WO2019080225A1 - Composé de pyrazolone ou sel de celui-ci, composition herbicide et utilisation - Google Patents

Composé de pyrazolone ou sel de celui-ci, composition herbicide et utilisation

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Publication number
WO2019080225A1
WO2019080225A1 PCT/CN2017/112013 CN2017112013W WO2019080225A1 WO 2019080225 A1 WO2019080225 A1 WO 2019080225A1 CN 2017112013 W CN2017112013 W CN 2017112013W WO 2019080225 A1 WO2019080225 A1 WO 2019080225A1
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WIPO (PCT)
Prior art keywords
group
alkyl
alkoxy
phenyl
halogen
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PCT/CN2017/112013
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English (en)
Chinese (zh)
Inventor
连磊
征玉荣
何彬
彭学岗
金涛
崔琦
Original Assignee
青岛清原化合物有限公司
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Publication of WO2019080225A1 publication Critical patent/WO2019080225A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D403/10—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 aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Definitions

  • the present application belongs to the field of pesticides, and in particular relates to a pyrazolone compound or a salt thereof, a herbicide composition and use thereof.
  • Patent CN105218449A and the like disclose a series of herbicidal pyrazolone herbicide compounds and a synthesis method thereof.
  • the present invention synthesizes a novel class of pyrazolone compounds having a novel structure and herbicidal activity.
  • the medicinal active substance provided by the invention has good pharmacological effect, convenient use and low cost.
  • R 1 R 2 N stands for among them
  • R a is selected from one or more of the following groups: hydrogen, halogen, cyano, nitro, hydroxy, carboxy, amino, C 1 -C 6 alkylsulfonyl, C 1-6 alkyl, halo C 1 to 6 alkyl, C 2 to 6 alkenyl, halogenated C 2 to 6 alkenyl, C 1 to 6 alkoxy, halo C 1-6 alkoxy, C 1-6 alkylamino, C 2-6 alkenyloxy, halo C 2-6 alkenyloxy, C 2-6 alkenylamino, halogenated C 2-6 alkenylamino, C 1-6 alkylcarbonyl, halogenated C 1-6 alkylcarbonyl a C 1-6 alkoxycarbonyl group, a C 1-6 alkylaminocarbonyl group, a C 1-6 alkoxy C 1-6 alkyl group, a halogenated C 1-6 alkoxy C 1-6 alkyl group, C 1 ⁇
  • R b is selected from the group consisting of hydrogen, C 1-6 alkyl, halogenated C 1-6 alkyl, C 2-6 alkenyl, halogenated C 2-6 alkenyl, C 1-6 alkoxy C 1-6 alkane , halogenated C 1-6 alkoxy C 1-6 alkyl, C 1-6 alkylcarbonyl, halogenated C 1-6 alkylcarbonyl, C 1-6 alkylsulfonyl, C 1-6 alkane Oxycarbonyl group, C 1-6 alkylaminocarbonyl group, C 1-6 alkylcarbonyl C 1-6 alkyl group, C 1-6 alkoxycarbonyl C 1-6 alkyl group, C 1-6 alkylaminocarbonyl C 1 ⁇ 6 alkyl, unsubstituted or 1-3 independently selected from halogen, nitro, cyano, C 1-6 alkyl, halogenated C 1-6 alkyl, C 1-6 alkoxy, halogen An aryl
  • R 3 represents hydrogen, C 1-4 alkyl, C 2 to 4 alkenyl, C 2 to 4 alkynyl, unsubstituted or C 3 to 6 cycloalkyl substituted with C 1-4 alkyl;
  • R 4 represents a methyl group, an ethyl group, a n-propyl group, an isopropyl group or a cyclopropyl group;
  • R 5 , R 6 represents a substituted or unsubstituted C 1-6 alkyl, aryl or heterocyclic group, and n represents 1, 2, 3;
  • R 7 represents a substituted or unsubstituted aryl or heterocyclic group, halogen, C 1-6 alkylamino, C 2 to 4 alkynyl, C 2 to 4 alkenyl, C 1-6 alkoxy, nitro, Cyano group, C 3-6 cycloalkyl group, amino group, C 1-6 alkylthio group;
  • R 8 represents C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylamino, C 1-6 alkylthio, C 1-6 alkylamino C 1-6 alkyl, C 1 ⁇ 6 alkylthio C 1-6 alkyl, halogen, amino, cyano, nitro, C 1-6 alkoxy C 1-6 alkyl, substituted or unsubstituted phenyl, phenyl C 1-6 An alkyl group, a phenoxy group, a phenoxy C 1-6 alkyl group or a heterocyclic group;
  • R 9 represents hydrogen, C 1-6 alkyl, C 3-6 cycloalkyl, substituted or unsubstituted phenyl or heterocyclic.
