¾ ° R1 A R2 3 R4 R5 R6 R7 R8 R9 R10 Q

590 Et 0 H H H iPr H H H H H

591 iPr 0 H H H iPr H H H H H

592 iBu 0 H H H iPr H H H H H

593 tBu 0 H H H iPr H H H H H

594 Et 0 H H H H H iPr H H H

595 iPr 0 H H H H H iPr H H H

596 Old u 0 H H H H H iPr H H H

597 tBu 0 H H H H H iPr H H H

598 Et 0 H Me H H H iPr H H H

599 iPr 0 H Me H H H iPr H H H

600 iBu 0 H Me H H H iPr H H H

601 tBu 0 H Me HHH iPr HHH [Table 1-43]

Table 1.Compounds of formula (1) (43)

Compound

R1 A R2 R3 R4 R5 R6 R7 R8 R9 RIO Q

602 Et 0 H Me Me H H iPr H H H

603 iPr 0 H Me Me H H iPr H H H

604 iBu 0 H Me Me H H iPr H H H

605 tBu 0 H Me Me H H iPr H H H

606 Et 0 H Et H H H iPr H H H-o

607 iPr 0 H Et H H H iPr H H H

608 iBu 0 H Et H H H iPr H H H

609 tBu 0 H Et H H H iPr H H H

610 tBu 0 H nPr H H H iPr H H H

(S

611 Et 0 H H H H iPr H H H

sBu-o

[Table 1-44]

Table 1.Compounds of formula (1) (44)

Compound

R1 A R2 R3 R4 R5 R6 R7 R8 R9 RIO Q

(s

612 iPr 0 H H H H iPr H H H

sBu

613 iBu 0 H H H H iPr H H H

sBu-o

(sy

614 tBu 0 H H H H iPr H H H

sBu -00

615 Et 0 H Ph H H H iPr H H H-o

616 iPr 0 H P H H H iPr H H H

617 iBu 0 H Ph H H H iPr H H H

618 tBu 0 H Ph H H H iPr H H H

619 Et 0 H Bn H H H iPr H H H

620 iPr 0 H Bn H H H iPr H H H-o

621 iBu 0 H Bn H H H iPr H H H

622 tBu 0 H Bn H H H iPr H H H

623 Et 0 H H Bn H H iPr H H H

624 iPr 0 HH Bn HH iPr HHH [Table 1-1 45]

Table 1 Compounds of Formula (1) (45) Compounds

1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q number

625 iBu 0 H H Bn H H iPr H H H-o

626 tBu 0 H H Bn H H iPr H H H

3-THF, H

627 Et 0 H H H iPr H H H

(Racemic)-o

3-THF, H

628 iPr 0 H H H iPr H H H

(Racemic)

3-THF, H

629 iBu 0 H H H iPr H H H

(Racemic)

3-THF, H

630 tBu 0 H H H iPr H H H

(Racemic) cHex

631 Et 0 H H H iPr H H H

(R3, R4 cyclization) cHex

632 iPr 0 H H H iPr H H H

(R3.R4 cyclization) cHex

633 iBu 0 H H H iPr H H H

(R3, R4 cyclization)-o cHex

634 tBu 0 H H H iPr H H H

(R3, R4 cyclization)

635 Et 0 H iPr H H H H H H H

636 iPr 0 H iPr H H H H H H H

637 iBu 0 H iPr HHHHHHH [Table 1-146]

Table 1 Compounds of Formula (1) (46) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q number

638 tBu 0 H iPr H H H H H H H

639 Me 0 H iPr H H H Me H H H

640 Et 0 H iPr H H H Me H H H

641 iPr 0 H iPr H H H Me H H H

642 iBu 0 H iPr H H H Me H H H

643 tBu 0 H iPr H H H Me H H H

644 Bn 0 H iPr H H H Me H H H

H, Me

645 Me 0 H iPr H H H H H

(Racemic)

H, Me

646 Et 0 H iPr H H H H H

(Racemic)

H, Me

647 iPr 0 H iPr H H H H H

(Racemic)

H, Me

648 iBu 0 H iPr H H H H H

(Racemic)

H, Me

649 tBu 0 H iPr H H H H H

(Racemic)

650 Et 0 H iPr HHH Et HHH [Table 1-47]

Table 1 Compounds of Formula (1) (47) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q number

651 iPr 0 H iPr H H H Et H H H

652 Old u 0 H iPr H H H Et H H H

653 tBu 0 H iPr H H H Et H H H

654 Et 0 H iPr H H H nPr H H H

655 iPr 0 H iPr H H H nPr H H H

656 iBu 0 H iPr H H H nPr H H H

657 tBu 0 H iPr H H H nPr H H H

658 Et 0 H iPr H H iPr H H H H

659 iPr 0 H iPr H H iPr H H H H

660 iBu 0 H iPr H H iPr H H H H

661 tBu 0 H iPr H H iPr H H H H

H, iPr

662 Me 0 H iPr H H H H H

(Racemic)

H, iPr

663 Et 0 H iPr H H H H H

(Racemic) [Table 1-1 48]

Table 1 Compounds of Formula (1) (48) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 mo Q

H, iPr

664 iPr 0 H iPr H H H H H

(Racemic)

H, iPr

665 iBu 0 H iPr H H H H H

(Racemic)

H, iPr

666 tBu 0 H iPr H H H H H

(Racemic)

667 Et 0 H iPr H H H H iPr H H

668 iPr 0 H iPr H H H H iPr H H

669 iBu 0 H iPr H H H H iPr H H-o

670 tBu 0 H iPr H H H H iPr H H

671 Et 0 H iPr H H H H H iPr H

672 iPr 0 H iPr H H H H H iPr H

673 iBu 0 H iPr H H H H H iPr H

674 tBu 0 H iPr H H H H H iPr H

675 Bn 0 H iPr H H H H H iPr H

676 Et 0 H iPr HHH iBu HHH [Table "! -49]

Table 1 Compounds of Formula (1) (49) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q

677 iPr 0 H iPr H H H iBu H H H

678 iBu 0 H iPr H H H iBu H H H

679 tBu 0 H iPr H H H iBu H H H

(sy

680 Me 0 H iPr H H H H H H

iBu

(sy

681 Et 0 H iPr H H H H H H

iBu isy

682 iPr 0 H iPr H H H H H H

iBu

(s-

683 iBu 0 H iPr H H H H H H

iBu

(sy

684 tBu 0 H iPr H H H H H H

iBu

(S)-

685 Me 0 H iPr H H H H H H

iBu

(sy

686 Et 0 H iPr H H H H H H

iBu

(sy

687 iPr 0 H iPr H H H H H H

iBu

(S)-

688 iBu 0 H iPr H H H H H H

iBu

(sy

689 tBu 0 H iPr H H H H H H

iBu [Table 1-150] Table 1 Compounds of formula (1) (50)

[Table 1-151] Table 1 Compounds of Formula (1) (51)

[Table 1-152]

Table 1 Compounds of formula (1) (52)

Compound

R1 A 2 R3 R4 R5 R6 R7 R8 R9 R10 Q

714 tBu 0 H iPr H H H tBu H H H-o

3-

715 Me 0 H iPr H H H penty H H H

I

3-

716 Et 0 H iPr H H H penty H H H

I

3- -co

717 iPr 0 H iPr H H H penty H H H

I

3-

718 iBu 0 H iPr H H H penty H H H

I

3-

719 tBu 0 H iPr H H H penty H H H

I

733 Et 0 H iPr H H Me Me H H H

734 iPr 0 H iPr H H Me Me H H H

735 iBu 0 H iPr H H Me Me H H H

736 tBu 0 H iPr H H Me Me, H H H

737 Et 0 H iPr H H H Me Me H H

738 iPr 0 H iPr H H H Me Me H H ~ <Ό

739 iBu 0 H iPr HHH Me Me HH [Table 1-1 53]

Table 1 Compounds of Formula (1) (53) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q

740 tBu 0 H iPr H H H Me Me H H

741 Et 0 H iPr H H H H Me Me H-o

742 iPr 0 H iPr H H H H Me Me H

743 iBu 0 H iPr H H H H Me Me H -co

744 tBu 0 H iPr H H H H Me Me H-o

CF3. H

749 Et 0 H iPr H H H H H

(Racemic)

CF3. H

750 iPr 0 H iPr H H H H H

(Racemic)

CF3. H

751 iBu 0 H iPr H H H H H

(Racemic)

CF3, H

752 tBu 0 H iPr H H H H H

(Racemic)

[Table 54] Table 1 Compounds of formula (1) (54)

[Table 1-55]

Table 1 Compounds of Formula (1) (55) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q number

768 Me 0 H iPr H H H iPr H H H-o

769 Et 0 H iPr H H H iPr H H H

CF3C

770 0 H iPr H H H iPr H H H

H2-o

771 nPr 0 H iPr H H H iPr H H H

772 iPr 0 H iPr H H H iPr H H H

773 nBu 0 H iPr H H H iPr H H H

774 Old u 0 H iPr H H H iPr H H H -co

775 tBu 0 H iPr H H H iPr H H H

776 Ph 0 H iPr H H H iPr H H H

777 Bn 0 H iPr H H H iPr H H H-o

778 OE 0 H iPr HHH iPr HHH [Table 1-1 56]

Table 1 Compounds of Formula (1) (56) Compounds

R1 A R2 R3 R4 R5 R6 R7 8 R9 mo Q number

779 vinyl 0 H iPr H H H iPr H H H

780 allyl 0 H iPr H H H iPr H H H propar

781 0 H iPr H H H iPr H H H

gyl-o

782 3-THF 0 H iPr H H H iPr H H H

THF-2

783 0 H iPr H H H iPr H H. H

-CH2

THF-3

784 0 H iPr H H H iPr H H H

-CH2-o cPr-C

785 0 H iPr H H H iPr H H H

H2

4,5-DE

786 P-2-C 0 H iPr H H H iPr H H H

H2

3 an

787 yl- 0 H iPr H H H iPr H H H

CH2

788 CICH2 0 H iPr H H H iPr H H H

CH3C

789 0 H iPr H H H iPr H H H

HCI

790 Et S H iPr H H H iPr H H H

791 iPr SH iPr HHH iPr HHH [Table 1-57]

Table 1 Compounds of Formula (1) (57) Compounds

R1 A 2 R3 R4 R5 R6 R7 R8 R9 mo Q number

792 iPr 0 Me iPr H H H iPr H H H-o

793 iPr 0 Ac iPr H H H iPr H H H-o

794 iPr 0 Bz iPr H H H iPr H H H-o o

795 Et 0 H iPr H H H iPr H H H o,

796 iPr 0 H iPr H H H iPr H H H

797 iBu 0 H iPr H H H iPr H H H

0,

798 tBu 0 H iPr H H H iPr H H H

799 Et 0 H iPr H H H iPr H H H '

800 iPr 0 H iPr H H H iPr H H H

801 iBu 0 H iPr H H H iPr H H H

802 tBu 0 H iPr HHH iPr HHH [Table 1-1 58]

Table 1 Compounds of Formula (1) (58) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q

803 Et 0 H iPr H H H iPr H H H

804 iPr 0 H iPr H H H iPr H H H

805 iBu 0 H iPr H H H iPr H H H

806 tBu 0 H iPr H H H iPr H H H

807 Et 0 H iPr H H H iPr H H H

808 iPr 0 H iPr H H H iPr H H H

809 iBu 0 H iPr HHH iPr HHH → nTT ⁰ ,

810 tBu 0 H iPr H H H iPr H H H

811 Et 0 H iPr H H H iPr H H H

812 iPr 0 H iPr H H H iPr H H H

813 iBu 0 H iPr H H H iPr H H H

814 tBu 0 H iPr H H H iPr H H H

815 Et 0 H iPr H H H iPr H H H

[Table 1-159] Table 1 Compounds of formula (1) (59)

[Table 1-60]

Table 1 Compounds of Formula (1) (60) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q number

828 iPr 0 H iPr H H H iPr H H H-Ho

829 iBu 0 H iPr H H H iPr H H H-Ho

830 tBu 0 H iPr H H H iPr H H H-Ho

831 Et 0 H iPr H H H iPr H H H ―

H ₃ C

832 iPr 0 H iPr H H H iPr H H H

H ₃ C

834 iBu 0 H iPr H H H iPr H H H

835 tBu 0 H iPr H H H iPr H H H

H ₃ C

836 Et 0 H iPr H H H iPr H H H

H

837 iPr 0 H iPr H H H iPr H H H

H

838 iBu 0 H iPr H H H iPr H H H

H

839 tBu 0 H iPr H H H iPr H H H

H

840 Et 0 H iPr H H H iPr H H H

841 iPr 0 H iPr HHH iPr HHH [Table 1-1 61]

Table 1 Compounds of Formula (1) (61) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q number

to s

842 iBu 0 H iPr H H H iPr H H H

843 tBu 0 H iPr H H H iPr H H H

844 Me 0 H iPr H H H iPr H H H

845 Et 0 H iPr H H H iPr H H H

846 iPr 0 H iPr H H H iPr H H H.

