WO2021120992A1 - Triazole derivatives and application thereof - Google Patents

Triazole derivatives and application thereof Download PDF

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WO2021120992A1
WO2021120992A1 PCT/CN2020/131020 CN2020131020W WO2021120992A1 WO 2021120992 A1 WO2021120992 A1 WO 2021120992A1 CN 2020131020 W CN2020131020 W CN 2020131020W WO 2021120992 A1 WO2021120992 A1 WO 2021120992A1
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alkyl
halogenated
alkoxy
alkylthio
alkoxycarbonyl
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PCT/CN2020/131020
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French (fr)
Chinese (zh)
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周繁
冉兆晋
孙朝辉
毛志强
王芳
王志祥
崔顺艳
侯薪鑫
王宇
石凯强
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沈阳化工研究院有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D411/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
    • Y02A40/10—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in agriculture

Definitions

  • the invention belongs to the field of chemistry, specifically a triazole derivative, and the application of the derivative in plant growth regulation and fungicides.
  • Paclobutrazol is a plant growth regulator, which has the effects of delaying plant growth, inhibiting stem elongation, shortening internodes, promoting plant tillering, increasing plant resistance to stress, and increasing yield.
  • soil half-life is 0.5-1.0 years
  • the purpose of the present invention is a triazole derivative and its application.
  • a triazole derivative which is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
  • R 1 is selected from pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, oxazolyl, isoxazole containing C, N, O or S substituted by 1-5 R 8 Heteroaryl groups such as thiazolyl, thiazolyl, isothiazolyl, oxadiazolyl or thiadiazolyl;
  • R 6 and R 7 which are the same or different are selected from hydrogen, hydroxyl, amino, C 1 -C 12 alkyl, halogenated C 1 -C 12 alkyl, C 1 -C 12 alkoxy or halogenated C 1- C 12 alkoxy, C 1 -C 12 alkylamino, halogenated C 1 -C 12 alkylamino;
  • R 6 , R 7 can also be connected to the N to form a three-membered, four-membered, five-membered, six-membered, seven-membered or eight-membered heterocycloalkane containing C, N, O or S;
  • the triazole derivative is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
  • R 1 is selected from pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, oxazolyl, isoxazole containing C, N, O or S substituted by 1-5 R 8 Heteroaryl groups such as thiazolyl, thiazolyl, isothiazolyl, oxadiazolyl or thiadiazolyl;
  • R 2 is selected from H, halogen, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl , C 1 -C 6 alkoxy C 1 -C 6 alkyl, halogenated C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylthio C 1 -C 6 alkyl , Halogenated C 1 -C 6 alkylthio C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, halogenated C 1 -C 6 alkoxycarbonyl C 1- C 6 alkyl, C 1 -C 6 alkylthiocarbonyl C 1 -C 6 alkyl or halogenated C 1 -C 6 alkylthiocarbonyl C 1 -C 6 al
  • R 3 is selected from H, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl, halogenated C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylthio C 1 -C 6 alkyl, halogen C 1 -C 6 alkylthio C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, halogenated C 1 -C 6 alkoxycarbonyl C 1 -C 6 Alkyl, C 1 -C 6 alkylthiocarbonyl C 1 -C 6 alkyl or halogenated C 1 -C 6 alkylthiocarbonyl C 1 -C 6 alkyl;
  • R 4 and R 5 are the same or different selected from H, halogen, hydroxy, amino, nitro, cyano, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl, halogenated C 1 -C 6 alkoxy C 1 -C 6 alkyl , C 1 -C 6 alkylthio C 1 -C 6 alkyl, halogenated C 1 -C 6 alkylthio C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkane Group, halogenated C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, C 1 -C 6 alkylthiocarbonyl C 1 -C 6 alkyl,
  • R 6 and R 7 that are the same or different are selected from hydrogen, hydroxyl, amino, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 1 -C 6 alkoxy or halo C 1- C 6 alkoxy, C 1 -C 6 alkylamino, halogenated C 1 -C 6 alkylamino;
  • R 6 , R 7 can also be connected to the N to form a three-membered, four-membered, five-membered, six-membered, seven-membered or eight-membered heterocycloalkane containing C, N, O or S;
  • the triazole derivative is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
  • R 1 is selected from pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, oxazolyl, isoxazole containing C, N, O or S substituted by 1-5 R 8 Heteroaryl groups such as thiazolyl, thiazolyl, isothiazolyl, oxadiazolyl or thiadiazolyl;
  • R 2 is selected from H, halogen, C 1 -C 3 alkyl, halo C 1 -C 3 alkyl, C 3 -C 4 cycloalkyl;
  • R 3 is selected from H, C 1 -C 4 alkyl
  • R 4 and R 5 are the same or different and are selected from H, halogen, C 1 -C 3 alkyl;
  • R 6 and R 7 that are the same or different are selected from hydrogen and C 1 -C 3 alkyl groups
  • R 6 , R 7 can also be connected to the N to form a three-membered, four-membered, five-membered or six-membered heterocycloalkane containing C, N, O or S;
  • the triazole derivative is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
  • R 1 is selected from unsubstituted or substituted by 1-5 R 8 pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1, 2, 4-oxadiazole, 1,3,4-oxadiazole, 1,2,4-thiadiazole or 1,3,4-thiadiazole;
  • R 2 is selected from H, C 1 -C 3 alkyl
  • R 3 is selected from H, C 1 -C 4 alkyl
  • R 4 and R 5 are the same or different and are selected from H, halogen, C 1 -C 3 alkyl;
  • R 6 and R 7 that are the same or different are selected from hydrogen and C 1 -C 3 alkyl groups
  • R 6 , R 7 can also be connected to the N to form a three-membered, four-membered, five-membered or six-membered heterocycloalkane containing C, N, O or S;
  • the triazole derivative is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
  • R 1 is selected unsubstituted or substituted with 1-5 R 8 5-pyridyl, 2-pyridyl, 5-pyrimidinyl, 2-pyrimidinyl, 2-pyrazinyl, 2-pyridazinyl, 5- Oxazolyl, 4-oxazolyl, 5-isoxazolyl, 3-isoxazolyl, 5-thiazolyl, 4-thiazolyl, 5-isothiazolyl, 3-isothiazolyl, 3-1, 2,4-oxadiazole, 5-1,2,4-oxadiazole, 5-1,3,4-oxadiazole, 3-1,2,4-thiadiazole, 5-1,2, 4-thiadiazole or 5-1,3,4-thiadiazole;
  • R 2 is selected from H, methyl
  • R 3 is selected from tert-butyl
  • R 4 and R 5 are the same or different and are selected from H and methyl;
  • R 8 is selected from H, halogen, nitro, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy, dimethylamino, methylcarbonyl, methoxycarbonyl, methylcarbonyloxy , Trifluoromethylcarbonyloxy, methylsulfonyloxy, methoxyethoxy or ethoxyethoxy.
  • the triazole derivative is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
  • R 1 is selected from 2-R 8 -5-pyridyl, 5-R 8 -2-pyridyl, 2-R 8 -5-pyrimidinyl, 5-R 8 -2-pyrimidinyl, 2-R 8 -5 -Pyrazinyl, 2-R 8 -6-pyridazinyl, 2-R 8 -5-oxazolyl, 2-R 8 -4-oxazolyl, 3-R 8 -5-isoxazolyl, 5-R 8 -3-isothiazolyl, 2-R 8 -5-thiazolyl, 2-R 8 -4-thiazolyl, 3-R 8 -5-isothiazolyl, 5-R 8 -3- Isothiazolyl, 5-R 8 -3-1,2,4-oxadiazole, 3-R 8 -5-1,2,4-oxadiazole, 2-R 8 -5-1,3,4 -Oxadiazole, 5-R 8 -3-1,2,4-thiadiazole, 3-R 8 -5-1,2,4-
  • R 2 is selected from H
  • R 3 is selected from tert-butyl
  • R 4 and R 5 are selected from H;
  • R 8 is selected from halogen and methoxy.
  • the triazole derivative is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
  • R 1 is selected from 2-R 8 -5-pyridyl, 5-R 8 -2-pyridyl, 2-R 8 -5-pyrimidinyl, 2-R 8 -5-pyrazinyl, 2-R 8- 6-pyridazinyl or 2-R 8 -5-thiazolyl;
  • R 2 is selected from H
  • R 3 is selected from tert-butyl
  • R 4 and R 5 are selected from H;
  • R 8 is selected from chlorine, bromine and methoxy.
  • the triazole derivative is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
  • R 1 is selected from 2-R 8 -5-pyridyl
  • R 2 is selected from H
  • R 3 is selected from tert-butyl
  • R 4 and R 5 are selected from H;
  • R 8 is selected from chlorine, bromine and methoxy.
  • One of the triazole derivatives is used in the preparation of plant growth regulators or fungicides.
  • the triazole derivative as an active component in the preparation of plant growth regulators or fungicides; the weight percentage of the active component is 0.1-99%.
  • the use of the derivative of the present invention is as a plant growth control and fungicide.
  • a kind of triazole derivative represented by formula I as a salt can be hydrochloride, sulfate, hydrobromide, methanesulfonate, citrate, oxalate, succinate, maleate Acid salt, citrate, acetate, lactate, phosphate, hydroiodide, nitrate, tartrate, p-toluenesulfonate, etc.
  • Halogen refers to fluorine, chlorine, bromine or iodine.
  • Alkyl straight or branched chain alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl.
  • Cycloalkyl A substituted or unsubstituted heteroatom-containing cyclic alkyl group, such as cyclopropyl, cyclopentyl or cyclohexyl. Substituents such as methyl, halogen and the like.
  • Heterocycloalkyl substituted or unsubstituted cyclic alkyl containing one or more N, O, S heteroatoms, such as tetrahydrofuranyl, cyclopentapiperidinyl. Substituents such as methyl, halogen and the like.
  • Halogenated alkyl groups straight or branched chain alkyl groups.
  • the hydrogen atoms on these alkyl groups can be partially or fully replaced by halogen atoms, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, dichloromethane, Fluoromethyl, trifluoromethyl, etc.
  • Alkoxy straight or branched chain alkyl, connected to the structure via an oxygen atom bond.
  • Halogenated alkoxy groups straight-chain or branched-chain alkoxy groups.
  • the hydrogen atoms on these alkoxy groups may be partially or completely replaced by halogen atoms.
  • halogen atoms for example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy and the like.
  • Alkoxyalkyl The alkoxy group is attached to the structure via the alkyl group. Such as -CH 2 OCH 3 , -CH 2 OCH 2 CH 3 .
  • Halogenated alkoxyalkyl The hydrogen atoms on the alkyl group of the alkoxyalkyl group may be partially or completely replaced by halogen atoms. Such as -CH 2 OCH 2 CH 2 Cl.
  • Alkylthio straight or branched chain alkyl, connected to the structure via a sulfur atom bond.
  • Halogenated alkylthio linear or branched alkylthio.
  • the hydrogen atoms on these alkyl groups may be partially or completely replaced by halogen atoms.
  • halogen atoms for example, chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio and the like.
  • Alkenyl straight or branched chain alkenes, such as vinyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers. Alkenyl also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl.
  • Alkynyl linear or branched alkynes, such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers.
  • Alkynyl groups also include groups composed of multiple triple bonds, such as 2,5-hexadiynyl.
  • Alkenyloxy straight or branched chain alkenes, connected to the structure via an oxygen atom bond.
  • Halogenated alkenyloxy groups straight or branched chain alkenyloxy groups.
  • the hydrogen atoms on these alkenyloxy groups may be partially or completely replaced by halogen atoms.
  • Alkynoxy straight-chain or branched alkynes, connected to the structure via an oxygen atom bond.
  • Halogenated alkynyloxy groups straight or branched chain alkynyloxy groups.
  • the hydrogen atoms on these alkynyloxy groups may be partially or completely replaced by halogen atoms.
  • Alkylcarbonyl A straight or branched chain alkyl group is connected to the structure via a carbonyl group (-CO-), such as an acetyl group.
  • Halogenated alkylcarbonyl straight or branched chain alkylcarbonyl, the hydrogen atoms on the alkyl group can be partially or completely replaced by halogen atoms, such as trifluoroacetyl.
  • Alkoxycarbonyl The alkoxy is attached to the structure via the carbonyl group. Such as -COOCH 3 , -COOCH 2 CH 3 .
  • Halogenated alkoxycarbonyl The hydrogen atoms on the alkyl group of the alkoxycarbonyl group can be partially or completely replaced by halogen atoms, such as -COOCH 2 CF 3 , -COOCH 2 CH 2 Cl and so on.
  • Alkylsulfonyl straight or branched chain alkyl is connected to the structure via sulfonyl (-SO 2 -), such as methylsulfonyl.
  • Halogenated alkylsulfonyl linear or branched alkylsulfonyl, the hydrogen atoms on the alkyl group can be partially or completely replaced by halogen atoms.
  • Alkylsulfonyloxy alkyl-SO 2 -O-.
  • Halogenated alkylsulfonyloxy group The hydrogen atoms on the alkyl group of the alkylsulfonyloxy group may be partially or completely replaced by halogen atoms, such as CF 3 -SO 2 -O.
  • Alkoxycarbonylalkyl alkoxycarbonyl-alkyl-, for example CH 3 OCOCH 2 -.
  • Halogenated alkoxycarbonylalkyl The hydrogen atoms on the alkyl group of the alkoxycarbonylalkyl group may be partially or completely replaced by halogen atoms, such as CF 3 CH 2 OCOCH 2 -.
  • Alkylcarbonyloxy such as CH 3 COO- etc.
  • Halogenated alkylcarbonyloxy group The hydrogen atoms of the alkylcarbonyloxy group can be partially or completely replaced by halogen atoms, such as CF 3 COO- and so on.
  • Alkoxycarbonyloxy alkoxycarbonyl- oxy-, for example CH 3 OCOO-.
  • Halogenated alkoxycarbonyloxy The hydrogen atoms on the alkyl group of the alkoxycarbonyloxy group may be partially or completely replaced by halogen atoms, such as CF 3 OCOO-.
  • Alkylthiocarbonylalkyl alkylthiocarbonyl-alkyl-, for example CH 3 SCOCH 2 -.
  • Halogenated alkylthiocarbonylalkyl The hydrogen atoms on the alkyl group of the alkylthiocarbonylalkyl group may be partially or completely replaced by halogen atoms, such as CF 3 CH 2 SCOCH 2 -.
  • Alkoxyalkoxy such as CH 3 OCH 2 O- and the like.
  • Halogenated alkoxy alkoxy The hydrogen atoms on the alkoxy group can be partially or completely replaced by halogen atoms, such as CF 3 OCH 2 O-.
  • Alkylthioalkyl alkyl-S-alkyl-, for example CH 3 SCH 2 -.
  • Halogenated alkylthioalkyl The hydrogen atoms on the alkyl group of the alkylthioalkyl group can be partially or completely replaced by halogen atoms, such as ClCH 2 CH 2 SCH 2 -, CF 3 CH 2 SCH 2 -and so on.
  • Heteroaryl is a five-membered ring or six-membered ring containing one or more N, O, S heteroatoms.
  • furyl pyrazolyl, thiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl and the like.
  • heteroaryl moiety in heteroaryl and heteroarylalkyl, heteroaryloxy and heteroarylalkoxy refers to a five-membered ring or six-membered ring containing one or more N, O, S heteroatoms Yuan ring.
  • furyl pyrazolyl, thiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzoxazolyl, indolyl and the like.
  • the compound represented by formula I and its diastereomers, chiral isomers and salts thereof can be used for plant growth control and fungicide applications.
  • the plant growth regulation function is used to improve crop characteristics, including but not limited to: emergence, crop yield, protein content, increased vigor, faster/delayed maturation, increased/delayed seed emergence speed, improved nutrient utilization Efficiency, improved nitrogen use efficiency, improved water use efficiency, improved oil content and/or quality, improved digestibility, faster/more uniform maturation, improved flavor, improved starch content, more developed root system (Improved root growth), improved adversity tolerance (eg drought, heat, salt, light, UV, moisture, cold), reduced ethylene (reduced production and/or suppression of acceptance), increased tillers, increased plant height , Larger leaves, fewer dead basal leaves, stronger tillers, greener leaf color, pigment content, photosynthetic activity, less input requirements (such as fertilizer or water), less seed requirements, more yield Tillers, earlier flowering, early grain maturity, less plant dumping (lodging), increased stem growth, increased plant vigor, increased plant density and early and better germination.
  • root system Improved root growth
  • improved plant growth and plant development better growth, more tillers, greener leaves, larger leaves, more biomass, better roots, improved plant stress tolerance, more Higher grain yield, more harvested biomass, improved harvest quality (content of fatty acids, metabolites, oil, etc.), more marketable products (e.g. improved size), improved processes (e.g. longer storage) Time limit, better extraction of the compound), improved seed quality (sown in the following season for seed production); or any other advantage familiar to those skilled in the art.
  • the derivative represented by formula I of the present invention has the functions of delaying plant growth, inhibiting stem elongation, shortening plant internodes, promoting flower bud differentiation, promoting leaf growth, improving plant resistance to stress, and increasing plant yield in plant growth regulation. It can be used to obtain traits beneficial to agricultural production, and other plant growth regulators prepared by mixing it with agriculturally acceptable auxiliary agents can have other functions of plant growth regulation.
  • the main plants include, but are not limited to, cereal crops (rice, wheat, barley, oats, corn, millet, sorghum, etc.), tuber crops (sweet potato, potato, cassava, etc.), legume crops (soybeans, broad beans, peas, mung beans, etc.) , Adzuki beans, snow peas, etc.) and fiber crops (cotton, hemp, sericulture, etc.), oil crops (peanuts, rapeseed, sesame, soybeans, sunflowers, etc.), sugar crops (beet, sugar cane, etc.), beverage crops (tea, coffee, etc.) , Cocoa, etc.), favorite crops (tobacco, etc.), medicinal crops (ginseng, fritillary, etc.), tropical crops (rubber, coconut, oil palm, sisal, etc.), melons (watermelon, melon, cantaloupe, papaya, etc.) , And fruits, sericulture, vegetables (tomatoes, pepper
  • Oomycetes diseases such as downy mildew (cucumber downy mildew, rape downy mildew, soybean downy mildew, beet downy mildew, sugarcane) Downy mildew, tobacco 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 fungus (canola white rust, cabbage white rust), damping-off (rapeseed damping-off, tobacco damping-off, tomato damping-off, pepper damping-off, eggplant damping-off, cucumber Damping-off, cotton seedling damping-off), cotton rot (pepper spongy rot, loof
  • the derivatives of the present invention can be used to prevent and treat the following major viruses, including but not limited to: tobacco mosaic virus, tobacco rattle virus, tobacco leaf curl virus, tobacco ringspot virus, tobacco etch virus, sweet potato feathery mottle virus, potato Y virus , Potato Leaf Roll Virus, Potato X Virus, Potato S Virus, Potato A Virus, Potato Spindle Tuber Virus, Sugarcane Mosaic Virus, Sugarcane Streak Mosaic Virus, Cucumber Mosaic Virus, Melon Mosaic Virus, Pumpkin Mosaic Virus, Tomato spot wilt virus, tomato infertility virus, beet curly top virus, alfalfa mosaic virus, banana bunchy top virus, banana streak virus, citrus decay virus, wheat yellow mosaic virus, wheat soil-borne mosaic virus, wheat spindle streak pattern Leaf virus, barley yellow dwarf virus, grain mosaic virus, rice dwarf virus, rice tumour dwarf virus, rice cluster dwarf virus, rice black streaked dwarf virus, rice tooth dwarf virus, rice stripe leaf blight virus, rice white leaf
  • the derivative represented by formula I of the present invention has a fungicide function, and its mixed preparation with agriculturally acceptable auxiliary agents and other medicaments can have other functions related to agricultural production.
  • the compound synthesized by the present invention and its diastereomers, chiral isomers and their salts can be used as active ingredients of plant growth regulators and fungicides. They can be used alone or in combination with other plant growth regulators and fungicides. use.
  • the heteroaryl group of R 1 is shown in Table 1 below, but it does not limit the present invention.
  • R 2 substituents are shown in Table 2 below, but do not limit the present invention.
  • R 3 substituents are shown in Table 3 below, but they do not limit the present invention.
  • R 4 and R 5 are the same or different as shown in Table 4 below, but they do not limit the present invention.
  • R 8 substituents are shown in Table 5 below, but do not limit the present invention.
  • R 2 is H
  • R 3 is C(CH 3 ) 3
  • R 4 is H
  • R 5 is H
  • R 1 is shown in Table 6 below, and the number is 6-1------6-560:
  • X is halogen, chlorine, bromine or iodine.
  • the step 1 reaction is carried out in a suitable solvent, and the suitable solvent can be selected from ethyl acetate, dichloromethane, tetrahydrofuran, acetonitrile, toluene, xylene, benzene, N,N-dimethylformamide , Dimethyl sulfoxide, etc.
  • the suitable solvent can be selected from ethyl acetate, dichloromethane, tetrahydrofuran, acetonitrile, toluene, xylene, benzene, N,N-dimethylformamide , Dimethyl sulfoxide, etc.
  • step 1 the reaction is carried out with the participation of a suitable base, which can be selected from sodium tert-butoxide, potassium tert-butoxide, sodium hydride, sodium amide, sodium hydroxide, potassium hydroxide, sodium carbonate, Potassium carbonate, triethylamine, diisopropylethylamine, etc.
  • a suitable base which can be selected from sodium tert-butoxide, potassium tert-butoxide, sodium hydride, sodium amide, sodium hydroxide, potassium hydroxide, sodium carbonate, Potassium carbonate, triethylamine, diisopropylethylamine, etc.
  • the reaction temperature can be between room temperature and the boiling point of the solvent, usually 20-150°C.
  • the reaction time is 1 hour to 12 hours, usually 1-6 hours.
  • the reaction is carried out in a suitable solvent, which can be selected from ethyl acetate, dichloromethane, tetrahydrofuran, acetonitrile, toluene, xylene, benzene, N,N-dimethylformamide , Dimethyl sulfoxide, etc.
  • a suitable solvent which can be selected from ethyl acetate, dichloromethane, tetrahydrofuran, acetonitrile, toluene, xylene, benzene, N,N-dimethylformamide , Dimethyl sulfoxide, etc.
  • the reaction can be carried out with the participation of a suitable base, which can be selected from sodium tert-butoxide, potassium tert-butoxide, sodium hydride, sodium amide, sodium hydroxide, potassium hydroxide, and sodium carbonate , Potassium carbonate, triethylamine, diisopropylethylamine, etc.
  • a suitable base which can be selected from sodium tert-butoxide, potassium tert-butoxide, sodium hydride, sodium amide, sodium hydroxide, potassium hydroxide, and sodium carbonate , Potassium carbonate, triethylamine, diisopropylethylamine, etc.
  • the reaction temperature can be between room temperature and the boiling point of the solvent, usually 20-120°C.
  • the reaction time is 1 hour to 12 hours, usually 2-8 hours.
  • the reaction is carried out in a suitable solvent, which can be selected from methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol, tert-butanol, water and the like.
  • a suitable solvent which can be selected from methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol, tert-butanol, water and the like.
  • the reaction can be carried out with the participation of a suitable reducing agent, which can be selected from sodium borohydride, potassium borohydride, and combinations of reducing agents such as hydrogen, hydrazine hydrate, and precious metals such as palladium, platinum, etc. .
  • a suitable reducing agent which can be selected from sodium borohydride, potassium borohydride, and combinations of reducing agents such as hydrogen, hydrazine hydrate, and precious metals such as palladium, platinum, etc.
  • the reaction temperature can be between zero and the boiling point of the solvent, usually 0-100°C.
  • the reaction time is 1 hour to 24 hours, usually 2-8 hours.
  • the compound of general formula I of the present invention has excellent plant growth regulating activities and fungicidal activities such as delaying plant growth, inhibiting stem elongation, shortening plant nodes, etc., and has a shorter metabolic residue time, is easier to decompose, and is more effective for subsequent crops. The impact is even smaller.
  • the compound of general formula I is expected to play a role in the field of agricultural production.
  • the compound of general formula I of the present invention has excellent activity in inhibiting crop stem elongation, dwarfing plants, and preventing lodging, and its metabolic time in the soil is shorter than that of current market drugs, reducing The possibility of phytotoxicity occurred.
  • the compound of general formula I of the present invention reduces the height of rice plants and has a smaller impact on rice yield.
  • the compound of general formula I of the present invention also has a significant function of promoting early flowering of crops. In addition, due to its rapid degradation performance, it can minimize phytotoxicity for subsequent fruit growth.
  • Fig. 1 is a standard curve of paclobutrazol provided by an embodiment of the present invention.
  • Figure 2 is a standard curve of compound 6-375 provided by an embodiment of the present invention.
  • Figure 3 is a graph showing the dynamic trend of paclobutrazol degradation in soil provided by an embodiment of the present invention.
  • Figure 4 is a graph showing the degradation dynamics of compound No. 6-375 in soil provided by an embodiment of the present invention.
  • Figure 5 is a diagram of cucumber growth and development 21 days after drug addition provided by an embodiment of the present invention.
  • the characterization data of some compounds are as follows:
  • A is an intermediate for preparing the corresponding compound.
  • the above-obtained compound is reacted with an acid in a conventional manner to obtain the corresponding salt.
  • a certain concentration of medicinal solution is mixed with the melted agar medium, and the sprouting rice seeds are spotted on the surface of the medium and cultivated for one week to measure the physiological plant height of the rice.
  • the rice variety is Jijing 83, the rice plant height is used as the inhibition index, the treatment without compound added is the blank control, and the paclobutrazol is the positive control.
  • the inhibitory rate of compound 6-55 on rice plant height was greater than 30%, and the inhibitory rate of the positive drug paclobutrazol on rice plant height was greater than 30%.
