WO2019149260A1 - Composé de pyridazinol, dérivé de celui-ci, son procédé de préparation, composition herbicide et son utilisation - Google Patents

Composé de pyridazinol, dérivé de celui-ci, son procédé de préparation, composition herbicide et son utilisation Download PDF

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WO2019149260A1
WO2019149260A1 PCT/CN2019/074315 CN2019074315W WO2019149260A1 WO 2019149260 A1 WO2019149260 A1 WO 2019149260A1 CN 2019074315 W CN2019074315 W CN 2019074315W WO 2019149260 A1 WO2019149260 A1 WO 2019149260A1
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group
alkyl
substituted
cycloalkyl
alkoxy
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PCT/CN2019/074315
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Chinese (zh)
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连磊
征玉荣
华荣保
王建峰
彭学岗
崔琦
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青岛清原化合物有限公司
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Priority claimed from CN201811035352.5A external-priority patent/CN110128352A/zh
Application filed by 青岛清原化合物有限公司 filed Critical 青岛清原化合物有限公司
Priority to RU2020128758A priority Critical patent/RU2786833C2/ru
Priority to BR112020015713-9A priority patent/BR112020015713A2/pt
Priority to US16/966,667 priority patent/US20220312770A1/en
Priority to EP19747728.4A priority patent/EP3747870A4/fr
Publication of WO2019149260A1 publication Critical patent/WO2019149260A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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
    • C07D237/14—Oxygen atoms
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D401/10—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 aromatic rings
    • 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
    • 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
    • C07D405/04—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 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
    • C07D405/02—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
    • C07D405/10—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 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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
    • 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 invention belongs to the technical field of pesticides, and in particular relates to a pyridazinol compound and a derivative thereof, a preparation method, a herbicidal composition and application.
  • Patent CN106316962A discloses a protoporphyrinogen oxidase inhibitor herbicide 3-arylpyrazinone compound, the structural formula of which is It has a controlling effect on agricultural broad-leaved weeds, farm grass weeds and sedge weeds; and azine-based herbicides such as valerian Pyridazinol Etc. is a photosystem II inhibitor herbicide that inhibits the progress of photosynthesis by blocking electron transfer and transfer of light energy.
  • the present invention provides a pyridazinol compound and a derivative thereof, a preparation method, a herbicidal composition and application, and the herbicidal activity of the compound, the derivative thereof and the composition are very High and safe for crops.
  • A represents an unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl group and an unsubstituted or substituted aryl, heteroaryl or heteroheterocyclyl;
  • substituted aryl, heteroaryl or heteroheterocyclyl refers to being substituted with one or more selected from the group consisting of halogen, cyano, nitro, azide, or Halogen-free alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, unsubstituted or substituted aryl, arylalkyl, heteroaryl, heteroarylalkyl, Aliphatic or heteroheterocyclylalkyl, RO-(CH 2 ) n -,RO-(CH 2 ) p -O-(CH 2 ) q -,RO-(CH 2 ) p -S-(CH 2 ) q -,RS-(CH 2 ) n -,RS-(CH 2 ) p -O-(CH 2 ) q -,RS-(CH 2 ) p -S-(CH 2 ) q -
  • n n
  • q represent an integer between 0 and 8, respectively
  • p represents an integer between 1 and 8;
  • R represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl with or without halogen, and unsubstituted or substituted aryl, arylalkyl, heteroaryl Heteroarylalkyl;
  • R 1 , R 2 and R 3 each independently represent hydrogen, nitro, hydroxy, amino, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl with or without halogen.
  • heteroaryl refers to an aromatic group containing at least one (eg 1, 2, 3, 4) heteroatom selected from N, O and S, such as on the ring, such as 5-14 membered heteroaryl, 5-10 membered heteroaryl, 5-9 membered heteroaryl, 5-6 membered heteroaryl.
  • the ring member of the heteroaryl group includes an N atom, it also includes a heteroaryl group in which the N atom is substituted with a substituent.
  • the substituent is selected from the group consisting of hydrogen, nitro, hydroxy, amino, C 1-6 alkyl, C 2-6 alkenyl, C 2 ⁇ with or without fluorine, chlorine, bromine.
  • A represents an unsubstituted or substituted C 1 ⁇ 8 alkyl, C 2 ⁇ 8 alkenyl group, C 2 ⁇ 8 alkynyl group, C 3 ⁇ 8 cycloalkyl, C 3 ⁇ 8 cycloalkenyl group, C 3 ⁇ 8 cycloalkyl a C 1-8 alkyl group and an unsubstituted or substituted 5-14 member aryl, heteroaryl or heteroheterocyclic group;
  • substituted C 1 ⁇ 8 alkyl, C 2 ⁇ 8 alkenyl group, C 2 ⁇ 8 alkynyl group, C 3 ⁇ 8 cycloalkyl, C 3 ⁇ 8 cycloalkenyl group, C 3 ⁇ 8 cycloalkyl C 1-8 alkyl means substituted by one or more selected from the group consisting of halogen, cyano, nitro, azide, unsubstituted or 1-5 independently selected from halogen, cyano, nitro, hydroxyl, carboxyl, mercapto, amino and C with or without halogen-containing alkyl group having 1 to 8,. 3 ⁇ C 8 cycloalkyl group,.
  • substituted 5- to 14-membered aryl, heteroaryl or heteroheterocyclyl refers to being substituted with one or more selected from the group consisting of halogen, cyano, nitro, azide. group, with or without a halogen-C 1 ⁇ 8 alkyl, C 2 ⁇ 8 alkenyl group, C 2 ⁇ 8 alkynyl group, C 3 ⁇ 8 cycloalkyl, C 3 ⁇ 8 cycloalkenyl group, C 3 ⁇ 8 cycloalkyl Alkyl C 1-8 alkyl, unsubstituted or 1 to 5 independently selected from halogen, cyano, nitro, hydroxy, carboxy, decyl, amino and C 1-8 alkyl with or without halogen, C 3-8 cycloalkyl, C 3-8 cycloalkenyl group, C 3 ⁇ 8 cycloalkyl C 1 ⁇ 8 alkyl, C 2 ⁇ 8 alkenyl group, C
  • n n
  • q represent an integer between 0 and 6, respectively
  • p represents an integer between 1 and 6;
  • R represents hydrogen, or halogen-containing C 1 ⁇ 8 alkyl, C 2 ⁇ 8 alkenyl group, C 2 ⁇ 8 alkynyl group, C 3 ⁇ 8 cycloalkyl, C 3 ⁇ 8 cycloalkenyl group, C 3 ⁇ 8 -cycloalkyl C 1-10 alkyl, and unsubstituted or 1-5 independently selected from halogen, cyano, nitro, hydroxy, carboxy, decyl, amino, and C 1-8 alkane with or without halogen group, C 3 ⁇ 8 cycloalkyl, C 3 ⁇ 8 cycloalkenyl group, C 3 ⁇ 8 cycloalkyl C 1 ⁇ 8 alkyl, C 2 ⁇ 8 alkenyl group, C 2 ⁇ 8 alkynyl group, C 1 ⁇ 8 a group in an alkoxy group, a C 1-8 alkylcarbonyl group, a C 1-8 alkoxycarbonyl group, a C 1-8
  • R 1, R 2, R 3 each independently represent hydrogen, nitro, hydroxy, amino, a halogen containing or not containing C 1 ⁇ 8 alkyl, C 2 ⁇ 8 alkenyl group, C 2 ⁇ 8 alkynyl, C 3 3-8 cycloalkyl group, C 3 ⁇ 8 cycloalkenyl group, C 3 ⁇ 8 cycloalkyl C 1 ⁇ 8 alkyl, C 1 ⁇ 8 alkoxy, C 2 ⁇ 8 alkenyloxy, C 2 ⁇ 8 alkynyl alkoxy group, C 3 ⁇ 8 cycloalkyl group, C 1 ⁇ 8 alkoxy-C 1 ⁇ 8 alkyl, C 1 ⁇ 8 alkoxycarbonyl, C 1 ⁇ 8 alkylcarbonyl, C 1 ⁇ 8-alkyl , C 1-8 alkylthiocarbonyl, C 1-8 alkylsulfonyl, C 1-8 alkylsulfonyl C 1-8 alkyl, C 1
  • the derivative means an agriculturally acceptable salt or a hydroxy derivative at the 4-position of the pyridazine ring of the formula I.
  • X represents a halogenated C 1-6 alkyl group
  • A represents an unsubstituted or substituted C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 3-6 cycloalkyl group, a C 3-6 cycloalkenyl group, a C 3-6 cycloalkane. a C 1-6 alkyl group and an unsubstituted or substituted 5 to 14 membered aryl, heteroaryl or heteroheterocyclic group;
  • substituted C 1-6 alkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 3-6 cycloalkyl group, C 3-6 cycloalkenyl group, C 3-6 cycloalkyl group C. 1 to 6 alkyl means substituted by one or more selected from the group consisting of halogen, cyano, nitro, azide, unsubstituted or 1-3 independently selected from halogen, cyano, nitro, hydroxyl, carboxyl, mercapto, amino and halogen, with or without C 1-6 alkyl, C 1-6 cycloalkyl. 3,. 3 ⁇ C 6 cycloalkenyl group, C 1-6 cycloalkyl.