847 iBu 0 H iPr H H H iPr H H H

848 tBu 0 H iPr H H H iPr H H H

849 Me 0 H iPr H H H iPr H H H

850 Et 0 H iPr H H H iPr H H H Ding

851 iPr 0 H iPr HHH iPr HHH-<X7 ^CF3

852 iBu 0 H iPr H H H iPr H H H

853 tBu 0 H iPr HHH iPr HHH _CF3

854 Et 0 H iPr HHH iPr HHH [Table 1-162] Table 1 Compounds of formula (1) (62)

[Table 1-63] Table 1 Compounds of formula (1) (63)

[Table G] Table 1 Compounds of Formula (1) (64)

[Table 1-1 65]

Table 1 Compounds of Formula (1) (65) Compounds

R1 A R2 3 R4 5 R6 R7 R8 9 R10 Q number

886 tBu 0 H iPr H H H iPr H H H

887 Me 0 H iPr H H H iPr H H H

888 Et 0 H iPr H H H iPr H H H =

889 iPr 0 H iPr H H H iPr H H H

890 iBu 0 H iPr H H H iPr H H H =

891 tBu 0 H iPr H H H iPr H H H =

892 Et 0 H iPr H H H iPr H H H

893 iPr 0 H iPr H H H iPr H H H yj

-{ _N ,

894 iBu 0 H iPr H H H iPr H H H y

895 tBu 0 H iPr H H H iPr H H H y

-Q

896 Et 0 H iPr H H H iPr H H H

Racemic body [Table 1-66] Table 1 Compounds of formula (1) (66)

[Table 1-167] Table 1 Compounds of Formula (1) (67)

[Table 1-68] Table 1 Compounds of formula (1) (68)

[Table 1-69] Table 1 Compounds of formula (1) (69) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q number

929 tBu 0 H iPr H H H iPr H H H

930 Et 0 H iPr H H H iPr H H H

931 iPr 0 H iPr H H H iPr H H H

932 iBu 0 H iPr H H H iPr H H H

933 tBu 0 H iPr H H H iPr H H H

934 Et 0 H iPr H H H iPr H H H

935 iPr 0 H iPr H H H iPr H H H-

936 iBu 0 H iPr H H H iPr H H H

937 tBu 0 H iPr H H H iPr H H H

938 Et 0 H iPr HHH ¹ iPr HHH -o

939 iPr 0 H iPr H H H iPr H H H HO

940 iBu 0 H iPr H H H iPr H H H-

941 tBu 0 H iPr HHH iPr HHH [Table G 70] Table 1 Compounds of formula (1) (70)

[Table 1-71] Table 1 Compounds of formula (1) (71)

[Table 1 1 2]

Table 1.Compounds of formula (1) (72)

[Table 1-17-1] Table 1 Compounds of formula (1) (F 3)

[Table 1-1 74] Table 1 Compounds of formula (1) (74)

[Table 1-1 75]

[Table 1-1 76]

Table 1 Compounds of Formula (1) (76) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 mo Q number

― S

1018 jBu 0 H iPr H H H iPr H H H

1019 tBu 0 H iPr H H H iPr H H H

~

s,

1020 Et 0 H iPr H H H iPr H H H s,

1021 iPr 0 H iPr H H H iPr H H H

H ₃ C

s,

1022 iBu 0 H iPr H H H iPr H H H

H ₃ C

s,

1023 tBu 0 H iPr H H H iPr H H H

H ₃ C

S CH ₃

1024 Et 0 H iPr H H H iPr H H H

1025 iPr 0 H iPr H H H iPr H H H

1026 iBu 0 H iPr H H H iPr H H H

S CH ₃

1027 tBu 0 H iPr H H H iPr H H H

1028 Et 0 H iPr H H H iPr H H H

1029 iPr 0 H iPr H H H iPr H H H

1030 iBu 0 H iPr HHH iPr HHH [Table 1-77]

Table 1 Compounds of Formula (1) (77) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q number

s ci

1031 tBu 0 H iPr H H H iPr H H H s,

1032 Et 0 H iPr H H H iPr H H H

CI

s,

1033 iPr 0 H iPr H H H iPr H H H

CI

s,

1034 iBu 0 H iPr H H H iPr H H H

CI

s,

1035 tBu 0 H iPr H H H iPr H H H

CI

1036 Et 0 H iPr H H H iPr H H H

CI

1037 iPr 0 H iPr H H H iPr H H H

CI

1038 iBu 0 H iPr H H H iPr H H H

CI

1039 tBu 0 H iPr H H H iPr H H H

CI

1040 Et 0 H iPr HHH iPr HHH [Table 1 8]

Table 1 Compounds of Formula (1) (78) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 10 Q

1041 iPr 0 H iPr H H H iPr H H H-

1042 iBu 0 H iPr H H H iPr H H H

1043 tBu 0 H iPr H H H iPr H H H

1044 Et 0 H iPr H H H iPr H H H

Racemic body

1045 iPr 0 H iPr HHH iPr HHH

Racemic body

H iPr H H H -o ο 、

1046 iBu 0 H iPr H H

Racemic body

1047 tBu 0 H iPr H H H iPr H H H

Racemic body

1048 Et 0 H iPr H H H iPr H H H ― °

1049 iPr 0 H iPr H H H iPr H H H-o,

1050 iBu 0 H iPr H H H iPr H H H

― 0 ^

1051 tBu 0 H iPr H H H iPr H H H

0,

1052 Et 0 H iPr H H H iPr H H H

H ₃ Co,

1053 iPr 0 H iPr H H H iPr H H H

H ₃ C [Table 1-1 1] Table 1 Compounds of formula (1) (79)

[Table 1-1 80]

Table 1 Compounds of Formula (1) (80) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q

1067 tBu 0 H iPr H H H iPr H H H

1068 Et 0 H iPr H H H iPr H H H

⁰ Br

1069 iPr 0 H iPr H H H iPr H H H

1070 iBu 0 H iPr H H H iPr H H H

1071 tBu 0 H iPr H H H iPr H H H

1072 Me 0 H iPr H H H iPr H H H

1073 Et 0 H iPr H H H iPr H H H

1074 iPr 0 H iPr H H H iPr H H H

1075 iBu 0 H iPr H H H iPr H H H

1076 tBu 0 H iPr H H H iPr H H H

3 \

N

1077 Et 0 H iPr HHH iPr HHH, ゝ N] [Table 1-81]

[Table 1-82]

Table 1 Compounds of Formula (1) (82) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q number

1090 iPr 0 H iPr H H H iPr H H H

1091 iBu 0 H iPr H H H iPr H H H

1092 tBu 0 H iPr H H H iPr H H H

1093 Et 0 H iPr H H H iPr H H H

1094 iPr 0 H iPr H H H iPr H H H

1095 iBu 0 H iPr HHH iPr HHH ^ fr ^CH3

1096 tBu 0 H iPr H H H iPr H H H tr / zz- '飞 N

H ₃ C

1097 Et 0 H iPr H H H iPr H H H

S people CH ₃

1098 iPr 0 H iPr H H H iPr H H H

1099 iBu 0 H iPr H H H iPr H H H

1100 tBu 0 H iPr H H H iPr H H H

[Table 1-1 83]

[Table 1-84]

[Table 1-185] Table 1 Compounds of formula (1) (85)

[Table 1-1 86]

Table 1 Compounds of Formula (1) (86) Compounds

R1 A R2 R3 R4 R5 R6 R7 R8 R9 R10 Q F3

1133 Et 0 H iPr H H H iPr H H H

1134 iPr 0 H iPr H H H iPr H H H O

1135 iBu 0 H iPr H H H iPr H H H

1136 tBu 0 H iPr H H H iPr H H H

1137 Et 0 H iPr H H H CF3 H H H

1138 iPr 0 H iPr H H H CF3 H H H

1139 iBu 0 H iPr H H H iPr H H H

1140 tBu 0 H iPr HHH iPr HHH -co [Table 1-187]

Table 1 Compounds of Formula (1) (87) Compounds

1 A R2 R3 R4 R5 R6 R7 8 R9 R10 Q number

1145 Et 0 H iPr H H H iPr H H H

1146 iPr 0 H iPr H H H iPr H H H

1147 iBu 0 H iPr H H H iPr H H H

1148 tBu 0 H iPr H H H iPr H H H

1149 Et 0 H iPr H H H Me H H H

1150 iPr 0 H iPr H H H Me H H H

1151 iBu 0 H iPr H H H Me H H H

1152 tBu 0 H iPr H H H Me H H H:

1153 Et 0 H iPr H H H Me H H H

1154 iPr 0 H iPr H H H Me H H H

1155 iBu 0 H iPr H H H Me H H H

1156 tBu 0 H iPr HHH Me HHH

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¾ 圉 ¾ 曰山 Ή ZG L-16 L

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869 'ΗΖΛ) O 6 ・ 9 ΉΖ / L) 6 to 9 Ή3 / 1) to 9' ΗΖ / ί) /.9'9 Ή3 / 0999 8L9 ') 03'9 ΉΙ) 66 ε-96 Έ' (Ή3 ) 9 ・ ε- 'ε' (Ή3 / 98 -S8'L '(ω Ή3 /

6 to 8 L '(s Ή3 / 6) 6G 1 Ή3 / 6) 1' ( ^Ζ Η89 = Γ 'Ρ' ΗΖ / Ζ) 860 '(ΖΗ8'9 = Γ' Ρ 'Ζ / Ζ)

6Ό 'Ρ Ή 3/0 S80' (ΖΗ8 · 9 = Γ 'Ρ' Ζ / Ζ) 6 Ό ：: (w ^dd ' ^Ε Ιθαθ)? ΗΙίΊΝ-Η,

C 81 晋 ¾¾ 曰

Mountain ΉΟ LQ L- 9 L Mountain Ή3) 0Q L- L '(^ Ή2 / 1) WL' (Mountain Ήε) L

'(Mountain ΉΖ /) LZL' (mountain 'H2 / C) ZZL-61 L mountain''/ Ζ) SO—Otoichi L0' ( ^ω / L) 6'9— S6'9

'(Mountain / 12/1) 089 mountain' ΗΖ /) ε on 9 '(mountain' ΗΖ / Ι) '9 mountain' ΗΙ) 289-189 '(mountain' HL) 0 S '(mountain

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'(ω Ή2 / 0 88 L-981' (Mountain 'H2 / L) 8-1

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'P' ΗΖ / ε) l '(ΖΗ8'9 =' 'Ρ Ήε) S 1' (ΖΗ8 ・ 9 = Γ 'Ρ' Ζ / Ζ) 660 '(ΖΗ8 · 9 = Γ' Ρ 'Η2 / ε)

96Ό '(ΖΗ8 · 9 = Γ' Ρ 'ΗΖ / Ζ) C80'(ΖΗ8'9 = Γ 'Ρ Ή3 / 0 9 Ό ： (' ^ε Ιθαθ) 8 ΗΙΛΙΝ-Η!

One. 6.08 d'uj ¾ | ° | ¾ρ

9) One S9 'O' (ω Ή3) 6 One ε '(Mountain' ΗΖ / Ι)

WL '(^ Ήε) εε · 1 8Z' '(^ Ήζ / ι) and' (mountain Ήζ / ε) ΘΖΤ, -ΟΖΤ. '(Mountain Ήζ / ε) κτ

'(Mountain' HZ / 96.9-9 '(Mountain Ή3 / S 9) (Mountain' ΗΖ / Ι) 939 '(ΖΗ8 ・ 8 = Γ' Ρ Ή3 / 1) ε into 9 '(ω

9 L9 'HI) 169' ("J Ή 03 S '(mountain' ΗΙ) 80 '-SO' (ΖΗ8 · 9 = Γ 'b' Η3) 66Έ '(mountain' ΗΖ / Ι) 0Z.C '(mountain

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960 '(ΖΗ8'9 = Γ' Ρ 'H3 / C) ε8Ό'(ΖΗ8'9 = Γ 'Ρ' Η3 / ε) 9L.0: (mountain dd ' ^ε | θαο) 8 Η1ΜΝ-Η _ι

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0 _o 6G8L d uJ learning ^ ¾g

'(Mountain' HL) L9 L-Q9 L '(Mountain Ή 097.-81 ^ 7.' (^ 'Η3) Otoichi 8Ε ·' ( ^ω

'HL) OS' 8Z Mountain 'HL) ΙΓΖ.

09 'b ΉΙ) 68' (^ Ή2) 90 tons 6 · ε '(mountain' ΗΙ) 69'ε— Ι9.ε '(mountain ΉΟ S9e-3 X mountain' Η3)

16'L— 'L Mountain' HI) 291- ^ 1 '(ΖΗ8 · 9 = Γ' Ρ Ήε) ΖΖ ϊ '(zHC'9 = n' Ρ Ήε) ΙΖ Ι '( ^ζ Ηε'9 = Γ

'Ρ ΉΟ 660' ( ^ζ Ηε'9 = Γ 'Ρ Ήε) 6Ό' (ζΗε /.=Γ Ί Ήε) 080: (Jdd ' ^ε | οαθ) 8 ΗΙΛΙΝ-Η,

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SC6.TC/900Zdf/X3d l £ 80 / mu 00 OAV [Table 2-42]

Table 2. Properties of compounds (42)

Compound properties

¹ H-NMR δ (DMSO-d ₆ , ppm): 0.87 (3H, d, J = 6.8Hz), 0.93 (3H, d, J = 6.8Hz), 1.12-1.23 (6H, m), 2.13 (1H , q, J = 6.8Hz), 3.53—3.57 (2H, m), 3.60-3.69 (2H, m), 3.96

636 (1H, q, J = 6.8Hz), 4.87 (1H, br), 5.15 (1H, br), 6.68 (1H, br), 7.22-7.32 (1H, m), 7.40-7.52 (3H, m) , 7.66-7.69 (1H, m).

White crystals m.p. 162.8 ° C

NMR-NMR δ (DMSO-d ₆ , ppm): 0.87 (3H, d, J = 6.8Hz), 0.89 (3H, d, J = 6.8Hz), 0.94 (3H, d, J = 6.8Hz), 1.12 (3H, d, J = 6.8Hz), 1.86 (1H, q, J = 6.8Hz), 2.13-2.17 (1H, m), 3.55-3.57

637 (2H, m), 3.62-3.66 (2H, m), 3.75-3.89 (2H, m), 3.96 (1H, q, J = 6.8Hz), 5.22-5.25 (1H, m), 6.73 (1H, br), 7.27-7.32 (1H, m), 7.35-7.52 (3H, m), 7.65-7.68 (1H, m). White crystals mp 154.3 ° C

NMR-NMR δ (DMSO-d ₆ , ppm): 0.87 (3H, d, J = 6.8Hz), 0.93 (3H, d, J = 6.8Hz), 1.42 (9H, s), 2.11-2.20 (1H, m), 3.49—3.68 (4H, m), 3.88-3.91 (1H, m), 4.99 (1H, br), 6.55 (1H,

638

br), 7.27-7.31 (1H, m), 7.40-7.52 (3H, m), 7.66-7.68 (1H, m).

White crystals

Ή-NMR δ (CDCI ₃ , ppm): 0.81 (3H, d, J = 6.8Hz), 0.89 (3H, d, J = 6.8Hz), 1.25 (3H, d, J = 6.3Hz), 2.05-2.09 (1H, m), 3.47-3.52 (1H, m), 3.60-3.64 (1H, m), 3.68 (3H, s),

639 3.92-3.95 (1H, m), 4.20-4.24 (1H, m), 5.22-5.25 (1H, m), 6.47 (1H, br), 7.16 (1H, br), 7.28-7.32 (1H, m) , 7.40-7.51 (3H, m), 7.66-7.68 (1H, m).

White crystals m.p. 189.6 ° C

'H-NMR 6 (CDCI ₃ , ppm): 0.81 (3H, d, J = 6.8Hz), 0.89 (3H, d, J = 6.8Hz), 1.23 (3H, t, J = 6.8Hz), 1.25 ( 3H, d, J = 6.8Hz) _t 2.05-2.09 (1H, m), 3.48-3.53 (1H, m), 3.60-3.66 (1H,

640 m), 3.92-3.95 (1H, m), 4.10 (2H, q, J = 7.3Hz), 4.21-4.25 (1H, m), 5.21 (1H, br), 6.48 (1H, br), 7.19 ( 1H, br), 7.28-7.32 (1H, m), 7.40-7.52 (3H, m), 7.66-7.68 (1H, m). White crystals mp 197.2 ° C

¹ H-NMR δ (CDCI ₃ , ppm): 0.82 (3H, d, J = 6.8Hz), 0.89 (3H, d, J = 6.8Hz), 1.21-1.24 (6H, m), 1.26-1.27 (3H M), 2.05-2.09 (1H, m), 3.48-3.60 (2H, m), 3.87-3.92 (1H, m),

641 4.21-4.26 (1H, m), 4.88 (1H, q, J = 6.8Hz), 5.12 (1H, br), 6.48 (1H, br), 7.18 (1H, br), 7.28-7.32 (1H, m ), 7.40-7.52 (3H, m), 7.66-7.68 (1H, m).