  • a certain concentration of compound 6-55 and paclobutrazol were sprayed on the soil.
  • the original adhesion amounts of compound 6-55 and paclobutrazol in the soil were 1.2 mg/kg and 1.1 mg/kg, respectively.
  • the half-life is less than 2 days, while the half-life of paclobutrazol is greater than 3 days.
  • the determination method is as follows: a high-throughput screening method is adopted, that is, the sample of the compound to be tested is dissolved in a suitable solvent (the type of solvent is acetone, methanol, DMF, etc., and is selected according to its ability to dissolve the sample) to prepare the desired concentration The liquid to be tested.
  • a suitable solvent the type of solvent is acetone, methanol, DMF, etc., and is selected according to its ability to dissolve the sample
  • the test solution to the microwells of the 96-well culture plate, and then add the rape sclerotium pathogen propagule suspension (for the preparation method, refer to the journal article: Fujian Agriculture and Forestry Science and Technology, 1997, third issue, 15 Page) is added to it, and the treated culture plate is placed in a constant temperature incubator for culture. The investigation was conducted 24 hours later.
  • the germination or growth of the pathogen propagules was visually inspected, and the antibacterial activity of the compound was evaluated according to the germination or growth of the control treatment.
  • the aqueous solution of the solvent with the same concentration of the test compound sample was used as the CK control.
  • a certain concentration of the test compound sample is mixed with the melted agar, and the rice seed of the sprouting variety Yanfeng 47 is spotted on the surface of the agar containing the test compound, and cultivated for one week to measure the physiological plant height of the rice.
  • the rice plant height was used as the inhibition index, the treatment without compound was used as the blank control, and the paclobutrazol was used as the positive control.
  • compound 6-18, compound 6-47, compound 6-55, compound 6-59, compound 6-166, compound 6-375 inhibited rice plant height by more than 30%.
  • the positive drug paclobutrazol on rice The inhibition rate of plant height is greater than 30%.
  • the experimental crop rice the variety is Yanfeng 47. Soak the rice seeds for 24 hours, and evenly spread them in the seedling tray (54cm ⁇ 27cm ⁇ 6cm). After the rice seedlings grow to three leaves, select them and transplant them into a planting box (24cm ⁇ 15cm ⁇ 15cm). Each treatment 3 boxes, each box planted 6 holes of rice, 5 plants in each hole, the soil is field soil.
  • the test agents were paclobutrazol, uniconazole, compound 6-375 and B1, and a blank control was set at the same time.
  • Each agent is set at the concentration of 10 -4 g/mL, 10 -5 g/mL, and 10 -6 g/mL, and the application rate is 133.4 g/mu, 13.34 g/mu and 1.334 g/mu per hole.
  • the amount of medicine is calculated based on the amount of medicine added and the amount of soil in the box.
  • the soil sample containing paclobutrazol is added to 25ml acetonitrile at a liquid-to-mass ratio of 5:1, and the soil sample containing compound 6-375 is extracted by The liquid-to-mass ratio is 3:1.
  • the soil is added to 15ml of acetonitrile for extraction. After vortexing for 1 min, ultrasonic extraction for 30 min, low temperature quick freezing at -20°C for 10 min, centrifugation at 10,000 rpm/min for 5 min, the supernatant was recovered and passed through a 0.22 ⁇ m organic filter membrane for testing.
  • the test crop was cucumber. Cucumber seeds were placed in an incubator at 25°C for accelerating germination. After the sprouts grew to 1cm, they were sown in planting pots (upper diameter 12cm, lower diameter 9cm, height 11.5cm). The soil was turf soil. After a true leaf grows, apply compound fertilizer (the ratio of nitrogen, phosphorus and potassium is 15-15-15). The experiment set up blank control, test agent group, and positive control group.
  • test agents were compound 6-375 and B1, and the positive control agents were paclobutrazol and uniconazole, respectively 10 -4 g/mL (each pot equivalent to 4kg/hm 2), 10 -5 g / mL ( equivalent to application rates per pot 0.4kg / hm 2), 10 -6 g / mL ( equivalent to application rates per pot 0.04kg / hm 2), according to an amount equivalent to administration and dosage Calculation of pot soil volume.
  • the blank control CK was sprayed with water. The dosage of the medicine is calculated according to the soil volume of the planting pot.
  • the compound of general formula I synthesized by the present invention and its diastereomers, chiral isomers and their salts can be used alone, or mixed with agriculturally acceptable additives and other pharmaceutical agents. Plant growth regulation, sterilization and other functions.
  • the compound of general formula I synthesized by the present invention and its diastereomers, chiral isomers and their salts can be used as active ingredients of plant growth regulators and fungicides, and can be used alone or in combination with other plant growth regulators and Fungicides are used in combination.

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Abstract

The invention belongs to the field of chemistry. Specifically, disclosed is triazole derivatives, and an application of the derivatives in plant growth regulation and fungicides. The triazole derivatives are compounds as shown in general formula I, diastereomers and chiral isomers thereof, or salts thereof. Definitions of each substituent in the formula are described in the specification. The compounds of the present invention can be used for plant growth regulation and fungicide applications.

Description

一种三唑衍生物及其应用A kind of triazole derivative and its application 技术领域Technical field
本发明属化学领域，具体的说是一种三唑衍生物，及所述衍生物在植物生长调节及杀菌剂的应用。The invention belongs to the field of chemistry, specifically a triazole derivative, and the application of the derivative in plant growth regulation and fungicides.
背景技术Background technique
多效唑是一种植物生长调节剂，具有延缓植物生长，抑制茎秆伸长，缩短节间、促进植物分蘖、增加植物抗逆性能，提高产量等效果。但其由于残留期较长(农药电子手册，土壤半衰期为0.5-1.0年)，容易对下茬作物产生药害，导致不出苗、晚出苗，出苗率低，幼苗畸形等药害。Paclobutrazol is a plant growth regulator, which has the effects of delaying plant growth, inhibiting stem elongation, shortening internodes, promoting plant tillering, increasing plant resistance to stress, and increasing yield. However, due to its long residual period (pesticide electronic manual, soil half-life is 0.5-1.0 years), it is easy to cause phytotoxicity to the next crop, resulting in no emergence, late emergence, low emergence rate, seedling deformity and other phytotoxicity.
开发代谢速度快、残留低的植物生长调节剂对农业生产具有很大的意义。The development of plant growth regulators with fast metabolism and low residues is of great significance to agricultural production.
发明内容Summary of the invention
本发明目的在于一种三唑衍生物及其应用。The purpose of the present invention is a triazole derivative and its application.
为实现上述目的，本发明采用技术方案为：In order to achieve the above-mentioned purpose, the technical solution adopted by the present invention is as follows:
一种三唑衍生物，三唑衍生物为通式I所示化合物、其非对映异构体、手性异构体或其盐：A triazole derivative, which is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
Figure PCTCN2020131020-appb-000001
Figure PCTCN2020131020-appb-000001
其中among them
R 1选自未取代或被1-5个R 8取代的含C、N、O或S的吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、噁唑基、异噁唑基、噻唑基、异噻唑基、噁二唑基或噻二唑基等杂芳基； R 1 is selected from pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, oxazolyl, isoxazole containing C, N, O or S substituted by 1-5 R 8 Heteroaryl groups such as thiazolyl, thiazolyl, isothiazolyl, oxadiazolyl or thiadiazolyl;
R 2选自H、卤素、羟基、氨基、C 1-C 12烷基、卤代C 1-C 12烷基、C 1-C 12烷氧基、卤代C 1-C 12烷氧基、C 3-C 12环烷基、NR 6R 7、C(＝O)NR 6R 7、C 1-C 12烷硫基、卤代C 1-C 12烷硫基、C 2-C 12烯基、C 2-C 12炔基、C 2-C 12烯氧基、卤代C 2-C 12烯氧基、C 2-C 12炔氧基、卤代C 2-C 12炔氧基、C 1-C 12烷基磺酰基、卤代C 1-C 12烷基磺酰基、C 1-C 12烷基羰基、卤代C 1-C 12烷基羰基、C 1-C 12烷氧基羰基、卤代C 1-C 12烷氧基羰基、C 1-C 12烷氧基C 1-C 12烷基、卤代C 1-C 12烷氧基C 1-C 12烷基、C 1-C 12烷硫基C 1-C 12烷基、卤代C 1-C 12烷硫基C 1-C 12烷基、C 1-C 12烷氧基羰基C 1-C 12烷基、卤代C 1-C 12烷氧基羰基C 1-C 12烷基、C 1-C 12烷硫基羰基C 1-C 12烷基、卤代C 1-C 12烷硫基羰基C 1-C 12烷基、C 1-C 12烷基羰基氧基、卤代C 1-C 12烷基羰基氧基、C 1-C 12烷氧基羰基氧基、卤代C 1-C 12烷氧基羰基氧基、C 1-C 12烷基磺酰基氧基、卤代C 1-C 12烷基磺酰基氧 基、C 1-C 12烷氧基C 1-C 12烷氧基或卤代C 1-C 12烷氧基C 1-C 12烷氧基； R 2 is selected from H, halogen, hydroxyl, amino, C 1 -C 12 alkyl, halogenated C 1 -C 12 alkyl, C 1 -C 12 alkoxy, halogenated C 1 -C 12 alkoxy, C 3 -C 12 cycloalkyl, NR 6 R 7 , C(=O)NR 6 R 7 , C 1 -C 12 alkylthio, halogenated C 1 -C 12 alkylthio, C 2 -C 12 alkene Group, C 2 -C 12 alkynyl, C 2 -C 12 alkenyloxy, halo C 2 -C 12 alkenyloxy, C 2 -C 12 alkynyloxy, halo C 2 -C 12 alkynyloxy, C 1 -C 12 alkylsulfonyl, halogenated C 1 -C 12 alkylsulfonyl, C 1 -C 12 alkylcarbonyl, halogenated C 1 -C 12 alkylcarbonyl, C 1 -C 12 alkoxy Carbonyl, halogenated C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkoxy C 1 -C 12 alkyl, halogenated C 1 -C 12 alkoxy C 1 -C 12 alkyl, C 1 -C 12 alkylthio C 1 -C 12 alkyl, halogenated C 1 -C 12 alkylthio C 1 -C 12 alkyl, C 1 -C 12 alkoxycarbonyl C 1 -C 12 alkyl, halogen Substituted C 1 -C 12 alkoxycarbonyl C 1 -C 12 alkyl, C 1 -C 12 alkylthiocarbonyl C 1 -C 12 alkyl, halogenated C 1 -C 12 alkylthiocarbonyl C 1 -C 12 alkyl, C 1 -C 12 alkylcarbonyloxy, halogenated C 1 -C 12 alkylcarbonyloxy, C 1 -C 12 alkoxycarbonyloxy, halogenated C 1 -C 12 alkoxy Carbonyloxy, C 1 -C 12 alkylsulfonyloxy, halogenated C 1 -C 12 alkylsulfonyloxy, C 1 -C 12 alkoxy C 1 -C 12 alkoxy or halogenated C 1 -C 12 alkoxy C 1 -C 12 alkoxy;
R 3选自H、C 1-C 12烷基、卤代C 1-C 12烷基、C 1-C 12烷氧基、卤代C 1-C 12烷氧基、C 3-C 12环烷基、C(＝O)NR 6R 7、C 1-C 12烷硫基、卤代C 1-C 12烷硫基、C 2-C 12烯基、C 2-C 12炔基、C 2-C 12烯氧基、卤代C 2-C 12烯氧基、C 2-C 12炔氧基、卤代C 2-C 12炔氧基、C 1-C 12烷基磺酰基、卤代C 1-C 12烷基磺酰基、C 1-C 12烷基羰基、卤代C 1-C 12烷基羰基、C 1-C 12烷氧基羰基、卤代C 1-C 12烷氧基羰基、C 1-C 12烷氧基C 1-C 12烷基、卤代C 1-C 12烷氧基C 1-C 12烷基、C 1-C 12烷硫基C 1-C 12烷基、卤代C 1-C 12烷硫基C 1-C 12烷基、C 1-C 12烷氧基羰基C 1-C 12烷基、卤代C 1-C 12烷氧基羰基C 1-C 12烷基、C 1-C 12烷硫基羰基C 1-C 12烷基、卤代C 1-C 12烷硫基羰基C 1-C 12烷基、C 1-C 12烷基羰基氧基、卤代C 1-C 12烷基羰基氧基、C 1-C 12烷氧基羰基氧基、卤代C 1-C 12烷氧基羰基氧基、C 1-C 12烷基磺酰基氧基、卤代C 1-C 12烷基磺酰基氧基、C 1-C 12烷氧基C 1-C 12烷氧基或卤代C 1-C 12烷氧基C 1-C 12烷氧基； R 3 is selected from H, C 1 -C 12 alkyl, halogenated C 1 -C 12 alkyl, C 1 -C 12 alkoxy, halogenated C 1 -C 12 alkoxy, C 3 -C 12 ring Alkyl, C(=O)NR 6 R 7 , C 1 -C 12 alkylthio, halogenated C 1 -C 12 alkylthio, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, C 2- C 12 alkenyloxy, halogenated C 2 -C 12 alkenyloxy, C 2 -C 12 alkynyloxy, halogenated C 2 -C 12 alkynyloxy, C 1 -C 12 alkylsulfonyl, halogen C 1 -C 12 alkylsulfonyl, C 1 -C 12 alkylcarbonyl, halogenated C 1 -C 12 alkylcarbonyl, C 1 -C 12 alkoxycarbonyl, halogenated C 1 -C 12 alkoxy Alkyl carbonyl, C 1 -C 12 alkoxy C 1 -C 12 alkyl, halogenated C 1 -C 12 alkoxy C 1 -C 12 alkyl, C 1 -C 12 alkylthio C 1 -C 12 Alkyl, halogenated C 1 -C 12 alkylthio C 1 -C 12 alkyl, C 1 -C 12 alkoxycarbonyl C 1 -C 12 alkyl, halogenated C 1 -C 12 alkoxycarbonyl C 1 -C 12 alkyl, C 1 -C 12 alkylthiocarbonyl C 1 -C 12 alkyl, halogenated C 1 -C 12 alkylthiocarbonyl C 1 -C 12 alkyl, C 1 -C 12 alkyl Carbonyloxy, halogenated C 1 -C 12 alkylcarbonyloxy, C 1 -C 12 alkoxycarbonyloxy, halogenated C 1 -C 12 alkoxycarbonyloxy, C 1 -C 12 alkyl Sulfonyloxy, halogenated C 1 -C 12 alkylsulfonyloxy, C 1 -C 12 alkoxy C 1 -C 12 alkoxy or halogenated C 1 -C 12 alkoxy C 1 -C 12 alkoxy;
R 4与R 5相同或不同选自H、卤素、羟基、氨基、硝基、氰基、C 1-C 12烷基、卤代C 1-C 12烷基、C 1-C 12烷氧基、卤代C 1-C 12烷氧基、C 3-C 12环烷基、NR 6R 7、C(＝O)NR 6R 7、C 1-C 12烷硫基、卤代C 1-C 12烷硫基、C 2-C 12烯基、C 2-C 12炔基、C 2-C 12烯氧基、卤代C 2-C 12烯氧基、C 2-C 12炔氧基、卤代C 2-C 12炔氧基、C 1-C 12烷基磺酰基、卤代C 1-C 12烷基磺酰基、C 1-C 12烷基羰基、卤代C 1-C 12烷基羰基、C 1-C 12烷氧基羰基、卤代C 1-C 12烷氧基羰基、C 1-C 12烷氧基C 1-C 12烷基、卤代C 1-C 12烷氧基C 1-C 12烷基、C 1-C 12烷硫基C 1-C 12烷基、卤代C 1-C 12烷硫基C 1-C 12烷基、C 1-C 12烷氧基羰基C 1-C 12烷基、卤代C 1-C 12烷氧基羰基C 1-C 12烷基、C 1-C 12烷硫基羰基C 1-C 12烷基、卤代C 1-C 12烷硫基羰基C 1-C 12烷基、C 1-C 12烷基羰基氧基、卤代C 1-C 12烷基羰基氧基、C 1-C 12烷氧基羰基氧基、卤代C 1-C 12烷氧基羰基氧基、C 1-C 12烷基磺酰基氧基、卤代C 1-C 12烷基磺酰基氧基、C 1-C 12烷氧基C 1-C 12烷氧基或卤代C 1-C 12烷氧基C 1-C 12烷氧基； R 4 and R 5 are the same or different selected from H, halogen, hydroxy, amino, nitro, cyano, C 1 -C 12 alkyl, halogenated C 1 -C 12 alkyl, C 1 -C 12 alkoxy , Halogenated C 1 -C 12 alkoxy, C 3 -C 12 cycloalkyl, NR 6 R 7 , C(=O)NR 6 R 7 , C 1 -C 12 alkylthio, halogenated C 1- C 12 alkylthio, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, C 2 -C 12 alkenyloxy, halogenated C 2 -C 12 alkenyloxy, C 2 -C 12 alkynyloxy , Halogenated C 2 -C 12 alkynyloxy, C 1 -C 12 alkylsulfonyl, halogenated C 1 -C 12 alkylsulfonyl, C 1 -C 12 alkylcarbonyl, halogenated C 1 -C 12 Alkylcarbonyl, C 1 -C 12 alkoxycarbonyl, halogenated C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkoxy C 1 -C 12 alkyl, halogenated C 1 -C 12 alkane Oxygen C 1 -C 12 alkyl, C 1 -C 12 alkylthio C 1 -C 12 alkyl, halogenated C 1 -C 12 alkylthio C 1 -C 12 alkyl, C 1 -C 12 alkyl Oxycarbonyl C 1 -C 12 alkyl, halogenated C 1 -C 12 alkoxycarbonyl C 1 -C 12 alkyl, C 1 -C 12 alkylthiocarbonyl C 1 -C 12 alkyl, halogenated C 1 -C 12 alkylthiocarbonyl C 1 -C 12 alkyl, C 1 -C 12 alkylcarbonyloxy, halogenated C 1 -C 12 alkylcarbonyloxy, C 1 -C 12 alkoxycarbonyloxy Group, halogenated C 1 -C 12 alkoxycarbonyloxy, C 1 -C 12 alkylsulfonyloxy, halogenated C 1 -C 12 alkylsulfonyloxy, C 1 -C 12 alkoxy C 1 -C 12 alkoxy or halogenated C 1 -C 12 alkoxy C 1 -C 12 alkoxy;
R 6、R 7相同或不同的分别选自氢、羟基、氨基、C 1-C 12烷基、卤代C 1-C 12烷基、C 1-C 12烷氧基或卤代C 1-C 12烷氧基，C 1-C 12烷基氨基，卤代C 1-C 12烷基氨基； R 6 and R 7 which are the same or different are selected from hydrogen, hydroxyl, amino, C 1 -C 12 alkyl, halogenated C 1 -C 12 alkyl, C 1 -C 12 alkoxy or halogenated C 1- C 12 alkoxy, C 1 -C 12 alkylamino, halogenated C 1 -C 12 alkylamino;
其中，R 6、R 7还可以与其相连的N组成含C、N、O或S的三元、四元、五元、六元、七元或八元杂环烷烃； Wherein, R 6 , R 7 can also be connected to the N to form a three-membered, four-membered, five-membered, six-membered, seven-membered or eight-membered heterocycloalkane containing C, N, O or S;
R 8选自H、卤素、羟基、氨基、硝基、氰基、C 1-C 12烷基、卤代C 1-C 12烷基、C 1-C 12烷氧基、卤代C 1-C 12烷氧基、C 3-C 12环烷基、NR 6R 7、C(＝O)NR 6R 7、C 1-C 12烷硫基、卤代C 1-C 12烷硫基、C 2-C 12烯基、C 2-C 12炔基、C 2-C 12烯氧基、卤代C 2-C 12烯氧基、C 2-C 12炔氧基、卤代C 2-C 12炔氧基、C 1-C 12烷基磺酰基、卤代C 1-C 12烷基磺酰基、C 1-C 12烷基羰 基、卤代C 1-C 12烷基羰基、C 1-C 12烷氧基羰基、卤代C 1-C 12烷氧基羰基、C 1-C 12烷氧基C 1-C 12烷基、卤代C 1-C 12烷氧基C 1-C 12烷基、C 1-C 12烷硫基C 1-C 12烷基、卤代C 1-C 12烷硫基C 1-C 12烷基、C 1-C 12烷氧基羰基C 1-C 12烷基、卤代C 1-C 12烷氧基羰基C 1-C 12烷基、C 1-C 12烷硫基羰基C 1-C 12烷基、卤代C 1-C 12烷硫基羰基C 1-C 12烷基、C 1-C 12烷基羰基氧基、卤代C 1-C 12烷基羰基氧基、C 1-C 12烷氧基羰基氧基、卤代C 1-C 12烷氧基羰基氧基、C 1-C 12烷基磺酰基氧基、卤代C 1-C 12烷基磺酰基氧基、C 1-C 12烷氧基C 1-C 12烷氧基或卤代C 1-C 12烷氧基C 1-C 12烷氧基。 R 8 is selected from H, halogen, hydroxyl, amino, nitro, cyano, C 1 -C 12 alkyl, halogenated C 1 -C 12 alkyl, C 1 -C 12 alkoxy, halogenated C 1- C 12 alkoxy, C 3 -C 12 cycloalkyl, NR 6 R 7 , C(=O)NR 6 R 7 , C 1 -C 12 alkylthio, halogenated C 1 -C 12 alkylthio, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, C 2 -C 12 alkenyloxy, halogenated C 2 -C 12 alkenyloxy, C 2 -C 12 alkynyloxy, halogenated C 2- C 12 alkynyloxy, C 1 -C 12 alkylsulfonyl, halogenated C 1 -C 12 alkylsulfonyl, C 1 -C 12 alkylcarbonyl, halogenated C 1 -C 12 alkylcarbonyl, C 1 -C 12 alkoxycarbonyl, halogenated C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkoxy C 1 -C 12 alkyl, halogenated C 1 -C 12 alkoxy C 1 -C 12 alkyl, C 1 -C 12 alkylthio C 1 -C 12 alkyl, halogenated C 1 -C 12 alkylthio C 1 -C 12 alkyl, C 1 -C 12 alkoxycarbonyl C 1- C 12 alkyl, halogenated C 1 -C 12 alkoxycarbonyl C 1 -C 12 alkyl, C 1 -C 12 alkylthiocarbonyl C 1 -C 12 alkyl, halogenated C 1 -C 12 alkylthio C 1 -C 12 alkyl, C 1 -C 12 alkylcarbonyloxy, halogenated C 1 -C 12 alkylcarbonyloxy, C 1 -C 12 alkoxycarbonyloxy, halogenated C 1 -C 12 alkoxycarbonyloxy, C 1 -C 12 alkylsulfonyloxy, halogenated C 1 -C 12 alkylsulfonyloxy, C 1 -C 12 alkoxy C 1 -C 12 alkane Oxy or halo C 1 -C 12 alkoxy C 1 -C 12 alkoxy.
