WO1999059993A1 - Compose heterocyclique - Google Patents

Compose heterocyclique Download PDF

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Publication number
WO1999059993A1
WO1999059993A1 PCT/JP1999/002515 JP9902515W WO9959993A1 WO 1999059993 A1 WO1999059993 A1 WO 1999059993A1 JP 9902515 W JP9902515 W JP 9902515W WO 9959993 A1 WO9959993 A1 WO 9959993A1
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WO
WIPO (PCT)
Prior art keywords
compound
parts
present
pests
formula
Prior art date
Application number
PCT/JP1999/002515
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English (en)
Japanese (ja)
Inventor
Koichi Sugihara
Michihiko Fujinami
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 AU37306/99A priority Critical patent/AU3730699A/en
Publication of WO1999059993A1 publication Critical patent/WO1999059993A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/82—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 three ring hetero atoms

Definitions

  • the present invention relates to a heterocyclic compound, a pesticide (Pesticide) containing the heterocyclic compound as an active ingredient, and a pest controlling method using the heterocyclic compound.
  • Pesticide pesticide
  • the compound of the present invention has the formula (II)
  • the ring closure reaction is usually performed in a solvent, the reaction temperature is usually from 40 to 200 ° C, and the reaction time is usually from 1 to 30 hours.
  • the solvent examples include protic polar solvents such as methanol, ethanol, and acetic acid, nitriles such as acetonitrile, aprotic polar solvents such as dioxane, and a mixed solvent thereof.
  • the compound of the present invention represented by the formula (I) can be obtained by performing ordinary post-treatment operations such as neutralization, extraction with an organic solvent, and concentration.
  • the compound can be further purified by recrystallization, column chromatography or the like, if necessary.
  • the compound represented by the formula ( ⁇ ) has the formula ( ⁇ )
  • the reaction is usually carried out in a solvent, and the reaction temperature is usually in the range of 120 to 30 ° C.
  • the reaction time usually ranges from 0.2 to 5 hours.
  • the solvent examples include protic polar solvents such as methanol, ethanol, acetic acid, and water; ethers such as tetrahydrofuran and dioxane; halogenated hydrocarbons such as methylene chloride and chloroform; nitriles such as acetonitrile; A mixed solvent is mentioned.
  • protic polar solvents such as methanol, ethanol, acetic acid, and water
  • ethers such as tetrahydrofuran and dioxane
  • halogenated hydrocarbons such as methylene chloride and chloroform
  • nitriles such as acetonitrile
  • a mixed solvent is mentioned.
  • the amount of the reagent used in the reaction is such that 1 mol of the compound represented by the formula ( ⁇ ) is 1 to 3 mol of the hydroxylamine or its hydrochloride.
  • a base in an approximately equimolar amount to the hydrochloride.
  • bases include, for example, tertiary amines such as trimethylamine, triethylamine and pyridine; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium methoxide And alkali metal alkoxides such as sodium ethoxide.
  • the compound represented by the formula (II) can be obtained by performing ordinary post-treatment operations such as neutralization, extraction with an organic solvent, and concentration.
  • the compound can be further purified, if necessary, by recrystallization, column chromatography or the like.
  • the compound can be produced by reacting a compound represented by the following formula:
  • the reaction is usually carried out without a solvent or in a solvent, the reaction temperature is usually from 10 to 180 ° C, and the reaction time is usually from 1 to 30 hours.
  • the solvent examples include ethers such as getyl ether, tetrahydrofuran, and dioxane; halogenated hydrocarbons such as methylene chloride and chloroform; aromatic hydrocarbons such as benzene and toluene; nitriles such as acetonitrile; And the like.