White crystals m.p. 205.5 ° C

Ή-NMR δ (CDCI ₃ , ppm): 0.82 (6H, d, J = 6.8Hz), 0.89 (6H, d, J = 6.8Hz), 1.26 (3H, d, J = 6.8Hz), 1.83-2.00 (1H, m), 2.03-2.09 (1H, m), 3.47—3.51 (1H, m), 3.53-3.67 (1H _t m),

642 3.80-3.85 (2H, m), 3.87-3.93 (1H, m), 5.22 (1H, br), 6.42 (1H, br), 7.05 (1H, br), 7.27-7.30 (1H, m), 7.41 -7.51 (3H, m), 7.65-7.68 (1H, m).

White crystals m.p. 193.8 ° C

Ή-NR δ (CDCI ₃ , ppm): 0.82 (3H, d, J = 6.8Hz), 0.89 (3H, d, J = 6.8Hz), 1.27 (3H, d, J = 6.8Hz), 1.43 (9H , s), 2.06-2.10 (1H, m), 3.53—3.57 (2H, m), 3.84—3.88 (1H, m),

643 4.20-4.27 (1H, m), 5:01 (1H, br), 6.32 (1H, br), 7.20 (1H, br), 7.27-7.31 (1H, m), 7.39-7.51 (3H, m) , 7.66—7.68 (1H, m).

White crystal mp 163.3 ° C 0 _o Q i ^ ω: Xi ^ ¾ day

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6th 9 '(Mountain Ή2) 99 · ε-9ΐ7 · ε' (ΖΗ8 · 9 = Γ 'b' b / Ι) 1 Ζ '( ^Ζ Η8 · 9 = Γ' ^b 'Ζ / ϊ) 903' ( ^s Ή3 / 6) ΖΥ \

X ^s Ή2 / 6) 6ε ΐ '(2Ηε': Γ 'Ρ Ή £) 92' 1 '(ΖΗ8 · 9 = Γ' Ρ 'Ζ / Ζ) 960' (ΖΗ8 · 9 = Γ 'Ρ Ή2 / 0

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'(Mountain' ΗΙ) ^ Ζ ^ -ΖΖ ^ '( ^Ζ Η6'9 = Γ' ^b ΉΟ ε6 · ε '( ^ω ΉΟ 99'ε-09 · ε' ( ^ω Ήί) Z Z-9VZ LV9 '(ΖΗ8 9 = '' b Ή3 / 0 LVZ '(ΖΗ89 = Γ' b 'Ζ / ϊ) WZ' (ΖΗ89 = Γ 'Ρ Ήε) 9Ζ Ϊ' ( ^z H89 = n

'Ρ Ήε) VZ I' (ζΗε Ζ. = Γ 'Ρ Ήε) ΙΖ [' (ΖΗ8 ・ 9 = Γ 'Ρ Ή2 / Ε) ε6Ό' (ΖΗ8 ・ 9 = Γ 'Ρ' Ζ / Ζ)

68Ό '(ΖΗ8 · 9 = 厂' Ρ 'ΗΖ / Ζ) 880' (ΖΗ8 · 9 = Γ 'Ρ' ΗΖ / ε) 180: (mountain dd ' ^Ε | θαο)? ΗΙΛΙΝ-Η,

Oo /.991 d ai: s s ^ 曰

(Yamayama) 89 · B-99 '( ^ω

Ήε) ZQ L-OYL ΉΟ ZZ L-QZ L '(' ΗΙ) 39'9 q 'HI) 9fr'9 q ΉΟ 6 to S' ('HI)

^ Ζ ^ -ΖΖ ^ '(^ ΉΖ) i))''ΗΙ) O 6'ε— 16Έ' (ΉΙ) 99 · ε-09 · ε '( ^ω ' ΗΙ) 39 ε-9 ^ ε 9179 '( ΖΗ8 ・ 9 = Γ 'b' HZ) LVZ

'b' ΗΖ / Ι) WZ '(ΖΗ8 ・ 9 =''P' H2 / 09Z I '(ΖΗ8 · 9 = Γ

'P Ή2 / ε) 92Ί.' ( ^Ζ Ηε7. = Γ 'P Ήε) 9 \ l' (ΖΗ8 ・ 9 = Γ 'P' ΗΖ / Ζ) Z60 '(ΖΗ8 · 9 = Γ' Ρ Ή2 / 0

680 '(ΖΗ8 · 9 = “' Ρ 'Ζ / Ζ) 380' (ΖΗ8 · 9 = Γ 'Ρ' Η2 / ε) L8: (mountain dd ' ^ε | 〇αθ) 9 ΗΙΛΙΝ-Η,

One. 9f 81 Mountain: 暂曰

("J 'ΗΙ) 89'-99 · '(ω Ήε) Z ^ L-OYL' mountain 'ΗΙ) \ Z L-LZ L' ( ^J q Ή3 / 99'9 q

ΉΖ / Ο 2S 9 '(Jq ΉΟ 339' (Mountain Ή0 S 1 to 0 (Mountain 'ΗΙ) 00-16 ε) ( ^s Ή3 / 0 Z.9C Mountain

ΉΙ) S9 E-39 E '(Mi' Ζ / Ζ) Z '(Mountain' HI) OS'S-9fr'S '(ΖΗ8 9' ^b Ή3 / 1) 1 Z '(^ 3 = Γ

'b' ΗΖ / Ι) OZ '(ΖΗ8'9 = 5Τ' P 'Ζ / Ζ) 92'L' (ΖΗ8 ・ 9 ^ Τ 'P Ή3 / 0 931' (zH8'9 ^ r 'P

Ή2 / ε) C60 '( ^z H8'9 = f' P Ή3 / ε) 68,0 '{ ^Z HQ 9 = T' P Ή0 L80: (^ dd ' ^ε | 〇αθ) δ dlMN-H _t

0 _o 97.61 Sunshan 晋 ^ ¾3

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ΉΟ SZ'l- Wl '(ΖΗ8 · 9 = Γ' Ρ 'Η9) 680' ( ^Ζ Η8'9 = Ρ 'Ρ ΉΟ 180: (^ dd' ^ε | 000) 2 dlIN-H,

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SC6Z, TC / 900Zdf / X3d U £ 80 / L00Z ΟΛΧ 0. At S6L d uj ¾ ^H ¾¾5

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'(ω Ή2) 9t ^ —''(' HL) 0ZL-PI L '( ^ω ' I) 369-169 '(' ΗΙ) 9 9 one '9' (

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'Ρ Ή9) 90' L '(ΖΗ8 · 9 = Γ' P Ήε) 080 '(ΖΗ8 · 9 = Γ' Ρ Ήε) 9 / .Ό: (^ dd ' ^ε | οαθ) 8 ΗΙΙΝ-Η,

899ο 899t d ui 智 ^ ¾ 曰

ΉΙ) QQ L-L9 L

ΉΙ) ^ L-ZSL '(ω Ή2) Otoichi' '(ΉΟ ΟΖ' Ito 9 O '(' HI) 269-169 '(

IL9 'HL) S B 9_0 9'('q' HL) '(ΉΟ 9L'5-219' ( ^ω Ή2) l ^ -Zl 'ΗΙ) G6'C-68 ε

'ΗΙ) 09 C-frS e'('HL) · ε- · ε'('ΗΖ) ^ O Z-Wi Ήε) Z l-6l l' ( ^Ζ Η8'9 = Γ

'Ρ Ή9) 90''1' ( ^Ζ Η8 ・ 9 = Γ 'Ρ Ήε) 080' (ΖΗ8 ・ 9 = Γ 'Ρ Ήε) 9.: (w ^dd ' ^ε Ιθαθ) 8 ΙΛΙΝ-Η,

One. i l d uJ: Xi ^ ¾ 曰

'HL) /.9 Z.-997.' (Mountain Ήε) l 'L-iYL

'(ω Ή OZ L-LZ L' ( ^j q Ήΐ) SO '( ^J q' ΗΖ / Ι) L39 '(3Γ9' ( ^J 'HI) 009' (

'ΗΙ) 10 6 C' (^ ΉΟ 06.ε-08 · ε '(Ή3 / 1) 0Ζ. Ε-99Έ' (ΉΟ 89 C-99 C '(Ή3 / 1)

999 6 ε-8 ε '(Mountain' H3 / D '( ^ω Ή3 / 1) E03-10Z' (Mountain 'ΗΙ) 06 1 88.1 X ^s Ή2 / 6)

ε1 '(s ΉΖ / 6) 0 1' (ΖΗ89 = Γ 'Ρ' Ζ / Ζ) S01 '( ^ζ Ηε9 = Γ' Ρ Ή3 / Ε) C01 '( ^Ζ Η8'9 = Γ

'Ρ Ή2 / ε) LO L'(ΖΗ8'9 = Γ 'Ρ' H3 / C) 00 "1 '( ^Ζ Η8 ・ 9 = Γ' Ρ 'ΗΖ / Ε) 660' (ΖΗ8 · 9 = Γ 'Ρ 'ΗΖ / Ζ)

G6 '(ΖΗ8'9 = Γ' Ρ Ή3 / ε) /.80

'Ρ Ή3 / Ε) 28Ό: (mountain dd' ^ε | οαθ) δ ΗΙΛΙΝ-Η,

0 _ο 8.06 L

(UJ 'ΗΙ) L9 L-59 L Ή0 1 L-IVL Ή OZ L-LZ L q' ΗΙ)

907. '(ΉΙ) to 9 1 S 9' ('HL) 209' ('HL) 16 1 8' ('ΗΙ) 30 -66 £' ('HL)

f99 O 8.ε Yama Ή 3) SS G-8fr E '(Yama Ή ZQ Z ~ .QZ' ( ^ω ΉΙ) 06.1―88 '(Yama Ή9) <oVi-ZVi ■' (W9 = r 'P' ε) εθ ΐ '(ΖΗ8 ・ 9 = Γ' Ρ 'ΗΖ / Ο 660' (ΖΗ8 · 9 = Γ 'Ρ' ΗΖ / Ζ) 860 '(ΖΗ8 · 9 = Γ

'Ρ ΉΖ / Ζ) Ε6Ό' (ζΗ8 · 9 = Γ 'Ρ' ΗΖ) Ζ.8Ό '( ^ζ Ηε8'9 = Γ' Ρ ΉΟ 9Ζ.Ό ^: (^ ^dd ' ^Ε Ιθαθ) δ «ΙΛΙΝ-Η,

0 _ο ε 'td uj: ¾a¾¾g

ΉΙ) L9 L-99 L '(Mountain Ήε) 15 L-IYL' (^ 'HI) OZ L-LZ L

q 'ηζ / ϊ) so.'('q Ή2 / ο εο · n' ( ^j q Ή3 / 929 '(' q 'ΗΖ / Ι) 2i'9'(-> q ΉΙ) so.s Mountain

Ή ^) 2L -36'G '(ω Ήΐ) ε ε- Ι9'ε' (ΉΙ) Z ^ Z-LVZ ΉΖ / Ι) 90Ζ Ζ- Ο '(ΉΖ / l) 999 εθ'3-102 '(^' Ht) 88'L-8 '(' ΗΖ / ε) S 1— 1 'Η3 / ε) to 卜 ε L' (2 _Η 8'9 = Γ

'Ρ' ΗΖ / Ζ) 660 '(ΖΗ8 ・ 9 = Γ' Ρ 'Ζ / Ζ) 86.0' (ΖΗ8'9 = Γ 'Ρ' Υ \ Ζ / Ζ) C60 '(ΖΗ8 · 9 = Γ' Ρ ' (Ζ / Ζ)

8Ό '(ΖΗ8 ・ 9 = Γ' Ρ Ή3 / ε) 6 0 '(ΖΗ8'9 = Γ' Ρ Ή2 / ε) S Ό :( ' ^ε | οαο) 8 d NH,

0 ₀ C: Ji ^ 曰

(Yamayama) L9 L-59 L '(ω Ήε) LS -lf'Z.' (Yama 'ΗΙ) OZ L-LZ L' ( ^J

ΉΙ) 90 L '( ^J q ΉΖ / i) 929 q Ζ19 q ΉΙ) SL 9' (Ή3) 30 -S8 G '( ^s Ήε)

89.ε '(Ή3) ε9 ε-ε9 ε' ('ΗΖ) IQ Z-G Z Ήζ / i) 9ΟΉΟ.Ζ' (Ήζ / i) ζο ζ-ιο ζ 399

'(Mountain' HL) 88

'Ρ Ή3 / ε) 660' (ΖΗ8 ・ 9 = Γ 'Ρ' Ζ / Ζ) 86Ό '(ΖΗ8 · 9 = Γ' Ρ 'ΗΖ / ε) G60' (ζΗ89 = Γ 'Ρ' Ζ / Ζ )

980 '( ^Ζ Η8'9 = Γ' Ρ 'ΗΖ / ε) 6.Ό' ( ^ζ Ηε · O = Γ 'Ρ' Ζ / £) 8 '0: (mountain dd' ^ε | θαθ) § ΗΙΛΙΝ-Η ,

(Sese) ¾¾ 呦 ω 呦 ^ m

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Sf6 /, TC / 900Zdf / 13d OAV7: / κ £ £ ε6 / -ϊε900ζ <

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LOZ

SC6.TC/900Zdf/X3d nW80 / _00Z OAV

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60S

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• (w ΉΙ) 897.-S9 '(ΉΙ) 1 L-2VL Ή GZ L-BZ L

'( ^j q Ή 199' ( ^j q 'HI) 8 9' (jq Ή 9 to S '(ΉΙ) 6ε -93' (Ή U fr-mfr

91L 'HL) 66'ε-16' '(ω ΉΟ 0 ん · ε— 09Έ Ή OSC-L ^ e' ΉΙ) 60 — 00 '(

乙 ί) S · 1-09 · 1 '(^' Ht YI-L21 Ήε) SZ'L—6 to 1 '( ^Ζ Η8 "9 = Γ Ήε) 660' (ΖΗ8 · 9 = Γ

Ήε) 96,0 '(ΖΗ8 ・ 9 = Γ' Ρ Ήε) 98Ό '(ζΗε · = Γ' Ρ Ήε) Ό :( dd ' ^ε | οαθ) S dlMN-H,

