WO2001087857A1 - Phenyloxazole compounds and fungicides for agricultural and horticultural use - Google Patents

Abstract

Phenyloxazole compounds of the general formula (1) or salts thereof, which can be synthesized with industrial advantage and are useful as fungicides for agricultural and horticultural use exhibiting excellent fungicidal effects not only on pathogenic fungi sensitive to fungicides of the prior art but also on those resistant thereto wherein X is halogeno, nitro, cyano, C1-6 alkyl, or the like; Y is halogeno, cyano, nitro, C1-12 alkyl, or the like; Z is O, S, SO, SO2, or N-R2; R1 is hydrogen, C1-6 alkyl, C3-7 cycloalkyl, or the like; R2 is hydrogen or C1-6 alkyl, or R2 together with N-R1 may form a ring; m is an integer of 0 to 2; and n is an integer of 0 to 3.

Description

 Description Phenyloxazole compounds and fungicides for agricultural and horticultural use

 The present invention relates to a novel phenyloxazole compound and a salt thereof, and a fungicide for agricultural and horticultural use containing the compound as an active ingredient. Background technology:

 In recent years, various pathogens have developed resistance to benzimidazole fungicides ゃ dicarboximide fungicides and the like, resulting in insufficient efficacy of these agents, and there is a demand for effective agents for resistant bacteria.

The phenyloxazole compound similar to the compound of the present invention includes a compound represented by the general formula:

(Wherein, X ′ represents 0 or S, RR ³ represents a phenyl group having a substituent, and R ² represents a hydrogen atom, a phenyl group, a halogen atom, etc.). It is described as an oxygen inhibitor. However, compounds in which X ′ is 0 are not specifically described. DISCLOSURE OF THE INVENTION:

INDUSTRIAL APPLICABILITY The present invention contains a funuyloxazole compound which can be synthesized industrially advantageously and has an excellent bactericidal effect not only on pathogenic bacteria sensitive to conventional drugs but also on resistant bacteria, and contains the compound as an active ingredient It is an object of the present invention to provide an agricultural and horticultural fungicide. The present invention provides a compound represented by the general formula (1):

 (1)

(Wherein, X is a halogen atom, a nitro group, Shiano group, an alkyl group, hydroxy group, C -! ₆ alkoxy group, a haloalkoxy group, CM alkylamino group, di C _1-6 § alkylamino group, an alkylthio group, represents a c _1-6 alkylsulfinyl group, a c _1-6 alkylsulfonyl group, a formyl group, or an alkylcarbonyl group,

Y is a halogen atom, Shiano group, a nitro group, c -! ₁₂ alkyl group, c _2-6 alkenyl group, C _2-6 alkynyl group, C ₃ - ₇ cycloalkyl group, an alkoxy group, 0 _1-6 Haroaru Kokishi Group, C _1-6 haloalkyl group, hydroxy C _1-6 alkyl group, alkoxy CM alkyl group, d- ₆ alkoxyalkoxy alkyl group, haloalkoxy

C alkyl group, c _1-6 alkylthio c _1-6 alkyl group, c ₂ _ ₆ Arukiniruokishi c _1-6 § alkyl group, an amino CI- ₆ alkyl group, an alkylamino group, di-c _1-6 alkylamino group , C _1-6 alkylthio group, formyl groups, C alkylcarbonyl group, an alkoxy group, a mono- or di-Ji ^ alkyl substituent force Rubamoiru group, may be substituted by Q ₂ full We carbamoylmethyl group, mono or di-alkyl substituted Chiokaruba moil group, in optionally substituted C doctor ₆ alkyl imino methyl group, a benzyl group which may be substituted by Q _2, a phenyl group which may be substituted by Q _2, or substituted by Q ₂ and heterocyclic group to have a good, halo C ₂ _ ₆ alkenyl group, halo C ₂ _ ₆ alkynyl group, hydroxy § Lal kill group, Shiano alkyl group, an optionally substituted Fuwenokishi alkyl group by Q _2, by Q ₂ Place Are also good Fuweniruchio alkyl group, alkylsulfinyl ds alkyl group, an alkylsulfonyl Ji _1-6 alkyl group, may be substituted by Q ₂ full Enirusuruhoniru C _1-6 alkyl group, a carboxy alkyl group, an alkoxycarbonyl two Le ^ - ₆ alkyl group, an alkyl group substituted with a heterocycle, C _1-6 alkyl group substituted with Okishiran force Rubamoiru alkyl group, a mono- or di-alkyl Substituting power: _6- alkyl group of rubamoyloxy, optionally substituted with Q ₂ X-carbamoyloxy alkyl group, C-alkyl carboxy-d- ₆ alkyl group, C _6- haloalkylcarboxy-d- ₆ alkyl group, C ₂ _ ₆ alkenyl group, halo C _2-6 alkylcarbonyl group, halo C ₂ _ ₆ alkynyl group, an alkoxy ^ - ₆ alkylcarbonyl alkenyl group, C _1-6 alkylthio alkylcarbonyl group, C _2-6 alkynyl Oxy C ₆ alkylcarbonyl group, benzoyl group optionally substituted by Q ₂ , alkoxycarbonylamino group, mono- or di-C _1-6 alkyl-substituent rubamoylamino group, alkoxyiminomethyl group, haloalkoxyminomethyl group , C _2-6 alkenyl O key Consequences Minomechiru group, C _2-6 alkynyl O alkoximinoalkyl amino C _1-6 alkyl group, a halo C ₂ - ₆ alkynyl O key Consequences Minomechiru group, Q may be substituted with _2-phenylene Louis Minomechiru group, a mono- or di-alkylaminoalkyl group, it may be substituted by Q ₂ Ararukiruokishi alkyl group, substituted by Q ₂ even better § la Ruki Ruo key Consequences amino methyl, C ₃ - ₇ cycloalkyl d_ _s alkyl group, alkoxycarbonyl Ci-s alkoxy d ₆ alkyl group, human de Loki Consequences amino methyl, C port C ₂ - ₆ § Luque represents a nil O key Consequences amino methyl, it may be substituted by Q ₂ Ararukiruoki shea alkyl group or an azide substituted alkyl group.

Z is 0, representing S, SO, and S 0 ₂ or N-R _2.

Ri is hydrogen atom, C _1-6 alkyl group, C ₃ _ ₇ cycloalkyl alkyl groups, C _2-6 alkenyl groups, C _2-6 alkynyl group, a haloalkyl group, C ₂ - ₆ haloalkenyl group, C _2-6 Haroaruki group, human Dorokishi C _1-6 alkyl group, an alkoxy _alkyl group, CM alkyl thio alkyl group, may be substituted by Q ₂ Fuwenokishi C _1-6 alkyl group, it may be substituted by Q ₂ phenylene thio alkyl group, C _1-6 alkylsulfinyl CM alkyl group, C - ₆ alkylsulfonyl C _1-6 alkyl group, may be substituted by Q ₂ full Enirusuruhoniru alkyl group, Shiano C - ₆ alkyl group, CM alkylamino C

_1-6 alkyl group, di C physician ₆ alkylamino ₍₆ alkyl group, hydroxycarboxylic carbonyl C _1-s alkyl group, CI- ₆ alkoxycarbonyl _d-6 alkyl group, Okishiraniru 0 ₆ alkyl group, aziridinyl Jiniru. ^ Alkyl group, glycidyloxy c _1-6 alkoxyalkyl group, azetidinoxy d- ₆ alkoxyalkyl group, formyl group, CM alkyl Kill carbonyl group, C ₂ - ₆ alkenyl group, c _1-6 haloalkylcarbonyl group, C ₂ - ₆ haloalkynyl group, C _1-6 alkoxy C _1-6 alkylcarbonyl group, C 6 alkylthio, C ₆ alkylcarbonyl group, C _2-6 Arukiniruokishi C ₆ alkyl force Ruponiru group, may be substituted by Q ₂ Benzoiru group, C _1-6 alkoxycarbonyl group, it may be substituted with C C _1-6 alkyl thiocarbonate group, an alkylsulfonyl group, Q ₂ substituted by with good off We sulfonyl sulfonyl group, a force Rubamoiru group, Q ₂ in which may be substituted Fuweniruchio force Rubamoiru group may be substituted by Q ₂ benzyl group, Q ₂ may be substituted with Fuweniru group, which may be heterocyclic group substituted with Q _2, alkoxy _(s alkoxy group, a mono- or Jijito ₆ alkyl substituted Karubamo I group, Alkylphosphonyl group, an 〇 ₆ alkylcarbonyl two Okishi alkyl group, Amino substituted hydroxyalkyl group, azido substituted hydroxyalkyl Le group or Q ₂ in which may be substituted off carbamoylmethyl group.

R ₂ may represent a hydrogen atom or a C _1-6 alkyl group, or may form a ring together with N—R !.

The above represents a cyano group, a halogen atom, an alkoxy group, an alkylthio group, or a C _1-6 alkoxycarbonyl group.

Q ₂ represents a cyano group, a nitro group, a halogen atom, a C _1-6 alkyl group, a lower alkyl group, an alkoxy group, a C _1-6 alkylthio group or an alkoxycarbonyl group.

 The heterocyclic group is a 5- or 6-membered unsaturated heterocyclic group containing oxygen, sulfur or nitrogen as a phthalo atom.

m represents 0, 1 or 2, and n represents 0 or an integer of 1 to 3. When m and n are 2 or more, X and Y may be the same or different. Further, when m is adjacent two Y 2, C ₄ two Y - ₅ may form an alkylene. Or a salt thereof, and one or more of the compound represented by the general formula (1) or a salt thereof as an active ingredient. Agent.

The present invention relates to a compound represented by the general formula (1) or a salt thereof, and one or a combination thereof. A fungicide for agricultural and horticultural use containing two or more kinds as active ingredients.

In the compound represented by the general formula (1) or a salt thereof (hereinafter, also referred to as “the compound of the present invention”), X is a nitro group; a cyano group; a formyl group; a hydroxy group; fluorine, chlorine, bromine, and iodine. halogen atoms and the like; methyl, Echiru, propyl, isopropyl, Petit Le, sec- heptyl, Isopuchiru, t-heptyl, C _1-6 alkyl group such as pentyl and its isomers, the xylene Le and isomers thereof; main butoxy , Ethoxy, propoxy, isopropoxy, butoxy, sec—butoxy, isobutoxy, t-butoxy, etc .; ₆ alkoxy groups; chloromethoxy, dichloromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy, 1,1-difluoro Haloalkoxy groups such as roethoxy; methylamino, ethylamino, n-propylamino, Sopuro Piruamino, n- Puchiruamino, Isobuchiruamino, sec one Puchiruamino, t-Puchiruami Roh, 1-methyl-Petit Rua amino, C _1-6 Arukirua amino group such as n- Penchiruamino; Jimechiruamino, Jechiruamino, Jipuropiruamino, Jibuchiruami Bruno, E chill isopropyl Di C _1-6 alkylamino groups such as amino and methylpropylamino; C _1-s alkylthio groups such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio and t-butylthio; methyl scan Norre alkylsulfinyl, E chill sulfinyl, propyl sulfinyl, Puchirusurufu C i_ ₆ alkylsulfinyl group such Iniru; methylsulfonyl, Echirusuruhoniru, propylsulfonyl, alkylsulfonyl such Puchirusuruhoniru two A C _1-6 alkyl carbonyl group such as methylcarbonyl, ethylcarbonyl, propizolecarbonyl, and butylcarbonyl.

