WO2022001998A1 - Dérivé de diarylamine utilisé comme fongicide - Google Patents

Dérivé de diarylamine utilisé comme fongicide Download PDF

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WO2022001998A1
WO2022001998A1 PCT/CN2021/102896 CN2021102896W WO2022001998A1 WO 2022001998 A1 WO2022001998 A1 WO 2022001998A1 CN 2021102896 W CN2021102896 W CN 2021102896W WO 2022001998 A1 WO2022001998 A1 WO 2022001998A1
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spot
acid
blight
disease
leaf
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PCT/CN2021/102896
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Chinese (zh)
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周银平
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周银平
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • C07D413/12—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 linked by a chain containing hetero atoms as chain links

Definitions

  • the present disclosure relates to the technical field of sterilization, in particular to a diarylamine derivative used as a fungicide.
  • Chinese patents have reported compounds related to antibiotics, the structures of these compounds are quite different from the compounds of this patent, and such structures are only used for bacterial control.
  • the present disclosure provides a diarylamine derivative used as a fungicide, and the structural formula of the diarylamine derivative is as follows:
  • R 1 and R 2 can be the same or different, and are respectively selected from hydrogen, halogen, cyano, C1-C12 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, and halogenated C1-C4 alkoxy base, C1-C4 alkylamino, C1-C4 alkylthio, C1-C4 alkylsulfonyl;
  • R 3 is selected from hydrogen, potassium, sodium, calcium, C1-C4 alkyl, halo C1-C4 alkyl, C1-C4 alkylcarbonyl group, halo C1-C4 alkylcarbonyl, C1-C4 alkoxycarbonyl group, Halogenated C1-C4 alkoxycarbonyl, C1-C4 alkylaminocarbonyl, halogenated C1-C4 alkylaminocarbonyl, C1-C4 alkylsulfonyl, halogenated C1-C4 alkylsulfonyl;
  • X is selected from O, S or NR 5 ;
  • R 4 is one or more substituents, each independently selected from halogen, cyano, NO 2 , carboxyl, hydroxyl, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, Halogenated C1-C4 alkoxy, C1-C4 alkyl C1-C4 alkoxy, C1-C4 alkoxy C1-C4 alkoxy, C1-C4 alkoxycarbonyl, halogenated C1-C4 alkoxy Carbonyl, C1-C4 alkylaminocarbonyl, halogenated C1-C4 alkylaminocarbonyl, C1-C4 alkylsulfonyl, halogenated C1-C4 alkylsulfonyl;
  • R 5 is selected from hydrogen, C1-C4 alkyl
  • the diarylamine derivative does not include compound A, and the structural formula of compound A is as follows:
  • R 1 and R 2 may be the same or different, and are respectively selected from hydrogen, halogen, and cyano;
  • Said R 3 is selected from hydrogen, potassium, sodium, calcium, C1-C4 alkyl
  • the X is selected from O or NR 5 ;
  • the R 4 is one or more substituents, each independently selected from halogen, cyano, NO 2 , carboxyl, hydroxyl, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy , halogenated C1-C4 alkoxy, C1-C4 alkyl C1-C4 alkoxy, C1-C4 alkoxy C1-C4 alkoxy, C1-C4 alkoxycarbonyl, halogenated C1-C4 alkoxy carbonyl, C1-C4 alkylaminocarbonyl, halogenated C1-C4 alkylaminocarbonyl, C1-C4 alkylsulfonyl, halogenated C1-C4 alkylsulfonyl;
  • R 5 is selected from hydrogen.
  • R 1 and R 2 can be the same or different, and are respectively selected from H, F, Cl, Br, and I;
  • Said R 3 is selected from hydrogen, potassium, sodium;
  • the X is selected from O or NR 5 ;
  • the R 4 is one or more substituents, each independently selected from fluorine, chlorine, bromine or iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, isopropyl, sec-butyl, tertiary Butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy, trifluoromethoxy, carboxyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl, methanesulfonyl acyl;
  • Said R 5 is selected from hydrogen.
