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WO2019233372A1 - Composé de pyrazolyl pyrazole de sulfonamide substitué ou sel à activité pesticide acceptable de celui-ci et utilisation associée - Google Patents

Composé de pyrazolyl pyrazole de sulfonamide substitué ou sel à activité pesticide acceptable de celui-ci et utilisation associée Download PDF

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Publication number
WO2019233372A1
WO2019233372A1 PCT/CN2019/089798 CN2019089798W WO2019233372A1 WO 2019233372 A1 WO2019233372 A1 WO 2019233372A1 CN 2019089798 W CN2019089798 W CN 2019089798W WO 2019233372 A1 WO2019233372 A1 WO 2019233372A1
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Prior art keywords
alkoxy
alkyl
halo
substituted
compound
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Chinese (zh)
Inventor
杨春河
李建国
邢阳阳
王旭
刘明东
马娥
耿丽文
葛家成
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Hailir Pesticides and Chemicals Group Co Ltd
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Hailir Pesticides and Chemicals Group Co Ltd
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    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/22—O-Aryl or S-Aryl esters thereof
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • 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
    • C07D401/14—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 three or more hetero rings
    • 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D405/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Definitions

  • the present invention belongs to the technical field of pesticides, and particularly relates to a substituted pyrazolylpyrazolesulfonamide compound or a salt and composition acceptable as a pesticide, and to these compounds or a salt and composition acceptable as a pesticide.
  • Substituted pyrazole derivatives are known to have herbicidal activity. Related pyrazole derivatives and their herbicidal activity are described in patents published as CN1087342A, CN1161956A, and CN105492443A; a pyridine is described in patent published as CN1073440A The azole-pyrazole compound has herbicidal activity; and sulfonamide-based herbicides are known to have good herbicidal activity, such as the herbicide compounds having a sulfonamide structure described in the patent publications CN1073679A and the publication number CN101485320A.
  • the present invention provides a substituted pyrazolylpyrazolesulfonamide compound or an acceptable salt, composition, and use thereof as a pesticide.
  • the compounds of the above-mentioned pyrazolylpyrazolesulfonamide structure or their acceptable salts as pesticides have higher herbicidal activity than known compounds, and especially have very good herbicidal activity against common weeds in paddy fields.
  • Y represents NH, CH 2 , O, SO 2 or S
  • R 1 represents H, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 1 -C 6 alkylthio, halo C 1 -C 6 alkylthio, C 1 -C 6 alkoxy Radical, halo C 1 -C 6 alkoxy;
  • R 2 represents H, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 1 -C 6 alkylthio, halo C 1 -C 6 alkylthio, C 1 -C 6 alkoxy Radical, halo C 1 -C 6 alkoxy;
  • R 1 and R 2 together form a group-(CH 2 ) m- , where m represents 1-6;
  • R 3 represents H or halogen
  • R 4 represents H, CN, halogen, NO 2 , CONR 1 R 2 ;
  • R 5 represents H or halogen
  • R 6 represents C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 1 -C 6 alkylthio substituted C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo C 1 -C 6 alkoxy or C 1 -C 6 alkoxy substituted C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, halo C 1 -C 6 alkylthio, C 3 -C 6 cycloalkyl, C 3 -C 6 heterocycloalkyl, C 2 -C 6 alkenyl, halo C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, C 2 -C 6 alkenyl Thio, either unsubstituted or 1-5 independently selected from halogen, nitro, cyano, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 1 -C 6 alkoxy Alky
  • R 6 may be selected from C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylthio substituted C 1 -C 6 alkyl.
