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WO2010074021A1 - Dérivé de 1-(1-chlorocyclopropyle)-2-(1h-1,2,4-triazole-1-yle)-2-propène-1-ole substitué, son procédé de production, et produit chimique employé en agriculture/horticulture et agent de protection des équipements industriels contenant celui-ci - Google Patents

Dérivé de 1-(1-chlorocyclopropyle)-2-(1h-1,2,4-triazole-1-yle)-2-propène-1-ole substitué, son procédé de production, et produit chimique employé en agriculture/horticulture et agent de protection des équipements industriels contenant celui-ci Download PDF

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Publication number
WO2010074021A1
WO2010074021A1 PCT/JP2009/071225 JP2009071225W WO2010074021A1 WO 2010074021 A1 WO2010074021 A1 WO 2010074021A1 JP 2009071225 W JP2009071225 W JP 2009071225W WO 2010074021 A1 WO2010074021 A1 WO 2010074021A1
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Prior art keywords
compound
triazol
propen
substituted
agricultural
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English (en)
Japanese (ja)
Inventor
篤史 伊藤
清 田之上
央由 今井
勝 森
留美 鈴木
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Kureha Corp
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Kureha Corp
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    • 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
    • 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 novel substituted 1- (1-chlorocyclopropyl) -2- (1H-1,2,4-triazol-1-yl) -2-propen-1-ol derivative, its production method and
  • the present invention relates to agricultural and horticultural chemicals and industrial material protective agents.
  • a variety of properties are conventionally required for agricultural and horticultural agents and industrial material protective agents used to protect plants and industrial materials from harmful microorganisms.
  • agricultural and horticultural chemicals are required to be low in toxicity to human livestock and excellent in handling safety, to exhibit a high control effect against a wide range of plant diseases and to be excellent in sustainability.
  • the agricultural and horticultural agents are also desired to have a plant growth regulating effect that increases the yield by controlling the growth of various agricultural crops and horticultural plants to enhance the quality.
  • a wider spectrum is required for industrial material protective agents.
  • “Substituted 2- (1H-1,2,4-triazol-1-yl) -2-propen-1-ol derivatives” have heretofore been known compounds exhibiting bactericidal activity and plant growth regulating effects.
  • Patent Document 1 contains a substituted 2- (1H-1,2,4-triazol-1-yl) -2-propen-1-ol derivative as an azole compound represented by a predetermined general formula A disinfectant is disclosed (see claim 3, etc.).
  • Patent Document 2 discloses substituted 2- (1H-1,2,4-triazol-1-yl) -2-propen-1-ol as a triazolylpropenol derivative represented by a predetermined general formula.
  • a fungicide or plant growth regulator composition containing a derivative is disclosed (see claim 14 of the document).
  • Patent Document 2 discloses “substituted 1- (cycloalkyl) -2- (1H--) as a substituted 2- (1H-1,2,4-triazol-1-yl) -2-propen-1-ol derivative. 1,2,4-triazol-1-yl) -2-propen-1-ol derivatives ”.
  • the literature mentions a wide range of substituents as substituents on the cycloalkyl ring of this derivative.
  • substituted 1- (cycloalkyl) -2 having a chlorine atom at the 1-position of the cycloalkyl ring (cyclopropyl group) -(1H-1,2,4-triazol-1-yl) -2-propen-1-ol derivatives are not exemplified.
  • the substituted 1- (cycloalkyl) -2- (1H-1,2,4-triazol-1-yl) -2-propen-1-ol derivatives studied in the examples of the literature are cycloalkyl Only compounds having an alkyl substituent (methyl group or ethyl group) at the 1-position of the ring (cyclopropyl group).
  • the present invention is a novel compound capable of imparting desirable properties to agricultural and horticultural chemicals and industrial material protective agents, exhibiting excellent agricultural and horticultural disease controlling effects, plant growth regulating effects and industrial material protective effects
  • the main purpose is to provide
  • the present inventors have conducted a detailed study on the chemical structure and physiological activity of 2- (1H-1,2,4-triazol-1-yl) -2-propen-1-ol derivatives.