  • R 1 and R 2 can be the same or different, and are respectively selected from H, F, Cl, and Br;
  • Said R 3 is selected from hydrogen, potassium, sodium;
  • the X is selected from O or NR 5 ;
  • the R 4 is one or more substituents, each of which is independently selected from fluorine, chlorine, bromine, hydroxyl, cyano, methyl, ethyl, n-propyl, isopropyl, sec-butyl, tert-butyl group, trifluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy, trifluoromethoxy, carboxyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl, methanesulfonyl ;
  • Said R 5 is selected from hydrogen.
  • R 1 and R 2 can be the same or different, and are respectively selected from H, F, Cl, and Br;
  • Said R 3 is selected from hydrogen, potassium, sodium;
  • the X is selected from O or NR 5 ;
  • the R 4 is one or more substituents, each independently selected from fluorine, chlorine, bromine, hydroxyl, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, iso Propoxy, trifluoromethoxy, carboxyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl;
  • Said R 5 is selected from hydrogen.
  • the present disclosure provides a salt obtained by reacting the diarylamine derivative with an acid or a base.
  • the acid includes at least one of the following: an organic acid or an inorganic acid;
  • the organic acid includes at least one of the following: carboxylic acid, such as acetic acid, propionic acid, butyric acid, oxalic acid, adipic acid, dodecanedioic acid, lauric acid, stearic acid, trifluoroacetic acid, fumaric acid, Maleic, benzoic or phthalic acid, sulfonic acids, such as methanesulfonic acid, 1,3-propanedisulfonic acid, p-toluenesulfonic acid or dodecylbenzenesulfonic acid;
  • carboxylic acid such as acetic acid, propionic acid, butyric acid, oxalic acid, adipic acid, dodecanedioic acid, lauric acid, stearic acid, trifluoroacetic acid, fumaric acid, Maleic, benzoic or phthalic acid
  • sulfonic acids such as methanesulfonic acid, 1,3-
  • the inorganic acid includes at least one of the following: hydrochloric acid, sulfuric acid, nitric acid or carbonic acid.
  • the alkali includes at least one of the following: sodium hydroxide, potassium hydroxide, calcium hydroxide, lithium hydroxide, potassium carbonate, sodium carbonate, sodium bicarbonate, potassium bicarbonate, sodium metal, sodium hydride, Sodium amide, butyl lithium.
  • the present disclosure provides the application of the diarylamine derivative or the salt of claim 6 in controlling fungal diseases.
  • the fungal diseases include downy mildew, white rust, damping off, cotton rot, blight, late blight, fusarium wilt, root rot, blight, anthracnose, verticillium wilt, scab , Botrytis, brown spot, black spot, leaf blight, early blight, ring disease, rice blast, rust, smut, powdery mildew or sclerotinia.
  • the fungal diseases include leaf blight, stem base rot, corn round spot, kenaf lumbar fold disease, millet black sheath disease, sugarcane eye spot disease, cotton boll aspergillosis, peanut crown rot, soybean stem Blight, soybean black spot, melon large spot, peanut net spot, tea red leaf spot, pepper white spot, wax gourd leaf spot, celery black rot, spinach heart rot, kenaf leaf mildew, red leaf spot Hemp spot, jute stem spot, soybean purple spot, sesame leaf spot, castor grey spot, tea-brown leaf spot, eggplant brown spot, kidney bean red spot, bitter gourd white spot, watermelon spot, jute rot Disease, sunflower rhizome rot, bean char rot, soybean target spot disease, eggplant Corynebacterium leaf spot, cucumber target leaf spot, tomato leaf mold, eggplant leaf mold, broad bean red spot.
  • the present disclosure provides a germicidal composition containing the diarylamine derivative as an active component.
  • the weight percentage of the active ingredient in the bactericidal composition is 0.1-99%.
  • the composition includes active ingredients compatible with the diarylamine derivative, the active ingredients include pesticides, fungicides, plant growth regulators, antibiotics, herbicides, fertilizers.
  • the use forms of the composition include dry powders, wettable powders, emulsifiable concentrates, microemulsions, pastes, granules, solutions, suspensions, and water-dispersible granules.
  • the present disclosure provides the application of the fungicidal composition in controlling fungal diseases.