  • substituted 5- to 14-membered aryl, heteroaryl or heteroheterocyclyl refers to being substituted with one or more selected from the group consisting of halogen, cyano, nitro, azide. group, with or without a halogen-C 1 ⁇ 6 alkyl group, C 2 ⁇ 6 alkenyl group, C 2 ⁇ 6 alkynyl group, C 3 ⁇ 6 cycloalkyl, C 3 ⁇ 6 cycloalkenyl group, C 3 ⁇ 6 cycloalkyl Alkyl C 1-6 alkyl, unsubstituted or 1-5 independently selected from halogen, cyano, nitro, hydroxy, carboxy, decyl, amino and C 1-6 alkyl with or without halogen, C 3-6 cycloalkyl, C 3-6 cycloalkenyl, C 3-6 cycloalkyl C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl,
  • n n
  • q represent an integer between 0 and 4, respectively
  • p represents an integer between 1 and 4;
  • R represents hydrogen, or halogen-containing C 1 ⁇ 6 alkyl group, C 2 ⁇ 6 alkenyl group, C 2 ⁇ 6 alkynyl group, C 3 ⁇ 6 cycloalkyl, C 3 ⁇ 6 cycloalkenyl group, C 3 ⁇ 6 cycloalkyl C 1-6 alkyl, and unsubstituted or 1-3 independently selected from halogen, cyano, nitro, hydroxy, carboxy, thiol, amino and C 1-6 alkane with or without halogen a group, C 3-6 cycloalkyl, C 3-6 cycloalkenyl, C 3-6 cycloalkyl C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 a group in an alkoxy group, a C 1-6 alkylcarbonyl group, a C 1-6 alkoxycarbonyl group, a C 1-6 alkylsulfonyl group, a C 1-6
  • R 1 , R 2 and R 3 each independently represent hydrogen, nitro, hydroxy, amino, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3 with or without halogen.
  • the aryl group is selected from
  • the heteroaryl group is selected from:
  • R' represents hydrogen, nitro, hydroxy, amino, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-6 cycloalkyl with or without fluorine, chlorine, bromine C 3-6 cycloalkenyl, C 3-6 cycloalkyl C 1-6 alkyl, C 1-6 alkoxy, C 2-6 alkenyloxy, C 2-6 alkynyloxy, C 3 to 6 cycloalkyloxy group, C 1-6 alkoxy C 1-6 alkyl group, C 1-6 alkoxycarbonyl group, C 1-6 alkylthiocarbonyl group, C 1-6 alkylsulfonyl group, C 1 to 6 alkylsulfonyl C 1-6 alkyl, C 1-6 alkylcarbonyl, C 1-6 alkylcarbonyl C 1-6 alkyl, C 1-6 alkyl acyloxy, C 1 ⁇ 6 alkylamino group, C 1-6 alkylaminocarbony
  • alkyl group C 2 ⁇ 6 alkenyl group, C 2 ⁇ 6 alkynyl group, C 1 6 alkoxy, C 1 ⁇ 6 alkylcarbonyl group, C 1 ⁇ 6 alkoxycarbonyl, C 1 ⁇ 6 alkylsulfonyl, C 1 ⁇ 6 alkylamino or C 1 ⁇ 6 alkyl acyloxy
  • aryl aryl C 1-6 alkyl, aryloxy, aryl C 1-6 alkyloxy, aryloxy C 1-6 alkyl, arylcarbonyl, aryl Sulfonyl, heteroaryl, heteroaryl C 1-6 alkyl, heteroaryloxy, heteroaryl C 1-6 alkyloxy, heteroaryloxy C 1-6 alkyl, heteroaryl Carbonyl group, heteroarylsulfonyl group, aliphatic heterocyclic group, aliphatic heterocyclic group C 1-6 alkyl group, aliphatic heterocyclic oxy, alipha
  • the aliphatic heterocyclic group is selected from
  • the derivative refers to an agriculturally acceptable salt or a hydroxy derivative at the 4-position of the pyridazine ring of the formula I, including esters, oximes, hydroxylamines and ether derivatives thereof.
  • X represents a halogenated C 1-6 alkyl group
  • A represents an unsubstituted or substituted C 1-6 alkyl group, a C 2-6 alkenyl group, a C 3-6 cycloalkyl group, a C 3-6 cycloalkenyl group, and an unsubstituted or substituted 5 to 14 membered aryl group, a heteroaryl or an aliphatic heterocyclic group;
  • substituted 5- to 14-membered aryl, heteroaryl or heteroheterocyclyl refers to being substituted with one or more selected from the group consisting of halogen, cyano, nitro, azide. group, with or without a halogen-C 1 ⁇ 6 alkyl group, C 2 ⁇ 6 alkenyl group, C 2 ⁇ 6 alkynyl group, C 3 ⁇ 6 cycloalkyl, C 3 ⁇ 6 cycloalkyl C 1 ⁇ 6 alkyl group , unsubstituted or 1 to 5 independently selected from the group consisting of halogen, cyano, nitro, hydroxy, carboxy, decyl, amino, and C 1-6 alkyl, C 3 -6 cycloalkyl, C with or without halogen 3- to 6 -cycloalkyl C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 alkoxy, C 1-6 alkylcarbon
  • n n
  • q represent an integer between 0 and 4, respectively
  • p represents an integer between 1 and 4;
  • R represents hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-6 cycloalkyl or C 3-6 cycloalkyl C 1-6 with or without halogen.
  • R 1 , R 2 and R 3 each independently represent hydrogen, nitro, hydroxy, amino, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3 with or without halogen.
  • the aryl group is selected from
  • the heteroaryl group is selected from:
  • R' represents hydrogen, C 1-6 alkyl with or without fluorine, chlorine or bromine, C 1-6 alkoxy C 1-6 alkyl, C 1-6 alkoxycarbonyl, C 1-6 alkane a carbonyl group, an aliphatic heterocyclic group, a phenyl group or a benzyl group;
  • the aliphatic heterocyclic group is selected from
  • the derivative refers to an agriculturally acceptable salt or a hydroxy derivative at the 4-position of the pyridazine ring of the formula I, including esters, oximes, hydroxylamines and ether derivatives thereof.
  • X represents a halogenated C 1-4 alkyl group
  • A represents an unsubstituted or substituted C 1-4 alkyl group, a C 2 4 alkenyl group, a C 3-6 cycloalkyl group, a C 3-6 cycloalkenyl group, and an unsubstituted or substituted 5 to 14 membered aryl group, a heteroaryl or an aliphatic heterocyclic group;
  • the "5- to 14-membered substituted aryl, heteroaryl or heteroheterocyclyl” refers to being substituted with one or more selected from the group consisting of fluorine, chlorine, bromine, iodine, and cyano. , nitro, azide group, C 1-4 alkyl group, C 2 4 alkenyl group, C 2 4 alkynyl group, C 3-6 cycloalkyl group, C 3 ⁇ with or without fluorine, chlorine or bromine.
  • n n
  • q represent an integer between 0, 1, 2 or 3, respectively
  • p represents an integer between 1, 2 or 3;
  • R represents hydrogen, C 1-4 alkyl, C 2 to 4 alkenyl, C 2-6 alkynyl, C 3-6 cycloalkyl or C 3-6 cycloalkyl C 1-4 with or without halogen.
  • R 1 , R 2 and R 3 each independently represent hydrogen, C 1-4 alkyl, C 2 to 4 alkenyl, C 2 to 4 alkynyl, C 3 to 6 ring with or without fluorine, chlorine or bromine.
  • the aryl group is selected from
  • the heteroaryl group is selected from:
  • R' represents hydrogen, C 1-4 alkyl with or without fluorine, chlorine or bromine, C 1-4 alkoxy C 1-4 alkyl, C 1-4 alkoxycarbonyl, C 1-4 alkane Carbonyl group, Phenyl or benzyl;
  • the aliphatic heterocyclic group is selected from
  • the derivative refers to an agriculturally acceptable salt or a hydroxy derivative at the 4-position of the pyridazine ring of the formula I, including esters, oximes, hydroxylamines and ether derivatives thereof.
  • X represents CH 2 F, CHF 2 , CF 3 , CF 2 CF 3 ;
  • A represents methyl, ethyl, And an unsubstituted or substituted 5 to 14 membered aryl, heteroaryl or aliphatic heterocyclic group;
  • substituted 5- to 14-membered aryl, heteroaryl or heteroheterocyclyl refers to being substituted with one or more selected from the group consisting of fluorine, chlorine, bromine, iodine, and cyano.
  • nitro, azide group C 1-4 alkyl group having or not containing fluorine, chlorine or bromine, C 2 to 4 alkenyl group, C 2 to 4 alkynyl group, C 3 to 6 cycloalkyl group, C 3 ⁇ 6 cycloalkyl C 1-2 alkyl, unsubstituted or 1-3 selected independently from fluorine, chlorine, bromine, cyano, hydroxy, and C 1-4 alkyl with or without fluorine, chlorine, bromine, C 1 ⁇ 4 alkoxy, C 1 ⁇ 4 alkoxycarbonyl, C 1 ⁇ 4 alkylsulfonyl or C 1 ⁇ 4 alkylamino group substituted with a phenyl, pyrrolyl, furanyl, imidazole Base, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridyl,
  • R represents hydrogen, C 1-4 alkyl with or without fluorine, chlorine or bromine, C 2 to 4 alkenyl, C 2 to 4 alkynyl, C 3 to 6 cycloalkyl, C 3 to 6 cycloalkyl a C 1-2 alkyl group, and a phenyl group, a benzyl group or a thienyl group which is unsubstituted or substituted by 1 to 3 groups independently selected from fluorine, chlorine or bromine;
  • R 1 , R 2 and R 3 each independently represent hydrogen, a C 1-4 alkyl group having or not containing fluorine, chlorine or bromine, a C 2 to 4 alkenyl group, a C 2 to 4 alkynyl group, and a C 3 to 6 ring.
  • the 5- to 14-membered aryl group is selected from
  • the heteroaryl group is selected from:
  • R' represents hydrogen, C 1-4 alkyl with or without fluorine, chlorine or bromine, C 1-4 alkoxy C 1-2 alkyl, C 1-4 alkoxycarbonyl, C 1-4 alkane Carbonyl group, Phenyl or benzyl;
  • the aliphatic heterocyclic group is selected from
  • the derivative refers to an agriculturally acceptable salt or a hydroxy derivative at the 4-position of the pyridazine ring of the formula I, including esters, oximes, hydroxylamines and ether derivatives thereof.
  • A represents an unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl group and an unsubstituted or substituted aryl or heteroaryl group;
  • substituted aryl, heteroaryl refers to a group substituted with one or more selected from the group consisting of halogen, cyano, nitro, azide, alkane with or without a halogen.
