WO2017217553A1 - Composé d'oxime et herbicide - Google Patents

Composé d'oxime et herbicide Download PDF

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Publication number
WO2017217553A1
WO2017217553A1 PCT/JP2017/022424 JP2017022424W WO2017217553A1 WO 2017217553 A1 WO2017217553 A1 WO 2017217553A1 JP 2017022424 W JP2017022424 W JP 2017022424W WO 2017217553 A1 WO2017217553 A1 WO 2017217553A1
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Prior art keywords
alkyl
phenyl
halo
alkoxy
cycloalkyl
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PCT/JP2017/022424
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English (en)
Japanese (ja)
Inventor
沼田　昭
裕二 岩脇
有理 吉野
隆雄 宮崎
孝将 古橋
祐人 臼井
Original Assignee
日産化学工業株式会社
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Priority claimed from JP2016169574A external-priority patent/JP2019142777A/ja
Application filed by 日産化学工業株式会社 filed Critical 日産化学工業株式会社
Publication of WO2017217553A1 publication Critical patent/WO2017217553A1/fr

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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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
    • A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
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    • 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
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    • 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
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    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/36—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C07C259/02—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by halogen atoms
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    • C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
    • C07C259/14—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C271/34—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C—CHEMISTRY; METALLURGY
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    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C07C309/66—Methanesulfonates
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    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C333/02—Monothiocarbamic acids; Derivatives thereof
    • C07C333/04—Monothiocarbamic acids; Derivatives thereof having nitrogen atoms of thiocarbamic groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D233/61—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms
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    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
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Definitions

  • the present invention relates to a novel oxime compound or a salt thereof, and an agrochemical, particularly a herbicide, containing the oxime compound or a salt thereof as an active ingredient.
  • the agrochemical in the present invention means an insecticide / acaricide, nematicide, herbicide, fungicide, etc. in the field of agriculture and horticulture.
  • Patent Documents 1 to 4 disclose certain oxime compounds, but do not disclose any oxime compounds according to the present invention.
  • the object of the present invention is a highly safe and effective herbicide active ingredient that reliably shows effects on various weeds at a lower dose, and has reduced problems such as soil contamination and effects on subsequent crops. It is to provide useful chemical substances.
  • the novel oxime compound represented by the following formula (1) according to the present invention has excellent herbicidal activity as a herbicide and a target crop.
  • the present invention was completed by finding out that the compound is extremely useful and has almost no adverse effects on non-target organisms such as mammals, fish and beneficial insects.
  • R 3a And R 4a are each independently a hydrogen atom, C 1 ⁇ C 6 Alkyl, R 5g Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 3 ⁇ C 8 Cycloalkyl, C 2 ⁇ C 6 Alkenyl, C 2 ⁇ C 6 Alkynyl, phenyl, (Z b ) qb Represents phenyl, D2-104 or D2-105 substituted with R, or R 3a Is R 4a Together with C 2 ⁇ C 7
  • An alkylene chain or C 2 ⁇ C 7 By forming an alkenylene chain of R 3a And R 4a May form a 3- to 8-membered ring together with the nitrogen atom to which is bonded, and in this case, the alkylene chain or alkenylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and a halogen atom, cyano, C 1 ⁇ C 6 Alkyl, halo (C 1 ⁇
  • R 15 Is C 1 ⁇ C 8 Alkyl
  • R 20 Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 3 ⁇ C 8 Cycloalkyl, C 2 ⁇ C 6 Alkenyl, C 2 ⁇ C 6 Alkynyl, phenyl, (Z 1 ) q1 Represents phenyl, D1-1 to D1-42, D1-79, D1-81, D1-82, D1-84, D1-85, D1-91 to D1-99 or D1-100, substituted with R 16 Is a hydrogen atom, C 1 ⁇ C 8 Alkyl, R 20 Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 3 ⁇ C 8 Cycloalkyl, R 20 Optionally substituted with (C 3 ⁇ C 8 ) Cycloalkyl, C 2 ⁇ C 6 Alkenyl, R 20 Optionally substituted with (C 2 ⁇ C 6 ) Alkenyl, C 3 ⁇ C 8
  • A is a hydrogen atom, C 1 ⁇ C 6 Alkyl, R 5 Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 3 ⁇ C 8 Cycloalkyl, C 2 ⁇ C 6 Alkenyl, R 5 Optionally substituted with (C 2 ⁇ C 6 ) Alkenyl, C 2 ⁇ C 6 Alkynyl, R 5 Optionally substituted with (C 2 ⁇ C 6 ) Alkynyl, -S (O) r2 R 1a , -C (O) OR 1b , -C (S) OR 1c , -C (O) SR 1d , -C (S) SR 1e , -C (O) R 2 , -C (O) N (R 4a ) R 3a , -C (S) N (R 4a ) R 3a , -S (O) r2 N (R 4b ) R 3b , -P (
  • B represents a structure represented by either B-1-a or B-2-a, Z 4 , Z 6 And Z 8 Each independently represents a halogen atom, C 1 ⁇ C 6 Alkyl, C 3 ⁇ C 8 Cycloalkyl, C 2 ⁇ C 6 Alkynyl, C 1 ⁇ C 6 Alkoxy, halo (C 1 ⁇ C 6 ) Alkoxy, R 45 Optionally substituted with (C 2 ⁇ C 6 ) Alkynyl, phenyl, (Z 3 ) q3 Or an oxime compound according to the above [2], which represents phenyl, D3-2, D3-3, D3-7, D3-11, D3-22, D3-32, D3-33 or D3-34 substituted with Its salt.