  • R 5 and R 6 represent an unsubstituted C 1-6 alkyl group, a phenyl group or a 3- to 10-membered heterocyclic group having 1 to 4 hetero atoms selected from O, N and S, selected from C.
  • 1 to 6 alkyl C 1-6 alkoxy, C 1-6 alkylamino, C 1-6 alkylthio, halogen, C 2 to 4 alkenyl, C 2 to 4 alkynyl, amino, nitro , cyano group, carboxyl group, C 1-6 alkoxycarbonyl group, C 1-6 alkoxy C 1-6 alkyl group, C 1-6 alkylsulfonyl C 1-6 alkyl group, C 1-6 alkyl sulfide arylsulfonyl group C 1 ⁇ 6 alkyl group, C 3 ⁇ 6 cycloalkyl group one or more groups substituted C 1 ⁇ 6 alkyl group, or a phenyl group containing 1 to 4 heteroatoms selected from O, N and S a heterocyclic 3 to 10 membered heterocyclic group, and n represents 1, 2, and 3;
  • R 7 represents an unsubstituted phenyl group or a 3- to 10-membered heterocyclic group having 1 to 4 hetero atoms selected from O, N and S, and is selected from a C 1-6 alkyl group and a C 1-6 alkoxy group.
  • R 8 represents C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylamino, C 1-6 alkylthio, C 1-6 alkylamino C 1-6 alkyl, C 1 ⁇ 6 alkylthio C 1-6 alkyl, halogen, amino, cyano, nitro, C 1-6 alkoxy C 1-6 alkyl, phenyl, phenyl C 1-6 alkyl, phenoxy a phenoxy-C 1-6 alkyl group or a 3- to 10-membered heterocyclic group having 1 to 4 hetero atoms selected from O, N and S, selected from C 1 to 6 alkyl groups, C 1 to 6 Alkoxy, C 1-6 alkylamino, C 1-6 alkylthio, halogen, C 2 to 4 alkenyl, C 2 to 4 alkynyl, amino, nitro, cyano, carboxy, C 1-6 Alkoxycarbonyl group, C 1-6 alkoxy C 1-6 alkyl group, C 1-6
  • R 9 represents hydrogen, C 1-6 alkyl, C 3-6 cycloalkyl, unsubstituted phenyl or a 3 to 10 membered heterocyclic group containing 1 to 4 hetero atoms selected from O, N and S, Is selected from the group consisting of C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylamino, C 1-6 alkylthio, halogen, C 2 to 4 alkenyl, C 2 to 4 alkynyl, Amino, nitro, cyano, carboxyl, C 1-6 alkoxycarbonyl, C 1-6 alkoxy C 1-6 alkyl, C 1-6 alkylsulfonyl C 1-6 alkyl, C 1 a phenyl group substituted with one or more groups of a 6 alkylthiosulfonyl C 1-6 alkyl group or a C 3 -6 cycloalkyl group or a hetero atom having 1 to 4 selected from O, N and S a
  • Het is selected from
  • R 3 represents hydrogen, methyl, ethyl, cyclopropyl
  • R 4 represents a methyl group, an ethyl group, an isopropyl group
  • R 5 and R 6 represent an unsubstituted C 1-6 alkyl group, a phenyl group or a 3- to 10-membered aromatic heterocyclic group having 1 to 4 hetero atoms selected from O, N and S, and are selected from C 1 to 6 alkyl, C 1 to 6 alkoxy, halogen, one or more groups substituted C 1 ⁇ 6 alkyl group, or a phenyl group containing 1 to 4 heteroatoms selected from O, N and S heteroatoms 3 to 10 membered aromatic heterocyclic group, n represents 2;
  • R 7 represents an unsubstituted phenyl group or a 3- to 10-membered aromatic heterocyclic group having 1 to 4 hetero atoms selected from O, N and S, and is selected from a C 1-6 alkyl group and a C 1-6 alkoxy group.
