WO1996038425A1 - Derives de triazolone, leur utilisation, et intermediaires pour leur preparation - Google Patents

Derives de triazolone, leur utilisation, et intermediaires pour leur preparation Download PDF

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Publication number
WO1996038425A1
WO1996038425A1 PCT/JP1996/001434 JP9601434W WO9638425A1 WO 1996038425 A1 WO1996038425 A1 WO 1996038425A1 JP 9601434 W JP9601434 W JP 9601434W WO 9638425 A1 WO9638425 A1 WO 9638425A1
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WO
WIPO (PCT)
Prior art keywords
compound
triazolone
formula
general formula
methyl
Prior art date
Application number
PCT/JP1996/001434
Other languages
English (en)
Japanese (ja)
Inventor
Tadashi Ohsumi
Taro Hirose
Kazuya Ujihara
Rei Matsunaga
Original Assignee
Sumitomo Chemical Company, Limited
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 Sumitomo Chemical Company, Limited filed Critical Sumitomo Chemical Company, Limited
Priority to AU57812/96A priority Critical patent/AU5781296A/en
Publication of WO1996038425A1 publication Critical patent/WO1996038425A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the present invention relates to a triazolone derivative, its use, and its production intermediate.
  • the present invention provides a compound represented by the general formula (I):
  • X represents a methyl group or a halogen atom
  • Y and Z are the same or different and represent a hydrogen atom, a methyl group or a halogen atom.
  • a plant disease controlling agent characterized by containing the triazolone derivative (hereinafter, referred to as the compound of the present invention) as an active ingredient.
  • the present invention further provides a compound of the general formula ( ⁇ ) (I)
  • the halogen atom represented by X, Y or Z includes a chlorine atom, a bromine atom And a fluorine atom.
  • the triazolone compound of the general formula ( ⁇ ) and / or the triazolone compound of the general formula ( ⁇ ) preferred embodiments thereof include:
  • the compound of the present invention is, for example, a triazolone compound represented by the general formula ( ⁇ ) and usually 0.5 to 10 equivalents of methanol or an alkali metal salt thereof (sodium salt, potassium salt or lithium salt). ) And, if necessary, in the presence of a base, usually in a solvent, usually at a temperature of 20 ° C to 200 ° C. Can be.
  • Solvents that can be used vary depending on the type of alkali metal salt used and the type of base used.
  • examples include aliphatic hydrocarbons such as hexane, heptane, lignin, petroleum ether, benzene, toluene, and xylene.
  • ethers such as dimethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, etc.
  • Examples of usable bases include inorganic bases such as sodium hydroxide, hydroxide hydroxide, sodium carbonate, carbonate carbonate, sodium hydride and the like, and alkali metal methoxide such as sodium methoxide.
  • reaction solution After completion of the reaction, the reaction solution is subjected to ordinary post-treatments such as extraction with an organic solvent, concentration, and the like, and if necessary, further purification by chromatography, recrystallization, or the like, to isolate the compound of the present invention.
  • the compound of the present invention comprises a triazolone compound represented by the above general formula ( ⁇ ), and usually 0.5 to 5 equivalents thereof.
  • Solvents that can be used vary depending on the type of raw materials and bases used, but for example, aliphatic hydrocarbons such as hexane, heptane, lignin, petroleum ether, and aromatic hydrocarbons such as benzene, toluene, and xylene.
  • Halogenated hydrocarbons such as hydrogen, carbon form, carbon tetrachloride, dichloroethane, carbon benzene, dichlorobenzene, ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, acetone, methyl ethyl ketone, methyl Ketones such as isobutyl ketone, isophorone, cyclohexanone, methanol, ethanol, isopropanol, t-butanol, octanol, cyclohexanol, methyl sorb, methylene glycol, glycer Alcohols such as ethylene, esters such as ethyl formate, ethyl acetate, butyl acetate, and getyl carbonate; nitrated compounds such as nitroethane and nitrobenzene; nitriles such as
  • Examples of usable bases include, for example, inorganic bases such as sodium hydroxide, potassium oxide, sodium carbonate, potassium carbonate and sodium hydride, and alkali metal methoxides such as sodium methoxide.