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ΉΙ) 89 .-S9 Z. '(ω Ήε)' ( ^ω Ήί) G £ L-2Z L '( ^J q' HL) 09'9 '( ^J q' ΗΙ) 029 '( ^J q

9 L. 'ΗΙ) 8 to S' (ω 'Ι) 6C'fr-SZ Mountain' HL) 16 Z-LQ £ X ^s Ήε) L9 £ '( ^ω ' HI) 9 Z-09 £ '( ^ω

'ΗΙ) OS'S-' ε '(ΉΙ)' (ω ' _Hs ) & ι- £ ζ ΐ' (ΖΗ8 "9 = Γ ΉΟ 00 '(ΖΗ8 · 9 = Γ

'ϊ ΉΟ 560' (ΖΗ8 ・ 9 = Γ 'Ρ Ήε) 980' (ζΗε /.=Γ 'Ρ Ήε) L 0 dd' ^ε | οαθ) δ yiAIN-H _t

θο ε ει ：暂曰

'ΗΙ) 89Ή9 · Mountain ΉΙ) L' (^ '^) 8 Ο -Ο Ο ·' ί Mountain 'HI) ZZ L-6Z L' ('q

'HZ / E99 q ΉΖ / V) S 9'('q ΉΙ) 009' (ω 'HI) -00' (^ ΉΟ 08'ε_99ε '( ^ω

Ή3) 19 · ε— ε ε '(ΉΖ / 903-εθΖ' (Ή3 / 0861-96 I '(s Ή2 / 6) st' (s' ΗΖ / 6)

ZV \ '(s Ή2 / 6) 90 1' (s Ή2 / 6) 10 1 '(ΖΗ89 = Γ' Ρ 'Η3 / ε) £ 80' ('8.9 = Γ' Ρ 'ΗΖ / ε )

08.0 '(ΖΗ8'9 = Γ' Ρ Ή3 / 0 ΖΖ.Ό '(ΖΗ8'9 = Γ' Ρ 'ΗΖ / Ζ) 890' ^ε Ιθαθ) S ΗΙΛΙΝ-Η,

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YamaΉ 89 Z.-997. '(^ ΉΟ

W-ZS 'N' (ω Ή2) 2VL-0VL ΉΙ) '-8' ( ^J q 'ΗΖ / Ι) 00'B'('Ζ / Ϊ) 99'9- € 99

'(' ΗΖ / Ϊ) '(' q 'ΗΖ / Ι) 90 9' (mountain ΉΖ / i) —n 0 '(mountain Ή3 / 1) SO — 00' mountain 'HL)

ZIL

88 ・ ε -ja 8 ・ ε '(ΉΖ / V) 99 C-6S ε' (Ή3 / 1) 903-103 '(' (/ Ι) 86 l-E6 l '(ΖΗ8.9 = Γ

'Ρ' ΗΖ / ε) ΖΖ '(ZH8'S =''Ρ ΉΖ / Ζ) 6 to 1' (ζΗε9 = Γ 'Ρ' Ζ / Ζ) B to L '(ZH8 S = r' Ρ Ήζ / ε ) il l '(s Ή3 / 6) 901' (s Ή3 / 6) 101 '(ΖΗ8 ・ 9 = Γ' Ρ / 033/0380

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Ή2 / 1) 90Ζ-Ϊ10Ζ Ή3 / 861-96Ί. '( ^Ω ΉΟ 93 L-02 L'('ΖΧΗε / 6) LO l

'(s Ήε / 6) 10 l' ( ^Ζ Η8 · 9 = Γ 'P Ήε) C80' ( ^Ζ Η8'9 = Γ 'P Ήε) ZL O: (wdd' ^Ε | οαο) S ΗΙΛΙΝ-Η ₍

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SC6Z, Tf / 900Zdf / X3d UW80 contract Z ΟΛ \

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SC6.I £ / 900Zdf / X3d I ε80 / 00Ζ OAV

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SC6.lf / 900Zdf / X3d IIW80 contract OAV

g * I il 卟 ¾ (2b1) 145s7 ¾27

[8S-]

61Z

SC6.lf / 900Zdf / X3d U £ 80 / L00Z OAV

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[6S-3 拏] ozz

SC6.lC/900Zdf/X3d ll ^ £ 80 / .00Z OAV

'( ^J q Ήθ ε · 9' (ω ΉΙ) 'ss to s mountain Ή fr rt''( ^Z HG = Γ' b ΉΖ) GO mountain 'HD

00 · 68 · ε mountain ΉΙ) 19'G-39 C '(ω ΉΙ) 0S S-9 ε' (s Ήε) L2 Z '(S Ήε) U Z' (ω 'HL)

Z ΉΙ) L03-S61 '(ΖΗ8 · 9 = Γ'; ΉΟ 22 '1' (ΖΗ8 · 9 = Γ 'Ρ Ήε)' (ΖΗ8'9 = Γ

'Ρ' Η9) 060 '(ΖΗ8 · 9 = Γ' Ρ Ήε) S80 '(ΖΗ8 · 9 = Γ' Ρ ΉΟ 08Ό: (' ^ε | οαθ) 9 ΜΙΙΝ-Η, 398

(s ΉΙ) 898 '(Jq' ΗΙ) L3'8 '(s Ή 00.' ( ^Ζ Η8. = Γ 'Ρ' HI) Υ9 '(mountain' ΗΙ) W9-309

'(ω ΉΟ so g 86 · ε' (^ Ή2) 88 · ε-9 .ε Ήθ — ε ε Ήε) GL Z '(S Ήε) 993

Mountain ΉΟ-6.1 '(Yama Ή 176 L-681' (Mi Ή6) Z l '(ΖΗ8 · 9 = Γ.'Ρ Ήε) 001' ( ^Ζ Η8''9 = Γ

'Ρ ΉΟ 660' (ΖΗ8 ・ 9 = Γ 'Ρ ΉΟ 080' (ΖΗ89 = Γ 'Ρ Ήε) 0 Ό Ό (^ dd' ^ε | οαθ) 9 ytM -H _t L98

0 ₀ ε · 833 d uj tube ^ _¾曰

■ (s' HI) 89'8 '(-<q ΉΙ) G3 "8' (s' HL) L · 9 '(-" q' ΗΙ) C9'9 '(ΖΗ8 · 8 = Γ

'ρ ΉΟ 03 S' (ω 'ΗΖ) 50Ή6 ・ ε Ήε) B 8 ・ ε- ε8.ε Ή ί ^ · ε-^' ε ΉΟ 6

'(s Ήε) 99'Ζyama Ή 903-203' ΗΖ) 261-Z.8 L '( ^Ζ Η89 = Γ' Ρ Ήε) 86Ό '(ΖΗ8 ・ 9 = Γ

'Ρ Ή9) 060' (2Η89 = Γ 'Ρ Ήε) 280' (ΖΗ8 ・ 9 = `` 'Ρ Ήε) 69Ό: ( ^wdd ' ^ε Ιθαθ) δ ΗΙΛΙΝ-Η ,. 098

One. 883Ζ d iu s 曰 s ^ ¾g

(s' HI) 89'8

Ή 9Z'8-33'8 '(ΉΙ) £ 9- [L 9' HL) S99-19'9 '(Ή Z6 — 18 ·' (ω ΉΖ)

90V-Z6 Z '(Yama ΉΟ 98'ε-18 18ε' (^ Ή 9fr'S 0 εε (s Ήε) 6L Z '( ^s Ήε) 993' ( ^m

90 — 10 '(ω Ή S6'L— 68.1' (ζΗ8 · 9 = Γ 'Ρ' Η9) ΙΖ ί '(ΖΗ8'9 = Γ' Ρ Ήε) 00 · 1 '(ΖΗ8 · 9 = Γ

'Ρ Ήε) 86Ό' (ΖΗ8,9 = Γ 'Ρ ΉΟ 180' (^ Η89 = Γ 'Ρ ΉΟ 89Ό: ("Jdd' ^ε | οαθ) 9 H1MN-H, ^698. 9 ^{d liJ} ¾ ^Β ? ^ ¾5

(s' HI) .9'8 '(' q ΉΙ)

€ Z 8 '(s Ή ZL9' ( ^ω ΉΙ) 9-9S'9 '(^' HL) 6 S-S '(' Η3) ε to 60 '(' ΗΖ)

80Ή6 ・ ε '(mountain ΉΙ) 88'ε- 08-ε' (LU Ή 5 ^ ε-6εε X ^s Ήε) 6 '( ^s Ήε) 993' ( ^Ω 'HD

803-C03 '(Yama Ή 96 1-88.L' (ΖΗ8.9 = Γ Ήε) '( ^Ζ Η8'9 = Γ' Ρ Ήε) 00 '( ^Ζ Η8'9 = Γ

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One. S S61 'd uJ lesson ¾ 曰

(ΖΗ8 = Γ 'Ρ Ή S0'8' (ΖΗ8'8 = Γ

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012-203 ΉΟ ε6 · 1— 98'1

'Ρ Ήε) ΖΟΊ.

'Ρ Ήε) 001' (ΖΗ8 · 9 = Γ 'Ρ Ήε) f80' (ΖΗ8 · 9 = Γ 'Ρ ΉΟ 8 Ό: (^ dd' ^ε | οαθ) S ΗΙΛΙΝ-Η, 998

¾ 囯 3 曰

, (s 'ΗΙ) 03'8' (Yamayama 2) 9VL-ZVL X ^s 'ΗΙ) 90 /.' (Ρ 'ΗΙ) 9 to 9' (

ΉΙ) L0'9 '(Mountain' HL) C6 -68 '(^ Ήε) Z' (Mountain Ήί) 9Ζ C-03 C '(Mountain' ΗΗ)-

61) C61-881 '(Ή9) L'('ΗΖΙ) ZO L-060: (wdd' ^ε | 〇αθ) 9 ^ ΙΙΝ-Η, L98

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SC6.TC/900rdf/X3d 80 £ 80 / m00 Ο / Α

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SC6.TC/900Zdf/X3d 1 £ 80 / _00 OAV

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SC6.TC/900Zdf/X3d U £ 80 / L00Z OAV

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L

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8ZZ

S 6LU / 900Zdr / 13d 1 £ 80 / n OOZ OAV

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S £ 6LW900ZdT / Ud 1 Mu 00 OAV

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SC6, Tf / 900Zdf / X3d

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Sf6.TC/900Zdf/X3d ΐ ε80 / 00Ζ OAV L

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SE

[2B-]

Sf6.TC/900idf/X3d ΐ £ 80 OAV

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'(ω ΉΟ にに Ζ— 0 to Ζ' (mountain Ή 061-981 Ή6) ΖΥΙ '( ^ζ Ηε · =''Ρ ΉΟ 001' WL =

'Ρ Ήε) 86Ό' (ΖΗ8 ・ 9 = Γ 'Ρ Ήε) L60

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0 _o 6 tO3 d-uJ ¾ ^B ¾¾5

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'(ω ΉΙ) 9 ^ .- ^.' (2Ht 'S'6 e = r' PP 'HI) SO.' ( ^ω 'HI) 869' (ω ΉΟ 8 to 9 '( ^ω ΉΟ US

8L0L '(Mountain ΉΟ 56 ε-36 Έ' (ΖΗ8 '8 ・ 9 = Γ' PP 'ΗΙ) 06 G' (ΖΗ8 ・ 9 = Γ 'Ρ' Η3) '(Mountain Ή 9S C' (Mountain

S) zs's-8 ε '(Ήί) ε to ζ― ι to ζ' (Ή3) ε6 · 卜 '(ΖΗ8.9 = Γ' Ρ Ήε) οο ι '(ζιπε

'Ρ ΉΟ 860' (ΖΗ8 ・ 9 = Γ 'Ρ' Η9) 160 '( ^Ζ Η8'9 = Γ' Ρ 'Η9) 580-(^ dd' ^ε | θαθ) δ Η Ν-Η ₍

'Ρ Ή 1ST.

'Ρ Ή LV9

'b' HL) '(mountain Ή0 Z.6C-36C' (? Η8 · 'ε9 = Γ Z.LOL' PP 68) 68C '(' HL) 69G '(Ή0 SfrS' ( '(' HO l6 L-fr8 l

'ρ Ήε) ΖΖ Ϊ' ( ^ζ Ηε'9 = Γ 'ρ Ήε) on' (ΖΗ8.9 = Γ 'Ρ Ήε) οο.ι

'Ρ Ήε) 860' (ΖΗ8 · 9 = Γ 'Ρ Ήε) 06' (ΖΗ8 · 9 = Γ 'Ρ ΉΟ 98Ό: (wdd' ^ε ΐοαθ) S dlAIN-H _L q Ήθ L6 L '( ^ω Ή s ε '(jq ΉΟ εζ 9'('q Ήθ 96 Ήε) so' ( ^s

Ήε) 10 '(ω' HD 00 G 68.ε '(ω ΉΙ) L9'S- frS'S mountain' ΗΖ) 0S'S-9 ε '(ω' HL) Z-S03 9L0L mountain 6) VI '(s Ή3 / 6) 3t- l' ( ^Z H8'9 = P 'P HC) 660' ( ^Ζ Η89 = Γ

'P Ή9) 96Ό' (ΖΗ8 · 9 = Γ 'P Ήε) 88.0' (ΖΗ8.9 = Γ 'P Ήε) 18Ό: (' ^ε | θαθ) S dlMN-H,

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q 'HI) U 8

'(Mountain' HI) S Otsuichi ε q ΉΙ) 809 '(Jq Ή 90'S Mountain' ΗΙ) 16 -98 Mountain 'Ι) do -m

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'(s Ήε) so' ( ^s Ήε) ιο '(Ή οβ · ε- 8 · ε' (Ήΐ) 09 c-zs c '(') 09 ε-9 ^ ε

Ή 90-66 '(HL) 26- 1-98- L Mountain' Η9) '(ΖΗ8 ・ 9 = Γ' Ρ Ήε) 660 '( ^Ζ Η89 = Γ

'Ρ Ήε) fr6 "0' ( ^Ζ Η8 · 9 = Γ 'Ρ' ΗΕ) C80 '( ^Ζ Η8.9 = Γ' Ρ Ήε) 6 / .Ό :( ^mdd ' ^ε Ιθαθ) 8 ^ ΙΛΙΝ-Η,

0 _o 9'8.l

q Ή2 / 0

Z.0'8 '(Jq Ή3 / L6 L' HL) S-ε garment '( ^J q Ή1) 239 q' HL) 90'9 '(' ΗΖ) に

3L0L Ήε) so '(s Ήε ) ιο' ( mountain ^{Ή οο -88 ε '(ω'} HI) 09 ε-ε9 ε '(ω' ΗΖ) os'e-9 · ε '(ω

'ΗΙ) 902-102' () I6 l-98 "t '(mountain Ήε) Wl-Wl' (ΖΗ8 ・ 9 = Γ 'P Ήε) 101' (2Η8 ・ 9 = Γ

'P ΉΟ 66' (ΖΗ8 ・ 9 = Γ 'Ρ Ήε) G8O' (ΖΗ8 ・ 9 = Γ 'Ρ Ήε) 8Ζ.Ό :(' ^Ε | θαο) 9 dlAI -H!