进一步优选，所述三唑衍生物为通式I所示化合物、其非对映异构体、手性异构体或其盐：More preferably, the triazole derivative is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
式中Where
R 1选自未取代或被1-5个R 8取代的含C、N、O或S的吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、噁唑基、异噁唑基、噻唑基、异噻唑基、噁二唑基或噻二唑基等杂芳基； R 1 is selected from pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, oxazolyl, isoxazole containing C, N, O or S substituted by 1-5 R 8 Heteroaryl groups such as thiazolyl, thiazolyl, isothiazolyl, oxadiazolyl or thiadiazolyl;
R 2选自H、卤素、C 1-C 6烷基、卤代C 1-C 6烷基、C 3-C 6环烷基、C 2-C 6烯基、C 2-C 6炔基、C 1-C 6烷氧基C 1-C 6烷基、卤代C 1-C 6烷氧基C 1-C 6烷基、C 1-C 6烷硫基C 1-C 6烷基、卤代C 1-C 6烷硫基C 1-C 6烷基、C 1-C 6烷氧基羰基C 1-C 6烷基、卤代C 1-C 6烷氧基羰基C 1-C 6烷基、C 1-C 6烷硫基羰基C 1-C 6烷基或卤代C 1-C 6烷硫基羰基C 1-C 6烷基； R 2 is selected from H, halogen, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl , C 1 -C 6 alkoxy C 1 -C 6 alkyl, halogenated C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylthio C 1 -C 6 alkyl , Halogenated C 1 -C 6 alkylthio C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, halogenated C 1 -C 6 alkoxycarbonyl C 1- C 6 alkyl, C 1 -C 6 alkylthiocarbonyl C 1 -C 6 alkyl or halogenated C 1 -C 6 alkylthiocarbonyl C 1 -C 6 alkyl;
R 3选自H、C 1-C 6烷基、卤代C 1-C 6烷基、C 3-C 6环烷基、C 2-C 6烯基、C 2-C 6炔基、C 1-C 6烷氧基C 1-C 6烷基、卤代C 1-C 6烷氧基C 1-C 6烷基、C 1-C 6烷硫基C 1-C 6烷基、卤代C 1-C 6烷硫基C 1-C 6烷基、C 1-C 6烷氧基羰基C 1-C 6烷基、卤代C 1-C 6烷氧基羰基C 1-C 6烷基、C 1-C 6烷硫基羰基C 1-C 6烷基或卤代C 1-C 6烷硫基羰基C 1-C 6烷基； R 3 is selected from H, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl, halogenated C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylthio C 1 -C 6 alkyl, halogen C 1 -C 6 alkylthio C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, halogenated C 1 -C 6 alkoxycarbonyl C 1 -C 6 Alkyl, C 1 -C 6 alkylthiocarbonyl C 1 -C 6 alkyl or halogenated C 1 -C 6 alkylthiocarbonyl C 1 -C 6 alkyl;
R 4与R 5相同或不同选自H、卤素、羟基、氨基、硝基、氰基、C 1-C 6烷基、卤代C 1-C 6烷基、C 3-C 6环烷基、C 2-C 6烯基、C 2-C 6炔基、C 1-C 6烷氧基C 1-C 6烷基、卤代C 1-C 6烷氧基C 1-C 6烷基、C 1-C 6烷硫基C 1-C 6烷基、卤代C 1-C 6烷硫基C 1-C 6烷基、C 1-C 6烷氧基羰基C 1-C 6烷基、卤代C 1-C 6烷氧基羰基C 1-C 6烷基、C 1-C 6烷硫基羰基C 1-C 6烷基、卤代C 1-C 6烷硫基羰基C 1-C 6烷基； R 4 and R 5 are the same or different selected from H, halogen, hydroxy, amino, nitro, cyano, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl, halogenated C 1 -C 6 alkoxy C 1 -C 6 alkyl , C 1 -C 6 alkylthio C 1 -C 6 alkyl, halogenated C 1 -C 6 alkylthio C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkane Group, halogenated C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, C 1 -C 6 alkylthiocarbonyl C 1 -C 6 alkyl, halogenated C 1 -C 6 alkylthiocarbonyl C 1 -C 6 alkyl;
R 6、R 7相同或不同的分别选自氢、羟基、氨基、C 1-C 6烷基、卤代C 1-C 6烷基、C 1-C 6烷氧基或卤代C 1-C 6烷氧基，C 1-C 6烷基氨基，卤代C 1-C 6烷基氨基； R 6 and R 7 that are the same or different are selected from hydrogen, hydroxyl, amino, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 1 -C 6 alkoxy or halo C 1- C 6 alkoxy, C 1 -C 6 alkylamino, halogenated C 1 -C 6 alkylamino;
其中，R 6、R 7还可以与其相连的N组成含C、N、O或S的三元、四元、五元、六元、七元或八元杂环烷烃； Wherein, R 6 , R 7 can also be connected to the N to form a three-membered, four-membered, five-membered, six-membered, seven-membered or eight-membered heterocycloalkane containing C, N, O or S;
R 8选自H、卤素、羟基、氨基、硝基、氰基、C 1-C 6烷基、卤代C 1-C 6烷基、C 1-C 6烷氧基、卤代C 1-C 6烷氧基、C 3-C 6环烷基、NR 6R 7、C(＝O)NR 6R 7、C 1-C 6烷硫基、卤代C 1-C 6烷硫基、C 2-C 6烯基、C 2-C 6 炔基、C 2-C 6烯氧基、卤代C 2-C 6烯氧基、C 2-C 6炔氧基、卤代C 2-C 6炔氧基、C 1-C 6烷基磺酰基、卤代C 1-C 6烷基磺酰基、C 1-C 6烷基羰基、卤代C 1-C 6烷基羰基、C 1-C 6烷氧基羰基、卤代C 1-C 6烷氧基羰基、C 1-C 6烷氧基C 1-C 6烷基、卤代C 1-C 6烷氧基C 1-C 6烷基、C 1-C 6烷硫基C 1-C 6烷基、卤代C 1-C 6烷硫基C 1-C 6烷基、C 1-C 6烷基羰基氧基、卤代C 1-C 6烷基羰基氧基、C 1-C 6烷基磺酰基氧基、卤代C 1-C 6烷基磺酰基氧基、C 1-C 6烷氧基C 1-C 6烷氧基或卤代C 1-C 6烷氧基C 1-C 6烷氧基。 R 8 is selected from H, halogen, hydroxyl, amino, nitro, cyano, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo C 1- C 6 alkoxy, C 3 -C 6 cycloalkyl, NR 6 R 7 , C(=O)NR 6 R 7 , C 1 -C 6 alkylthio, halogenated C 1 -C 6 alkylthio, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 2 -C 6 alkenyloxy, halogenated C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, halogenated C 2- C 6 alkynyloxy, C 1 -C 6 alkylsulfonyl, halogenated C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylcarbonyl, halogenated C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, halogenated C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl, halogenated C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylthio, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkylthio, C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy, halogen Substituted C 1 -C 6 alkylcarbonyloxy group, C 1 -C 6 alkylsulfonyloxy group, halogenated C 1 -C 6 alkylsulfonyloxy group, C 1 -C 6 alkoxy group C 1 -C 6 Alkoxy or halo C 1 -C 6 alkoxy C 1 -C 6 alkoxy.
进一步优选，所述三唑衍生物为通式I所示化合物、其非对映异构体、手性异构体或其盐：More preferably, the triazole derivative is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
式中Where
R 1选自未取代或被1-5个R 8取代的含C、N、O或S的吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、噁唑基、异噁唑基、噻唑基、异噻唑基、噁二唑基或噻二唑基等杂芳基； R 1 is selected from pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, oxazolyl, isoxazole containing C, N, O or S substituted by 1-5 R 8 Heteroaryl groups such as thiazolyl, thiazolyl, isothiazolyl, oxadiazolyl or thiadiazolyl;
R 2选自H、卤素、C 1-C 3烷基、卤代C 1-C 3烷基、C 3-C 4环烷基； R 2 is selected from H, halogen, C 1 -C 3 alkyl, halo C 1 -C 3 alkyl, C 3 -C 4 cycloalkyl;
R 3选自H、C 1-C 4烷基； R 3 is selected from H, C 1 -C 4 alkyl;
R 4与R 5相同或不同选自H、卤素、C 1-C 3烷基； R 4 and R 5 are the same or different and are selected from H, halogen, C 1 -C 3 alkyl;
R 6、R 7相同或不同的分别选自氢、C 1-C 3烷基； R 6 and R 7 that are the same or different are selected from hydrogen and C 1 -C 3 alkyl groups;
其中，R 6、R 7还可以与其相连的N组成含C、N、O或S的三元、四元、五元或六元杂环烷烃； Among them, R 6 , R 7 can also be connected to the N to form a three-membered, four-membered, five-membered or six-membered heterocycloalkane containing C, N, O or S;
R 8选自H、卤素、羟基、氨基、硝基、氰基、C 1-C 3烷基、卤代C 1-C 3烷基、C 1-C 3烷氧基、卤代C 1-C 3烷氧基、C 3-C 4环烷基、NR 6R 7、C(＝O)NR 6R 7、C 1-C 3烷硫基、卤代C 1-C 3烷硫基、C 2-C 4烯基、C 2-C 4炔基、C 1-C 3烷基磺酰基、卤代C 1-C 3烷基磺酰基、C 1-C 3烷基羰基、卤代C 1-C 3烷基羰基、C 1-C 3烷氧基羰基、卤代C 1-C 3烷氧基羰基、C 1-C 3烷基羰基氧基、卤代C 1-C 3烷基羰基氧基、C 1-C 3烷基磺酰基氧基、卤代C 1-C 3烷基磺酰基氧基、C 1-C 3烷氧基C 1-C 3烷氧基或卤代C 1-C 3烷氧基C 1-C 3烷氧基。 R 8 is selected from H, halogen, hydroxyl, amino, nitro, cyano, C 1 -C 3 alkyl, halo C 1 -C 3 alkyl, C 1 -C 3 alkoxy, halo C 1- C 3 alkoxy, C 3 -C 4 cycloalkyl, NR 6 R 7 , C(=O)NR 6 R 7 , C 1 -C 3 alkylthio, halogenated C 1 -C 3 alkylthio, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkylsulfonyl, halogenated C 1 -C 3 alkylsulfonyl, C 1 -C 3 alkylcarbonyl, halogenated C 1 -C 3 alkylcarbonyl, C 1 -C 3 alkoxycarbonyl, halogenated C 1 -C 3 alkoxycarbonyl, C 1 -C 3 alkylcarbonyloxy, halogenated C 1 -C 3 alkyl Carbonyloxy, C 1 -C 3 alkylsulfonyloxy, halogenated C 1 -C 3 alkylsulfonyloxy, C 1 -C 3 alkoxy C 1 -C 3 alkoxy or halogenated C 1 -C 3 alkoxy C 1 -C 3 alkoxy.
进一步优选，所述三唑衍生物为通式I所示化合物、其非对映异构体、手性异构体或其盐：More preferably, the triazole derivative is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
式中Where
R 1选自未取代或被1-5个R 8取代的吡啶基、嘧啶基、吡嗪基、哒嗪基、噁唑基、异噁唑基、噻唑基、异噻唑基、1,2,4-噁二唑、1,3,4-噁二唑、1,2,4-噻二唑或1,3,4-噻二唑； R 1 is selected from unsubstituted or substituted by 1-5 R 8 pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1, 2, 4-oxadiazole, 1,3,4-oxadiazole, 1,2,4-thiadiazole or 1,3,4-thiadiazole;
R 2选自H、C 1-C 3烷基； R 2 is selected from H, C 1 -C 3 alkyl;
R 3选自H、C 1-C 4烷基； R 3 is selected from H, C 1 -C 4 alkyl;
R 4与R 5相同或不同选自H、卤素、C 1-C 3烷基； R 4 and R 5 are the same or different and are selected from H, halogen, C 1 -C 3 alkyl;
R 6、R 7相同或不同的分别选自氢、C 1-C 3烷基； R 6 and R 7 that are the same or different are selected from hydrogen and C 1 -C 3 alkyl groups;
其中，R 6、R 7还可以与其相连的N组成含C、N、O或S的三元、 四元、五元或六元杂环烷烃； Wherein, R 6 , R 7 can also be connected to the N to form a three-membered, four-membered, five-membered or six-membered heterocycloalkane containing C, N, O or S;
R 8选自H、卤素、羟基、氨基、硝基、氰基、C 1-C 3烷基、卤代C 1-C 3烷基、C 1-C 3烷氧基、卤代C 1-C 3烷氧基、C 3-C 4环烷基、NR 6R 7、C(＝O)NR 6R 7、C 1-C 3烷基羰基、C 1-C 3烷氧基羰基、卤代C 1-C 3烷氧基羰基、C 1-C 3烷基羰基氧基、卤代C 1-C 3烷基羰基氧基、C 1-C 3烷基磺酰基氧基、卤代C 1-C 3烷基磺酰基氧基、C 1-C 3烷氧基C 1-C 3烷氧基或卤代C 1-C 3烷氧基C 1-C 3烷氧基。 R 8 is selected from H, halogen, hydroxyl, amino, nitro, cyano, C 1 -C 3 alkyl, halo C 1 -C 3 alkyl, C 1 -C 3 alkoxy, halo C 1- C 3 alkoxy, C 3 -C 4 cycloalkyl, NR 6 R 7 , C(=O)NR 6 R 7 , C 1 -C 3 alkylcarbonyl, C 1 -C 3 alkoxycarbonyl, halogen Substituted C 1 -C 3 alkoxycarbonyl group, C 1 -C 3 alkylcarbonyloxy group, halogenated C 1 -C 3 alkylcarbonyloxy group, C 1 -C 3 alkylsulfonyloxy group, halogenated C 1 -C 3 alkylsulfonyloxy, C 1 -C 3 alkoxy C 1 -C 3 alkoxy or halogenated C 1 -C 3 alkoxy C 1 -C 3 alkoxy.
进一步优选，所述三唑衍生物为通式I所示化合物、其非对映异构体、手性异构体或其盐：More preferably, the triazole derivative is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
式中Where
R 1选自未取代或被1-5个R 8取代的5-吡啶基、2-吡啶基、5-嘧啶基、2-嘧啶基、2-吡嗪基、2-哒嗪基、5-噁唑基、4-噁唑基、5-异噁唑基、3-异噁唑基、5-噻唑基、4-噻唑基、5-异噻唑基、3-异噻唑基、3-1,2,4-噁二唑、5-1,2,4-噁二唑、5-1,3,4-噁二唑、3-1,2,4-噻二唑、5-1,2,4-噻二唑或5-1,3,4-噻二唑； R 1 is selected unsubstituted or substituted with 1-5 R 8 5-pyridyl, 2-pyridyl, 5-pyrimidinyl, 2-pyrimidinyl, 2-pyrazinyl, 2-pyridazinyl, 5- Oxazolyl, 4-oxazolyl, 5-isoxazolyl, 3-isoxazolyl, 5-thiazolyl, 4-thiazolyl, 5-isothiazolyl, 3-isothiazolyl, 3-1, 2,4-oxadiazole, 5-1,2,4-oxadiazole, 5-1,3,4-oxadiazole, 3-1,2,4-thiadiazole, 5-1,2, 4-thiadiazole or 5-1,3,4-thiadiazole;
R 2选自H、甲基； R 2 is selected from H, methyl;
R 3选自叔丁基； R 3 is selected from tert-butyl;
R 4与R 5相同或不同选自H、甲基； R 4 and R 5 are the same or different and are selected from H and methyl;
R 8选自H、卤素、硝基、氰基、甲基、三氟甲基、甲氧基、三氟甲氧基、二甲氨基、甲基羰基、甲氧基羰基、甲基羰基氧基、三氟甲基羰基氧基、甲基磺酰基氧基、甲氧基乙氧基或乙氧基乙氧基。 R 8 is selected from H, halogen, nitro, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy, dimethylamino, methylcarbonyl, methoxycarbonyl, methylcarbonyloxy , Trifluoromethylcarbonyloxy, methylsulfonyloxy, methoxyethoxy or ethoxyethoxy.
进一步优选，三唑衍生物为通式I所示化合物、其非对映异构体、手性异构体或其盐：More preferably, the triazole derivative is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
R 1选自2-R 8-5-吡啶基、5-R 8-2-吡啶基、2-R 8-5-嘧啶基、5-R 8-2-嘧啶基、2-R 8-5-吡嗪基、2-R 8-6-哒嗪基、2-R 8-5-噁唑基、2-R 8-4-噁唑基、3-R 8-5-异噁唑基、5-R 8-3-异噁唑基、2-R 8-5-噻唑基、2-R 8-4-噻唑基、3-R 8-5-异噻唑基、5-R 8-3-异噻唑基、5-R 8-3-1,2,4-噁二唑、3-R 8-5-1,2,4-噁二唑、2-R 8-5-1,3,4-噁二唑、5-R 8-3-1,2,4-噻二唑、3-R 8-5-1,2,4-噻二唑或2-R 8-5-1,3,4-噻二唑； R 1 is selected from 2-R 8 -5-pyridyl, 5-R 8 -2-pyridyl, 2-R 8 -5-pyrimidinyl, 5-R 8 -2-pyrimidinyl, 2-R 8 -5 -Pyrazinyl, 2-R 8 -6-pyridazinyl, 2-R 8 -5-oxazolyl, 2-R 8 -4-oxazolyl, 3-R 8 -5-isoxazolyl, 5-R 8 -3-isothiazolyl, 2-R 8 -5-thiazolyl, 2-R 8 -4-thiazolyl, 3-R 8 -5-isothiazolyl, 5-R 8 -3- Isothiazolyl, 5-R 8 -3-1,2,4-oxadiazole, 3-R 8 -5-1,2,4-oxadiazole, 2-R 8 -5-1,3,4 -Oxadiazole, 5-R 8 -3-1,2,4-thiadiazole, 3-R 8 -5-1,2,4-thiadiazole or 2-R 8 -5-1,3, 4-thiadiazole;
R 2选自H； R 2 is selected from H;
R 3选自叔丁基； R 3 is selected from tert-butyl;
R 4与R 5选自H； R 4 and R 5 are selected from H;
R 8选自卤素、甲氧基。 R 8 is selected from halogen and methoxy.
进一步优选，三唑衍生物为通式I所示化合物、其非对映异构体、手性异构体或其盐：More preferably, the triazole derivative is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
式中，Where
R 1选自2-R 8-5-吡啶基、5-R 8-2-吡啶基、2-R 8-5-嘧啶基、2-R 8-5-吡嗪基、2-R 8-6-哒嗪基或2-R 8-5-噻唑基； R 1 is selected from 2-R 8 -5-pyridyl, 5-R 8 -2-pyridyl, 2-R 8 -5-pyrimidinyl, 2-R 8 -5-pyrazinyl, 2-R 8- 6-pyridazinyl or 2-R 8 -5-thiazolyl;
R 2选自H； R 2 is selected from H;
R 3选自叔丁基； R 3 is selected from tert-butyl;
R 4与R 5选自H； R 4 and R 5 are selected from H;
R 8选自氯、溴、甲氧基。 R 8 is selected from chlorine, bromine and methoxy.
更进一步优选，所述三唑衍生物为通式I所示化合物、其非对映异构体、手性异构体或其盐：More preferably, the triazole derivative is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
式中，Where
R 1选自2-R 8-5-吡啶基； R 1 is selected from 2-R 8 -5-pyridyl;
R 2选自H； R 2 is selected from H;
R 3选自叔丁基； R 3 is selected from tert-butyl;
R 4与R 5选自H； R 4 and R 5 are selected from H;
R 8选自氯、溴、甲氧基。 R 8 is selected from chlorine, bromine and methoxy.
一种所述的三唑衍生物在用于制备植物生长调节剂或杀菌剂。One of the triazole derivatives is used in the preparation of plant growth regulators or fungicides.
以所述三唑衍生物作为活性组分在用于制备植物生长调节剂或杀菌剂中的应用；所述活性组分的重量百分含量为0.1-99％。The use of the triazole derivative as an active component in the preparation of plant growth regulators or fungicides; the weight percentage of the active component is 0.1-99%.
本发明内容中，本发明衍生物的用途是作为植物生长调控与杀菌剂。In the content of the present invention, the use of the derivative of the present invention is as a plant growth control and fungicide.
一种所述的式I所示三唑衍生物成盐可为盐酸盐、硫酸盐、氢溴酸盐、甲磺酸盐、枸橼酸盐、草酸盐、丁二酸盐、马来酸盐、柠檬酸盐、乙酸盐、乳酸盐、磷酸盐、氢碘酸盐、硝酸盐、酒石酸盐、对甲苯磺酸盐等。A kind of triazole derivative represented by formula I as a salt can be hydrochloride, sulfate, hydrobromide, methanesulfonate, citrate, oxalate, succinate, maleate Acid salt, citrate, acetate, lactate, phosphate, hydroiodide, nitrate, tartrate, p-toluenesulfonate, etc.
上面给出的通式I化合物的定义中，汇集所用术语一般定义如下：In the definitions of compounds of general formula I given above, the terms used in pooling are generally defined as follows:
卤素：指氟、氯、溴或碘。Halogen: refers to fluorine, chlorine, bromine or iodine.
烷基：直链或支链烷基，例如甲基、乙基、丙基、异丙基、正丁基或叔丁基。Alkyl: straight or branched chain alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl.
环烷基：取代或未取代的含杂原子的环状烷基，例如环丙基、环戊基或环己基。取代基如甲基、卤素等。Cycloalkyl: A substituted or unsubstituted heteroatom-containing cyclic alkyl group, such as cyclopropyl, cyclopentyl or cyclohexyl. Substituents such as methyl, halogen and the like.
杂环烷基：取代或未取代的含有1个或多个N、O、S杂原子的环状烷基，例如四氢呋喃基、环戊哌啶基。取代基如甲基、卤素等。Heterocycloalkyl: substituted or unsubstituted cyclic alkyl containing one or more N, O, S heteroatoms, such as tetrahydrofuranyl, cyclopentapiperidinyl. Substituents such as methyl, halogen and the like.
卤代烷基：直链或支链烷基，在这些烷基上的氢原子可部分或全部被卤原子所取代，例如，氯甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基等。Halogenated alkyl groups: straight or branched chain alkyl groups. The hydrogen atoms on these alkyl groups can be partially or fully replaced by halogen atoms, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, dichloromethane, Fluoromethyl, trifluoromethyl, etc.
烷氧基：直链或支链烷基，经氧原子键连接到结构上。Alkoxy: straight or branched chain alkyl, connected to the structure via an oxygen atom bond.
卤代烷氧基：直链或支链烷氧基，在这些烷氧基上的氢原子可部分或全部被卤原子所取代。例如，氯甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯氟甲氧基、三氟乙氧基等。Halogenated alkoxy groups: straight-chain or branched-chain alkoxy groups. The hydrogen atoms on these alkoxy groups may be partially or completely replaced by halogen atoms. For example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy and the like.
烷氧基烷基：烷氧基经烷基连接到结构上。如-CH 2OCH 3， -CH 2OCH 2CH 3。 Alkoxyalkyl: The alkoxy group is attached to the structure via the alkyl group. Such as -CH 2 OCH 3 , -CH 2 OCH 2 CH 3 .
卤代烷氧基烷基：烷氧基烷基的烷基上的氢原子可部分或全部被卤原子所取代。如-CH 2OCH 2CH 2Cl。 Halogenated alkoxyalkyl: The hydrogen atoms on the alkyl group of the alkoxyalkyl group may be partially or completely replaced by halogen atoms. Such as -CH 2 OCH 2 CH 2 Cl.
烷硫基：直链或支链烷基，经硫原子键连接到结构上。Alkylthio: straight or branched chain alkyl, connected to the structure via a sulfur atom bond.
卤代烷硫基：直链或支链烷硫基，在这些烷基上的氢原子可部分或全部被卤原子所取代。例如，氯甲硫基、二氯甲硫基、三氯甲硫基、氟甲硫基、二氟甲硫基、三氟甲硫基、氯氟甲硫基等。Halogenated alkylthio: linear or branched alkylthio. The hydrogen atoms on these alkyl groups may be partially or completely replaced by halogen atoms. For example, chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio and the like.
烯基：直链或支链烯类，例如乙烯基、1-丙烯基、2-丙烯基和不同的丁烯基、戊烯基和己烯基异构体。烯基还包括多烯类，如1，2-丙二烯基和2，4-己二烯基。Alkenyl: straight or branched chain alkenes, such as vinyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers. Alkenyl also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl.
炔基：直链或支链炔类，例如乙炔基、1-丙炔基、2-丙炔基和不同的丁炔基、戊炔基和己炔基异构体。炔基还包括由多个三键组成的基团，如2，5-己二炔基。Alkynyl: linear or branched alkynes, such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. Alkynyl groups also include groups composed of multiple triple bonds, such as 2,5-hexadiynyl.
烯氧基：直链或支链烯类，经氧原子键连接到结构上。Alkenyloxy: straight or branched chain alkenes, connected to the structure via an oxygen atom bond.
卤代烯氧基：直链或支链烯氧基，在这些烯氧基上的氢原子可部分或全部被卤原子所取代。Halogenated alkenyloxy groups: straight or branched chain alkenyloxy groups. The hydrogen atoms on these alkenyloxy groups may be partially or completely replaced by halogen atoms.
炔氧基：直链或支链炔类，经氧原子键连接到结构上。Alkynoxy: straight-chain or branched alkynes, connected to the structure via an oxygen atom bond.
卤代炔氧基：直链或支链炔氧基，在这些炔氧基上的氢原子可部分或全部被卤原子所取代。Halogenated alkynyloxy groups: straight or branched chain alkynyloxy groups. The hydrogen atoms on these alkynyloxy groups may be partially or completely replaced by halogen atoms.
烷基羰基：直链或支链烷基经羰基(-CO-)连接到结构上，如乙酰基。Alkylcarbonyl: A straight or branched chain alkyl group is connected to the structure via a carbonyl group (-CO-), such as an acetyl group.
卤代烷基羰基：直链或支链烷基羰基，其烷基上的氢原子可部分或全部被卤原子所取代，如三氟乙酰基。Halogenated alkylcarbonyl: straight or branched chain alkylcarbonyl, the hydrogen atoms on the alkyl group can be partially or completely replaced by halogen atoms, such as trifluoroacetyl.
烷氧基羰基：烷氧基经羰基连接到结构上。如-COOCH 3，-COOCH 2CH 3。 Alkoxycarbonyl: The alkoxy is attached to the structure via the carbonyl group. Such as -COOCH 3 , -COOCH 2 CH 3 .
卤代烷氧基羰基：烷氧基羰基的烷基上的氢原子可部分或全部被卤原子所取代，如-COOCH 2CF 3，-COOCH 2CH 2Cl等。 Halogenated alkoxycarbonyl: The hydrogen atoms on the alkyl group of the alkoxycarbonyl group can be partially or completely replaced by halogen atoms, such as -COOCH 2 CF 3 , -COOCH 2 CH 2 Cl and so on.
烷基磺酰基：直链或支链烷基经磺酰基(-SO 2-)连接到结构上，如甲基磺酰基。 Alkylsulfonyl: straight or branched chain alkyl is connected to the structure via sulfonyl (-SO 2 -), such as methylsulfonyl.
卤代烷基磺酰基：直链或支链烷基磺酰基，其烷基上的氢原子可部分或全部被卤原子所取代。Halogenated alkylsulfonyl: linear or branched alkylsulfonyl, the hydrogen atoms on the alkyl group can be partially or completely replaced by halogen atoms.
烷基磺酰基氧基：烷基-SO 2-O-。 Alkylsulfonyloxy: alkyl-SO 2 -O-.
卤代烷基磺酰基氧基：烷基磺酰基氧基的烷基上的氢原子可部分或全部被卤原子所取代，例如CF 3-SO 2-O。 Halogenated alkylsulfonyloxy group: The hydrogen atoms on the alkyl group of the alkylsulfonyloxy group may be partially or completely replaced by halogen atoms, such as CF 3 -SO 2 -O.
烷氧基羰基烷基：烷氧基羰基-烷基-，例如CH 3OCOCH 2-。 Alkoxycarbonylalkyl: alkoxycarbonyl-alkyl-, for example CH 3 OCOCH 2 -.
卤代烷氧基羰基烷基：烷氧基羰基烷基的烷基上的氢原子可部分或全部被卤原子所取代，例如CF 3CH 2OCOCH 2-。 Halogenated alkoxycarbonylalkyl: The hydrogen atoms on the alkyl group of the alkoxycarbonylalkyl group may be partially or completely replaced by halogen atoms, such as CF 3 CH 2 OCOCH 2 -.
烷基羰基氧基：如CH 3COO-等。 Alkylcarbonyloxy: such as CH 3 COO- etc.