  • R 8 represents C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylamino, C 1-6 alkylthio, C 1-6 alkylamino C 1-6 alkyl, C 1 ⁇ 6 alkylthio C 1-6 alkyl, phenyl, phenyl C 1-6 alkyl, phenoxy, phenoxy C 1-6 alkyl or 1-4 selected from O, N and S
  • the heterocyclic 3- to 10-membered aromatic heterocyclic group is selected from the group consisting of C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylamino, C 1-6 alkylthio, halogen, C.
  • R 9 represents hydrogen, C 1-6 alkyl, C 3-6 cycloalkyl, unsubstituted phenyl or a 3 to 10 membered heterocyclic group containing 1 to 4 hetero atoms selected from O, N and S. is selected from substituted C 1 ⁇ 6 alkyl group, C 1 ⁇ 6 alkoxy, halogen or one or more phenyl groups containing 1 to 4 heteroatoms selected from O, N and S, 3 to 10 membered aromatic heterocyclic group.
  • heterocycle denotes a 3 to 10 membered aromatic or non-aromatic heterocyclic ring containing from 1 to 4 heteroatoms selected from O, N and S and having a lactone, cyclic ether, lactam structure.
  • a 4 to 10 membered cyclic compound and includes a bicyclic group.
  • heterocyclyl includes “arylheterocyclyl” as well as dihydro or tetrahydro analogs thereof.
  • the heterocyclic substituent may be bonded via a carbon atom or a hetero atom.
  • aromatic heterocyclic group denotes a stable monocyclic or bicyclic ring which may be up to 7 atoms in each ring, which may include one aromatic ring and contain from 1 to 4 heteroatoms selected from O, N and S.
  • Aromatic heterocyclic groups within the scope of this definition include, but are not limited to, acridinyl, oxazolyl, porphyrin, quinoxalinyl, pyrazolyl, indolyl, benzotriazolyl, thienyl, furan Benzo, benzothienyl, benzofuranyl, quinolyl, isoquinolyl, oxazolyl, isoxazolyl, indolyl, pyrazinyl, pyridazinyl, pyridyl, pyrimidinyl, pyrrolyl , tetrahydroquinolyl, thiazolyl, imidazolyl, triazolyl, oxadiazolyl, thiadiazolyl, triazinyl, as defined by a heterocyclic ring, "aromatic heterocyclic” is also understood to include any An N-oxide derivative of a nitrogen-containing aromatic heterocyclic group.
  • the salt is an agrochemically acceptable salt, preferably an acid addition salt obtained by reacting a compound of this type with a chemically acceptable acid, or a hydroxypyrazole compound and a base having an acidic group therein A salt formed by the reaction of a compound.
  • the acid is preferably selected from the group consisting of inorganic acids (such as hydrochloric acid, sulfuric acid, phosphoric acid or hydrobromic acid) and organic acids (such as oxalic acid, maleic acid, fumaric acid, malic acid, tartaric acid, citric acid or benzene).
  • the basic compound is preferably selected from the group consisting of sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate or potassium hydrogencarbonate.
  • the above pharmaceutically acceptable salts are easily separated and can be purified by conventional separation methods such as solvent extraction, dilution, recrystallization, column chromatography, and preparative thin layer chromatography.
  • a method of preparing the pyrazolone compound or a salt thereof comprising the steps of:
  • A represents a hydroxyl group, a halogen, a methylsulfonyl group or a p-toluenesulfonyl group, and the reaction equation is as follows:
  • the steps (1) and (2) are carried out in an aprotic solvent under the action of a base; the reaction temperature is from -30 ° C to 180 ° C, preferably from -5 ° C to 90 ° C.
  • the solvent is acetonitrile, diethyl ether, tetrahydrofuran, DMF or DMSO, preferably acetonitrile, tetrahydrofuran or DMF;
  • the base is sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate , triethylamine, DIPEA or DBU, preferably NaH, triethylamine or potassium carbonate.