¾ 固 ¾ 曰

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'P ΉΙ) 929'('q') LI Q '(s'^)' ( ^s Ή010V '(mountain' HI) 00t 06 · ε '( ^s Ήε) 9 · ε ι ιοι' (mountain Ή3) 3 .Έ-09'ε Mountain 'HI) LY £ -ZVZ' ( ^Ζ Η8 ・ 9 = Γ 'b ΉΙ) VO Z'(ΖΗ8'9 = Γ 'b ΉΟ 881' (Mountain

Ή9) εθ Ι-ε6Ό '(ΖΗ8'9 = Γ' Ρ Ήε) 8Ό '( ^Ζ Η89 = Γ' Ρ Ήε) 8.Ό :( ^{ε | ε |} ' ^ε Ιθαθ) § ΗΙΛΙΝ-Ηι

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呦 ^ q

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[I]

SC6.TC/900Zdf/X3d Tll7C80 / .00r OAV

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S £ 6Ll £ / 900Zd £ / 13d ΐ £ 80 / M00∑ OAV

Ζ ζ No. ["1 2 拏]

S £ 6.TC / 900∑df / X3d 80 £ 80 / M00 OAV

[8 —]

6EZ

SC6.TC/900Zdf/X3d nW80 / _00Z OAV

[6B-]

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(Table 3)

Compound number General formula number

20 00 Compounds represented by general formula (3)

20 0 1 Compound represented by general formula (4)

Table 4 below shows typical compounds represented by the general formula (5) which are active ingredients of the fungicide of the present invention, but the present invention is not limited to these.

In Table 4, Me represents a methyl group, iPr represents an isopropyl group, and tBu represents a tertiary butyl group.

(Chemical 3)

(Table 4)

Table 5 below shows typical compounds of the compound represented by the general formula (6), which is an active ingredient of the fungicide of the present invention, but the present invention is not limited thereto. In Table 5, Me represents a methyl group, i Pr represents an isopropyl group, and t B u represents a tertiary butyl group. JP2006 / 317935

253

(Chemical 3 3)

(Table 5) Compound No.R19 R20 R21 R22 R23 R24 R25 R26

2 0 0 5 F3CCH2 H iPr H H H H

2 0 0 6 F3CCH2 H tBu H H H H

2 0 0 7 F3CCH2 H iPr HHHH

Table 6 below shows representative compounds of the compound represented by the general formula (9) which are active ingredients of the insecticide of the present invention, but the present invention is not limited to these.

(Chemical 3 7)

(Table 6)

Table 7 below shows typical compounds represented by the general formula (10) which are active ingredients of the insecticide of the present invention, but the present invention is not limited to these.

(Chemical 3 8)

(Table 7)

[Formulation examples and test examples]

Next, formulation examples and bactericidal activity test examples of the bactericide according to the present invention are shown. In the following description, “part” means “part by weight” or “% by weight”.

[Formulation Example 1] (Dust)

Compound No. 30 9 Compound 2 parts Oppy clay 9 8 parts were mixed and ground uniformly to obtain a powder containing 2% of active ingredient.

[Formulation example 2] (Wetting agent)

Compound No. 1 6 4 Compound 1 0 parts, Kaolin 70 parts, White Carbon 1 8 parts Then, 2 parts of calcium alkylbenzene sulfonate was uniformly mixed and powdered to obtain a wettable powder containing 10% of the active ingredient in the form of fine powder of uniform composition.

[Formulation Example 3] (Wetting agent)

Compound No. 20 4 Compound 20 parts, calcium alkylbenzene sulfonate 3 parts, polyoxyethylene nonyl phenyl ether 5 parts and clay 7 2 parts uniformly mixed and pulverized, active ingredient in the form of fine powder of uniform composition A wettable powder containing 20% was obtained.

[Formulation Example 4] (Wetting agent)

Compound No. 6 8 2 compound 50 parts, sodium lignin sulfonate 1 part, white carbon 5 parts and diatomaceous earth 4 4 parts were mixed and ground to obtain a wettable powder containing 50% active ingredient. .

[Formulation Example 5] (Flowable)

Compound No. 9 5 1 compound, 5 parts propylene glycol, 4 parts sodium lignin sulfonate, 2 parts dioctyl sulfosuccinate sodium salt, and 8 parts water are wet-ground with a sand grinder. A flowable preparation containing 5% of the active ingredient was obtained.

[Formulation Example 6] (Flowable)

Compound No. 87 2 Compound 10 parts, propylene glycol 7 parts, sodium lignin sulfonate 2 parts, dioctyl sulfosuccinate sodium salt 2 parts, and water 79 parts wet-ground with a sand grinder Thus, a flooring agent containing 10% of the active ingredient was obtained.

[Formulation Example 7] (Flowable)

Compound No. 1 0. 2 5 Compound 2 5 parts, Propylene glycol 5 parts, Polyoxyethylene oleate acid ester 5 parts, Polyoxyethylene dilinole ether senolate 5 parts, Silicone defoamer 0. 2 parts and 59.8 parts of water were wet-ground with a sand grinder to obtain a flowable agent having an active ingredient of 25 ° / ₀ .

[Formulation Example 8] (Wetting agent)

Compound No. 7 72 Compound 1 2.5 parts, Manzeb 37.5 parts, sodium lignin sulfonate 5 parts, sodium alkylnaphthalene sulfonate 5 parts, why 卜 carbon 5 parts and diatomaceous earth 3 5 Parts were uniformly pulverized and mixed to obtain 100 parts of a wettable powder.

[Formulation Example 9] (Wetting agent) Compound No. 7 6 9 compound 5 parts, chlorothalonil 10 parts, sodium lignin sulfonate 5 parts, sodium alkylnaphthalene sulfonate 5 parts, white carbon 5 parts and caustic soil 70 parts are uniformly ground and mixed. 100 parts of a summing agent was obtained.

[Formulation example 1 0] (Wetting agent)

Compound No. 10 6 9 Compound 1 2.5 parts, phorpet 50 parts, sodium lignin sulfonate 5 parts, sodium sodium alkylnaphthalenesulfonate 5 parts, white carbon 5 parts and diatomaceous earth 22.5 Parts were uniformly pulverized and mixed to obtain 100 parts of wettable powder.

[Formulation example 1 1] (Flowable agent)

Compound No. 7 6 9 Compound 5 parts, Simoxanyl 10 parts, Carboxymethylcellulose 3 parts, Lignin sulfonate 2 parts, Dioctino sulfosuccinate 卜 Sodium salt 1 part and Water 7 9 parts Sand grinder And wet milled to obtain 100 parts of a flowable agent.

[Formulation Example 1 2] (Flowable)

Compound No. 4 4 9 Compound 10 parts, Metalaxyl 10 parts, Carboxymethylcellulose 3 parts, Sodium lignin sulfonate 2 parts, Dioctylsulfosuccinate sodium salt 1 part and water 7.4 parts in a sand grinder Wet pulverization gave 100 parts of a mouth-able bleed.

[Formulation example 1 3] (Flowable agent)

Compound No. 6 87 Compound 10 parts, Azoxystrobin 10 parts, Carboxymethyl cellulose 3 parts, Lignin sulfonate 2 parts, Dioctyl sulfosuccinate sodium salt 1 part and Water 7 4 parts Wet milled with a sand grinder to obtain 100 parts of a flowable agent.

[Formulation example 1 4] (Flowable agent)

Compound No. 44 9 Compound 10 parts, dimethomorph 10 parts, carboxymethylcellulose 3 parts, sodium lignin sulfonate 2 parts dioctylsulfosuccinate sodium salt 1 part and water 7 4 parts in a sand grinder Wet milled to obtain 100 parts of a flowable agent.

[Formulation Example 1 5] (Emulsion)

Compound No. 30 09 Compound 10 parts, Imidacloprid 10 parts, Cyclohexane 10 parts, Xylene 50 parts and Solpol (Toho Chemicals Surfactant) 20 parts uniformly dissolved and mixed in Emulsion 1 0 ◦ part was obtained. [Formulation Example 1 6] (Wetting agent)

Compound No. 10 3 1 Compound 10 parts, ferimzone 20 parts, sodium lignin sulfonate 1 part, sodium alkylbenzene sulfonate 2 parts and caustic soil 6 7 parts are uniformly ground and mixed with wettable powder 1 0 0 parts were obtained.

[Formulation example 1 7] (Granule)

5 parts of the compound of Compound No. 1 48, 5 parts of the compound of Compound No. 200, 0.5 part of the wetting agent, 3 parts of the binder, 5 parts of talc, and 7 parts of the clay 7 1. After that, it was molded by an extrusion granulator. The obtained molded product was dried and then sized to obtain 100 parts of granules.

[Formulation example 1 8] (Dust)

Compound No. 7 72 Compound 1.0, Fursulfamide 0.3 parts, Flocculant 0.3 parts, Clay 50 parts, Calcium carbonate 48.4 parts are mixed, and pulverized with a pin mill. 100 parts were obtained.

Next, the effect of the fungicide of the present invention will be specifically described with reference to test examples.

[Test Example 1]

Tomato plague control trial

A tomato (variety: the best in the world; one stand) was planted in a plastic pot with a diameter of 7.5 cm in a greenhouse and grown until the fifth true leaf developed. After the chemical solution diluted to the prescribed concentration is thoroughly sprayed onto the foliage and the chemical solution is dried, a zoospore suspension of the tomato plague fungus iPh ytophthorainfestans) is inoculated into the foliage and sprayed in a wet chamber at 18 ° C. Kept for 4 days. Four days after the inoculation, the area occupied by the epidemic lesions per tomato leaf was investigated according to the following indicators, and the control value was calculated from the average disease incidence consisting of the average of the disease disease index in each ward according to the following formula: . The results are shown in Table 8.

Disease index 0: No disease

1: The lesion area rate is less than 5%

2: The lesion area rate is 5 to less than 25%

3: The lesion area rate is less than 25 to 50%

4: The lesion area rate is 50% or more

Control value (%) = (1—Severity of treated area / Severity of untreated area) XI 0 0 (Table 8

^^ ffi

(ppm)%) Compound 1 64 50 95 Compound 3 09 50 90 Compound 7 69 50 98 Compound 7 72 50 97 Compound 951 50 96 Compound 1 025 50 88 Compound 1 069 50 95

¾S properties ¾formation ffl 1500 95 dimethyl morph 50 98 azoxis robin 50 98 ƒ7 moxadone 100 8B fenamidone 50 96 zoxa ¾ 卜 50 85 mandipropamide 50 98 compound 2 00 50 96 compound 1 64 + ¾ qualitative +1500 100 Compound 1 64 + Dimethomorph 50 450 100 Compound 1 64 + Axoxys Robin 50 0 100 Compound 1 64 + Famoxadone 50 + 100 100 Compound 64 + Huamidon B0 + 50 100 Compound 1 64 + Zoxamide 50 + 60 100 Compound 1 64 + Manifropamide 50- + 50 100 Compound 1 6 + Compound 2001 50-¾0 100 Compound 309 + Fertilization SH 50 + 1500 100 Compound 309 + Dimethomorph 50 450 100 Compound 309 + Azoxys robin 50 450 100 Compound 309 + Famoxadone B 0 + 100 100 Compound 309 + Funamidone 50 450 100 Compound 309 + Soxamide 50 450 100 Compound 309 + Manifropamide 50 460 100 Compound 309 + Compound 2001 50 + 50 100 Compound 7 69 + Degradation SB B0 + 150 0 100 Compound 769 + Dimethomorph 50-t50 100 Compound 769 + Azoxystrobin 5CH50 100 Compound 769 + Famoxadone 50 + 100 100 Compound 7 69 + Phenamidone 50 + 50 100 Compound 769 + Soxamide 50 450 100 Compound 769 + Maniflovamide 100 Compound 769 + Compound 2001 50 + 50 100

(Table 8) (continued)

[Test Example 2]

Cabbage root-knot control test by soil treatment

A predetermined amount of powder was mixed with the soil, and cabbage seedlings (variety: seasonal harvest) were planted in a field where the root-knot disease P l a sm o d i o p ho r a b r a s s i c a e) was observed. After 60 days of treatment, the strains were extracted, the occurrence of clubroot was investigated according to the degree, and the control value was calculated by the following formula from the average disease degree consisting of the average of the disease index in each section. The results are shown in Table 9. In the table, g a i represents the amount of active ingredient (g).

Disease index 0: Does not recognize root-knot formation.

1: Root bumps are growing on less than 1 to 25% of the whole root system.

2: The root humps grow on less than 25 to 50% of the whole root system.

3: Root bumps grow on less than 50 to 75% of the entire root system. 4: Root humps grow on more than 75% of the root system.

Control value = (1 Average disease severity in one treatment zone) Average X 1 0 0

(Table 9)

[Test Example 3]

Japanese cucumber powdery mildew control trial

In a greenhouse, plant cucumbers (variety: Sagamihanjiro; one stand) in plastic pots with a diameter of 7.5 cm, grow until the first true leaf develops, and then prepare the medicinal preparation prepared to the prescribed concentration. A sufficient amount was sprayed. One day after spraying, the powdery mildew fungus on the diseased leaves of cucumber, Spha a ro het c a f u 1 i gin e a), was inoculated evenly with a paint brush and inoculated 10 days later. The area occupied by lesions per leaf of cucumber was investigated according to the following index, and the control value was calculated from the average disease severity consisting of the average of the disease index in each section by the following formula. The results are shown in Table 10.

Disease index 0: No disease

1: The lesion area rate is less than 5%

2: The lesion area rate is less than 5-25%

3: The lesion area rate is less than 25 to 50%

4: The lesion area rate is 50. /. more than

Control value (%) = (1—Severity of treated area, Severity of untreated area) X I 0 0

(Table 1 0) Prevention ^ fffi

试试桀 dispenser

(ppm) (%)

Convertible 3 250 50

Compound 1 84 250 55

Compound 238 250 55

Compound 261 250 60

Compound 84 S 250 65

Pentobilad 3.15 95

Asoxys Robin 10 98 Compound 3 + Pentobirad 250 + 3.15 100

Compound 3 + Azoxystrobin 250 + 10 100

Compound 1 84 + pentiovirad 250 + 3.15 100

Convertible 1 84 + Asoxystrobin 250 + 10 100

Compound 238 + Pentobirad 100

Compound 238 + azoxystrobin 100

o o

Compound 26 1 + pentiovirad σ o 100

Compound 261 + Azoxys Robin 100

m

Compound 848 + pentiovirad 250 + 3.15 100

Compound 848 + asoxystrobin 250 + 10 100

[Test Example 4]

Control test of cucumber seedling blight by soil treatment

In a 7.5 cm diameter plastic pot, 5 cucumber seeds (variety: Sharp 1) per pot and ¾ thread of the seedling blight fungus Pythiumaphanide rm at urn previously grown on PDA medium. Four agar tisks (ik diameter 6 mm) were placed on the pot and covered with soil. Here, the drug solution diluted to a predetermined concentration was irrigated. The number of seedlings that withered after 14 days was investigated, and the control value was calculated by the following formula from the average disease severity consisting of the average of the disease disease index total of each section. The results are shown in Table 11. In the table, mgai represents the amount of active ingredient (mg).