Y represents a cyano group; a nitro group; a halogen atom such as fluorine, chlorine, bromine, or iodine; methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isoptyl, t-butyl, pentyl and isomers thereof, and hexyl. And C _1-6 alkyl groups such as isomers; ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl- 2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-12-butenyl, 2-methyl-2-butenyl, 1-hexenyl, 2-hexenyl, 3- Hexenyl, 4 one hexenyl, a cyclohexenyl, etc., to 5-C ₂ - ₆ alkenyl group; Echiniru, 1-propynyl, 2 - propynyl, 1-heptynyl, 2-heptynyl, 3 - heptynyl, 1 one methyl one 2-propynyl , 2-Methyl-3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 2-methyl-1-pentynyl, 1-hexynyl, 1,1-dimethyl-2 - C ₂ such heptynyl - ₆ alkynyl; cyclopropyl, Shikuropuchiru, cyclopentyl, key sill cyclohexane, C _3-7 cycloalkyl group heptyl like cyclohexane; main butoxy, ethoxy, propoxy, Isopurobokishi, butoxy, sec - Alkoxy groups such as butoxy, isobutoxy, t-butoxy; chloromethoxy, dichloromethoxy, trichloromethoxy CM haloalkoxy groups such as trifluoromethyloxy, 1-fluoroethoxy and 1,1-difluoroethoxy; chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, trifluoromethyl, trichloromethyl D- ₆ haloalkyl groups such as tyl, trifluoroethyl, and pentafunolemethyl; hydroxyalkyl groups such as hydroxymethyl, 2-hydroxyhexyl, and 3-hydroxypropyl; methoxymethyl, methoxyethyl, ethoxymethyl, and propoxymethyl , C _1-6 alkoxy C _1-6 alkyl group butoxymethyl and the like; main Tokishime Tokishimechiru, main Tokishime Tokishechiru, Etokishime Tokishimechiru, Purobokishime Tokishimechiru, Butokishime Alkoxyalkoxy Cis alkyl groups such as xylmethyl; chloromethoxymethyl, dichloromethoxymethyl, trichloromethoxymethyl, trifluoromethoxymethyl, 1-fluoroethoxymethyl, 1,1-difluoroethoxymethyl, chloromethoxyethyl, chloromethoxyethyl, trifluoromethoxyethyl _{Alkylthioalkyl} groups such as methylthiomethyl, methylthioethyl, ethylthioethyl, ethylthiomethyl, propylthiomethyl, butylthiomethyl, etc .; 2-propynyloxymethyl, 2-butynyl Okishimechiru, 1-methylation - 2-propynyl O carboxymethyl, 2-propynyl O key Chez C chill etc. ₂ - ₆ Arukini Ruokishi CM alkyl group; aminomethyl, Aminoechiru, § Mi _6- alkyl groups such as aminopropyl; methylamino, ethylamino, n-propylamino, isopropyl Ci- ₆ alkylamino groups such as pyramino, n-butylamino, isobutylamino, sec-butylamino, t-butylamino, 1-methylbutylamino, n-pentylamino, etc .; dimethylamino, getylamino, dipropylamino, dibutylamino, ethylisopropylamino, Dithioalkylamino groups such as methylpropylamino; alkylthio groups such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, and t-butylthio; formyl groups; methylcarbonyl, ethylcarbonyl, and propylcarbonyl Ds alkylcarbonyl groups such as butylcarbonyl and butylcarbonyl; methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl , T - C such butoxycarbonyl - ₆ alkoxycarbonyl group;! Q ₂ in which may be substituted Fuwenirukaru Bamoiru group; methylcarbamoyl, dimethylcarbamoyl, E Ji carbamoyl, propyl force Rubamoiru, ₆ alkyl force Rubamoiru group such Puchirukaru Bamoiru ; methylthio force Rubamoiru, substituted with at dimethylthio force Rubamoiru, Echiruchio force Rubamoiru, propylthio force Rubamoiru, C _1-6 alkyl-substituted Chiokarubamoiru groups such Puchiruchio force Rubamoiru, Mechirui Minomechiru, C _1-6 Arukirui Minomechiru group such Echirui Minomechiru is group which may be; heterocyclic group which may be substituted with Q _2;; good off alkylsulfonyl group optionally substituted by Q _2; Q ₂ may benzyl group which may be substituted with a 3 - Furuoro 1 one-propenyl , 4-chloro-2-butenyl, 4,4-dichloro Over 3-butenyl, 4, 4-difluoro-3 - butenyl, 2, 2 - dichloro 2 - halo C _2-6 alkenyl group such as pro Bae two les; 2-Clos port one Echiniru, 3 black port one 1 one pro Halo-C ₂ alkynyl groups such as pinyl, 3-chloro-2-propynyl, 4-chloro-1,1-butynyl, 4,4-dichloro-1-butynyl, 4,4-difluoro-3-butynyl; 2-hydroxybenzyl And hydroxyaralkyl groups such as 3-hydroxybenzyl, 4-hydroxybenzyl, 4-hydroxyphenacyl, and hydroxybenzyl; cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, and 3-cyanopropyl , 1 one Shianopuropiru, Shiano C _1-6 alkyl group such as 4-Shianopuchiru; Fuenokishime chill, 1-safe Enoki Chez chill, 2- Fuenokishechiru, 3-phenoxyethanol propyl, 4 monounsaturated Phenoxy alkyl groups such Nokishibuchiru; phenylene Ruchiomechiru, 2- Phenylthio d-alkyl groups such as phenylthioethyl, 1-phenylthioethyl, 3-phenylthiopropyl, 1-phenylthiopropyl, 1-phenylthiobutyl, and 4-phenylthiobutyl ; Methylsulfinylmethyl, ethylsulfinylmethyl, propylsulfinylmethyl, butylsulfinylmethyl, 1-methylsulfinylethyl, 2-methylsulfinylethyl, 3-methylsulfinylpropyl, 3-ethylsulfinylpropyl, 4-butylsulfinylbutyl, etc. Alkyl sulfinyl alkyl group; methylsulfonylmethyl, ethylsulfonylmethyl, propylsulfonylmethyl, butylsulfonylmethyl, 1-methylsulfonylethyl, 2-methylsulfonylethyl, 3-methylsulfonylpropyl, 3- Ethils le Nirupuropiru, 4 one-heptyl sulfonyl butyl alkylsulfonyl C _1H3 al Kill group; phenylalanine sulfonyl methyl, 1-phenylpropyl sulfonyl E chill, 2-phenylene Le sulfonyl E chill, 3 full We sulfonyl sulfonyl propyl, 4- off _6- alkyl groups such as phenylsulfonylbutyl and the like; carboxyalkyl groups such as carboxymethyl, 1-carboxyl, 2-carboxyethyl, 3-carboxypropyl, and 4-hydroxypropyl; methoxycarbonylmethyl; Alcohols such as ethoxycarbonylmethyl, propoxycarbonylmethyl, butoxycarbonylmethyl, t-butoxycarbonylmethyl, 1-methoxycarbonylethyl, 2-methoxycarbonylethyl, 3-propoxycarbonylpropyl, 4-ethoxycarbonylbutyl, etc. A carbonyl-2-alkyl group; an alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, etc. substituted with (heterocycle or oxysilane); 1-propenylcarbonyl, -1-Bed Saturation ylcarbonyl etc. C ₂ - ₆ alkenyl group; chloroacetyl, dichloroacetyl, trichloro port Asechiru, 2-chloro-E Chiruka Lupo alkenyl, triflumizole Ruo b acetyl, 2, 2, 2-Application Benefits chloro E chill carbonyl, 2, 2, 2-triflate Ruo Roe halo C ₂ such chill carbonyl - ₆ alkylcarbonyl group; 1 one chloro E Ji cycloalkenyl, 1- Buromoechiniru carbonyl, 3-black port propionyl carbonyl, such as 4 one chloro butenylcarbonyl Halo C _2-6 alkynylcarbonyl group; methoxymethylcarbonyl, ethoxymethylcarbo Nil, propoxymethylcarbonyl, butoxymethylcarbonyl, t-butyl D-6 alkoxy C _1-6 alkyl carbonyl groups such as methoxymethyl carbonyl, 1-methoxy carbonyl, 2-methoxy carbonyl, 3-methoxy propyl carbonyl, and 4-methoxy butyl carbonyl; methylthiomethyl carbonyl, ethyl Alkylthioalkylcarbonyl groups such as thiomethylcarbonyl, propylthiomethylcarbonyl, butylthiomethylcarbonyl, t-butylthiomethylcarbonyl, 1-methylthioethylcarbonyl and 2-methylthioethylcarbonyl; ethinyloxymethylcarbonyl, 2 - E Tini Ruo key shell chill, 1- pro Pini Ruo carboxymethyl carbonyl, C ₂ _ _s Arukiniruokishi alkylcarboxy alkenyl group such as 2-Petit sulfonyl O carboxymethyl carbonyl; Benzoiru group; main butoxycarbonyl Amino E butoxycarbonyl § Mino, propoxycarbonyl § Mino, Isopuropoki aryloxycarbonyl § Mino, butoxycarbonyl § amino, C such t-butoxycarbonyl § Mino _1-6 alkoxycarbonyl § amino group; methylcarbamoyl § Mino, Jimechiruka Rubamoiruamino, E Ji Mono- or di- _6- alkyl-substituted rubamoylamino groups such as rucarbamoylamino and getylcarbamoylamino; methoxyiminomethyl, ethoxyminomethyl, propoxyminomethyl, isopropoxyiminomethyl, butoxyminomethyl, t-butoxyimino _d-6 Arukokishii Minomechi Le group such as methyl; chloromethane Toki Consequences amino methyl, Jikurorome Tokishii Minomechiru, trichloro port main Tokishii Minomechiru, Torifuruorome Tokishii Minomechiru, 2, 2, 2 Trichloroacetic ethoxy imino-methyl, 2, 2, 2-Torifuruorome Toki Consequences Mino halo Arukokishii Minomechiru group such as methyl; Ariruokishii Minomechiru, 2 Buteniruo Kishii Minomechiru etc. C ₂ - _e alkenyl O key Consequences Minomechiru group; Echiniruokishii Mi Nomechiru, C _2-6 alkynoxyminomethyl group such as 1-propynyloxyminomethyl; 3-chloro-1-amino-1-propynyloxymino-methyl, 3-fluoro-1-lipinyloxymino, 4-chloro represents the mouth one 3-Petit sulfonyl O key Consequences Mino halo C ₂ _ ₆ alkynyl O key Consequences Minomechiru group or Fuwenirui Minomechiru group such as methyl.

Z is 0, representing S, SO, and S 0 ₂ or N-R _2.