  • the inventors have found that the compounds of the present invention represented by the following general formula (I) have excellent physiological activity, and have completed the present invention. That is, the present invention relates to substituted 1- (1-chlorocyclopropyl) -2- (1H-1,2,4-triazol-1-yl) -2-propene-1 represented by the following general formula (I): -Provide all derivatives.
  • the present invention also contains this substituted 1- (1-chlorocyclopropyl) -2- (1H-1,2,4-triazol-1-yl) -2-propen-1-ol derivative as an active ingredient.
  • An agricultural and horticultural agent or an industrial material protective agent is provided.
  • the present invention includes a step of reducing a carbonyl compound represented by the following general formula (II), wherein the substituted 1- (1-chlorocyclopropyl) -2- (1H-1,2, Also provided is a process for the preparation of 4-triazol-1-yl) -2-propen-1-ol derivatives.
  • X represents a halogen atom
  • n represents an integer of 0 to 5.
  • the present invention exhibits an excellent agricultural and horticultural disease control effect, plant growth control effect, industrial material protective effect, and imparts desired properties to agricultural and horticultural chemicals and industrial material protective agents. Novel compounds capable of
  • examples of the halogen atom represented by “X” include a chlorine atom, a fluorine atom, a bromine atom and an iodine atom, more preferably a fluorine atom, a chlorine atom and a bromine atom, still more preferably. It is a chlorine atom.
  • N represents an integer of 0 to 5, preferably 1 to 2, and more preferably 1. When “n” is 1, it is particularly preferred that the halogen atom is in the 4-position. When “n” is an integer of 2 or more, “X” may be the same or different.
  • Compound (I) has the following geometric isomers (E type and Z type).
  • (I-E) represents an E-type compound in which a triazolyl group and a phenyl group are bonded to the trans position
  • (I-Z) represents a Z-type compound bonded to the cis position.
  • Compound (I) can be used in a state where only one of these geometric isomers is separated or in a state where both are mixed, but it is preferable to use a separated E-type compound.
  • Compound (I) Since Compound (I) has a 1,2,4-triazolyl group, it forms an acid addition salt of an inorganic acid or an organic acid or a metal complex. When compound (I) is blended in the agricultural and horticultural chemicals and industrial material protecting agents described later, it can also be blended as part of an acid addition salt or metal complex.
  • compound (II) a carbonyl compound represented by the following general formula (II) (hereinafter abbreviated as “compound (II)”) is reduced with a reducing agent to produce compound (I).
  • Reaction formula (1) showing the reduction from compound (II) to compound (I) is shown below.
  • the reaction is usually performed by mixing compound (II) and a reducing agent in a solvent.
  • the solvent is not particularly limited as long as it does not participate in the reaction shown in the reaction formula (1), but ethers such as diethyl ether, tetrahydrofuran and dioxane, alcohols such as methanol, ethanol and isopropanol, benzene, toluene, Aromatic hydrocarbons such as xylene, aliphatic hydrocarbons such as petroleum ether, hexane, methylcyclohexane, amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidinone, etc. Can be used.
  • the solvent water, acetonitrile, ethyl acetate, acetic anhydride, acetic acid, pyridine, dimethyl sulfoxide, or the like can be used. Two or more of these solvents may be used in combination. Furthermore, the solvent composition which consists of a some solvent which does not form a uniform layer mutually can also be used. In this case, it may be better to add a phase transfer catalyst such as a conventional quaternary ammonium salt or crown ether to the reaction system.
  • a phase transfer catalyst such as a conventional quaternary ammonium salt or crown ether
  • the reducing agent is not particularly limited, and preferred examples include metal hydride compounds such as sodium borohydride and lithium aluminum hydride, and aluminum alkoxides such as aluminum isopropoxide.
  • suitable solvents include ethers such as diethyl ether, tetrahydrofuran and dioxane, and alcohols such as methanol, ethanol and isopropanol.