卤代烷基羰基氧基：烷基羰基氧基的氢原子可部分或全部被卤原子所取代，如CF 3COO-等。 Halogenated alkylcarbonyloxy group: The hydrogen atoms of the alkylcarbonyloxy group can be partially or completely replaced by halogen atoms, such as CF 3 COO- and so on.
烷氧基羰基氧基：烷氧基羰基-氧基-，例如CH 3OCOO-。 Alkoxycarbonyloxy: alkoxycarbonyl- oxy-, for example CH 3 OCOO-.
卤代烷氧基羰基氧基：烷氧基羰基氧基的烷基上的氢原子可部分或全部被卤原子所取代，例如CF 3OCOO-。 Halogenated alkoxycarbonyloxy: The hydrogen atoms on the alkyl group of the alkoxycarbonyloxy group may be partially or completely replaced by halogen atoms, such as CF 3 OCOO-.
烷硫基羰基烷基：烷硫基羰基-烷基-，例如CH 3SCOCH 2-。 Alkylthiocarbonylalkyl: alkylthiocarbonyl-alkyl-, for example CH 3 SCOCH 2 -.
卤代烷硫基羰基烷基：烷硫基羰基烷基的烷基上的氢原子可部分或全部被卤原子所取代，例如CF 3CH 2SCOCH 2-。 Halogenated alkylthiocarbonylalkyl: The hydrogen atoms on the alkyl group of the alkylthiocarbonylalkyl group may be partially or completely replaced by halogen atoms, such as CF 3 CH 2 SCOCH 2 -.
烷氧基烷氧基：如CH 3OCH 2O-等。 Alkoxyalkoxy: such as CH 3 OCH 2 O- and the like.
卤代烷氧基烷氧基：烷氧基上的氢原子可部分或全部被卤原子所取代，例如CF 3OCH 2O-。 Halogenated alkoxy alkoxy: The hydrogen atoms on the alkoxy group can be partially or completely replaced by halogen atoms, such as CF 3 OCH 2 O-.
烷硫基烷基：烷基-S-烷基-，例如CH 3SCH 2-。 Alkylthioalkyl: alkyl-S-alkyl-, for example CH 3 SCH 2 -.
卤代烷硫基烷基：烷硫基烷基的烷基上的氢原子可部分或全部被卤原子所取代，如ClCH 2CH 2SCH 2-、CF 3CH 2SCH 2-等。 Halogenated alkylthioalkyl: The hydrogen atoms on the alkyl group of the alkylthioalkyl group can be partially or completely replaced by halogen atoms, such as ClCH 2 CH 2 SCH 2 -, CF 3 CH 2 SCH 2 -and so on.
杂芳基是含1个或多个N、O、S杂原子的五元环或六元环。例如呋喃基、吡唑基、噻唑基、吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、喹啉基等。Heteroaryl is a five-membered ring or six-membered ring containing one or more N, O, S heteroatoms. For example, furyl, pyrazolyl, thiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl and the like.
杂芳基以及杂芳基烷基、杂芳基氧基和杂芳基烷氧基等中的杂芳基部分是指含1个或多个N、O、S杂原子的五元环或六元环。例如呋喃基、吡唑基、噻唑基、吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、喹啉基、苯并噁唑基、吲哚基等。The heteroaryl moiety in heteroaryl and heteroarylalkyl, heteroaryloxy and heteroarylalkoxy refers to a five-membered ring or six-membered ring containing one or more N, O, S heteroatoms Yuan ring. For example, furyl, pyrazolyl, thiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzoxazolyl, indolyl and the like.
所述式I所示化合物及其非对映异构体、手性异构体及其盐可用于植物生长调控和杀菌剂的用途。The compound represented by formula I and its diastereomers, chiral isomers and salts thereof can be used for plant growth control and fungicide applications.
所述植物生长调节功能是用于改善作物特征，包括但不限于：出苗，作物产量，蛋白质含量，增加的活力，更快的/延缓的成熟，增加/延缓的种子出苗速度，改善的营养素利用效率，改善的氮利用效率，改善的用水效率，改善的油含量和/或品质，改善的可消化性，更快的/更均匀的熟化，改善的风味，改善的淀粉含量，更发达的根系(改善的根系生长)，改善的逆境忍耐(例如对干旱、炎热、盐分、光照、UV、水分、寒冷)，减少的乙烯(减少的产生和/或接受的抑制)，分蘖增加，植物高度增加，更大的叶片，更少的死亡基生叶，更强壮的分蘖，更绿叶色，色素含量，光合活性，更少的输入需求(比如肥料或水)，更少的种子需求，更多产的分蘖，更早的开花，谷物早熟，更少的植物倾倒(倒伏)，增加的茎枝生长，增强的植株活力，增加的植株密度以及早期和更佳的发芽。是例如经改善的植物生长和植物发育，更佳的生长，更多分蘖，更绿的叶片，更大的叶片，更多的生物质，更佳的根部，经改善的植物逆境耐性，更多的谷物产量，更多的收获生物质，经改善的收获品质(脂肪酸，代谢产物，油等的 含量)，更易营销的产品(例如经改善的大小)，经改善的工序(例如更长的贮藏期限，对化合物的更佳提取)，经改善的种子品质(在随后的季节播种用于种子生产)；或者本领域技术人员熟悉的任何其他优势。The plant growth regulation function is used to improve crop characteristics, including but not limited to: emergence, crop yield, protein content, increased vigor, faster/delayed maturation, increased/delayed seed emergence speed, improved nutrient utilization Efficiency, improved nitrogen use efficiency, improved water use efficiency, improved oil content and/or quality, improved digestibility, faster/more uniform maturation, improved flavor, improved starch content, more developed root system (Improved root growth), improved adversity tolerance (eg drought, heat, salt, light, UV, moisture, cold), reduced ethylene (reduced production and/or suppression of acceptance), increased tillers, increased plant height , Larger leaves, fewer dead basal leaves, stronger tillers, greener leaf color, pigment content, photosynthetic activity, less input requirements (such as fertilizer or water), less seed requirements, more yield Tillers, earlier flowering, early grain maturity, less plant dumping (lodging), increased stem growth, increased plant vigor, increased plant density and early and better germination. For example, improved plant growth and plant development, better growth, more tillers, greener leaves, larger leaves, more biomass, better roots, improved plant stress tolerance, more Higher grain yield, more harvested biomass, improved harvest quality (content of fatty acids, metabolites, oil, etc.), more marketable products (e.g. improved size), improved processes (e.g. longer storage) Time limit, better extraction of the compound), improved seed quality (sown in the following season for seed production); or any other advantage familiar to those skilled in the art.
本发明式I所示衍生物具备植物生长调节中的延缓植物生长、抑制茎杆伸长、缩短植物节间、促进花芽分化、促进叶片生长、提高植物抗逆性能、提高植物产量等功能，其可用于获得对农业生产有利的性状，其与农业上可接受的助剂混合制备的其他植物生长调节剂可具备植物生长调节的其他功能。The derivative represented by formula I of the present invention has the functions of delaying plant growth, inhibiting stem elongation, shortening plant internodes, promoting flower bud differentiation, promoting leaf growth, improving plant resistance to stress, and increasing plant yield in plant growth regulation. It can be used to obtain traits beneficial to agricultural production, and other plant growth regulators prepared by mixing it with agriculturally acceptable auxiliary agents can have other functions of plant growth regulation.
其中主要的植物包括但不限于谷类作物(水稻、小麦、大麦、燕麦、玉米、谷子、高粱等)、薯类作物(甘薯、马铃薯、木薯等)、豆类作物(大豆、蚕豆、豌豆、绿豆、小豆、荷兰豆等)和纤维作物(棉花、麻类、蚕桑等)、油料作物(花生、油菜、芝麻、大豆、向日葵等)、糖料作物(甜菜、甘蔗等)、饮料作物(茶叶、咖啡、可可等)、嗜好作物(烟草等)、药用作物(人参、贝母等)、热带作物(橡胶、椰子、油棕、剑麻等)、瓜类(西瓜、甜瓜、哈密瓜、木瓜等)、以及水果、蚕桑、蔬菜(番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、葱、蒜、各种山野菜等)、竹笋、花卉(如兰花等)、盆景及观赏植物等；还包括果树(苹果、香蕉、柑桔，桃树、番木瓜)、啤酒花、胡椒、种苗及其他园艺作物。The main plants include, but are not limited to, cereal crops (rice, wheat, barley, oats, corn, millet, sorghum, etc.), tuber crops (sweet potato, potato, cassava, etc.), legume crops (soybeans, broad beans, peas, mung beans, etc.) , Adzuki beans, snow peas, etc.) and fiber crops (cotton, hemp, sericulture, etc.), oil crops (peanuts, rapeseed, sesame, soybeans, sunflowers, etc.), sugar crops (beet, sugar cane, etc.), beverage crops (tea, coffee, etc.) , Cocoa, etc.), favorite crops (tobacco, etc.), medicinal crops (ginseng, fritillary, etc.), tropical crops (rubber, coconut, oil palm, sisal, etc.), melons (watermelon, melon, cantaloupe, papaya, etc.) , And fruits, sericulture, vegetables (tomatoes, peppers, radishes, cucumbers, cabbage, celery, mustard, shallots, garlic, various wild vegetables, etc.), bamboo shoots, flowers (such as orchids, etc.), bonsai and ornamental plants, etc.; also include Fruit trees (apples, bananas, oranges, peach trees, papaya), hops, peppers, seedlings and other horticultural crops.
本发明式I所示衍生物可用于防治下列病害，包括但不限于：卵菌纲病害，如霜霉病(黄瓜霜霉病、油菜霜霉病、大豆霜霉病、甜菜霜霉病、甘蔗霜霉病、烟草霜霉病、豌豆霜霉病、丝瓜霜霉病、冬瓜霜霉病、甜瓜霜霉病、白菜类霜霉病、菠菜霜霉病、萝卜霜霉病、葡萄霜霉病、葱霜霉病)，白锈菌(油菜白锈病、白菜类白锈病)，猝倒病(油菜猝倒病、烟草猝倒病、番茄猝倒病、辣椒猝倒病、茄子猝倒病、黄瓜猝倒病、棉苗猝倒病)，绵腐病(辣椒绵腐病、丝瓜绵腐病、冬瓜绵腐病)，疫病(蚕豆疫病、黄瓜疫病、南瓜疫病、冬瓜疫病、西瓜疫病、甜瓜疫病、辣椒疫病、韭菜疫病、大蒜疫病、棉花疫病)，晚疫病(马铃薯晚疫病、番茄晚疫病)等；半知菌病害，如枯萎病(甘薯枯萎病、棉花枯萎病、芝麻枯萎病、蓖麻枯萎病、番茄枯萎病、菜豆枯萎病、黄瓜枯萎病、丝瓜枯萎病、南瓜枯萎病、冬瓜枯萎病、西瓜枯萎病、甜瓜枯萎病、辣椒枯萎病、蚕豆枯萎病、油菜枯萎病、大豆枯萎病)，根腐病(辣椒根腐病、茄子根腐病、菜豆根腐病、黄瓜根腐病、苦瓜根腐病、棉黑根腐病、蚕豆根腐病)，立枯病(棉苗立枯病、芝麻立枯病、辣椒立枯病、黄瓜立枯病、白菜立枯病)，炭疽病(高粱炭疽病、棉花炭疽病、红麻炭疽病、黄麻炭疽病、亚麻炭疽病、烟草炭疽病、桑炭疽病、辣椒炭疽病、茄子炭疽病、菜豆炭 疽病、黄瓜炭疽病、苦瓜炭疽病、西葫芦炭疽病、冬瓜炭疽病、西瓜炭疽病、甜瓜炭疽病、荔枝炭疽病)，黄萎病(棉花黄萎病、向日葵黄萎病、番茄黄萎病、辣椒黄萎病、茄子黄萎病)，黑星病(西葫芦黑星病、冬瓜黑星病、甜瓜黑星病)，灰霉病(棉铃灰霉病、红麻灰霉病、番茄灰霉病、辣椒灰霉病、菜豆灰霉病、芹菜灰霉病、菠菜灰霉病、猕猴桃灰霉病)，褐斑病(棉花褐斑病、黄麻褐斑病、甜菜褐斑病、花生褐斑病、辣椒褐斑病、冬瓜褐斑病、大豆褐斑病、向日葵褐斑病、豌豆褐斑病、蚕豆褐斑病)，黑斑病(亚麻假黑斑病、油菜黑斑病、芝麻黑斑病、向日葵黑斑病、蓖麻黑斑病、番茄黑斑病、辣椒黑斑病、茄子黑斑病、菜豆黑斑病、黄瓜黑斑病、芹菜黑斑病、胡萝卜黑腐病、胡萝卜黑斑病、苹果黑斑病、花生黑斑病)，斑枯病(番茄斑枯病、辣椒斑枯病、芹菜斑枯病)，早疫病(番茄早疫病、辣椒早疫病、茄子早疫病、马铃薯早疫病、芹菜早疫病)，轮纹病(大豆轮纹病、芝麻轮纹病、菜豆轮纹病)，叶枯病(芝麻叶枯病、向日葵叶枯病、西瓜叶枯病、甜瓜叶枯病)，茎基腐病(番茄茎基腐病、菜豆茎基腐病)，及其他(玉米圆斑病、红麻腰折病、稻瘟病、栗黑鞘病、甘蔗眼斑病、棉铃曲霉病、花生冠腐病、大豆茎枯病、大豆黑点病、甜瓜大斑病、花生网斑病、茶赤叶斑病、辣椒白星病、冬瓜叶斑病、芹菜黑腐病、菠菜心腐病、红麻叶霉病、红麻斑点病、黄麻茎斑病、大豆紫斑病、芝麻叶斑病、蓖麻灰斑病、茶褐色叶斑病、茄子褐色圆星病、菜豆红斑病、苦瓜白斑病、西瓜斑点病、黄麻枯腐病、向日葵根茎腐病、菜豆炭腐病、大豆靶点病、茄子棒孢叶斑病、黄瓜靶斑病、番茄叶霉病、茄子叶霉病、蚕豆赤斑病等)等；担子菌病害，如锈病(小麦条锈病、小麦杆锈病、小麦叶锈病、花生锈病、向日葵锈病、甘蔗锈病、韭菜锈病、葱锈病、栗锈病、大豆锈病)，黑穗病(玉米丝黑穗病、玉米黑粉病、高粱丝黑穗病、高粱散黑穗病、高粱坚黑穗病、高梁柱黑粉病、栗粒黑穗病、甘蔗黑穗病、菜豆锈病)及其他(如小麦纹枯病、水稻纹枯病等)等；子囊菌病害，如白粉病(小麦白粉病、油菜白粉病、芝麻白粉病、向日葵白粉病、甜菜白粉病、茄子白粉病、豌豆白粉病、丝瓜白粉病、南瓜白粉病、西葫芦白粉病、冬瓜白粉病、甜瓜白粉病、葡萄白粉病、蚕豆白粉病)，菌核病(亚麻菌核病、油菜菌核病、大豆菌核病、花生菌核病、烟草菌核病、辣椒菌核病、茄子菌核病、菜豆菌核病、豌豆菌核病、黄瓜菌核病、苦瓜菌核病、冬瓜菌核病、西瓜菌核病、芹菜菌核病)，黑星病(苹果黑星病、梨黑星病)等。The derivatives of formula I of the present invention can be used to prevent and control the following diseases, including but not limited to: Oomycetes diseases, such as downy mildew (cucumber downy mildew, rape downy mildew, soybean downy mildew, beet downy mildew, sugarcane) Downy mildew, tobacco 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 fungus (canola white rust, cabbage white rust), damping-off (rapeseed damping-off, tobacco damping-off, tomato damping-off, pepper damping-off, eggplant damping-off, cucumber Damping-off, cotton seedling damping-off), cotton rot (pepper spongy rot, loofah spongy rot, wax gourd spongy rot), blight (broad bean blight, cucumber blight, pumpkin blight, wax gourd blight, watermelon blight, melon blight) , Pepper blight, leek blight, garlic blight, cotton blight), late blight (potato late blight, tomato late blight), etc.; imperfect fungal diseases, such as fusarium wilt (sweet potato blight, cotton blight, sesame blight, castor oil Fusarium wilt, tomato wilt, bean wilt, cucumber wilt, loofah wilt, pumpkin wilt, wax gourd wilt, watermelon wilt, melon wilt, pepper wilt, broad bean wilt, rapeseed wilt, soybean wilt ), root rot (pepper root rot, eggplant root rot, bean root rot, cucumber root rot, bitter gourd root rot, cotton black root rot, broad bean root rot), blast (cotton seedlings) Blight, sesame blight, pepper blight, cucumber blight, cabbage blight), anthracnose (sorghum anthracnose, cotton anthracnose, kenaf anthracnose, jute anthracnose, flax anthracnose, tobacco anthracnose Disease, mulberry anthracnose, pepper anthracnose, eggplant anthracnose, bean anthracnose, cucumber anthracnose, bitter melon anthracnose, zucchini anthracnose, wax gourd anthracnose, watermelon anthracnose, melon anthracnose, litchi anthracnose), Verticillium wilt (Cotton verticillium wilt, sunflower verticillium wilt, tomato verticillium wilt, pepper verticillium wilt, eggplant verticillium wilt), scab (summer squash scab, wax gourd scab, melon scab), gray mold (Cotton boll gray mold, kenaf gray mold, tomato gray mold, pepper gray mold, kidney bean gray mold, celery gray mold, spinach gray mold, kiwi gray mold), brown spot (cotton brown spot Disease, jute brown spot, beet brown spot, peanut brown spot, pepper brown spot, wax gourd brown spot, soybean brown spot, sunflower brown spot, pea brown spot, broad bean brown spot), black spot Diseases (flax pseudoblack spot, rape black spot, sesame black spot, sunflower black spot, castor bean black spot, tomato black spot, pepper black spot, eggplant black spot, kidney bean black spot, cucumber Black spot, celery black spot, carrot black spot, carrot black spot, apple black spot, peanut black spot), spot blight (tomato spot blight, pepper spot blight, celery spot blight), Early blight (tomato early blight, pepper early blight, eggplant early blight, potato early blight, celery early blight), ring disease (soybean ring disease, sesame ring disease, bean ring disease), leaf blight (sesame leaf Blight, sunflower leaf blight, watermelon leaf blight, melon leaf blight), stem base rot (tomato stem base rot, kidney bean stem base rot), and Others (corn round spot, kenaf waist break, rice blast, chestnut black sheath disease, sugarcane eye spot, cotton boll aspergillus, 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, kenaf spot, jute stem spot, soybean purpura, Sesame leaf spot, castor gray spot, tea-brown leaf spot, eggplant brown spot, bean red spot, bitter gourd white spot, watermelon spot, jute blight, sunflower root rot, bean charcoal rot, soybean Target spot disease, Corynespora leaf spot of eggplant, Target spot of cucumber, Tomato leaf mold, Eggplant leaf mold, Broad bean red spot, etc.); Basidiomycete diseases, such as rust (wheat stripe rust, wheat stalk rust, wheat Leaf rust, flower rust, sunflower rust, sugarcane rust, leek rust, onion rust, chestnut rust, soybean rust), smut (corn head smut, corn smut, sorghum head smut, sorghum loose smut) Disease, sorghum hard smut, sorghum column smut, chestnut smut, sugarcane smut, kidney bean rust) and others (such as wheat sheath blight, rice sheath blight, etc.); ascomycete diseases, such as Powdery mildew (wheat powdery mildew, rape powdery mildew, sesame powdery mildew, sunflower powdery mildew, beet powdery mildew, eggplant powdery mildew, pea powdery mildew, loofah powdery mildew, pumpkin powdery mildew, zucchini powdery mildew, wax gourd powdery mildew, melon powdery mildew) , Grape powdery mildew, broad bean powdery mildew), sclerotinia (flax sclerotinia, rape sclerotinia, soybean sclerotinia, peanut sclerotinia, tobacco sclerotinia, pepper sclerotinia, eggplant sclerotinia, kidney bean Sclerotinia sclerotiorum, pea sclerotinia, cucumber sclerotinia, bitter melon sclerotinia, wax gourd sclerotinia, watermelon sclerotinia, celery sclerotinia), scab (apple sclerosis, pear sclerosis), etc. .
本发明衍生物可用于防治下列主要病毒，包括但不限于：烟草花叶病毒、烟草脆裂病毒、烟草曲叶病毒、烟草环斑病毒、烟草蚀纹病毒、甘薯羽状斑驳病毒、马铃薯Y病毒、马铃薯卷叶病毒、马铃薯 X病毒、马铃薯S病毒、马铃薯A病毒、马铃薯纺锤块茎类病毒、甘蔗花叶病毒、甘蔗线条花叶病毒、黄瓜花叶病毒、甜瓜花叶病毒、南瓜花叶病毒、番茄斑萎病毒、番茄不孕病毒、甜菜曲顶病毒、苜蓿花叶病毒、香蕉束顶病毒、香蕉线条病毒、柑橘衰退病毒、小麦黄花叶病毒、小麦土传花叶病毒、小麦梭条斑花叶病毒、大麦黄矮病毒、禾谷花叶病毒、水稻矮缩病毒、水稻瘤矮病毒、水稻簇矮病毒、水稻黑条矮缩病毒、水稻齿矮病毒、水稻条纹叶枯病毒、水稻白叶病毒、水稻草状矮化病毒、水稻黄叶病毒、水稻黄化病毒、水稻东格鲁球状病毒、水稻黄斑驳病毒、水稻条纹坏死病毒、水稻东格鲁杆状病毒、水稻坏死花叶病毒等。The derivatives of the present invention can be used to prevent and treat the following major viruses, including but not limited to: tobacco mosaic virus, tobacco rattle virus, tobacco leaf curl virus, tobacco ringspot virus, tobacco etch virus, sweet potato feathery mottle virus, potato Y virus , Potato Leaf Roll Virus, Potato X Virus, Potato S Virus, Potato A Virus, Potato Spindle Tuber Virus, Sugarcane Mosaic Virus, Sugarcane Streak Mosaic Virus, Cucumber Mosaic Virus, Melon Mosaic Virus, Pumpkin Mosaic Virus, Tomato spot wilt virus, tomato infertility virus, beet curly top virus, alfalfa mosaic virus, banana bunchy top virus, banana streak virus, citrus decay virus, wheat yellow mosaic virus, wheat soil-borne mosaic virus, wheat spindle streak pattern Leaf virus, barley yellow dwarf virus, grain mosaic virus, rice dwarf virus, rice tumour dwarf virus, rice cluster dwarf virus, rice black streaked dwarf virus, rice tooth dwarf virus, rice stripe leaf blight virus, rice white leaf Viruses, rice grassy stunting virus, rice yellow leaf virus, rice yellowing virus, rice Donggelu globular virus, rice yellow mottle virus, rice stripe necrosis virus, rice Donggelu baculovirus, rice necrosis mosaic virus, etc. .
本发明式I所示衍生物具备杀菌剂功能，其与农业上可接受的助剂以及其他药剂的混合制备可具备农业生产相关的其他功能。The derivative represented by formula I of the present invention has a fungicide function, and its mixed preparation with agriculturally acceptable auxiliary agents and other medicaments can have other functions related to agricultural production.
本发明合成的化合物及其非对映异构体、手性异构体及其盐可用于植物生长调节及杀菌剂的活性成分，可以单独使用，也可以与其它植物生长调节剂和杀菌剂联合使用。The compound synthesized by the present invention and its diastereomers, chiral isomers and their salts can be used as active ingredients of plant growth regulators and fungicides. They can be used alone or in combination with other plant growth regulators and fungicides. use.
本发明式Ⅰ所示衍生物中部分取代基如表1-5所示，本发明式Ⅰ所示部分化合物由表6-162中列出的具体化合物来说明，但并不限定本发明。Part of the substituents in the derivatives of formula I of the present invention are shown in Tables 1-5, and some of the compounds of formula I of the present invention are illustrated by the specific compounds listed in Table 6-162, but do not limit the present invention.
Figure PCTCN2020131020-appb-000002
Figure PCTCN2020131020-appb-000002
R 1的杂芳基如下表1所示，但并不限定本发明。 The heteroaryl group of R 1 is shown in Table 1 below, but it does not limit the present invention.
表1：Table 1:
Figure PCTCN2020131020-appb-000003
Figure PCTCN2020131020-appb-000003
R 2取代基如下表2所示，但并不限定本发明。 The R 2 substituents are shown in Table 2 below, but do not limit the present invention.
表2：Table 2:
Figure PCTCN2020131020-appb-000004
Figure PCTCN2020131020-appb-000004
Figure PCTCN2020131020-appb-000005
Figure PCTCN2020131020-appb-000005
R 3取代基如下表3所示，但并不限定本发明。 The R 3 substituents are shown in Table 3 below, but they do not limit the present invention.
表3：table 3:
Figure PCTCN2020131020-appb-000006
Figure PCTCN2020131020-appb-000006
R 4与R 5取代基相同或不同如下表4所示，但并不限定本发明。 The substituents of R 4 and R 5 are the same or different as shown in Table 4 below, but they do not limit the present invention.
表4：Table 4:
Figure PCTCN2020131020-appb-000007
Figure PCTCN2020131020-appb-000007
R 8取代基如下表5所示，但并不限定本发明。 The R 8 substituents are shown in Table 5 below, but do not limit the present invention.
表5table 5
Figure PCTCN2020131020-appb-000008
Figure PCTCN2020131020-appb-000008
Figure PCTCN2020131020-appb-000009
Figure PCTCN2020131020-appb-000009
通式化合物由表6-表162中列出的具体化合物来说明，但并不限定本发明。The compounds of the general formula are illustrated by the specific compounds listed in Table 6 to Table 162, but do not limit the present invention.