  • reaction solution After completion of the reaction, the reaction solution is subjected to ordinary post-treatments such as extraction with an organic solvent, concentration, and the like, and if necessary, further purification by chromatography, recrystallization, or the like, to isolate the compound of the present invention.
  • the triazolone compound of the general formula (m) can be produced, for example, according to the method described in Production Example 2 of the intermediate described below.
  • the compound of the present invention When used as an active ingredient of a plant disease controlling agent, it may be used as it is without adding any other components.However, it is usually mixed with a solid carrier, a liquid carrier, a surfactant and other auxiliary agents for formulation. Into emulsions, wettable powders, suspensions, granules, powders, liquids, etc.
  • These preparations usually contain the compound of the present invention as an active ingredient in a weight ratio of 0.1 to 95%, preferably 1 to 90%.
  • the solid carrier examples include fine powders and granular materials such as kaolin clay, atta plargite clay, bentonite, acid clay, pyrophyllite, tanolek, diatomaceous earth, calcite, knollemi powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide.
  • Liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol and cellosol, ketones such as acetone, cyclohexanone and isophorone, soybean oil, cottonseed oil and the like.
  • Vegetable oils dimethyl sulfoxide, acetonitrile, water and the like can be mentioned.
  • Surfactants used for emulsification, dispersion, wetting, etc. include alkyl sulfates, alkyl (aryl) sulfates.
  • Anionic surfactants such as sulfonic acid salts, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphate ester salts, polyoxyethylene alkyl ether, polyoxy ethylene alkyl aryl ether, polyoxyethylene polyoxypropylene block copolymer
  • non-ionic surfactants such as sorbitan fatty acid esters and polyoxyethylene sorbitan fatty acid esters.
  • Pharmaceutical adjuvants include ligninsulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethylcellulose), PAP (acidic isopropyl phosphate) and the like.
  • formulations may be used as they are or diluted with water and sprayed on foliage, or may be used in various forms such as dusting, granulating and mixing with soil, or applying to soil.
  • it by using it in combination with other plant disease controlling agents, it is expected that the controlling effect is enhanced.
  • it can be used in combination with insecticides, acaricides, nematicides, herbicides, plant growth regulators, fertilizers, and soil conditioners.
  • the compound of the present invention can be used as an active ingredient of a plant disease controlling agent for paddy fields, fields, orchards, tea fields, pastures, lawns, and the like.
  • the application rate is usually from 0.1 g to 50 g, preferably from 0.05 g to 20 g, per arel, emulsion and water.
  • the application concentration is usually 0.0001% to 0.5%, preferably 0.0005% to 0.2%. Preparations, dusts, etc. are applied without dilution.
  • Me represents a methyl group
  • mp represents a melting point
  • 1,1-Dimethyl-1- (2,6-dimethylphenyl) semicarbazide A solution of 2.07 g (10.0 fractions ol) of dioxane in bis (trichloromethyl) carbonate [triphosgene] 3.00 g (10.0 mols) is added to 100 ml of dioxane. The solution was dropped at 5 ° C or less. After completion, the mixture was stirred at the same temperature for 30 minutes and then heated and stirred at a bath temperature of 65 for 6 hours. To the resulting reaction solution was added aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and concentrated to obtain 2.07 g (87% yield) of 1-methyl-3-chloro-4- (2,6-dimethylphenyl) -1,1,2,4-triazolone.
  • each of the compounds (1) to (8) of the present invention 25 parts of each of the compounds (1) to (8) of the present invention, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC and 69 parts of water are mixed, and the particle size of the active ingredient is 5 ⁇ m or less. To obtain each suspension.
  • Formulation Example 5 10 parts of the compounds (1) to (8) of the present invention, 1 part of polyoxyethylenestyrylphenyl ether and 89 parts of water are mixed to obtain each liquid preparation.