  • the fungal diseases include downy mildew, white rust, damping off, cotton rot, blight, late blight, fusarium wilt, root rot, blight, anthracnose, verticillium wilt, scab , gray mold, brown spot, black spot, leaf blight, early blight, ring disease, rice blast, rust, smut, powdery mildew, sclerotinia, leaf blight, stem rot, corn Round spot disease, kenaf lumbar fold disease, millet black sheath disease, sugarcane eye spot disease, cotton boll aspergillosis, peanut crown rot, soybean stem blight, soybean black spot disease, melon large leaf spot disease, peanut web spot disease, tea Red leaf spot, pepper white spot, wax gourd leaf spot, celery black rot, spinach heart rot, kenaf leaf mold, kenaf spot, jute stem spot, soybean purple spot, sesame leaf spot, castor
  • the present disclosure provides a diarylamine derivative used as a fungicide, which can effectively control diseases caused by downy mildew, blight, anthracnose, rust and the like as a fungicide.
  • One embodiment of the present disclosure provides a diarylamine derivative used as a fungicide, and the general structural formula is as follows:
  • R 1 and R 2 may be the same or different, and are each independently selected from hydrogen, halogen, cyano, C1-C12 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, and halogenated C1-C4 alkane Oxy group, C1-C4 alkylamino group, C1-C4 alkylthio group, C1-C4 alkylsulfonyl group;
  • R 3 is selected from hydrogen, potassium, sodium, calcium, C1-C4 alkyl, halo C1-C4 alkyl, C1-C4 alkylcarbonyl group, halo C1-C4 alkylcarbonyl, C1-C4 alkoxycarbonyl group, Halogenated C1-C4 alkoxycarbonyl, C1-C4 alkylaminocarbonyl, halogenated C1-C4 alkylaminocarbonyl, C1-C4 alkylsulfonyl, halogenated C1-C4 alkylsulfonyl;
  • X is selected from O, S or NR 5 ;
  • R 4 is one or more substituents, each independently selected from halogen, cyano, NO2, carboxyl, hydroxyl, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkoxy, C1-C4 alkoxy, C1-C4 alkoxycarbonyl, halogenated C1-C4 alkoxycarbonyl, C1-C4 alkylaminocarbonyl, halogenated C1-C4 alkylaminocarbonyl, C1-C4 alkylsulfonyl, halogenated C1-C4 alkylsulfonyl;
  • R 5 is selected from hydrogen, C1-C4 alkyl
  • the diarylamine derivative does not include compound A, and the structural formula of compound A is as follows:
  • the diarylamine derivative is:
  • R 1 and R 2 may be the same or different, and are independently selected from hydrogen, halogen and cyano;
  • R 3 is selected from hydrogen, potassium, sodium, calcium, C1-C4 alkyl
  • X is selected from O or NR 5 ;
  • R 4 is one or more substituents, each independently selected from halogen, cyano, NO2, carboxyl, hydroxyl, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkoxy, C1-C4 alkoxy, C1-C4 alkoxycarbonyl, halogenated C1-C4 alkoxycarbonyl, C1-C4 alkylaminocarbonyl, halogenated C1-C4 alkylaminocarbonyl, C1-C4 alkylsulfonyl, halogenated C1-C4 alkylsulfonyl;
  • R 5 is selected from hydrogen.
  • the diarylamine derivative is:
  • R 1 and R 2 can be the same or different, and are independently selected from H, F, Cl, Br, and I;
  • R 3 is selected from hydrogen, potassium, sodium
  • X is selected from O or NR 5 ;
  • R 4 is one or more substituents, each independently selected from fluorine, chlorine, bromine or iodine, hydroxy, cyano, methyl, ethyl, n-propyl, isopropyl, sec-butyl, tert-butyl , trifluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy, trifluoromethoxy, carboxyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl, methanesulfonyl;
  • R 5 is selected from hydrogen.
  • the diarylamine derivative is:
  • R 1 and R 2 can be the same or different, and are respectively selected from H, F, Cl, and Br;
  • R 3 is selected from hydrogen, potassium, sodium
  • X is selected from O or NR 5 ;
  • R 4 is one or more substituents, each independently selected from fluorine, chlorine, bromine, hydroxyl, cyano, methyl, ethyl, n-propyl, isopropyl, sec-butyl, tert-butyl, tri- Fluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy, trifluoromethoxy, carboxyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl, methanesulfonyl;
  • R 5 is selected from hydrogen.