  • ethers such as getyl ether, tetrahydrofuran, and dioxane
  • halogenated hydrocarbons such as methylene chloride and chloroform
  • aromatic hydrocarbons such as benzene and toluene
  • nitriles such as acetonitrile
  • the ratio of the reagents used in the reaction is such that the compound represented by the formula (V) is 1 to 3 mol per 1 mol of the compound represented by the formula (IV).
  • the compound represented by the formula (III) can be obtained by performing ordinary post-treatment operations such as concentration.
  • the compound can be further purified, if necessary, by recrystallization, column chromatography or the like.
  • the compound represented by the formula (IV) is obtained by producing trifluoroacetoacetate from monoethyl malonate and trifluoroacetyl chloride (Org. Synth., 61, 5-8 (1982)). Then, it can be produced from the trifluoroacetoacetate ester and ⁇ -cyanoacetamide in four steps (J. Org. Chem., 25, 560-564 (1968) or J. Medicinal Chem., 10). , 149-154 (1967)).
  • Examples of the pests to which the compound of the present invention can exhibit a controlling effect include the following harmful arthropods.
  • Hemiptera Insects such as Brown-footed Deer (Laodelphax stnatellus), Brown-tailed Deer (Nilaparvata lugens), Singing Ground Beetle (Sogatella furcife), etc .; Aphis gossypii), aphids such as peach aphids, Myzus persicae, stink bugs, on-spot whitefly (T ialeurodes vaporariorum), evening whiteflies Bemisia tabaci), silver leaf whiteflies Bemisia argentifolli, whiteflies and others Gunbugs, lice, etc.
  • Insects such as Brown-footed Deer (Laodelphax stnatellus), Brown-tailed Deer (Nilaparvata lugens), Singing Ground Beetle (Sogatella furcife), etc .
  • Aphis gossypii) aphids
  • Coleoptera pests Corn-related worms such as Western corn relay worms (Diabrotica virgifera virgifera) and Southern corn worms, Diabrotica undecimpunctata howardi, AnomaJa cuprea, and Anomala rufocuprea (Sitophilus zeamais), Rice Lentil Lssorhoptrus oryzophilus, Anole Fanolef (Hypera pastica), Azosomushi (Callosobruch uys Kunststoffensis), etc.
  • Western corn relay worms Diabrotica virgifera virgifera
  • Southern corn worms Diabrotica undecimpunctata howardi, AnomaJa cuprea, and Anomala rufocuprea (Sitophilus zeamais), Rice Lentil Lssorhoptrus oryzophilus, Anole Fanolef (Hypera pastica), Azosomushi (Callosobruch uys Kunststoffen
  • Thistle pests Thrips palmiflora TTuips palmi), Negisama Thdps tabaci), H. thrips ⁇ ⁇ hawaiiensis, etc .;
  • Hymenoptera pests scabies such as scabies, sparrows, stag bees, and the beetle Athe ia japonicd
  • Orthopterous pests keratoids, bats, etc.
  • Pteratophyte pests Wild flea Pulex irritans, etc.
  • Termite pests Sphagnum termites Reticulitennes speratus), termites Coptotermes formosanus) Temple
  • the compound of the present invention is also effective against the above harmful insects which are resistant to commercially available insecticides such as organophosphorus agents, carbamate agents and pyrethroid agents.
  • insecticides such as organophosphorus agents, carbamate agents and pyrethroid agents.
  • the compound of the present invention may be used as it is without adding any other components.
  • compositions usually contain the compound of the present invention as an active ingredient in an amount of 0.01 to 95% by weight.
  • solid carrier used in such formulation examples include clays (such as clay ore clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, fubasami clay, acid clay), talc, ceramics, and other inorganic minerals (cericite). , Quartz, sulphate, activated carbon, calcium carbonate, hydrated silica, etc.) and fine powders or granules such as chemical fertilizers (ammonium sulphate, phosphorous ammonium, ammonium nitrate, urea, salt acetic acid, etc.).
  • clays such as clay ore clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, fubasami clay, acid clay), talc, ceramics, and other inorganic minerals (cericite).
  • fine powders or granules such as chemical fertilizers (ammonium sulphate, phosphorous ammonium, ammonium n