  • Test Examples show that the compound of the present invention is useful as an active ingredient of a plant disease controlling agent.
  • the compounds of the present invention are indicated by the compound numbers in Table 1.
  • the control efficacy was determined by visually observing the disease state of the test plant at the time of the survey, that is, the degree of the bacterial flora such as leaves and stems, and the extent of the lesions. If no bacterial flora or lesions were observed, 5 or 10% The test was conducted with a compound of "4" if it was recognized to a degree, "3" if it was about 30%, “2” if it was about 50%, "1” if it was about 70%, and more. If there is no difference from the onset state of the disease, there is no difference, and it is evaluated as “0” and evaluated on a 6-point scale.
  • Test example 1 Rice blast control test (preventive effect)
  • a plastic pot was filled with sandy loam, rice (Nipponbare) was sown, and grown in a greenhouse for 20 days. Thereafter, the test reagent prepared as a wettable powder according to Formulation Example 1 was diluted with water to a predetermined concentration, and the resulting solution was sprayed on foliage so as to sufficiently adhere to the rice leaf surface. After spraying, the plants were air-dried, sprayed with a spore suspension of the blast fungus, and inoculated. After inoculation, they were left at 28 ° C and high humidity for 6 days, and their control efficacy was examined. The results are shown in Table 3.
  • Test example 2 Rice sheath blight control test (preventive effect)
  • the test agent prepared as a wettable powder according to Formulation Example 1 was diluted with water to a predetermined concentration, and the resulting solution was sprayed on the foliage of the rice so as to sufficiently adhere to the leaf surface. After spraying, the plants were air-dried and inoculated with a bran culture mycelium of the sheath blight fungus at the root. After inoculation, the plants were placed at 28 ° C and in a humid environment for 4 days, and the control efficacy was examined. The results are shown in Table 3.
  • Plastic pots were filled with sandy loam, and wheat (Norin 73) was sown and grown in a greenhouse for 10 days.
  • the test agent prepared as an emulsion according to Formulation Example 2 was diluted with water to a predetermined concentration, and the resulting solution was sprayed with foliage so as to sufficiently adhere to the leaves of the wheat seedlings. After spraying, a spore suspension of wheat eye spot bacterium was inoculated to the root of the wheat and kept at 15 ° C and high humidity for 14 days, and the control effect was examined. The results are shown in Table 3.
  • Test Example 4 Wheat powdery mildew control test (Therapeutic effect)
  • Plastic pots were filled with sandy loam, and wheat (Norin 73) was sown and grown in a greenhouse for 10 days.
  • the wheat seedlings that had developed the second leaf were sprinkled with wheat powdery mildew and inoculated. After inoculation, grow in a greenhouse at 23 ° C for 3 days, dilute with water water to a prescribed concentration the suspension prepared as described in Formulation Example 4, and attach it sufficiently to the leaves of the wheat.
  • Foliage was sprayed as if to do. After spraying, they were grown for additional 7 days under lighting, and their control efficacy was investigated. The results are shown in Table 3.
  • Plastic pots were filled with sandy loam, sown with Kiuri (Sagami Hanjiro), and grown for 12 days in a greenhouse.
  • the test agent prepared as a wettable powder according to Formulation Example 1 was diluted with water to a predetermined concentration, and the resulting solution was sprayed on the foliage of the cucumber seedlings so as to sufficiently adhere to the leaves. After spraying, a spore suspension of Cucumber powdery mildew was inoculated. After inoculation, they were grown at 25 ° C under light for 7 days, and their control efficacy was examined. The results are shown in Table 3. Table 3
  • the compound of the present invention exhibits an excellent control effect on plant diseases, and can be used as a plant disease controlling agent.
  • the chlorotriazolone compound of the formula ( ⁇ ) or the triazolone compound of the formula ( ⁇ ) is an intermediate of the compound of the present invention. Available as