  • the diarylamine derivative is:
  • R 1 and R 2 may be the same or different, and are independently selected from H, F, Cl, and Br;
  • R 3 is selected from hydrogen, potassium, sodium
  • X is selected from O or NR 5 ;
  • R 4 is one or more substituents, each independently selected from fluorine, chlorine, bromine, hydroxy, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, isopropoxy , trifluoromethoxy, carboxyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl;
  • R 5 is selected from hydrogen.
  • stereoisomers can be formed due to the attachment of different groups or substituents to chiral carbons or nitrogens (R and S represent different configurations, respectively).
  • R and S represent different configurations, respectively.
  • the present disclosure includes the R-isomer and S-isomer and mixtures thereof in any ratio.
  • halogen refers to fluorine, chlorine, bromine or iodine.
  • alkyl straight chain, branched chain or cyclized alkyl such as methyl, ethyl, propyl, isopropyl, tert-butyl or cyclopropyl.
  • Haloalkyl straight or branched chain haloalkyl, the hydrogen atoms on these alkyl groups may be partially or fully substituted by halogen atoms, for example, haloalkyl groups such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl group, difluoromethyl or trifluoromethyl.
  • Alkoxy Linear, branched or cyclic alkoxy, for example methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy or cyclopropoxy.
  • Haloalkoxy straight or branched chain haloalkoxy, the hydrogen atoms in these alkoxy groups may be partially or fully substituted by halogen atoms, for example, haloalkyl groups such as chloromethoxy, dichloromethoxy, trichloro Methoxy, fluoromethoxy, difluoromethoxy or trifluoromethoxy.
  • Alkylthio A straight or branched chain alkyl group attached to the structure via a sulfur atom bond.
  • Halogenated alkylthio group straight-chain or branched-chain alkylthio group, the hydrogen atoms on these alkylthio groups may be partially or totally substituted by halogen atoms.
  • halogen atoms for example, chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio and the like.
  • the diarylamine derivatives are salts obtained by reacting with acids or bases.
  • the acids that can form salts with the diarylamine derivatives of the present disclosure include at least one of the following: organic acids, such as carboxylic acids, such as acetic acid, propionic acid, butyric acid, Oxalic acid, adipic acid, dodecanedioic acid, lauric acid, stearic acid, trifluoroacetic acid, fumaric acid, maleic acid, benzoic or phthalic acid, sulfonic acids such as methanesulfonic acid, 1,3- propanedisulfonic acid, p-toluenesulfonic acid or dodecylbenzenesulfonic acid; and inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid or carbonic acid.
  • organic acids such as carboxylic acids, such as acetic acid, propionic acid, butyric acid, Oxalic acid, adipic acid, dodecanedioic acid, lauric acid, stearic acid,
  • bases that can form salts with the diarylamine derivatives of the present disclosure include at least one of the following: sodium hydroxide, potassium hydroxide, calcium hydroxide, lithium hydroxide, carbonic acid Potassium, sodium carbonate, sodium bicarbonate, potassium bicarbonate, sodium metal, sodium hydride, sodium amide, butyllithium, etc.
  • the diarylamine derivatives of the present disclosure can be prepared according to the following methods:
  • L is an easily leaving group such as F, Cl, and Br.
  • (formula a) is reacted with a substituted pyridazineamine (formula b) in the presence or absence of a base, preferably using a solvent.
  • the reaction temperature is preferably 0 to 150°C, and the reaction time is 30 minutes to 20 hours, preferably 0.5 to 10 hours.
  • the solvent is any inert solvent that has no direct effect on the reaction, including aromatic hydrocarbons, such as benzene, toluene, and xylene; ketones, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; halogenated hydrocarbons, such as dichloromethane, chloroform, and dichloromethane.
  • Ethyl chloride lipids such as methyl acetate and ethyl acetate; and polar solvents such as tetrahydrofuran, acetonitrile, dioxane, N,N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and pyridine.
  • lipids such as methyl acetate and ethyl acetate
  • polar solvents such as tetrahydrofuran, acetonitrile, dioxane, N,N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and pyridine.
  • the bases include metal hydrides such as sodium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium amide; organic amines such as pyridine and triethylamine.
  • the solvent is distilled off under reduced pressure, water is added to the resulting residue, and water-insoluble aromatic hydrocarbons such as benzene, toluene are used. and xylene; halogenated alkanes such as chloroform and dichloromethane; and esters such as ethyl acetate.