  • the amount of sodium borohydride to be used with respect to compound (II) is usually 0.1 to 5 times mol, preferably 0.2 to 2 times mol.
  • the reaction temperature is usually -80 to 100 ° C, preferably -20 to 50 ° C.
  • the reaction time is usually 0.1 hour to several days, preferably 0.1 hour to 1 day.
  • lithium aluminum hydride when lithium aluminum hydride is used as the reducing agent, examples of suitable solvents include ethers such as diethyl ether, tetrahydrofuran, and dioxane.
  • suitable solvents include ethers such as diethyl ether, tetrahydrofuran, and dioxane.
  • the amount of lithium aluminum hydride used relative to compound (II) is usually 0.05 to 5 times mol, preferably 0.1 to 3 times mol.
  • the reaction temperature is usually -100 to 100 ° C, preferably -80 to 50 ° C.
  • the reaction time is usually 0.05 hours to several days, preferably 0.1 hour to 1 day.
  • suitable solvents include alcohols such as isopropanol and aromatic hydrocarbons such as benzene, toluene and xylene.
  • the amount of aluminum isopropoxide used relative to compound (II) is usually 0.2 to 10 times mol, preferably 0.5 to 5 times mol.
  • the reaction temperature is usually 0 to reflux point, preferably room temperature to reflux point.
  • the reaction time is usually 0.1 hour to several days, preferably 0.5 hour to 2 days. In this case, the obtained aluminum compound is decomposed with dilute sulfuric acid or an aqueous sodium hydroxide solution, and then extracted with an organic solvent hardly soluble in water.
  • the solvent used in the reaction can be alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene, toluene and xylene, and ethers such as diethyl ether, tetrahydrofuran and dioxane.
  • acetic acid, acetic anhydride, etc. can also be used for a solvent.
  • the solvent used is not limited to these.
  • Bases that can be used as catalysts include alkali metals such as sodium hydroxide, potassium hydroxide, calcium hydroxide, or alkaline earth metal hydroxides, sodium methoxide, sodium ethoxide, potassium t-butoxide, and other alkali metal.
  • Alkali metal carbonates such as alkoxide, sodium carbonate and potassium carbonate, alkaline earth metal carbonates such as calcium carbonate and barium carbonate, acetates such as sodium acetate and potassium acetate, triethylamine, dipropylamine, pyrrolidine, piperidine, And organic amines such as morpholine.
  • the amount of compound (IV) used relative to compound (III) is usually 0.5 to 10 times mol, and more preferably 0.5 to 2 times mol.
  • the amount of the base used relative to compound (III) is usually 0.01 to 10 times mol, more preferably 0.1 to 5 times mol.
  • the reaction temperature is usually from 0 to the reflux point, preferably from room temperature to the reflux point.
  • the reaction time is usually 0.1 hour to several days, preferably 0.5 hour to 2 days.
  • Compound (III) can be produced by a known method, and compound (IV) can be a commercially available product or a product produced by a known method.
  • Agricultural and horticultural chemicals and industrial material protective agents contain compound (I) as an active ingredient.
  • Agricultural and horticultural chemicals Compound (I) exhibits a controlling effect against a wide range of plant diseases. Examples of applicable diseases include the following.
  • Soybean rust (Phakopsora pachyrhizi, Phakopsora meibomiae), rice blast (Pyricularia grisea), rice sesame leaf blight (Cochliobolus miyabeanus), rice white leaf blight (Xanthomonas oryzae), rice rot (Rhizoctonia sol) Nuclear disease (Helminthosporium sigmoideun), rice seedling disease (Gibberella fujikuroi), rice seedling blight (Pythium aphanidermatum), apple powdery mildew (Podosphaera leucotricha), apple black rot (Venturia inaequalis), apple peach linear Apple spotted leaf blight (Alternaria alternata), apple rot blight (Valsa mali), pear black blight (Alternaria kikuchiana), pear powdery mildew (Phyllactinia pyri), pear red blight
  • Examples of applied plants include wild plants, plant cultivars, plants obtained by conventional biological breeding such as crossbreeding or protoplast fusion, plant cultivars, genetically modified plants and plant cultivars obtained by genetic manipulation. Can be mentioned.
