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WO2006118155A1 - Derive de biphenyle ou son sel, et bactericide pour un usage en agriculture et en horticulture le contenant en tant que principe actif - Google Patents

Derive de biphenyle ou son sel, et bactericide pour un usage en agriculture et en horticulture le contenant en tant que principe actif Download PDF

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Publication number
WO2006118155A1
WO2006118155A1 PCT/JP2006/308764 JP2006308764W WO2006118155A1 WO 2006118155 A1 WO2006118155 A1 WO 2006118155A1 JP 2006308764 W JP2006308764 W JP 2006308764W WO 2006118155 A1 WO2006118155 A1 WO 2006118155A1
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group
substituted
alkyl
formula
halogen
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PCT/JP2006/308764
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English (en)
Japanese (ja)
Inventor
Shigeru Mitani
Hitoshi Nakayama
Koji Sugimoto
Munekazu Ogawa
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Ishihara Sangyo Kaisha, Ltd.
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Publication of WO2006118155A1 publication Critical patent/WO2006118155A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/61—Halogen atoms or nitro radicals
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • C07C233/15—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/66—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/90—Carboxylic acid amides having nitrogen atoms of carboxamide groups further acylated
    • C07C233/92—Carboxylic acid amides having nitrogen atoms of carboxamide groups further acylated with at least one carbon atom of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
    • C07C239/08—Hydroxylamino compounds or their ethers or esters
    • C07C239/14—Hydroxylamino compounds or their ethers or esters having nitrogen atoms of hydroxylamino groups further bound to carbon atoms of hydrocarbon radicals substituted by doubly-bound oxygen atoms

Definitions

  • the present invention relates to an agricultural and horticultural fungicide containing a novel biphenyl derivative or a salt thereof as an active ingredient.
  • Known agricultural and horticultural fungicides having a biphenyl structure include those described in European Patent Publication No. 101 0690, which may be branched between a biphenyl group and a substituted amino group. Since it has C alkylene, its chemical structure is different from the compound of the present invention.
  • Patent Document 1 European Published Patent Publication No. 1010690
  • Patent Document 2 International Publication WO05Z44007
  • halogen atom contained in the formula (I) fluorine, chlorine, bromine or iodine is used.
  • fluorine, chlorine or bromine is used.
  • alkyl moiety contained in the formula (I) examples include C alkyl such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tbutyl.
  • alkoxy moiety contained in the formula (I) examples include C alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, t-butoxy and the like.
  • alkell moiety contained in the formula (I) examples include C alkell such as bulle, valyl, isopropyl and 3-methyl-2-butyr.
  • alkyl moiety contained in the formula (I) examples include C alkyl such as ethynyl, 1-propyl, 2-propyl (propargyl) and the like.
  • Examples of the cycloalkyl contained in the formula (I) include c cycloalkyl such as cyclopropyl, cyclopentyl, cyclohexyl and the like.
  • the aryl part contained in the formula (I) is, for example, a C aryl such as a file or naphthyl.
  • examples of the heterocyclic moiety contained in the formula (I) include pyridyl, chael, fuller, thiazolyl and the like.
  • examples of the substituent of the substitutable filer and the substitutable heterocycle included in the formula (I) include halogen, alkyl, haloalkyl, alkoxy, haloalkoxy and the like.
  • the biphenyl derivative represented by the formula (I) or a salt thereof exhibits an excellent effect as an active ingredient of an agricultural and horticultural fungicide.
  • the compound of the formula (I) or a salt thereof can be produced by various known synthesis methods using characteristics based on the basic skeleton or the type of substituent.
  • a substituent such as an amino group, a hydroxyl group, or a carboxyl group
  • the substituent is protected with an appropriate protecting group at the stage of the raw material or intermediate, or the substituent can be easily added.
  • Substitution with a convertible substituent group may enable efficient production.
  • Examples of the protecting group described above include the protecting groups described in Examples X ⁇ i, .W. Greene, P.tj.M.Wuts, Protective Groups in urganic Syntnesis (3rd Edition, 1999).
  • a desired compound can be obtained by carrying out a reaction using the protecting group and then removing the protecting group or converting to a desired group as necessary. it can.
  • the method using a protecting group can be carried out by applying methods well known by those skilled in the art, such as ordinary hydrolysis, esterification, amidation, dehydration, diazotization, oxidation and the like.
  • the compound of formula (I) is obtained by coupling a compound of formula (II) and a compound of formula (III) in the presence of a suitable transition metal catalyst, or by formula (VII) And a compound of formula (VI) can be produced by coupling in the presence of a suitable transition metal catalyst.
  • the reaction can be carried out by a known method (for example, 5th edition, Experimental Chemistry Course 18—Synthesis of Organic Compounds VI, pp.327-352 “Section 3.2 Cross Coupling Reaction” (Maruzen), Comprehensive Organic Synthesis, Volume 3, 481,1991 or Synthetic Communications, Volumell, 513, 1981 etc.).