  • R 1 represents H, C 1 -C 4 alkyl
  • R 2 represents H, C 1 -C 4 alkyl
  • R 1 and R 2 together form a group-(CH 2 ) m- , where m represents 2-4;
  • R 3 represents H or halogen
  • R 4 represents H, CN, halogen, NO 2 , COOR 1 , CONR 1 R 2 ;
  • R 5 represents H or halogen
  • R 6 represents C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylthio substituted C 1 -C 6 alkyl, halo C 1 -C 6 alkylthio, C 3 -C 6 cycloalkyl, C 3 -C 6 heterocycloalkyl, C 2 -C 6 alkenyl, halogenated C 2 -C 6 alkenyl, C 1 -C 6 alkoxy, halo C 1 -C 6 alkoxy or C 1 -C 6 alkoxy substituted C 1 -C 6 alkoxy, or unsubstituted or 1-5 independently selected from halogen , 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 1 -C 6 Alkylcarbonyl
  • R 1 and R 2 together form a group-(CH 2 ) m- , m represents 1-4, and Y represents NH and CH 2 .
  • the aryl group is phenyl and naphthyl
  • the heteroaryl group is thiazole, furan, pyrrole, thiophene, imidazole, pyran, pyridine, pyrazole, pyrimidine, indole, purine , Pyrimidine, pyrazine, pyridazine, triazine, benzothiazole, benzofuran, quinoline, or oxazole.
  • R 1 and R 2 together form a group-(CH 2 ) m- , where m represents 3 or 4;
  • R 3 represents H or halogen
  • R 4 represents H, halogen, CONH 2 or CN
  • R 5 represents H or halogen
  • R 6 represents C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 heterocycloalkyl, C 2 -C 6 alkenyl, C 1 -C 6 alkoxy, halo C 1 -C 6 alkoxy, unsubstituted or 1-5 independently selected from halogen, 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 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkyl Aminocarbonyl, carboxyl, aldehyde, hydroxyl, C 1 -C 6 alkoxy substituted C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 heterocycl
  • Y represents NH
  • R 1 and R 2 together form a group-(CH 2 ) m- , where m represents 3 or 4;
  • R 3 represents H, chlorine or bromine
  • R 4 represents H, CN
  • R 5 represents H
  • R 6 represents C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 heterocycloalkyl, or phenyl, thiazolyl, pyrimidinyl, or is independently selected from halogen , Nitro, cyano, C 1 -C 4 alkyl, halo C 1 -C 4 alkyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl substituted phenyl, thiazolyl, Pyrimidinyl.
  • Y represents NH
  • R 1 and R 2 together form a group-(CH 2 ) m- , where m represents 4;
  • R 3 represents chlorine or bromine
  • R 4 represents CN
  • R 5 represents H
  • R 6 represents methyl, ethyl, propyl, cyclopropanyl, cyclohexane, piperidinyl, or phenyl, pyrimidinyl, or is independently selected from fluorine, chlorine, bromine, methyl, 1-3, Ethyl, propyl, trifluoromethyl, trichloromethyl, methoxycarbonyl, acetyl substituted phenyl groups or 1-3 groups independently selected from fluorine, chlorine, bromine Of pyrimidinyl.
  • C 1 -C 6 alkyl a straight or branched alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl or tert-butyl.
  • Halogen or halogen refers to fluorine, chlorine, bromine, and iodine.
  • Halo C 1 -C 6 alkyl straight or branched alkyl groups having 1 to 6 carbon atoms.
  • the hydrogen atoms on these alkyl groups may be partially or completely replaced by halogens.
  • C 1 -C 6 alkoxy a linear or branched alkyl group having 1 to 6 carbon atoms, connected to the structure via an oxygen atom bond.
  • Halo C 1 -C 6 alkoxy straight or branched chain alkoxy groups having 1 to 6 carbon atoms.
  • the hydrogen atoms on these alkoxy groups may be partially or completely replaced by halogens, for example, chloroform Oxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy, etc.
  • C 1 -C 6 alkylthio A straight or branched alkyl group having 1 to 6 carbon atoms, which is connected to the structure via a sulfur atom bond.
  • Halo C 1 -C 6 alkylthio Linear or branched alkylthio groups having 1 to 6 carbon atoms.
  • the hydrogen atoms on these alkylthio groups may be partially or completely replaced by halogen atoms, for example, chlorine Methylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, and the like.