  • n, q represent an integer between 0 and 8, respectively, and p represents an integer between 1 and 8, wherein each of m, n, q, and p in the above group is independently taken, and The values are such that the substituents are different from each other;
  • R represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl with or without halogen, and unsubstituted or substituted aryl, arylalkyl, heteroaryl Heteroarylalkyl;
  • R 1 , R 2 and R 3 each independently represent hydrogen, nitro, hydroxy, amino, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl with or without halogen.
  • A represents an unsubstituted or substituted C 1 ⁇ 8 alkyl, C 2 ⁇ 8 alkenyl group, C 2 ⁇ 8 alkynyl group, C 3 ⁇ 8 cycloalkyl, C 5 ⁇ 8 cycloalkenyl group, C 3 ⁇ 8 cycloalkyl a C 1-8 alkyl group and an unsubstituted or substituted 5 to 14 membered aryl or heteroaryl group;
  • substituted C 1 ⁇ 8 alkyl, C 2 ⁇ 8 alkenyl group, C 2 ⁇ 8 alkynyl group, C 3 ⁇ 8 cycloalkyl, C 5 ⁇ 8 cycloalkenyl group, C 3 ⁇ 8 cycloalkyl C 1-8 alkyl means substituted by one or more selected from the group consisting of halogen, cyano, nitro, azide, unsubstituted or 1-5 independently selected from halogen, cyano, nitro, hydroxyl, carboxyl, mercapto, amino and C with or without halogen-containing alkyl group having 1 to 8,. 3 ⁇ C 8 cycloalkyl, C.
  • substituted 5- to 14-membered aryl, heteroaryl refers to being substituted with one or more selected from the group consisting of halogen, cyano, nitro, azide, with or without halogen-containing C 1 ⁇ 8 alkyl, C 2 ⁇ 8 alkenyl group, C 2 ⁇ 8 alkynyl group, C 3 ⁇ 8 cycloalkyl, C 5 ⁇ 8 cycloalkenyl group, C 3 ⁇ 8 cycloalkyl C 1 ⁇ 8 alkyl, unsubstituted or substituted with 1 to 5 substituents independently selected from halogen, cyano, nitro, hydroxyl, carboxyl, mercapto, amino and C with or without halogen 1-8 alkyl, C 1-8 cycloalkyl.
  • n, q represent an integer between 0 and 6, respectively, and p represents an integer between 1 and 6, wherein each of m, n, q, and p in the above group is independently taken, and The values are such that the substituents are different from each other;
  • R represents hydrogen, or halogen-containing C 1 ⁇ 8 alkyl, C 2 ⁇ 8 alkenyl group, C 2 ⁇ 8 alkynyl group, C 3 ⁇ 8 cycloalkyl, C 5 ⁇ 8 cycloalkenyl group, C 3 ⁇ 8 -cycloalkyl C 1-10 alkyl, and unsubstituted or 1-5 independently selected from halogen, cyano, nitro, hydroxy, carboxy, decyl, amino, and C 1-8 alkane with or without halogen group, C 3 ⁇ 8 cycloalkyl, C 5 ⁇ 8 cycloalkenyl group, C 3 ⁇ 8 cycloalkyl C 1 ⁇ 8 alkyl, C 2 ⁇ 8 alkenyl group, C 2 ⁇ 8 alkynyl group, C 1 ⁇ 8 a group in an alkoxy group, a C 1-8 alkylcarbonyl group, a C 1-8 alkoxycarbonyl group, a C 1-8
  • R 1, R 2, R 3 each independently represent hydrogen, nitro, hydroxy, amino, a halogen containing or not containing C 1 ⁇ 8 alkyl, C 2 ⁇ 8 alkenyl group, C 2 ⁇ 8 alkynyl, C 3 ⁇ 8 cycloalkyl, C 5 ⁇ 8 cycloalkenyl group, C 3 ⁇ 8 cycloalkyl C 1 ⁇ 8 alkyl, C 1 ⁇ 8 alkoxy, C 2 ⁇ 8 alkenyloxy, C 2 ⁇ 8 alkynyl alkoxy group, C 3 ⁇ 8 cycloalkyl group, C 1 ⁇ 8 alkoxy-C 1 ⁇ 8 alkyl, C 1 ⁇ 8 alkoxycarbonyl, C 1 ⁇ 8 alkylcarbonyl, C 1 ⁇ 8-alkyl , C 1-8 alkylthiocarbonyl, C 1-8 alkylsulfonyl, C 1-8 alkylsulfonyl C 1-8 alkyl, C 1
  • X represents a halogenated C 1-6 alkyl group
  • A represents an unsubstituted or substituted C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 3-6 cycloalkyl group, a C 5-6 cycloalkenyl group, a C 3-6 cycloalkane. a C 1 to 6 alkyl group and an unsubstituted or substituted 5 to 14 membered aryl or heteroaryl group;
  • substituted C 1-6 alkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 3-6 cycloalkyl group, C 5-6 cycloalkenyl group, C 3-6 cycloalkyl group C. 1 to 6 alkyl means substituted with one or more selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, azide, unsubstituted or 1 to 3 independent It is selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, hydroxy, carboxyl, thiol, amino and C 1-6 alkyl, C 3-6 cycloalkyl, C 5 ⁇ with or without fluorine, chlorine and bromine.
  • substituted 5- to 14-membered aryl, heteroaryl refers to being substituted with one or more selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, azide. containing or not containing fluorine, chlorine, bromine C 1 ⁇ 6 alkyl group, C 2 ⁇ 6 alkenyl group, C 2 ⁇ 6 alkynyl group, C 3 ⁇ 6 cycloalkyl, C 5 ⁇ 6 cycloalkenyl, C 3 ⁇ 6 cycloalkyl C 1-6 alkyl, unsubstituted or 1-3 independently selected from fluoro, chloro, bromo, cyano, nitro, hydroxy, carboxy, decyl, amino and with or without fluorine, chlorine C 1-6 alkyl group of bromine, C 3-6 cycloalkyl group, C 5-6 cycloalkenyl group, C 3-6 cycloalkyl C 1-6 alkyl group, C 2-6 alken
  • n, q represent an integer between 0 and 4, respectively, and p represents an integer between 1 and 4; wherein each of m, n, q, and p in the above group is independently taken, and The values are such that the substituents are different from each other;
  • R represents hydrogen, or halogen-containing C 1 ⁇ 6 alkyl group, C 2 ⁇ 6 alkenyl group, C 2 ⁇ 6 alkynyl group, C 3 ⁇ 6 cycloalkyl, C 5 ⁇ 6 cycloalkenyl group, C 3 ⁇ 6 cycloalkyl C 1-6 alkyl, and unsubstituted or 1-3 independently selected from halogen, cyano, nitro, hydroxy, carboxy, thiol, amino and C 1-6 alkane with or without halogen a group, C 3-6 cycloalkyl, C 5-6 cycloalkenyl, C 3-6 cycloalkyl C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 a group in an alkoxy group, a C 1-6 alkylcarbonyl group, a C 1-6 alkoxycarbonyl group, a C 1-6 alkylsulfonyl group, a C 1-6
  • R 1 , R 2 and R 3 each independently represent hydrogen, nitro, hydroxy, amino, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkyne with or without fluorine, chlorine or bromine. a group, a C 3-6 cycloalkyl group, a C 5-6 cycloalkenyl group, a C 3-6 cycloalkyl C 1-6 alkyl group, a C 1-6 alkoxy group, a C 2-6 alkenyloxy group, C 2-6 alkynyloxy group, C 3-6 cycloalkyloxy group, C 1-6 alkoxy C 1-6 alkyl group, C 1-6 alkoxycarbonyl group, C 1-6 alkylthiocarbonyl group, C 1-6 alkylsulfonyl, C 1-6 alkylsulfonyl C 1-6 alkyl, C 1-6 alkylcarbonyl, C 1-6 alkylcarbonyl C 1-6 alkyl, C 1-6 Alkyl
  • the aryl group is Heteroaryl is selected from R' represents hydrogen, nitro, hydroxy, amino, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-6 cycloalkyl with or without fluorine, chlorine, bromine C 5-6 cycloalkenyl, C 3-6 cycloalkyl C 1-6 alkyl, C 1-6 alkoxy, C 2-6 alkenyloxy, C 2-6 alkynyloxy, C 3 to 6 cycloalkyloxy group, C 1-6 alkoxy C 1-6 alkyl group, C 1-6 alkoxycarbonyl group, C 1-6 alkylthiocarbonyl group, C 1-6 alkylsulfonyl group, C 1 to 6 alkylsulfonyl C 1-6 alkyl, C 1-6 alkylcarbonyl, C 1-6 alkylcarbonyl C 1-6 alkyl, C 1-6 alkyl acyloxy, C 1 ⁇ 6 alkyla
  • alkyl group C 2 ⁇ 6 alkenyl group, C 2 ⁇ 6 alkynyl group, C 1 6 alkoxy, C 1 ⁇ 6 alkylcarbonyl group, C 1 ⁇ 6 alkoxycarbonyl, C 1 ⁇ 6 alkylsulfonyl, C 1 ⁇ 6 alkylamino or C 1 ⁇ 6 alkyl acyloxy
  • group Aryl aryl C 1-6 alkyl, aryloxy, aryl C 1-6 alkyloxy, aryloxy C 1-6 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl , heteroaryl C 1-6 alkyl, heteroaryloxy, heteroaryl C 1-6 alkyloxy, heteroaryloxy C 1-6 alkyl, heteroarylcarbonyl, heteroaryl Sulfonyl.