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

Abstract

Dérivés de triazolone de formule générale (I), agent de lutte contre les maladies des plantes ayant pour principe actif ce dérivé, et intermédiaires servant à la préparation des dérivés. Dans la formule (I), X représente méthyle ou halogéno, et Y et Z représentent chacun indépendamment H, méthyle ou halogéno. Les dérivés de triazolone de formule générale (I) ont une action de lutte très efficace contre les maladies des plantes.
PCT/JP1996/001434 1995-05-29 1996-05-28 Derives de triazolone, leur utilisation, et intermediaires pour leur preparation WO1996038425A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU57812/96A AU5781296A (en) 1995-05-29 1996-05-28 Triazolone derivatives, use thereof, and intermediates for t he preparation thereof

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP7/130526 1995-05-29
JP13052695 1995-05-29
JP8/98058 1996-04-19
JP8098058A JPH0948766A (ja) 1995-05-29 1996-04-19 トリアゾロン誘導体、その用途およびその製造中間体

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WO1996038425A1 true WO1996038425A1 (fr) 1996-12-05

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AU (1) AU5781296A (fr)
WO (1) WO1996038425A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998005652A2 (fr) * 1996-08-01 1998-02-12 E.I. Du Pont De Nemours And Company Amides cycliques arthropodicides et fongicides
WO1998023156A1 (fr) * 1996-11-26 1998-06-04 E.I. Du Pont De Nemours And Company Fongicides et arthropodicides a substitution methyle
WO1999005139A1 (fr) * 1997-07-21 1999-02-04 Basf Aktiengesellschaft 2-[pyrazolyl et triazolyl-3'-oxymethylene]-phenyl-isoxazolones, triazolones et tretrazolones utilisees comme pesticides et fongicides
US6200997B1 (en) 1998-02-05 2001-03-13 Basf Aktiengesellschaft Heterocyclyl-substituted phenyl compounds, processes and intermediates for their preparation and their use for controlling harmful fungi and animal pests
US6489487B1 (en) 1998-08-03 2002-12-03 Sumitomo Chemical Company, Limited Triazolone derivatives, use thereof, and intermediates therefor

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994004514A1 (fr) * 1992-08-26 1994-03-03 Fmc Corporation 2-[(4-phenoxymethyl heterocyclique)phenoxy]-alcanoates herbicides
WO1995014009A1 (fr) * 1993-11-19 1995-05-26 E.I. Du Pont De Nemours And Company Amides cycliques fongicides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994004514A1 (fr) * 1992-08-26 1994-03-03 Fmc Corporation 2-[(4-phenoxymethyl heterocyclique)phenoxy]-alcanoates herbicides
WO1995014009A1 (fr) * 1993-11-19 1995-05-26 E.I. Du Pont De Nemours And Company Amides cycliques fongicides

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998005652A2 (fr) * 1996-08-01 1998-02-12 E.I. Du Pont De Nemours And Company Amides cycliques arthropodicides et fongicides
WO1998005652A3 (fr) * 1996-08-01 1998-06-11 E I De Pount De Nemours And Co Amides cycliques arthropodicides et fongicides
WO1998023156A1 (fr) * 1996-11-26 1998-06-04 E.I. Du Pont De Nemours And Company Fongicides et arthropodicides a substitution methyle
WO1999005139A1 (fr) * 1997-07-21 1999-02-04 Basf Aktiengesellschaft 2-[pyrazolyl et triazolyl-3'-oxymethylene]-phenyl-isoxazolones, triazolones et tretrazolones utilisees comme pesticides et fongicides
US6200997B1 (en) 1998-02-05 2001-03-13 Basf Aktiengesellschaft Heterocyclyl-substituted phenyl compounds, processes and intermediates for their preparation and their use for controlling harmful fungi and animal pests
US6489487B1 (en) 1998-08-03 2002-12-03 Sumitomo Chemical Company, Limited Triazolone derivatives, use thereof, and intermediates therefor

Also Published As

Publication number Publication date
JPH0948766A (ja) 1997-02-18
AU5781296A (en) 1996-12-18

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