  • C 1 -C 6 alkoxy-substituted C 1 -C 6 alkoxy a group in which an alkoxy group having 1 to 6 carbon atoms is substituted by an alkoxy group having 1 to 6 carbon atoms Mission, such as
  • C 3 -C 6 heterocyclylamine carbonyl a group formed by linking an amine group obtained by substituting an amino group with a heterocyclic group having 3 to 6 carbon atoms as a substituent, such as
  • C 1 -C 6 alkylcarbonyl A group formed by linking an alkyl group having 1 to 6 carbon atoms with a carbonyl group, such as
  • C 1 -C 6 alkylsulfonyl A group formed by linking an alkyl group having 1 to 6 carbon atoms with a sulfonyl group, such as
  • C 3 -C 6 cycloalkyloxycarbonyl group A group formed by a cycloalkyl group having 3-6 carbon atoms, an oxygen atom, and a carbonyl group connected in sequence, such as
  • Aryl Any functional group or substituent derived from a simple aromatic ring.
  • Heteroaryl a five- or six-membered ring containing one or more N, O, and S heteroatoms, such as pyridine, furan, thiophene, pyrazole, pyrimidine, pyrazine, pyridazine, triazine, quinoline, Thiazole, benzothiazole, benzofuran and the like.
  • Arylamino group An amine group obtained by substituting an amino group with an aryl group as a substituent.
  • Heteroaralkyl An alkyl obtained by substituting a hydrogen of an alkyl group with a heteroaryl group as a substituent.
  • Heteroaryloxy Heteroaryl is connected to an oxygen atom and is connected to the structure via an oxygen atom bond.
  • Paracyclic group a group in which a bicyclic or tricyclic ring is joined together, such as
  • a method for synthesizing a compound described by the general formula I is characterized in that a compound of the general formula II and a compound of the general formula III (in the chemical formulae listed below, unless otherwise defined, the substituents and symbols are the same as those defined in the general formula I And symbol have the same meaning)
  • the product is obtained after the reaction is performed with or without a solvent.
  • the compound represented by general formula II can be synthesized by referring to the method described in patent CN200910092609.5
  • the compound represented by general formula III can be synthesized by referring to the method described in patent CN96116762.9:
  • the solvent is selected from acetonitrile, acetone, methyl ethyl ketone, tetrahydrofuran, ethyl acetate, N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, One or more solvents among one or more solvents of methyl chloride, dichloroethane, chloroform, carbon tetrachloride, toluene, xylene and the like.
  • the reaction can be performed in the presence or absence of a basic reagent
  • the base may be selected from alkali metal hydrides such as sodium hydride; alkali metal hydroxides such as sodium or potassium hydroxide; alkali metal carbonates such as sodium bicarbonate, sodium carbonate or potassium carbonate; organic bases Class, such as pyridine, sodium methoxide, sodium ethoxide, potassium t-butoxide or sodium t-butoxide, 4-dimethylaminopyridine, triethylamine, N-methylpyrrole or diisopropylethylamine, etc .;
  • the reaction temperature can be between minus 20 degrees and the boiling point of the solvent, usually -20 to 150 ° C; the reaction time is 30 minutes to 24 hours, usually 1 to 10 hours.
  • the pesticide acceptable salt may be a salt prepared by reacting a substituted pyrazolyl pyrazole sulfonamide compound of the present invention with a chemically acceptable acid, wherein the chemically acceptable acid may be an inorganic acid ( (Such as hydrochloric acid, sulfuric acid, phosphoric acid or hydrobromic acid, etc.) or organic acids (such as oxalic acid, maleic acid, fumaric acid, malic acid, tartaric acid, citric acid or benzoic acid, etc.); the acceptable salts of the pesticides can also be It is a salt prepared by reacting a substituted pyrazolyl pyrazole sulfonamide compound with a chemically acceptable base, wherein the chemically acceptable base may be an inorganic base (such as sodium hydroxide, potassium hydroxide, Calcium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate) or organic bases (such as trimethylamine, triethylamine, etc.).
