WO2001087857A1 - Composes de phenyloxazole et fongicides a usage agricole et horticole - Google Patents

Composes de phenyloxazole et fongicides a usage agricole et horticole Download PDF

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Publication number
WO2001087857A1
WO2001087857A1 PCT/JP2001/004075 JP0104075W WO0187857A1 WO 2001087857 A1 WO2001087857 A1 WO 2001087857A1 JP 0104075 W JP0104075 W JP 0104075W WO 0187857 A1 WO0187857 A1 WO 0187857A1
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WO
WIPO (PCT)
Prior art keywords
group
alkyl
substituted
alkyl group
alkoxy
Prior art date
Application number
PCT/JP2001/004075
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English (en)
Japanese (ja)
Inventor
Akiyoshi Ueda
Yasushi Kubota
Shigemi Suga
Hiroshi Sano
Hiroshi Hamamura
Original Assignee
Nippon Soda Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Soda Co., Ltd. filed Critical Nippon Soda Co., Ltd.
Priority to AU2001256765A priority Critical patent/AU2001256765A1/en
Publication of WO2001087857A1 publication Critical patent/WO2001087857A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Definitions

  • 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.
  • the phenyloxazole compound similar to the compound of the present invention includes a compound represented by the general formula:
  • 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
  • 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.
  • n 0, 1 or 2
  • X and Y may be the same or different.
  • C 4 two Y - 5 may form an alkylene.
  • 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.
  • 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-Puchiru
  • 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 but
  • 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 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
  • 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.
  • hetero ring of Y and RL examples include a 5- or 6-membered heterocyclic group containing oxygen, sulfur or nitrogen as a hetero atom, and are preferably an unsaturated heterocyclic group.
  • 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.
  • 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)
  • 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.
  • 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 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.
  • organic bases such as phosphorus oxychloride and triethylamine, and halogenated hydrocarbons such as chloroform are preferable.
  • Examples of the solvent used in this reaction include aromatic hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as dichloromethane and chloroform.
  • 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.
  • 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.
  • 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 1,2-dimethoxetane
  • Examples of the base used include alkali metal hydrides, carbonates of alkali metals, and organic bases such as triethylamine.
  • 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.
  • solvent used in this reaction examples include aromatic hydrocarbons such as benzene and toluene.
  • 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.
  • the dehydrating agent used in this reaction include dicyclohexylcarbodiimid And 3- (3-dimethylaminopropyl) -1-ethylcarbodimid hydrochloride.
  • the solvent used in these reactions include aromatic hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as dichloromethane and chloroform.
  • 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 i n e r e a)
  • 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 l3 ⁇ 4 (P y r i c u l a r i a o r y z a e)
  • Bentgrass snow rot sclerotiniaborealis Bentgrass snow rot sclerotiniaborealis, o-chardgrass powdery mildew (Erysiphegr am inis), soybean purpura (Cercosporaki ku chii), potato 'tomato plague (Phyt 0 ⁇ hthorainfestans). And disease (P seudoperonosporac ub ensis),
  • Grape downy mildew (P la smo paraviticola) It can be used for pest control.
  • 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.
  • gray mold fungus Botrytiscinerea
  • sugar beet brown spot Cercosporabeticola
  • apple black spot Venturiainae qu alis
  • the compound of the present invention is effective against 1a) as well as the susceptible bacteria.
  • 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.
  • gray mold fungi Botryticincinerea
  • dicarboximide fungicides eg, vinclozolin, procymidone, iprodione
  • 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.
  • the compound of the present invention can be used as an antibacterial and antifungal agent for walls and bathtubs, or shoes and clothes.
  • 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 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.
  • various fungicides, insecticides, acaricides, and plant growth regulators that can be used by mixing with the compound of the present invention are shown below.
  • Permethrin Cypermethrin, Deltamethrin, Fuembrelet, Fenprohatrin, Pyrethrin, Arlesrin, Tetramethrin, Resmethrin, Dimethrin, Probasulin, Phunotrin, Protrin, Fluvalinate, Cyflutrin -Cyhalothrin, flucitrinate, etofenprox, cycloprotrin, tralomethrin, silafluofen, profenprox, acrinasulin, etc.
  • Nematicide Nematicide:
  • 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). .
  • 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.
  • Test example 3 Wheat powdery mildew control test (prevention test)