  • the leaving group represented by L in formula (II) or formula (VII) includes halogen, trifluoromethanesulfo-loxy isotonic as a metal represented by M in formula (III) or formula (VI) Examples thereof include magnesium halide, zinc halide, alkyl tin, alkyl silicon, alkoxy silicon, silicon halide, alkyl aluminum, and aluminum halide.
  • the transition metal catalyst used in the reaction means a transition metal compound or a complex of a transition metal compound and an arbitrary ligand.
  • palladium-carbon Pd / C
  • tetra Kis triphenylphosphine
  • bis dibenzylideneacetone
  • tris dipalladium (0)
  • palladium acetate II) triphenylphosphine
  • palladium (II) acetate Tricyclohexylphosphine
  • dichloropalladium (II) -ethylenediamine- ⁇ , ⁇ , ⁇ ', ⁇ '-tetraacetic acid palladium (II) bis (dicyclohexylamine), dichloropalladium ( ⁇ ) - ⁇ , ⁇ '-Bis (dicyclohexylphosphino) pheucene, -Keckel carbon (Ni / C), tetrakis (triphenylphosphine) nickel (0), bis (1,5-cycloo
  • iron and copper catalysts can be used when the power lacks generality and M is magnesium halide.
  • M is magnesium halide.
  • a previously isolated one may be used, or a transition metal compound and a ligand may be mixed in an arbitrary reaction solvent and used without isolation.
  • the transition metal catalyst is used in a proportion of 0.001 to 0.2 equivalents, preferably 0.01 equivalents to 0.1 equivalents, relative to the compound of formula (IV).
  • the reaction is carried out, for example, with ketones such as acetone, methyl ethyl ketone, and cyclohexanone; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, 1,4 dioxane, dimethoxetane, and diethylene glycol dimethyl ether; ethyl acetate, acetic acid Esters such as methyl; Ananolones such as methanol, ethanol, n-propanol, and isopropanol; Aromatic hydrocarbons such as benzene, black benzene, nitrobenzene, and tolylene; -Tolyls such as acetonitrile; ⁇ , ⁇ -dimethyl Formamide; ⁇ , ⁇ -dimethylacetamide; ⁇ -methyl-2-pyrrolidone; dimethyl sulfoxide; polyethylene glycols; water or other solvent that does not inhibit the progress
  • the compound of formula (II) or the compound of formula (VII) and the compound of formula (III) or the compound of formula (VI) can be used in an equivalent amount or in excess.
  • the reaction is generally performed in the presence of an appropriate base.
  • bases include alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate; alkaline earth metal carbonates such as calcium carbonate; sodium hydroxide , Alkaline metal hydroxides such as potassium hydroxide, alkaline earths such as calcium hydroxide Metal hydroxides; Phosphate salts such as potassium phosphate; Inorganic salts such as cesium fluoride and potassium fluoride; Amines such as triethylamine; Pyridines such as pyridine and 4- ( ⁇ , ⁇ -dimethylamino) pyridine Can be mentioned.
  • the base is usually used in a proportion of 1.0 to 20 equivalents, preferably 1.0 to 3.0 equivalents, relative to the compound of formula (II) or the compound of formula (VII).
  • Additives include alkenes such as 1,3-butadiene and aryloxybenzene; inorganic salts such as lithium chloride; quaternary ammonium salts such as tetrabutyl ammonium bromide; 1,4-diazabicyclo And organic bases such as [2,2,2] octane.
  • the additive is used in a proportion of 0.001 to 2 equivalents, preferably 0.01 equivalents to 1 equivalent, relative to the compound of formula (II).
  • the reaction temperature is 70 ° C to 300 ° C, preferably 0 ° C to the boiling point of the solvent used.
  • the reaction time is not constant depending on the reaction temperature, reaction amount, reaction pressure, etc., but generally it can be selected from the range of 1 to 72 hours.
  • a compound of formula (I 1) in which A in formula (I) is a carbonyl group can also be prepared by the following method
  • the compound of the formula (I 1) can be produced by an amidy reaction between the compound of the formula (V) and the compound represented by HNR 2 .
  • the protecting group for the carboxyl group represented by Q in the compound of the formula (V) is preferably an alkyl group, although it may be substituted with a phenyl or pyridyl group.
  • the compound of formula (V) is represented by HNR 2 in the presence of a condensing agent as necessary.
  • a condensing agent examples include dicyclohexyl carbodiimide, diisopropyl carbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide and the like.
  • solvents examples include aromatic hydrocarbons such as benzene, toluene, and xylene; ethers such as jetyl ether, tetrahydrofuran, 1,4-dioxane, and dimethoxyethane; dichloromethane, 1,2-dichloroethane, and chloroform.
  • Halogenated hydrocarbons such as: alcohols such as methanol and ethanol; ⁇ , ⁇ -dimethylformamide, ⁇ -methyl-2-pyrrolidone, pyridine and the like.
  • two or more kinds of these solvents can be used as a mixed solvent in some cases.