  • water For example, water, alcohols (methanol, ethanol, etc.), ketones (aceton, methyl ethyl ketone, etc.), hydrocarbons (benzene, toluene, xylene, ethylbenzene, methyl naphthylene, hexane, cyclohexane, kerosene, Light oil, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonit , Ethers (diisopropyl ether, dioxane, etc.), acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (E.g., dichloromethane, trichloroethane, carbon tetrachloride, etc.), dimethyl sulfoxide, vegetable oils such as soybean oil, cottonseed oil and the like.
  • hydrocarbons
  • gaseous carrier that is, the propellant, such as freon gas, butane gas, LPG (liquefied petroleum gas) ), Dimethyl ether, carbon dioxide and the like.
  • the propellant such as freon gas, butane gas, LPG (liquefied petroleum gas)
  • Dimethyl ether carbon dioxide and the like.
  • surfactants include, for example, alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and their polyoxyethylenates, polyethylene glycol ethers, polyhydric alcohols Esters, sugar alcohol derivatives and the like.
  • adjuvants for preparations such as fixatives and dispersants
  • adjuvants for preparations include casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, saccharides, synthetic water-soluble polymers ( Polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.).
  • stabilizers include PAP (isopropyl acid phosphate) and BHT (2,6-di-tert-butyl-4-methylphenol).
  • BHA a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol
  • vegetable oils mineral oils, surfactants, fatty acids or esters thereof, and the like.
  • self-combustion type smoke agents include nitrates, nitrites, guanidine salts, potassium chlorate, nitrocellulose, ethylcellulose, wood flour, etc., heating agents, alkali metal salts, alkaline earth metal salts, heavy chromium Thermal decomposition stimulants such as acid salts and chromates, oxygen supply agents such as nitric acid lime, flame retardants such as melamine and wheat starch, fillers such as diatomaceous earth, binders such as synthetic paste, etc.
  • Examples of base materials for chemical reaction type smokers include exothermic agents such as sulfides, polysulfides, hydrosulfides, hydrated salts and calcium oxide of alkali metals, catalysts such as carbonaceous materials, iron carbide, and activated clay. Agents, azodicarbonamide, benzenesulfonylhydrazide, dinitrosopentamethylenetetramine, organic foaming materials such as polystyrene and polyurethane, and fillers such as natural fiber fragments and synthetic fiber fragments.
  • bait baits include bait ingredients such as cereal flour, vegetable oil, sugar, and crystalline cellulose; antioxidants such as dibutylhydroxytoluene and nordihydroguairetic acid; preservatives such as dehydroacetic acid; and capsicum powder.
  • bait ingredients such as cereal flour, vegetable oil, sugar, and crystalline cellulose
  • antioxidants such as dibutylhydroxytoluene and nordihydroguairetic acid
  • preservatives such as dehydroacetic acid
  • capsicum powder examples include food inhibitors, cheese flavors, evening onion flavors, and attractants such as peanut oil.
  • Formulations of flowables generally contain 1 to 75% of the compound of the present invention in 0.5 to 15% dispersant, 0.1 to 10% suspending aid.
  • Agents eg, compounds that impart protective colloid thixotropy
  • appropriate adjuvants eg, antifoaming agents, antioxidants, stabilizers, spreading agents, penetration aids
  • Frozen Microbial dispersion in water containing an inhibitor, a fungicide, a fungicide, etc. instead of water, an oil in which the compound hardly dissolves can be used as a suspension in oil.
  • the protective colloid for example, gelatin, casein, gums, cellulose ether, polyvinyl alcohol and the like are used.
  • the compound imparting thixotropy include bentonite, aluminum magnesium silicate, xanthan gum, polyacrylic acid and the like.
  • the preparation thus obtained is used as it is or diluted with water or the like.