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des composés de phényloxazole représentés par la formule générale (I) ou leurs sels, lesquels composés peuvent être synthétisés pour un avantage industriel et sont utiles en tant que fongicides à usage agricole et horticole. Ces composés présentent des effets fongicides excellents non seulement sur les champignons pathogènes sensibles aux fongicides de l'état de la technique antérieure, mais également sur les champignons pathogènes qui y résistaient. Selon cette formule (I), X représente halogéno, nitro, cyano, alkyle C1-6, ou similaire; Y représente halogéno, cyano, nitro, alkyle C1-12, ou similaire; Z représente O, S, SO, SO2, ou N-R2; R1 représente hydrogène, alkyle C1-6, cycloalkyle C3-7, ou similaire; R2 représente hydrogène ou alkyle C1-6, ou R2 avec N-R1 peut former un anneau; m vaut un entier de 0 à 2; et n vaut un entier de 0 à 3.
PCT/JP2001/004075 2000-05-16 2001-05-16 Composes de phenyloxazole et fongicides a usage agricole et horticole WO2001087857A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001256765A AU2001256765A1 (en) 2000-05-16 2001-05-16 Phenyloxazole compounds and fungicides for agricultural and horticultural use

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2000143924 2000-05-16
JP2000-143924 2000-05-16

Publications (1)

Publication Number Publication Date
WO2001087857A1 true WO2001087857A1 (fr) 2001-11-22

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7994185B2 (en) 2008-05-06 2011-08-09 Glaxo Smith Kline LLC Benzene sulfonamide thiazole and oxazole compounds
US8435999B2 (en) 2007-08-13 2013-05-07 Monsanto Technology Llc Compositions and methods for controlling nematodes
EP4173485A1 (fr) * 2021-10-27 2023-05-03 Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. Composés inhibant l'agrégation de protéine pour la lutte contre les maladies des plantes

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0237929A1 (fr) * 1986-03-11 1987-09-23 F. Hoffmann-La Roche Ag Dérivés du pyrocatéchol substitués en 3,5
JPH0665210A (ja) * 1992-08-12 1994-03-08 Teijin Ltd ２―フェニル複素環式化合物
EP0712847A1 (fr) * 1993-08-11 1996-05-22 Nippon Soda Co., Ltd. Derive d'imidazole et son procede de production, et substance anti-nuisibles

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0237929A1 (fr) * 1986-03-11 1987-09-23 F. Hoffmann-La Roche Ag Dérivés du pyrocatéchol substitués en 3,5
JPH0665210A (ja) * 1992-08-12 1994-03-08 Teijin Ltd ２―フェニル複素環式化合物
EP0712847A1 (fr) * 1993-08-11 1996-05-22 Nippon Soda Co., Ltd. Derive d'imidazole et son procede de production, et substance anti-nuisibles

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
SINGH SUDHIR K. ET AL.: "Studies in antiparasitic agents: part 13 synthesis of 4-aryl-2-substitutedaminothiazoles as potential anthelmintics", INDIAN J. CHEMICAL, SECT B, vol. 28B, no. 9, 1989, pages 86 - 89, XP002944756 *

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10375958B2 (en) 2007-08-13 2019-08-13 Monsanto Technology Llc Compositions and methods for controlling nematodes
US8435999B2 (en) 2007-08-13 2013-05-07 Monsanto Technology Llc Compositions and methods for controlling nematodes
US9125410B2 (en) 2007-08-13 2015-09-08 Monsanto Technology Llc Compositions and methods for controlling nematodes
US9420788B2 (en) 2007-08-13 2016-08-23 Monsanto Technology Llc Compositions and methods for controlling nematodes
US9642364B2 (en) 2007-08-13 2017-05-09 Monsanto Technology Llc Compositions and methods for controlling nematodes
US10112930B2 (en) 2007-08-13 2018-10-30 Monsanto Technology Llc Compositions and methods for controlling nematodes
US10827753B2 (en) 2007-08-13 2020-11-10 Monsanto Technology Llc Compositions and methods for controlling nematodes
US8415345B2 (en) 2008-05-06 2013-04-09 Glaxo SmithKline LLC Benzene sulfonamide thiazole and oxazole compounds
US8642759B2 (en) 2008-05-06 2014-02-04 Glaxosmithkline Llc Benzene sulfonamide thiazole and oxazole compounds
US9233956B2 (en) 2008-05-06 2016-01-12 Novartis Ag Benzene sulfonamide thiazole and oxazole compounds
US7994185B2 (en) 2008-05-06 2011-08-09 Glaxo Smith Kline LLC Benzene sulfonamide thiazole and oxazole compounds
EP4173485A1 (fr) * 2021-10-27 2023-05-03 Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. Composés inhibant l'agrégation de protéine pour la lutte contre les maladies des plantes
WO2023073115A1 (fr) * 2021-10-27 2023-05-04 MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. Composés inhibant l'agrégation de protéines pour la lutte contre les maladies des plantes

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