Is a hydrogen atom; a cyano group; methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isoptyl, t-butyl, pentyl and its isomers, hexyl Le and C _1-6 alkyl groups of the isomers thereof; cyclopropyl, Shikuropuchiru, Shikurobe pentyl, c _3-7 cycloalkyl group heptyl etc. cyclohexyl, the cycloheteroalkyl; Eteniru, 1-propenyl, 2- Propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -methyl-2-butenyl, 2-methyl-2-butenyl, cyclohexenyl 1, cyclohexenyl 2, cyclohexenyl 3, 4 one hexenyl, C ₂ _ ₆ alkenyl group cyclohexenyl, etc., to 5; Echiniru, 1 one propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-1-propynyl, 2-methyl-13-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl , 4 one-pentynyl, 1-methyl 2 - butynyl, 2-methyl-one 3 - Pen ethynyl, hexynyl to 1, 1, 1 C, such as one dimethyl 2-heptynyl _2-6 alkynyl group; chloromethyl, Furuoromechiru, bromomethyl, Haloalkyl groups such as dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tripromomethyl, trichloroethyl, trifluoromethyl, pentafluoroethyl, etc .; Bae sulfonyl, 4-black port one 2 - butenyl, 4, 4 - Axis Rollo one 3-butenyl, 4, 4-difluoro over 3-butenyl, 3, 3-dichloro port one 2 one-propenyl etc. C ₂ - ₆ halo Alkenyl group; C ₂ _ ₆ haloalkynyl group such as 3-chloro-1-propynyl, 3-chloro-1-butynyl, 3-promo-1-butynyl; hydroxymethyl Alkyl groups such as methyl, hydroxyxetyl, and hydroxypropyl; ₆ alkoxy CM alkyl groups such as methoxymethyl, methoxyxethyl, ethoxymethyl, propoxymethyl, and butoxymethyl; methylthiomethyl, methylthioethyl, ethylthioethyl, ethylthiomethyl, and propylthio Q ₂ may be substituted with Fuwenokishime chill, 1 Fuenokishechiru, Fuesokishi C and 2-Fuenokishechiru - ₆ alkyl group; a methyl, C ₆ alkylthio alkyl groups such Puchiruchiome chill! Q may be substituted with ₂ full We Niruchiomechiru, Fuweni Lucio Ji _1-6 alkyl group such as phenylene Ruchioechiru; methylsulfinyl methyl, methylsulfinyl Rue chill, E chill sulfinyl Rue chill, E chill sulfinyl methyl, propyl Resurufinirume chill Petit Rusuru alkylsulfinyl alkylsulfinyl C _1-6 alkyl group such as methyl; C— _s alkylsulfonyl C ₆ alkyl group such as methylsulfonylmethyl, methylsulfonylethyl, ethylsulfonylethyl, ethylsulfonylmethyl, propylsulfonylmethyl, and butylsulfonylmethyl; phenylsulfonyl which may be substituted by Q ₂ ^ Alkyl groups; cyanomethyl, cyanoethyl, cyanopropyl, etc.

_1-6 alkyl group; methylaminomethyl, ethylaminomethyl, n-propylaminomethyl, isopropylaminomethyl, n-butylaminomethyl, isobutylaminomethyl, sec-butylaminomethyl, t-amino heptyl aminomethyl, 1 one methylbutyl aminomethyl, n- pentyl Rua amino C _1-6 Arukiruamino C _1-6 alkyl group such as methyl; dimethyl § amino methyl, Jefferies chill § amino methyl, dipropyl § amino methyl, di Petit Dialkylamino C _1-6 alkyl groups such as luminomethyl, ethyl isopropylaminomethyl, methylpropylaminomethyl; hydroxycarbonylmethyl, hydroxycarbonylethyl, hydroxycarbonylpropyl, hydroxycarboxylic carbonyl such Dorokishikarubo two Rubuchiru 0 _1-6 alkyl; main butoxycarbonyl Chill, E butoxycarbonyl methyl, main butoxycarbonyl E chill, C _1-6 alkoxycarbonyl C such butoxycarbonyl propyl Le - ₆ alkyl group;! O carboxymethyl oxiranylmethyl, Okishira Niruechiru, 2-methyl-O alkoxy oxiranylmethyl Okishiraniru such as methyl Alkyl groups; aziridinyl methyl groups such as aziridinylmethyl and aziridinylethyl alkyl groups; glycidyloxy ₆ alkoxy C _1-6 alkyl groups; azetidinonoxy C _1-6 alkoxy C

_1-6 alkyl group; formyl group; C _1-6 alkylcarbonyl group such as methylcarbonyl, ethylcarbonyl, propylcarbonyl, and butylcarbonyl; 1-propenylcarbonyl, 2-propenylcarbonyl, 1-butenyl Carbonyl, 2-butenylcarbonyl, 3-butenylcarbonyl, 1-methyl-2-propenylcarbonyl, 2-methyl-2-propenylcarbonyl, 1-pentenylcarbonyl, 2-pentenylcarbonyl, 3 —Pentenylcarbonyl, 4-pentenylcarbonyl, 1-methyl-1

2-butenylcarbonyl, 2-methyl-2-butenylcarbonyl, 1-hexenylcarbonyl, 2-hexenylcarbonyl, 3-hexenylcanoleponyl, 4-hexenylcarbonyl, 5-hexenyl C _2-6 alkenylcarbonyl such as carbonyl; chloromethylcarbonyl, fluoromethylcarbonyl, bromomethylcarbonyl, dimethyl Chloromethylcarbonyl, difluoromethylcarbonyl, dimethyl methylcarbonyl, trichloromethylcarbonyl, trifluoromethylcarbonyl, tribromomethylcarbonyl, trichloroethylcarbonyl, trifluoromethylcarbonyl, pentafluoroethylcarbonyl, etc. of C _1-6 haloalkylcarbonyl group; 3- black hole - 1 - propynyl carbonyl, 3 - chloro 1 - butynyl carbonyl, 3 - bromo - 1 one Petit two Rukaruponiru C ₃ _ ₆ haloalkynyl group such as; Q ₂ in which it may be substituted Benzoiru group; main butoxycarbonyl, ethoxycarbonyl, propoxy force Ruponiru, isopropoxy force Ruponiru, butoxycarbonyl, C etc. t one Butokishikarupo sulfonyl _1-6 alkoxycarbonyl group; may be substituted with C _{1 -6} al Kiruchio carbonyl group; force Rubamoiru group; which may be substituted by Q ₂ phenylalanine sulfonyl group; Q ₂ a benzyl group which may be substituted with methylsulfonyl, Echirusuruhoniru, propylsulfonyl, butyl alkylsulfonyl group such Rusuruhoniru ; is substituted by Q ₂ which may phenyl groups; substituted with or Q ₂ represents a heterocyclic group which may.

R ₂ represents a hydrogen atom or an alkyl group such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl and t-butyl. R ₂ may form a ring such as piperidino and pyrrolidino together with N—R i.

Is a cyano group; a halogen atom such as fluorine, chlorine, bromine, and iodine; a C _1-6 alkoxy group such as methoxy, ethoxy, and propoxy; a C _1-6 alkylthio group such as methylthio, ethylthio, and n-propylthio; Represents a C _1-6 alkoxycarbonyl group such as ethoxycarbonyl and ethoxycarbonyl.

Q ₂ is a cyano group; a nitro group; a halogen atom such as fluorine, chlorine, bromine, and iodine; a C _1-6 alkyl group; chloromethyl, fluoromethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, and trifluoromethyl. preparative ₆ Haroaru kill group and the like; main butoxy, Etokishi, C _1-6 alkoxy group propoxy; methylthio, E Chiruchio, C _1-6 alkylthio group or main butoxycarbonyl etc. n- propylthio, C etc. E Tokishikaruponiru _1-6 represents an alkoxycarbonyl group.

Examples of the hetero ring of Y and RL include a 5- or 6-membered heterocyclic group containing oxygen, sulfur or nitrogen as a hetero atom, and are preferably an unsaturated heterocyclic group. Take Examples of the 5- or 6-membered unsaturated heterocyclic group include 2-furyl, 3-furyl, 2-phenyl, 3-phenyl, 2-pyrrolyl, 3-pyrrolyl, 2-imidazolyl, 4-imidazolyl, and oxazolo. 2-ru, 2-oxyl, 4-oxyl, 4-oxyl-5-yl, isoxazole-3-yl, isoxol-14-yl, isoxazole-1 5-yl, thiazole-2-yl, thiazo 1-ru 41-yl, thiazole 5-yl, pyrazol 3-yl, pyrazole 4-yl, 1,2,3-triazo 1-4-yl, 1,2,4-triazo- 3 — yl, 1, 2, 4 — triazolo 5 yl, 1, 2, 3 — oxaziazol — 4 yl, 1, 2, 3 — oxaziazol 5 yl, 1, 3,4,5,5,6,5,6,9,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,10,11,10,10,10,10,10,10 I, I, I, I, I, I, I, I, I, I, I 1,2,3-thiadiazol-4yl, 1,2,3-thiadiazol-1-5-yl, 1,3,4-thiadiazol-1-2-yl, 1,3,4-th Asia-Zero 5-yl.

 m represents 0, 1 or 2, and n represents 0, 1, 2 or 3. When m and n are 2 or more, X and Y may be the same or different.

 The compound of the present invention can be produced according to the following production method.

(Manufacturing method 1)

 (twenty one)

 (In the formula, Z, X, Y, 1 ^, m and η represent the same meaning as described above.)

 The compound of the present invention can be produced by nitrating the compound represented by the general formula (2).

As the conditions for the nitration reaction, the ordinary conditions for the nitration reaction of an aromatic ring can be applied as they are. For example, a ditoxification agent such as fuming nitric acid or acetylethyl nitrate can be used without solvent or Can be produced by reacting in an organic solvent.

 Solvents used in this reaction include methylene chloride, chloroform, acetic acid, acetic anhydride and the like. The reaction proceeds smoothly at —40 ° C. to room temperature. (Production method 1)

 (3) (1)

(Wherein, Z, X, Y, m and η represent the same meaning as described above. L represents halogen, C _1-s alkylsulfonyl or an optionally substituted benzenesulfonyl group, and Represents a group excluding a hydrogen atom.)

(Production method 3)

 Further, the compound of the present invention comprises a compound represented by the general formula (3) and a compound represented by the general formula (4): for example, TW Greene et al, "Protective Groups in Organic Synthesis' John Wiley & It can also be produced according to the method described in Sons, Inc., 1991.

 Examples of a method for synthesizing an oxazole ring include a method according to the method for synthesizing oxazole described in I. J. Turchi, "The Chemistry of Heterocyclic Compounds" vol. 45, John Wiley & Sons, Inc., 1986. Methods A to C for the production of oxazoluyl 2-yl form, Method D for the production of oxazole-4-yl form, and E to J methods for the production of oxazole-5-yl form are as follows. Shown in These production methods can be applied not only to the compound of the present invention, but also to the intermediates represented by the general formulas (2) and (3).

(Method A)

(Wherein, and Z represent the same meaning as described above, and Y ₂ represents the same meaning as Y, and L represents a halogen atom, a C _1-6 alkylsulfonyl group, or an optionally substituted benzenesulfonyl. Represents a group.)

 In this method, the compound represented by the general formula (5), the compound represented by the general formula (6), and the dehydrating condensing agent are mixed with each other without any solvent or in a suitable solvent at a temperature from room temperature to a temperature lower than the boiling point of the solvent. The reaction is for 24 hours. In this case, the reaction can be carried out in the presence of a suitable base.

 Examples of the dehydrating condensing agent used in this reaction include phosphorus pentachloride, oxychlorinated phosphorus, polyphosphoric acid, phosphorus pentoxide, triphenylphosphine-carbon tetrachloride, etc.

 Examples of the solvent used include aromatic hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as dichloromethane and chloroform. Examples of the base include organic bases such as triethylamine, 18-diazabicyclo [5.4.0] indene 7-ene (DBU) and the like.

 As a combination of a dehydrating condensing agent, a base and a solvent, organic bases such as phosphorus oxychloride and triethylamine, and halogenated hydrocarbons such as chloroform are preferable.

(Method B)

(Wherein, and Z represent the same meaning as described above.)

 In this method, a compound represented by the general formula (5) is reacted with a compound represented by the general formula (7).

(Method C)

(Wherein, I!, Z, L, and Y ₂ are as defined above.)

 In this method, a compound represented by the general formula (8) and an aminoketone derivative represented by the general formula (9) are mixed in a suitable solvent in the presence of a base at a temperature from room temperature to a temperature lower than the boiling point of the solvent. The reaction is carried out for up to 24 hours.