Disease index 0: No disease

1: Poor growth

2: Withering

Control value = (1 Average disease severity in one treatment area / average disease incidence in no treatment area) X I 0 0

(Table 1 1) ¾ reason

昉 iffi

¾¾SiJ (mgai

Earthenware (,%)

Compound 309 4 50

Compound 7 69 4 75

Compound 7 72 4 75

Compound 951 4 60

Compound 1 069 4 70

Metalaxyl 0.25 93

Propamore Club 3 93

Compound 309 + metalaxyl 100

Compound 309 + propamo ¾ ruf 100

Compound 769 + metalaxyl 4-K3.25 100

Compound 769 + propamorph 4 100

Compound 772 + metalaxyl 100

Compound 772 + propamocalp 100

Compound 951 + Metalaxyl 100

Compound 951 + propamorph 100

Compound 1 069 + mexil 440.25 100

Compound 1 069 + Propamocalf 4 β 100

[Test Example 5]

Grape downy mildew control test.

A sufficient amount of the drug solution prepared at a predetermined concentration was sprayed on the cuttings of grapes planted in a plastic pot with a diameter of 15 cm (variety: Cabernet Sauvignon; 45 leaves). One day after spraying, inoculate a conidial suspension of the downy mildew fungus Pla smop a ravi ic i c o 1 a) and let the seedlings grow in a humid room at 25 ° C for 10 days. The area occupied by lesions on the three true leaves from the base of each plant was investigated according to the following index, and the control value was calculated using the following formula from the average disease severity consisting of the average of the total disease index of each section. . The results are shown in Table 12.

Disease index 0: No disease

1: The lesion area rate is less than 5%

2: The lesion area rate is less than 5 2 5%

3: The lesion area rate is less than 2550%

4: The lesion area rate is 50% or more

Control value (%) = (1 Disease severity in one treatment group No disease treatment) X 1 0 0 (Table 1 2

(Table 1 2 (continued)

[Test Example 6]

Metalaxyl-resistant cucumber and disease control test

In the greenhouse, cucumbers (variety: Sagamihanjiro; 2 stand) were planted in plastic pots with a diameter of 7.5 cm and grown until the first true leaf developed. After spraying the drug solution diluted to the prescribed concentration on the foliage and drying the drug solution, spray-inoculate a conidial suspension of Pseudoperonosporacuben sis that has acquired resistance to metalaxyl and 2 It was kept in a 5 ° C wet room for 10 days. 10 days after the inoculation, the area occupied by the lesions of roots and fungi per cucumber leaf is investigated according to the following index, and the following formula is calculated from the average disease severity consisting of the average of the disease index in each section. The control value was calculated at The results are shown in Table 13.

Disease index '0 _: No disease ·

1: The lesion area rate is less than 5%

2: The lesion area rate is 5 to 25. /. Less than

3: The lesion area rate is less than 25 to 50%

4: The lesion area rate is 50% or more

Control value (%) = (1 Disease severity in one treatment zone / Disease severity in no treatment zone) XI 0 0 (Table 1 3

National hospital price ¾ row (ppm) () Compound 2 0 50

Compound 3 O 9 50

Compound 4 9 50

Compound 6 8 2 50

Compound 6 8 7 50

Compound 7 6 9 50

Compound 7 7 2 50

Compound 8 7 2 50

Compound 9 5 1 B0

Compound 1 0 6 9 50

Melaxyl 50

Azoxystron 50

Simoxanyl 100

Famoke Don 50

Chlorothalonil 100

Cetyl 1600

Compound 2 0 0 0 50

Compound 2 O 4 • Metafoxyl 50 + 50 94 Compound 2 0 4 • Azoxys Mouth Bottle 50 + 60 100 Compound 2 0 4 -Simoxanyl 50 + 100 100 Compound 2 0 4 -Famoxadone 50 + 50 100 Compound 2 0 4 • Black mouth 3 Ronyl 50 + 100 100 Chemical base 2 0 4 -Fosetil 50 + 1600 100 Chemical base £ 0 4 • Compound 2 0 0 0 50 + 50 100 Compound 3 0 9 'Metalaxyl 50 + 50 94 Compound 3 0 9 Azoxys 卜 Robin 50- + 50 100 Compound 3 0 9 Simoxanyl 50 + 100 100 Chemical product 3 0 9 'Famoxadone 50 + 50 100 Compound 3 0 9. Black mouth Ronyl B0 + 100 100 Chemical product 3 0 9 Fosetyl 50 + 1600 100 Compound 3 0 9 Compound 2 0 0 0 50- «0 100 Compound 4 4 9 Metalaxyl 50 + 50 100 Compound 4 9 Aloxis robin 50 + 50 100 Compound 4 4 9 Simoxanyl B 0 + 100 100 Compound 4 4 9 Famoxadone 50- + 60 100 Compound 4 4 9 Black mouth S Ronyl 50 + 100 100 Compound 4 4 9 Fosetyl 50 + 1600 100 Compound 4 4 9 Compound 2 0 0 0 100 Compound 6 8 2 Metalaxyl 50 + 50 100 Compound 6 8 2 Taxoxys Robin 50 + 50 100 Compound 6 8 2 Simoxanyl 50 + 100 100 Compound 6 8 2 Famoxadone 50 + 50 100 Compound 6 8 2 Chlorothalonyl 50 + 100 100 Compound 5 8 2 Focetyl 50 + 1600 100 Compound 6 8 2 Compound 2 0 0 0 50 + 50 100

(Table 1 3) (Continued) Baboon baboon baboon

Joint base joint joint price

Physical property Physical property supply ¾ 笫 ¾ (ppm) ()

Compound 6 8 -metalaxyl 50 + 50 100

Compound 6 8 • Azoxys Mouth Bottle 50 + E0 100

Compound 6 8 -Simoxanyl 50 + 100 100

Compound 6 8Famoxadone 50 + 50 100

Compound 6 8 Chlorolone Ronyl 50 + 100 100

Compound 6 S-fosetyl 50 + 1600 100

Compound 6 8 Compound 2 D 0 0 50- + 50 100

Compound 7 6 g + metalaxyl 100

Compound 7 6 g + azoxys robin 50 450 100

Compound 7 6 9 + Simoxanyl B0 + 100 100

Compound 7 e Q + Famoxadone 50 0 100

Compound 7 6 9 + chlorothalonil 50 + 100 100

Compound 7 6 9 + fosetyl 50 + 1600 100

7 6 9 + Compound 2 0 0 0 50 450 100

Compound 7 7 2 + Metalaxyl 50 50 100

Compound 7 7 2 + Azoxystrobin 50 0 100

Compound 7 7 2 + Simoxanyl 50 + 100 100

Compound 7 7 2 + Famoxadone 50-¾0 100

Compound 7 7 2 + crotarolonil 50 + 100 100

Compound 7 7 2 + fosetyl 50 + 1600 100

Compound 7 7 2 + Compound 2 0 0 0 50 450 100

'Metalaxyl 50 0 100

• Asoxys Higuchi 50 450 100

Simoxanyl 50 + 100 100

-Famoxadone 50 450 100

Chlorothalonil 50 + 100 100

Josetil 50 + 1600 100

-Compound 2 0 0 0 50 460 100

Compound 9 5 1 Metalaxyl B0-f50 100

Compound 9 5 • Azoxys 卜 Robin 50 450 100

Compound 9 5 1-Simoxanyl 50 + 100 100

Compound 9 5 1 Famoxadone 50 0 100

Compound 9 5 1 Black mouth Ronyl 50 + 100 100

Compound 9 5 1 • Fosetyl 50 + 1600 100

Compound 9 5 1 Compound 2 0 0 0 50-¾0 100

Compound 1 0 6 g + metalaxyl 50 0 100

Compound 1 0 6 g + azoxys robin 50 + 60 100

Compound 1 0 5 g + Simoxanyl 50 + 100 100

Convertible 1 0 6 9 + Famoxadone 50 0 100

Compound 1 0 6 g + chlorothalonil B 0 + 100 100

Chemicalized base 1 0 6 g + fosetyl 50 + 1600 100

Compound 1 0 6 9 Compound 2 0 0 0 50 + 50 100

[Test Example 7]

Cucumber urinomeiga

A sufficient amount of the drug prepared at a predetermined concentration was sprayed on cucumbers (variety: Sagamihanjiro) cultivated in a greenhouse. Seven days after spraying, the leaves were cut out and placed in a plastic cup (diameter: 10 cm, height: 10 cm) together with 10 larvae of the second larvae, and the mortality was examined 4 days later. The results are shown in Table 14. (Table 1 4)

[Test Example 8]

Tests for control of potato aphids and downy mildews

After acupuncture aphids were bred in cucumbers (variety: Sagamihanjiro) cultivated in a greenhouse, a sufficient amount of the drug prepared to a predetermined concentration was sprayed. One day after spraying, a conidial suspension of downy mildew, P seudoperonosporacuben sis) was spray-inoculated. Five days after spraying, the number of aphids parasitic on each cucumber was investigated, and the control value was calculated according to the following formula (1). In addition, after 10 days of spraying, the area occupied by mildew spots per cucumber leaf was investigated according to the following indicators, and the total disease index of each ward was calculated. The control value was calculated according to the formula (2) from the average disease severity consisting of the average. The results are shown in Table 15.

T a: Number of parasites after spraying in the treatment area

T b: Number of parasites before spraying in the treatment area

C a: Number of parasites after spraying in the untreated area

C b: Number of parasites before spraying in the untreated area

Formula (1) Control rate = 1 00— {(T a X C b) / (T b X C a)} X 1 00 Disease index 0: No disease

1: The lesion area rate is less than 5%

2: The lesion area rate is less than 5-25%

3: The lesion area rate is 25 to less than 50%

4: The lesion area rate is 50% or more

Formula (2) Control value (%) = (1 Disease severity in one treatment group No disease treatment) XI 0

(Table 15)

With

Wa Aphids

Donation prevention

(ppm) ffi dead insects ^ (%)

(%)

Compound 309 50 92 0

Compound 7 69 50 95 0

Compound 7 2 50 97 0

Compound 951 50 94 0

Compound 1 069 50 94 0

Fenprous 100 0 92

Dinotefuran 100 0 98

Compound 309 + Kafenprox 50 + 100 95 94

Compound 309 + dinotefuran 50 + 100 95 100

Compound 769 + phenfenox 50 + 100 100 96

Compound 769 + dinotefuran 50 + 100 100 100

Compound 772 + Kaffeine Phlox 50 + 100 100 94

Compound 77 2 + dinotefuran 50 + 100 100 100

Compound 951 + phenfenox 50 + 100 100 96

Compound 951 + dinotefuran 50 + 100 98 100

Compound 1 069 + Kafenflox 50 + 100 100 96

Compound 1 069 + dinotefuran B0 + 100 100 100

[Test Example 9]

Rice blast control trial

Rice (variety: Koshihikari; 50 plants) was planted in plastic pots with a diameter of 6 cm in a greenhouse and grown until the 4th leaf developed. After the chemical solution diluted to the prescribed concentration is thoroughly sprayed on the foliage and dried, the solution is transferred to a wet room at 25 ° C (12-hour light-dark cycle), and the conidia of rice blast fungus Py riculariaoryzae) The suspension was spray inoculated. Ten days after the inoculation, the number of lesions in the entire pot was examined, and the control value was calculated using the following formula. The results are shown in Table 16.

Control value (%) = (1 No. of lesions in one treatment group No. of lesions in no treatment group) X 1 0 0

(Table 1 6 Anti-glare test sample ^ ffl

(ppm) (%) Compound 4 7 50

Compound 1 4 8 50

Baboon baboon cradle 3 g 7 50

Compound stand combination compound 2 0 0 2 BO

Compound material property material 2 0 0 3 50

Compound 24 44 444 0 0 4 50

Compound 2 0 0 5 50

Compound 2 0 0 6 50

Compound 2 0 0 7 BO

Compound 2 □ 0 2 100 Compound 2 □ 0 3 100 Compound 2 0 0 4 100 Compound 2 0 0 5 100 Compound 2 0 0 6 100 Compound 2 0 0 7 100 Compound 1 4 8 + Compound 2 0 0 £ 100 Compound 1 4 8 + Compound 2 0 0 3 100 Compound 1 4 8 + Compound 2 0 0 4 100 Compound 1 4 8 + Compound 2 Q 0 5 100 Compound 1 4 δ + Compound 2 0 0 6 555 555 555 55 555 5 555 100 Compound 1 4 8 + Compound 2 0 0 7 ο ο ο ο ooooo ο o ο ο ο ο ο ο 100

^^^ ^ o o o o o o ο ο ο ο ο ο ο ο ο ο ο ο

Compound 3 9 7 + Compound 2 0 □ 2 100 Compound 3 9 7 + Compound 2 0 0 3 100 Compound 3 Q 7 + Compound 2 0 0 4 369999299 100 Compound 3 9 7 + Compound 2 □ 0 5 18 0554468800 Compound 3 9 7 + Compound 2 0 0 6 100 Compound 3 Θ 7 + Compound 2 0 □ 7 100

Claims

The scope of the claims

1. General formula (1)

(Chemical 1) ( ¹⁾

[Wherein R 1 is an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, or 2 to 6 carbon atoms. An arylenoyl group, an aryl group, a heterocycle, an arylalkyl group having 1 to 6 carbon atoms, or a heteroalkyl group having 1 to 6 carbon atoms in the alkyl group,

R 3 and R 4 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloanolalkyl group having 3 to 6 carbon atoms, an anoalkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, An alkyl group having 2 to 6 carbon atoms, an aryl group, a heterocycle, an aryl alkyl group having 1 to 6 carbon atoms in the alkyl group, or a heterocyclic alkyl group having 1 to 6 carbon atoms in the alkyl group; R 3 and R 4 may be bonded to each other to form a hydrocarbon ring having 3 to 6 carbon atoms,

R 6, R 7, R 8 and R 9 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or the number of carbon atoms. A cycloalkenyl group having 3 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, and at least one substituent is an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and 2 to An alkenyl group having 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, and an alkynyl group having 2 to 6 carbon atoms,

R 10 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkenyl group having 3 to 6 carbon atoms, carbon Represents an alkynyl group or a acyl group of 2 to 6, and A represents an oxygen atom or a sulfur atom.