  • B represents B-1-a
  • A is a hydrogen atom, C 1 ⁇ C 6 Alkyl, R 5 Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 2 ⁇ C 6 Alkenyl, C 2 ⁇ C 6 Alkynyl, -S (O) r2 R 1a , -C (O) OR 1b , -C (S) OR 1c , -C (O) SR 1d , -C (O) R 2 , -C (O) N (R 4a ) R 3a , -C (S) N (R 4a ) R 3a Or -S (O) r2 N (R 4b ) R 3b
  • R 1a Is C 1 ⁇ C 8 Alkyl, C 3 ⁇ C 8 Cycloalkyl or (Z a ) qa
  • R 1b is a hydrogen atom, C 1 ⁇ C 6 Alkyl, R 5b Optionally substituted with (C 1 ⁇
  • Z 4 Is a halogen atom, C 1 ⁇ C 6 Alkyl, C 1 ⁇ C 6 Alkoxy or halo (C 1 ⁇ C 6 ) Represents alkoxy
  • Z 6 Is a halogen atom, C 1 ⁇ C 6 Alkyl, C 3 ⁇ C 8 Cycloalkyl, C 2 ⁇ C 6 Alkynyl, R 45
  • B represents a structure represented by either B-1-b or B-2-b; Z 4 ' And Z 7 Each independently represents a halogen atom, C 3 ⁇ C 8 Cycloalkyl or (Z 3 ) q3
  • B represents B-1-b
  • A represents a hydrogen atom
  • R 6d represents R 6c And R 6d Represents a hydrogen atom
  • R 7 Is C 1 ⁇ C 6 Represents alkyl
  • R 8a Is a hydrogen atom or C 1 ⁇ C 6 Represents alkoxycarbonyl
  • R 9a , R 10 , R 11 And R 12 Represents a hydrogen atom
  • Z 3 represents a halogen atom, the oxime compound or a salt thereof according to the above [6].
  • Z 4 ' Is a halogen atom or C 3 ⁇ C 8 Represents cycloalkyl
  • Z 7 Is a halogen atom or (Z 3 ) q3
  • B is an oxime compound or a salt thereof according to any one of [1] or [2] above, wherein B represents B-1.
  • B is an oxime compound or a salt thereof according to any one of [1] or [2] above, wherein B represents B-2 or B-3.
  • B is an oxime compound or a salt thereof according to any one of [1] or [2] above, wherein B represents B-3.
  • Z is a halogen atom, C 1 ⁇ C 6 Alkyl, C 3 ⁇ C 8 Cycloalkyl, C 2 ⁇ C 6 Alkynyl, C 1 ⁇ C 6 Alkoxy, halo (C 1 ⁇ C 6 ) Alkoxy, phenyl, (Z 3 ) q3 Phenyl, D3-2, D3-3, D3-7, D3-11, D3-22, D3-32, D3-33 or D3-34 substituted with q, when q represents an integer of 2 or more,
  • the oxime compound or a salt thereof according to any one of [1], [2], and [9] to [11], wherein each Z may be the same as or different from each other.
  • Z is a halogen atom, C 1 ⁇ C 6 Alkyl, C 3 ⁇ C 8 Cycloalkyl, C 2 ⁇ C 6 Alkynyl, C 1 ⁇ C 6 Alkoxy or halo (C 1 ⁇ C 6 ) Represents alkoxy, and when q represents an integer of 2 or more, each Z may be the same as or different from each other, [1], [2], [9] to [11]
  • the oxime compound or a salt thereof according to any one of the above.
  • Z is C 1 ⁇ C 6 Alkyl, C 3 ⁇ C 8 Cycloalkyl, C 2 ⁇ C 6 Alkynyl or C 1 ⁇ C 6 Represents alkoxy, and when q represents an integer of 2 or more, each Z may be the same as or different from each other, any one of the above [1], [2], and [9] to [11]
  • Z is C 1 ⁇ C 6 Alkyl or C 1 ⁇ C 6 Represents alkoxy, and when q represents an integer of 2 or more, each Z may be the same as or different from each other, any one of the above [1], [2], and [9] to [11]
  • Z is C 1 ⁇ C 6 Any one of the above-mentioned [1], [2], and [9] to [11], wherein alkyl represents an integer of 2 or more, and each Z may be the same or different from each other The oxime compound or salt thereof according to claim 1.
  • Z is C 1 ⁇ C 6 Alkyl, phenyl, (Z 3 ) q3 Phenyl, D3-2, D3-3, D3-7, D3-11, D3-22, D3-32, D3-33 or D3-34 substituted with q, when q represents an integer of 2 or more,
  • the oxime compound or a salt thereof according to any one of [1], [2], and [9] to [11], wherein each Z may be the same as or different from each other.
  • Z is C 1 ⁇ C 6 Alkyl, phenyl or (Z 3 ) q3
  • q represents an integer of 2 or more
  • each Z may be the same as or different from each other.
  • the oxime compound or a salt thereof according to any one of [11].
  • Z is C 1 ⁇ C 6 Represents alkyl, D3-2, D3-3, D3-7, D3-11, D3-22, D3-32, D3-33 or D3-34, and when q represents an integer of 2 or more, each Z is The oxime compound or a salt thereof according to any one of [1], [2], [9] to [11], which may be the same as or different from each other.
  • B represents B-1-a.
  • B represents B-2-a.
  • B is an oxime compound or a salt thereof according to any one of [1], [2], and [6] above, wherein B represents B-1-b.
  • B is an oxime compound or a salt thereof according to any one of [1], [2], and [6] above, wherein B represents 2-b.
  • Z 4 Is a halogen atom, C 1 ⁇ C 6 Alkyl, C 3 ⁇ C 8 Cycloalkyl, C 2 ⁇ C 6 Alkynyl, C 1 ⁇ C 6 Alkoxy or halo (C 1 ⁇ C 6 )
  • the oxime compound or a salt thereof according to any one of [3] to [5], [20] and [21], which represents alkoxy.
  • Z 4 Is C 1 ⁇ C 6 Alkyl, C 1 ⁇ C 6 Alkoxy or halo (C 1 ⁇ C 6 ) The oxime compound or a salt thereof according to any one of [3] to [5], [20] and [21], which represents alkoxy.
  • Z 4 Is C 1 ⁇ C 6 Alkyl or C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of [3] to [5], [20], and [21], which represents alkoxy.