  • X represents CH 2 F, CHF 2 , CF 3 , CF 2 CF 3 ;
  • A represents Unsubstituted or substituted methyl, ethyl, vinyl, propenyl, And unsubstituted or substituted
  • n n
  • q 0, 1 or 2
  • p 1 or 2
  • R represents hydrogen, C 1-6 alkyl with or without fluorine, chlorine, bromine, C 3-6 cycloalkyl, and unsubstituted or 1-3 independently selected from fluorine, chlorine, bromine, cyano, nitro, amino and C with or without a fluorine, chlorine, bromine, alkyl of 1 to 6,. 3 ⁇ C 6 cycloalkyl, C 1-6 alkoxy, C 1-6 alkylcarbonyl, C 1-6 a phenyl group or a benzyl group substituted with a group of an alkoxycarbonyl group, a C 1-6 alkylsulfonyl group, a C 1-6 alkylamino group or a C 1-6 alkyl acyloxy group;
  • R 1 , R 2 and R 3 each independently represent hydrogen, and C 1 to 6 alkyl groups, C 3 to 6 cycloalkyl groups, C 1 to 6 alkoxy groups and C 1 to contain fluorine, chlorine or bromine.
  • R' represents hydrogen, C 1-6 alkyl.
  • Derivatives of the invention refers to an agriculturally acceptable salt or a hydroxy derivative at the 4-position of the pyridazine ring of the formula I, including derivatives such as esters, hydrazines, hydroxylamines and ethers.
  • the salt derivative is a salt used in a usual agricultural chemical, for example, an alkali metal salt, an alkaline earth metal salt or an amine salt, or, when a basic portion is present in the molecule, for example, a sulfate or a hydrochloric acid can be prepared. Salts of salts, nitrates, phosphates, and the like. When these salts are used as herbicides for agriculture and horticulture, they are also included in the present invention.
  • the "alkali metal salt” may, for example, be a sodium salt, a potassium salt or a lithium salt, preferably a sodium salt or a potassium salt.
  • the "alkaline earth metal salt” may be, for example, a calcium salt or a magnesium salt, preferably a calcium salt.
  • the "amine salt” may, for example, be an alkyl secondary amine salt, an alkyl tertiary amine salt or an alkyl quaternary ammonium salt; an alkanol primary amine salt, an alkyl alcohol secondary amine salt, an alkyl alcohol tertiary amine salt or an alkanol.
  • a quaternary ammonium salt an alkylalkanol primary amine salt, an alkylalkanol secondary amine salt, an alkylalkanol tertiary amine salt or an alkylalkanol tertiary amine salt; or an alkoxyalkanol primary amine salt, an alkoxyalkylene salt a secondary alcohol salt, an alkoxyalkanol tertiary amine salt or an alkoxyalkanol quaternary ammonium salt, preferably wherein the alkyl group, the alkanol and the alkoxy group are independently saturated and independently contain C1-C4 More preferably, it is a monoethanolamine salt, a dimethylethanolamine salt, a triethanolamine salt, a dimethylamine salt, a triethylamine salt, an isopropylamine salt, a choline salt or a diglycolamine salt.
  • Solvates of the compounds of the invention are also included in the invention.
  • the compound of the present invention also contains a compound having an asymmetric carbon atom.
  • the present invention also encompasses a mixture of an optically active body and a plurality of optically active substances in an arbitrary ratio.
  • the ester derivative refers to a compound formed by bonding an acyl group to an oxygen atom of a hydroxyl group at the 4-position of the pyridazine ring, that is, the M group in the formula I-1 is an acyl group, including a carbonyl group, a thiocarbonyl group, Sulfoxide group, sulfonyl group, phosphoryl group, thiophosphoryl group, etc., the remaining groups are as defined above in Formula I.
  • the M group in the formula I-1 may be a methyl(thio)acyl group or a C1-C18 alkane(thio)carbonyl group which may be substituted by a substituent
  • the substituent is a halogen atom, an amino group, a C3 to C8 cycloalkyl group) , C1-C8 alkoxy group, C1-C8 alkylthio group, C1-C8 alkoxycarbonyl group, C1-C8 alkylcarbonyloxy group, C1-C8 alkylcarbonyl group, C2-C8 alkenyloxy group which may be substituted by a substituent Carbonyl group
  • the substituent is a benzoyl group substituted from a C3 to C8 cycloalkyl group, a cyano group, and a substituent which is a halogen atom, a C1 to C8 alkyl group, a C1 to C8 halogenated alkyl group, and
  • the substituent is a benzoyl group which is substituted with an oxo group and may be substituted with a substituent (the substituent is a halogen atom, a C1-C8 alkyl group).
  • 1 to 3 selected from the group consisting of a C1 to C8 haloalkyl group, a C1 to C8 alkoxycarbonyl group, a nitro group, and the same or different 1 to 3 substituents selected from the C1 to C8 alkylsulfonyl groups.
  • 2 substitutions a 5- or 6-membered heterocyclic oxycarbonyl group which may be substituted by a substituent.
  • the ring of the heterocyclic ring contains one nitrogen atom, an oxygen atom or a sulfur atom, and may further contain 1 to 2 nitrogen atoms.
  • the substituent is a phenoxy group which may be substituted with a halogen atom, a C1-C8 alkyl group, and a substituent which is a halogen atom, a C1-C8 alkyl group, a C1-C8 halogenated alkyl group, a C3-C8 cycloalkyl group.
  • the substituent is a benzoyl group which may be substituted with a C3 to C8 cycloalkyl group, a cyano group and a substituent.
  • the substituent The same or different 1-3 substituents selected from a halogen atom, a C1-C8 alkyl group, a C1-C8 haloalkyl group, a C1-C8 alkoxycarbonyl group, a nitro group, and a C1-C8 alkylsulfonyl group
  • the substituent is a benzoyl group which is substituted from the oxo group and may be substituted with a substituent
  • the substituent is the same or different one to three selected from a halogen atom, a C1-C8 alkyl group, a C1-
  • the same or different 1 to 3 substituents) a phenoxy group, a 5- or 6-membered heterocyclic oxycarbonyl group which may be substituted by a substituent ⁇
  • the ring of the heterocyclic ring contains 1 nitrogen atom, oxygen atom or sulfur
  • the atom may further contain 1 to 2 nitrogen atoms.
  • the substituent is a phenoxy group which may be substituted with a halogen atom, a C1-C8 alkyl group, and a substituent which is a halogen atom, a C1-C8 alkyl group, a C1-C8 halogenated alkyl group, a C3-C8 cycloalkyl group.
  • substituents selected from the C1 to C8 alkoxycarbonyl group, 2,3-dihydro-1H-decyloxy group, and a benzoyl group which may be substituted with a substituent the substituent The same or different 1-3 substituents selected from a halogen atom, a C1-C8 alkyl group, a C1-C8 haloalkyl group, a C1-C8 alkoxycarbonyl group, a nitro group, and a C1-C8 alkylsulfonyl group)
  • substituents which are the same or different selected from the group ⁇ and a 5- or 6-membered heterocyclic oxysulfonyl group which may be substituted by a substituent One or three substituents which are the same or different selected from the group ⁇ and a 5- or 6-membered heterocyclic oxysulfonyl group which may be substituted by a substituent.
  • the ring of the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom. It can also contain 1 to 2 nitrogen atoms.
  • the substituent is a phenoxy group which may be substituted with a halogen atom, a C1-C8 alkyl group, and a substituent which is a halogen atom, a C1-C8 alkyl group, a C1-C8 halogenated alkyl group, a C3-C8 cycloalkyl group.
  • the same or different 1 to 3 substituents selected from the C1 to C8 alkoxycarbonyl group, 2,3-dihydro-1H-decyloxy group, and a benzoyl group which may be substituted with a substituent (the substituent The same or different 1-3 substituents selected from a halogen atom, a C1-C8 alkyl group, a C1-C8 haloalkyl group, a C1-C8 alkoxycarbonyl group, a nitro group, and a C1-C8 alkylsulfonyl group)
  • the same or different 1 to 3 substituents selected from the same or different 1 to 3 substituents ⁇ , a halogen-substituted fluorenyl group, and 3 to 8 membered impurities which may be substituted by a substituent Ring (thio)carbonyl ⁇
  • the ring of the heterocyclic ring contains one nitrogen atom, an oxygen atom or a sulfur atom,
  • the substituent is a C1-C8 alkyl group which may be substituted by a halogen atom, which may be one or more substituents selected from the halogen atom and the phenyl group, and C1 to C8.
  • a tricyclic heterocyclic (thio)carbonyl group (the ring of the heterocyclic ring contains one nitrogen atom, an oxygen atom or a sulfur atom, and may further contain 1 to 2 nitrogen atoms or oxygen atoms.
  • the substituent is a halogen atom.
  • the substituent is a phenoxy group which may be substituted with a halogen atom, a C1-C8 alkyl group, and a substituent which is a halogen atom, a C1-C8 alkyl group, a C1-C8 halogenated alkyl group, a C3-C8 cycloalkyl group.
  • substituents selected from the C1 to C8 alkoxycarbonyl group, 2,3-dihydro-1H-decyloxy group, and a benzoyl group which may be substituted with a substituent the substituent The same or different 1-3 substituents selected from a halogen atom, a C1-C8 alkyl group, a C1-C8 haloalkyl group, a C1-C8 alkoxycarbonyl group, a nitro group, and a C1-C8 alkylsulfonyl group)
  • substituents selected in the group ⁇ a amino(thio)acyl group which may be substituted by a substituent.
  • the substituent is a benzoyl group which is substituted with an oxo group and may be substituted with a substituent (the substituent is a halogen atom, C1 to The same or different ones selected from the group consisting of C8 alkyl group, C1-C8 haloalkyl group, C1-C8 alkoxycarbonyl group, nitro group and the same or different 1-3 substituents selected from C1-C8 alkylsulfonyl groups) 1 to 2 substituents ⁇ and a 5- or 6-membered heterocyclic oxysulfonyl group which may be substituted by a substituent.
  • the ring of the heterocyclic ring contains one nitrogen atom, an oxygen atom or a sulfur atom, and may further contain 1 to 2 nitrogen atoms.