 Examples of the solvent used in this reaction include aromatic hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as dichloromethane and chloroform. Further, in this case, the compound (9) can be produced in an excess amount without using a solvent. Examples of the base used in this reaction include organic bases such as triethylamine and DBU.

(Method D)

(Wherein,, Z, L and Y ₂ are as defined above, Upsilon ₃ have the same meanings as Upsilon above.)

 In this method, a compound represented by the general formula (10) and an amide derivative represented by the general formula (11) are treated in a suitable solvent in the presence or absence of a base in a suitable solvent at room temperature to a temperature of from The reaction is carried out at a temperature lower than the boiling point for 1 to 24 hours.

 Examples of the solvent used in this reaction include aromatic hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as dichloromethane and chloroform. In addition, the compound (11) can be produced in an excess amount using no excess solvent. Examples of the base used in this reaction include organic bases such as triethylamine and DBU.

(Method)

(Wherein, 1 ^, Z, L, Y 2 and Y ₃ are as defined above.)

 In this method, a compound represented by the general formula (12) and an amide derivative represented by the general formula (11) are prepared in the presence or absence of a suitable base in a solvent-free or suitable solvent. The reaction is carried out at room temperature to a temperature lower than the boiling point of the solvent for 1 to 24 hours.

 Examples of the solvent used for this reaction include aromatic hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as dichloromethane and chloroform. Examples of the base used include organic bases such as triethylamine and DBU.

(F method)

(In the formula, Z and Y ₃ represent the same meaning as described above.)

 In this method, the compound represented by the general formula (13) and the ditolyl derivative represented by the general formula (14) are prepared in the presence or absence of a suitable base in the absence of a solvent or a suitable solvent. The reaction is performed at room temperature to a temperature lower than the boiling point of the solvent for 124 hours.

 Examples of the solvent used for this reaction include aromatic hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as dichloromethane and chloroform. Examples of the base used include organic bases such as triethylamine and DBU.

(Method G)

(Wherein, Z and Y ₂ have the same meanings as described above, and To s represents a tosyl group.) This method comprises the steps of using a compound represented by the general formula (15) and an isoform represented by the general formula (16). The nitrile derivative is reacted in a suitable solvent in the presence of a suitable base at room temperature to a temperature lower than the boiling point of the solvent for 124 hours.

Examples of the solvent used in this reaction include alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, ethers such as THF DME, DMF and DMSO. The base used is hydrogenation And organic bases such as alkali metal, alkali metal carbonate, and triethylamine.

(H method)

 (8) (1f)

(In the formula, Ri, Z, L and Y ₂ represent the same meaning as described above.)

 In this method, the compound represented by the general formula (8) and the isotinitryl derivative represented by the general formula (17) are mixed in a suitable solvent in the presence of a suitable base at room temperature to a temperature lower than the boiling point of the solvent. The reaction is performed for 1 to 24 hours.

 Solvents used in this reaction include, for example, alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, ethers such as THF, 1,2-dimethoxetane (DME), DMF, and the like. DMSO. Examples of the base used include alkali metal hydrides, carbonates of alkali metals, and organic bases such as triethylamine.

(Method I)

_{(Wherein, 1 ^, Z, Y 2} , Υ 3 and T os are as defined above.)

In this method, the compound represented by the general formula (18) is tosyloxylated, and then reacted with tetrabutylammonium azide to form the compound represented by the general formula (19). An azido ketone derivative is obtained, and without further purification, the product is reacted with the acid halide derivative represented by the general formula (20) in the presence or absence of a suitable base in the presence of triflatil phosphine. The reaction is carried out in a solvent or a suitable solvent at a temperature from room temperature to a temperature lower than the boiling point of the solvent for 1 to 24 hours.

 Examples of the solvent used in this reaction include aromatic hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as dichloromethane and chloroform. Examples of the base used include organic bases such as triethylamine and DBU.

(J method)

(Wherein, R!, Z, Y ₂ and Y ₃ are as defined above, T f represents Torifuruoro Tan sulfonyl Le group.)

 In this method, a compound represented by the general formula (18) is subjected to trifluoromethanesulfonyloxylation to obtain a compound represented by the general formula (21), which is then represented by the general formula (14). The compound is reacted in a suitable solvent or without solvent at a temperature lower than the boiling point of the solvent for 1 to 24 hours.

 Examples of the solvent used in this reaction include aromatic hydrocarbons such as benzene and toluene.

(Production method 4)

(In the formula, Z, R, X and n represent the same meaning as described above, and Υ ₃ ′ represents a halogen atom, a formyl group, an alkylcarbonyl group, an O _1-6 alkyl group, a C _1-6 alkyl group rubamoyl group, C _1-6 alkylthio force Rubamoiru group, C _1-6 alkylthio group, a C _1-6 Arukirusurufu Iniru group, ₆ alkylsulfonyl group, or an alkoxycarbonyl two Le group.) among the compounds of the present invention, Okisazo Ichiru ring 2-position The compound represented by the general formula (2b) having a substituent (Υ ₃ ′) is obtained by reacting the compound represented by the general formula (2a) with an organic metal such as butyl lithium, and then reacting with an electrophilic reagent. Can be produced by reacting

_{(Wherein, Ri, Ζ, Υ 2,} Υ 3 are as defined above) in the presence of a base a compound represented by this method the compound represented by the general formula (22) and the general formula (20) The reaction is carried out without a solvent or in a suitable solvent at a temperature from room temperature to a temperature lower than the boiling point of the solvent, or by reacting with a carboxylic acid represented by the general formula (23) and a dehydrating agent to obtain a compound represented by the general formula (24). The amide compound represented by the formula (I) can be prepared by subjecting the amide compound to treatment with phosphorus oxychloride or triphenylphosphine carbon tetrachloride monobasic in a suitable solvent at a temperature from room temperature to a temperature lower than the boiling point of the solvent. Examples of the dehydrating agent used in this reaction include dicyclohexylcarbodiimid And 3- (3-dimethylaminopropyl) -1-ethylcarbodimid hydrochloride. Examples of the solvent used in these reactions include aromatic hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as dichloromethane and chloroform. Examples of the base used include organic bases such as triethylamine and DBU. As the salt of the compound represented by the general formula (1), a salt acceptable in agriculture and horticulture, for example, an inorganic acid salt such as hydrochloride and hydrogen bromide, and an organic acid such as acetate, oxalate and formate are exemplified. Acid salts, etc., and alkali metals, alkaline earth metals, ammonium salts and the like. These salts can be prepared in a conventional manner.

 The structure of the compound of the present invention can be determined from IR, NMR, MS and the like.

 The compound of the present invention or a salt thereof can be used for a wide variety of filamentous fungi, such as algae (Oomycetes), ascomycetes (Ascomycetes), incomplete fungi (Deuteromycetes), It has excellent bactericidal activity against fungi belonging to fungi (Basidi omy cetes).

 The composition containing the compound of the present invention as an active ingredient can be used for controlling various diseases that occur during the cultivation of agricultural and horticultural crops including flowers, turf, and pasture, by treating seeds, foliage application, soil application or water application. Can be used.

 For example,

Sugar beet brown spot (Ce rco s p o r a b e t i c o l a)

Laccasey Leaf spot (My cos p aer e l l a a r a c hi i d i s)

 Byaku Kuroshibu (My cos pha e r e l l ab e r k e l e y i) Kiyuri powdery mildew (S ρh a e r 0 t h e c a f u 1 i g i n e a)

 Vine blight (My c os p h a e r e l l a me l o n i s) Sclerotium blight (S c l e r o t i n i a s c l e r o t i o r um) Gray mold (B o t r y t i s c i n e r e a)

Black star? Κ (C ladospori um cuc ume rin um) Tomato Gray mold (Botrytiscinerea) Leaf mold (C ladospori um fulv um)

Eggplant gray mold (^ B o t r y t i s c i n e r e a)

 Black blight (.C or ny e s p or a me 1 o n g e n a e) Powdery mildew (Ery s i p e c i c h o r a c e a rum) Strawberry Gray mold (Bot r y t i s c i n e r e a)

 Powdery mildew (S o a e ro t h e c a h umu l i) Onion gray rot (B o t r y t i s a l l i i)

 Gray mold (B o t r y t i s c i n e r e a)

Single sclerotia (S c l e ro t i n i a s c l e r o t i o r um) Gray mold (B o t r y t i s c i n e r e a;

Phosphorus powdery mildew (Pod os p ae a la l e u c o t r i c a) Ping kuroboshi (V e n t r i a i a n a e qu a l i s) Monilia disease (Moni l i n i a m a 1 i)

Oyster powdery mildew (Phy l l a c t i n i a k a k i c o 1 a) Anthracite (G l o e o s p o r i um k a k i)

 Horn Spot Leaf Disease (Cercosporakaki)

Peach to rot (Mo ni l in i n i a f r u c t i c o l a) Grape ash crab (B o t r y t i s c i n e r e a)

 Byctonko (U n c i n u 1 a n e c a t o r r rot (G l ome r e l l a c i n g u l a t a) Pear black scab (V e n t u r i a n a s h i c o l a)

 Scab (Gymn o s p o r a n g i um a s i a t i c um) Black spot (A l t e r n a r i a k i ku c h i a n a) Cyan ring spot (P e st a l o t i a t h e a e)

 Anthracnose (C o l l e t o t r i c um t h e a e- s i n e n s i s)

Rikiki Shiokatsu disease (E 1 s i n o e f awc e t t i)

Blue mold (Penicilli um ita 1 ic um) Mold fungus (P enici 1 1 i um digitatum) Botrytiscinerea

Ery s i p h e g r am i n i s f. S p.

 o r d e i)

 Naked smut (U s t i 1 a g o n u d a)

 Wheat red mold (Gibb e reel az e ae) Red rust (Pu c c i n i a r e c o n d i t a) Leaf spot (C o c h l i o b o l u s s a t i v u s)

 Fusarium wilt (L e p t o s p h a e r i a n o d o r um)

 Powdery mildew (Erysiphegramiinisf.sp.triticci)

 Crimson snow rot (Mi cr o n e c t r i e l l a n i v a l i s) Rice blast l¾ (P y r i c u l a r i a o r y z a e)

 Bymon Monashi (Rh i z o c t o n i a s o 1 a n i)

 Stupid Seedling Disease (Gibbrele llafajjikuruoi), Sesame Leaf Blight Disease (Cochhlioboliu sniyabbeanu s)-Tanoko Bacterial Bacterial Disease (Scleront e i r e e r i e r i e r i e r i e r i e r i e r i e r i e r i e r i e r i e r i e r i e r i e r i e r i e r i e r i e r i e r i e r i e r i e r i e r i e r i e r i e r i e r y e

Bentgrass snow rot sclerotiniaborealis, o-chardgrass powdery mildew (Erysiphegr am inis), soybean purpura (Cercosporaki ku chii), potato 'tomato plague (Phyt 0 ρhthorainfestans). And disease (P seudoperonosporac ub ensis),

Grape downy mildew (P la smo paraviticola) It can be used for pest control.

 In recent years, various pathogens have developed resistance to benzimidazole fungicides ゃ dicarboximide fungicides, etc., resulting in insufficient efficacy of these drugs. ing. The compound of the present invention is a drug having an excellent bactericidal effect not only on pathogenic bacteria sensitive to such drugs but also on resistant bacteria. For example, gray mold fungus (Botrytiscinerea), sugar beet brown spot (Cercosporabeticola), and apple black spot (Venturiainae qu alis)> resistant to thiophanate methyl, benomyl, and carbendazim> Venturianashico The compound of the present invention is effective against 1a) as well as the susceptible bacteria.