Figure PCTCN2020131020-appb-000010
Figure PCTCN2020131020-appb-000010
R 2为H，R 3为C(CH 3) 3，R 4为H，R 5为H时，R 1如下表6，编号为6-1------6-560： When R 2 is H, R 3 is C(CH 3 ) 3 , R 4 is H, and R 5 is H, R 1 is shown in Table 6 below, and the number is 6-1------6-560:
表6Table 6
Figure PCTCN2020131020-appb-000011
Figure PCTCN2020131020-appb-000011
Figure PCTCN2020131020-appb-000012
Figure PCTCN2020131020-appb-000012
Figure PCTCN2020131020-appb-000013
Figure PCTCN2020131020-appb-000013
Figure PCTCN2020131020-appb-000014
Figure PCTCN2020131020-appb-000014
Figure PCTCN2020131020-appb-000015
Figure PCTCN2020131020-appb-000015
Figure PCTCN2020131020-appb-000016
Figure PCTCN2020131020-appb-000016
Figure PCTCN2020131020-appb-000017
Figure PCTCN2020131020-appb-000017
表7-表162中列出的具体化合物如下：The specific compounds listed in Table 7-Table 162 are as follows:
表table 化合物编号Compound number R 2 R 2 R 3 R 3 R 4 R 4 R 5 R 5 R 1 R 1
77 7-1—7-5607-1—7-560 HH 叔丁基Tert-butyl HH HH 如表6As shown in Table 6
88 8-1—8-5608-1—8-560 HH 叔丁基Tert-butyl 甲基methyl HH 如表6As shown in Table 6
99 9-1—9-5609-1—9-560 HH 叔丁基Tert-butyl HH 甲基methyl 如表6As shown in Table 6
1010 10-1—10-56010-1—10-560 HH 叔丁基Tert-butyl 甲基methyl 甲基methyl 如表6As shown in Table 6
1111 11-1—11-56011-1—11-560 HH 叔丁基Tert-butyl FF HH 如表6As shown in Table 6
1212 12-1—12-56012-1—12-560 HH 叔丁基Tert-butyl HH FF 如表6As shown in Table 6
1313 13-1—13-56013-1—13-560 HH 叔丁基Tert-butyl FF FF 如表6As shown in Table 6
1414 14-1—14-56014-1—14-560 HH 叔丁基Tert-butyl ClCl HH 如表6As shown in Table 6
1515 15-1—15-56015-1—15-560 HH 叔丁基Tert-butyl HH ClCl 如表6As shown in Table 6
1616 16-1—16-56016-1—16-560 HH 叔丁基Tert-butyl ClCl ClCl 如表6As shown in Table 6
1717 17-1—17-56017-1—17-560 HH 叔丁基Tert-butyl BrBr HH 如表6As shown in Table 6
1818 18-1—18-56018-1—18-560 HH 叔丁基Tert-butyl HH BrBr 如表6As shown in Table 6
1919 19-1—19-56019-1—19-560 HH 叔丁基Tert-butyl BrBr BrBr 如表6As shown in Table 6
2020 20-1—20-56020-1—20-560 HH 异丙基Isopropyl HH HH 如表6As shown in Table 6
21twenty one 21-1—21-56021-1-21-560 HH 异丙基Isopropyl 甲基methyl HH 如表6As shown in Table 6
22twenty two 22-1—22-56022-1—22-560 HH 异丙基Isopropyl HH 甲基methyl 如表6As shown in Table 6
23twenty three 23-1—23-56023-1—23-560 HH 异丙基Isopropyl 甲基methyl 甲基methyl 如表6As shown in Table 6
24twenty four 24-1—24-56024-1—24-560 HH 异丙基Isopropyl FF HH 如表6As shown in Table 6
2525 25-1—25-56025-1—25-560 HH 异丙基Isopropyl HH FF 如表6As shown in Table 6
2626 26-1—26-56026-1—26-560 HH 异丙基Isopropyl FF FF 如表6As shown in Table 6
2727 27-1—27-56027-1—27-560 HH 异丙基Isopropyl ClCl HH 如表6As shown in Table 6
2828 28-1—28-56028-1—28-560 HH 异丙基Isopropyl HH ClCl 如表6As shown in Table 6
2929 29-1—29-56029-1—29-560 HH 异丙基Isopropyl ClCl ClCl 如表6As shown in Table 6
3030 30-1—30-56030-1—30-560 HH 异丙基Isopropyl BrBr HH 如表6As shown in Table 6
3131 31-1—31-56031-1—31-560 HH 异丙基Isopropyl HH BrBr 如表6As shown in Table 6
3232 32-1—32-56032-1—32-560 HH 异丙基Isopropyl BrBr BrBr 如表6As shown in Table 6
3333 33-1—33-56033-1—33-560 HH 环丙基Cyclopropyl HH HH 如表6As shown in Table 6
3434 34-1—34-56034-1—34-560 HH 环丙基Cyclopropyl 甲基methyl HH 如表6As shown in Table 6
3535 35-1—35-56035-1—35-560 HH 环丙基Cyclopropyl HH 甲基methyl 如表6As shown in Table 6
3636 36-1—36-56036-1—36-560 HH 环丙基Cyclopropyl 甲基methyl 甲基methyl 如表6As shown in Table 6
3737 37-1—37-56037-1—37-560 HH 环丙基Cyclopropyl FF HH 如表6As shown in Table 6
3838 38-1—38-56038-1—38-560 HH 环丙基Cyclopropyl HH FF 如表6As shown in Table 6
3939 39-1—39-56039-1—39-560 HH 环丙基Cyclopropyl FF FF 如表6As shown in Table 6
4040 40-1—40-56040-1—40-560 HH 环丙基Cyclopropyl ClCl HH 如表6As shown in Table 6
4141 41-1—41-56041-1—41-560 HH 环丙基Cyclopropyl HH ClCl 如表6As shown in Table 6
4242 42-1—42-56042-1—42-560 HH 环丙基Cyclopropyl ClCl ClCl 如表6As shown in Table 6
4343 43-1—43-56043-1—43-560 HH 环丙基Cyclopropyl BrBr HH 如表6As shown in Table 6
4444 44-1—44-56044-1—44-560 HH 环丙基Cyclopropyl HH BrBr 如表6As shown in Table 6
4545 45-1—45-56045-1—45-560 HH 环丙基Cyclopropyl BrBr BrBr 如表6As shown in Table 6
4646 46-1—46-56046-1—46-560 HH 2-丁基2-butyl HH HH 如表6As shown in Table 6
4747 47-1—47-56047-1—47-560 HH 2-丁基2-butyl 甲基methyl HH 如表6As shown in Table 6
4848 48-1—48-56048-1—48-560 HH 2-丁基2-butyl HH 甲基methyl 如表6As shown in Table 6
4949 49-1—49-56049-1—49-560 HH 2-丁基2-butyl 甲基methyl 甲基methyl 如表6As shown in Table 6
5050 50-1—50-56050-1—50-560 HH 2-丁基2-butyl FF HH 如表6As shown in Table 6
5151 51-1—51-56051-1—51-560 HH 2-丁基2-butyl HH FF 如表6As shown in Table 6
5252 52-1—52-56052-1—52-560 HH 2-丁基2-butyl FF FF 如表6As shown in Table 6
5353 53-1—53-56053-1—53-560 HH 2-丁基2-butyl ClCl HH 如表6As shown in Table 6
5454 54-1—54-56054-1—54-560 HH 2-丁基2-butyl HH ClCl 如表6As shown in Table 6
5555 55-1—55-56055-1—55-560 HH 2-丁基2-butyl ClCl ClCl 如表6As shown in Table 6
5656 56-1—56-56056-1—56-560 HH 2-丁基2-butyl BrBr HH 如表6As shown in Table 6
5757 57-1—57-56057-1—57-560 HH 2-丁基2-butyl HH BrBr 如表6As shown in Table 6
5858 58-1—58-56058-1—58-560 HH 2-丁基2-butyl BrBr BrBr 如表6As shown in Table 6
5959 59-1—59-56059-1—59-560 HH 2-甲基丙基1-基2-methylpropyl 1-yl HH HH 如表6As shown in Table 6
6060 60-1—60-56060-1—60-560 HH 2-甲基丙基1-基2-methylpropyl 1-yl 甲基methyl HH 如表6As shown in Table 6
6161 61-1—61-56061-1—61-560 HH 2-甲基丙基1-基2-methylpropyl 1-yl HH 甲基methyl 如表6As shown in Table 6
6262 62-1—62-56062-1—62-560 HH 2-甲基丙基1-基2-methylpropyl 1-yl 甲基methyl 甲基methyl 如表6As shown in Table 6
6363 63-1—63-56063-1—63-560 HH 2-甲基丙基1-基2-methylpropyl 1-yl FF HH 如表6As shown in Table 6
6464 64-1—64-56064-1—64-560 HH 2-甲基丙基1-基2-methylpropyl 1-yl HH FF 如表6As shown in Table 6
6565 65-1—65-56065-1—65-560 HH 2-甲基丙基1-基2-methylpropyl 1-yl FF FF 如表6As shown in Table 6
6666 66-1—66-56066-1—66-560 HH 2-甲基丙基1-基2-methylpropyl 1-yl ClCl HH 如表6As shown in Table 6
6767 67-1—67-56067-1—67-560 HH 2-甲基丙基1-基2-methylpropyl 1-yl HH ClCl 如表6As shown in Table 6
6868 68-1—68-56068-1—68-560 HH 2-甲基丙基1-基2-methylpropyl 1-yl ClCl ClCl 如表6As shown in Table 6
6969 69-1—69-56069-1—69-560 HH 2-甲基丙基1-基2-methylpropyl 1-yl BrBr HH 如表6As shown in Table 6
7070 70-1—70-56070-1—70-560 HH 2-甲基丙基1-基2-methylpropyl 1-yl HH BrBr 如表6As shown in Table 6
7171 71-1—71-56071-1—71-560 HH 2-甲基丙基1-基2-methylpropyl 1-yl BrBr BrBr 如表6As shown in Table 6
7272 72-1—72-56072-1—72-560 HH 环丁基Cyclobutyl HH HH 如表6As shown in Table 6
7373 73-1—73-56073-1—73-560 HH 环丁基Cyclobutyl 甲基methyl HH 如表6As shown in Table 6
7474 74-1—74-56074-1—74-560 HH 环丁基Cyclobutyl HH 甲基methyl 如表6As shown in Table 6
7575 75-1—75-56075-1—75-560 HH 环丁基Cyclobutyl 甲基methyl 甲基methyl 如表6As shown in Table 6
7676 76-1—76-56076-1—76-560 HH 环丁基Cyclobutyl FF HH 如表6As shown in Table 6
7777 77-1—77-56077-1—77-560 HH 环丁基Cyclobutyl HH FF 如表6As shown in Table 6
7878 78-1—78-56078-1—78-560 HH 环丁基Cyclobutyl FF FF 如表6As shown in Table 6
7979 79-1—79-56079-1—79-560 HH 环丁基Cyclobutyl ClCl HH 如表6As shown in Table 6
8080 80-1—80-56080-1—80-560 HH 环丁基Cyclobutyl HH ClCl 如表6As shown in Table 6
8181 81-1—81-56081-1—81-560 HH 环丁基Cyclobutyl ClCl ClCl 如表6As shown in Table 6
8282 82-1—82-56082-1—82-560 HH 环丁基Cyclobutyl BrBr HH 如表6As shown in Table 6
8383 83-1—83-56083-1—83-560 HH 环丁基Cyclobutyl HH BrBr 如表6As shown in Table 6
8484 84-1—84-56084-1—84-560 HH 环丁基Cyclobutyl BrBr BrBr 如表6As shown in Table 6
8585 85-1—85-56085-1—85-560 甲基methyl 叔丁基Tert-butyl HH HH 如表6As shown in Table 6
8686 86-1—86-56086-1—86-560 甲基methyl 叔丁基Tert-butyl 甲基methyl HH 如表6As shown in Table 6
8787 87-1—87-56087-1—87-560 甲基methyl 叔丁基Tert-butyl HH 甲基methyl 如表6As shown in Table 6
8888 88-1—88-56088-1—88-560 甲基methyl 叔丁基Tert-butyl 甲基methyl 甲基methyl 如表6As shown in Table 6
8989 89-1—89-56089-1—89-560 甲基methyl 叔丁基Tert-butyl FF HH 如表6As shown in Table 6
9090 90-1—90-56090-1—90-560 甲基methyl 叔丁基Tert-butyl HH FF 如表6As shown in Table 6
9191 91-1—91-56091-1—91-560 甲基methyl 叔丁基Tert-butyl FF FF 如表6As shown in Table 6
9292 92-1—92-56092-1—92-560 甲基methyl 叔丁基Tert-butyl ClCl HH 如表6As shown in Table 6
9393 93-1—93-56093-1—93-560 甲基methyl 叔丁基Tert-butyl HH ClCl 如表6As shown in Table 6
9494 94-1—94-56094-1—94-560 甲基methyl 叔丁基Tert-butyl ClCl ClCl 如表6As shown in Table 6
9595 95-1—95-56095-1—95-560 甲基methyl 叔丁基Tert-butyl BrBr HH 如表6As shown in Table 6
9696 96-1—96-56096-1—96-560 甲基methyl 叔丁基Tert-butyl HH BrBr 如表6As shown in Table 6
9797 97-1—97-56097-1—97-560 甲基methyl 叔丁基Tert-butyl BrBr BrBr 如表6As shown in Table 6
9898 98-1—98-56098-1—98-560 甲基methyl 异丙基Isopropyl HH HH 如表6As shown in Table 6
9999 99-1—99-56099-1—99-560 甲基methyl 异丙基Isopropyl 甲基methyl HH 如表6As shown in Table 6
100100 100-1—100-560100-1—100-560 甲基methyl 异丙基Isopropyl HH 甲基methyl 如表6As shown in Table 6
101101 101-1—101-560101-1—101-560 甲基methyl 异丙基Isopropyl 甲基methyl 甲基methyl 如表6As shown in Table 6
102102 102-1—102-560102-1—102-560 甲基methyl 异丙基Isopropyl FF HH 如表6As shown in Table 6
103103 103-1—103-560103-1—103-560 甲基methyl 异丙基Isopropyl HH FF 如表6As shown in Table 6
104104 104-1—104-560104-1—104-560 甲基methyl 异丙基Isopropyl FF FF 如表6As shown in Table 6
105105 105-1—105-560105-1—105-560 甲基methyl 异丙基Isopropyl ClCl HH 如表6As shown in Table 6
106106 106-1—106-560106-1—106-560 甲基methyl 异丙基Isopropyl HH ClCl 如表6As shown in Table 6
107107 107-1—107-560107-1—107-560 甲基methyl 异丙基Isopropyl ClCl ClCl 如表6As shown in Table 6
108108 108-1—108-560108-1—108-560 甲基methyl 异丙基Isopropyl BrBr HH 如表6As shown in Table 6
109109 109-1—109-560109-1—109-560 甲基methyl 异丙基Isopropyl HH BrBr 如表6As shown in Table 6
110110 110-1—110-560110-1—110-560 甲基methyl 异丙基Isopropyl BrBr BrBr 如表6As shown in Table 6
111111 111-1—111-560111-1—111-560 甲基methyl 环丙基Cyclopropyl HH HH 如表6As shown in Table 6
112112 112-1—112-560112-1—112-560 甲基methyl 环丙基Cyclopropyl 甲基methyl HH 如表6As shown in Table 6
113113 113-1—113-560113-1—113-560 甲基methyl 环丙基Cyclopropyl HH 甲基methyl 如表6As shown in Table 6
114114 114-1—114-560114-1—114-560 甲基methyl 环丙基Cyclopropyl 甲基methyl 甲基methyl 如表6As shown in Table 6
115115 115-1—115-560115-1—115-560 甲基methyl 环丙基Cyclopropyl FF HH 如表6As shown in Table 6
116116 116-1—116-560116-1—116-560 甲基methyl 环丙基Cyclopropyl HH FF 如表6As shown in Table 6
117117 117-1—117-560117-1—117-560 甲基methyl 环丙基Cyclopropyl FF FF 如表6As shown in Table 6
118118 118-1—118-560118-1—118-560 甲基methyl 环丙基Cyclopropyl ClCl HH 如表6As shown in Table 6
119119 119-1—119-560119-1—119-560 甲基methyl 环丙基Cyclopropyl HH ClCl 如表6As shown in Table 6
120120 120-1—120-560120-1—120-560 甲基methyl 环丙基Cyclopropyl ClCl ClCl 如表6As shown in Table 6
121121 121-1—121-560121-1—121-560 甲基methyl 环丙基Cyclopropyl BrBr HH 如表6As shown in Table 6
122122 122-1—122-560122-1—122-560 甲基methyl 环丙基Cyclopropyl HH BrBr 如表6As shown in Table 6
123123 123-1—123-560123-1—123-560 甲基methyl 环丙基Cyclopropyl BrBr BrBr 如表6As shown in Table 6
124124 124-1—124-560124-1—124-560 甲基methyl 2-丁基2-butyl HH HH 如表6As shown in Table 6
125125 125-1—125-560125-1—125-560 甲基methyl 2-丁基2-butyl 甲基methyl HH 如表6As shown in Table 6
126126 126-1—126-560126-1—126-560 甲基methyl 2-丁基2-butyl HH 甲基methyl 如表6As shown in Table 6
127127 127-1—127-560127-1—127-560 甲基methyl 2-丁基2-butyl 甲基methyl 甲基methyl 如表6As shown in Table 6
128128 128-1—128-560128-1—128-560 甲基methyl 2-丁基2-butyl FF HH 如表6As shown in Table 6
129129 129-1—129-560129-1—129-560 甲基methyl 2-丁基2-butyl HH FF 如表6As shown in Table 6
130130 130-1—130-560130-1—130-560 甲基methyl 2-丁基2-butyl FF FF 如表6As shown in Table 6
131131 131-1—131-560131-1—131-560 甲基methyl 2-丁基2-butyl ClCl HH 如表6As shown in Table 6
132132 132-1—132-560132-1—132-560 甲基methyl 2-丁基2-butyl HH ClCl 如表6As shown in Table 6
133133 133-1—133-560133-1—133-560 甲基methyl 2-丁基2-butyl ClCl ClCl 如表6As shown in Table 6
134134 134-1—134-560134-1—134-560 甲基methyl 2-丁基2-butyl BrBr HH 如表6As shown in Table 6
135135 135-1—135-560135-1—135-560 甲基methyl 2-丁基2-butyl HH BrBr 如表6As shown in Table 6
136136 136-1—136-560136-1—136-560 甲基methyl 2-丁基2-butyl BrBr BrBr 如表6As shown in Table 6
137137 137-1—137-560137-1—137-560 甲基methyl 2-甲基丙基1-基2-methylpropyl 1-yl HH HH 如表6As shown in Table 6
138138 138-1—138-560138-1—138-560 甲基methyl 2-甲基丙基1-基2-methylpropyl 1-yl 甲基methyl HH 如表6As shown in Table 6
139139 139-1—139-560139-1—139-560 甲基methyl 2-甲基丙基1-基2-methylpropyl 1-yl HH 甲基methyl 如表6As shown in Table 6
140140 140-1—140-560140-1—140-560 甲基methyl 2-甲基丙基1-基2-methylpropyl 1-yl 甲基methyl 甲基methyl 如表6As shown in Table 6
141141 141-1—141-560141-1—141-560 甲基methyl 2-甲基丙基1-基2-methylpropyl 1-yl FF HH 如表6As shown in Table 6
142142 142-1—142-560142-1—142-560 甲基methyl 2-甲基丙基1-基2-methylpropyl 1-yl HH FF 如表6As shown in Table 6
143143 143-1—143-560143-1—143-560 甲基methyl 2-甲基丙基1-基2-methylpropyl 1-yl FF FF 如表6As shown in Table 6
144144 144-1—144-560144-1—144-560 甲基methyl 2-甲基丙基1-基2-methylpropyl 1-yl ClCl HH 如表6As shown in Table 6
145145 145-1—145-560145-1—145-560 甲基methyl 2-甲基丙基1-基2-methylpropyl 1-yl HH ClCl 如表6As shown in Table 6
146146 146-1—146-560146-1—146-560 甲基methyl 2-甲基丙基1-基2-methylpropyl 1-yl ClCl ClCl 如表6As shown in Table 6
147147 147-1—147-560147-1—147-560 甲基methyl 2-甲基丙基1-基2-methylpropyl 1-yl BrBr HH 如表6As shown in Table 6
148148 148-1—148-560148-1—148-560 甲基methyl 2-甲基丙基1-基2-methylpropyl 1-yl HH BrBr 如表6As shown in Table 6
149149 149-1—149-560149-1—149-560 甲基methyl 2-甲基丙基1-基2-methylpropyl 1-yl BrBr BrBr 如表6As shown in Table 6
150150 150-1—150-560150-1—150-560 甲基methyl 环丁基Cyclobutyl HH HH 如表6As shown in Table 6
151151 151-1—151-560151-1—151-560 甲基methyl 环丁基Cyclobutyl 甲基methyl HH 如表6As shown in Table 6
152152 152-1—152-560152-1—152-560 甲基methyl 环丁基Cyclobutyl HH 甲基methyl 如表6As shown in Table 6
153153 153-1—153-560153-1—153-560 甲基methyl 环丁基Cyclobutyl 甲基methyl 甲基methyl 如表6As shown in Table 6
154154 154-1—154-560154-1—154-560 甲基methyl 环丁基Cyclobutyl FF HH 如表6As shown in Table 6
155155 155-1—155-560155-1—155-560 甲基methyl 环丁基Cyclobutyl HH FF 如表6As shown in Table 6
156156 156-1—156-560156-1—156-560 甲基methyl 环丁基Cyclobutyl FF FF 如表6As shown in Table 6
157157 157-1—157-560157-1—157-560 甲基methyl 环丁基Cyclobutyl ClCl HH 如表6As shown in Table 6
158158 158-1—158-560158-1—158-560 甲基methyl 环丁基Cyclobutyl HH ClCl 如表6As shown in Table 6
159159 159-1—159-560159-1—159-560 甲基methyl 环丁基Cyclobutyl ClCl ClCl 如表6As shown in Table 6
160160 160-1—160-560160-1—160-560 甲基methyl 环丁基Cyclobutyl BrBr HH 如表6As shown in Table 6
161161 161-1—161-560161-1—161-560 甲基methyl 环丁基Cyclobutyl HH BrBr 如表6As shown in Table 6
162162 162-1—162-560162-1—162-560 甲基methyl 环丁基Cyclobutyl BrBr BrBr 如表6As shown in Table 6
本发明通式I衍生物可以按照以下路线方法制备：The derivatives of general formula I of the present invention can be prepared according to the following route method:
Figure PCTCN2020131020-appb-000018
Figure PCTCN2020131020-appb-000018
X为卤素，氯、溴或碘。X is halogen, chlorine, bromine or iodine.
在上述反应式中，步骤一反应在适宜的溶剂中进行，适宜的溶剂可选自如乙酸乙酯、二氯甲烷、四氢呋喃、乙腈、甲苯、二甲苯、苯、N,N-二甲基甲酰胺、二甲亚砜等。In the above reaction formula, the step 1 reaction is carried out in a suitable solvent, and the suitable solvent can be selected from ethyl acetate, dichloromethane, tetrahydrofuran, acetonitrile, toluene, xylene, benzene, N,N-dimethylformamide , Dimethyl sulfoxide, etc.
在上述步骤1反应式中，反应在适宜的碱参与下进行，适宜的碱可选自叔丁醇钠、叔丁醇钾、氢化钠、氨基钠、氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、三乙胺、二异丙基乙基胺等。In the above step 1 reaction formula, the reaction is carried out with the participation of a suitable base, which can be selected from sodium tert-butoxide, potassium tert-butoxide, sodium hydride, sodium amide, sodium hydroxide, potassium hydroxide, sodium carbonate, Potassium carbonate, triethylamine, diisopropylethylamine, etc.
在上述步骤1反应式中，反应温度可在室温至溶剂沸点温度之间，通常为20-150℃。In the above step 1 reaction formula, the reaction temperature can be between room temperature and the boiling point of the solvent, usually 20-150°C.
在上述步骤1反应式中，反应时间为1小时至12小时，通常1-6小时。In the above step 1 reaction formula, the reaction time is 1 hour to 12 hours, usually 1-6 hours.
在上述步骤2反应式中，反应在适宜的溶剂中进行，适宜的溶剂可选自如乙酸乙酯、二氯甲烷、四氢呋喃、乙腈、甲苯、二甲苯、苯、N,N-二甲基甲酰胺、二甲亚砜等。In the above step 2 reaction formula, the reaction is carried out in a suitable solvent, which can be selected from ethyl acetate, dichloromethane, tetrahydrofuran, acetonitrile, toluene, xylene, benzene, N,N-dimethylformamide , Dimethyl sulfoxide, etc.
在上述步骤2反应式中，反应可在适宜的碱参与下进行，适宜的碱可选自叔丁醇钠、叔丁醇钾、氢化钠、氨基钠、氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、三乙胺、二异丙基乙基胺等。In the above step 2 reaction formula, the reaction can be carried out with the participation of a suitable base, which can be selected from sodium tert-butoxide, potassium tert-butoxide, sodium hydride, sodium amide, sodium hydroxide, potassium hydroxide, and sodium carbonate , Potassium carbonate, triethylamine, diisopropylethylamine, etc.
在上述步骤2反应式中，反应温度可在室温至溶剂沸点温度之间，通常为20-120℃。In the above step 2 reaction formula, the reaction temperature can be between room temperature and the boiling point of the solvent, usually 20-120°C.
在上述步骤2反应式中，反应时间为1小时至12小时，通常2-8小时。In the above step 2 reaction formula, the reaction time is 1 hour to 12 hours, usually 2-8 hours.