  • the reaction temperature is 70 ° C to 300 ° C, preferably 0 ° C to the boiling point of the solvent used.
  • the reaction time varies depending on the reaction temperature, reaction volume, reaction pressure, etc. Generally, it is only necessary to select a force within the range of 1 to 72 hours.
  • the compound of the formula (I 1) can also be produced by a method using a reactive derivative of the compound of the formula (V) in place of the compound of the formula (V) in the amidation reaction.
  • a reactive derivative of the compound of the formula (V) an acid halide, an acid anhydride, an active ester and the like can be used.
  • the reaction can be performed, for example, according to the method described in “Chemical Experiment Course (4th edition)” edited by The Chemical Society of Japan, 22 (1992) (Maruzen). An example of such a reaction is shown in the following flow.
  • the compound of formula (V) which is the starting material of production method 2 can be produced by the following method.
  • the protective group Q can be applied with the protective group for a carboxyl group described in the above-mentioned ⁇ Protective Groups in Organic Synthesis (3rd Edition, 1999) ''. Or by hydrolysis.
  • a compound in which Q is a hydrogen atom can be prepared by hydrolyzing a compound in which Q is a carboxyl protecting group.
  • the compound of the formula (V) is obtained by coupling the compound of the formula (IV) and the compound of the formula (III) in the presence of a transition metal catalyst, or the compound of the formula (VII) and the compound of the formula (VIII). It can be produced by coupling a compound with a transition metal catalyst.
  • a transition metal catalyst a transition metal compound used in Production Method 1 or a complex of a transition metal compound and an arbitrary ligand can be used.
  • the transition metal catalyst is used in a proportion of 0.001 to 0.2 equivalent, desirably 0.01 equivalent to 0.1 equivalent, relative to the compound of formula (IV) or formula (VII).
  • the reaction may be carried out, for example, with ketones such as acetone, methyl ethyl ketone, and cyclohexanone; ethers such as jetyl ether, diisopropyl ether, tetrahydrofuran, 1,4 dioxane, dimethoxyethane, and diethylene glycol dimethyl ether; Esters such as ethyl and methyl acetate; Alcohols such as methanol, ethanol, n-propanol, and isopropanol; Aromatic hydrocarbons such as benzene, black benzene, nitrobenzene, and toluene; Acetonitrile, etc.
  • ketones such as acetone, methyl ethyl ketone, and cyclohexanone
  • ethers such as jetyl ether, diisopropyl ether, tetrahydrofuran, 1,4 dioxane, dimethoxyethane, and di
  • the compound of formula (IV) or formula (VII) and the compound of formula (III) or formula (VIII) can be used in an equivalent amount or in excess.
  • the reaction in the presence of bases may be advantageous for the smooth progress of the reaction.
  • bases include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate; alkaline earth metal carbonates such as calcium carbonate; , Alkali metal hydroxides such as potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide, inorganic salts such as cesium fluoride and potassium fluoride, and amines such as triethylamine And pyridines such as pyridine and 4- ( ⁇ , ⁇ -dimethylamino) pyridine.
  • the base is usually used in a proportion of 1.0 to 20 equivalents, preferably 1.0 to 3.0 equivalents, relative to the compound of formula (IV) or formula (VII).
  • the reaction temperature is 70 ° C to 300 ° C, preferably 0 ° C to the boiling point of the solvent used.
  • the reaction time is not constant depending on the reaction temperature, reaction volume, reaction pressure, etc. Generally, you can select a force ranging from 1 hour to 72 hours.
  • the compound of formula (V-1) when Q is a hydrogen atom can also be produced by the following method.
  • the compound of the formula (V-1) can be produced by acidifying the compound of the formula (XI) by an ordinary method using an oxidizing agent such as manganese diacid and potassium permanganate.
  • the compound of formula (XI) is obtained by coupling a compound of formula (IX) and a compound of formula (III) in the presence of a transition metal catalyst, or a compound of formula (VII) and formula (X).
  • This compound can be produced by the use of force coupling in the presence of a transition metal catalyst. Both coupling reactions can be carried out in the same manner as in Production Method 1 described above.
  • a compound of formula (XV) can be produced by halogenating a compound of formula (V-1). For this reaction, the usual acid halogenated reaction can be applied.
  • This reaction is preferably carried out at a reaction temperature of O to 200 ° C. in the presence or absence of an inert solvent such as dichloroethane.
  • an inert solvent such as dichloroethane.
  • the halogenating agent used in this reaction include a fluorinating agent, a chlorinating agent, and a brominating agent, but a chlorinating agent such as chlorothionyl, oxylin chloride, and chlorooxalyl is used. Hope to do.
  • the compound of formula (I2) can be produced by subjecting the compound of formula (XIV) to a usual reduction reaction such as catalytic reduction or iron reduction.
  • the compound of formula (XIV) is obtained by coupling a compound of formula (XII) and a compound of formula (III) in the presence of a transition metal catalyst, or a compound of formula (VII) and It can be produced by coupling a compound with a transition metal catalyst.