  • the acceptable salt of the pesticide may be a potassium salt, a sodium salt, an ammonium salt, a calcium salt, a pyridine salt, or a choline salt.
  • the present invention also discloses a herbicidal composition
  • a herbicidal composition comprising a herbicidally effective amount of at least one of the substituted pyrazolylpyrazolesulfonamide compounds as described above or an acceptable salt thereof as a pesticide.
  • a formulation carrier or a formulation auxiliary is also included.
  • the present invention also discloses a method for controlling unwanted plants, which comprises applying a herbicidally effective amount of at least one of the substituted pyrazolyl pyrazole sulfonamide compounds as described above or an acceptable salt thereof as a pesticide or The herbicidal composition as described above is used on unwanted plants.
  • the invention also discloses the use of the substituted pyrazolyl pyrazole sulfonamide compound as described above or at least one of the salts acceptable as pesticides or the herbicidal composition as described above for controlling harmful plants.
  • the compounds of formula I according to the invention have outstanding herbicidal activity.
  • the active substances of the invention are also effective against perennial weeds, which grow from rhizomes, rhizomes, or other perennial organs.
  • the use timing of the active substance of the present invention it may be before sowing, before germination or after germination.
  • weed species in which the active substance of the present invention can effectively include grass weeds: wild oats, brome, Festival wheat, watching Mai Niang, Japanese watching Mai Niang, yarrow, bluegrass, foxtail and so on.
  • broadleaf weeds the species whose effects can be extended to, for example, Artemisia sphaerocephala, Amaranth, Pomfret, Zeqi, Poona, Chenopodium, Firefly, Herba, Cyperus, etc.
  • the active substance of the present invention can still effectively control harmful plants, such as yarrow, firefly, quailgrass, sedge, etc. under the specific conditions of rice seeding.
  • the compound of the present invention is applied to the soil surface before germination, the seedlings of weeds can be completely prevented before weeds grow, or the weeds can stop growing when weeds develop cotyledons, and finally die completely after three to four weeks.
  • the compound of the present invention has excellent herbicidal activity against grass weeds and broadleaf weeds, it does not cause damage to important economic crop plants, such as rice, or the damage is minimal. Therefore, the compounds of the present invention are very suitable for selectively controlling unwanted plants in agricultural or ornamental plants.
  • the compounds of the present invention can significantly regulate the growth of crop plants. By regulating participation in plant metabolism, these compounds are used to orient the control of plant components and promote harvesting, such as drying and dwarfing plants. They are also suitable for regulating and inhibiting unwanted plant growth without disrupting crop growth.
  • the compounds of the present invention can be applied using general formulations, and wettable powders, soluble powders, emulsifiable concentrates, aqueous emulsions, suspensions, dispersible oil suspensions, powders, microcapsule suspensions, water-dispersible granules, water-soluble granules Agent.
  • the invention thus also provides a herbicide 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 formulation choices are: wettable powder (WP), wettable liquid (SL), soluble powder (SP), dispersible liquid (DC), aqueous (AS), microemulsion (ME), emulsifiable concentrate (EC), water emulsion (EW), sprayable solution, suspension (SC), dispersible oil suspension (OD), powder (DP), microcapsule suspension (CS), water dispersible granule (WG), water soluble Granules (SG), large granules (GG), granules (GR) for seeding and soil application, aerosols (AE), ultra-low-volume agents (ULV), and wax products.
  • Necessary formulation aids such as inert substances, surfactants, solvents and other additives.
  • suitable active substances that can be mixed with the active substance of the present invention are, for example, known substances in the "World Encyclopedia of New Pesticide Technology” (China Agricultural Science and Technology Press, 2010.9).