 Furthermore, the compound of the present invention is also effective against gray mold fungi (Botryticincinerea) that are resistant to dicarboximide fungicides (eg, vinclozolin, procymidone, iprodione), as well as susceptible bacteria.

 Diseases that are more preferably applied include sugar beet brown spot, wheat powdery mildew, rice blast, apple scab, gray mold on cucumber, and brown spot on laccasei. Shows activity, therapeutic activity and residual activity.

 The compound of the present invention can also be used as an antifouling agent for preventing aquatic organisms from adhering to underwater objects such as ship bottoms and fish nets.

 Some compounds of the present invention exhibit insecticidal and acaricidal activity, herbicidal activity, and planting effect o

 Some of the compounds of the present invention show an excellent growth inhibitory effect against human parasitic fungi such as trichophyton and candida, and are useful as medical antifungal agents.

 Some intermediate compounds of the compound of the present invention exhibit bactericidal activity.

 Furthermore, by mixing the compound of the present invention into paints, arrowheads, and the like, it can be used as an antibacterial and antifungal agent for walls and bathtubs, or shoes and clothes.

When the compound of the present invention is actually applied, it can be used in a pure form without adding other components, and in a form that can be taken by a general pesticide for the purpose of using it as a pesticide, that is, a wettable powder, a granule, a powder, It can be used in the form of emulsion, water solvent, suspension, flowable, wettable powder, etc. it can.

 Additives and carriers that can be added to the pesticide formulation are solid powders, such as vegetable powders such as soybean flour and flour, diatomaceous earth, apatite, gypsum, talc, bentonite, and pyrolites. Organic and inorganic compounds such as mineral fine powders such as phyllite and clay, sodium benzoate, urea and sodium sulfate are used.

 For liquid dosage forms, kerosene, xylene and petroleum-based aromatic hydrocarbons, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, triklulethylene, methyl Isobutyl ketone, mineral oil, vegetable oil, water, etc. can be used as the solvent. Further, in order to obtain a uniform and stable form in these preparations, a surfactant may be added as necessary.

 The surfactant that can be added is not particularly limited, and examples thereof include alkylphenyl ether to which polyoxyethylene is added, alkyl ether to which polyoxyethylene is added, higher fatty acid ester to which polyoxyethylene is added, Nonionic surfactants such as sorbitan higher fatty acid esters to which polyoxyethylene is added, tristyryl ether to which polyoxyethylene is added, sulfates of alkylphenyl ether to which polyoxethylene is added, and alkylbenzene sulfones Acid salts, sulfates of higher alcohols, alkylnaphthalenesulfonates, polycarboxylates, ligninsulfonates, formaldehyde condensates of alkylnaphthalenesulfonates, copolymers of isobutylene-maleic anhydride, etc. Can be The amount of the active ingredient in the preparation is usually preferably from 0.01 to 90% by weight, more preferably from 0.05 to 85% by weight, based on the whole composition (preparation). The wettable powders, emulsions, flowables, aqueous solvents, and granule wettable powders thus obtained are diluted to a predetermined concentration with water to obtain a solution, suspension or emulsion. It is used as it is on plants.

The formulated fungicide composition of the present invention is applied as it is or diluted with water or the like to plant matter, seeds, water surface or soil. The application rate varies depending on the weather conditions, formulation, application magnetic field, application method, application site, target disease, target crop, etc., but usually 1 h The amount of the active ingredient compound per tar is 1 to 1, OOO g, preferably 10 to 100 g.

 It goes without saying that the compound of the present invention alone is sufficiently effective, but it can also be used in combination with one or more of various fungicides, insecticides and acaricides, or synergists. Representative examples of fungicides, insecticides, acaricides, and plant growth regulators that can be used by mixing with the compound of the present invention are shown below.

 (Fungicide)

Kyabtan, Forpet, Thiuram, Ziram, Zinep, Maneb, Mancozeb, Provineb, Polycarbamate, Chlorothalonil, Quintzenzen, Captafol, Iprodione, Procymidone, Vinclozolin, Fluoromid, Thymoxanil, Mepronil, Flupronil, Flupronil Xycarboxin, fosetylaluminum, propamocarb, triadimefon, triadimenol, propiconazole, diclobutrazole, bitelinol, hexaconazole, microbutanyl, flusilazol, metconazole, etaconazole, fluorconmazole , Cyproconazole, epoxyconazole, furtriaphan, benconazole, diniconazole, cyproconazole, funary Mohr, Triflumizole, Proc Mouth Raz, Imazalil, Perazolate, Tridemorph, Fenpropimorph, Triholin, Butiobeth, Pyrifenox, Anilazine, Polyoxin, Metalaxyl, Oxazixyl, Flaraxil, Isoprothiol Benazole, pyrrolnitrin, blasticidin s, kasugamycin, noridamycin, dihydrostrebtomycin sulfate, benomyl, carbendazim, thiophanetomethyl, himexazole, basic copper chloride, basic copper sulfate, Fentin acetate, triphenyltin hydroxide, dietophane carb, metasulfocarb, quinomethionate, binapacryl, lecithin, baking soda, dithianon, dinocap, phenaminosulfur, dichromedine, g Azatin, dozine, IBP, edifunphos, mepanipyrim, fermzon, triclamide, metasulfocarp, fluazinam, etoquinolak, dimet morph, pyroquilon, techmouth phthalam, fusaride, fenazinoxide, thiavendazole, tricyclizole , Vinclozolin, simoxanil, cyclobutanyl, Guazatine, propamocalp hydrochloride, oxolinic acid, hydroxyisoxazole, iminoctadine acetate, etc.

 (Insecticide and acaricide)

Organophosphorus and carbamate insecticides:

 Fenthion, dinitrothion, diazinon, chlorpyrifos, ESP, nomidotion, pentoate, dimethoate, formotione, marathon, trichlorfon, thiomethone, phosmet, dichlorvos, acephate, EPBP, methylparamethione Ethion, salicion, cyanophos, isoxathion, pyridafenthion, hosalon, methidathion, sulprophos, chlorfenvinphos, tetrachlorvinphos, dimethylvinphos, propaphos, isofenphos, ethylthiomethone, profinophos, pyraclofos, monoclomethos, monocrotomethol, monocrotophos methyl , Zodicalp, Carbofuran, Force Rubosulfan, Benfracalp, Fratioka Flop, Purobokisuru, B P M C, M T M C, M I P C, force Rubariru, pyridinium Mika one blanking, E Chio Fen Culp, phenoxy Culp, E D D P and the like.

Pyrethroid insecticides:

 Permethrin, Cypermethrin, Deltamethrin, Fuembrelet, Fenprohatrin, Pyrethrin, Arlesrin, Tetramethrin, Resmethrin, Dimethrin, Probasulin, Phunotrin, Protrin, Fluvalinate, Cyflutrin -Cyhalothrin, flucitrinate, etofenprox, cycloprotrin, tralomethrin, silafluofen, profenprox, acrinasulin, etc.

Benzoylurea and other insecticides:

Difluvenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, methoprene, benzepin, diafantiuron, acetamiprid, Imidacloprid, ditenviram, fipronil, cartap, thiocyclam, bensultap, nicotine sulfate, rotenone, metaaldehyde, machine oil, microbial pesticides such as BT and insect pathogenic viruses. Nematicide:

 Fenamiphos, phosthiazate, etc.

Acaricide:

 Chlorbenzilate, fenisobromolate, dicophor, amitraz, BPPS, benzometh, hexthiazox, fenbutatin oxide, polynactin, quinomethione, CPCBS, tetradihon, avermectin, milbemectin, clofentezin, Cihexatin, pyridaben, fenpyroximate, tebufenvirad, pyrimidifen, phenothocalp, dienochlor and the like.

 (Plant growth regulator)

 Gibberellins (eg, gibberellin A3, gibberellin A4, gibberellin A7) IA A, NAA and the like. BEST MODE FOR CARRYING OUT THE INVENTION

 Next, the compound of the present invention will be described in more detail with reference to Production Examples and Examples of the compound of the present invention.

 (Example 1)

 Preparation of 5- (3-Nitro-1-methoxyethoxymethoxy) oxazole (Compound No. 2-2)

3.8 g of 3-nitro-4-methoxyethoxybenzaldehyde, 4.2 g of p-toluenesulfonylmethyl isocyanide and 5 g of lithium carbonate were stirred and refluxed for 2 hours in 50 ml of methanol. Ice was added to the reaction solution, and the precipitated solid was filtered. The solid was dissolved in ethyl acetate, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 3.762 of the desired crystal. 1111) .91-92 ° C (Example 2)

 Production of 5- (3-nitro 4-hydroxyphenyl) oxazol (Compound No. 2-1)

 1 g of 5- (3-Nitro 4-methoxymethoxyphenyl) oxazole was dissolved in 20 ml of methanol, 2 ml of 3N-hydrochloric acid was added, and the whole volume was stirred at 50 to 60 ° C for 2 hours. The reaction solution was concentrated under reduced pressure, and the obtained solid was purified by silica gel column chromatography to obtain 0.6 g of the desired product. mp. 153-155 ° C

 (Example 3)

 Preparation of 5- (3-Nitro 4-acetoxyphenyl) oxazole (Compound No. 2-3)

 0.34 g of 5- (3-nitro-4-hydroxyphenyl) oxazole was dissolved in 10 ml of ethyl ether, and 1.14 g of lithium carbonate was added, followed by cooling to 0 ° C. Under stirring at the same temperature, 0.78 ml of acetic anhydride was added dropwise. After removing the ice-cooling bath and stirring at room temperature for 2 hours, 10 ml of water was added to the reaction solution, and the mixture was further stirred for about 1 hour. 50 ml of ethyl ether was added to the reaction solution, and the organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure to obtain 0.3 g of the target compound as yellow crystals. mp. 111 -115 ° C

 (Example 4)

4-Methyl-1- (3-nitro-4-hydroxyphenyl) oxazole (compound Manufacture of article number 2—83)

 2.11 g of 3-nitro-4-methoxyethoxybenzaldehyde, 2.lg of Ρ-toluenesulfonyl-methylmethylisocyanide and 1.388 g of potassium carbonate were stirred and refluxed in 50 ml of methanol for 8 hours. After completion of the reaction, the reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.5 g of the desired product as crystals. mp.168-171 ° C

 (Example 5)

 Production of 2-Methyl-5- (3-nitro-14-hydroxyphenyl) oxazole (Compound No. 2-22)

 Kolben containing 0.15 g of 2-methyl-5- (4-hydroxyphenyl) oxazole was cooled in an ice bath, and 0.15 ml of fuming nitric acid was added dropwise. After stirring at the same temperature for 30 minutes, the reaction product was added to ice water and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.05 g of the desired product as yellow crystals. mp. 166-168 ° C

(Example 6) Production of 5- (3-nitro-4-mercaptophenyl) oxazole (Compound No. 228)

 400 mg of (3-nitro-14-acetylthio) benzaldehyde, 35 Omg of p-toluenesulfonylmethyl isocyanide and 49 Omg of lithium carbonate were stirred and refluxed in 30 ml of methanol for 3 hours. After the reaction yield, the solvent was distilled off under reduced pressure, and ethyl acetate and water were added to the obtained residue. The organic layer was separated, the aqueous layer was extracted with ethyl acetate, the organic layers were combined, washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 12 mg of the desired product as orange-red crystals. mp. 218-220 ° C