  • the reaction for producing the compound of the formula (XIV) can be carried out according to the reaction described in production method 1. Further, the compound of the formula (XIV) can be subjected to the production reaction of the compound of the formula (I2) with or without isolation and purification.
  • X ′ and ⁇ are each independently a halogen atom; a hydroxyl group; a formyl group; a substituent that is substituted with a norogen, an alkoxy group, or an alkylthio; an alkyl group, a tro group; Group substituted by halogen or alkoxy, alkoxy group substituted by halogen or haloalkyl, aryloxy group; substituted by halogen or haloalkyl, heterocyclic oxy group; substituted by halogen or haloalkyl A heterocyclic group; an alkyl group, an alkyl carbo group; an alkyl carbo group; an alkyl carbo group; an alkylthio group; an alkyl sulpho group; A group; an alkyl sulfier group or an imino group optionally substituted by alkyl or alkoxy ⁇ , is a halogen atom; a formyl group; may be substituted with
  • a ′ is a carbo group; a thio group; an alkylene group or a single bond, R 1 and R 2 are each independently a hydrogen atom; halogen, cycloalkyl, substituted phenyl, substituted heterocycle An alkyl group which may be substituted with alkylthio, alkoxy or cyan; a alkenyl group which may be substituted with norogen, cycloalkyl, fur or cyan; a norogen, cycloalkyl, phenol or cyan May be substituted !, an alkyl group; a cycloalkyl group that may be substituted with halogen or alkyl; Well, alkoxy group; may be substituted with halogen, alkyl or haloalkyl!
  • Aryl group may be substituted with halogen, alkyl or haloalkyl, heterocyclic group; may be substituted with halogen, alkylcarbo -Alkyl group; alkenyl group; imino group; may be substituted with alkyl !, amino group; may be substituted with alkyl !, aminocarbol group; alkylcarbo-lamino group; formyl group or cyano And m and ⁇ are each independently 0, 1, 2, 3 or 4].
  • the biphenyl derivative of the formula (I) is one of the biphenyl derivatives of the formula ( ⁇ ), especially for preventing plant diseases.
  • the present inventors have specifically found a substituent pattern of a compound having an excellent removal effect.
  • the compound of the formula (I ′) is a method according to the compound of the formula (I), that is, in the production methods 1 to 3 described above.
  • the biphenyl derivative represented by the formula (I) or a salt thereof include an agricultural and horticultural fungicide and It is useful as an active ingredient in pest control agents such as Z or antifungal agents, but is particularly useful as an active ingredient in agricultural and horticultural fungicides.
  • Agricultural and horticultural fungicides include, for example, rice blast, sesame leaf blight, coat blight; wheat powdery mildew, red mold, rust, snow rot, naked smut, eye coat disease, leaves Blight, dry blight; citrus sunspot disease, common scab; apple moyulia disease, powdery mildew, spotted leaf disease, black star disease; pear black star disease, black spot disease; peach ash star disease, black star disease, Phomopsis rot; grape black rot, rot, powdery mildew, downy mildew; power anthracnose, leaf deciduous; cucurbit anthracnose, powdery mildew, vine blight, downy mildew Tomato ring mold disease, leaf mold disease, plague; black crab disease of cruciferous vegetables; summer plague of potato; plague; strawberry powdery mildew; gray mold disease of various crops; Although it is effective in controlling diseases, it exhibits excellent control effects especially for powdery mildew and rice blast of wheat
  • Candida It is effective against the genus, Talytococcus, Aspergillus, Staphylococcus and Trichophyton.
  • the compound of the present invention is usually prepared by mixing the compound with various agricultural adjuvants, powder, granules, granule wettable powder, wettable powder, aqueous suspension, oily suspension, aqueous solvent, emulsion, It can be used in various forms such as liquids, pastes, aerosols, microdispersions, etc., but it should be in the form of any formulation that is usually used in the field as long as it meets the purpose of the present invention. Can do.
  • Adjuvants used in the formulation include solid forms such as diatomaceous earth, slaked lime, calcium carbonate, tark, white carbon, kaolin, bentonite, kaolinite and sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch, etc.
  • Carrier water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, black benzene, cyclohexane, dimethyl sulfoxide, dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, Solvents such as alcohols; fatty acid salts, benzoates, alkylsulfosuccinates, dialkylsulfosuccinates, polycarboxylic acids, alkyl sulfate esters, alkyl sulfates, alkyl aryl sulfates, alkyl diglycol ether sulfates , Arco Sulfate ester salt, alkyl sulfonate salt, alkyl aryl sulfonate salt, aryl sulfonate salt, ligne sulfonate salt, alkyl diphenyl ether disulf
  • adjuvants can be selected from those known in the art without departing from the object of the present invention.
  • various commonly used adjuvants such as extenders, thickeners, anti-settling agents, antifreezing agents, dispersion stabilizers, safeners, and antifungal agents can also be used.