  • Examples of genetically modified plants and plant cultivars include herbicide-tolerant crops, pest-tolerant crops incorporating insecticidal protein production genes, disease-resistant crops incorporating resistance-inducing substance production genes for diseases, improved crops, improved yields
  • Examples include crops, crops with improved shelf life, and crops with improved yield.
  • Specific examples of genetically modified plant cultivars include those containing registered trademarks such as ROUNDUP READY, LIBERTY LINK, CLEARFIELD, YIELDGARD, HERCULEX, BOLLGARD and the like.
  • Plant Growth Action Compound (I) also has the effect of regulating the growth and increasing the yield of a wide variety of crops and horticultural plants and the quality of the product. Examples of such crops include:
  • compound (I) shows the outstanding effect which protects material from the extensive harmful microorganisms which invade industrial material. Examples of such microorganisms include the following.
  • Tricothecium sp. Rubber and plastic degrading microorganisms such as Aspergillus sp., Penicillium (Penicillium sp.), Rhizopus sp., Trichoderma sp., Ketotomium sp., Milotesium (Myrothecium sp.), Streptomyces sp., Pseudomonas sp. , Bacillus (sp.), Micrococcus (sp.), Serratia (sp.), Margarinomyces (sp.), Monascus sp., Monascus sp., Aspergillus sp.
  • Penicillium Psp. Cladosporium sp., Aureobasidium sp., Gliocladium sp., Botryodiplodia sp., Macrospo Limon (Macrosporium sp.), Monilia (Monilia sp.), Forma (Phoma sp.), Pullularia ((Pullularia sp.), Sporotrichum sp., Trichoderma sp., Bacillus (sp.) , Proteus sp., Pseudomonas sp., Serratia sp.
  • Compound (I) as an active ingredient of agricultural and horticultural medicine, it may be left as it is without adding any other components, but usually a solid carrier, liquid carrier, surfactant, other formulation aids It is mixed with an agent and formulated into various forms such as powders, wettable powders, granules, and emulsions.
  • compositions are formulated so as to contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight, more preferably 2 to 80% by weight of the compound (I) as an active ingredient.
  • Examples of carriers, diluents, and surfactants used as formulation adjuvants include talc, kaolin, bennite, diatomaceous earth, white carbon, and clay as solid carriers.
  • Liquid diluents include water, xylene, toluene, chlorobenzene, cyclohexane, cyclohexanone, dimethyl sulfoxide, dimethylformamide, alcohol and the like.
  • Surfactants should be used properly depending on their effects, such as polyoxyethylene alkylaryl ether and polyoxyethylene sorbitan monolaurate as emulsifiers, wetting agents such as lignin sulfonate and dibutylnaphthalene sulfonate as dispersants. Examples thereof include alkyl sulfonates and alkylphenyl sulfonates.
  • compositions are used as they are, while others are diluted to a predetermined concentration with a diluent such as water.
  • concentration of compound (I) when used after dilution is preferably in the range of 0.001 to 1.0%.
  • the amount of compound (I) used is 20 to 5000 g, more preferably 50 to 2000 g, per ha of agricultural or horticultural land such as fields, fields, orchards, and greenhouses. Since these use concentrations and amounts vary depending on the dosage form, use time, use method, use place, target crop, etc., they can be increased or decreased without sticking to the above range.
  • the compound (I) can be used in combination with other active ingredients such as fungicides, insecticides, acaricides and herbicides as exemplified below to enhance performance as agricultural and horticultural agents.