 (Example 7)

 Preparation of 5- (3-Nitro 4-benzylthiophenidyl) oxazole (Compound No. 2-15)

70 mg of (3-12thro-4-benzylthio) benzaldehyde, 55 mg of p-toluenesulfonylmethylisocyanide and 70 mg of potassium carbonate were stirred and refluxed in 30 ml of methanol for 2 hours. After the reaction, the solvent was distilled off under reduced pressure, and ethyl acetate and water were added to the obtained residue. The organic layer was separated, the aqueous layer was extracted with ethyl acetate, the organic layers were combined, washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to give yellow crystals. 22 mg of the desired product were obtained. mp. 141— 2 ° C

 (Example 8)

 Preparation of 5- (3-Nitro-4-propargyloxif: nil) oxazole (Compound No. 2-6)

 62 mg of 5- (3-nitro-4-hydroxyphenyl) oxazole, 0.04 ml of propargylamide and 7 mg of carbonated lime were refluxed with stirring in 10 ml of acetone methanol for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and ethyl acetate and water were added to the obtained residue. The organic layer was separated, the aqueous layer was extracted with ethyl acetate, the organic layers were combined, washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 4 Omg of the desired product as crystals. mp. 121-124. C

 (Example 9)

 Production of 5- (3-nitro-4- 4-ethylpyraminophenyl) oxazole (Compound No. 2-20)

1-g of 3-nitro-4- 4-ethylethylaminobenzaldehyde, 0.97 g of p-toluenesulfonylmethyl isocyanide and 0.68 g of potassium carbonate were stirred and refluxed in 30 ml of methanol for 3 hours. . After the reaction, the solvent was distilled off under reduced pressure, and ethyl acetate and water were added to the obtained residue. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined layers washed with water, then dried over anhydrous magnesium sulfate, the residue of the solvent obtained _c was evaporated under reduced pressure and purified by silica gel column chromatography and foremost, the desired product as an oil

1.1 g were obtained.

nD 1.6235 (23.3 ° C) (Example 10)

Synthesis of 2-methylthiomethyl-1- (3-nitro-4-hydroxyphenyl) oxazole (Compound No. 2-59)

 70 mg of 2-methylthiomethyl-1- (4-hydroxyphenyl) oxazole was dissolved in a mixed solution of 15 ml of methylene chloride and 5 ml of acetic anhydride, and the mixture was stirred while cooling in an ice-water bath. To this solution, 2.2 ml of a acetic anhydride solution of 1.53 mmo 1 of acetyl nitrate prepared from acetic anhydride and fuming nitric acid was added dropwise. The reaction was performed at the same temperature for 30 minutes. After completion of the reaction, the mixture was poured into ice water, and the obtained suspension was extracted with ethyl acetate. The extract was washed with water and saturated saline, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain a crude crystal of the desired product. The obtained crude crystals were purified by silica gel column chromatography to obtain 230 mg of the desired product. mp. 108—110 ° C

 to 110]

 (Production Example 1)

Synthesis of 2-Methyl-4- (4-benzyloxyphenyl) oxazole

 A solution of 0.85 g of 4-benzyloxy-α-tosyloxyacetophenone and 12.7 g of acetoamide in 40 ml of toluene was stirred and refluxed for 16 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography to obtain 0.39 g of the desired crystal.

 (Production Example 2)

 Synthesis of 2-Formyl-5- (4-Methoxymethoxyphenyl) oxazole

No

 A solution of 1 g of 5- (4-methoxymethoxyphenyl) oxazole in THF5Om1 was cooled to 178 ° C, and 6.7 ml of a 1.6 Mn-butyllithium hexane solution was added dropwise under an argon atmosphere. After stirring at the same temperature for 1 hour, DMF 2 m

One was added. After reacting at the same temperature for 2 hours, the cooling bath was removed, the temperature was returned to room temperature, and the mixture was further stirred for 1 hour. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.8 g of the desired product.

 (Production Example 3)

Synthesis of 3-nitro-1- 4-ethylethylbenzaldehyde (C, H ₅ ), NH

 N,

^C 2 ^H 5 ^ ^C 2 ^H 5

 1-g of 4-nitrobenzene benzyl aldehyde was dissolved in 10 ml of acetonitrile, 1.97 g of getylamine was added, and the mixture was stirred at room temperature for 16 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and ethyl acetate and water were added to the obtained residue. The organic layer was washed with water and saturated saline, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 1 g of the intended product.

(Production Example 4)

Synthesis of 2-Methoxymethoxymethyl-5- (4-benzyloxyphenyl) oxazole Hiro Q

 4 To a solution of 2 g of monobenzyloxyaminoacetophenone hydrochloride in 70 ml of methylene chloride at room temperature was added 1.8 ml of triethylamine, then 1.04 g of methoxymethoxyacetic acid, and then 3 3-Dimethylaminopropyl) -1-ethylcarbodiimide 1.66 g was added. After stirring at room temperature for 16 hours, the solvent was distilled off under reduced pressure, and ethyl acetate and water were added to the residue. The organic layer was washed with dilute hydrochloric acid, saturated aqueous sodium hydrogen carbonate, water and saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 2.55 g of the desired product (amide). .

^ -NMR (CDC 13; <5 ppm) 3.45 (s, 3H), 4.13 (s, 2H) 4.75 (s & d, 4H), 5.15 (s, 2H), 7.05 (d, 2H), 7.3-7.45 (m, 5H) ^ 7.6 (brs, 1H), 7.95 (d, 2H) amide 350 mg, triphenylphosphine 0.87 g, tetrachloride A reaction mixture of 2.2 ml of carbon, 0.4 ml of triditylamine and 10 ml of methylene chloride was heated to reflux for 8 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and ethyl acetate and water were added to the obtained residue. The organic layer was washed with dilute hydrochloric acid, saturated aqueous sodium hydrogen carbonate, water and saturated saline, and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain crude crystals of the desired product. The obtained crude crystals were purified by silica gel column chromatography to obtain 0.17 g of the desired product

¹ H-NMR (CDC 1a; <5 PPm) 3.43 (s, 3H), 4.7 (s, 2H), 4.80 (s, 2H), 5.20 (s, 2H) ), 7.0 (d, 2H), 7.3-7.5 (m, 5H), 7.6 (d, 2H)

 Representative examples of the compounds of the present invention including the above compounds are shown in Tables 1 to 3.

 In Tables 1 to 3, abbreviations have the following meanings.

 P h: Huyunil

 c-H e X y 1: cyclohexyl

n— Hey 1: n—hexinole

 c-Pr: cyclopropyl

A c: acetyl

* a Physical properties are melting point or refractive index o. Xn Yl Y2 ZR Physical properties * a-1 HHH 0 H

-2 H CH3 H 0 H 141-144-3 H CH3 CH3 0 H 140-143-4 H H CH3 0 H

-5 H -CH2GH2CH2GH2- 0 H

-6 H -CH2CH2CH2CH2- 0 C0CH3

-7 H CH3 CH3 0 G0CH3 127-130 -8 H H H 0 G0CH3

-9 H CH3 H 0 C0CH3

-10 H H CH3 0 G0CH3

-11 H CH3 CH3 0 CH3

-12 H CH3 CH3 0 CH20CH3

-13 H CH3 CH3 0 CH2C≡CH

-14 H CH3 CH3 0 CH2C CI

-15 H CH3 CH3 0 CH2CH = GH2

-16 H CH3 CH3 0 CH2GH = CC12

-17 H CH3 CH3 0 CH2Ph

-18 H CH3 CH3 0 CH2SCH3

-19 H CH3 CH3 0 CH2S0CH3

-20 H CH3 CH3 0 CHZS02CH3

-21 H CH3 CH3 0 Ph

-22 H CH3 CH3 0 CH2CN

-23 H CH3 CH3 0 • CH2C (I) = CI2

-24 H CH3 CHS 0 CH2C (C1) = CC12

-25 H CH3 CH3 0 CH2CH2C00CH3

-26 H CH3 CH3 0 C0G (GH3) 3

-27 H CH3 CH3 0 C0C2H5

-28 H CH3 CH3 0 C0C3H7

-29 H CH3 CH3 0 C0C4H9

-30 H CH3 CH3 0 C0C6H13

-31 H CH3 CH3 0 C0CH2CH = CH2

-32 H CH3 CH3 0 C0GH = GH2

-33 H CH3 CH3 0 C0CH20CH2C≡CH

-34 H CH3 CH3 0 C0CH2C1

-35 H CH3 CH3 0 C0G (CH3) 2C2H5

-36 H CH3 CH3 0 C0C (CH3) 2Ph

-37 H CH3 CH3 0 C0N (CH3) 2

-38 H CH3 CH3 0 * 1

-39 H CH3 CH3 0 CH2CH (0H) CH2NH2

-40 H CH3 CH3 0 CH2CH (0H) CH2N3 1 Table (continued:

 λη Y2 z R Physical properties * a u

丄 ^ 丄 n GH3 0 * 2

丄 · ¾ώ — ΠΗ nu

 Tld CH3 0 H

丄 — 4ΐ O-J UZ CH3 0 H

ττο

丄 — ¾ CH3 0 H

 u u

Ϊ 4 Ϊ 3 Π Π H s H

 Three

Page 8 il n H s CH2Ph

 1—4 u

丄 0y n CH3 s H

 u

丄 (DU Π nuo

 πο s C0CH3

丄 0 丄 し s CH3

丄 — Π tld s CH2Ph

丄 — n Π H NH CH3

 1-54 H CH3 CH3 NCH3 CH3

 1-55 H CH3 CH3 NH H

 1-56 H CH3 CH3 N CH2CH2CH2CH2

 1-57 H CH3 CH3 N CH2CH2CH2CH2CH2

 1-58 H CH3 CH3 N CH2CH20CH2CH2

 1-59 H CH3 CH3 NH Ph

 1-60 H CH3 CH3 NH CH2Ph

* 2

* a Physical properties are melting point or refractive index o.Xn Y3 Y2 ZR Physical properties * a-1 HH CH3 H 168-171-2 HH CH3 CH3 149-150-3 HH CH3 CH2CH20H 79-81-4 ZR 1.6262 (23.7) -5 108-111 -6 HH ZR = J. 77-79 .-7 HHH NC2H5 C2H5 6235 (23.3) -8 HHH NC3H7 C3H7 6048 (22.9) -9 HHH NC z4H9 C4H9 5907 (23.5)

 R

-10 H H H NC6H1-11 C0CH3 5592 (22.7) -11 H H H NCH3 C0CH3 142-145-12 H H H NCH3 CH3 121-123-13 H H H NH CH3 215-222-14 H H H m C00C2H5

-15 H H H NH S02CH3

-16 H H H NH C0CH3 178-183-17 H H H NH C0CH2C1

-18 H H H NH c-Hexyl 83-85-19 H H H NH n-Hexyl 95-97-20 H H H NH GH2CH = CH2 93-95-21 H H H NH CH2C≡GH

-22 HHH NH 4-CH3-Ph 175-178-23 HHH NH 4-0CH3-Ph 147-150-24 HHH NH 4-Cl-Ph 196-199-25 HHH NH 2-CH3-6-CH3-Ph 192 -195-26 HHH 0 H 153-156-27 HHH 0 CH20GH3 91-92-28 HHH 0 C0CH3 111-115-29 HHH 0 CH (CH3) C00H 185-188-30 HHH 0 CH (CH3) C00CH3 oi l- 31 HHH 0 CH2C≡CH 121-144-32 HHH 0 CH2C≡CI 125-127-33 5-0CH3 HH 0 H 154-158-34 5-Br HH 0 H> 250-35 5-CH3 HH 0 H 133- 135-36 5-C1 HH 0 H 162-164-37 5-FHH 0 H 168-173

one

w

G 2 Table (continued)