  • the substituent is a phenoxy group which may be substituted with a halogen atom, a C1-C8 alkyl group, and a substituent which is a halogen atom, a C1-C8 alkyl group, a C1-C8 halogenated alkyl group, a C3-C8 cycloalkyl group.
  • the same or different 1 to 3 substituents selected from the C1 to C8 alkoxycarbonyl group, 2,3-dihydro-1H-decyloxy group, and a benzoyl group which may be substituted with a substituent (the substituent The same or different 1-3 substituents selected from a halogen atom, a C1-C8 alkyl group, a C1-C8 haloalkyl group, a C1-C8 alkoxycarbonyl group, a nitro group, and a C1-C8 alkylsulfonyl group)
  • the substituent is a phenoxy group which may be substituted with a halogen atom, a C1-C8 alkyl group, and a substituent which is a halogen atom, a C1-C8 alkyl group, a C1-C8 halogenated alkyl group, a C3-C8 cycloalkyl group.
  • the M group may be a C1-C10 alkane (thio)carbonyl group which may be substituted by a substituent ⁇ the substituent is from fluorine, chlorine, bromine, C3 to C6 cycloalkyl, C1 -C6 alkoxy group, C1-C6 alkylthio group, C1-C6 alkoxycarbonyl group, C1-C6 alkylcarbonyl group, C1-C6 alkylcarbonyloxy group, phenyl group which may be substituted by a substituent, phenylthio group, phenoxy group One selected from the group consisting of a benzyloxy group (the substituent is the same or different one to three substituents selected from fluorine, chlorine, bromine, C1-C6 alkyl group, and C1-C6 alkoxy group) Or a plurality of the same or different substituents ⁇ , a C3-C6 cycloalkane(thio)carbony
  • a substituent a 3-8 membered heterocyclic (thio)carbonyl group which may be substituted by a substituent ⁇ the heterocyclic ring is
  • the substituent is a C1-C6 alkyl group which may be substituted by fluorine, chlorine, bromine or a substituent which is one or more identical or different substituents selected from fluorine, chlorine, bromine and phenyl.
  • a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a phenyl group which may be substituted by a substituent (the substituent is the same or different one to three substituents selected from fluorine, chlorine, and bromine) , nitro, hydroxy, C1-C6 alkoxy, phenoxy, C1-C6 alkylthio, C2-C6 alkenylthio, and the same or different 1-3 substituents selected from the phenylthio group a 5- to 14-membered condensed bicyclic or tricyclic heterocyclic (thio)carbonyl group which may be substituted by a substituent (the heterocyclic ring is The substituent is the same or different 1 to 3 substituents selected from fluorine, chlorine, bromine and C1 to C6 alkyl groups, and a C1 to C10 alkoxy (thio)carbonyl group or C1 which may be substituted by a substituent.
  • ⁇ C10 alkylthio(thio)carbonyl (the substituent is one or more identical or different substituents selected from fluorine, chlorine, bromine, C1-C6 alkoxy and phenyl), C3 to C6 Cycloalkyloxy(thio)carbonyl, C3-C6 cycloalkylthio(thio)carbonyl, phenoxy(thio)carbonyl optionally substituted with substituent, phenylthio(thio)carbonyl, benzene C1-C6 alkane Alkoxy (thio)carbonyl or benzene C1-C6 alkylthio(thio)carbonyl (the substituent is from fluorine, chlorine, bromine, C1-C6 alkyl, cyano, C1-C6 alkylcarbonyl, C1-C6 Alkoxycarbonyl, nitro and the same or different 1 to 3 substituents selected from C1 to C6 alkoxy groups), a amino(thio
  • M represents an unsubstituted or substituted group selected from substituted methyl (thio) acyl, or C 1 ⁇ 18 alkyl (thio) carbonyl group: halogen, amino, C 3 ⁇ 8 cycloalkyl , C 1-8 alkoxycarbonyl, C 1-8 alkylcarbonyloxy, C 1-8 alkylcarbonyl, hydroxymethylphosphinyl, phenyl substituted unsubstituted or substituted by halogen or C 1-8 alkoxy , phenylthio, phenoxy or benzyloxy; phenyl unsubstituted or substituted with C 1 ⁇ 18 alkoxy (thio) carbonyl, or C 1 ⁇ 18 alkoxy group (thio) carbonyl group; C 3 ⁇ 8 ring alkylthio (thio) carbonyl group; phenyl C 1 ⁇ 8 alkylthio (thio) carbonyl group; substituents of C 2
  • the anthracene derivative refers to a thiol group-containing compound which is derivatized on the oxygen atom of the hydroxyl group at the 4-position of the pyridazine ring of the formula I.
  • the thiol group is selected from Wherein R 11 and R 22 each independently represent hydrogen, a C1 to C18 alkyl group which may be substituted with a substituent or a C2 to C18 alkenyl group (the substituent is a halogen atom, a C1 to C8 alkoxy group, a C1 to C8 alkane).
  • a thiol group one or more of the same or different substituents selected from a C1 to C8 alkylamino group, a phenyl group, a phenyl group or a 5-6 membered heterocyclic group which may be substituted with a substituent (the substitution)
  • the group is a halogen atom, a C1-C8 alkyl group, a C2-C8 alkenyl group, a C2-C8 alkynyl group, a C3-C8 cycloalkyl group, a C1-C8 haloalkyl group, a C1-C8 alkylcarbonyl group, a C1-C8 alkoxy group,
  • R 11 and R 22 each independently represent hydrogen, a C 1 -C 10 alkyl group or a C 2 -C 10 alkenyl group which may be substituted by a substituent (the substituent is from fluorine, chlorine, bromine, C1 to a C6 alkoxy group, a C1 to C6 alkylthio group, a one or more identical or different substituents selected from a C1 to C6 alkylamino group, a phenyl group which may be substituted by a substituent, a phenyl group or a 5- 6-membered aromatic heterocyclic group (the aromatic heterocyclic group is The substituent is from fluorine, chlorine, bromine, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxy, C1-C6 alkoxycarbonyl.
  • R 11 , R 22 forms a 5, 6 membered saturated carbocyclic ring or a 5 or 6 membered heterocyclic ring (containing at least one hetero atom such as oxygen, sulfur, nitrogen, etc.).
  • R 11 and R 22 are each independently selected from hydrogen, unsubstituted or substituted by a C 1-18 alkyl group selected from the group consisting of C 1-8 alkoxy and C 1 ⁇ 8 alkylthio, and phenyl or 5-6 membered aromatic heterocyclic group which is unsubstituted or substituted by halogenated C 1-10 alkyl group, or R 11 and R 12 form a 5-6 membered saturated carbocyclic or heterocyclic ring. .
  • the hydroxylamine derivative refers to a hydroxylamine group-containing compound which is formed by bonding an oxygen atom of a hydroxyl group at the 4-position of the pyridazine ring of the formula I.
  • the hydroxylamine group is selected from Wherein R 11 ' and R 22 ' each independently represent hydrogen, a C1 to C18 alkyl group which may be substituted with a substituent or a C2 to C18 alkenyl group (the substituent is a halogen atom, a C1 to C8 alkoxy group, or a C1 ⁇ ).
  • a C8 alkylthio group one or more identical or different substituents selected from a C1 to C8 alkylamino group, a phenyl group which may be substituted with a substituent (the substituent is a halogen atom, a C1-C8 alkyl group) , C2—C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C1-C8 haloalkyl, C1-C8 alkylcarbonyl, C1-C8 alkoxy, C1-C8 alkoxycarbonyl, C1-C8
  • substituents selected from the group consisting of an alkylamino group, a hydroxyl group, a carboxyl group, a decyl group, an amino group, a cyano group, a nitro group and a C1-C8 alkylsulfonyl group, and a C1-C18 alkoxycarbon
  • the substituent is a benzoyl group substituted with an oxo group and a substituent which may be substituted by a halogen atom, a C1-C8 alkyl group, and a C1 group.
  • a nitrogen atom, an oxygen atom or a sulfur atom which may additionally contain further 1 or 2 nitrogen atoms.
  • the substituent is a phenoxy group which may be substituted with a halogen atom, a C1-C8 alkyl group, and a substituent which is a halogen atom, a C1-C8 alkyl group, a C1-C8 halogenated alkyl group, a C3-C8 cycloalkyl group.
  • substituents selected from the C1 to C8 alkoxycarbonyl group, 2,3-dihydro-1H-decyloxy group, and a benzoyl group which may be substituted with a substituent the substituent The same or different 1-3 substituents selected from a halogen atom, a C1-C8 alkyl group, a C1-C8 haloalkyl group, a C1-C8 alkoxycarbonyl group, a nitro group, and a C1-C8 alkylsulfonyl group)
  • substituents which are the same or different selected from the group ⁇ and a 5- or 6-membered heterocyclic oxysulfonyl group which may be substituted by a substituent One or three substituents which are the same or different selected from the group ⁇ and a 5- or 6-membered heterocyclic oxysulfonyl group which may be substituted by a substituent.
  • the ring of the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom. It can also contain 1 to 2 nitrogen atoms.
  • the substituent is a phenoxy group which may be substituted with a halogen atom, a C1-C8 alkyl group, and a substituent which is a halogen atom, a C1-C8 alkyl group, a C1-C8 halogenated alkyl group, a C3-C8 cycloalkyl group.
  • the same or different 1 to 3 substituents selected from the C1 to C8 alkoxycarbonyl group, 2,3-dihydro-1H-decyloxy group, and a benzoyl group which may be substituted with a substituent (the substituent The same or different 1-3 substituents selected from a halogen atom, a C1-C8 alkyl group, a C1-C8 haloalkyl group, a C1-C8 alkoxycarbonyl group, a nitro group, and a C1-C8 alkylsulfonyl group)
  • the same or different 1 to 3 substituents selected from the same or different 1 to 3 substituents ⁇ The same or different 1 to 3 substituents selected from the same or different 1 to 3 substituents ⁇ .