  • the blending ratio of the compound of the present invention to various adjuvants is generally 0.005: 99.995 to 95: 5, preferably 0.2: 99.8 to 90:10, by weight. In actual use of these preparations, they can be used as they are, or diluted to a predetermined concentration with a diluent such as water, and various spreading agents can be added as necessary.
  • the concentration of the compound of the present invention varies depending on the target crop, method of use, formulation, application rate, etc., and cannot be generally defined. However, in the case of foliage treatment, it is usually 0.1 to 10,000 ppm, preferably L to 2,000 ppm. In the case of soil treatment, it is usually 10 to 100,000 g / ha, preferably 200 to 20,000 g / ha.
  • the compound of the present invention is generally applied for application of its various preparations or dilutions thereof, that is, spraying (eg spraying, spraying, misting, atomizing, dusting, water surface application, etc.) , Soil application (mixing, irrigation, etc.), surface application (application, powder coating, covering, etc.). It can also be applied by the so-called ultra-low-volume spray method. In this method, it is possible to contain 100% of the active ingredient.
  • the compound of the present invention may contain other agricultural chemicals such as bactericides, insecticides, acaricides, nematicides, antiviral agents, attractants, herbicides, plant growth preparations, etc., if necessary. They can be mixed and used together, and in this case, even better effects may be shown.
  • fungicide for example, mepa-pyrim (Mepanipyrim), pyrimethanil, cyprozil (Mepanipyrim), pyrimethanil, cyprozil (Mepanipyrim), pyrimethanil, cyprozil (Mepanipyrim), pyrimethanil, cyprozil (Mepanipyrim), pyrimethanil, cyprozil (Mepanipyrim), pyrimethanil, cyprozil (Mepanipyrim), pyrimethanil, cyprozil (Mepanipyrim), pyrimethanil, cyprozil (Mepanipyrim), pyrimethanil, cyprozil (Mepanipyrim), pyrimethanil, cyprozil (Mepanipyrim), pyrimethanil, cyprozil (Mepanipyrim), pyrimethanil, cyprozil (
  • Pyridinamine compounds such as Fluazinam; Triadimefon, Bitertanol, Triflumi zole, Etaconazole, Propiconazole, Penconazo, Penconazole, Flusilazole, Micro Butaninole (Myclobutanil), Cyproconazonore (Cyproconazole), Tebuconazonole (Tebuconazole), Hexaconazo Monore (Hexaconazole), Farconazonore (Furconazole-cis), Prochloraz (Prochl oraz), Metoconazonole Epoxy Epoxiconazole), Tetraconazole, Oxpoconazole ftimarate, Sipconazole, Prothioconazole, Triazimenol, Flutriafol, Difeno conazole, Norequinconazole, Fenbuconaz ole, Bromuconazole, Diniconazole, Tricyclazole, Probenazo
  • Dithio carbamate compounds such as Maneb, Zineb, Mancozeb, Polycarbamate, Metiram, Propineb, thiram;
  • Organochlorine compounds such as Fthalide, Chlorothalonil, Quintozene;
  • Imidazole compounds such as Benomyl, Thiophanate-Methyl, Carbendazim, Thiabendazole, Foveriazole, Cyazofamid;
  • Cyanoacetamide compounds such as Cymoxanil
  • Copper-based compounds such as cupric hydroxide and organic copper (Oxine Copper); isoxazole-based compounds such as hymexazol;
  • N-nologenothioalkyl compounds such as Captan, Captafol, Folpet;
  • Dicanolevoxiimide compounds such as Procymidone, Iprodione, Vinclozolin;
  • Benzalide compounds such as Flutolanil, Mepronil, Zoxamid, Tiadinil;
  • Carboxin Carboxin
  • Oxycarboxin Monocarboxin
  • Thifluzamid Thifluzamid (Thifluza mide)
  • MTF-753 Penthiopyrad, Penthiopyrad
  • Boscalid Boscalid
  • Piperazine compounds such as Triforine
  • Pyridine compounds such as Pyrifenox
  • Carbinol compounds such as Fenarimol and Flutriafol
  • Piperidine compounds such as Fenpropidine
  • Morpholine compounds such as Fenpropimorph, Spiroxamine, Tridemorph;
  • Organotin compounds such as Fentin Hydroxide and Fentin Acetate
  • Urea compounds such as Pencycuron
  • Synamic acid compounds such as Dimethomorph, Flumorph; Ferrocarbamate compounds such as Dietofencarb; Cyanopyrrole compounds such as Fludioxonil and Fenpiclonil;
  • Azoxystrobin Kresoxim-Methyl, Metominofen, Trifloxystrobin, Picoxystrobin, Oryzastrobin, Dimoxystrobin (Dimoxystrobin), pyraclostrobin, and strutovirin compounds such as Fluoxastrobin;
  • Oxazolidinone compounds such as Famoxadone