在上述步骤3反应式中，反应在适宜的溶剂中进行，适宜的溶剂可选自如甲醇、乙醇、丙醇、异丙醇、正丁醇、异丁醇、叔丁醇、水等。In the above reaction formula of Step 3, the reaction is carried out in a suitable solvent, which can be selected from methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol, tert-butanol, water and the like.
在上述步骤3反应式中，反应可在适宜的还原剂参与下进行，适宜的还原剂可选自硼氢化钠、硼氢化钾，以及氢气、水合肼等还原剂与贵金属钯、铂等的组合。In the above reaction formula of step 3, the reaction can be carried out with the participation of a suitable reducing agent, which can be selected from sodium borohydride, potassium borohydride, and combinations of reducing agents such as hydrogen, hydrazine hydrate, and precious metals such as palladium, platinum, etc. .
在上述步骤3反应式中，反应温度可在零度至溶剂沸点温度之间，通常为0-100℃。In the above step 3 reaction formula, the reaction temperature can be between zero and the boiling point of the solvent, usually 0-100°C.
在上述步骤3反应式中，反应时间为1小时至24小时，通常2-8小时。In the above step 3 reaction formula, the reaction time is 1 hour to 24 hours, usually 2-8 hours.
本发明所具有的优点：The advantages of the present invention:
本发明通式I化合物，具备出色延缓植物生长、抑制茎杆伸长、缩短植物节间等植物生长调节活性与杀菌剂活性，且具有更短的代谢残留时间，更容易分解，对后茬作物的影响更小。通式I化合物可望在农业生产领域发挥作用。The compound of general formula I of the present invention has excellent plant growth regulating activities and fungicidal activities such as delaying plant growth, inhibiting stem elongation, shortening plant nodes, etc., and has a shorter metabolic residue time, is easier to decompose, and is more effective for subsequent crops. The impact is even smaller. The compound of general formula I is expected to play a role in the field of agricultural production.
本发明通式I化合物，相比现市场药物与对比化合物，除具备出色的抑制作物茎杆伸长，矮化植株，防止倒伏活性外，其在土壤中的代谢时间短于现市场药物，减少了发生药害的可能性。本发明通式I化合物，相比现市场药物与对比化合物，在降低水稻株高的同时，对水稻产量的影响较小。本发明通式I化合物，相比现市场药物与对比化合物，还具备显著的促进作物提前开花功能，另因其快速的降解性能，对后续果实生长又可最大限度的降低药害，相比现有市场药物可减少用药风险，对于控制作物由营养生长至生殖生长的时间把控、果实提前成熟、产品错峰销售具有重大意义。Compared with current market drugs and comparative compounds, the compound of general formula I of the present invention has excellent activity in inhibiting crop stem elongation, dwarfing plants, and preventing lodging, and its metabolic time in the soil is shorter than that of current market drugs, reducing The possibility of phytotoxicity occurred. Compared with current market drugs and comparative compounds, the compound of general formula I of the present invention reduces the height of rice plants and has a smaller impact on rice yield. Compared with current market drugs and comparative compounds, the compound of general formula I of the present invention also has a significant function of promoting early flowering of crops. In addition, due to its rapid degradation performance, it can minimize phytotoxicity for subsequent fruit growth. There are marketable drugs that can reduce the risk of drug use, and are of great significance for controlling the time of crops from vegetative growth to reproductive growth, early ripening of fruits, and off-peak sales of products.
附图说明Description of the drawings
图1为本发明实施例提供的多效唑标准曲线。Fig. 1 is a standard curve of paclobutrazol provided by an embodiment of the present invention.
图2为本发明实施例提供的化合物6-375标准曲线。Figure 2 is a standard curve of compound 6-375 provided by an embodiment of the present invention.
图3为本发明实施例提供的土壤中多效唑降解动态趋势图。Figure 3 is a graph showing the dynamic trend of paclobutrazol degradation in soil provided by an embodiment of the present invention.
图4为本发明实施例提供的土壤中化合物6-375号药降解动态趋势图。Figure 4 is a graph showing the degradation dynamics of compound No. 6-375 in soil provided by an embodiment of the present invention.
图5为本发明实施例提供的加药后21天黄瓜生长发育图Figure 5 is a diagram of cucumber growth and development 21 days after drug addition provided by an embodiment of the present invention
具体实施方式Detailed ways
提供以下实施例描述以助于全面理解本发明的权利要求及其等同物限定，但不作为对本发明的限制。The following embodiment descriptions are provided to help a comprehensive understanding of the claims and equivalents of the present invention, but not as limitations on the present invention.
实施例1：化合物6-55的合成Example 1: Synthesis of compound 6-55
步骤A：Step A:
Figure PCTCN2020131020-appb-000019
Figure PCTCN2020131020-appb-000019
在100mL烧瓶中加入1-(1,2,4-三唑-1-基)-3,3-二甲基-2-丁酮3.3g，DMF 50mL，氢化钠1.0g，室温搅拌0.5小时，3-氯甲基-6-氯吡啶3.3g，搅拌加热80℃反应4小时，TLC检测反应完毕后，加水150mL，乙酸乙酯50mL×3萃取，合并有机相，无水硫酸钠干燥，柱层析(洗脱剂为乙酸乙酯与石油醚(沸程60-90℃)，体积比为1:2)纯化得到2.53g化合物1-(6-氯吡啶-3-基)2-(1,2,4-三唑-1-基)-4,4-二甲基-3-戊酮，白色固体即A6-55。 1H NMR(600MHz,DMSO- d6)δ8.63(s,1H),8.19(d,J＝2.2Hz,1H),7.96(s,1H),7.65(dd,J＝8.2,2.4Hz,1H),7.41 (d,J＝8.2Hz,1H),6.08(t,J＝7.7Hz,1H),3.31(d,J＝7.7Hz,2H),1.06(s,9H).m/z(％):293.09[M+H] + Add 3.3 g of 1-(1,2,4-triazol-1-yl)-3,3-dimethyl-2-butanone, 50 mL of DMF, and 1.0 g of sodium hydride to a 100 mL flask, and stir at room temperature for 0.5 hours. 3.3g of 3-chloromethyl-6-chloropyridine, stirred and heated at 80°C to react for 4 hours. After the reaction was detected by TLC, 150mL of water was added and extracted with 50mL of ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and the column layer Analysis (eluent is ethyl acetate and petroleum ether (boiling range 60-90℃), the volume ratio is 1:2) and purified to obtain 2.53g of compound 1-(6-chloropyridin-3-yl)2-(1, 2,4-Triazol-1-yl)-4,4-dimethyl-3-pentanone, white solid is A6-55. 1 H NMR(600MHz,DMSO- d6 )δ8.63(s,1H), 8.19(d,J=2.2Hz,1H),7.96(s,1H),7.65(dd,J=8.2,2.4Hz,1H ),7.41 (d,J=8.2Hz,1H),6.08(t,J=7.7Hz,1H),3.31(d,J=7.7Hz,2H),1.06(s,9H).m/z(% ):293.09[M+H] +
步骤B：Step B:
Figure PCTCN2020131020-appb-000020
Figure PCTCN2020131020-appb-000020
在100mL烧瓶中加入1-(6-氯吡啶-3-基)2-(1,2,4-三唑-1-基)-4,4-二甲基-3-戊酮1.5g，甲醇50mL，冰浴冷却搅拌下分批缓慢加入0.6g硼氢化钠，控制温度不要超过50℃，加毕，室温搅拌反应4小时，TLC检测反应完毕后，减压脱溶，加水150mL，用浓盐酸调pH＝7，乙酸乙酯50mL×3萃取，合并有机相，无水硫酸钠干燥，柱层析(洗脱剂为乙酸乙酯与石油醚(沸程60-90℃)，体积比为,1:1)纯化得到1.23g化合物6-55，白色固体。Add 1.5 g of 1-(6-chloropyridin-3-yl)2-(1,2,4-triazol-1-yl)-4,4-dimethyl-3-pentanone and methanol in a 100mL flask 50mL, slowly add 0.6g sodium borohydride in batches under cooling and stirring in an ice bath, controlling the temperature not to exceed 50℃, after the addition, stir at room temperature for 4 hours, TLC detects the completion of the reaction, desolvate under reduced pressure, add 150mL of water, and use concentrated hydrochloric acid Adjust pH=7, extract with ethyl acetate 50mL×3, combine the organic phases, dry with anhydrous sodium sulfate, and column chromatography (eluent is ethyl acetate and petroleum ether (boiling range 60-90℃), the volume ratio is, 1:1) Purified to obtain 1.23 g of compound 6-55 as a white solid.
按照上述制备方法制备获得部分化合物表征数据如下：According to the above preparation method, the characterization data of some compounds are as follows:
化合物6-18:Compounds 6-18:
1-(5-氯吡啶-2-基)-4,4-二甲基-2-(1H-1,2,4-三唑-1-基)戊烷-3-醇1-(5-chloropyridin-2-yl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentane-3-ol
Figure PCTCN2020131020-appb-000021
Figure PCTCN2020131020-appb-000021
1H NMR(600MHz,CDCl 3)δ8.49(d,J＝2.2Hz,1H),7.95(s,1H),7.91(s,1H),7.48(dd,J＝8.2,2.4Hz,1H),6.85(d,J＝8.2Hz,1H),5.19(dd,J＝8.6,5.9Hz,1H),4.31–4.16(m,1H),3.55(dd,J＝14.3,9.4Hz,1H),3.50(d,J＝7.1Hz,1H),3.34(dd,J＝14.4,5.5Hz,1H),0.71(s,9H). 1 H NMR(600MHz,CDCl 3 )δ8.49(d,J=2.2Hz,1H),7.95(s,1H),7.91(s,1H),7.48(dd,J=8.2,2.4Hz,1H) ,6.85(d,J=8.2Hz,1H),5.19(dd,J=8.6,5.9Hz,1H),4.31-4.16(m,1H),3.55(dd,J=14.3,9.4Hz,1H), 3.50 (d, J = 7.1Hz, 1H), 3.34 (dd, J = 14.4, 5.5Hz, 1H), 0.71 (s, 9H).
化合物6-47:Compound 6-47:
1-(6-甲氧基吡啶-3-基)-4,4-二甲基-2-(1H-1,2,4-三唑-1-基)戊烷-3-醇1-(6-Methoxypyridin-3-yl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentane-3-ol
Figure PCTCN2020131020-appb-000022
Figure PCTCN2020131020-appb-000022
1H NMR(600MHz,CDCl 3)δ7.96(s,1H),7.86(s,1H),7.79(d,J＝2.2Hz,1H),7.06(dd,J＝8.5,2.5Hz,1H),6.59(d,J＝8.5Hz,1H),4.56(dd,J＝9.8,6.6Hz,1H),3.88(s,3H),3.35(dd,J＝14.2,9.9Hz,1H),3.09(dd,J＝14.3,5.5Hz,1H),0.69(s,9H). 1 H NMR(600MHz,CDCl 3 )δ7.96(s,1H),7.86(s,1H),7.79(d,J=2.2Hz,1H), 7.06(dd,J=8.5,2.5Hz,1H) ,6.59(d,J=8.5Hz,1H),4.56(dd,J=9.8,6.6Hz,1H), 3.88(s,3H), 3.35(dd,J=14.2,9.9Hz,1H), 3.09( dd, J = 14.3, 5.5 Hz, 1H), 0.69 (s, 9H).
化合物6-55：Compound 6-55:
1-(6-氯吡啶-3-基)-4,4-二甲基-2-(1H-1,2,4-三唑-1-基)-3-戊醇1-(6-chloropyridin-3-yl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)-3-pentanol
Figure PCTCN2020131020-appb-000023
Figure PCTCN2020131020-appb-000023
1H NMR(600MHz,DMSO- d6)δ8.56(s,1H),8.11(d,J＝2.0Hz,1H),7.77(s,1H),7.60(dd,J＝8.2,2.2Hz,1H),7.34(d,J＝8.2Hz,1H),5.56(d,J＝6.4Hz,1H),4.79(dd,J＝10.9,4.3Hz,1H),3.46(d,J＝6.3Hz,1H),3.33(dd,J＝13.9,11.2Hz,1H),3.13(dd,J＝14.1,4.6Hz,1H),0.63(s,9H).m/z(％):295.12[M+H] + 1 H NMR(600MHz,DMSO- d6 )δ8.56(s,1H),8.11(d,J=2.0Hz,1H),7.77(s,1H),7.60(dd,J=8.2,2.2Hz,1H ), 7.34 (d, J = 8.2 Hz, 1H), 5.56 (d, J = 6.4 Hz, 1H), 4.79 (dd, J = 10.9, 4.3 Hz, 1H), 3.46 (d, J = 6.3 Hz, 1H ),3.33(dd,J=13.9,11.2Hz,1H),3.13(dd,J=14.1,4.6Hz,1H),0.63(s,9H).m/z(%):295.12[M+H] +
化合物6-59:Compound 6-59:
1-(6-溴吡啶-3-基)-4,4-二甲基-2-(1H-1,2,4-三唑-1-基)戊烷-3-醇1-(6-Bromopyridin-3-yl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentane-3-ol
Figure PCTCN2020131020-appb-000024
Figure PCTCN2020131020-appb-000024
1H NMR(600MHz,DMSO)δ8.56(s,1H),8.09(s,1H),7.77(s,1H),7.49(dd,J＝19.3,8.2Hz,2H),5.56(d,J＝5.3Hz,1H),4.79(dd,J＝10.9,4.2Hz,1H),3.46(d,J＝4.8Hz,1H),3.30(dd,J＝13.7,11.4Hz,1H),3.11(dd,J＝14.0,4.5Hz,1H),0.63(s,9H). 1 H NMR (600MHz, DMSO) δ8.56 (s, 1H), 8.09 (s, 1H), 7.77 (s, 1H), 7.49 (dd, J = 19.3, 8.2 Hz, 2H), 5.56 (d, J ＝5.3Hz,1H), 4.79(dd,J＝10.9,4.2Hz,1H), 3.46(d,J＝4.8Hz,1H), 3.30(dd,J＝13.7,11.4Hz,1H), 3.11(dd ,J=14.0,4.5Hz,1H),0.63(s,9H).
化合物6-166：Compound 6-166:
1-(2-氯嘧啶-5-基)-4,4-二甲基-2-(1H-1,2,4-三唑-1-基)戊烷-3-醇1-(2-Chloropyrimidin-5-yl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentane-3-ol
Figure PCTCN2020131020-appb-000025
Figure PCTCN2020131020-appb-000025
1H NMR(600MHz,CDCl 3)δ8.24(s,1H),8.00(s,1H),7.98(s,1H),4.64(dd,J＝9.4,5.4Hz,1H),3.70(d,J＝9.1Hz,1H),3.48-3.53(m,2H),3.18(dd,J＝14.4,5.4Hz,1H),0.70(s,9H). 1 H NMR (600MHz, CDCl 3 ) δ 8.24 (s, 1H), 8.00 (s, 1H), 7.98 (s, 1H), 4.64 (dd, J = 9.4, 5.4 Hz, 1H), 3.70 (d, J = 9.1Hz, 1H), 3.48-3.53 (m, 2H), 3.18 (dd, J = 14.4, 5.4 Hz, 1H), 0.70 (s, 9H).
化合物6-375:Compound 6-375:
1-(2-氯噻唑-5-基)-4,4-二甲基-2-(1H-1,2,4-三唑-1-基)戊烷-3-醇1-(2-Chlorothiazol-5-yl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentane-3-ol
Figure PCTCN2020131020-appb-000026
Figure PCTCN2020131020-appb-000026
1H NMR(600MHz,DMSO)δ8.57(s,1H),7.87(s,1H),7.30(s,1H),5.56(d,J＝6.5Hz,1H),4.74(dd,J＝11.1,3.5Hz,1H),3.57(dd,J＝15.1,11.1Hz,1H),3.47(dd,J＝6.5,1.2Hz,1H),3.35(dd,J＝15.6,4.7Hz,1H),0.63(s,9H). 1 H NMR(600MHz,DMSO)δ8.57(s,1H),7.87(s,1H),7.30(s,1H),5.56(d,J=6.5Hz,1H), 4.74(dd,J=11.1 ,3.5Hz,1H),3.57(dd,J＝15.1,11.1Hz,1H), 3.47(dd,J＝6.5,1.2Hz,1H), 3.35(dd,J＝15.6,4.7Hz,1H),0.63 (s,9H).
化合物B1Compound B1
1-(5-氯噻吩-2-基)-4,4-二甲基-2-(1H-1,2,4-三唑-1-基)戊烷-3-醇1-(5-Chlorothiophen-2-yl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentane-3-ol
Figure PCTCN2020131020-appb-000027
Figure PCTCN2020131020-appb-000027
1H NMR(600MHz,DMSO)δ8.52(s,1H),7.85(s,1H),6.84(d,J＝3.7Hz,1H),6.60(d,J＝3.7Hz,1H),5.49(d,J＝6.4Hz,1H),4.70(dd,J＝10.6,4.5Hz,1H),3.45(q,2H),3.28(dd,J＝15.1,4.6Hz,1H),0.62(s,9H). 1 H NMR (600MHz, DMSO) δ 8.52 (s, 1H), 7.85 (s, 1H), 6.84 (d, J = 3.7 Hz, 1H), 6.60 (d, J = 3.7 Hz, 1H), 5.49 ( d, J = 6.4Hz, 1H), 4.70 (dd, J = 10.6, 4.5 Hz, 1H), 3.45 (q, 2H), 3.28 (dd, J = 15.1, 4.6 Hz, 1H), 0.62 (s, 9H) ).
化合物A1Compound A1
1-(5-氯噻吩-2-基)-4,4-二甲基-2-(1H-1,2,4-三唑-1-基)戊烷-3-酮1-(5-Chlorothiophen-2-yl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentane-3-one
Figure PCTCN2020131020-appb-000028
Figure PCTCN2020131020-appb-000028
1H NMR(600MHz,CDCl 3)δ8.20(s,1H),7.92(s,1H),6.69(d,J＝3.6Hz,1H),6.48(d,J＝3.4Hz,1H),5.66(t,J＝7.5Hz,1H),3.47(dd,J＝15.0,7.1Hz,1H),3.37(dd,J＝15.0,7.9Hz,1H),1.08(s,9H). 1 H NMR (600MHz, CDCl 3 ) δ 8.20 (s, 1H), 7.92 (s, 1H), 6.69 (d, J = 3.6 Hz, 1H), 6.48 (d, J = 3.4 Hz, 1H), 5.66 (t,J=7.5Hz,1H), 3.47(dd,J=15.0,7.1Hz,1H), 3.37(dd,J=15.0,7.9Hz,1H), 1.08(s,9H).
化合物A-6-18:Compound A-6-18:
1-(6-氯吡啶-3-基)-4,4-二甲基-2-(1H-1,2,4-三唑-1-基)戊烷-3-酮1-(6-chloropyridin-3-yl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentane-3-one
Figure PCTCN2020131020-appb-000029
Figure PCTCN2020131020-appb-000029
1H NMR(600MHz,DMSO)δ8.63(s,1H),8.19(d,J＝2.2Hz,1H),7.96(s,1H),7.65(dd,J＝8.2,2.4Hz,1H),7.41(d,J＝8.2Hz,1H),6.08(t,J＝7.7Hz,1H),3.31(d,J＝7.7Hz,2H),1.06(s,9H). 1 H NMR(600MHz,DMSO)δ8.63(s,1H), 8.19(d,J=2.2Hz,1H), 7.96(s,1H), 7.65(dd,J=8.2,2.4Hz,1H), 7.41 (d, J = 8.2 Hz, 1H), 6.08 (t, J = 7.7 Hz, 1H), 3.31 (d, J = 7.7 Hz, 2H), 1.06 (s, 9H).
化合物A-6-166：Compound A-6-166:
1-(2-氯嘧啶-5-基)-4,4-二甲基-2-(1H-1,2,4-三唑-1-基)戊烷-3-酮1-(2-Chloropyrimidin-5-yl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentane-3-one
Figure PCTCN2020131020-appb-000030
Figure PCTCN2020131020-appb-000030
1H NMR(600MHz,DMSO)δ8.62(s,1H),8.52(s,2H),7.99(s,1H),6.13(t,J＝7.6Hz,1H),3.32(s,1H),3.30(s,1H),1.06(s,9H). 1 H NMR(600MHz,DMSO)δ8.62(s,1H),8.52(s,2H),7.99(s,1H), 6.13(t,J=7.6Hz,1H), 3.32(s,1H), 3.30(s,1H),1.06(s,9H).
化合物A-6-47:Compound A-6-47:
1-(6-甲氧基吡啶-3-基)-4,4-二甲基-2-(1H-1,2,4-三唑-1-基)戊烷-3-酮1-(6-Methoxypyridin-3-yl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentane-3-one
Figure PCTCN2020131020-appb-000031
Figure PCTCN2020131020-appb-000031
1H NMR(600MHz,CDCl 3)δ8.25(s,1H),7.90(s,1H),7.89(d,J＝2.3Hz,1H),7.24(dd,J＝8.5,2.5Hz,1H),6.65(d,J＝8.5Hz,1H),5.67(t,J＝7.7Hz,1H),3.89(s,3H),3.30(dd,J＝14.1,7.4Hz,1H),3.18(dd,J＝14.1,7.9Hz,1H),1.05(s,9H). 1 H NMR(600MHz,CDCl 3 )δ8.25(s,1H),7.90(s,1H),7.89(d,J=2.3Hz,1H), 7.24(dd,J=8.5,2.5Hz,1H) ,6.65(d,J=8.5Hz,1H), 5.67(t,J=7.7Hz,1H), 3.89(s,3H), 3.30(dd,J=14.1,7.4Hz,1H), 3.18(dd, J = 14.1, 7.9 Hz, 1H), 1.05 (s, 9H).
上述记载化合物代号中A为制备相对应化合物的中间体。In the above-mentioned compound code, A is an intermediate for preparing the corresponding compound.
同时，按照上述各合成实施例中记载的内容将相应的原料进行替换即可获得本发明通式I所示的其他化合物。At the same time, other compounds represented by the general formula I of the present invention can be obtained by replacing the corresponding raw materials according to the contents described in the above synthesis examples.
另外，将上述获得化合物按照常规方式与酸反应，进而获得相应的盐。In addition, the above-obtained compound is reacted with an acid in a conventional manner to obtain the corresponding salt.
应用例1Application example 1
将一定浓度的药液与融化的琼脂培养基混合，将催好芽的水稻种子点在培养基表面，培养一周，测量水稻生理株高。水稻品种为吉粳83，以水稻株高为抑制指标，未添加化合物的处理为空白对照，多效唑为阳性对照。A certain concentration of medicinal solution is mixed with the melted agar medium, and the sprouting rice seeds are spotted on the surface of the medium and cultivated for one week to measure the physiological plant height of the rice. The rice variety is Jijing 83, the rice plant height is used as the inhibition index, the treatment without compound added is the blank control, and the paclobutrazol is the positive control.
在50ppm剂量下，化合物6-55对水稻株高的抑制率大于30％，阳性药物多效唑对水稻株高的抑制率大于30％。At a dose of 50 ppm, the inhibitory rate of compound 6-55 on rice plant height was greater than 30%, and the inhibitory rate of the positive drug paclobutrazol on rice plant height was greater than 30%.
说明本发明该类化合物具有出色的延缓生长活性。It shows that the compound of the present invention has excellent growth retarding activity.
应用例2Application example 2
将一定浓度的化合物6-55与多效唑喷施于土壤上，化合物6-55与多效唑在土壤中的原始附着量分别为1.2mg/kg和1.1mg/kg,经取样检测，化合物6-55的半衰期小于2天，而多效唑的半衰期大于3天。A certain concentration of compound 6-55 and paclobutrazol were sprayed on the soil. The original adhesion amounts of compound 6-55 and paclobutrazol in the soil were 1.2 mg/kg and 1.1 mg/kg, respectively. The half-life is less than 2 days, while the half-life of paclobutrazol is greater than 3 days.
说明化合物6-55的半衰期小于多效唑，该类化合物具有更低的残留风险。This indicates that the half-life of compound 6-55 is less than that of paclobutrazol, and this type of compound has a lower residual risk.
应用例3离体杀菌活性测定Application Example 3 Determination of in vitro bactericidal activity
测定方法如下：采用高通量筛选方法，即将待测化合物样品用适合的溶剂(溶剂的种类如丙酮、甲醇、DMF等，并且依据其对样品的溶解能力而选择)溶解，配制成所需浓度待测液。在超净工作环境下，将待测液加入到96孔培养板的微孔中，再将油菜菌核病原菌繁殖体悬浮液(制备方法参考期刊论文:福建农林科技，1997年第三期，15页)加入其中，处理后的培养板放置在恒温培养箱中培养。24小时后进行调查，调查时目测病原菌繁殖体萌发或生长情况，并根据对照处理的萌发或生长情况，评价化合物抑菌活性，其中，以待测化合物样品等浓度溶剂水溶液作为CK对照。The determination method is as follows: a high-throughput screening method is adopted, that is, the sample of the compound to be tested is dissolved in a suitable solvent (the type of solvent is acetone, methanol, DMF, etc., and is selected according to its ability to dissolve the sample) to prepare the desired concentration The liquid to be tested. In an ultra-clean working environment, add the test solution to the microwells of the 96-well culture plate, and then add the rape sclerotium pathogen propagule suspension (for the preparation method, refer to the journal article: Fujian Agriculture and Forestry Science and Technology, 1997, third issue, 15 Page) is added to it, and the treated culture plate is placed in a constant temperature incubator for culture. The investigation was conducted 24 hours later. During the investigation, the germination or growth of the pathogen propagules was visually inspected, and the antibacterial activity of the compound was evaluated according to the germination or growth of the control treatment. Among them, the aqueous solution of the solvent with the same concentration of the test compound sample was used as the CK control.