  • ⁇ Antimicrobial substances Acibenzolar S methyl, 2-phenylphenol (OPP), azaconazole, azoxystrobin, amisulbrom, bixaphene, benalaxyl, benomyl, bench avaricarb-isopropyl, bicarbonate, biphenyl, viteltanol, blasticidin-S, borax, bordeaux, boscalid, Bromuconazole, bronopol, bupirimate, secbutyramine, calcium polysulfide, captafor, captan, carbendazim, carboxin, carpropamide, quinomethionate, chloronebu, chloropicrin, chlorothalonil, clozolinate, cyazofamide, cyflufenamide, simoxanil, cyproconil, cyprodiazole Dazomet, debacarb, diclofuranide, diclocimet, dichrome , Dichlorane, dieth
  • ⁇ Insecticide / acaricide / nematicide> Abamectin, Acephate, Acrinathrin, Alanicarb, Aldicarb, Alletrin, Amitraz, Avermectin, Azadirachtin, Azamethifos, Azinphos-ethyl, Azinphos-methyl, Azocycline, Bacillus filmus, Bacillus subtilis, Bacillus thuringibulbbenthulbenbencarb , Benzoxymate, Bifenazite, Bifenthrin, Bioallethrin, Bioresmethrin, Bistriflurone, Buprofezin, Butocaboxin, ButoxyCarboxin, Kazusafos, Carbaryl, Carbofuran, Carbosulfan, Cartap, CGA 50439, Chlordein, Chloretifos, Chlorphenapal Chlorfenvin foss, chlor
  • the compound (I) as an active ingredient of an industrial material protective agent, it may be used alone without adding other components, but it is generally dissolved or dispersed in a suitable liquid carrier, or a solid carrier And if necessary, further add emulsifier, dispersant, spreader, penetrant, wetting agent, stabilizer, etc., wettable powder, powder, granule, tablet, paste, suspension, It can be used as a dosage form such as a spray material. Moreover, you may mix
  • any liquid may be used as long as it does not react with the active ingredient.
  • water alcohols (for example, methyl alcohol, ethyl alcohol, ethylene glycol, cellosolve, etc.), ketones (for example, acetone, methyl ethyl ketone, etc.) ), Ethers (eg dimethyl ether, diethyl ether, dioxane, tetrahydrofuran, etc.), aromatic hydrocarbons (eg benzene, toluene, xylene, methylnaphthalene, etc.), aliphatic hydrocarbons (eg gasoline, kerosene, kerosene, machinery Oil, fuel oil, etc.), acid amides (eg, dimethylformamide, N-methylpyrrolidone, etc.), halogenated hydrocarbons (eg, chloroform, carbon tetrachloride, etc.), esters (eg, ethyl acetate, fatty acids, etc., etc
  • fine powders or granular materials such as kaolin clay, bentonite, acid clay, pyrophyllite, talc, diatomite, calcite, urea, ammonium sulfate can be used.
  • surfactants such as soaps, alkylsulfonic acids, alkylarylsulfonic acids, dialkylsulfosuccinic acids, quaternary ammonium salts, oxyalkylamines, fatty acid esters, polyalkylene oxides, anhydrosorbitols, etc. Can be used.
  • compound (I) When compound (I) is contained in the preparation as an active ingredient, the content varies depending on the dosage form and intended purpose, but it is generally appropriate to add it at a concentration of 0.1 to 99.9% by weight. is there. In actual use, it is preferable to adjust the treatment concentration by adding a solvent, a diluent, an extender or the like as appropriate so that the treatment concentration is usually 0.005 to 5% by weight, preferably 0.01 to 1% by weight. .
  • Compound (I) can also be formulated in combination with antibacterial substances, insecticides, deterioration inhibitors and the like, similar to the above-mentioned agricultural and horticultural agents. Thereby, the performance as an industrial material protective agent can be improved.
  • reaction solution was filtered, the filtrate was concentrated under reduced pressure, the residue was dissolved in chloroform, the organic layer was washed with water, saturated aqueous sodium hydrogen carbonate, and saturated brine, and then dried over anhydrous sodium sulfate.