  • the resulting extract was dried and the solvent was removed under reduced pressure.
  • the diarylamine derivatives of the present disclosure show excellent activity against various diseases in the agricultural field.
  • the examples of diseases mentioned below are only used to illustrate the present disclosure, but in no way limit the present disclosure.
  • the diarylamine derivatives of the present disclosure can be used to control the following diseases: Oomycetes diseases, such as downy mildew (cucumber downy mildew, rape downy mildew, soybean downy mildew, sugar beet downy mildew, sugarcane downy mildew, tobacco downy mildew Downy mildew, pea downy mildew, loofah downy mildew, wax gourd downy mildew, melon downy mildew, cabbage downy mildew, spinach downy mildew, radish downy mildew, grape downy mildew, onion downy mildew) , White rust (rape white rust, cabbage-like white rust), damping off (rape damping, tobacco damping, tomato damping, pepper damping, eggplant damping, cucumber damping, cotton seedlings Damping disease), cotton rot (hot pepper cotton rot, loofah cotton rot, wax gourd cotton rot), blight (broad bean
  • the diarylamine derivatives of the present disclosure have good bactericidal activity, and can be advantageously used to protect crops, livestock and breeding animals important to agriculture and horticulture, as well as environments frequented by humans from pathogens.
  • the diarylamine derivatives are used to prepare fungicides for controlling fungal diseases.
  • the fungal diseases are downy mildew, white rust, damping-off, cotton rot, blight, late blight, fusarium wilt, root rot, blight, anthracnose, verticillium wilt, scab, botrytis , brown spot, black spot, leaf blight, early blight, ring disease, rice blast, rust, smut, powdery mildew or sclerotinia.
  • the fungal diseases further include leaf blight, stem base rot, corn blight, kenaf lumbar fold, millet black sheath disease, sugarcane eye spot disease, cotton boll aspergillosis, peanut crown rot , soybean stem blight, soybean black spot, melon large spot, peanut net spot, tea red leaf spot, pepper white spot, wax gourd leaf spot, celery black rot, spinach heart rot, kenaf leaf mold Disease, kenaf spot, jute stem spot, soybean purple spot, sesame leaf spot, castor gray spot, tea-brown leaf spot, eggplant brown spot, kidney bean red spot, bitter gourd white spot, watermelon spot, Jute blight rot, sunflower rhizome rot, bean char rot, soybean target spot disease, eggplant corynebacterium leaf spot, cucumber target spot disease, tomato leaf mold, eggplant leaf mold, broad bean red spot.
  • the amount of compound to be used to obtain the desired effect will vary depending on factors such as compound used, crop to be protected, type of pest, degree of infestation, climatic conditions, method of application, dosage form employed.
  • dosages of 10 grams to 1000 grams of the diarylamine derivative per hectare provide adequate control.
  • One embodiment of the present disclosure provides a method of diarylamine derivatives for controlling agricultural and horticultural important crops and/or phytopathogenic fungi in environments frequented by livestock and breeding stock and/or humans.
  • the dosage of the compound varied from 10 grams to 1000 grams per hectare.
  • compositions containing one or more of the diarylamine derivatives of the present disclosure For practical use in agriculture, it is often beneficial to use compositions containing one or more of the diarylamine derivatives of the present disclosure.
  • an embodiment of the present disclosure provides a bactericidal composition containing one or more diarylamine derivatives as an active ingredient, and the weight percentage of the active ingredient in the composition is 0.1-99%.
  • An embodiment of the present disclosure provides the use of the bactericidal composition for preparing and controlling fungal diseases.
  • the fungal diseases are the same as the types of fungal diseases controlled by the diarylamine derivatives described above.
  • composition can be used in the form of dry powder, wettable powder, emulsifiable concentrate, microemulsion, paste, granule, solution, suspension, water dispersible granule, etc.
  • the choice of composition type depends on the specific application.
  • compositions are prepared by known methods, eg by diluting or dissolving the active substance with a solvent medium and/or solid diluent, optionally in the presence of a surfactant.