 No. Xn Y3 Y2 Z R Physical properties * a

2-84 H H H 0 CSNHPh

 2-85 H H H 0 CH2Ph

 2-86 H H H 0 Ph-2-Cl-4-Cl

 2-87 H H H 0 pyridyl

 2-88 5-0CH3 H H 0 CH2C GH 172-174

2-89 H H H 0 CH2CH = C (G1) 2 101-103

2-90 H H H 0 CH2CH20H 128-130

2-91 H H H 0 Ph 124-127

2-92 H H H 02-Cl-6-Cl-Ph 145-146

2-93 H H H 0 C0N (C2H5) 2 133-135

2-94 H H H 0 2-Cl-4-Cl-Ph 1.6418 (20.5)

2-95 H H H 0 S02CF3 1.5413 (22.8)

2-96 H H H 0 P (0) (0C2H5) 2 1.5213 (22.8)

2-97 H H H 0 CH20C0C (CH3) 3 oil

2-98 H H H s CH2Ph 141-142

2-99 H H H s H 218-220 -100 H H H s C0GH3 116

2-101 H H H s CH2G≡CH

 2-102 H H H s C0C (CH3) 2Ph

 2-103 H H H s C0C (CH3) 3

 2-104 H H H s CH3 143 '

2-105 H H H S02 tolyl

 2-106 H n- C11H23 H 0 H 58-60

2-107 H N02 H 0 H

 2-108 H 0CH3 H 0 H

 2-109 H Ph CH3 0 H

 2-110 H Ph H 0 H 149-152

2-111 H Ph-4-CH3 H 0 H

 2-112 H Ph-4-Cl H 0 H

 2-113 H SCH3 H 0 H 111-113

2-114 H SCH3 N02 0 H 173-174

2-115 H thienyl H 0 'H 135-137

2-116 H CH2NH2 H 0 H

 2-117 H CH2N (CH3) 2 H 0 H 176

2-118 H CH2CH2NH2 H 0 H

 Z_ 丄 丄 u Π then HZ then J Π u n

 2-120 H CH2C00H H 0 H

 2-121 H CH2C0NH2 H 0 H

 2-122 H CH20C0CH3 H 0 H 119-121

 CH, — N I! H in H 22R-228

2-123

 H H 0 H 177-178

2-124

Table 1

 No. An v 10o XI LR Physical properties * a-170 H CH2CH2CH (CH3) 2 H 0 H 90-92-171 H CH = N0CH2CH (CH3) 2 67-69-172 H GH = N0CH (CH3) C2H5 H 0 H 96-98 -173 H CH,-0 H 0 H 142-143 -174 H CH = N0CH2CH2GH (GH3) 2 H 0 H 81-84-175 H CH = N0CH2CH2CH (CH3) 2 * H 0 H 147-149 -176 H GH = N0CH (CH3) C2H5 * H 0 H 163-165-177 H CH2GH20C2H5 H 0 H 136-138-178 H CH20CH2CH20C4H9 H 0 H 51-53-179 H CH = N0CH2CHF2 H 0 H 116-118- 180 H CH2S02CH3 H 0 H 229-232-181 H CH20CH20CH3 H 0 H 93-94-182 H CH2CH (CH3) C2H5 H 0 H 85-87-183 H C0NH2 H 0 H〉 300-184 H CH = N0CH2C≡CI H 0 H 148-150-185 H CH2CH2CH (CH3) 2 H 0 CH20C0C (CH3) 3 oil-186 H CH = N0CH2C (= CH2) CH3 H 0 H 85-86-187 H CH = N0CH2C≡CCH3 H 0 H

-188 H CH = N0CH (CH3) C≡CH H 0 H

-189 H CH = N0CH = C (CH3) 2 H 0 H

-190 HC O CO h h H 0 H 158-161-191 H CH20COPh H 0 COPh 121-123-192 H CH20C0NHC2H5 H 0 H 166-169-193 H CH20C0CH2C1 H 0 H 129-131-194 H CH20CH (CH3) C00CH3 H 0 H 118-121-195 H CH20C0C (CH3) 3 H 0 H 148 -151 -196 H CH20C0C (CH3) 3 H 0 CH20C0C (CH3) 3 87-89-197 H CH2N3 H 0 H 116-119 氺: Syn

* a Physical properties are melting point or refractive index o. Xn Y3 Yl ZR Physical properties * a-1 HHH 0 H

-2 H H H 0 G0GH3

-3 H H H 0 CH20CH3

-4 H CH3 H 0 H 125-127 -5 H CH3 CH3 0 H

-6 H H CH3 0 H

-7 H CH3 CH3 0 C0CH3

-8 H H H 0 CH3

-9 H CH3 H 0 CH20 CH3

-10 H H CH3 0 CH2C≡CH

-11 H CH3 CH3 0 GH2C≡CI

-12 H CH3 CH3 0 CH2CH = CH2

-13 H CH3 CH3 0 CH2CH = CG12

-14 H CH3 CH3 0 CH2Ph

-15 H CH3 CH3 0 CH2SCH3

-16 H CH3 CH3 0 CH2S0CH3

-17 H CH3 CH3 0 GH2S02CH3

-18 H CH3 CH3 0 Ph

-19 H CH3 CH3 0 CH2CN

-20 H CH3 CH3 0 CH2C (I) = CI2

-21 H CH3 CH3 0 CH2C (G1) = CC12

-22 H CH3 CH3 0 CH2GH2G00CH3

-23 H CH3 CH3 0 C0G (CH3) 3

-24 H CH3 CH3 0 C0C2H5

-25 H CH3 CH3 0 C0C3H7

-26 H CH3 CH3 0 C0C4H9

-27 H CH3 CH3 0 C0C6H13

-28 H CH3 CH3 0 C0GH2CH = CH2

-29 H CH3 CH3 0 C0CH = CH2

-30 H CH3 CH3 0 C0CH20CH2C≡CH

-31 H CH3 CH3 0 C0CH20CH2C≡CH

-32 H CH3 CH3 0 C0C (CH3) 2Ph

-33 H GH3 CH3 0 C0CH = CHCH3

-34 H CH3 CH3 0 CONHPh

-35 H CH3 GH3 0 C0CH2C1

-36 H CH3 H 0 C0CH20CH3

-37 H CH3 H 0 C0CH2SCH3

-38 H CH3 H 0 C0CH3

-39 H CH3 H 0 C0C2H5

-40 H CH3 H 0 CH2C≡CH 3rd ^ ίς (continued)

o.Xn Y3 Yl z R Physical properties * a-41 H CH3 H 0 CH2C≡CI

-42 H CH3 H 0 CH2CH = CH2

-43 H CH3 H 0 CH2GH = CC12

-44 H CH3 H 0 CH2Ph

-45 H GH3 H 0 CH2SCH3

-46 H CH3 H 0 CH2S0CH3

-47 H CH3 H 0 CH2S02CH3

-48. H CH3 H 0 Ph

-49 H CH3 H 0 CH2CN

-50 H CH3 H 0 CH2C (I) = CI2

-51 H CH3 H 0 CH2C (C1) = CC12

-52 H CH3 H 0 CH2CH2C00CH3

-53 H CH3 H 0 C0C (CH3) 3

-54 H CH3 H 0 C0C3H7

-55 H CH3 H 0 C0C4H9

-56 H CH3 H 0 G0C6H13

-57 H CH3 H 0 C0CH2GH = CH2

-58 H CH3 H 0 C0GH = CH2

-59 H CH3 H 0 Garden 20CH2C

-60 H CH3 H 0 C0CH20CH2C≡CH

-61 H. CH3 H 0 C0C (CH3) 2Ph

-62 H CH3 H 0 C0CH = CHCH3

-63 H GH3 H 0 CONHPh

-64 H CH3 H 0 C0CH2C1

-65 H CH3 H 0 C0CH20CH3

-66 H CH3 H 0 C0GH2SCH3

-67 H CH3 H S H

-68 H CH3 H S G0CH3

-69 H CH3 H S CH2Ph

-70 H CH3 H NC2H5 C2H5

〔Fungicide〕

 Next, examples of the composition of the present invention will be described. The additives and the proportions to be added are not limited to these examples, but can be varied over a wide range. Parts in Examples of Preparations indicate parts by weight.

Example 1 1 wettable powder

 Compound of the present invention 40 parts

 Cray 4 8 copies

 Dioctyl sulfosuccinate sodium salt 4 parts

 Lignin sulfonic acid sodium salt 8 parts

 If the above are uniformly mixed and finely pulverized, a wettable powder with an active ingredient of 40% is obtained. Example 12 Emulsion

 Compound of the present invention 10 parts

 Solbesso 2 0 0 5 3 parts

 Cyclohexanone 2 6 parts

 Dodecylbenzenesulfonic acid calcium salt 1 part

 Polyoxyethylene alkylaryl ether 10 parts

 By mixing and dissolving the above, an emulsion containing 10% of the active ingredient is obtained.

 [0 1 3 53

Example 13 Dust

 Compound of the present invention 10 parts

 Clay 90 parts

 If the above are uniformly mixed and finely pulverized, a powder containing 10% of the active ingredient is obtained. Example 1 4 granules

 5 parts of the compound of the present invention

 Clay 7 3 parts

 Bentonite 20 parts

 Dioctyl sulfosuccinate sodium salt 1 part

Potassium phosphate 1 part After pulverizing and mixing the above well, adding water and kneading well, granulated and dried to obtain the active ingredient

Obtain 5% granules.

Example 15 Suspension

 Compound of the present invention 10 parts

 Polyoxyethylene alkylaryl ether 4 parts

 Sodium polycarboxylate 2 parts

 Glycerin 10 parts

 Xanthan gum 0.2 parts

 Water 73.8 parts

 By mixing the above and wet milling until the particle size becomes 3 microns or less, the active ingredient 1

Obtain 0% suspension.

Example 16 wettable powder for granules

 Compound of the present invention 40 parts

 Clay 3 6 parts

 Potassium chloride 10 parts

 Alkylbenzenesulfonic acid sodium salt 1 part

 Lignin sulfonic acid sodium salt 8 parts

 Alkylbenzenesulfonic acid sodium salt

 Formaldehyde condensate 5 parts

 After mixing the above uniformly and finely pulverizing, add an appropriate amount of water and knead to make a clay. If the clay is granulated and dried, a wettable powder with an active ingredient of 40% is obtained. Industrial applicability:

 Next, test examples show that the compound of the present invention is useful as an active ingredient of various plant disease controlling agents.

Test example 1 Apple scab control test (prevention test)

Emulsions of the compound of the present invention were sprayed on apple seedlings (variety “Kunimitsu”, 3-4 leaf stage) cultivated in unglazed pots at a concentration of 200 lpm of the active ingredient. After air drying at room temperature, Conidia of the scab of the coral scab (Venturiainaequa 1 is) were inoculated and kept in a room at 20 ° C. and high humidity for 2 weeks, repeating the light and dark every 12 hours. The following compounds showed excellent control value of 75% or more as a result of comparing and examining the appearance of lesions on leaves with no treatment.

 The compound numbers correspond to the compound numbers in Tables 1 to 3.