  • Granules The ingredients shown in Table 5 below are uniformly mixed, water is added and kneaded, and processed and dried into granules with an extrusion granulator to obtain granules.
  • ⁇ Test Example 1> Cucumber gray mold control effect test To the cucumber in the cotyledon stage (variety: SHARP1) cultivated using a square plastic pot (6 cm ⁇ 6 cm), the wettable powder prepared in Formulation Example 1 was added to water at a predetermined concentration ( The suspension was diluted to 50 mg / l) and sprayed at a rate of 1,000 L / ha. After the sprayed leaves were air-dried, a paper disc (diameter 8 mm) impregnated with a spore solution of gray mold was placed and kept at 20 ° C. under high humidity. On the 4th day after inoculation, the morbidity of cucumber gray mold was investigated, and the control value was calculated by the following formula. In the formula, “morbidity” was in accordance with “Table 7”.
  • Control value (%) (1-average morbidity in sprayed area ⁇ ⁇ average morbidity in non-sprayed area) x 100
  • Table 8 shows the results of the control effect test.
  • a remarkably high control effect was recognized as compared with the comparative compound (1).
  • Table 9 shows the results of the control effect test.
  • a remarkably high control effect was recognized as compared with the comparative compound (2).
  • Control value (%) (1-average morbidity in sprayed area ⁇ ⁇ average morbidity in non-sprayed area) x 100
  • Table 11 shows the results of the control effect test.
  • a remarkably high control effect was recognized as compared with the comparative compound (1).
  • Table 12 shows the results of the control effect test.
  • a remarkably high control effect was recognized as compared with the comparative compound (2).
  • Control value (%) (1-average morbidity in sprayed area ⁇ ⁇ average morbidity in non-sprayed area) x 100
  • test bacteria cultured on a normal plate medium were punched out with a cork borer having a diameter of 4 mm and inoculated on the plate medium containing the above-mentioned compounds. After inoculation, the cells were cultured for 1 to 3 days at the optimum temperature for growth of each fungus (see “Fellow Institute of Fermentation“ LIST OF CULTURES 1996 microorganisms 10th edition ”), and the growth of the fungi was measured by the fungus diameter. The growth degree of the bacteria obtained on the plate medium containing each compound was compared with the growth degree of the bacteria on the normal plate medium, and the hyphal elongation inhibition rate was determined by the following formula.
  • R 100 (dc ⁇ dt) / dc (In the formula, “R” represents the mycelial elongation inhibition rate (%), “dc” represents the diameter of the fungus on a normal plate medium, and “dt” represents the diameter of the fungus on a plate medium containing each compound. )
  • Table 16 shows the results of five-stage evaluation of the obtained hyphal elongation inhibition rate according to the following criteria. 5: Mycelium elongation inhibition rate of 90% or more 4: Mycelium elongation inhibition rate of less than 90 to 70% or more 3: Mycelium elongation inhibition rate of less than 70 to 40% or more 2: Mycelium elongation inhibition rate of 40 Less than 20% or more 1: Hypha elongation suppression rate is less than 20%
  • Pn wheat blight fungus (Phaeosphaeria nodorum)
  • Ph Wheat eye spot disease fungus (Pseudocercoporella herpotrichoides)
  • Fg Fusarium graminearum
  • Un Barley Bare Smut Fungus (Ustilago nuda)
  • Po Rice blast fungus (Pyricularia oryzae)
  • Gf Rice idiotic fungus (Giberella fujikuroi)
  • Am Alternaria alternata
  • Ss Sclerotinia sclerotiorum
  • Bc Botrysis cinerea
  • Fc Fusarium oxysporum
  • R.sec Rhynchosporium secalis
  • R 100 (hc ⁇ ht) / hc (In the formula, “R” represents the plant height inhibition rate (%), “hc” represents the average plant height of the untreated group, and “ht” represents the average plant height of the group treated with each compound.)
  • the plant height suppression rate obtained was evaluated in five stages.