  • R 11 ', R 22 ' independently represent hydrogen, C1-C10 alkyl or C2-C10 alkenyl which may be substituted by a substituent (the substituent is from fluorine, chlorine, bromine One or more identical or different substituents selected), a C1-C10 alkoxycarbonyl group, a phenyl group or a benzoyl group which may be substituted by a substituent (the substituent is from fluorine, chlorine, bromine, C1 to C6) Alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1 -C6 alkylamino group, hydroxyl group, carboxyl group, mercapto group, amino group, cyano group, nitro group and the same or
  • R 11 'and R 22 ' each independently represent a C 1-10 alkyl group.
  • the ether derivative refers to a compound which is bonded to an oxygen atom of a hydroxyl group at the 4-position of the pyridazine ring to form a group: a cyano group, a C1 to C18 alkyl group which may be substituted with a substituent or a C2 to C18 alkenyl group.
  • the substituent is a halogen atom, a C1-C8 alkoxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, a di-C1-C8 alkylamino group, a C1-C8 alkoxycarbonyl group, a C1-C8 alkoxy group.
  • the same or different 1 to 2 substituents selected from the same or different 1 to 3 substituents selected from the sulfonyl group ⁇ , a hydroxyl group, a carboxyl group, a thiol group, an amino group, a phenyl group, a nitro group may be substituted a C1-C8 alkoxy group, a C1-C8 alkylamino group or a C1-C8 alkylthio group (the substituent is the same or different one to three substituents selected from a halogen atom and a phenyl group), a phenoxy group or a 5- or 6-membered heterocyclic oxycarbonyl group which may be substituted by a substituent.
  • the ring of the heterocyclic ring contains one nitrogen atom, an oxygen atom or a sulfur atom, and may further contain 1 to 2 Nitrogen atom.
  • the substituent is a phenoxy group which may be substituted with a halogen atom, a C1-C8 alkyl group, and a substituent which is a halogen atom, a C1-C8 alkyl group, a C1-C8 halogenated alkyl group, a C3-C8 cycloalkyl group.
  • substituents selected from the C1 to C8 alkoxycarbonyl group, 2,3-dihydro-1H-decyloxy group, and a benzoyl group which may be substituted with a substituent the substituent The same or different 1-3 substituents selected from a halogen atom, a C1-C8 alkyl group, a C1-C8 haloalkyl group, a C1-C8 alkoxycarbonyl group, a nitro group, and a C1-C8 alkylsulfonyl group)
  • substituents which are the same or different selected from the group ⁇ and a 5- or 6-membered heterocyclic oxysulfonyl group which may be substituted by a substituent One or three substituents which are the same or different selected from the group ⁇ and a 5- or 6-membered heterocyclic oxysulfonyl group which may be substituted by a substituent.
  • the ring of the heterocyclic ring contains one nitrogen atom, oxygen atom or sulfur atom. It can also contain 1 to 2 nitrogen atoms.
  • the substituent is a phenoxy group which may be substituted with a halogen atom, a C1-C8 alkyl group, and a substituent which is a halogen atom, a C1-C8 alkyl group, a C1-C8 halogenated alkyl group, a C3-C8 cycloalkyl group.
  • the same or different 1 to 3 substituents selected from the C1 to C8 alkoxycarbonyl group, 2,3-dihydro-1H-decyloxy group, and a benzoyl group which may be substituted with a substituent (the substituent The same or different 1-3 substituents selected from a halogen atom, a C1-C8 alkyl group, a C1-C8 haloalkyl group, a C1-C8 alkoxycarbonyl group, a nitro group, and a C1-C8 alkylsulfonyl group)
  • the same or different 1 to 3 substituents selected from the same or different 1 to 3 substituents ⁇ The same or different 1 to 3 substituents selected from the same or different 1 to 3 substituents ⁇ .
  • the ether derivative refers to a compound formed by bonding a group such as a C8-C18 alkyl group or a C8-C18 alkenyl group to an oxygen atom of a hydroxyl group at the 4-position of the pyridazine ring.
  • Substituted C1-C10 alkyl group or C2-C10 alkenyl group is from fluorine, chlorine, bromine, C1-C6 alkoxy group, C1-C6 alkylthio group, C1-C6 alkylamino group, C1-C6 Alkoxycarbonyl, C1-C6 alkoxycarbonyloxy, one or more identical or different substituents selected from C3 to C6 cycloalkoxycarbonyloxy ⁇ , phenyl, benzyl which may be substituted by a substituent Or a benzoyl C1-C6 alkyl group (the substituent is from fluorine, chlorine, bromine, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 halogenated alkane , C1-C6 alkylcarbonyl, C1-C6 alkoxy, C1-
  • C 1-18 alkyl which is unsubstituted or substituted with a substituent selected from C 1-8 alkoxycarbonyl and C 1-8 alkoxycarbonyloxy; unsubstituted or A phenyl group, a benzyl group or a benzoyl C 1-8 alkyl group substituted with a substituent selected from the group consisting of a halogen and a C 1-8 alkoxy group.
  • a method for preparing the pyridazine alcohol compound comprising the steps of:
  • L represents a halogen, preferably bromine, and the remaining groups are as defined above.
  • each of the above steps is carried out in the range of from 20 to 150 ° C, preferably from 50 to 130 ° C; in some preferred embodiments, the steps (1) and (b) are in the catalyst, base and The catalyst is carried out in the presence of a solvent of Pd(dppf)Cl 2 CH 2 Cl 2 , Pd(dba) 2 , Pd 2 (dba) 3 , Pd(PPh 3 ) 4 , PdCl 2 , Pd(OAc) 2 , Pd ( Dppf) Cl 2 , Pd(PPh 3 ) 2 Cl 2 or Ni(dppf)Cl 2 , the base being selected from the group consisting of Et 3 N, NaHCO 3 , KOAc, K 2 CO 3 , K 3 PO 4 , Na 2 CO 3 , One or more of CsF, Cs 2 CO 3 , t-BuONa, EtONa, KOH, and NaOH, the solvent is THF/water, toluene
  • Y 1 is a halogen, preferably chlorine or bromine; the remaining groups are as defined above.
  • Y 2 is a halogen, preferably chlorine or fluorine; the remaining groups are as defined above.
  • the reaction for preparing the ester and ether derivatives thereof and the second step of preparing the oxime and hydroxylamine derivatives are carried out in the presence of a base selected from the group consisting of hydrogen and a solvent.
  • a base selected from the group consisting of hydrogen and a solvent.
  • a base selected from the group consisting of hydrogen and a solvent.
  • a base selected from the group consisting of hydrogen and a solvent.
  • the solvent is THF, 1,4- Dioxane, toluene, 1,2-dichloroethane, ethyl acetate, acetonitrile, DMF, acetone, dichloromethane or chloroform.
  • the first step in the preparation of the oxime and hydroxylamine derivative is carried out in the presence of a halogenating agent which is Phenofluor/yttrium fluoride or POCl 3 ,
  • the solvent is selected from one or more selected from the group consisting of toluene, 1,2-dichloroethane, and DMF; and the reaction temperature is selected from the range of 0 to 120 ° C, preferably 20 to 80 ° C.
  • the terminology used, whether used alone or in a compound, means a substituent: an alkyl group having more than two carbon atoms or "-(CH 2 ) n - " can be straight or branched.
  • the alkyl group in the compound "heteroarylalkyl group” and "RO-(CH 2 ) n -" -(CH 2 ) n - may be -CH 2 -, -CH 2 CH 2 -, -CH (CH 3 )-, -C(CH 3 ) 2 -, and the like.
  • the alkyl group is, for example, methyl; ethyl; n-propyl or isopropyl; n-butyl, isobutyl, tert-butyl or 2-butyl; pentyl; hexyl, for example n-hexyl, isohexyl And 1,3-dimethylbutyl.
  • an alkenyl group is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, butyl 3--3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl.
  • An alkynyl group is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. Multiple bonds can be placed at any position of each unsaturated group.
  • a cycloalkyl group is a carbocyclic saturated ring system having three to eight carbon atoms, such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group.
  • a cycloalkenyl group is a monocyclic alkenyl group having three to eight carbon ring members, such as a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, and a cyclohexenyl group, wherein the double bond can be at any position.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • heterocyclic groups include aliphatic heterocyclic groups and heteroaryl groups.
  • a group is substituted by a group, this is understood to mean that the group is substituted by one or more groups which are identical or different from those mentioned. Further, the same or different substitution characters contained in the same or different substituents are independently selected and may be the same or different. The same applies to ring systems formed by different atoms and units. Also, the scope of the claims will exclude those compounds which are known to those skilled in the art to be chemically unstable under standard conditions.
  • a group not labeled with a specific linking position may be attached at any position, including a position to be bonded to C or N; if it is substituted, the substituent may be substituted at any position as long as it is Compound key connection rules. If replaced by a methyl group Representable Wait.
  • the compounds of the present invention may exist in the form of one or more stereoisomers.
  • the various isomers include enantiomers, diastereomers, geometric isomers. It is within the scope of the invention for these isomers to include mixtures of such isomers.
  • a herbicidal composition comprising (i) a pyridazinol compound of the formula I or a derivative thereof as shown in the formula I-1.
  • it further comprises (ii) one or more additional herbicides and/or safeners.
  • an agrochemically acceptable formulation aid is also included.
  • composition of the compound of the present invention in a mixture preparation or in a tank mixture, for example, known active substances based on inhibition of, for example, an acetyl lactate synthase, an acetyl-CoA carboxylase, a cellulose synthase, an alkene can be used.