  • Z 4 Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of [3] to [5], [20], and [21], which represents alkyl.
  • Z 4 Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of [3] to [5], [20], and [21], which represents alkoxy.
  • Z 4 Represents an oxime compound or a salt thereof according to any one of [3] to [5], [20] and [21] above, which represents a halogen atom.
  • Z 4 Is C 3 ⁇ C 8 The oxime compound or a salt thereof according to any one of [3] to [5], [20] and [21], which represents cycloalkyl.
  • Z 8 Is a halogen atom, C 1 ⁇ C 6 Alkyl, C 3 ⁇ C 8 Cycloalkyl, C 2 ⁇ C 6 Alkynyl, C 1 ⁇ C 6 Alkoxy or halo (C 1 ⁇ C 6 ) The oxime compound or salt thereof according to any one of [3] to [5], [20], [21], and [24] to [30], which represents alkoxy.
  • Z 8 Is C 1 ⁇ C 6 Alkyl, C 1 ⁇ C 6 Alkoxy or halo (C 1 ⁇ C 6 ) The oxime compound or salt thereof according to any one of [3] to [5], [20], [21], and [24] to [30], which represents alkoxy.
  • Z 8 Is C 1 ⁇ C 6 Alkyl or C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of [3] to [5], [20], [21], and [24] to [30], which represents alkoxy.
  • Z 8 Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of [3] to [5], [20], [21], and [24] to [30], which represents alkyl.
  • Z 8 Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of [3] to [5], [20], [21], and [24] to [30], which represents alkoxy.
  • Z 6 Is a halogen atom, C 1 ⁇ C 6 Alkyl, C 3 ⁇ C 8 Cycloalkyl, C 2 ⁇ C 6 Alkynyl, phenyl, (Z 3 ) q3 [3] to [5], [3], [3], [D3], [D3], [D3], [D3-11], [D3-11], [D3] [20], [21], [24] to [35], the oxime compound or a salt thereof according to any one of [1].
  • Z 6 Is a halogen atom, C 1 ⁇ C 6 Alkyl, C 3 ⁇ C 8 Cycloalkyl, C 2 ⁇ C 6 The oxime compound or a salt thereof according to any one of [3] to [5], [20], [21], and [24] to [35], which represents alkynyl.
  • Z 6 Is a halogen atom, C 1 ⁇ C 6 Alkyl, C 2 ⁇ C 6 The oxime compound or a salt thereof according to any one of [3] to [5], [20], [21], and [24] to [35], which represents alkynyl.
  • Z 6 Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of [3] to [5], [20], [21], and [24] to [35], which represents alkyl.
  • Z 6 Is an oxime compound or a salt thereof according to any one of [3] to [5], [20], [21], and [24] to [35], which represents a halogen atom.
  • Z 6 Is phenyl, (Z 3 ) q3 [3] to [5], [3], [3], [D3], [D3], [D3], [D3-11], [D3-11], [D3] [20], [21], [24] to [35], the oxime compound or a salt thereof according to any one of [1].
  • Z 6 Is phenyl, (Z 3 ) q3
  • Z 7 Represents an oxime compound or a salt thereof according to any one of [6] to [8], [22], and [23] above, which represents a halogen atom.
  • A is a hydrogen atom, C 1 ⁇ C 6 Alkyl, R 5 Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 2 ⁇ C 6 Alkenyl, C 2 ⁇ C 6 Alkynyl, -S (O) r2 R 1a , -C (O) OR 1b , -C (S) OR 1c , -C (O) SR 1d , -C (O) R 2 , -C (O) N (R 4a ) R 3a , -C (S) N (R 4a ) R 3a Or -S (O) r2 N (R 4b ) R 3b
  • A is a hydrogen atom, C 1 ⁇ C 6 Alkyl, R 5 Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 3 ⁇ C 8 Cycloalkyl,
  • A is a hydrogen atom, C 1 ⁇ C 6 Alkyl, R 5 Optionally substituted with (C 1 ⁇ C 6 ) The oxime compound or a salt thereof according to any one of [1] to [45] above, which represents alkyl.
  • A is C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of [1] to [45] above, which represents alkyl.
  • A is R 5 Optionally substituted with (C 1 ⁇ C 6 ) The oxime compound or a salt thereof according to any one of [1] to [45] above, which represents alkyl.
  • A is -S (O) r2 R 1a , -C (O) OR 1b , -C (S) OR 1c , -C (O) SR 1d , -C (O) R 2 , -C (O) N (R 4a ) R 3a , -C (S) N (R 4a ) R 3a Or -S (O) r2 N (R 4b ) R 3b
  • A is —C (O) N (R 4a ) R 3a , -C (S) N (R 4a ) R 3a
  • the oxime compound or a salt thereof according to any one of the above [1] to [45] wherein [53] A is —C (O) N (R 4a ) R 3a ,
  • R 5 Is C 1 ⁇ C 6 Alkoxy (C 1 ⁇ C 6 ) The oxime compound or a salt thereof according to any one of [1] to [59], which represents alkoxy.
  • R 5 Is —OC (O) R 31 The oxime compound or a salt thereof according to any one of the above [1] to [59], wherein [65] R 1a Is C 1 ⁇ C 8 Alkyl, C 3 ⁇ C 8 Cycloalkyl or (Z a ) qa The oxime compound or a salt thereof according to any one of the above [1] to [64], which represents phenyl substituted with [66] R 1a Is C 1 ⁇ C 8 The oxime compound or a salt thereof according to any one of [1] to [64], which represents alkyl.
  • R 1a Is C 3 ⁇ C 8
  • R 1a (Z a ) qa The oxime compound or a salt thereof according to any one of the above [1] to [64], which represents phenyl substituted with [69]
  • R 1b Is C 1 ⁇ C 6 Alkyl, R 5b Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 2 ⁇ C 6 Alkenyl, phenyl or (Z b ) qb
  • R 1b Is phenyl or (Z b ) qb
  • R 1b Is
  • R 1b Is R 5b Optionally substituted with (C 1 ⁇ C 6 ) The oxime compound or a salt thereof according to any one of [1] to [68] above, which represents alkyl.