  • the compound of the present invention or a preparation thereof may be used in combination with other insecticides, nematicides, acaricides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil improvers, animal feeds, etc. It can also be used in combination with or without mixing.
  • the application rate is usually in the range of 100 to 100 g, preferably 100 to 100 g per hectare. Range.
  • the application concentration is usually 10 to 100 ppm, and granules, powders, etc. are applied as they are.
  • these formulations may be sprayed on foliage of plants such as crops to be protected from pests. By treating these preparations with soil, pests living in the soil can be controlled, and pests in the foliage of plants such as crops can be controlled at the same time.
  • emulsions, wettable powders, flowables, etc. are usually diluted with water to 0.01 to 100 ppm and applied. Aerosols, smokers, ULVs, poison baits, etc. should be applied as they are.
  • Dioxane was distilled off under reduced pressure, 10 ml of water was added to the residue, and then potassium carbonate powder was added under cooling with an ice-water bath to adjust the pH to pH8 to pH7. This was extracted twice with ethyl acetate, and the organic layer was washed with 10% saline and dried over magnesium sulfate. After magnesium sulfate is filtered off, the solvent is distilled off under reduced pressure. After that, 0.357 g (yield: 80.2%) of N 2 -hydroxy-1-N 1- (4-trifluoromethylviridine-13-force ruponyl) formamidine was obtained.
  • N 2 -Hydroxy-1-N 1- (4-trifluoromethylviridine-13-carbonyl) formamidine was suspended in 15 ml of dioxane at room temperature, and 15 ml of acetic acid was added dropwise. This mixed solution was heated and stirred at 100 ° C. for about 4 hours. Dioxane was distilled off under reduced pressure, 50 ml of water was added to the residue, and then carbonated lithium powder was added under ice-water bath cooling to adjust the solution to pH 7-8.
  • 1 part of the compound of the present invention is dissolved in an appropriate amount of acetone, and 5 parts of synthetic hydrous silicon oxide fine powder, 0.3 part of PAP and 93.7 parts of clay are added thereto, followed by stirring and mixing with a juice mixer. Then, the acetone is removed by evaporation to obtain 1% powder.
  • 10 parts of the compound of the present invention is added to 40 parts of an aqueous solution containing 6 parts of polyvinyl alcohol, and dispersed by stirring with a mixer. To this was added 40 parts of an aqueous solution containing 0.5 part of xanthangum and 0.1 part of aluminum magnesium silicate, and 10 parts of propylene glycol was added, followed by gentle stirring and mixing. Get a% flowable.
  • 0.1 part of the compound of the present invention is dissolved in 5 parts of xylene and 5 parts of trichloride and mixed with 89.9 parts of deodorized kerosene to obtain a 0.1% oil solution.
  • a valve part attach a valve part, and 40 parts of propellant (liquefied petroleum gas) under pressure to obtain aqueous aerosol
  • Test example 1 Insecticidal test against aphid (Foliage spray test)
  • the emulsion of the test compound obtained according to Formulation Example 1 was diluted with water so that the active ingredient concentration became 500 ppm.
  • the first true leaf of a cucumber planted in a polyethylene cup with the first true leaf unfolded was inoculated with 20 Aphid aphids.
  • the diluent was applied at a rate of 20 ml / cup to the cucumber planted with the aphid parasitism.
  • the compound of the present invention exhibited a control value of 90% or more.
  • Test Example 2 Insecticidal test against aphid
  • the emulsion of the test compound obtained according to Formulation Example 1 was diluted with water so that the active ingredient concentration became 500 ppm.
  • the diluted solution was irrigated at a rate of 5 ml / l pot to a root of a lily plant planted in a polyethylene cup.
  • Five days after drug treatment, 20 aphids were released on the true leaves, and 7 days after release, the control value was determined by the same formula as used in Test Example 1.
  • the compound of the present invention exhibited a control value of 90% or more.