  • Thiazole carboxamide compounds such as ethaboxam
  • Silylamide compounds such as Silthiopham
  • Amino acid amide carbamate compounds such as Iprovalicarb, benchthiavalicar b-isopropyl;
  • Imidazolidine compounds such as Fenamidone
  • Hydoxyxanilide compounds such as fenhexamid
  • Benzenesulfonamide compounds such as Flusulfamid
  • Oxime ether compounds such as cyflufenamid
  • Phenoxy amide compounds such as Fenoxanil
  • Antibiotics such as Noridamycin, Kasugamycin, Polyoxins;
  • Guazine compounds such as iminoctadine
  • pesticides insecticides, acaricides, or nematicides
  • active compound compounds for example, Profenofos, Dichlorvos, Fenamiphos, Fenitr othion, EPN, Diazinon, Chlorpyrifos-methyl, Acephate, Prothiofos, Phoschiazate (Fosthiazate) Organophosphates such as Phosphocarb, Cadusafos, Dislufoton, Chlorpyrifos, Demeton-S-methyl, Dimethhoate, Methamidophos Compounds: Power Barbaryl, Propoxur, Aldicarb, Carboforan, Chi Carnots such as Thiodicarb, Methomyl, Oxamyl (0 xamyl), Ethiofencarb, Pirimicarb, Fenobucarb, Carbosul
  • active compound compounds for example, Profenofos, Dichlorvos, Fenamiphos, Fenit
  • Nereistoxin derivatives such as Cartap, Thiocyclam, Bensultap;
  • Organochlorine compounds such as Dicofol, Tetradifon, Endosulfan;
  • Organometallic compounds such as Fenbutatin Oxide
  • Penolemethrin Permethrin
  • Penolemethrin Permethrin
  • Deltamethrin Cyperme thrin
  • Cyhalothrin Cyhalothrin
  • Teflut hrin Cyhalothrin
  • Ethofenprox Flufenprox
  • Flufenprox Flufenprox Pyrethroid compounds such as Fenpropathrin, Bifenthrin, and Imidate
  • Juvenile hormone-like compounds such as methoprene
  • Pyridazinone compounds such as Pyridaben
  • Pyrazole compounds such as Fenpyroximate, Fipronil, Te bufenpyrad, Ethiprole, Tolfenpyrad, Acetoprole;
  • Hydrazine compounds such as Tebufenozide, Methoxyfenozide, Chromafenozide, Halofenozide; Pyridine compounds such as Pyridaryl, Flonicamid A tetronic acid compound such as Spirodiclofen; a streptavirline compound such as Fluacrypyrin;
  • Dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, hydrazine compounds, and other compounds include Buprofezin, Hexythiazox, Amitraz, Chlorimeform, Silafluofen, Triazamate, Pymetrozine, Pyrimidifen, Chlorfenapyr, Indoxac arb, Acequinocyl, Etoxazole, C ine), 1,3-dichloropropene, 1,3-dichloropropene, Diafenthiuron, Benclothiaz, Flufenerim, Pyridal yl, Spirodiclofen, Bifenazate, spirotetra Pine (spirotetramat), propanoregit (Propargite), benolevbutin (Verbutin), spiromesifen (Spiromesifen), thiazolyl cinano-tolyl (Thiazolylcinnanonitrile), amide-flumeme And compounds such as Amido
  • microbial pesticides such as BT agents, entomopathogenic virus agents, Avermectin, Milbemycin, Spinosad, Emamectin Benzoate, Ivermectin, Lepimectin ), Antibiotics such as Azadirachtin, and natural products such as Rotenone.
  • the ratio of developing solvent is a volume ratio
  • 1H-NMR uses CDC1 as the solvent.
  • N-methyl-3- (2, -chloro-6, -methyl-3, -trifluoromethylphenol) benzamide obtained in Synthesis Example 2 0.2 g in 10 ml of anhydrous tetrahydrofuran at 10 ° C 60% sodium hydride (0.1 lg) was added in several portions, and the mixture was stirred at the same temperature for 10 minutes. Subsequently, 0.14 ml of propargyl bromide was added at 5 ° C, and the mixture was stirred at 15 ° C for 4 hours.
  • the mixture was heated to 60 ° C and stirred at the same temperature for 4 hours. After allowing to cool, the insoluble material was filtered off, and ethyl acetate was added to the filtrate, followed by washing with a 10% aqueous solution of ammonium chloride and then with saturated saline.
  • Table 1 shows the compounds of the formula (I) produced by the method according to Synthesis Examples 1 to 13.
  • Table 2 shows compounds of the formula (V) that are intermediates for producing the compound of the formula (I) produced by the methods according to the synthesis examples 1 to 5, 7 and 12 to 13.
  • Me represents methyl
  • Et represents ethyl
  • n-Pr represents normal propyl
  • c-Pr represents cyclopropyl
  • i-Pr represents isopyl pill.
  • the substitution position of Z in Tables 1 and 2 is represented by the numbers 1 to 6 in the formulas in Table 1.