部分化合物的离体抑菌活性(以抑制率表示)测试结果如下：The in vitro antibacterial activity (expressed by inhibition rate) of some compounds was tested as follows:
在50ppm剂量下，化合物6-55对油菜菌核病菌的抑制率大于80％，而CK为0。具有出色的杀菌活性。At a dose of 50 ppm, the inhibition rate of compound 6-55 against Sclerotinia sclerotiorum was greater than 80%, while CK was 0. Has excellent bactericidal activity.
应用例4Application example 4
将一定浓度的待测化合物样品与融化的琼脂混合，将催好芽的品种为盐丰47的水稻种子点在含有待测试化合物的琼脂表面，培养一周，测量水稻生理株高。以水稻株高为抑制指标，未添加化合物的处理为空白对照，多效唑为阳性对照。A certain concentration of the test compound sample is mixed with the melted agar, and the rice seed of the sprouting variety Yanfeng 47 is spotted on the surface of the agar containing the test compound, and cultivated for one week to measure the physiological plant height of the rice. The rice plant height was used as the inhibition index, the treatment without compound was used as the blank control, and the paclobutrazol was used as the positive control.
在50ppm剂量下，化合物6-18、化合物6-47、化合物6-55、化合物6-59、化合物6-166、化合物6-375对水稻株高的抑制率大于30％，阳性药物多效唑对水稻株高的抑制率大于30％。At a dose of 50 ppm, compound 6-18, compound 6-47, compound 6-55, compound 6-59, compound 6-166, compound 6-375 inhibited rice plant height by more than 30%. The positive drug paclobutrazol on rice The inhibition rate of plant height is greater than 30%.
说明该类化合物具有出色的延缓生长活性。This shows that this type of compound has excellent growth retarding activity.
应用例5Application example 5
试验作物水稻，品种为盐丰47。将水稻种子浸种24h，均匀的撒在育苗盘(54cm×27cm×6cm)中，待稻苗长至三叶后挑选长势均匀的移栽到种植盒(24cm×15cm×15cm)中，每个处理3盒，每盒栽水稻6穴，每穴5株，土壤为大田土。试验药剂为多效唑、烯效唑、化合物6-375和B1，同时设置空白对照。每个药剂设置10 -4g/mL、10 -5g/mL、和10 -6g/mL浓度，施药量为每穴添加133.4g/亩、13.34g/亩和1.334g/亩，施药量为根据加药量与盒土量计算。 The experimental crop rice, the variety is Yanfeng 47. Soak the rice seeds for 24 hours, and evenly spread them in the seedling tray (54cm×27cm×6cm). After the rice seedlings grow to three leaves, select them and transplant them into a planting box (24cm×15cm×15cm). Each treatment 3 boxes, each box planted 6 holes of rice, 5 plants in each hole, the soil is field soil. The test agents were paclobutrazol, uniconazole, compound 6-375 and B1, and a blank control was set at the same time. Each agent is set at the concentration of 10 -4 g/mL, 10 -5 g/mL, and 10 -6 g/mL, and the application rate is 133.4 g/mu, 13.34 g/mu and 1.334 g/mu per hole. The amount of medicine is calculated based on the amount of medicine added and the amount of soil in the box.
所述B1化合物参见化合物表征部分数据。For the B1 compound, refer to the data in the compound characterization section.
表163 不同药剂浓度对水稻生长及产量的影响Table 163 The influence of different pesticide concentrations on rice growth and yield
Figure PCTCN2020131020-appb-000032
Figure PCTCN2020131020-appb-000032
由以上不同药剂浓度对水稻生长及产量的影响可见，化合物6-375在10 -5g/mL与10 -6g/mL浓度下可以在矮化水稻株高的情况下不产生显著的减产，多效唑在10 -6g/mL浓度下与化合物6-375效果 相当，但在10 -5g/mL浓度下减产显著，其安全窗口显著低于化合物6-375。而烯效唑减产显著，化合物B1也有相当程度的减产。 It can be seen from the above effects of different chemical concentrations on the growth and yield of rice that compound 6-375 at concentrations of 10 -5 g/mL and 10 -6 g/mL can dwarf the rice plant height without significant yield reduction. Paclobutrazol has the same effect as compound 6-375 at a concentration of 10 -6 g/mL, but reduces production significantly at a concentration of 10 -5 g/mL, and its safety window is significantly lower than that of compound 6-375. However, the production of Uniconazole was reduced significantly, and the production of Compound B1 was also reduced to a considerable extent.
应用例6Application example 6
称取两份1kg干燥空白土壤置于方形整理箱中，分别向土壤中加入100mL浓度为1mg/mL的多效唑和化合物6-375溶液，使其终浓度均为100mg/kg。充分搅拌均匀后，分别在第1h、1、3、5、7、10、15、20、25d取样，并检测多效唑和化合物6-375在土壤中的残留量(参见图3和图4)。Weigh two 1kg dry blank soils and place them in a square finishing box, and add 100mL paclobutrazol and compound 6-375 solutions with a concentration of 1mg/mL to the soil to make the final concentration both 100mg/kg. After stirring well, samples were taken at 1h, 1, 3, 5, 7, 10, 15, 20, and 25d, and the residual amounts of paclobutrazol and compound 6-375 in the soil were detected (see Figure 3 and Figure 4).
分析与方法：Analysis and methods:
1)提取1) Extract
称取5g上述分别添加多效唑和化合物6-375溶液的土壤过20目筛后待用，含多效唑土壤样品按液质比5:1将土壤加入至25ml乙腈提取，含化合物6-375土壤样品按液质比3:1将土壤加入至15ml乙腈提取。涡旋振荡1min后，超声提取30min，-20℃低温速冻10min，10000rpm/min离心5min，回收上清液过0.22μm有机滤膜，待测。Weigh 5g of the soil added with paclobutrazol and compound 6-375 solution and pass it through a 20-mesh sieve for use. The soil sample containing paclobutrazol is added to 25ml acetonitrile at a liquid-to-mass ratio of 5:1, and the soil sample containing compound 6-375 is extracted by The liquid-to-mass ratio is 3:1. The soil is added to 15ml of acetonitrile for extraction. After vortexing for 1 min, ultrasonic extraction for 30 min, low temperature quick freezing at -20°C for 10 min, centrifugation at 10,000 rpm/min for 5 min, the supernatant was recovered and passed through a 0.22 μm organic filter membrane for testing.
2)液相色谱检测2) Liquid chromatography detection
多效唑与化合物6-375的检测条件相同，色谱柱(CAPCELL PAK C18 MG Ⅱ 4.6mm×250mm，5μm；Shiseido公司)，流动相：V(乙腈)∶V(水)＝55：45；流速：1.0mL/min；检测波长：222nm，进样量：20.0μL；柱温：30℃。The detection conditions of paclobutrazol and compound 6-375 are the same, chromatographic column (CAPCELL PAK C18 MG II 4.6mm×250mm, 5μm; Shiseido), mobile phase: V (acetonitrile): V (water) = 55: 45; flow rate: 1.0 mL/min; detection wavelength: 222nm, injection volume: 20.0μL; column temperature: 30°C.
3)标准曲线的绘制3) Drawing of standard curve
分别准确称取10mg多效唑与化合物6-375标准品于10mL容量瓶中，加入乙腈溶解并定容至刻度线，得到1000mg/L的标准溶液。随后用乙腈稀释得到浓度为100mg/L、50mg/L、20mg/L、10mg/L、5mg/L以及1mg/L的标准溶液。以多效唑与化合物6-375的浓度(x，mg/L)为横坐标轴，以其对应的峰面积(y)为纵坐标轴绘制标准曲线(参见图1和图2)。Accurately weigh 10 mg of paclobutrazol and compound 6-375 standard in a 10 mL volumetric flask, add acetonitrile to dissolve and dilute to the mark to obtain a 1000 mg/L standard solution. Then it was diluted with acetonitrile to obtain standard solutions with concentrations of 100 mg/L, 50 mg/L, 20 mg/L, 10 mg/L, 5 mg/L, and 1 mg/L. The concentration (x, mg/L) of paclobutrazol and compound 6-375 is taken as the abscissa axis, and the corresponding peak area (y) is taken as the ordinate axis to draw a standard curve (see Figure 1 and Figure 2).
如图1与2所示，两种药标准曲线分别为：y＝78.015x+19.753，R 2＝0.9993(多效唑)；y＝9.5048x+1.5506，R 2＝0.9999(化合物6-375)。 As shown in Figures 1 and 2, the standard curves of the two drugs are: y=78.015x+19.753, R 2 =0.9993 (Paclobutrazol); y=9.5048x+1.5506, R 2 =0.9999 (Compound 6-375).
由图3和图4可见，在土壤中加入多效唑和化合物6-375后，两种药的初始附着浓度分别为64.90mg/kg、84.14mg/kg。之后检测表明，多效唑的半衰期为10d，而化合物6-375半衰期为7d。此外，相比初始附着量，在第25d多效唑降解了57.77％，而化合物6-375降解了66.83％，这些结果表明在土壤中化合物6-375降解速率明显比多效唑快。因此，在保证合理施用的前提下，化合物6-375降解速率 快，土壤残留更低，对环境影响小，对后茬作物的种植安全性更高，不容易导致药害。It can be seen from Figure 3 and Figure 4 that after paclobutrazol and compound 6-375 were added to the soil, the initial adhesion concentrations of the two drugs were 64.90 mg/kg and 84.14 mg/kg, respectively. Later tests showed that the half-life of paclobutrazol was 10 days, while the half-life of compound 6-375 was 7 days. In addition, compared with the initial adhesion amount, paclobutrazol was degraded by 57.77% on the 25th day, while compound 6-375 was degraded by 66.83%. These results indicate that the degradation rate of compound 6-375 in the soil was significantly faster than paclobutrazol. Therefore, under the premise of ensuring reasonable application, compound 6-375 has a fast degradation rate, lower soil residue, less impact on the environment, higher planting safety for subsequent crops, and less likely to cause phytotoxicity.
应用例7Application example 7
试验作物为黄瓜，黄瓜种子放置25℃培养箱中进行催芽，待幼芽长至1cm后播种于种植盆(上口径12cm，下口径9cm，高11.5cm)中，土壤为草炭土，待黄瓜第一片真叶长出后施用复合肥(氮磷钾比例为15-15-15)。试验设置空白对照、试验药剂组、阳性对照组，试验药剂为化合物6-375和B1，阳性对照药剂为多效唑和烯效唑，分别为10 -4g/mL(每盆折合施用量4kg/hm 2)、10 -5g/mL(每盆折合施用量0.4kg/hm 2)、10 -6g/mL(每盆折合施用量0.04kg/hm 2)，折合施用量为根据加药量与盆土量计算。空白对照CK喷施清水。用药方式按照种植盆土壤体积计算每盆用药量。 The test crop was cucumber. Cucumber seeds were placed in an incubator at 25°C for accelerating germination. After the sprouts grew to 1cm, they were sown in planting pots (upper diameter 12cm, lower diameter 9cm, height 11.5cm). The soil was turf soil. After a true leaf grows, apply compound fertilizer (the ratio of nitrogen, phosphorus and potassium is 15-15-15). The experiment set up blank control, test agent group, and positive control group. The test agents were compound 6-375 and B1, and the positive control agents were paclobutrazol and uniconazole, respectively 10 -4 g/mL (each pot equivalent to 4kg/hm 2), 10 -5 g / mL ( equivalent to application rates per pot 0.4kg / hm 2), 10 -6 g / mL ( equivalent to application rates per pot 0.04kg / hm 2), according to an amount equivalent to administration and dosage Calculation of pot soil volume. The blank control CK was sprayed with water. The dosage of the medicine is calculated according to the soil volume of the planting pot.
表164 不同药剂浓度对黄瓜生长发育的影响Table 164 The effects of different pesticide concentrations on the growth and development of cucumber
Figure PCTCN2020131020-appb-000033
Figure PCTCN2020131020-appb-000033
由上表数据可见，多效唑、烯效唑和化合物B1在降低黄瓜的株高的同时严重影响了黄瓜的生长发育，在浓度10 -4g/mL与10 -5g/mL表现出显著的药害。而化合物6-375在10 -5g/mL与10 -6g/mL浓度下可以降低黄瓜的株高，且对黄瓜生长发育影响较小，且相对于空白对照与其他处理药剂具有显著的促进黄瓜提前开花的作用。说明化合物6-375在矮化作物株型同时，具有较大的用药浓度区间，与阳性对照药物和对比药物B1相比不容易导致作物药害，维持了黄瓜作物的正常生长发育，且可同时促进黄瓜作物提前开花，有助于缩短黄瓜生长周期，对农业生产具有重大的应用意义。 From the data in the above table, it can be seen that paclobutrazol, uniconazole and compound B1 severely affected the growth and development of cucumbers while reducing the plant height of cucumbers. They showed significant effects at concentrations of 10 -4 g/mL and 10 -5 g/mL. harm. The compound 6-375 can reduce the plant height of cucumber at the concentration of 10 -5 g/mL and 10 -6 g/mL, and has little effect on the growth and development of cucumber, and has a significant promotion compared with the blank control and other treatment agents. The effect of early flowering of cucumber. It shows that compound 6-375 has a larger concentration range for dwarfing crops. Compared with the positive control drug and the comparative drug B1, it is not easy to cause crop phytotoxicity, maintains the normal growth and development of cucumber crops, and can be used at the same time. Promote the early flowering of cucumber crops, help shorten the cucumber growth cycle, and have great application significance for agricultural production.
本发明合成的通式I化合物及其非对映异构体、手性异构体及其盐其可单独使用，或与农业上可接受的助剂以及其他药剂的混合制备可具备农业生产相关植物生长调节、杀菌等功能。The compound of general formula I synthesized by the present invention and its diastereomers, chiral isomers and their salts can be used alone, or mixed with agriculturally acceptable additives and other pharmaceutical agents. Plant growth regulation, sterilization and other functions.
本发明合成的通式I化合物及其非对映异构体、手性异构体及其盐可用于植物生长调节及杀菌剂的活性成分，可以单独使用，也可以与其它植物生长调节剂和杀菌剂联合使用。The compound of general formula I synthesized by the present invention and its diastereomers, chiral isomers and their salts can be used as active ingredients of plant growth regulators and fungicides, and can be used alone or in combination with other plant growth regulators and Fungicides are used in combination.

Claims (10)

  1. 一种三唑衍生物，其特征在于：三唑衍生物为通式I所示化合物、其非对映异构体、手性异构体或其盐：A triazole derivative, characterized in that: the triazole derivative is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
    Figure PCTCN2020131020-appb-100001
    Figure PCTCN2020131020-appb-100001
    其中among them
    R 1选自未取代或被1-5个R 8取代的含C、N、O或S的吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、噁唑基、异噁唑基、噻唑基、异噻唑基、噁二唑基或噻二唑基； R 1 is selected from unsubstituted or substituted by 1-5 R 8 containing C, N, O or S pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, oxazolyl, isoxazole Group, thiazolyl, isothiazolyl, oxadiazolyl or thiadiazolyl;
    R 2选自H、卤素、羟基、氨基、C 1-C 12烷基、卤代C 1-C 12烷基、C 1-C 12烷氧基、卤代C 1-C 12烷氧基、C 3-C 12环烷基、NR 6R 7、C(＝O)NR 6R 7、C 1-C 12烷硫基、卤代C 1-C 12烷硫基、C 2-C 12烯基、C 2-C 12炔基、C 2-C 12烯氧基、卤代C 2-C 12烯氧基、C 2-C 12炔氧基、卤代C 2-C 12炔氧基、C 1-C 12烷基磺酰基、卤代C 1-C 12烷基磺酰基、C 1-C 12烷基羰基、卤代C 1-C 12烷基羰基、C 1-C 12烷氧基羰基、卤代C 1-C 12烷氧基羰基、C 1-C 12烷氧基C 1-C 12烷基、卤代C 1-C 12烷氧基C 1-C 12烷基、C 1-C 12烷硫基C 1-C 12烷基、卤代C 1-C 12烷硫基C 1-C 12烷基、C 1-C 12烷氧基羰基C 1-C 12烷基、卤代C 1-C 12烷氧基羰基C 1-C 12烷基、C 1-C 12烷硫基羰基C 1-C 12烷基、卤代C 1-C 12烷硫基羰基C 1-C 12烷基、C 1-C 12烷基羰基氧基、卤代C 1-C 12烷基羰基氧基、C 1-C 12烷氧基羰基氧基、卤代C 1-C 12烷氧基羰基氧基、C 1-C 12烷基磺酰基氧基、卤代C 1-C 12烷基磺酰基氧基、C 1-C 12烷氧基C 1-C 12烷氧基或卤代C 1-C 12烷氧基C 1-C 12烷氧基； R 2 is selected from H, halogen, hydroxyl, amino, C 1 -C 12 alkyl, halogenated C 1 -C 12 alkyl, C 1 -C 12 alkoxy, halogenated C 1 -C 12 alkoxy, C 3 -C 12 cycloalkyl, NR 6 R 7 , C(=O)NR 6 R 7 , C 1 -C 12 alkylthio, halogenated C 1 -C 12 alkylthio, C 2 -C 12 alkene Group, C 2 -C 12 alkynyl, C 2 -C 12 alkenyloxy, halo C 2 -C 12 alkenyloxy, C 2 -C 12 alkynyloxy, halo C 2 -C 12 alkynyloxy, C 1 -C 12 alkylsulfonyl, halogenated C 1 -C 12 alkylsulfonyl, C 1 -C 12 alkylcarbonyl, halogenated C 1 -C 12 alkylcarbonyl, C 1 -C 12 alkoxy Carbonyl, halogenated C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkoxy C 1 -C 12 alkyl, halogenated C 1 -C 12 alkoxy C 1 -C 12 alkyl, C 1 -C 12 alkylthio C 1 -C 12 alkyl, halogenated C 1 -C 12 alkylthio C 1 -C 12 alkyl, C 1 -C 12 alkoxycarbonyl C 1 -C 12 alkyl, halogen Substituted C 1 -C 12 alkoxycarbonyl C 1 -C 12 alkyl, C 1 -C 12 alkylthiocarbonyl C 1 -C 12 alkyl, halogenated C 1 -C 12 alkylthiocarbonyl C 1 -C 12 alkyl, C 1 -C 12 alkylcarbonyloxy, halogenated C 1 -C 12 alkylcarbonyloxy, C 1 -C 12 alkoxycarbonyloxy, halogenated C 1 -C 12 alkoxy Carbonyloxy, C 1 -C 12 alkylsulfonyloxy, halogenated C 1 -C 12 alkylsulfonyloxy, C 1 -C 12 alkoxy C 1 -C 12 alkoxy or halogenated C 1 -C 12 alkoxy C 1 -C 12 alkoxy;
    R 3选自H、C 1-C 12烷基、卤代C 1-C 12烷基、C 1-C 12烷氧基、卤代C 1-C 12烷氧基、C 3-C 12环烷基、C(＝O)NR 6R 7、C 1-C 12烷硫基、卤代C 1-C 12烷硫基、C 2-C 12烯基、C 2-C 12炔基、C 2-C 12烯氧基、卤代C 2-C 12烯氧基、C 2-C 12炔氧基、卤代C 2-C 12炔氧基、C 1-C 12烷基磺酰基、卤代C 1-C 12烷基磺酰基、C 1-C 12烷基羰基、卤代C 1-C 12烷基羰基、C 1-C 12烷氧基羰基、卤代C 1-C 12烷氧基羰基、C 1-C 12烷氧基C 1-C 12烷基、卤代C 1-C 12烷氧基C 1-C 12烷基、C 1-C 12烷硫基C 1-C 12烷基、卤代C 1-C 12烷硫基C 1-C 12烷基、C 1-C 12烷氧基羰基C 1-C 12烷基、卤代C 1-C 12烷氧基羰基C 1-C 12烷基、C 1-C 12烷硫基羰基C 1-C 12烷基、卤代C 1-C 12烷硫基羰基C 1-C 12烷基、C 1-C 12烷基羰基氧基、卤代C 1-C 12烷基羰基氧基、C 1-C 12烷氧基羰基氧基、卤代C 1-C 12烷氧基羰基氧基、C 1-C 12烷基磺酰基氧基、卤代C 1-C 12烷基磺酰基氧基、C 1-C 12烷氧基C 1-C 12烷氧基 或卤代C 1-C 12烷氧基C 1-C 12烷氧基； R 3 is selected from H, C 1 -C 12 alkyl, halogenated C 1 -C 12 alkyl, C 1 -C 12 alkoxy, halogenated C 1 -C 12 alkoxy, C 3 -C 12 ring Alkyl, C(=O)NR 6 R 7 , C 1 -C 12 alkylthio, halogenated C 1 -C 12 alkylthio, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, C 2- C 12 alkenyloxy, halogenated C 2 -C 12 alkenyloxy, C 2 -C 12 alkynyloxy, halogenated C 2 -C 12 alkynyloxy, C 1 -C 12 alkylsulfonyl, halogen C 1 -C 12 alkylsulfonyl, C 1 -C 12 alkylcarbonyl, halogenated C 1 -C 12 alkylcarbonyl, C 1 -C 12 alkoxycarbonyl, halogenated C 1 -C 12 alkoxy Alkyl carbonyl, C 1 -C 12 alkoxy C 1 -C 12 alkyl, halogenated C 1 -C 12 alkoxy C 1 -C 12 alkyl, C 1 -C 12 alkylthio C 1 -C 12 Alkyl, halogenated C 1 -C 12 alkylthio C 1 -C 12 alkyl, C 1 -C 12 alkoxycarbonyl C 1 -C 12 alkyl, halogenated C 1 -C 12 alkoxycarbonyl C 1 -C 12 alkyl, C 1 -C 12 alkylthiocarbonyl C 1 -C 12 alkyl, halogenated C 1 -C 12 alkylthiocarbonyl C 1 -C 12 alkyl, C 1 -C 12 alkyl Carbonyloxy, halogenated C 1 -C 12 alkylcarbonyloxy, C 1 -C 12 alkoxycarbonyloxy, halogenated C 1 -C 12 alkoxycarbonyloxy, C 1 -C 12 alkyl Sulfonyloxy, halogenated C 1 -C 12 alkylsulfonyloxy, C 1 -C 12 alkoxy C 1 -C 12 alkoxy or halogenated C 1 -C 12 alkoxy C 1 -C 12 alkoxy;
    R 4与R 5相同或不同选自H、卤素、羟基、氨基、硝基、氰基、C 1-C 12烷基、卤代C 1-C 12烷基、C 1-C 12烷氧基、卤代C 1-C 12烷氧基、C 3-C 12环烷基、NR 6R 7、C(＝O)NR 6R 7、C 1-C 12烷硫基、卤代C 1-C 12烷硫基、C 2-C 12烯基、C 2-C 12炔基、C 2-C 12烯氧基、卤代C 2-C 12烯氧基、C 2-C 12炔氧基、卤代C 2-C 12炔氧基、C 1-C 12烷基磺酰基、卤代C 1-C 12烷基磺酰基、C 1-C 12烷基羰基、卤代C 1-C 12烷基羰基、C 1-C 12烷氧基羰基、卤代C 1-C 12烷氧基羰基、C 1-C 12烷氧基C 1-C 12烷基、卤代C 1-C 12烷氧基C 1-C 12烷基、C 1-C 12烷硫基C 1-C 12烷基、卤代C 1-C 12烷硫基C 1-C 12烷基、C 1-C 12烷氧基羰基C 1-C 12烷基、卤代C 1-C 12烷氧基羰基C 1-C 12烷基、C 1-C 12烷硫基羰基C 1-C 12烷基、卤代C 1-C 12烷硫基羰基C 1-C 12烷基、C 1-C 12烷基羰基氧基、卤代C 1-C 12烷基羰基氧基、C 1-C 12烷氧基羰基氧基、卤代C 1-C 12烷氧基羰基氧基、C 1-C 12烷基磺酰基氧基、卤代C 1-C 12烷基磺酰基氧基、C 1-C 12烷氧基C 1-C 12烷氧基或卤代C 1-C 12烷氧基C 1-C 12烷氧基； R 4 and R 5 are the same or different selected from H, halogen, hydroxy, amino, nitro, cyano, C 1 -C 12 alkyl, halogenated C 1 -C 12 alkyl, C 1 -C 12 alkoxy , Halogenated C 1 -C 12 alkoxy, C 3 -C 12 cycloalkyl, NR 6 R 7 , C(=O)NR 6 R 7 , C 1 -C 12 alkylthio, halogenated C 1- C 12 alkylthio, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, C 2 -C 12 alkenyloxy, halogenated C 2 -C 12 alkenyloxy, C 2 -C 12 alkynyloxy , Halogenated C 2 -C 12 alkynyloxy, C 1 -C 12 alkylsulfonyl, halogenated C 1 -C 12 alkylsulfonyl, C 1 -C 12 alkylcarbonyl, halogenated C 1 -C 12 Alkylcarbonyl, C 1 -C 12 alkoxycarbonyl, halogenated C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkoxy C 1 -C 12 alkyl, halogenated C 1 -C 12 alkane Oxygen C 1 -C 12 alkyl, C 1 -C 12 alkylthio C 1 -C 12 alkyl, halogenated C 1 -C 12 alkylthio C 1 -C 12 alkyl, C 1 -C 12 alkyl Oxycarbonyl C 1 -C 12 alkyl, halogenated C 1 -C 12 alkoxycarbonyl C 1 -C 12 alkyl, C 1 -C 12 alkylthiocarbonyl C 1 -C 12 alkyl, halogenated C 1 -C 12 alkylthiocarbonyl C 1 -C 12 alkyl, C 1 -C 12 alkylcarbonyloxy, halogenated C 1 -C 12 alkylcarbonyloxy, C 1 -C 12 alkoxycarbonyloxy Group, halogenated C 1 -C 12 alkoxycarbonyloxy, C 1 -C 12 alkylsulfonyloxy, halogenated C 1 -C 12 alkylsulfonyloxy, C 1 -C 12 alkoxy C 1 -C 12 alkoxy or halogenated C 1 -C 12 alkoxy C 1 -C 12 alkoxy;
    R 6、R 7相同或不同的分别选自氢、羟基、氨基、C 1-C 12烷基、卤代C 1-C 12烷基、C 1-C 12烷氧基或卤代C 1-C 12烷氧基，C 1-C 12烷基氨基，卤代C 1-C 12烷基氨基； R 6 and R 7 which are the same or different are selected from hydrogen, hydroxyl, amino, C 1 -C 12 alkyl, halogenated C 1 -C 12 alkyl, C 1 -C 12 alkoxy or halogenated C 1- C 12 alkoxy, C 1 -C 12 alkylamino, halogenated C 1 -C 12 alkylamino;
    其中，R 6、R 7还可以与其相连的N组成含C、N、O或S的三元、四元、五元、六元、七元或八元杂环烷烃； Wherein, R 6 , R 7 can also be connected to the N to form a three-membered, four-membered, five-membered, six-membered, seven-membered or eight-membered heterocycloalkane containing C, N, O or S;
    R 8选自H、卤素、羟基、氨基、硝基、氰基、C 1-C 12烷基、卤代C 1-C 12烷基、C 1-C 12烷氧基、卤代C 1-C 12烷氧基、C 3-C 12环烷基、NR 6R 7、C(＝O)NR 6R 7、C 1-C 12烷硫基、卤代C 1-C 12烷硫基、C 2-C 12烯基、C 2-C 12炔基、C 2-C 12烯氧基、卤代C 2-C 12烯氧基、C 2-C 12炔氧基、卤代C 2-C 12炔氧基、C 1-C 12烷基磺酰基、卤代C 1-C 12烷基磺酰基、C 1-C 12烷基羰基、卤代C 1-C 12烷基羰基、C 1-C 12烷氧基羰基、卤代C 1-C 12烷氧基羰基、C 1-C 12烷氧基C 1-C 12烷基、卤代C 1-C 12烷氧基C 1-C 12烷基、C 1-C 12烷硫基C 1-C 12烷基、卤代C 1-C 12烷硫基C 1-C 12烷基、C 1-C 12烷氧基羰基C 1-C 12烷基、卤代C 1-C 12烷氧基羰基C 1-C 12烷基、C 1-C 12烷硫基羰基C 1-C 12烷基、卤代C 1-C 12烷硫基羰基C 1-C 12烷基、C 1-C 12烷基羰基氧基、卤代C 1-C 12烷基羰基氧基、C 1-C 12烷氧基羰基氧基、卤代C 1-C 12烷氧基羰基氧基、C 1-C 12烷基磺酰基氧基、卤代C 1-C 12烷基磺酰基氧基、C 1-C 12烷氧基C 1-C 12烷氧基或卤代C 1-C 12烷氧基C 1-C 12烷氧基。 R 8 is selected from H, halogen, hydroxyl, amino, nitro, cyano, C 1 -C 12 alkyl, halogenated C 1 -C 12 alkyl, C 1 -C 12 alkoxy, halogenated C 1- C 12 alkoxy, C 3 -C 12 cycloalkyl, NR 6 R 7 , C(=O)NR 6 R 7 , C 1 -C 12 alkylthio, halogenated C 1 -C 12 alkylthio, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, C 2 -C 12 alkenyloxy, halogenated C 2 -C 12 alkenyloxy, C 2 -C 12 alkynyloxy, halogenated C 2- C 12 alkynyloxy, C 1 -C 12 alkylsulfonyl, halogenated C 1 -C 12 alkylsulfonyl, C 1 -C 12 alkylcarbonyl, halogenated C 1 -C 12 alkylcarbonyl, C 1 -C 12 alkoxycarbonyl, halogenated C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkoxy C 1 -C 12 alkyl, halogenated C 1 -C 12 alkoxy C 1 -C 12 alkyl, C 1 -C 12 alkylthio C 1 -C 12 alkyl, halogenated C 1 -C 12 alkylthio C 1 -C 12 alkyl, C 1 -C 12 alkoxycarbonyl C 1- C 12 alkyl, halogenated C 1 -C 12 alkoxycarbonyl C 1 -C 12 alkyl, C 1 -C 12 alkylthiocarbonyl C 1 -C 12 alkyl, halogenated C 1 -C 12 alkylthio C 1 -C 12 alkyl, C 1 -C 12 alkylcarbonyloxy, halogenated C 1 -C 12 alkylcarbonyloxy, C 1 -C 12 alkoxycarbonyloxy, halogenated C 1 -C 12 alkoxycarbonyloxy, C 1 -C 12 alkylsulfonyloxy, halogenated C 1 -C 12 alkylsulfonyloxy, C 1 -C 12 alkoxy C 1 -C 12 alkane Oxy or halo C 1 -C 12 alkoxy C 1 -C 12 alkoxy.