  • the herbicide actives mentioned below can be mixed with compounds of the formula I: acetochlor, butachlor, alachlor, isopropylchlor, mesochloramine, acetochlor, propachlor, Chlorpyramid, chlorpyramid, naproxyl, R-L-naphthoxyl, diazepam, fenpropifen, difenoxypyr, fenpyr, chlorfenapyr, fluorobutyryl Salachlor, Bromobutachlor, Metformamide, Metformamide, Acetochlor, Fluoxamid, Methiopyramide, Pomechlor, Clomazone, Efficient Straw Fluoromethyl methyl, triclopyr, dipropachlor, dimethachlor, butyramide,
  • the method for preparing the compounds of the present invention is illustrated in the following technical schemes and examples.
  • the starting materials can be purchased on the market or can be prepared by methods known in the literature or as shown in the detailed description.
  • Those skilled in the art will understand that other synthetic routes can also be used to synthesize the compounds of the present invention.
  • the specific raw materials and conditions in the synthetic route have been described below, they can be easily replaced with other similar raw materials and conditions, such as the compounds produced by the modification or variation of the preparation method of the present invention.
  • Various isomers and the like are included in the scope of the present invention.
  • the preparation method described below can be further modified according to the present disclosure using conventional chemical methods well known to those skilled in the art. For example, appropriate groups are protected during the reaction, and the like.
  • the compound was purified to obtain 3.99 g of the target compound as a milky white powder with a melting point of 127-129 ° C; 1 H-NMR (CDCl 3 -d 6 , 500MHz) ⁇ : 8.00-7.98 (m, 1H), 7.76-7.73 (m, 2H), 7.58-7.55 (m, 1H), 7.42-7.40 (m, 1H) , 4.00-3.98 (s, 3H), 3.84-3.82 (m, 2H), 2.74-2.73 (m, 2H), 2.13-2.11 (m, 2H), 188-1.86 (m, 2H) ppm.
  • Powder 20% by mass of the compound of the general formula (I) and 80% of kaolin are mixed uniformly and pulverized to obtain a product powder.
  • Wettable powder 20% by mass of the compound of the general formula (I), 8% of calcium ligninsulfonate, 2% of sodium lauryl sulfate, 3% of white carbon black, and kaolin are added to 100%. %. After mixing, the product is wettable powder after being pulverized by air flow.
  • Water-dispersible granules 60% by mass of the compound of the general formula (I), 6% of sodium ligninsulfonate, 4% of NNO (alkylnaphthalenesulfonate formaldehyde condensate), and 2% of BX (sodium dibutylnaphthalene sulfonate), 3% sodium lauryl sulfate, 5% carboxymethyl ethyl cellulose, 5% diatomaceous earth, 5% glucose, kaolin. %. Mix uniformly, pulverize by airflow, weigh the good powder, add water and mix, granulate in a granulator, then dry and sieve to obtain the product water dispersible granule.
  • test compound is dissolved in a small amount of acetone in the original medicine, and then diluted with water containing 0.1% Tween 80 to the required concentration.
  • Sprinkle a certain amount of weed seeds into a flowerpot press the seeds into the soil, and place them in a greenhouse to manage them according to conventional methods (the water layer is always kept at about 2cm). Set the dosage to 30g / ha.
  • the firefly grows to the 2-leaf stage
  • the elder plant grows to the 2-3 leaf stage
  • the sedge grows to the 2-3 leaf stage.
  • the application rate was 30 g / ha
  • the specific application amount of the flower pot was converted to the specific area of the flower pot, and two treatments were set for each treatment.) After the application, it was continued to be placed in the greenhouse to regularly observe the growth and development of the test material.
  • Level 4 equivalent to 5.1-10% of the weeds in the blank control area
  • Level 3 equivalent to 2.6-5% of weeds in the blank control area
  • Level 2 equivalent to 0-2.5% of weeds in the blank control area
  • the compounds protected by the present invention have excellent biological activity in paddy field weeds, and have very good effects on common weeds in paddy fields, especially against broad-leaved weeds common in paddy fields.
  • the biological activity has good commercial application prospects.