  • the mp (melting point) in the physical properties column was measured using an automatic melting point measuring apparatus (METTLER FP62 manufactured by METTLER TOLEDO).
  • reaction solution was subjected to silica gel (Kanto Chemical Co., Silica Gel 60N; spherical 'neutral) column chromatography (developing solvent n-hexane) to give crude 3-amino- After obtaining 17 g of 2,4-dichlorodibenzotrifluoride, it was purified by distillation under reduced pressure. The boiling point was 72-75 ° CZ4 mmHg.
  • the NMR of this product was as follows.
  • Table 3 shows the compounds of formula ( ⁇ ) produced according to the methods of Reference Example Intermediate Synthesis Examples 1 and 2, the method of Reference Example 1, and the production method described above.
  • Table 4 shows compounds of the formula (V ′) which are intermediates for the production of the compound of the formula ( ⁇ ).
  • Me represents methyl
  • Et represents ethyl
  • n-Pr represents normal propyl
  • i-Bu represents isobutyl
  • c-Pr represents cyclopropyl
  • Pr represents isopropyl.
  • the mp (melting point) in the physical properties column is the automatic melting point. It measured using the measuring apparatus (METTLER FP62 by METTLER TOLEDO).
  • the lesion area, number of lesions or spore formation area is less than 10% of the untreated area 3: Spot area, number of lesions or spore formation area is less than 40% of untreated area 2: Disease area, number of lesions or spore formation area is less than 70% of untreated area 1: Disease area, The number of lesions or sporulation area is 70% or more of the untreated area
  • Test Example 1 Wheat powdery mildew prevention effect test
  • Wheat (variety: Norin 61) was cultivated in a 7.5 cm diameter plastic pot, and when the 1.5 leaf stage was reached, 10 ml of a chemical solution adjusted to a predetermined concentration of the present compound was sprayed with a spray gun. After the chemical solution was dried (on the day of treatment), conidia of powdery mildew fungus were sprinkled and inoculated in a constant temperature room at 20 ° C. The spore formation area was investigated 6 to 7 days after the inoculation, and the control index was determined according to the above evaluation criteria.
  • Test Example 2 Test for prevention of mildew powdery mildew
  • Cucumbers (variety: Sagamihanjiro) were cultivated in a plastic pot with a diameter of 7.5 cm, and when the 1.5 leaf stage was reached, 10 ml of a chemical solution prepared by adjusting the compound of the present invention to a predetermined concentration was sprayed with a spray gun. After the chemical solution was dried (on the day of treatment or the next day), a conidial spore suspension of powdery mildew and powdery mildew was sprayed and kept in a constant temperature room at 20 ° C. The spore formation area was investigated 6 to 7 days after the inoculation, and the control index was determined according to the above evaluation criteria.
  • Rice (variety: Nipponbare) was cultivated in a 7.5 cm diameter plastic pot, and when the 1.5 leaf stage was reached, 10 ml of a chemical solution prepared by adjusting the compound of the present invention to a predetermined concentration was sprayed with a spray gun. After the drug solution was dried (on the day of treatment or the next day), a conidial spore suspension of blast fungus was spray-inoculated, kept in an inoculation box at 20 ° C for 24 hours, and then kept in a constant temperature room at 20 ° C. The number of lesions was investigated 6 to 11 days after the inoculation, and the control index was determined according to the above evaluation criteria. As a result, 1-2, 1-21 and 1-62 in the compound showed an effect of controlling the control index of 4 or more at 400 ppm.
  • the above is uniformly mixed to form a powder.
  • the mixture of the above components and the compound of the present invention are mixed at a weight ratio of 4: 1 to obtain a wettable powder.
  • the above is uniformly mixed and pulverized to obtain an aqueous suspension.
  • the compound of the present invention has an excellent effect for controlling plant pathogens and can be used as a bactericidal agent for agricultural and horticultural use.
  • the entire contents of the specification, claims, drawings, and abstract of Japanese Patent Application No. 2005-129320 filed on April 27, 2005 are hereby incorporated herein by reference. As it is incorporated.

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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

L'invention concerne un bactéricide pour un usage en agriculture et en horticulture, ayant un effet important et stable de contrôle des maladies des plantes. L'invention concerne spécifiquement un dérivé biphényle représenté par la formule (I) ci-dessous ou un de ses sels. (I) (Dans la formule, X et Y1 représentent indépendamment un atome d'halogène, un groupe alkyle ou analogue ; Y2 représente un groupe haloalkyle, un groupe haloalkoxy, ou un atome de brome ; Z représente un atome d'halogène, un groupe formyle ou un groupe alkyle pouvant être substitué par un atome d’halogène ; A représente un groupe carbonyle, un groupe thiocarbonyle, ou une liaison simple ; R1 et R2 représentent indépendamment un atome d'hydrogène, un groupe alkyle éventuellement substitué, un groupe alcényle éventuellement substitué, un groupe alkynyle éventuellement substitué, un groupe alkoxy éventuellement substitué, un groupe aryle éventuellement substitué, un groupe alkylcarbonyle éventuellement substitué, un groupe alkénylcarbonyle éventuellement substitué, un groupe formyle ou analogue ; et n représente un entier compris entre 0 et 4.)