  • the additional herbicide is selected from one of an HPPD inhibitor, a hormone, and a PDS inhibitor; preferably, the HPPD inhibitor is sulcotrione (CAS No.: 99105-77-8), mesotrione (CAS) No.: 104206-82-8), oxafluridone (CAS No.: 210631-68-8), sulfonone (CAS No.: 335104-84-2), flucarbazone (CAS No.: 352010-68- 5), Furansulfoxone (CAS No.: 473278-76-1), Bicyclosulfonate (CAS No.: 156963-66-5), Lancotrione (CAS No.: 1486617-21-3), Dioxazolone ( CAS No.: 1622908-18-2), cyclopyridone (CAS No.: 1855929-45-1), triazosinone (CAS No.: 1911613-97-2), oxazolone (CAS number) :1992017-55-6), sulfonylpyr
  • the flupiroxyacetic acid derivative comprises, but is not limited to: isooctyl chlorofluoxetine; 2 methyl 4-chloro, 2-methyl-4-chlorophenoxypropionic acid, MCPB derivatives include but are not limited to: sodium Salt, potassium salt, dimethylammonium salt, isopropylamine salt, etc., and methyl ester, ethyl ester, isooctyl ester, ethyl thioester, etc.; 2,4-D, 2,4-D-propionic acid, 2,4-DB Derivatives include, but are not limited to, salts such as sodium salts, potassium salts, dimethylammonium salts, triethanolammonium salts, isopropylamine salts, choline, and the like, and esters such as methyl esters, ethyl esters, butyl esters, isooctyl esters, and the like.
  • the component (i) is N-(2-aminoethyl)
  • the additional herbicide is selected from the group consisting of sulcotrione, mesotrione, oxazolone, sulfonone, flufenicone, furanone, dicyclohexanone, lancotrione , oxazolone, ciprofloxacin, triazosulfone, oxazolone, sulfonylpyrazole, pyroxamate, tolpyralate, isoxaflutole, flupirtine or its ester , fluorochloropyridinium, chlorofluoropyridyl ester, quinclorac, 2, 4-chloro or its salt, 2-methyl-4-chlorophenoxypropionic acid or its salt, MCPB or its salt/ester , 2,4-D or a salt thereof, 2,4-dipropionic acid or a salt thereof, 2,4-DB or a salt thereof, dicamba, azuridine, triclopyran,
  • a method for controlling a harmful plant comprising applying at least one of a herbicidal effective amount of a pyridazine compound or a derivative thereof as described above or the herbicidal composition to the harmful plant or region.
  • the pyridazinol compound or derivative thereof or the herbicidal composition is used to control harmful plants in useful crops.
  • the useful crop is a crop that has been treated with a genetically modified crop or genome editing technique.
  • the useful crop is selected from the group consisting of wheat, corn, rice, soybean, cotton, canola, millet, and sorghum.
  • 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 described herein exhibit excellent inhibitory activity against the following harmful plants: Amaranthus chinensis, Amaranthus, Possina, Poria, Valerian, Foxtail, Poria, Castor, Sowing Brassica and Achyranthes.
  • 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 special 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.
  • 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 90%
  • Level 6 The growth control rate is above 60%
  • Level 3 growth control rate is above 30%
  • Level 1 The growth control rate is less than 20%
  • the above growth control rate is the fresh weight control rate.
  • Post-emergence test Place monocotyledonous and dicotyledon weed seeds and main crop seeds (wheat, corn, rice, soybean, cotton, canola, millet, sorghum) in a plastic pot containing soil, then cover 0.5-2 Cm soil, so that it grows in a good greenhouse environment, after 2-3 weeks of sowing, the test plants are treated in the 2-3 leaf stage, and the compound of the present invention is dissolved in acetone, and then Tween 80 is added, with a certain amount. The water was diluted to a certain concentration of solution, and 80% vegetable oil methyl ester synergist 1500 g/ha was added and sprayed onto the plants with a spray tower. After application for 3 weeks in the greenhouse, the experimental effects of weeds after 3 weeks are shown in Tables 3 and 4.
  • N is no data.
  • Control compound C (Selected from patent CN106316962A)
  • Control compound D (Selected from patent CN106316962A)
  • N is no data.
  • the compound of the present invention has excellent herbicidal activity as compared with the control compound.
  • test compound has good selectivity for crops before and after seedling application, especially for crops such as wheat, rice, soybean, cotton, corn, sorghum, and millet.
  • the compound of the present invention to be tested was dissolved in acetone, and then Tween 80 was added thereto, and diluted to a certain concentration with a certain amount of water, and sprayed immediately after sowing. After application for 4 weeks in the greenhouse, the results of the experiment were observed after 3 weeks, and it was found that most of the agents of the present invention were excellent in the measurement of 250 g/ha, especially for weeds such as valerian, horse pond, ramie, and many other compounds. Good selectivity for corn, wheat, rice, soybeans, and rapeseed.
  • the compounds of the present invention generally have good weed control effects, especially for major broadleaf weeds such as weeds, stalks, and stalks, which are widely occurring in corn fields, paddy fields, and wheat fields.
  • the effect has good business value.
  • the broad-leaved weeds such as Maijiagong, Hog Cholera, and Brassica, which are resistant to ALS inhibitors, have extremely high activity.
  • the paddy soil After filling the paddy soil in a 1/1,000,000 hectare tank, seeds of valerian, flamingo, wolf grass, and wild sage were planted, and the soil was gently covered thereon. Thereafter, it was placed in a greenhouse at a depth of 0.5 to 1 cm, and the tubers of the wild sage were implanted the next day or two days later. Thereafter, the water retention depth is 3-4 cm, and the wettability of the compound of the present invention is prepared according to the usual preparation method at the time when the grass, the firefly, the wolf grass reaches 0.5 leaf, and the wild sage reaches the primary leaf stage. A water dilution of a powder or a suspension is uniformly dripped with a pipette to achieve a prescribed 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 the transplantation.
  • the fertility status of Valerian, Firefly, Wolfgrass and Wild Sage was observed by naked eye on the 14th day after treatment, and the growth status of rice on the 21st day after the treatment, the herbicidal effect was evaluated at the activity standard level of 1-10.
  • Many of the compounds of the present invention have been found to have excellent activity and selectivity, especially for wild sage and valerian. Note: Valerian, sputum, wild sage, and wolf seed were collected from Heilongjiang, China, and tested for resistance to conventional doses of pyrazosulfuron.
  • the present invention relates to a herbicidal composition
  • a herbicidal composition comprising the active ingredient (i) (such as the compound of the formula I) and the active ingredient (ii), and some of the compositions are listed below:
  • 50+ sulcotrione 50+ mesotrione, 50+ oxazolone, 50+ sulfolone, 50+ flufenone, 50+ furanone, 50+ dicyclohexanone, 50+lancotrione 50+ oxazolone, 50+cycloflufenazone, 50+ triazosinone, 50+ oxazolone, 50+ sulfonylpyrazole, 50+ pyrazole, 50+ pyridine Ketone, 50+ tolpyralate, 50+ fenquinotrione, 50+ isoxaflutole, 50+ flufenoxyacetic acid or its ester, 50+ fluorochloropyridinium ester, 50+ chlorofluoropyridinium ester, 50+ quinclorac, 50+chlorochloroquinic acid, 50+2 methyl 4-chloro or its salt, 50+2-methyl-4-chlorophenoxypropionic acid or its salt, 50+MCPB or its salt
  • 51+ sulcotrione 51+ mesotrione, 51+ oxazolone, 51+ sulfolone, 51+ flufenone, 51+ furanone, 51+ dicyclohexanone, 51+lancotrione , 51+ oxazolone, 51+cycloflufenazone, 51+ triazosinone, 51+ oxazolone, 51+ sulfonylpyrazole, 51+ pyrazole, 51+ pyridine Ketone, 51+tolpyralate, 51+fenquinotrione, 51+ isoxaflutole, 51+ flufenoxyacetic acid or its ester, 51+ fluorochloropyridinium, 51+ chlorofluoropyridyl ester, 51+ quinclorac, 51+chlorochloroquinic acid, 51+2 methyl 4-chloro or its salt, 51+2-methyl-4-chlorophenoxypropionic acid or its salt, 51+MCPB or its salt,
  • 57+ sulcotrione 57+ mesotrione, 57+ oxazolone, 57+ sulfolone, 57+ flufenazone, 57+ furanone, 57+ dicyclohexanone, 57+lancotrione 57+ oxazolone, 57+cycloflufenone, 57+ triazosinone, 57+ oxazolone, 57+ sulfonylpyrazole, 57+ pyrazole, 57+ pyridine Ketone, 57+tolpyralate, 57+fenquinotrione, 57+ isoxaflutole, 57+ flufenoxyacetic acid or its ester, 57+ fluorochloropyridinium, 57+ chlorofluoropyridyl ester, 57+ quinclorac, 57+chlorochloroquinic acid, 57+2 methyl 4-chloro or its salt, 57+2-methyl