  • test compound is dissolved in a small amount of acetone in the original medicine, and then diluted with water containing 0.1% Tween 80 to the required concentration.
  • Quantitative rice seeds are sprinkled into flower pots, the seeds are pressed into the soil, placed in a greenhouse and managed according to conventional methods (the water layer is always maintained at about 2 cm). After sowing, the soil is sprayed through the Potter spray tower according to the experimental design dose.
  • Class a no phytotoxicity
  • Grade b the degree of phytotoxicity is 1-10%, without obvious phytotoxicity
  • the compounds protected by the present invention are basically no phytotoxicity or obvious phytotoxicity to the rice by visual inspection under the current dosage. Therefore, the compound has good safety at a suitable dosage.
  • the compounds of the present invention can be used as selective herbicides for paddy field broadleaf weeds.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne un composé de pyrazolyl pyrazole de sulfonamide substitué ou un sel à activité pesticide acceptable de celui-ci et une utilisation associée. Le composé présente une structure représentée par la formule (I). La définition de chaque groupe dans la formule est telle que donnée dans la description. Le composé pyrazolyl pyrazole de sulfonamide substitué présente une activité herbicide supérieure à celle des composés connus, et présente une excellente activité herbicide contre les mauvaises herbes dans les rizières, en particulier les mauvaises herbes à larges feuilles.
PCT/CN2019/089798 2018-06-04 2019-06-03 Composé de pyrazolyl pyrazole de sulfonamide substitué ou sel à activité pesticide acceptable de celui-ci et utilisation associée Ceased WO2019233372A1 (fr)

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CN201810564976.X 2018-06-04

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2110689A (en) * 1981-12-03 1983-06-22 Sandoz Ltd Herbicidal heterocyclic aminosulfonyl ureas and isoureas
WO1991013884A2 (fr) * 1990-03-06 1991-09-19 Nissan Chemical Industries Ltd. Derives de sulfamidosulfonamide et herbicides
CN1073440A (zh) * 1991-11-13 1993-06-23 先灵公司 新的取代的吡唑基吡唑，其制备方法，以及它们的中间体，和它们作为除草剂的用途
CN1161965A (zh) * 1992-10-12 1997-10-15 先灵公司 新的取代的吡唑衍生物
CN1195339A (zh) * 1995-09-04 1998-10-07 拜尔公司 4－硫代氨基甲酰基－1－(3－吡唑基)－吡唑化合物及其作除草剂的用途
CN1227546A (zh) * 1996-08-08 1999-09-01 拜尔公司 具有除草活性的取代的1－(3－吡唑基)－吡唑和用于其制备的中间体
CN105492443A (zh) * 2013-08-13 2016-04-13 协友株式会社 取代吡唑基吡唑衍生物及其作为除草剂的用途

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2110689A (en) * 1981-12-03 1983-06-22 Sandoz Ltd Herbicidal heterocyclic aminosulfonyl ureas and isoureas
WO1991013884A2 (fr) * 1990-03-06 1991-09-19 Nissan Chemical Industries Ltd. Derives de sulfamidosulfonamide et herbicides
CN1073440A (zh) * 1991-11-13 1993-06-23 先灵公司 新的取代的吡唑基吡唑，其制备方法，以及它们的中间体，和它们作为除草剂的用途
CN1161965A (zh) * 1992-10-12 1997-10-15 先灵公司 新的取代的吡唑衍生物
CN1195339A (zh) * 1995-09-04 1998-10-07 拜尔公司 4－硫代氨基甲酰基－1－(3－吡唑基)－吡唑化合物及其作除草剂的用途
CN1227546A (zh) * 1996-08-08 1999-09-01 拜尔公司 具有除草活性的取代的1－(3－吡唑基)－吡唑和用于其制备的中间体
CN105492443A (zh) * 2013-08-13 2016-04-13 协友株式会社 取代吡唑基吡唑衍生物及其作为除草剂的用途

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