Q i represents an aryl group or a hetero ring. ]

A pest control composition comprising: a diamine derivative represented by formula (1); and one or more compounds selected from the group consisting of other fungicides, insecticides, and acaricides as active ingredients.

2. In the pest control composition according to claim 1,

In the general formula (1), at least one of R 3 and R 4 is an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or 3 to 3 carbon atoms. A cycloalkenyl group having 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, an aryl group or a heterocyclic ring, an aryl group having 1 to 6 carbon atoms in an alkyl group, or an alkyl group having 1 to 6 carbon atoms. A pest control composition which represents a telocyclic alkyl group or R 3 and R 4 are bonded to each other to form a hydrocarbon ring having 3 to 6 carbon atoms.

3 · In the pest control composition according to claim 2,

A pest control composition in which R 2, R 5, and R 10 are hydrogen atoms in the general formula (1).

4. In the pest control composition according to any one of claims 1 to 3,

The other fungicides, insecticides, and acaricides are triazimephone, hexaconazole, propiconazonole, ipconazonore, prochloraz, trinole mizonole, tebuco nazonore, epoxyconazonore, difuenoconazonole, funosila Zonole, Triadimenol, Cyproconazole, Metoconazole, Fluquinconazole, Vitel Thanol, Tetraconazole, Triticonazole, Flutriafol, Penco Nazonole, Diniconazonore, Fenbuconazonole, Bromuconazonore, Imeven Conazonore , Simeconazonole, Microbutanol, Himexazole, Imazalil, Frametopil, Tifluzamide, Etridiazole, Oxispoconazole, Oxispoconazolinolemanoleate Azole fungicides such as pefrazoate, prothioconazolinole, pyrimidine fungicides such as pyriphenox, fenarimol, nuarimol, buprimate, ananilinopyrimidine fungicides such as mepanipyrim, cyprodinil, pyrimethanil, diflumetrime, metalaxyl Benaximi such as Metalaxyl M, Oxa Dixyl, Benaxalil and other acylylalanine fungicides, Thiophanetomethyl, Benominole, Power Norebendazim-Fuberida Zonole, Thiabendazonore Dazol fungicides, Manzeb, Provineb, Dinebu, Methylam, Mannebu, Dilam, Thiuram, Ambum, Polycarbamate, Thiadiazine, and other organic sulfur fungicides, Organochlorine fungicides such as Tetrachrome mouth isophthalonitryl Carboxam fungicides such as ethaboxam, oxycanolevoxin, carboxin, flutolanil, synoletioffam, meproninole, boscalid, dimethomorph, fenprovidin, fenpropimonolev, spiroxamine, tridemonolev, dodemonolev, donomonolev Morpholine fungicides, Azoxys trobin, Cresoxime methyl, Metmino strobin, Lisa strobin, Funolex strobin, Triflix strobin, Dimoxys trobin, Pyracro Torobin, picoxys, etc. Still Birlin fungicides such as diplodione, Procymidone, Vinclozolin, Clozoline, etc. Dicarboximide fungicides, Fursulfamide, Dazomet, Methyl isothiocyanate, Chronolevulin , Metasulfonolev, Hydroxyisoxazone, Hydroxyisoxazol-norecarium, Ecomezonere, D—D, Carbum, Methyl iodide and other soil fungicides, Basic copper chloride, Basic copper sulfate, Nonylfunino Copper sulfonate, oxine copper, DBEDC, anhydrous copper sulfate, copper sulfate pentahydrate, hydroxide copper-based disinfectant such as nickel copper, inorganic sulfur, hydrated sulfur agent, lime sulfur mixture, zinc sulfate, fetin, Inorganic fungicides such as sodium hydrogen carbonate, potassium hydrogen carbonate, hypochlorite, metallic silver, Organic phosphorus fungicides such as edifenphos, Torque mouth phosmethyl, fosetyl, iprobenphos, dinocap, pyrazophos, carbyne, fusalide, tricyclazonore, pyroxylone, diclocimet, phenoxanil and other melanin biosynthesis inhibitors Agents, kasugamycin, validamycin, polyoxin derivatives, blasticidin S, tech mouth phthalam, oxytetracycline, mildiomycin, streptomycin and other antibiotic fungicides, rapeseed oil, machine oil and other natural product fungicides, bench Carbamate fungicides such as avaricarb isopropyl, iprovaricarb, propamocarb, and dietofencarb, pyrrole fungicides such as fluoride, fluoxonil, and fenpiclonil, probenazo , Plant activators that induce plant disease resistance such as cybenzoral S-methyl and thiazinyl, quinolinic fungicides such as quinoxyphene and oxolucic acid, sifenofenamide, fenhexamide, metrafenone, pico Benzamide, Proquinazide, Famoxadone, Ciazoamide, Fuenamidone, Zoxamide, Chlorotalonyl, Simoxanyl, Quabutane, Dithianon, Fluazinam, Folfette, Diclofluanide, Triphorine, Isoprothiolane, Diclomezone Gin, Pencyclon, Quinomethionate, Imoctadine Acetate, Imoctadine Arbesylate, Guazatine, Chloroneb, Organonickel, Dodine, Quintzen, Nylephroleanide, Vanilladine, Nitrotarisopropyl, Phenitropane, Dichlorane, DP C, Dimethylyl monole, Benazol, Funoremet bar, Mandepropoxide, (R —N— [2— (1,3-Dimethylbutyl) thiophene 3-yl] 1-1-methyl-1-3-trifluoromethyl- 1 H —Pirazo Iru 4 1 Carboxamide, general formula (2) _:

(Chemical 2)

A compound represented by the general formula (3)

(Chemical 3)

-The general formula (4):

(Chemical 4)

A compound represented by the general formula (5):

(Chemical 5)

R11 (5)

[Wherein R 11 represents an alkyl group having 1 to 6 carbon atoms, an alkyl group having 2 to 6 carbon atoms, a reel alkyl group or a heterocyclic alkyl group, and R 12 and R 17 represent Each represents a hydrogen atom, R 1 3 and R 14 are each independently a hydrogen atom, carbon number :! Represents an alkyl group of ˜6, R 15 and R 16 each represent a hydrogen atom, and R 18 represents an aryl group or a heterocyclic ring. ] Or a compound represented by the general formula (6

(Chemical 6

[Wherein R 19 is an alkyl group having 1 to 6 carbon atoms substituted with halogen, a cycloalkyl group having 3 to 6 carbon atoms substituted with halogen, or an alkenyl having 2 to 6 carbon atoms substituted with halogen. R 2 0 and R 2 5 each represent a hydrogen atom, R 2 1 and R 2 2 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, R 2 3 and R 2 4 represents a hydrogen atom, and R 2 6 represents an aryl group or a hetero ring. ] A compound represented by

Areslin, Tetramethrin, Resmethrin, Phenotrin, Frametrin, Penoremethrin, Cypermethrin, Denormethrin, Cyhalothrin, Sifnoretrin, Fenprono. Torin, Traloline, Shikuguchi Protoline, Full Citrinate, Full Variaine 卜, Acrinatrine, Teflutriin, Bifentrin, Empentrin, Beta Cyphino Resin, Fenno Relate, Esphenno Pyrethroid insecticides such as relate, funolebrocitrinate, methonoreslin, profluthrin, dimefluthrin, silafunorephene, insecticide chrysanthemum extract, etofenprox, rhino, rufenprox, DDVP, cyanofos, fenthion, feminine small mouth ON, Tetrachlorvinphos, Dimethylvinphos, Propafos, Methylparathion, Temefos, Hoxime, Acepheto, Isophenfos, Salicion, DEP, EPN, Ethion, Mecarbam, Pyridafenthion, Da Iazinone, Pirimiphosmethyl, Etrimphos, Isoxathion, Quinalfos, Chlorpyrifosmethyl, Chlorpyrifos, Josaron, Phosmet, Methidathione, Oxidebum Phosphine, Nomidion, Malathion, Fentate, Dimethoate, Formothione Thiometone, ethinoretiomethone, holate, tenolebufos, profenofos, prothiofos, snoreprofos, pyracrofos, monocrotofos, naredo, phostiase ginseng, triclo / lehon, etoprofos, kazusafos, chronofenvinhos, diclofentoon Metamidhos, Diclonorevos, Tebupyrimfos, Ometoate, Triazofos, Oxidemeton 1 Methyl, Azinhos 1 Metinore, Chronoletoxifos, Diclotofos, Disunolefotone, Fuenamifos, Phosphamidone, Chlormefos, Demetone S— Organophosphorus insecticides such as mevinphos, parathion, NAC, MTMC, MIPC, BPMC, XMC, PHC, MPMC, etiofencalp, vendariocalp, pirimika , Carbosulfane, benfracanoleb, mesomil, oxaminore, aldicarp, chioji force noreb, aranikanoleb, force / repofuran, metiocanoleb, fenotiocanoleb, honolemethanate, xylinoremethinorecanolose Power-bamate insecticides, imidacloprid, nitenbiram, acetamiprid, dinotefuran, thiamethoxam, thiacloprid, neonicotinoid insecticides such as clothiazine, bromopropyrate, dicophore, endosulfan, lindane, etc. Chlorine insecticides, difluvenslon, chlorfluzuron, tefruvenslon, trifunolemron, funolefenoxuron, funolecycloxuron, hexafnoremulon, funolea Insect growth regulators such as Ron, difenthiuron, nonorelon, nobifremolem, bistrifluron, chromafenozide, norofenozide, methoxifenozide, rufenuron, cyromazine, triazamate, nicotine sulfate, polynaguctin complex , Milbemectin, Lepimectin, BT (Bacillus thuringi ens is), Spinosad, Rotenone and other natural product insecticides, Cartap, Ciocyclam, Benzenoletap, Pimetrozine, Fiproninole, Buprofezin, Phenoxycarp, Pyri Proxyfen, methoprene, hyde mouthplane, quinoprene, endosulfan, triazuron, tebufenozide, benzophepine, emamectin, emamectin benzoate, flupirazophos, furakuri Pyrim, flufenzine, indoxacarp, tolfenvirad, gamma cyhalothrin, echpromonore, acetopromonore, amidofnoremet, chronolefenavir, floni forcemide, furphenerim, pyridalyl, sodium oleate Um, potassium oleate, azadeiractin, carbam, carbamnatrium, propargite, azocyclotin, benzoximate, metaaldehyde, protofenfen boot, pencant thiaz, flubenamide, metaflumizole, general formula (7):

(Chemical 7)

[Wherein R 2 7 represents a methyl group or a chloro group, R 28 represents a methyl group, a chloro group, a bromo group or a cyano group, and R 29 represents a chloro group, a bromo group, a trifluoromethyl group or a cyanomethoxy group. R 30 represents a methyl group or an isopropyl group. ] A compound represented by the general formula (8):

(Chemical 8)

[Wherein R 3 1 represents 1, 1, 1, 2, 3, 3, 3-heptafluoro-2-propyl group or 1, 1, 2, 2, 3, 3, 3-heptafluor mouth-1 monopropyl group. To express . ] A compound represented by the general formula (9):

(Chemical 9 [In the formula, is a hydrogen atom or a fluorine atom, R 3 2 and R 3 3 are a hydrogen atom and an alkyl group having 1 to 4 carbon atoms, respectively, and Q ₂ is a phenyl group, a halogen atom, or a carbon atom. An alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, a haloalkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms, and 2 carbon atoms -4 haloalkynyl group, cycloalkyl group having 3 to 6 carbon atoms, halocycloalkyl group having 3 to 6 carbon atoms, alkoxy group having 1 to 3 carbon atoms, haloalkoxy group having 1 to 3 carbon atoms, carbon number: ! C 1-3 alkylthio group, C 1-3 alkyl thio group, C 1-3 alkylsulfinyl group, C 1-3 alkyl sulfinyl group, C 1-3 alkylsulfonyl group, carbon A haloalkylsulfonyl group having 1 to 3 carbon atoms, an alkylamino group having 1 to 4 carbon atoms, a dialkylamino group having 1 to 4 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an alkylcarbonyl group having 1 to 4 carbon atoms, carbon number;! A substituted phenyl group having one or more substituents, which may be the same or different, selected from an alkyl group having 1 to 4 alkylpowers, a ruponinoreoxy group, an alkoxycarbonyl group having 1 to 4 carbon atoms, an acetylamino group, and a phenyl group; or , A halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an arnolekenyl group having 2 to 4 carbon atoms, a haloanolekenyl group having 2 to 4 carbon atoms, and an alkynyl group having 2 to 4 carbon atoms A haloalkynyl group having 2 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a halocycloalkenyl group having 3 to 6 carbon atoms, and a carbon number! ~ 3 alkoxy groups, carbon number :! -3 haloalkoxy groups, 1 to 3 alkylthio groups, 1 to 3 haloalkylthio groups, 1 to 3 alkylsulfinyl groups, 1 to 3 haloanolalkylsulfier groups, carbon Alkyl sulfonyl group having 1 to 3 carbon atoms, haloalkyl sulfonyl group having 1 to 3 carbon atoms, alkyl amino group having 1 to 4 carbon atoms, dialkylamino group having 1 to 4 carbon atoms, cyano group, nitro group, hydroxy group 1 selected from an alkylcarbonyl group having 1 to 4 carbon atoms, an alkyl carbonyloxy group having 1 to 4 carbon atoms, an aralkoxycarbonyl group having 1 to 4 carbon atoms, an acetylamino group, and a phenyl group. Q ₃ is a pyridyl group having the same or different substituents as described above, and Q ₃ is represented by the general formula (A)

(Chemical 1 0) (Wherein, Υι, Υ ₅ may be the same or different, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, 1 to 4 carbon atoms ˜4 haloalkoxy groups, 1 to 3 alkylthio groups, 1 to 3 haloalkylthio groups, 1 to 3 alkylsulfinyl groups, 1 to 3 haloalkylsulfier groups, 1 carbon atom Represents an alkylsulfonyl group having _{3 to 3} carbon atoms, a haloanolalkylsulfonyl group having 1 to 3 carbon atoms, and a cyano group, and ₃ represents a perfluoroalkyl group having 2 to 6 carbon atoms and a perfluorocarbon having 1 to 6 carbon atoms. An alkylthio group, a perfluoroalkylsulfinyl group having 1 to 6 carbon atoms, a perfluoroalkylsulfonyl group having 1 to 6 carbon atoms, Υ ₂ and Υ ₄ are hydrogen atoms, halogen atoms, and carbon atoms 1 to 4 Represents an alkyl group.) It is represented by ] Or a compound represented by the general formula (10)

(Chemical 1)