  • the compound of the formula II can be obtained by the following reaction:
  • step (1) of preparing the compound of the formula III may also be carried out by the following reaction:
  • the compound of the formula I can also be prepared in the step (2) by the following method:
  • B represents halogen and M represents an alkali metal, an alkaline earth metal, or the like.
  • the compound containing SO and SO 2 in Het can be obtained by controlling the degree of oxidation of the corresponding S-containing compound by a conventional oxidation step, and the oxidizing agent used includes, but not limited to, NaClO and a peroxide such as mCPBA or peracetic acid.
  • a herbicidal composition comprising a herbicidally effective amount of at least one of the pyrazolone compound or a salt thereof.
  • the herbicidal composition also includes a formulation aid.
  • a method of controlling a harmful plant which comprises using a herbicidally effective amount of at least one of the pyrazolone compound or a salt thereof or the herbicidal composition described above on a plant or a harmful plant area.
  • the compounds of formula I of the present invention have outstanding herbicidal activity.
  • the active substances of the present invention are also effective for perennial weeds which grow from rhizomes, rhizomes, or other perennial organs and are difficult to control. In this regard, it is generally not important to use the substance before, before, or after germination. Particular mention is made of representative examples of monocotyledonous and dicotyledonous weed populations which can be controlled by the compounds of the invention, without limiting the identified species.
  • weed species in which the active substance is effective include monocotyledons: annual oats, rye, grasses, maiden, ferraris, medlar, genus, foxtail, and sedge, and perennial ice. Genus, Bermudagrass, Rhizoma and sorghum, and perennial sedge.
  • dicotyledonous weed species species whose effects can be extended to, for example, the annual genus Polyporus, Amaranth, Pomna, Wild Sesame, Stellaria, Amaranthus, White Mustard, Ipomoea, and Yellow Flower Genus, Matricaria and genus, and perennial weeds, genus, genus and genus.
  • the active substance of the present invention effectively controls harmful plants under the conditions of rice sowing, such as cockroaches, genus, genus, genus, genus, cane, and sedge.
  • the compound of the present invention is applied to the surface of the soil before germination, the weeds of the weeds can be completely prevented before the weeds grow, or when the weeds grow out of the cotyledons, and finally completely die after three to four weeks.
  • the compound of the present invention is particularly resistant to the following plants, and is active in the following plants, such as Apila, Xiaoye Sesame, Rolling Stalk, Poria, Ivy, Herba, Arabian, Pansy, Pansy, Poria and Kochia. .
  • the compounds of the present invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, there is no damage to important economic crop plants such as wheat, barley, rye, rice, corn, sugar beet, cotton and soybean. Or the damage is trivial. In particular, it is well compatible with cereal crops such as wheat, barley and corn, especially wheat. Thus, the compounds of the invention are highly suitable for the selective control of unwanted plants in agricultural or ornamental plants.
  • Transgenic plants Due to their herbicidal nature, these active substances can be used to control harmful plants in genetically engineered plant cultivation that is known or to be present.
  • Transgenic plants generally have superior traits, such as resistance to specific insecticides, particularly specific herbicides, resistance to pathogenic microorganisms of plant diseases or plant diseases, such as specific insect or fungal, bacterial or viral microorganisms.
  • Other specific traits are related to the following conditions of the product, such as quantity, quality, storage stability, composition and specific ingredients.
  • the obtained transgenic plant product has an increased starch content or an improved starch quality or a different fatty acid composition.
  • the compounds of the formula I according to the invention or their salts are preferably used in economically important transgenic crops and ornamental plants, such as cereals, such as wheat, barley, rye, oats, millet, rice, cassava and corn, or for beets, Cultivation of cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetable plants.
  • the compounds of the formula I are preferably used as herbicides for the cultivation of useful plants which are resistant or resistant to the toxic effects of the herbicide by genetic engineering.
  • glufosinate herbicides eg EP-0242236 A, EP-0242246 A
  • glyphosate herbicides WO 92/00377
  • sulfonate An ureide herbicide EP-0257993 A, US-5013659 A
  • transgenic crop plant such as cotton which is capable of producing a Bacillus thuringiensis toxin (Bt toxin) which protects against damage by a particular pest (EP-0142924 A, EP-0193259 A);
  • Plant cells of the activity-reducing gene product can be prepared by, for example, expressing at least one appropriate antisense-RNA, sense-RNA to achieve co-suppression, or by expressing at least one appropriately constructed ribozyme, It specifically cleaves the transcription product of the above gene product.