  • R 1b Is C 2 ⁇ C 6 The oxime compound or a salt thereof according to any one of [1] to [68], which represents alkenyl.
  • R 1c Is C 1 ⁇ C 8 Alkyl, R 5c Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 3 ⁇ C 8 Cycloalkyl, C 2 ⁇ C 6 Alkenyl, C 2 ⁇ C 6 The oxime compound or a salt thereof according to any one of [1] to [73], which represents alkynyl or phenyl.
  • R 1c Is an oxime compound or a salt thereof according to any one of [1] to [73] above, which represents phenyl.
  • R 1d Is C 1 ⁇ C 6 Alkyl, R 5d Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 2 ⁇ C 6 Alkenyl or C 3 ⁇ C 8
  • R 1d Is C 1 ⁇ C 6
  • R 2 Is C 1 ⁇ C 8 Alkyl, R 5f Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 3 ⁇ C 8 Cycloalkyl, R 5f Optionally substituted with (C 3 ⁇ C 8 ) Cycloalkyl, C 2 ⁇ C 6 Alkenyl, C 3 ⁇ C 8 Cycloalkenyl, C 2 ⁇ C 6 Alkynyl, C 1 ⁇ C 6 Alkylcarbonyl, benzoyl, phenyl, (Z f ) qf Any one of the above-mentioned [1] to [77], which represents phenyl, D2-32, D2-33, D2-34, D2-92, D2-93, D2-100 or D2-101 substituted with The oxime compound or a salt thereof described.
  • R 2 Is C 1 ⁇ C 8 Alkyl, R 5f Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 3 ⁇ C 8 Cycloalkyl, R 5f Optionally substituted with (C 3 ⁇ C 8 ) Cycloalkyl, C 2 ⁇ C 6 Alkenyl, C 3 ⁇ C 8 Cycloalkenyl, C 2 ⁇ C 6 Alkynyl, C 1 ⁇ C 6
  • the oxime compound or a salt thereof according to any one of [1] to [77], which represents alkylcarbonyl.
  • R 2 Is benzoyl, phenyl, (Z f ) qf Any one of the above-mentioned [1] to [77], which represents phenyl, D2-32, D2-33, D2-34, D2-92, D2-93, D2-100 or D2-101 substituted with The oxime compound or a salt thereof described.
  • R 2 Is C 1 ⁇ C 8 Alkyl, R 5f Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 3 ⁇ C 8 Cycloalkyl, R 5f Optionally substituted with (C 3 ⁇ C 8 ) The oxime compound or a salt thereof according to any one of [1] to [77] above, which represents cycloalkyl.
  • R 2 Is C 1 ⁇ C 8 Alkyl, R 5f Optionally substituted with (C 1 ⁇ C 6 ) The oxime compound or a salt thereof according to any one of [1] to [77] above, which represents alkyl.
  • R 2 Is C 3 ⁇ C 8 Cycloalkyl, R 5f Optionally substituted with (C 3 ⁇ C 8 ) The oxime compound or a salt thereof according to any one of [1] to [77] above, which represents cycloalkyl.
  • R 5b Is a halogen atom, C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of [1] to [83], which represents alkoxy or phenyl.
  • R 5b Is an oxime compound or a salt thereof according to any one of the above [1] to [83], which represents a halogen atom.
  • R 5b Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of [1] to [83], which represents alkoxy.
  • R 5b Is an oxime compound or a salt thereof according to any one of [1] to [83] above, which represents phenyl.
  • R 5c And R 5d Is an oxime compound or a salt thereof according to any one of [1] to [87] above, which represents phenyl.
  • R 5f Is a halogen atom, C 3 ⁇ C 8 Cycloalkyl, -OR f , Phenyl or (Z f ) qf
  • R 5f Is an oxime compound or a salt thereof according to any one of [1] to [88] above, which represents a halogen atom.
  • R 5f Is C 3 ⁇ C 8 The oxime compound or a salt thereof according to any one of [1] to [88], which represents cycloalkyl.
  • R 5f Is -OR f The oxime compound or a salt thereof according to any one of the above [1] to [88], wherein [93] R 5f Is phenyl or (Z f ) qf
  • R f Is phenyl or (Z f ) qf
  • the oxime compound or a salt thereof according to any one of the above [1] to [96] wherein [98] R 6 Is a halogen atom, —N (R 6c ) R 6d
  • [99] R 6 Is -N (R 6c ) R 6d The oxime compound or a salt thereof according to any one of the above [1] to [96], wherein [100] R 6 Is cyano,
  • R 6c Is a oxime compound or a salt thereof according to any one of [1] to [100] above, which represents a hydrogen atom.
  • R 6c Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of [1] to [100] above, which represents alkoxycarbonyl.
  • R 6c Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of [1] to [100] above, which represents alkylcarbonyl.
  • R 6d Is a oxime compound or a salt thereof according to any one of [1] to [104] above, which represents a hydrogen atom.
  • R 7 Is C 2 ⁇ C 6 The oxime compound or a salt thereof according to any one of [1] to [105], which represents alkenyl.
  • R 7 Is C 2 ⁇ C 6 The oxime compound or a salt thereof according to any one of [1] to [105], which represents alkynyl.
  • R 7b Is a halogen atom, C 3 ⁇ C 8 Cycloalkyl, C 1 ⁇ C 6
  • Z a Is a halogen atom, cyano, nitro, C 1 ⁇ C 6 Alkyl, halo (C 1 ⁇ C 6 ) Alkyl, C 1 ⁇ C 6 Alkoxy or halo (C 1 ⁇ C 6 )
  • the oxime compound or a salt thereof according to any one of [1] to [111] above, which represents alkoxy.
  • Z b Is a halogen atom, C 1 ⁇ C 6 Alkyl or C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of the above [1] to [112], which represents alkoxy.