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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 se rapporte au 5-(4-trifluorométhylpyridine-3-yle)-1,2,4-oxadiazole, à un agent pesticide contenant ce composé en tant que principe actif et à une méthode de lutte antiparasitaire faisant usage dudit composé.
PCT/JP1999/002515 1998-05-18 1999-05-13 Compose heterocyclique WO1999059993A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU37306/99A AU3730699A (en) 1998-05-18 1999-05-13 Heterocyclic compound

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP13547498 1998-05-18
JP10/135474 1998-05-18

Publications (1)

Publication Number Publication Date
WO1999059993A1 true WO1999059993A1 (fr) 1999-11-25

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PCT/JP1999/002515 WO1999059993A1 (fr) 1998-05-18 1999-05-13 Compose heterocyclique

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AU (1) AU3730699A (fr)
WO (1) WO1999059993A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000035285A1 (fr) * 1998-12-17 2000-06-22 Aventis Cropscience Gmbh 4-haloalkyl-3-heterocyclylpyridines et 4-haloalkyl-5-heterocyclylpyrimidines et leur utilisation comme repulsifs
WO2001014373A1 (fr) * 1999-08-20 2001-03-01 Syngenta Participations Ag Derives de trifluoromethylpyri(mi)dine
WO2002048111A2 (fr) * 2000-12-13 2002-06-20 Bayer Cropscience Gmbh Procede de fabrication de 4-haloalkyl-nicotine-nitriles
US8017632B2 (en) 2004-07-20 2011-09-13 Bayer Cropscience Ag Selective insecticides based on haloalkylnicotinic acid derivatives, anthranilic acid diamides, or phthalic acid diamides and safeners

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998057969A1 (fr) * 1997-06-16 1998-12-23 Hoechst Schering Agrevo Gmbh 4-haloalkyl-3- heterocyclylpyridines et 4-haloalkyl -5-heterocyclylpyrimidines, leurs procedes de preparation, produits les contenant et leur utilisation comme pesticides

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998057969A1 (fr) * 1997-06-16 1998-12-23 Hoechst Schering Agrevo Gmbh 4-haloalkyl-3- heterocyclylpyridines et 4-haloalkyl -5-heterocyclylpyrimidines, leurs procedes de preparation, produits les contenant et leur utilisation comme pesticides

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000035285A1 (fr) * 1998-12-17 2000-06-22 Aventis Cropscience Gmbh 4-haloalkyl-3-heterocyclylpyridines et 4-haloalkyl-5-heterocyclylpyrimidines et leur utilisation comme repulsifs
WO2001014373A1 (fr) * 1999-08-20 2001-03-01 Syngenta Participations Ag Derives de trifluoromethylpyri(mi)dine
WO2002048111A2 (fr) * 2000-12-13 2002-06-20 Bayer Cropscience Gmbh Procede de fabrication de 4-haloalkyl-nicotine-nitriles
WO2002048111A3 (fr) * 2000-12-13 2003-03-27 Bayer Cropscience Gmbh Procede de fabrication de 4-haloalkyl-nicotine-nitriles
US6864385B2 (en) 2000-12-13 2005-03-08 Aventis Cropscience Gmbh Process for the preparation of 4-haloalkylnicotinonitriles
KR100845376B1 (ko) * 2000-12-13 2008-07-09 바이엘 크롭사이언스 게엠베하 4-할로알킬 니코틴 니트릴의 제조 방법
US8017632B2 (en) 2004-07-20 2011-09-13 Bayer Cropscience Ag Selective insecticides based on haloalkylnicotinic acid derivatives, anthranilic acid diamides, or phthalic acid diamides and safeners
US8685985B2 (en) 2004-07-20 2014-04-01 Bayer Cropscience Ag Selective insecticides based on anthranilic acid diamides and safeners
US8841328B2 (en) 2004-07-20 2014-09-23 Bayer Cropscience Ag Selective insecticides based on anthranilic acid diamides and safeners

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Publication number Publication date
AU3730699A (en) 1999-12-06

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