  • useful solid diluents or carriers are, for example, silica, kaolin, bentonite, talc, diatomaceous earth, dolomite, calcium carbonate, magnesium oxide, chalk, clay, synthetic silicates, magnesium silicates Soil, sepiolite, etc.
  • useful liquid diluents in addition to water include, for example, aromatic organic solvents (mixtures of xylenes or alkylbenzenes, chlorobenzene, etc.), paraffins (petroleum fractions), alcohols (methanol, propanol) , butanol, octanol, glycerol), esters (ethyl acetate, isobutyl acetate, etc.), ketones (cyclohexanone, acetone, acetophenone, isophorone, ethyl amyl ketone, etc.), Amides (N,N-dimethylformamide, N-methylpyrrolidone, etc.).
  • aromatic organic solvents mixture of xylenes or alkylbenzenes, chlorobenzene, etc.
  • paraffins petroleum fractions
  • alcohols methanol, propanol
  • butanol, octanol glycerol
  • useful surfactants include sodium such as alkylsulfonates, alkylarylsulfonates, polyoxyethylene alkylphenols, polyoxyethylene esters of sorbitol, lignosulfonates, and the like , calcium, triethylamine or triethanolamine salts.
  • the composition may also contain specific additives for specific purposes, such as binders such as gum arabic, polyvinyl alcohol, polyvinylpyrrolidone, and the like.
  • binders such as gum arabic, polyvinyl alcohol, polyvinylpyrrolidone, and the like.
  • the concentration of the active ingredient in the above compositions can vary widely depending on, for example, the active ingredient, the purpose of use, the environmental conditions and the type of formulation employed.
  • the active ingredient concentration is usually in the range of 0.1-99%, preferably 5-60%.
  • other active ingredients compatible with the diarylamine derivatives of the present disclosure such as other acaricides/insecticides, fungicides, plant growth regulators, Antibiotics, herbicides, fertilizers.
  • the form of the composition is not limited thereto, and one or two or more of the compounds in combination may be mixed as an active ingredient.
  • suspending agent The active ingredient content in common formula is 5-35%.
  • Solvents with water as medium such as water suspension, microemulsion, water emulsion, add the original drug, dispersing agent, suspending agent and antifreeze into a sand mill, and grind to make a suspension.
  • Preparation of water emulsion add the original drug, solvent and emulsifier together to dissolve into a homogeneous oil phase. Mix together water, antifreeze, etc. to form a homogeneous aqueous phase. Under high-speed stirring, the water phase is added to the oil phase or the oil phase is added to the water phase to form a water emulsion with good dispersibility.
  • the active ingredient content of the aqueous emulsion of the present disclosure is generally 5% to 15%.
  • the diarylamine derivatives of the present disclosure can be dissolved in one or several mixed solvents, and then an emulsifier can be added to enhance the dispersion effect of the compound in water.
  • Preparation of wettable powder According to the requirements of the formula, fully mix the original drug, various surfactants and solid diluents, etc., and pulverize by an ultra-fine pulverizer to obtain a wettable powder with a predetermined content (for example, 10-60%). product.
  • a predetermined content for example, 10-60%.
  • the diarylamine derivatives of the present disclosure can be mixed with finely divided solid powders such as clays, inorganic silicates, carbonates and wetting, binder and/or dispersing agents Make up the mixture.
  • Preparation of water-dispersible granules Mix and pulverize the original drug, powdered solid diluent, wetting and spreading agent, and binder, add water and knead, and then add it to a granulator equipped with a certain size of screen. Granulated, then dried and sieved (according to the screen range).
  • the original drug, dispersing agent, disintegrating agent, wetting agent and solid diluent can also be added to a sand mill, ground with water as a medium to make a suspension, and then spray-dried and granulated.
  • the preparation content is 20- 30% granular product.
  • the components of 30% wettable powder are as follows:
  • Compound 2 and other components listed in this example are thoroughly mixed, and after being pulverized by an ultrafine pulverizer, a 30% wettable powder product is obtained.
  • the components of the 40% suspension concentrate are as follows:
  • Compound 1 and the other components listed in this example are thoroughly mixed to obtain a concentrated suspending agent, which can be diluted with water to obtain a dilution of any desired concentration.
  • Compound 23 and other components listed in this example were mixed and pulverized, and after adding water and kneading, added to a granulator with a 10-100 mesh screen for granulation, and then dried and sieved (according to the range of the screen mesh). ).