  • Z f Is a halogen atom, cyano, nitro, 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 Alkylthio or C 1 ⁇ C 6
  • the oxime compound or a salt thereof according to any one of [1] to [113], which represents alkoxycarbonyl.
  • Z 3 Is a halogen atom, cyano, nitro, C 1 ⁇ C 6 Alkyl, halo (C 1 ⁇ C 6 ) Alkyl, C 1 ⁇ C 6 Alkoxy, halo (C 1 ⁇ C 6 ) Alkoxy or C 1 ⁇ C 6
  • R 8a Is a hydrogen atom, C 1 ⁇ C 6 Alkyl or C 1 ⁇ C 6
  • R 8a Is a oxime compound or a salt thereof according to any one of [1] to [116] above, which represents a hydrogen atom.
  • R 8a Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of the above [1] to [116], which represents alkyl.
  • R 8a Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of [1] to [116], which represents alkoxycarbonyl.
  • R 9a , R 10 , R 11 And R 12 Is an oxime compound or a salt thereof according to any one of [1] to [119] above, which represents a hydrogen atom.
  • R 31 Is C 1 ⁇ C 6 Alkoxy, C 3 ⁇ C 8 The oxime compound or a salt thereof according to any one of the above [1] to [120], which represents cycloalkyloxy or phenyl.
  • R 31 Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of the above [1] to [120], which represents alkoxy.
  • R 31 Is C 3 ⁇ C 8 The oxime compound or a salt thereof according to any one of the above [1] to [120], which represents cycloalkyloxy.
  • R 31 Is an oxime compound or a salt thereof according to any one of the above [1] to [120], which represents phenyl.
  • R 3a Is C 1 ⁇ C 6 Alkyl, C 2 ⁇ C 6 Represents alkenyl or phenyl, or R 3a Is R 4a Together with -CH 2 -CH 2 -CH 2 -CH 2 -, -CH 2 -CH 2 -CH 2 -CH 2 -Or-CH 2 -CH 2 -O-CH 2 -CH 2 -By forming R 3a And R 4a
  • the oxime compound according to any one of [1] to [121] above, which forms pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl together with a nitrogen atom to which is bonded Or a salt thereof.
  • R 3a Is C 1 ⁇ C 6 Alkyl, C 2 ⁇ C 6 The oxime compound or a salt thereof according to any one of [1] to [121], which represents alkenyl or phenyl.
  • R 3a Is R 4a Together with -CH 2 -CH 2 -CH 2 -CH 2 -, -CH 2 -CH 2 -CH 2 -CH 2 -Or-CH 2 -CH 2 -O-CH 2 -CH 2 -By forming R 3a And R 4a
  • R 4a Is C 1 ⁇ C 6 Alkyl or C 2 ⁇ C 6 The oxime compound or a salt thereof according to any one of [1] to [124], which represents alkenyl.
  • R 4a Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of [1] to [124], which represents alkyl.
  • R 4a Is C 2 ⁇ C 6 The oxime compound or a salt thereof according to any one of [1] to [124], which represents alkenyl.
  • R 3b Is C 1 ⁇ C 6 Represents alkyl or R 3b Is R 4b Together with -CH 2 -CH 2 -O-CH 2 -CH 2 -By forming R 3b And R 4b The oxime compound or a salt thereof according to any one of the above [1] to [127], which represents that morpholin-4-yl is formed together with a nitrogen atom to which is bonded.
  • R 3b Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of the above [1] to [127], which represents alkyl.
  • R 3b Is R 4b Together with -CH 2 -CH 2 -O-CH 2 -CH 2 -By forming R 3b And R 4b The oxime compound or a salt thereof according to any one of the above [1] to [127], which represents that morpholin-4-yl is formed together with a nitrogen atom to which is bonded.
  • R 4b Is a hydrogen atom or C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of [1] to [130], which represents alkyl.
  • R 4b Is a hydrogen atom or C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of [1] to [130], which represents alkyl.
  • R 4b Is a hydrogen atom or C 1 ⁇ C 6 The oxime compound or a salt thereof according to any one of [1] to [130], which represents alkyl.
  • X 3 Is an oxime compound or a salt thereof according to any one of [1] to [133] above, which represents a halogen atom.
  • An agrochemical containing, as an active ingredient, one or more selected from the oxime compounds according to any one of the above [1] to [134] and salts thereof.
  • a herbicide containing, as an active ingredient, one or more selected from the ketone and oxime compounds according to any one of [1] to [134] above and salts thereof.
  • the compound of the present invention has excellent herbicidal activity against various weeds and high safety against target crops, and has little adverse effect on non-target organisms such as mammals, fish and beneficial insects. Persistence and light environmental impact. Therefore, the present invention can provide a herbicide useful in the field of agriculture and horticulture such as paddy fields, upland fields, and orchards.
  • the keto-enol structure represented by the following formula derived from the structure of B in the formula (1) may be used in some cases. Although existence as a mutant is conceivable, the present invention includes all such structures.
  • the compound included in the present invention may have an E-isomer having an E configuration and a Z-isomer geometric isomer having a Z configuration depending on the type of substituent.
  • the present invention includes these E-form, Z-form, or a mixture containing E-form and Z-form in an arbitrary ratio. In the present specification, these are expressed as, for example, the combination of wavy lines as described below. To express.
  • the compounds included in the present invention include optically active substances resulting from the presence of one or more asymmetric carbon atoms, but the present invention includes all optically active substances or racemates.
  • this invention includes the salt of this invention compound represented by Formula (1).
  • compounds included in the present invention those that can be converted into acid addition salts according to a conventional method include, for example, hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, and the like.
  • Salt of inorganic acid such as salt, nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, salt of sulfonic acid such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, Salts of carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, succinic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid or the like
  • a salt of an amino acid such as glutamic acid or aspartic acid can be used.