  • 206+ sulcotrione 206+ mesotrione, 206+ oxazolone, 206+ sulfolone, 206+ flufenazone, 206+ furanone, 206+bicyclic sulfoxone, 206+lancotrione , 206 + oxazolone, 206 + cycloflufenone, 206 + triazosulfone, 206 + oxazolone, 206 + sulfonylpyrazole, 206 + pyrazole, 206 + pyridine Ketone, 206+tolpyralate, 206+fenquinotrione, 206+ isoxaflutole, 206+ flufenoxyacetic acid or its ester, 206+ fluorochloropyridinium, 206+ chlorofluoropyridyl ester, 206+ quinclorac, 206+chlorochloroquinic acid, 206+2 methyl 4-chloro or its salt
  • 207+ sulcotrione 207+ mesotrione, 207+ oxazolone, 207+ sulfolone, 207+ flufenazone, 207+ furanone, 207+bicyclosulfone, 207+lancotrione 207+ oxazolone, 207+cycloflufenazone, 207+ triazosinone, 207+ oxazolone, 207+ sulfonylpyrazole, 207+ pyrazole, 207+ pyridine Ketone, 207+tolpyralate, 207+fenquinotrione, 207+ isoxaflutole, 207+ flufenoxyacetic acid or its ester, 207+ fluorochloropyridin, 207+ chlorofluoropyridyl ester, 207+ quinclorac, 207+chlorochloroquinic acid, 207+2 methyl 4-chloro or its salt, 207+2-methyl
  • 737+ sulcotrione 737+ mesotrione, 737+ oxazolone, 737+ sulfonone, 737+ flufenazone, 737+ furansulfone, 737+bicyclosulfone, 737+lancotrione , 737+ oxazolone, 737+cycloflufenazone, 737+ triazolone, 737+ oxazolone, 737+ sulfonylpyrazole, 737+ pyrazol, 737+ pyridine Ketone, 737+tolpyralate, 737+fenquinotrione, 737+ isoxaflutole, 737+ flufenoxyacetic acid or its ester, 737+ fluorochloropyridinium, 737+ chlorofluoropyridyl ester, 737+ quinclorac, 737+chlorochloroquinic acid, 737+2 methyl 4-chloro or its salt, 737
  • 1-43+ sulcotrione 1-43+ mesotrione, 1-43+oxazolone, 1-43+cyclosulfone, 1-43+flufenone, 1-43+furan Ketone, 1-43+bicyclosulfone, 1-43+lancotrione, 1-43+oxazolone, 1-43+cycloflufenone, 1-43+triazolone, 1-43+ Oxazolone, 1-43+ sulfonylpyrazole, 1-43+ pyrazol, 1-43+pyrazone, 1-43+tolpyralate, 1-43+fenquinotrione, 1-43+ Zoxaconone, 1-43+ flufenoxyacetic acid or its ester, 1-43+ fluorochloropyridinium, 1-43+chlorofluoropyridinium ester, 1-43+dichloroquinoic acid, 1-43+chloroform Quinolinic acid, 1-43+2 methyl 4-chloro or its salt, 1-43+2-methyl-4-chloroph
  • 1-226+ sulcotrione 1-226+ mesotrione, 1-226+oxazolone, 1-226+cyclosulfone, 1-226+flufenone, 1-226+furan Ketone, 1-226+bicyclosulfoxone, 1-226+lancotrione, 1-226+oxazolone, 1-226+cyclopropazone, 1-226+triazolone, 1-226+ Oxazolone, 1-226+ sulfonylpyrazole, 1-226+ pyrazol, 1-226+pyrazone, 1-226+tolpyralate, 1-226+fenquinotrione, 1-226+ Zytotrione, 1-226+ flupiroxyacetic acid or its ester, 1-226+ fluorochloropyridinium, 1-226+ chlorofluoropyridyl ester, 1-226+ quinclorac, 1-226+chloro Quinolinic acid, 1-226+2 methyl 4-
  • 1-227+ sulcotrione 1-227+ mesotrione, 1-227+ oxazolone, 1-227+ sulfonone, 1-227+flufenone, 1-227+ furan Ketone, 1-227+bicyclosulfone, 1-227+lancotrione, 1-227+ oxazolone, 1-227+cycloflufenone, 1-227+ triazosinone, 1-227+ Oxazolone, 1-227+ sulfonylpyrazole, 1-227+ pyrazol, 1-227+pyrazone, 1-227+tolpyralate, 1-227+fenquinotrione, 1-227+ Zytotrione, 1-227+ flufenoxyacetic acid or its ester, 1-227+ fluorochloropyridinium, 1-227+ chlorofluoropyridinium, 1-227+ quinclorac, 1-227+chloro Quinolinic acid, 1-227+2
  • 1-228+ sulcotrione 1-228+ mesotrione, 1-228+ oxazolone, 1-228+ sulfonone, 1-228+flufenone, 1-228+ furan Ketone, 1-228+bicyclosulfoxone, 1-228+lancotrione, 1-228+oxazolone, 1-228+cyclopyridone, 1-228+triazolone, 1-228+ Oxazolone, 1-228+ sulfonylpyrazole, 1-228+ pyrazol, 1-228+pyrazin, 1-228+tolpyralate, 1-228+fenquinotrione, 1-228+ Zytotrione, 1-228+ flufenoxyacetic acid or its ester, 1-228+ fluorochloropyridinium, 1-228+ chlorofluoropyridinium, 1-228+dichloroquinoic acid, 1-228+chloroform Quinolinic acid, 1-228
  • 1-229+ sulcotrione 1-229+ mesotrione, 1-229+ oxazolone, 1-229+ sulfonone, 1-229+ flufenone, 1-229+ furan Ketone, 1-229+bicyclosulfolone, 1-229+lancotrione, 1-229+ oxazolone, 1-229+cycloflufenone, 1-229+ triazosulfone, 1-229+ Oxazolone, 1-229+ sulfonylpyrazole, 1-229+ pyrazol, 1-229+pyrazone, 1-229+tolpyralate, 1-229+fenquinotrione, 1-229+ Zytotrione, 1-229+ flupiroxyacetic acid or its ester, 1-229+ fluorochloropyridinium, 1-229+ chlorofluoropyridyl ester, 1-229+ quinclorac, 1-229+chloromethyl Quinolinic acid,
  • 1-230+ sulcotrione 1-230+ mesotrione, 1-230+oxazolone, 1-230+cyclosulfone, 1-230+flufenone, 1-230+furan Ketone, 1-230+bicyclosulfone, 1-230+lancotrione, 1-230+ oxazolone, 1-230+cycloflufenone, 1-230+ triazosinone, 1-230+ Oxazolone, 1-230+ sulfonylpyrazole, 1-230+ pyrazol, 1-230+pyrazone, 1-230+tolpyralate, 1-230+fenquinotrione, 1-230+ Zytotrione, 1-230+ flufenoxyacetic acid or its ester, 1-230+ fluorochloropyridinium, 1-230+ chlorofluoropyridinate, 1-230+dichloroquinoic acid, 1-230+chloroform Quinolinic acid, 1-230
  • the actual control effect of the mixed weeds of the above parts (i) and (ii) is determined by the stem and leaf treatment method, that is, the weeds are in the 3-4 leaf stage, the hand sprayer, the water exchange amount is 30 kg / 667 m 2 , The stem and leaf spray is evenly sprayed.
  • the combined action type when the E-E0 value is greater than 10% for synergism, less than -10% for antagonism, between -10% and 10% for additive effect.
  • the other component (i) in the present invention can be similarly mixed with the component (ii) to produce a similar herbicidal effect.
  • many of the compounds of the present invention and their compositions have good selectivity against grasses such as Zoysia, Bermudagrass, tall fescue, bluegrass, ryegrass, seashore gar, etc., and can prevent many key grasses. Weeds and broadleaf weeds. Tests on wheat, corn, rice, sugar cane, soybean, cotton, oil sunflower, potato, fruit trees, and vegetables under different application methods also showed excellent selectivity and commercial value.

Abstract

La présente invention concerne le domaine de la technologie des pesticides, et concerne spécifiquement un composé de pyridazinol tel que représenté par la formule générale I, un dérivé de celui-ci, son procédé de préparation, une composition herbicide de celui-ci et son utilisation. Le composé, le dérivé de celui-ci et la composition herbicide de celui-ci ont une activité herbicide très élevée et sont sûrs et sélectifs pour les cultures. (Formule I).
PCT/CN2019/074315 2018-02-02 2019-02-01 Composé de pyridazinol, dérivé de celui-ci, son procédé de préparation, composition herbicide et son utilisation WO2019149260A1 (fr)

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RU2020128758A RU2786833C2 (ru) 2018-02-02 2019-02-01 Пиридазинольное соединение, его производное, способ его получения, содержащая его гербицидная композиция и его применение
BR112020015713-9A BR112020015713A2 (pt) 2018-02-02 2019-02-01 Composto piridazinol, derivado do mesmo, método de preparação, composição herbicida e uso do mesmo
US16/966,667 US20220312770A1 (en) 2018-02-02 2019-02-01 Pyridazinol compounds and derivatives, preparation methods, herbicidal compositions and applications thereof
EP19747728.4A EP3747870A4 (fr) 2018-02-02 2019-02-01 Composé de pyridazinol, dérivé de celui-ci, son procédé de préparation, composition herbicide et son utilisation

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CN201810104963.4 2018-02-02
CN201810104963 2018-02-02
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CN201811035352.5A CN110128352A (zh) 2018-02-02 2018-09-06 哒嗪醇类化合物及其衍生物、制备方法、除草组合物和应用

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EP3647308A4 (fr) * 2017-06-26 2021-01-06 Nippon Soda Co., Ltd. Composé hétéroarylpyrimidine, et agent de lutte contre les organismes nuisibles
CN112390759A (zh) * 2019-08-16 2021-02-23 青岛清原化合物有限公司 一种哒嗪醇类化合物及其衍生物、制备方法、除草组合物和应用
CN113203815A (zh) * 2021-05-13 2021-08-03 黑龙江省农业科学院农产品质量安全研究所 基于uplc-msms检测糙米、稻壳和秸秆中氟酮磺草胺及其代谢物的方法

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EP3647308A4 (fr) * 2017-06-26 2021-01-06 Nippon Soda Co., Ltd. Composé hétéroarylpyrimidine, et agent de lutte contre les organismes nuisibles
US11427564B2 (en) 2017-06-26 2022-08-30 Nippon Soda Co., Ltd. Heteroaryl pyrimidine compound and pest control agent
CN112390759A (zh) * 2019-08-16 2021-02-23 青岛清原化合物有限公司 一种哒嗪醇类化合物及其衍生物、制备方法、除草组合物和应用
WO2021032033A1 (fr) * 2019-08-16 2021-02-25 青岛清原化合物有限公司 Composé de pyridazinol, dérivé de celui-ci, procédé de préparation correspondant, composition herbicide et utilisation associées
CN112390759B (zh) * 2019-08-16 2022-06-28 青岛清原化合物有限公司 一种哒嗪醇类化合物及其衍生物、制备方法、除草组合物和应用
CN111072671A (zh) * 2019-12-26 2020-04-28 浙江理工大学 一种5-溴-2-氯-7H-吡咯并[2,3-d]嘧啶的制备方法
CN113203815A (zh) * 2021-05-13 2021-08-03 黑龙江省农业科学院农产品质量安全研究所 基于uplc-msms检测糙米、稻壳和秸秆中氟酮磺草胺及其代谢物的方法

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