PCT/JP2006/308764 2005-04-27 2006-04-26 Derive de biphenyle ou son sel, et bactericide pour un usage en agriculture et en horticulture le contenant en tant que principe actif WO2006118155A1 (fr)

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010032147A3 (fr) * 2008-09-19 2010-06-03 Pfizer Inc. Dérivés d'acide hydroxamique utiles comme agents antibactériens
JP2010523593A (ja) * 2007-04-06 2010-07-15 ニューロクライン バイオサイエンシーズ，インコーポレイテッド ゴナドトロピン放出ホルモン受容体拮抗薬およびそれに関連する方法
US8624034B2 (en) 2011-03-07 2014-01-07 Pfizer Inc. Fluoro-pyridinone derivatives useful as antibacterial agents
US8664401B2 (en) 2009-12-16 2014-03-04 Pfizer Inc. N-linked hydroxamic acid derivatives useful as antibacterial agents
US8748466B2 (en) 2011-04-08 2014-06-10 Pfizer Inc. Isoxazole derivatives useful as antibacterial agents
US8809333B2 (en) 2011-04-08 2014-08-19 Pfizer Inc. Imidazole, pyrazole, and triazole derivatives useful as antibacterial agents
CN109608341A (zh) * 2018-12-28 2019-04-12 西南交通大学 一种芳基苯胺化合物及其制备方法

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JPH11152259A (ja) * 1997-08-26 1999-06-08 Kumiai Chem Ind Co Ltd ビアリールアルキレンカルバミン酸誘導体及び農園芸用殺菌剤
WO2005044007A1 (fr) * 2003-11-11 2005-05-19 Ishihara Sangyo Kaisha, Ltd. Derive de diphenyle ou ses sels, et pesticide dont il constitue le principe actif

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
JPH11152259A (ja) * 1997-08-26 1999-06-08 Kumiai Chem Ind Co Ltd ビアリールアルキレンカルバミン酸誘導体及び農園芸用殺菌剤
WO2005044007A1 (fr) * 2003-11-11 2005-05-19 Ishihara Sangyo Kaisha, Ltd. Derive de diphenyle ou ses sels, et pesticide dont il constitue le principe actif

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8952161B2 (en) 2007-04-06 2015-02-10 Neurocrine Biosciences, Inc. Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
JP2010523593A (ja) * 2007-04-06 2010-07-15 ニューロクライン バイオサイエンシーズ，インコーポレイテッド ゴナドトロピン放出ホルモン受容体拮抗薬およびそれに関連する方法
US11713324B2 (en) 2007-04-06 2023-08-01 Neurocrine Biosciences, Inc. Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
US10941159B2 (en) 2007-04-06 2021-03-09 Neurocrine Biosciences, Inc. Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
US10336769B2 (en) 2007-04-06 2019-07-02 Neurocrine Biosciences, Inc. Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
US9422310B2 (en) 2007-04-06 2016-08-23 Neurocrine Biosciences, Inc. Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
US9340493B2 (en) 2008-09-19 2016-05-17 Pfizer Inc. Hydroxamic acid derivatives useful as antibacterial agents
WO2010032147A3 (fr) * 2008-09-19 2010-06-03 Pfizer Inc. Dérivés d'acide hydroxamique utiles comme agents antibactériens
US8722686B2 (en) 2008-09-19 2014-05-13 Pfizer Inc. Hydroxamic acid derivatives useful as antibacterial agents
US8846933B2 (en) 2009-12-16 2014-09-30 Pfizer Inc. N-link hydroxamic acid derivatives useful as antibacterial agents
US9018384B2 (en) 2009-12-16 2015-04-28 Pfizer Inc. N-link hydroxamic acid derivatives useful as antibacterial agents
US9180123B2 (en) 2009-12-16 2015-11-10 Pfizer Inc. N-link hydroxamic acid derivatives useful as antibacterial agents
US8664401B2 (en) 2009-12-16 2014-03-04 Pfizer Inc. N-linked hydroxamic acid derivatives useful as antibacterial agents
US8779148B2 (en) 2011-03-07 2014-07-15 Pfizer Inc. Fluoro-pyridinone derivatives useful as antibacterial agents
US8624034B2 (en) 2011-03-07 2014-01-07 Pfizer Inc. Fluoro-pyridinone derivatives useful as antibacterial agents
US8809333B2 (en) 2011-04-08 2014-08-19 Pfizer Inc. Imidazole, pyrazole, and triazole derivatives useful as antibacterial agents
US8748466B2 (en) 2011-04-08 2014-06-10 Pfizer Inc. Isoxazole derivatives useful as antibacterial agents
CN109608341A (zh) * 2018-12-28 2019-04-12 西南交通大学 一种芳基苯胺化合物及其制备方法

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