  • those that can be converted into a metal salt according to a conventional method include, for example, alkali metal salts such as lithium, sodium, and potassium, and alkaline earth metals such as calcium, barium, and magnesium. It can be a salt or a salt of aluminum.
  • n- means normal
  • i- means iso
  • s- means secondary and tert- means tertiary
  • Ph means phenyl
  • examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • the notation “halo” also represents these halogen atoms.
  • C a -C b alkyl represents a linear or branched hydrocarbon group having a carbon number of a to b, for example, a methyl group, an ethyl group, an n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, tert-butyl group, n-pentyl group, 1,1-dimethylpropyl group, n-hexyl group, n-heptyl group, n- An octyl group etc. are mentioned as a specific example, and it selects in the range of each designated number of carbon atoms.
  • C a -C b alkenyl is a linear or branched chain composed of a to b carbon atoms and has one or more double bonds in the molecule.
  • Represents a saturated hydrocarbon group for example, vinyl group, 1-propenyl group, 2-propenyl group, 1-methylethenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 3-methyl-2-butenyl group, 1 , 1-dimethyl-2-propenyl group, 2-hexenyl group, 2-methyl-2-pentenyl group and the like are listed as specific examples, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkynyl represents a linear or branched chain having a carbon number of a to b and an unsaturated group having one or more triple bonds in the molecule.
  • Specific examples thereof include 1-methyl-2-butynyl group, 2-hexynyl group and the like, and each is selected within the range of the designated number of carbon atoms.
  • halo (C a -C b ) alkyl is linear or branched having a carbon number of a to b in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom
  • a chain-like hydrocarbon group is represented, and when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other.
  • fluoromethyl group chloromethyl group, bromomethyl group, iodomethyl group, difluoromethyl group, dichloromethyl group, trifluoromethyl group, chlorodifluoromethyl group, trichloromethyl group, bromodifluoromethyl group, 2-fluoroethyl group, 2- Chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2,2-trichloroethyl group, 1 , 1,2,2-tetrafluoroethyl group, 2-chloro-1,1,2-trifluoroethyl group, pentafluoroethyl group, 3,3,3-trifluoropropyl group, 2,2,3,3 , 3-pentafluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group
  • halo (C a -C b ) alkenyl in this specification refers to a straight or branched chain having a to b carbon atoms, in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom
  • An unsaturated hydrocarbon group which is chain-like and has one or more double bonds in the molecule.
  • these halogen atoms may be the same as or different from each other.
  • phenyl (C a -C b ) alkyl is a straight or branched chain having a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a phenyl group
  • a chain-like hydrocarbon group having the above-mentioned meaning is represented.
  • a benzyl group, a 1-phenethyl group and the like can be mentioned as specific examples, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b cycloalkyl represents a cyclic hydrocarbon group having a to b carbon atoms, and forms a monocyclic or complex ring structure having 3 to 6 members. I can do it.
  • Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms. Specific examples include cyclopropyl group, 1-methylcyclopropyl group, 2-methylcyclopropyl group, 2,2-dimethylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, etc. Selected in a range of numbers.
  • halo (C a -C b ) cycloalkyl in the present specification is a cyclic hydrocarbon group having a carbon number of a to b, wherein a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom It is possible to form a monocyclic or complex ring structure from 3 to 8 membered ring.
  • Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and the substitution with a halogen atom may be a ring structure part, a side chain part, They may be both, and when they are substituted by two or more halogen atoms, the halogen atoms may be the same as or different from each other.
  • 2,2-difluorocyclopropyl group, 2,2-dichlorocyclopropyl group, 2,2-dibromocyclopropyl group, 2,2-difluoro-1-methylcyclopropyl group, 2,2-dichloro-1-methyl Specific examples include cyclopropyl group, 2,2-dibromo-1-methylcyclopropyl group, 2,2,3,3-tetrafluorocyclobutyl group, etc., each selected within the range of the specified number of carbon atoms.
  • C a -C b cycloalkenyl represents a cyclic unsaturated hydrocarbon group having 1 to 2 carbon atoms and having 1 to 2 carbon atoms.
  • a monocyclic or complex ring structure from a member ring to an 8-member ring can be formed.
  • Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and the double bond may be in an endo- or exo- form.
  • Specific examples include 1-cyclopenten-1-yl group, 2-cyclopenten-1-yl group, 1-cyclohexen-1-yl group, 2-cyclohexen-1-yl group, and the like. Selected in a range of numbers.
  • halo (C a -C b ) cycloalkenyl in this specification refers to a cyclic structure having 1 to b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom, It represents an unsaturated hydrocarbon group having one or more double bonds, and can form a monocyclic or complex ring structure having 3 to 8 members. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and the double bond may be in an endo- or exo- form.
  • substitution by a halogen atom may be a ring structure part, a side chain part or both of them, and when substituted by two or more halogen atoms, those halogen atoms May be the same as or different from each other.
  • Specific examples include 2-fluoro-1-cyclopentenyl group, 2-chloro-1-cyclopentenyl group, 3-chloro-2-cyclopentenyl group, 2-fluoro-1-cyclohexenyl group, and the like. Selected within the specified number of carbon atoms.
  • C a -C b alkoxy in the present specification represents an alkyl-O— group having the above-mentioned meaning consisting of a to b carbon atoms, such as methoxy group, ethoxy group, n-propyloxy group, Specific examples include i-propyloxy group, n-butyloxy group, i-butyloxy group, s-butyloxy group, tert-butyloxy group and the like, and each is selected within the range of the designated number of carbon atoms.
  • halo (C a -C b ) alkoxy represents a haloalkyl-O— group having the above-mentioned meaning consisting of a to b carbon atoms, such as a difluoromethoxy group, a trifluoromethoxy group, Chlorodifluoromethoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2, -tetrafluoroethoxy group, 2-chloro Specific examples include -1,1,2-trifluoroethoxy group, 1,1,2,3,3,3-hexafluoropropyloxy group, and the like, each selected within the range of the designated number of carbon atoms. .