  • DNA molecules comprising the entire coding sequence of the gene product, including any flanking sequences that may be present, and the use of DNA molecules comprising only a portion of the coding sequence, which must be sufficiently long to achieve antisense in the cell Effect. Sequences that are highly homologous but not identical to the gene product coding sequence can also be used.
  • the synthesized protein can be localized in any desired plant cell compartment.
  • the synthesized protein can be localized in any desired plant cell compartment.
  • These sequences are known to those skilled in the art (see, for example, Braun et al, EMBO J. 11 (1992) 3219-3227; Wolter et al, Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al. Plant J. 1 (1991), 95-106).
  • Transgenic plant cells can be recombined into whole plants using known techniques.
  • the control can be improved or expanded.
  • the range of weeds, the application rate at the time of application is preferably a combination of the resistance of the transgenic crops and the performance of the herbicide, and the effects of the growth and yield of the transgenic crop plants.
  • the invention therefore also provides the use of said compounds as herbicides to control harmful plants in plants of transgenic crops.
  • the compounds of the invention can significantly modulate the growth of crop plants. By modulating the involvement of plant metabolism, these compounds are used to orient the components of the plant and promote harvesting, such as drying and dwarfing the plants. Moreover, they are also suitable for regulating and inhibiting unwanted plant growth without destroying the growth of the crop. Inhibition of plant growth plays a very important role in many monocotyledonous and dicotyledonous crops, as this reduces or completely prevents lodging.
  • the compound of the present invention can be applied using a general formulation, and a wettable powder, a concentrated emulsion, a sprayable solution, a powder or granules can be used.
  • a herbicidal composition comprising a compound of formula I.
  • the compounds of formula I can be formulated in a variety of ways, depending on the usual biological and/or chemical physical parameters.
  • suitable formulations are: wettable powders (WP), water soluble powders (SP), water soluble concentrates, concentrated emulsions (EC), emulsions such as oil dispersed in water and water dispersed in oil (EW) , sprayable solution, suspension concentrate (SC), dispersible oil suspension (OD), oil or water diluent, solution of miscible oil, powder (DP), capsule suspension (CS) ), seed dressing composition, particles for spreading and soil application, sprayed particles, coated particles and absorbent particles, water dispersible particles (WG), water soluble particles (SG), ULV (super Low volume) formula, microcapsules and wax products.
  • WP wettable powders
  • SP water soluble powders
  • EC concentrated emulsions
  • EW oil dispersed in water and water dispersed in oil
  • SC sprayable solution, suspension concentrate
  • OD dispersible oil suspension
  • DP powder
  • Wettable powders can be uniformly dispersed in water, in addition to active substances, including diluents or inert substances, ionic and nonionic surfactants (wetting agents, dispersing agents), such as polyethoxylated alkylphenols, poly Ethoxylated fatty alcohol, polyoxyethyl aliphatic amine, fatty alcohol polyglycol ether sulfate, alkyl sulfonate, alkyl phenyl sulfonate, sodium lignosulfonate, 2, 2'- dinaphthylmethane Sodium 6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoylmethyltaurate.
  • the herbicide active substance is finely ground, for example, using a conventional apparatus such as a hammer mill, a fan mill and a jet mill, and an auxiliary agent is simultaneously or sequentially mixed.
  • a concentrated emulsion such as butanol, cyclohexanone, dimethylformamide, xylene or a higher boiling aromatic compound or a mixture of hydrocarbons or solvents, and adding one more One or more ionic and/or nonionic surfactants (emulsifiers).
  • emulsifiers which can be used are, for example, calcium alkylaryl sulfonates of calcium dodecylbenzene sulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkyl aromatic polyglycol ethers, fatty alcohols Polyglycol ether, propylene oxide-ethylene oxide condensation product, alkyl polyether, sorbitan ester such as sorbitan fatty acid ester, or polyoxyethylene sorbent such as polyoxyethylene sorbitan fatty ester A glycan ester.