  • the compounds (I-1), (I-3), (I-5), and (I-18) were evaluated with a rating of 4 or more. High growth control effect was observed.
  • the substituted 1- (1-chlorocyclopropyl) -2- (1H-1,2,4-triazol-1-yl) -2-propen-1-ol derivative according to the present invention is a fungicide for agriculture and horticulture. Not only useful as an active ingredient, but also from plant growth regulators that increase the yield and improve the quality of various crops and horticultural plants, and from a wide range of harmful microorganisms that invade industrial materials It is also useful as an industrial material protective agent showing the effect of protecting the material.

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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)
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  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne un nouveau composé qui présente d'excellents effets de lutte contre les maladies en agriculture/horticulture, de régulation de la croissance des plantes et de protection des équipements industriels, et qui peut développer des propriétés plus satisfaisantes dans un produit chimique employé en agriculture/horticulture et dans un agent de protection des équipements industriels. Il est proposé un dérivé de 1-(1-chlorocyclopropyle)-2-(1H-1,2,4-triazole-1-yle)-2-propène-1-ole substitué représenté par la formule générale (I). Dans la formule générale (I), X représente un atome d'halogène ; et n représente un nombre entier de 0 à 5.
PCT/JP2009/071225 2008-12-22 2009-12-21 Dérivé de 1-(1-chlorocyclopropyle)-2-(1h-1,2,4-triazole-1-yle)-2-propène-1-ole substitué, son procédé de production, et produit chimique employé en agriculture/horticulture et agent de protection des équipements industriels contenant celui-ci Ceased WO2010074021A1 (fr)

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JP2008325019 2008-12-22
JP2008-325019 2008-12-22

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013077265A1 (fr) * 2011-11-25 2013-05-30 株式会社クレハ Dérivé d'azole et son utilisation
CN103664808A (zh) * 2013-11-26 2014-03-26 中国农业大学 一种含氯代环丙烷的芳基三氮唑化合物及其制备方法与应用
US9440933B2 (en) 2011-06-07 2016-09-13 Kureha Corporation Azole derivative, method for producing same, intermediate compound, and agricultural or horticultural chemical agent and industrial material protecting agent
US9750254B2 (en) 2013-12-05 2017-09-05 Kureha Corporation Agricultural or horticultural chemical, method of controlling plant diseases, and product for controlling plant diseases
US9814236B2 (en) 2013-12-05 2017-11-14 Kureha Corporation Agricultural or horticultural chemical, method of controlling plant diseases, and product for controlling plant diseases

Citations (2)

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JPS5753471A (en) * 1980-07-25 1982-03-30 Bayer Ag Triazolylpropenol derivative, manufacture and use

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US9440933B2 (en) 2011-06-07 2016-09-13 Kureha Corporation Azole derivative, method for producing same, intermediate compound, and agricultural or horticultural chemical agent and industrial material protecting agent
WO2013077265A1 (fr) * 2011-11-25 2013-05-30 株式会社クレハ Dérivé d'azole et son utilisation
CN103946216A (zh) * 2011-11-25 2014-07-23 株式会社吴羽 唑衍生物及其应用
JPWO2013077265A1 (ja) * 2011-11-25 2015-04-27 株式会社クレハ アゾール誘導体、およびその利用
US9278941B2 (en) 2011-11-25 2016-03-08 Kureha Corporation Azole derivative and uses thereof
CN103946216B (zh) * 2011-11-25 2016-07-06 株式会社吴羽 唑衍生物及其应用
CN103664808A (zh) * 2013-11-26 2014-03-26 中国农业大学 一种含氯代环丙烷的芳基三氮唑化合物及其制备方法与应用
US9750254B2 (en) 2013-12-05 2017-09-05 Kureha Corporation Agricultural or horticultural chemical, method of controlling plant diseases, and product for controlling plant diseases
US9814236B2 (en) 2013-12-05 2017-11-14 Kureha Corporation Agricultural or horticultural chemical, method of controlling plant diseases, and product for controlling plant diseases

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