  • C a -C b cycloalkyloxy in the present specification represents a cycloalkyl-O— group having the above-mentioned meaning consisting of a to b carbon atoms, for example, cyclopropyloxy group, 2-methylcyclopentyl Specific examples include an oxy group, a cyclohexyloxy group, and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkoxy (C c -C d ) alkoxy represents a straight or branched chain in which the hydrogen atom bonded to a carbon atom has a carbon number of a to b.
  • a methoxymethoxy group, a 2-ethoxyethoxy group, a 2,2-dimethoxyethoxy group, and the like are given as specific examples, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkylthio in the present specification represents an alkyl-S-group having the above-mentioned meaning comprising a to b carbon atoms, for example, methylthio group, ethylthio group, n-propylthio group, i Specific examples include -propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, tert-butylthio group and the like, and each is selected within the range of the designated number of carbon atoms.
  • halo (C a -C b ) alkylthio represents a haloalkyl-S— group having the above-mentioned meaning consisting of a to b carbon atoms, such as a difluoromethylthio group, a trifluoromethylthio group, Chlorodifluoromethylthio group, bromodifluoromethylthio group, 2,2,2-trifluoroethylthio group, 1,1,2,2-tetrafluoroethylthio group, 2-chloro-1,1,2-trifluoroethylthio group Group, pentafluoroethylthio group, 1,1,2,3,3,3-hexafluoropropylthio group, heptafluoropropylthio group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl)
  • Specific examples include an ethylthio group, a nonafluorobutyl
  • C a -C b alkylsulfinyl in the present specification represents an alkyl-S (O) -group having the above-mentioned meaning consisting of a to b carbon atoms, such as methylsulfinyl group, ethylsulfinyl group, Specific examples include n-propylsulfinyl group, i-propylsulfinyl group, n-butylsulfinyl group, i-butylsulfinyl group, s-butylsulfinyl group, tert-butylsulfinyl group and the like. The range is selected.
  • halo (C a -C b ) alkylsulfinyl represents a haloalkyl-S (O) -group having the above-mentioned meaning consisting of a to b carbon atoms, such as a difluoromethylsulfinyl group, Trifluoromethylsulfinyl group, chlorodifluoromethylsulfinyl group, bromodifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethylsulfinyl
  • Specific examples include a group, a nonafluorobutylsulfinyl group, and the like, and each group is selected within the range of the designated number of carbon atoms.
  • C a -C b alkylsulfonyl in the present specification represents an alkyl-S (O) 2 -group having the above-mentioned meaning consisting of a to b carbon atoms, for example, methylsulfonyl group, ethylsulfonyl group , N-propylsulfonyl group, i-propylsulfonyl group, n-butylsulfonyl group, i-butylsulfonyl group, s-butylsulfonyl group, tert-butylsulfonyl group and the like. Selected in a range of numbers.
  • halo (C a -C b ) alkylsulfonyl represents a haloalkyl-S (O) 2 — group having the above-mentioned meaning consisting of a to b carbon atoms, for example, a difluoromethylsulfonyl group Trifluoromethylsulfonyl group, chlorodifluoromethylsulfonyl group, bromodifluoromethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 1,1,2,2-tetrafluoroethylsulfonyl group, 2-chloro-1 Specific examples include 1,2,2-trifluoroethylsulfonyl group and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkenylthio in the present specification represents an alkenyl-S— group having the above-mentioned meaning consisting of a to b carbon atoms, for example, 2-propenylthio group, 2-butenylthio group, Specific examples include 2-methyl-2-propenylthio group, 3-methyl-2-butenylthio group and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkenylsulfinyl represents an alkenyl-S (O) -group having the above-mentioned meaning consisting of a to b carbon atoms, for example, 2-propenylsulfinyl group, 2- Specific examples include a butenylsulfinyl group, a 2-methyl-2-propenylsulfinyl group, a 3-methyl-2-butenylsulfinyl group, and the like, and each selected within the range of the designated number of carbon atoms.
  • C a -C b alkenylsulfonyl in the present specification represents an alkenyl-S (O) 2 -group having the above-mentioned meaning consisting of a to b carbon atoms, for example, 2-propenylsulfonyl group, 2 Specific examples include -butenylsulfonyl group, 2-methyl-2-propenylsulfonyl group, 3-methyl-2-butenylsulfonyl group and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkynylthio represents an alkynyl-S— group having the above-mentioned meanings consisting of a to b carbon atoms, for example, ethynylthio group, 1-propynylthio group, 2- Specific examples include a propynylthio group, a 1-methyl-2-propynylthio group, a 2-butynylthio group, and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkynylsulfinyl represents an alkynyl-S (O) -group having the above-mentioned meaning consisting of a to b carbon atoms, such as ethynylsulfinyl group, 1-propynylsulfinyl.
  • Specific examples include a group, 2-propynylsulfinyl group, 1-methyl-2-propynylsulfinyl group, 2-butynylsulfinyl group, and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkynylsulfonyl represents an alkynyl-S (O) 2 -group having the above-mentioned meaning consisting of a to b carbon atoms, for example, ethynylsulfonyl group, 1-propynyl
  • Specific examples include a sulfonyl group, a 2-propynylsulfonyl group, a 1-methyl-2-propynylsulfonyl group, a 2-butynylsulfonyl group, and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkylcarbonyl in the present specification represents an alkyl-C (O) — group having the above-mentioned meaning comprising a to b carbon atoms, for example, an acetyl group, a propionyl group, a butyryl group.
  • Specific examples thereof include isobutyryl group, valeryl group, isovaleryl group, 2-methylbutanoyl group, pivaloyl group, hexanoyl group, heptanoyl group and the like, and each is selected in the range of the designated number of carbon atoms.