Wherein the chi ₂ is a hydrogen atom or a fluorine atom, R35, R36 are each a hydrogen atom, an alkyl group having 1 to carbon atoms 4, R34 is alkyl Le group having 1 to 6 carbon atoms, carbon atoms 1 to 6 haloalkyl groups, 2 to 6 carbon atoms alkenyl groups, 2 to 6 carbon atoms haloalkenyl groups, 2 to 6 carbon atoms alkynyl groups, 2 to 6 carbon atoms haloalkynyl groups, 3 to 8 carbon atoms A cycloalkyl group having 3 to 8 carbon atoms, one — Zi— R37 (where Ei is an alkylene group having 1 to 4 carbon atoms, an alkenylene group having 2 to 4 carbon atoms, 3 to 3 carbon atoms) An alkynylene group having 4 carbon atoms: a haloalkylene group having 4 to 4 carbon atoms, a haloalkenylene group having 2 to 4 carbon atoms, or a haloalkylene group having 3 to 4 carbon atoms, R37 being a hydrogen atom, having 1 to 6 carbon atoms An alkyl group, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, Haloalkyl prime 1-6, haloalkenyl of 2 to 6 carbon atoms, shows a haloalkynyl group 2-6 carbon atoms, Zi is -0-, One S-, one SO-, -S0 ₂ - one C (= 0) —, one C (= 0) 0—, -0C (= 0) one, -N (R38)-, — C (= 0) N (R38) —, -N (R38) C ( = 0) One (R38 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkylcarbohydrate having 1 to 4 carbon atoms) A haloalkylcarbonyl group having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon atoms. ) ), -E ₂ -R 3 9 (wherein E ₂ is an alkylene group having 1 to 4 carbon atoms, an alkenylene group having 2 to 4 carbon atoms, an alkynylene group having 3 to 4 carbon atoms, or 1 to carbon atoms) A haloalkylene group having 4 to 4 carbon atoms, a haloalkenylene group having 2 to 4 carbon atoms, a haloalkynylene group having 3 to 4 carbon atoms, R 3 9 is a cycloalkyl group having 3 to 8 carbon atoms, and a halocyclocarbon having 3 to 8 carbon atoms. An alkyl group, a cyano group, a nitro group, a hydroxy group, a phenyl group, or the same or different, a halogen atom, an alkylene group having 1 to 6 carbon atoms, a haloanolyl group having 1 to 6 carbon atoms, or a carbon number :! ~ 6 anoalkoxy group, C 1-6 haloalkoxy group, C 1-6 alkylthio group, C 1-6 haloalkylthio group, C 1-6 alkyl sulrefiel group, carbon number 1-6 noroanorequinoles norefier groups, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, Cyano group, nitro group, hydroxyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbonyl group, carbon A C 1-4 alkyl group, a alkoxy group having 1 to 4 carbon atoms, a C 1-4 alkoxy group, a substituted phenyl group having one or more substituents selected from a sulfonyl group, a pyridyl group, or a halogen atom, or a haloalkyl having 1 to 6 carbon atoms. Q4 represents a general formula (B), and represents a substituted pyridyl group having one or more substituents selected from a alkoxy group having 1 to 6 carbon atoms, a phenyl group, a phenyl group, and a tetrahydrofuran group. :

(Chemical 1 2)

(In the formula, Y ₆ , may be the same or different, and are a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or 1 carbon atom. -4 haloalkoxy groups, C1-C3 alkylthio groups, C1-C3 haloalkylthio groups, C1-C3 alkylsulfinyl groups, C1-C3 nochole alkyl sulfiel groups, carbon Represents an alkylsulphonyl group having 1 to 3 carbon atoms, a haloalkylsulfonyl group having 1 to 3 carbon atoms, and a cyano group, and Y ₈ is a perfluoroalkyl group having 2 to 6 carbon atoms, and a perfluoro having 1 to 6 carbon atoms. O-alkylthio group, carbon number 1 to 6 perfluoroalkyl sinorefinino groups, 1 to 6 carbon atoms. 1 represents a fluoroalkylsulfonyl group, Y ₇ and Υ ₉ represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 4 carbon atoms. ) ] A compound represented by

Chronovengerate, Phenisobromolate, Tetradiphone, CPCB S (Chlorfenson), BPPS, Quinomethionate, Amitraz, Benzomate, Hexithiazotas, Fenbutazin oxide, Cihexatin, Dienochlor, Clofentezine, Pyridaben, Fenpyrazine, Fenpyrazate A pest control composition which is one or more compounds selected from tebufenpyrad, pyrimidifene, acequinosyl, bifenazate, etoxazole, spiro diclofen, spinomesifen, amidflumet and difluvidazine.

5. In the pest control composition according to any one of claims 1 to 3,

Other fungicides, insecticides, and acaricides are metalaxyl, metalaxyl-M, oxadixil, benalaxyl, manzeb, provineb, ginebu, methylam, mannebu, polycarbamate, thiadiazine, (RS) —N— [2— (1 , 3—Dimethylbutyl) thiophene 3-yl] — 1—Methyl-1 3-Trifluoromethinole 1 H—Villazoru 4—Carboxamide, ethaboxam, dimethomorph, azoxis trobin, cresoxime methyl , Pyraclostrobin, fursulfamide, basic copper chloride, basic copper sulfate, copper nonylphenol sulfonate, copper oxine, DB EDC, anhydrous copper sulfate, copper sulfate pentahydrate, cupric hydroxide, fosetyl, sto Leptomycin, Ventavaricanolebu isopropinore, iprono licanolev, propamocanoleb Furuozore Lee Mi-de, Famokisa Don, Shiazofua Mi de, Fuenami Don, Zokisami de, black hole Taroninore, Shimokisani ^^, Kiyabutan, dithianon, Funoreajinamu, Fuorupe' DOO, Mandy prop Mi de formula (3):

(Chemical 1 3)

A compound represented by the general formula (4)

(Chemical 1 4)

A compound represented by the general formula (5)

(Chemical 15)

[Wherein R 11 represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an arylalkyl group or a heterocyclic alkyl group, and R 12 and R 17 are each represented by Represents a hydrogen atom, R 1 3 and R 14 each independently represent a hydrogen atom, a carbon number;! To 6 alkyl groups, R 15 and R 16 each represent a hydrogen atom, and R 18 represents Represents an aryl group or a heterocycle. ] Or a compound represented by the general formula (6):

(Chemical 16) (6)

[Wherein R 19 is an alkyl group having 1 to 6 carbon atoms substituted with halogen, an alkyl group having 3 to 6 carbon atoms substituted with halogen, or an alkyl group having 2 to 6 carbon atoms substituted with halogen. R 2 0 and R 2 5 each represent a hydrogen atom, R 2 1 and R 2 2 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, R 2 3 and R 2 4 represents a hydrogen atom, and R 2 6 represents an aryl group or a heterocyclic ring. ] A compound represented by, etofenprox, dinotefuran, general formula (9):

(Chemical 17)

[Wherein, X i is a hydrogen atom or a fluorine atom, R 3 2 and R 3 3 are a hydrogen atom and an alkyl group having 1 to 4 carbon atoms, respectively, and Q ₂ is a phenyl group or a norogen. Atoms, alkyl groups having 1 to 4 carbon atoms, haloalkyl groups having 1 to 4 carbon atoms, alkenyl groups having 2 to 4 carbon atoms, haloalkenyl groups having 2 to 4 carbon atoms, alkynyl groups having 2 to 4 carbon atoms, carbon A haloalkynyl group having 2 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a halocycloalkyl group having 3 to 6 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a carbon number:! To a haloalkoxy group having 3 to 3 carbon atoms :! ~ 3 alkylthio groups, carbon number :! ~ 3 halo anolyl thio group, carbon number :! ~ 3 alkyl sulfier groups, carbon number :! ~ 3 haloanorequinoles norefinyl group, carbon number :! ~ 3 alkylsulfonyl group, 1 ~ 3 carbon alkylsulfonyl group, carbon number :! ~ 4 anolequinolemino group, 1 to 4 carbon dialkylamino group, cyano group, nitro group, hydroxyl group, 1 to 4 carbonyl carbonyl group, carbon number! An alkylcarbonyloxy group of ˜4, an alkoxycarbonyl group of 1 to 4 carbon atoms, an acetylamino group, a substituted phenyl group having one or more substituents which may be the same or different and selected from the benzyl group, pyridyl Group, or halogen atom, alkyl group having 1 to 4 carbon atoms, alkyl group having 1 to 4 carbon atoms, alkenyl group having 2 to 4 carbon atoms, haloalkenyl group having 2 to 4 carbon atoms, carbon number 2 -4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkenyl group, C3-C6 halochloroalkyl group, C1-C3 alkoxy group, C1-C3 Haloalkoxy group, alkylthio group having 1 to 3 carbon atoms, haloalkylthio group having 1 to 3 carbon atoms, ananolylsulfinyl group having 1 to 3 carbon atoms, carbon number :! ~ 3 haloalkylsulfinole group, 1 ~ 3 alkylsulfonyl group, carbon number :! Haloalkylsulfonyl group of 3 to 3, alkylamino group of 1 to 4 carbon atoms, dialkylamino group of 1 to 4 carbon atoms, cyano group, nitro group, hydroxy group, alkylcarbonyl group of 1 to 4 carbon atoms, carbon An alkylcarbonyl group having 1 to 4 carbon atoms, an alkoxycarbonyl group having 1 to 4 carbon atoms, an acetylamino group, A pyridyl group having one or more substituents which may be the same or different and selected from the nyl group, and Q ₃ is represented by the general formula (A):

(Chemical 1 8)

(Wherein, Υι, Υ ₅ may be the same or different, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, 1 to 4 carbon atoms -4 haloalkoxy groups, 1 to 3 alkylthio groups, 1 to 3 haloalkylthio groups, 1 to 3 alkylsulfinyl groups, 1 to 3 haloalkylsulfinyl groups, 1 to 3 carbon atoms 3 alkylsulfonyl group, a halo alkylsulfonyl group having a carbon number of 1-3, shows the Shiano group, Upsilon ₃ par full O b alkyl group having 2 to 6 carbon atoms, per full O b alkylthio group having 1 to 6 carbon atoms, Carbon number: represents a perfluoroalkylsulfinyl group having a carbon number of 1 to 6, a perfluoroalkylsulfonyl group having a carbon number of 1 to 6, and Υ ₂ and Υ ₄ are a hydrogen atom, a halogen atom, and an alkyl group of 1 to 4 carbon atoms. Show.) It is represented by ] Or a compound represented by the general formula (1 0)

(Chemical 1)

[In the formula, Χ2 is a hydrogen atom or a fluorine atom, R35 and R36 are a hydrogen atom and an alkyl group having 1 to 4 carbon atoms, respectively, and R34 is an alkyl group having 1 to 6 carbon atoms and a carbon number. 1 to 6 haloalkyl groups, 2 to 6 carbon atoms alkenyl groups, 2 to 6 carbon atoms haloalkenyl groups, 2 to 6 carbon atoms alkynyl groups, 2 to 6 carbon atoms haloalkynyl groups, 3 to 8 carbon atoms A cycloalkyl group having 3 to 8 carbon atoms, — R3 7 (wherein is an alkylene group having 1 to 4 carbon atoms, 2 carbon atoms) An alkenylene group having 4 to 4 carbon atoms, an alkynylene group having 3 to 4 carbon atoms, a haloalkylene group having 1 to 4 carbon atoms, a haloalkenylene group having 2 to 4 carbon atoms, and a haloalkynylene group having 3 to 4 carbon atoms, R 3 7 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a haloanoleyl group having 1 to 6 carbon atoms, or a halo having 2 to 6 carbon atoms. An alkenyl group, a haloalkynyl group having 2 to 6 carbon atoms, τ is —0—, — S—, — SO—, one S0 ₂ —, — C (= 0) —, — C (= 0) 0 _ ,-0C (= 0) ―, 1 N (R 3 8) 1, 1 C (= 0) N (R 3 8) —, 1 N (R 3 8) C (= 0)-(R 3 8 is It represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkylcarbonyl group having 1 to 4 carbon atoms, a haloanolalkylcarbonyl group having 1 to 4 carbon atoms, and an aralkoxy group carbonyl group having 1 to 4 carbon atoms. ) ), -E ₂ -R 3 9 (wherein E ₂ is an alkylene group having 1 to 4 carbon atoms, an alkenylene group having 2 to 4 carbon atoms, an alkynylene group having 3 to 4 carbon atoms, or a carbon number of 1 to A haloalkylene group having 4 carbon atoms, a haloalkenylene group having 2 to 4 carbon atoms, a haloalkynylene group having 3 to 4 carbon atoms, R 3 9 is a cycloalkyl group having 3 to 8 carbon atoms, and a halocyclocarbon having 3 to 8 carbon atoms. An alkyl group, a cyano group, a nitro group, a hydroxy group, a phenyl group, or the same or different, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having! Number:! ~ 6 alkoxy group, C 1-6 haloalkoxy group, C 1-6 alkylthio group, C:! ~ 6 halo anorequinolethio group, C 1-6 alkyl snore Fier group, carbon number:! ~ 6 alkylsnorefinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloanolalkylsulfonyl group, Cyano group, nitro group, hydroxyl group, C1-C4 alkylcarbonyl group, C1-C4 haloalkylcarbo Diethyl group, carbon number:! ~ 4 alkylcarbonyloxy group, C1-C4 alkoxy carbonyl group, one or more substituted phenyl group, pyridyl group, halogen atom, carbon Q ₄ represents a haloalkyl group having 1 to 6 carbon atoms, a substituted pyridyl group having one or more substituents selected from a haloalkoxy group having 1 to 6 carbon atoms, a phenyl group, and a tetrahydrofuran group. General formula (B):

(Chemical 20)

(In the formula, 、 ₆ , may be the same or different, and are a halogen atom, an aralkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an aralkoxy group having 1 to 4 carbon atoms, or 1 carbon atom. A haloalkoxy group having 4 to 4 carbon atoms, an alkylthio group having 1 to 3 carbon atoms, a haloalkylthio group having 1 to 3 carbon atoms, an alkylsulfinyl group having 1 to 3 carbon atoms, an alkylsulfininole group having 1 to 3 carbon atoms, alkynyl Norre sulfonyl group 1-3 carbon atoms, haloalkylsulfonyl group having a carbon number of 1-3, shows the Shiano group, Upsilon ₈ is Pas one Furuoroarukiru group having 2 to 6 carbon atoms, Pafuruoro carbon number 1-6 An alkylthio group, a perfluoroalkylsulfinyl group having 1 to 6 carbon atoms, a perfluoroalkylsulfonyl group having 1 to 6 carbon atoms, and Υ ₇ and Υ ₉ are a hydrogen atom, a halogen atom, and a carbon number 1 to 4 alkyl Represented by the shown.). ] The pest control composition which is 1 or more types selected from the compound represented by these.