  • nonionic emulsifiers such as fatty acid polyglycol esters, alkyl aromatic polyglycol ethers, fatty alcohols Polyglycol ether, propylene oxide-ethylene oxide condensation product, alkyl polyether, sorbitan ester such as sorbitan fatty acid ester, or polyoxyethylene sorbent such as polyoxyethylene sorbitan fatty ester A gly
  • the active substance and the finely divided solid matter are ground to obtain a powder, a solid substance such as talc, a natural clay such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • a water or oil based suspension can be prepared by, for example, wet milling using a commercially available bead mill with or without the addition of a surfactant of the other formulation type described above.
  • an aqueous organic solvent may be used, using a stirrer, a colloid mill and/or a static mixer, and if necessary, a surfactant of another formulation type as described above may be added.
  • the granules are prepared by spraying the active material onto the adsorbate, granulating with an inert material, or concentrating the active material onto the surface of, for example, a sand or kaolinite carrier, granulating the inert material by a binder, and adhering Mixtures such as polyvinyl alcohol, sodium polyacrylate or mineral oil.
  • Suitable actives can be plasmidized by the method of preparing fertilizer granules, and if necessary, fertilizer can be mixed.
  • the water-suspended granules are prepared by a usual method such as spray-drying, fluidized bed granulation, disc granulation, mixing using a high speed mixer, and extrusion without a solid inert material.
  • the agrochemical formulations usually comprise from 0.1 to 99% by weight, in particular from 0.1 to 95%, of the active substance I.
  • the concentration of the active substance in the wettable powder is, for example, from about 10 to 99% by weight, and the usual formulation components constitute the remaining amount by weight to 100%.
  • the concentration of the active substance in the concentrated emulsion may range from about 1 to 90%, preferably from 5 to 80% by weight.
  • the powder formulation comprises from 1 to 30% by weight of active substance, usually from 5 to 20% by weight of active substance, whereas the sprayable solution comprises from about 0.05 to 80%, preferably from 2 to 50% by weight of active substance. .
  • the content of the active material in the water-suspended granules mainly depending on whether the active material is liquid or solid, and auxiliaries, fillers and the like used in granulation.
  • the content of the active substance in the aqueous suspension granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the preparation of the active substance may include a tackifier, a wetting agent, a dispersing agent, an emulsifier, a penetrating agent, a preservative, an antifreezing agent, a solvent, a filler, a carrier, a coloring agent, an antifoaming agent, an evaporation inhibitor, and pH and viscosity modifiers commonly used in all cases.
  • insecticide active substances such as insecticides, acaricides, herbicides and fungicides, or with safeners, fertilizers and/or plant growth regulators.
  • safeners for premixed or filled mix.
  • Suitable active substances which can be mixed with the active substance of the present invention in a mixed preparation or a tank mix are, for example, "World Pesticide New Variety Technology Encyclopedia", China Agricultural Science and Technology Press, 2010.9 and the literature cited herein.
  • the herbicide active substance mentioned below may be mixed with the mixture of the formula I (note: the name of the compound, or a common name according to the International Organization for Standardization (ISO), or a chemical name, if appropriate, a code): Amine, butachlor, alachlor, propisochlor, metolachlor, stilben, acetochlor, chlorfenapyr, acetochlor, naproxen, R-levoperin Acetochlor, dipivoxil, thiaceuramide, dibenzoylamine, piracetamide, herbicide, flufenic acid, bromobutyramide, dimethoprim, high-efficiency dimethyl Thiamethoxazole, acetophene, flufenacet,
  • the commercially available formulations are diluted in a conventional manner, for example, in wettable powders, concentrated emulsions, suspensions, and granules suspended in water, diluted with water.
  • Granules for granules or soil application or sprayed and sprayed solutions are generally not required to be further diluted with inert materials prior to use.
  • the amount of the compound of formula I required varies with external conditions, such as temperature, humidity, the nature of the herbicide used, and the like. It can have a large range of variation, for example between 0.001 and 1.0 kg/ha, or more active substance, but preferably between 0.005 and 750 g/ha, in particular between 0.005 and 250 g/ha.