  • the diarylamine derivatives disclosed in the present disclosure have good activity against various pathogens in the agricultural field.
  • the activity test method and some measurement results are as follows.
  • the in vivo potted assay method was used.
  • the original drug of the compound to be tested is dissolved with a small amount of acetone (the volume ratio of acetone to the sprayed liquid is equal to 0.05), and diluted with water containing 0.1% Tween 80 to the desired concentration.
  • Spray application to plant test material, and disease inoculation is carried out 24 hours later.
  • the plants were cultured in an artificial climate chamber, and 24 hours later, the plant specimens were transferred to a greenhouse for culture. After the control is fully developed (usually one week), the evaluation of the compound's disease prevention effect is carried out.
  • the evaluation method of compound disease prevention effect is as follows:
  • ⁇ fungal infection percentage of treated crops
  • ⁇ fungal infection percentage of untreated (blank) crops
  • An efficacy of "0" indicates that the infestation level of the treated crop is the same as that of the untreated control crop; an efficacy of "100" indicates that the treated crop is not infested.
  • the compounds of the present disclosure have good control effects on important diseases that endanger agricultural production, and have broad application prospects.
  • the present disclosure provides a diarylamine derivative used as a fungicide, a salt thereof, and a bactericidal composition, which have good control effects on important diseases that endanger agricultural production, especially cucumber downy mildew and blight , rust and other diseases are very effective, with good technical effects of low dose and high efficiency, and has broad application prospects.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un dérivé de diarylamine utilisé comme fongicide, la formule générale structurale du dérivé de diarylamine étant présentée comme suit. Le composé décrit présente une activité bactéricide satisfaisante, est très efficace contre les affections végétales provoquées par le mildiou du concombre, la maladie des taches brunes, la rouille et analogues, présente un meilleur effet de lutte contre le mildiou du concombre et la maladie des taches brunes en particulier, permet d'obtenir un effet satisfaisant à une dose très faible et présente de vastes perspectives d'application.
PCT/CN2021/102896 2020-07-01 2021-06-29 Dérivé de diarylamine utilisé comme fongicide WO2022001998A1 (fr)

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CN202010629681.3A CN113045561B (zh) 2020-07-01 2020-07-01 用作杀真菌剂的二芳胺衍生物

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114903060A (zh) * 2022-05-31 2022-08-16 长江师范学院 一种防治茎瘤芥黑斑病的中草药及复配农药

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH610183A5 (en) * 1971-12-24 1979-04-12 Marktredwitz Chem Fab Ag Fungicidal composition
EP0244705A2 (fr) * 1986-04-30 1987-11-11 Hoechst Aktiengesellschaft Benzoxazolyl- et benzthiazolylanilines, leur procédé de préparation et leur utilisation comme agents fongicides
CN1333768A (zh) * 1998-11-17 2002-01-30 组合化学工业株式会社 嘧啶基苯并咪唑和三嗪基苯并咪唑衍生物及农业/园艺杀菌剂
WO2010096314A1 (fr) * 2009-02-18 2010-08-26 Amgen Inc. Composés d'indole ou benzimidazole convenant comme inhibiteurs de la kinase mtor

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109053693B (zh) * 2018-09-20 2021-02-05 顺毅股份有限公司 哒嗪胺类化合物的制备及其应用

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH610183A5 (en) * 1971-12-24 1979-04-12 Marktredwitz Chem Fab Ag Fungicidal composition
EP0244705A2 (fr) * 1986-04-30 1987-11-11 Hoechst Aktiengesellschaft Benzoxazolyl- et benzthiazolylanilines, leur procédé de préparation et leur utilisation comme agents fongicides
CN1333768A (zh) * 1998-11-17 2002-01-30 组合化学工业株式会社 嘧啶基苯并咪唑和三嗪基苯并咪唑衍生物及农业/园艺杀菌剂
WO2010096314A1 (fr) * 2009-02-18 2010-08-26 Amgen Inc. Composés d'indole ou benzimidazole convenant comme inhibiteurs de la kinase mtor

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114903060A (zh) * 2022-05-31 2022-08-16 长江师范学院 一种防治茎瘤芥黑斑病的中草药及复配农药

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