 1-2, 1-3, 1-7, 2-26, 2-28, 2-41, 2-42, 2-44, 2-54, 2-66, 2-93, 2-113, 2- 127, 2-138, 2-142, 2-144, 2-146, 2-150, 2-153, 2-156, 2-162, 2-164, 2-168, 2-171, 2-172, 3-4

 Test example 2 Test for controlling bean gray mold (prevention test)

 The flowers of the kidney beans (variety “Nagauzura”) cultivated in the seedling raising batch were excised, and the emulsion of the compound of the present invention was immersed in a chemical solution adjusted to a concentration of 200 ppm of the active ingredient. After immersion, it was air-dried at room temperature and spray-inoculated with wingen gray mold fungus (Botryticisinerea). The inoculated flowers were placed on untreated leaf leaves and kept in a high-humidity constant temperature room (20 ° C) where light and dark were repeated every 12 hours for 7 days. The lesion diameter on the leaves was compared with that of untreated leaves, and the control value was determined. As a result, the following compounds showed excellent control values of 75% or more. The compound numbers correspond to the compound numbers in Tables 1 to 3.

 2-26, 2-27, 2-28, 2-31, 2-32, 2-35, 2-36, 2-37, 2-42, 2-45, 2-48, 2-50. 54, 2-56, 2-59, 2-62, 2-66, 2-74, 2-89, 2-93, 2-95, 2-96, 2-97, 2-100, 2-114, 2-122, 2-124, 2-127, 2-130, 2-132, 2-137, 2-138, 2-140, 1-141, 2-142, 2-144, 2-146, 2- 147, 2-148, 2-149, 2-150, 2-152, 2-153, 2-155, 2_156, 2-158, 2-159, 2-161, 2-162, 2-164, 2- 165, 2-167, 2-168, 2-169, 2-170, 2-171, 2-172, 2-173, 2-174, 2-175, 2-176, 2-177, 2-178, 2-179, 2-181, 2-183, 2-184, 2-191, 2-192, 2-193, 2-195, 2-196, 2-197

 Test example 3 Wheat powdery mildew control test (prevention test)

A wettable powder of the compound of the present invention was applied to wheat seedlings (variety “Norin 61”, 1.0 to 1.2 leaf stage) cultivated in unglazed pots at a concentration of 200 ppm of the active ingredient. After the leaves are air-dried, conidiospores of wheat powdery mildew (Erysiphegr am inisf.sp.tritici) are shaken off, inoculated, and kept in a greenhouse at 22-25 ° C for 7 days. Was. The appearance of lesions on the leaves was compared with that of no treatment, and the control effect was determined. As a result, the following compounds showed excellent control values of 75% or more. The compound numbers correspond to the compound numbers in Tables 1 to 3.

 1-2, 1-3> 2-26, 2-36, 2-42, 2-44, 2-138, 2-153, 2-154, 2-155, 2-171 Test Example 4 Grape downy mildew Control test (prevention test)

 Emulsions of the compound of the present invention were sprayed on the grape seedlings (variety “Koshu”, 2 leaf stage) cultivated in unglazed pots at a concentration of 200 ppm of the active ingredient. After spraying, air-dry at room temperature, inoculate with a suspension of zoosporangium of Plasmo parasitic fungus (Plasmo paravitico 1a), and in a high-humidity constant temperature room (20 ° C) for 10 days. The appearance of lesions on the leaves was compared with that of no treatment, and the control effect was determined. As a result, the following compounds exhibited excellent control effects of 75% or more. The compound numbers correspond to the compound numbers in Tables 1 to 3.

 2-8, 2-26, 2-32, 2-41, 2-42, 2-44, 2-45, 2-50, 2-60, 2-66, 2-69, 2-71, 2- 89, 2-92, 2-94, 2-95, 2-113, 2-114, 2-115, 2-140, 2-141, 2-144, 2-145, 2-146, 2-150, 2-156, 2-157, 2-159, 2-160, 2-164, 2-166, 2-167, 2-172, 2-179, 2-182, 2-184, 2-190, 2- 195, 3-4

Claims

The scope of the claims

 1. General formula (1)

 (1)

(Wherein, represents a halogen atom, a nitro group, Shiano group, c _1-6 alkyl group, arsenate Dorokishi group, an alkoxy group, CI- ₆ haloalkoxy group, C - ₆ alkylamino group, Jijito ₆ § alkylamino group , A C _1-6 alkylthio group, a C _1-6 alkylsulfinyl group, a C- ₆ alkylsulfonyl group, a formyl group or an alkylcarbonyl group,

Y is a halogen atom, Shiano group, a nitro group, c _1-12 alkyl group, c _2-6 alkenyl group, C ₂ - ₆ alkynyl group, C _3-7 cycloalkyl group, CI- ₆ alkoxy group, Haroaru Kokishi group , C _1-6 haloalkyl group, heat Dorokishi C - ₆ alkyl group, C _1-6 alkoxy alkyl, alkoxy C -! ₆ alkoxy group, C _1-6 haloalkoxy alkyl group, C _1-6 alkylthio group, C ₂ _ ₆ Arukiniruokishi CM § alkyl group, an amino c _1-6 alkyl group, c _1-6 alkylamino group, di-alkylamino group, _d-6 alkylthio group, a formyl group, _d-6 alkylcarbonyl groups, C an alkoxy carbonyl group, mono- or di-alkyl substituted force Rubamoiru group, may be substituted by Q ₂ full We carbamoylmethyl group, a mono- or di-substituted Chiokaruba moil group, in optionally substituted Good Arukirui Minomechiru group, a benzyl group which may be substituted with Q _2, which may be substituted by Q ₂ Fuweniru group, heterocyclic group which may be substituted by Q _2, halo C ₂ - ₆ alkenyl group, halo C ₂ _ ₆ alkynyl group, hydroxycarboxylic § Lal kill group, Shiano alkyl group, may be substituted by Q ₂ Fuwenokishi C _1-6 alkyl group, may be substituted by Q ₂ Fuweniruchio CM alkyl group, an alkylsulfinyl group , alkylsulfonyl (^ - ₆ alkyl group, even Ji may Fuweni Rusuruhoniru substituted with Q ₂ ^ alkyl group, a carboxy C alkyl group, alkoxycarbonyl C -! ₆ alkyl group, an alkyl group substituted with a heterocyclic ring , Substituted with oxysilane C ^ - ₆ alkyl group, a force Rubamoiru Ji ^ alkyl group, a mono- or di-alkyl substituted force Rubamoiruokishi _d-6 alkyl group, an off We sulfonyl carbamyl be replaced by Q ₂ Moi Ruokishi Ji ^ alkyl, alkylcarbonyl O alkoxy alkyl group, C port alkyl carbonylation Ruokishi Ji ^ alkyl group, C ₂ - ₆ alkenyl group, halo

C _2-6 alkylcarbonyl group, halo C ₂ _ _s alkynylcarbonyl, alkoxy C 6 alkyl carboxymethyl sulfonyl group, C _1-s alkylthio alkylcarbonyl group, c ₂ _ ₆ Al Kiniruokishi C w alkylcarbonyl alkylsulfonyl group, Q may be substituted with ₂ Benzoiru group, CM alkoxycarbonyl § amino group, a mono- or _{di-alkyl-substituted} force Rubamoi Ruamino group, C -! ₆ alkoxide Consequences amino methyl group, a halo C _1-6 alkoxide Consequences amino methyl group,

C ₂ - ₆ alkenyl O key Consequences amino methyl, C _2-6 alkynyl O key Consequences amino CI- ₆ alkyl group, halo C ₂ - ₆ alkynyl O key Consequences amino methyl, may be substituted by Q ₂ Fuweniru iminomethyl group, a mono- or di-alkylaminoalkyl group, Q may be substituted with ₂ Ararukiruokishi alkyl group, may be substituted by Q ₂ Ararukiruo Kishiiminomechiru group, C ₃ _ ₇ cycloalkyl group, d_ _s Arukokishikaru Boniru alkoxy C _1-6 alkyl group, a hydroxy I amino methyl group, a halo C ₂ _ ₆ § Luque sulfonyl O key Consequences amino methyl, may be substituted by Q ₂ Ararukiruokishi § alkyl group or an azide substituted alkyl group.

Z is, 0, S, represents a S 0, S 0 ₂ or N-R _2.

Is a hydrogen atom, an alkyl group, C ₃ - ₇ cycloalkyl, C ₂ _ ₆ alkenyl, C _2-6 alkynyl, C _1-6 haloalkyl group, 0 ₂₆ haloalkenyl, C ₂₆ Haroaruki group, human Dorokishi alkyl group, an alkoxy _alkyl group, alkylene thioether Ji ₆ alkyl group, Q may be substituted with ₂ phenoxy C _1-6 alkyl groups, which may be Fuweniruchio alkyl group substituted with Q _2, C _1-6 alkyl Surufi sulfonyl Ji ^ alkyl group, Ji ₆ alkylsulfonyl Ji ^ alkyl group, substituted by Q ₂ also Ji good full Enirusuruhoniru ^ alkyl group, Shiano alkyl group, alkylamino C _1-6 alkyl group, a di Alkylamino ₆ alkyl groups, hydroxycarbonyl C _1-6 alkyl group, C _1-6 alkoxycarbonyl alkyl group, oxylanyl CM alkyl group, aziridinyl ₆ alkyl group, Sigiloxy alkoxy alk Group, § Ze histidinol Non O alkoxy alkoxy alkyl group, a formyl group, Al kill carbonyl group, C ₂ - ₆ alkenyl group, c _1-6 haloalkylcarbonyl group, C ₂ - ₆ haloalkynyl group, CI- ₆ alkoxy C _1-6 alkyl Cal Poni Le group, C w alkylthio C _1-6 alkylcarbonyl group, C ₂ - ₆ Arukiniruokishi C ₆ alkyl force Ruponiru group, may be substituted by Q ₂ Benzoiru group, C _1-6 alkoxycarbonyl group, in which may be substituted alkyl thio group, an alkylsulfonyl group, may be substituted by Q ₂ full We alkenyl sulfonyl group, a force Rubamoiru group, may be substituted by Q ₂ Fuweniruchio force Rubamoiru group, Q ₂ in an optionally substituted benzyl group, Q ₂ may be substituted with Fuweniru group, which may be heterocyclic group substituted with Q _2, alkoxy C w alkoxy Shi CH alkyl group, a mono- or di-C w alkyl-substituted Karubamo I group, di-alkyl phosphonyl group, alkylcarbonyl two Okishi alkyl group, Amino substituted hydroxyalkyl group, substituted with azido-substituted hydroxyalkyl Le group or Q ₂ Represents a good phenylcarbamoyl group.

R ₂ may represent a hydrogen atom or a C _1-6 alkyl group, or may form a ring together with N—.

The above represents a cyano group, a halogen atom, an alkoxy group, an alkylthio group, or a C ₆ alkoxyl group.

Q ₂ represents a cyano group, a nitro group, a halogen atom, a C _1-6 alkyl group, a C ₆ haloalkyl group, a C _1-s alkoxy group, an alkylthio group, or a _{ds s} alkoxycarbonyl group.

 The heterocyclic group represents a 5- or 6-membered unsaturated heterocyclic group containing an oxygen, sulfur or nitrogen atom as a hetero atom.

m represents 0, 1 or 2, and n represents 0 or an integer of 1 to 3. When m and n are 2 or more, X and Y may be the same or different. Further, when m is adjacent two Y 2, C ₄ two Y - ₅ may form an alkylene. ) A compound represented by the formula or a salt thereof.

2. —General formula (1)

(Wherein, X, Y, Ζ, R i, m and η have the same meanings as above.) Or one or more of the salts thereof as an active ingredient An agricultural and horticultural fungicide characterized by the following characteristics.