  • the activity level criteria for harmful plant damage are as follows:
  • Grade 9 growth control rate is above 95%
  • Level 7 growth control rate is above 80%
  • Level 5 The growth control rate is above 60%
  • Level 2 growth control rate is 5-20%
  • Level 1 The growth control rate is below 5%
  • the above growth control rate is the fresh weight control rate.
  • the application dose is 250 g/ha of active ingredient and the water exchange rate is 450 kg/ha.
  • the paddy soil After filling the paddy soil in a 1/1,000,000 hectare tank, seeds of valerian, sorghum, and ragweed are planted, and the soil is gently covered thereon. Thereafter, it is placed in a greenhouse at a depth of 0.5-1 cm, and the water storage depth is 3-4 cm, and 1.5 leaves are obtained in the valerian, the ginseng, and the ragweed, and the present invention is prepared according to the usual preparation method.
  • the wettable powder of the compound or the aqueous dilution of the suspension is uniformly dripped with a pipette to achieve a predetermined amount of active ingredient.
  • the transplanting depth was 3 cm to transplant the rice (japan) in the 3 leaf stage.
  • the compound of the present invention was treated in the same manner as above on the fifth day after transplantation.
  • the fertility status of valerian, Qianjin, and ragweed on the 14th day after treatment with the naked eye was observed with the naked eye.
  • the fertility status of the rice for 21 days was evaluated by the activity standard level of 0-10, and the results of Table 3 were obtained.
  • valerian, Qianjin, and ragweed were collected from Heilongjiang, China, and tested for resistance to conventional doses of pyrazosulfuron.

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  • Organic Chemistry (AREA)
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Abstract

L'invention concerne un composé de pyrazolone ou un sel de celui-ci, une composition herbicide et une utilisation. Le composé de pyrazolone est représenté par la formule générale I : dans laquelle R1R2N représente, Het est choisi parmi un cycle hétérocyclique à cinq ou six chaînons qui contient non seulement un atome C, N en position 1, et un ou deux C=O, mais contient également de 1 à 3 atomes ou groupes suivants servant de composants de cycle : O, NRb, S, SO, et SO2; lorsque Het est un cycle hétérocyclique à six chaînons qui n'a qu'un C=O en position 2, la position 4 ne peut pas être O, NRb ou S; R3 représente l'hydrogène, un alkyle en C1-4 ou similaire; R4 représente méthyle, éthyle ou similaire; X représente l'hydrogène, -R5, -S(O)nR6, -CH2R7, -(C=O)R8, -PO(OR9)2, -Si(OR9)3, ou similaire.
PCT/CN2017/112013 2017-10-24 2017-11-21 Composé de pyrazolone ou sel de celui-ci, composition herbicide et utilisation WO2019080225A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1409710A (zh) * 1999-12-02 2003-04-09 巴斯福股份公司 环丙基稠合的3－(4,5－二氢异噁唑－3－基)－取代的苯甲酰基吡唑
CN103980202A (zh) * 2014-05-27 2014-08-13 青岛清原化合物有限公司 一种具有除草活性的4-苯甲酰吡唑类化合物
CN105218449A (zh) * 2015-11-06 2016-01-06 青岛清原化合物有限公司 吡唑酮类化合物或其盐、制备方法、除草剂组合物及用途

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE310739T1 (de) * 1995-02-24 2005-12-15 Pyrazol-4-yl-benzoylderivate und ihre verwendung als herbizide
US6165944A (en) * 1997-01-17 2000-12-26 Basf Aktiengesellschaft 4-(3-heterocyclyl-1-benzoyl) pyrazoles and their use as herbicides
EP1003736B1 (fr) * 1997-08-07 2006-04-12 Basf Aktiengesellschaft 4-benzoyl-pyrazoles substitues

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1409710A (zh) * 1999-12-02 2003-04-09 巴斯福股份公司 环丙基稠合的3－(4,5－二氢异噁唑－3－基)－取代的苯甲酰基吡唑
CN103980202A (zh) * 2014-05-27 2014-08-13 青岛清原化合物有限公司 一种具有除草活性的4-苯甲酰吡唑类化合物
CN105218449A (zh) * 2015-11-06 2016-01-06 青岛清原化合物有限公司 吡唑酮类化合物或其盐、制备方法、除草剂组合物及用途

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