  2. 按权利要求1的三唑衍生物，其特征在于：所述三唑衍生物为通式I所示化合物、其非对映异构体、手性异构体或其盐：The triazole derivative according to claim 1, wherein the triazole derivative is a compound represented by formula I, its diastereomers, chiral isomers or salts thereof:
    式中Where
    R 1选自未取代或被1-5个R 8取代的含C、N、O或S的吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、噁唑基、异噁唑基、噻唑基、异 噻唑基、噁二唑基或噻二唑基； R 1 is selected from unsubstituted or substituted by 1-5 R 8 containing C, N, O or S pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, oxazolyl, isoxazole Group, thiazolyl, isothiazolyl, oxadiazolyl or thiadiazolyl;
    R 2选自H、卤素、C 1-C 6烷基、卤代C 1-C 6烷基、C 3-C 6环烷基、C 2-C 6烯基、C 2-C 6炔基、C 1-C 6烷氧基C 1-C 6烷基、卤代C 1-C 6烷氧基C 1-C 6烷基、C 1-C 6烷硫基C 1-C 6烷基、卤代C 1-C 6烷硫基C 1-C 6烷基、C 1-C 6烷氧基羰基C 1-C 6烷基、卤代C 1-C 6烷氧基羰基C 1-C 6烷基、C 1-C 6烷硫基羰基C 1-C 6烷基或卤代C 1-C 6烷硫基羰基C 1-C 6烷基； R 2 is selected from H, halogen, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl , C 1 -C 6 alkoxy C 1 -C 6 alkyl, halogenated C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylthio C 1 -C 6 alkyl , Halogenated C 1 -C 6 alkylthio C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, halogenated C 1 -C 6 alkoxycarbonyl C 1- C 6 alkyl, C 1 -C 6 alkylthiocarbonyl C 1 -C 6 alkyl or halogenated C 1 -C 6 alkylthiocarbonyl C 1 -C 6 alkyl;
    R 3选自H、C 1-C 6烷基、卤代C 1-C 6烷基、C 3-C 6环烷基、C 2-C 6烯基、C 2-C 6炔基、C 1-C 6烷氧基C 1-C 6烷基、卤代C 1-C 6烷氧基C 1-C 6烷基、C 1-C 6烷硫基C 1-C 6烷基、卤代C 1-C 6烷硫基C 1-C 6烷基、C 1-C 6烷氧基羰基C 1-C 6烷基、卤代C 1-C 6烷氧基羰基C 1-C 6烷基、C 1-C 6烷硫基羰基C 1-C 6烷基或卤代C 1-C 6烷硫基羰基C 1-C 6烷基； R 3 is selected from H, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl, halogenated C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylthio C 1 -C 6 alkyl, halogen C 1 -C 6 alkylthio C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, halogenated C 1 -C 6 alkoxycarbonyl C 1 -C 6 Alkyl, C 1 -C 6 alkylthiocarbonyl C 1 -C 6 alkyl or halogenated C 1 -C 6 alkylthiocarbonyl C 1 -C 6 alkyl;
    R 4与R 5相同或不同选自H、卤素、羟基、氨基、硝基、氰基、C 1-C 6烷基、卤代C 1-C 6烷基、C 3-C 6环烷基、C 2-C 6烯基、C 2-C 6炔基、C 1-C 6烷氧基C 1-C 6烷基、卤代C 1-C 6烷氧基C 1-C 6烷基、C 1-C 6烷硫基C 1-C 6烷基、卤代C 1-C 6烷硫基C 1-C 6烷基、C 1-C 6烷氧基羰基C 1-C 6烷基、卤代C 1-C 6烷氧基羰基C 1-C 6烷基、C 1-C 6烷硫基羰基C 1-C 6烷基、卤代C 1-C 6烷硫基羰基C 1-C 6烷基； R 4 and R 5 are the same or different selected from H, halogen, hydroxy, amino, nitro, cyano, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl, halogenated C 1 -C 6 alkoxy C 1 -C 6 alkyl , C 1 -C 6 alkylthio C 1 -C 6 alkyl, halogenated C 1 -C 6 alkylthio C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkane Group, halogenated C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, C 1 -C 6 alkylthiocarbonyl C 1 -C 6 alkyl, halogenated C 1 -C 6 alkylthiocarbonyl C 1 -C 6 alkyl;
    R 6、R 7相同或不同的分别选自氢、羟基、氨基、C 1-C 6烷基、卤代C 1-C 6烷基、C 1-C 6烷氧基或卤代C 1-C 6烷氧基，C 1-C 6烷基氨基，卤代C 1-C 6烷基氨基； R 6 and R 7 that are the same or different are selected from hydrogen, hydroxyl, amino, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 1 -C 6 alkoxy or halo C 1- C 6 alkoxy, C 1 -C 6 alkylamino, halogenated C 1 -C 6 alkylamino;
    其中，R 6、R 7还可以与其相连的N组成含C、N、O或S的三元、四元、五元、六元、七元或八元杂环烷烃； Wherein, R 6 , R 7 can also be connected to the N to form a three-membered, four-membered, five-membered, six-membered, seven-membered or eight-membered heterocycloalkane containing C, N, O or S;
    R 8选自H、卤素、羟基、氨基、硝基、氰基、C 1-C 6烷基、卤代C 1-C 6烷基、C 1-C 6烷氧基、卤代C 1-C 6烷氧基、C 3-C 6环烷基、NR 6R 7、C(＝O)NR 6R 7、C 1-C 6烷硫基、卤代C 1-C 6烷硫基、C 2-C 6烯基、C 2-C 6炔基、C 2-C 6烯氧基、卤代C 2-C 6烯氧基、C 2-C 6炔氧基、卤代C 2-C 6炔氧基、C 1-C 6烷基磺酰基、卤代C 1-C 6烷基磺酰基、C 1-C 6烷基羰基、卤代C 1-C 6烷基羰基、C 1-C 6烷氧基羰基、卤代C 1-C 6烷氧基羰基、C 1-C 6烷氧基C 1-C 6烷基、卤代C 1-C 6烷氧基C 1-C 6烷基、C 1-C 6烷硫基C 1-C 6烷基、卤代C 1-C 6烷硫基C 1-C 6烷基、C 1-C 6烷基羰基氧基、卤代C 1-C 6烷基羰基氧基、C 1-C 6烷基磺酰基氧基、卤代C 1-C 6烷基磺酰基氧基、C 1-C 6烷氧基C 1-C 6烷氧基或卤代C 1-C 6烷氧基C 1-C 6烷氧基。 R 8 is selected from H, halogen, hydroxyl, amino, nitro, cyano, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo C 1- C 6 alkoxy, C 3 -C 6 cycloalkyl, NR 6 R 7 , C(=O)NR 6 R 7 , C 1 -C 6 alkylthio, halogenated C 1 -C 6 alkylthio, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 2 -C 6 alkenyloxy, halogenated C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, halogenated C 2- C 6 alkynyloxy, C 1 -C 6 alkylsulfonyl, halogenated C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylcarbonyl, halogenated C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, halogenated C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl, halogenated C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylthio, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkylthio, C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy, halogen Substituted C 1 -C 6 alkylcarbonyloxy group, C 1 -C 6 alkylsulfonyloxy group, halogenated C 1 -C 6 alkylsulfonyloxy group, C 1 -C 6 alkoxy group C 1 -C 6 Alkoxy or halo C 1 -C 6 alkoxy C 1 -C 6 alkoxy.
  3. 按权利要求2的三唑衍生物，其特征在于：所述三唑衍生物为通式I所示化合物、其非对映异构体、手性异构体或其盐：The triazole derivative according to claim 2, characterized in that: the triazole derivative is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
    式中Where
    R 1选自未取代或被1-5个R 8取代的含C、N、O或S的吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、噁唑基、异噁唑基、噻唑基、异噻唑基、噁二唑基或噻二唑基； R 1 is selected from unsubstituted or substituted by 1-5 R 8 containing C, N, O or S pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, oxazolyl, isoxazole Group, thiazolyl, isothiazolyl, oxadiazolyl or thiadiazolyl;
    R 2选自H、卤素、C 1-C 3烷基、卤代C 1-C 3烷基、C 3-C 4环烷基； R 2 is selected from H, halogen, C 1 -C 3 alkyl, halo C 1 -C 3 alkyl, C 3 -C 4 cycloalkyl;
    R 3选自H、C 1-C 4烷基； R 3 is selected from H, C 1 -C 4 alkyl;
    R 4与R 5相同或不同选自H、卤素、C 1-C 3烷基； R 4 and R 5 are the same or different and are selected from H, halogen, C 1 -C 3 alkyl;
    R 6、R 7相同或不同的分别选自氢、C 1-C 3烷基； R 6 and R 7 that are the same or different are selected from hydrogen and C 1 -C 3 alkyl groups;
    其中，R 6、R 7还可以与其相连的N组成含C、N、O或S的三元、四元、五元或六元杂环烷烃； Among them, R 6 , R 7 can also be connected to the N to form a three-membered, four-membered, five-membered or six-membered heterocycloalkane containing C, N, O or S;
    R 8选自H、卤素、羟基、氨基、硝基、氰基、C 1-C 3烷基、卤代C 1-C 3烷基、C 1-C 3烷氧基、卤代C 1-C 3烷氧基、C 3-C 4环烷基、NR 6R 7、C(＝O)NR 6R 7、C 1-C 3烷硫基、卤代C 1-C 3烷硫基、C 2-C 4烯基、C 2-C 4炔基、C 1-C 3烷基磺酰基、卤代C 1-C 3烷基磺酰基、C 1-C 3烷基羰基、卤代C 1-C 3烷基羰基、C 1-C 3烷氧基羰基、卤代C 1-C 3烷氧基羰基、C 1-C 3烷基羰基氧基、卤代C 1-C 3烷基羰基氧基、C 1-C 3烷基磺酰基氧基、卤代C 1-C 3烷基磺酰基氧基、C 1-C 3烷氧基C 1-C 3烷氧基或卤代C 1-C 3烷氧基C 1-C 3烷氧基。 R 8 is selected from H, halogen, hydroxyl, amino, nitro, cyano, C 1 -C 3 alkyl, halo C 1 -C 3 alkyl, C 1 -C 3 alkoxy, halo C 1- C 3 alkoxy, C 3 -C 4 cycloalkyl, NR 6 R 7 , C(=O)NR 6 R 7 , C 1 -C 3 alkylthio, halogenated C 1 -C 3 alkylthio, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkylsulfonyl, halogenated C 1 -C 3 alkylsulfonyl, C 1 -C 3 alkylcarbonyl, halogenated C 1 -C 3 alkylcarbonyl, C 1 -C 3 alkoxycarbonyl, halogenated C 1 -C 3 alkoxycarbonyl, C 1 -C 3 alkylcarbonyloxy, halogenated C 1 -C 3 alkyl Carbonyloxy, C 1 -C 3 alkylsulfonyloxy, halogenated C 1 -C 3 alkylsulfonyloxy, C 1 -C 3 alkoxy C 1 -C 3 alkoxy or halogenated C 1 -C 3 alkoxy C 1 -C 3 alkoxy.
  4. 按权利要求3的三唑衍生物，其特征在于：所述三唑衍生物为通式I所示化合物、其非对映异构体、手性异构体或其盐：The triazole derivative according to claim 3, characterized in that: the triazole derivative is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
    式中Where
    R 1选自未取代或被1-5个R 8取代的吡啶基、嘧啶基、吡嗪基、哒嗪基、噁唑基、异噁唑基、噻唑基、异噻唑基、1,2,4-噁二唑、1,3,4-噁二唑、1,2,4-噻二唑或1,3,4-噻二唑； R 1 is selected from unsubstituted or substituted by 1-5 R 8 pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1, 2, 4-oxadiazole, 1,3,4-oxadiazole, 1,2,4-thiadiazole or 1,3,4-thiadiazole;
    R 2选自H、C 1-C 3烷基； R 2 is selected from H, C 1 -C 3 alkyl;
    R 3选自H、C 1-C 4烷基； R 3 is selected from H, C 1 -C 4 alkyl;
    R 4与R 5相同或不同选自H、卤素、C 1-C 3烷基； R 4 and R 5 are the same or different and are selected from H, halogen, C 1 -C 3 alkyl;
    R 6、R 7相同或不同的分别选自氢、C 1-C 3烷基； R 6 and R 7 that are the same or different are selected from hydrogen and C 1 -C 3 alkyl groups;
    其中，R 6、R 7还可以与其相连的N组成含C、N、O或S的三元、四元、五元或六元杂环烷烃； Among them, R 6 , R 7 can also be connected to the N to form a three-membered, four-membered, five-membered or six-membered heterocycloalkane containing C, N, O or S;
    R 8选自H、卤素、羟基、氨基、硝基、氰基、C 1-C 3烷基、卤代C 1-C 3烷基、C 1-C 3烷氧基、卤代C 1-C 3烷氧基、C 3-C 4环烷基、NR 6R 7、C(＝O)NR 6R 7、C 1-C 3烷基羰基、C 1-C 3烷氧基羰基、卤代C 1-C 3烷氧基羰基、C 1-C 3烷基羰基氧基、卤代C 1-C 3烷基羰基氧基、C 1-C 3烷基磺酰基氧基、卤代C 1-C 3烷基磺酰基氧基、C 1-C 3烷氧基C 1-C 3烷氧基或卤代C 1-C 3烷氧基C 1-C 3烷氧基。 R 8 is selected from H, halogen, hydroxyl, amino, nitro, cyano, C 1 -C 3 alkyl, halo C 1 -C 3 alkyl, C 1 -C 3 alkoxy, halo C 1- C 3 alkoxy, C 3 -C 4 cycloalkyl, NR 6 R 7 , C(=O)NR 6 R 7 , C 1 -C 3 alkylcarbonyl, C 1 -C 3 alkoxycarbonyl, halogen Substituted C 1 -C 3 alkoxycarbonyl group, C 1 -C 3 alkylcarbonyloxy group, halogenated C 1 -C 3 alkylcarbonyloxy group, C 1 -C 3 alkylsulfonyloxy group, halogenated C 1 -C 3 alkylsulfonyloxy, C 1 -C 3 alkoxy C 1 -C 3 alkoxy or halogenated C 1 -C 3 alkoxy C 1 -C 3 alkoxy.
  5. 按权利要求4的三唑衍生物，其特征在于：所述三唑衍生物为通式I所示化合物、其非对映异构体、手性异构体或其盐：The triazole derivative according to claim 4, characterized in that: the triazole derivative is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
    式中Where
    R 1选自未取代或被1-5个R 8取代的5-吡啶基、2-吡啶基、5-嘧啶基、2-嘧啶基、2-吡嗪基、2-哒嗪基、5-噁唑基、4-噁唑基、5-异噁唑基、3-异噁唑基、5-噻唑基、4-噻唑基、5-异噻唑基、3-异噻唑基、 3-1,2,4-噁二唑、5-1,2,4-噁二唑、5-1,3,4-噁二唑、3-1,2,4-噻二唑、5-1,2,4-噻二唑或5-1,3,4-噻二唑； R 1 is selected unsubstituted or substituted with 1-5 R 8 5-pyridyl, 2-pyridyl, 5-pyrimidinyl, 2-pyrimidinyl, 2-pyrazinyl, 2-pyridazinyl, 5- Oxazolyl, 4-oxazolyl, 5-isoxazolyl, 3-isoxazolyl, 5-thiazolyl, 4-thiazolyl, 5-isothiazolyl, 3-isothiazolyl, 3-1, 2,4-oxadiazole, 5-1,2,4-oxadiazole, 5-1,3,4-oxadiazole, 3-1,2,4-thiadiazole, 5-1,2, 4-thiadiazole or 5-1,3,4-thiadiazole;
    R 2选自H、甲基； R 2 is selected from H, methyl;
    R 3选自叔丁基； R 3 is selected from tert-butyl;
    R 4与R 5相同或不同选自H、甲基； R 4 and R 5 are the same or different and are selected from H and methyl;
    R 8选自H、卤素、硝基、氰基、甲基、三氟甲基、甲氧基、三氟甲氧基、二甲氨基、甲基羰基、甲氧基羰基、甲基羰基氧基、三氟甲基羰基氧基、甲基磺酰基氧基、甲氧基乙氧基或乙氧基乙氧基。 R 8 is selected from H, halogen, nitro, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy, dimethylamino, methylcarbonyl, methoxycarbonyl, methylcarbonyloxy , Trifluoromethylcarbonyloxy, methylsulfonyloxy, methoxyethoxy or ethoxyethoxy.
  6. 按权利要求5的三唑衍生物，其特征在于：三唑衍生物为通式I所示化合物、其非对映异构体、手性异构体或其盐：The triazole derivative according to claim 5, characterized in that: the triazole derivative is a compound represented by formula I, its diastereomers, chiral isomers or salts thereof:
    R 1选自2-R 8-5-吡啶基、5-R 8-2-吡啶基、2-R 8-5-嘧啶基、5-R 8-2-嘧啶基、2-R 8-5-吡嗪基、2-R 8-6-哒嗪基、2-R 8-5-噁唑基、2-R 8-4-噁唑基、3-R 8-5-异噁唑基、5-R 8-3-异噁唑基、2-R 8-5-噻唑基、2-R 8-4-噻唑基、3-R 8-5-异噻唑基、5-R 8-3-异噻唑基、5-R 8-3-1,2,4-噁二唑、3-R 8-5-1,2,4-噁二唑、2-R 8-5-1,3,4-噁二唑、5-R 8-3-1,2,4-噻二唑、3-R 8-5-1,2,4-噻二唑或2-R 8-5-1,3,4-噻二唑； R 1 is selected from 2-R 8 -5-pyridyl, 5-R 8 -2-pyridyl, 2-R 8 -5-pyrimidinyl, 5-R 8 -2-pyrimidinyl, 2-R 8 -5 -Pyrazinyl, 2-R 8 -6-pyridazinyl, 2-R 8 -5-oxazolyl, 2-R 8 -4-oxazolyl, 3-R 8 -5-isoxazolyl, 5-R 8 -3-isothiazolyl, 2-R 8 -5-thiazolyl, 2-R 8 -4-thiazolyl, 3-R 8 -5-isothiazolyl, 5-R 8 -3- Isothiazolyl, 5-R 8 -3-1,2,4-oxadiazole, 3-R 8 -5-1,2,4-oxadiazole, 2-R 8 -5-1,3,4 -Oxadiazole, 5-R 8 -3-1,2,4-thiadiazole, 3-R 8 -5-1,2,4-thiadiazole or 2-R 8 -5-1,3, 4-thiadiazole;
    R 2选自H； R 2 is selected from H;
    R 3选自叔丁基； R 3 is selected from tert-butyl;
    R 4与R 5选自H； R 4 and R 5 are selected from H;
    R 8选自卤素、甲氧基。 R 8 is selected from halogen and methoxy.
  7. 按权利要求6的三唑衍生物，其特征在于：三唑衍生物为通式I所示化合物、其非对映异构体、手性异构体或其盐：The triazole derivative according to claim 6, characterized in that: the triazole derivative is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
    式中，Where
    R 1选自2-R 8-5-吡啶基、5-R 8-2-吡啶基、2-R 8-5-嘧啶基、2-R 8-5-吡嗪基、2-R 8-6-哒嗪基或2-R 8-5-噻唑基； R 1 is selected from 2-R 8 -5-pyridyl, 5-R 8 -2-pyridyl, 2-R 8 -5-pyrimidinyl, 2-R 8 -5-pyrazinyl, 2-R 8- 6-pyridazinyl or 2-R 8 -5-thiazolyl;
    R 2选自H； R 2 is selected from H;
    R 3选自叔丁基； R 3 is selected from tert-butyl;
    R 4与R 5选自H； R 4 and R 5 are selected from H;
    R 8选自氯、溴、甲氧基。 R 8 is selected from chlorine, bromine and methoxy.
  8. 按权利要求7的三唑衍生物，其特征在于：所述三唑衍生物为通式I所示化合物、其非对映异构体、手性异构体或其盐：The triazole derivative according to claim 7, characterized in that: the triazole derivative is a compound represented by general formula I, its diastereomers, chiral isomers or salts thereof:
    式中，Where
    R 1选自2-R 8-5-吡啶基； R 1 is selected from 2-R 8 -5-pyridyl;
    R 2选自H； R 2 is selected from H;
    R 3选自叔丁基； R 3 is selected from tert-butyl;
    R 4与R 5选自H； R 4 and R 5 are selected from H;
    R 8选自氯、溴、甲氧基。 R 8 is selected from chlorine, bromine and methoxy.
  9. 一种权利要求1-8任意一项所述的三唑衍生物在用于制备植 物生长调节剂或杀菌剂。A triazole derivative according to any one of claims 1-8 is used in the preparation of plant growth regulators or fungicides.
  10. 按权利要求8所述的应用，其特征在于，以权利要求1-7任意一项所述三唑衍生物作为活性组分在用于制备植物生长调节剂或杀菌剂中的应用；所述活性组分的重量百分含量为0.1-99％。The use according to claim 8, characterized in that the triazole derivative of any one of claims 1-7 is used as an active ingredient in the preparation of plant growth regulators or fungicides; the activity The weight percentage of the components is 0.1-99%.
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