  • halo (C a -C b ) alkylcarbonyl represents a haloalkyl-C (O) -group having the above-mentioned meaning consisting of a to b carbon atoms, such as fluoroacetyl group, chloro Acetyl group, difluoroacetyl group, dichloroacetyl group, trifluoroacetyl group, chlorodifluoroacetyl group, bromodifluoroacetyl group, trichloroacetyl group, pentafluoropropionyl group, heptafluorobutanoyl group, 3-chloro-2,2-dimethyl
  • Specific examples include a propanoyl group and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkoxycarbonyl represents an alkyl-O—C (O) — group having the above-mentioned meanings consisting of a to b carbon atoms, for example, methoxycarbonyl group, ethoxycarbonyl Specific examples include a group, n-propyloxycarbonyl group, i-propyloxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, tert-butoxycarbonyl group and the like. Selected.
  • halo (C a -C b ) alkoxycarbonyl in the present specification represents a haloalkyl-O—C (O) — group having the above-mentioned meaning consisting of a to b carbon atoms, for example, chloromethoxycarbonyl Group, 2-chloroethoxycarbonyl group, 2,2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 2,2,2-trichloroethoxycarbonyl group and the like. Selected within the specified number of carbon atoms.
  • C a -C b alkylaminocarbonyl represents a carbamoyl group in which one of the hydrogen atoms is substituted with an alkyl group having the above-mentioned meaning consisting of a to b carbon atoms, for example, methylcarbamoyl
  • alkyl group having the above-mentioned meaning consisting of a to b carbon atoms for example, methylcarbamoyl
  • Specific examples include a group, ethylcarbamoyl group, n-propylcarbamoyl group, i-propylcarbamoyl group, n-butylcarbamoyl group, i-butylcarbamoyl group, s-butylcarbamoyl group, tert-butylcarbamoyl group, etc. Is selected within the range of the specified number of carbon atoms.
  • di (C a -C b ) alkylaminocarbonyl means in the above meaning that the number of carbon atoms which may be the same or different from each other is a to b.
  • Specific examples include a group, N, N-di (n-butyl) carbamoyl group, and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkylamino in the present specification represents an amino group in which one of the hydrogen atoms is substituted with an alkyl group having the above-mentioned meaning consisting of a to b carbon atoms, for example, a methylamino group , Ethylamino group, n-propylamino group, i-propylamino group, n-butylamino group, i-butylamino group, tert-butylamino group and the like. Selected by range.
  • di (C a -C b ) alkylamino has the above-mentioned meaning that the number of carbon atoms in which both hydrogen atoms may be the same or different from each other consists of a to b.
  • Specific examples include an amino group, a di (n-butyl) amino group, and the like, and each is selected within the range of the designated number of carbon atoms.
  • each substituent is a hydrogen atom bonded to a carbon atom
  • R A cycloalkyl group having the above-mentioned meanings consisting of a to b carbon atoms substituted with 5 or the like is selected and selected in the range of each designated number of carbon atoms. In this case, when there are two or more substituents, the substituents may be the same or different from each other, and the substitution position may be a ring structure part, a side chain part, or May be in both.
  • “By R 3a is to form the alkenylene chain of the alkylene chain or C 2 ⁇ C 7 of C 2 ⁇ C 7 together with R 4a, 3 ⁇ 8-membered ring together with the nitrogen atom to which R 3a and R 4a are bonded
  • the alkylene chain or alkenylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and is a halogen atom, 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 alkylthio, halo (C 1 -C 6 ) alkylthio, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl, phenyl, may be optionally substituted by oxo or thioxo ","
  • R 3b is an alkylene chain
  • the active compound included in the present invention include compounds shown in Tables 1 and 2.
  • the compounds in Tables 1 and 2 are for illustrative purposes, and the present invention is not limited to these.
  • the substituent described as Me represents a methyl group
  • Et represents an ethyl group
  • n-Pr and Pr-n represent normal propyl groups
  • i-Pr and Pr— i is an isopropyl group
  • c-Pr and Pr-c are cyclopropyl groups
  • n-Bu and Bu-n are normal butyl groups
  • s-Bu and Bu-s are secondary butyl groups
  • i-Bu and Bu -I is an isobutyl group
  • t-Bu and Bu-t are tertiary butyl groups
  • c-Bu and Bu-c are cyclobutyl groups
  • n-Pen and Pen-n are normal pentyl groups
  • c-Pen and Pen-c is a cyclopentyl group
  • n-Hex and Hex-n are normal hexyl groups
  • c-Hex and Hex-c are cyclohexyl groups
  • the descriptions -37, D3-38, D3-39 and D3-108 represent the following structures.
  • the numbers described in the above structural formula represent the substitution position of the substituent X 3 or Z 3.
  • the description “D3-7 [4-Cl]” is “4-chloropyrazole” -1-yl group ".
  • the descriptions A1a to A1y, A2a to A2z, A3a to A3e, A4a to A4w, and A4x represent the following structures.
  • the numbers described in the above structural formulas represent substitution positions of the substituents Z a , Z b , Z f or X 2.
  • a 1 is, C 1 ⁇ C 6 alkyl, R optionally substituted with 5 (C 1 ⁇ C 6) alkyl, C 3 ⁇ C 8 cycloalkyl, optionally substituted with R 5 (C 3 ⁇ C 8) cycloalkyl, C 2 ⁇ C 6 alkenyl, optionally substituted with R 5 (C 2 ⁇ C 6 ) alkenyl, C 3 ⁇ C 8 cycloalkenyl, optionally substituted with R 5 (C 3 to C 8 ) cycloalkenyl, C 2 to C 6 alkynyl, (C 2 to C 6 ) alkynyl optionally substituted with R 5 , —S (O) r 2 R 1a , —C (O) OR 1b , — C (S) OR 1c , —C (O) SR 1d , —C (S) SR 1e , —C (O)
  • R 1a , R 1b , R 1c , R 1d , R 1e , R 2 , R 3a , R 3b , R 4a , R 4b , R 5 , r2, Q, R 6 , R 8a , R 9a , Z And q represent the same meaning as described above.
  • the compound represented by formula (1-3) and the compound represented by formula (7) may be reacted in the presence of a base in some cases to obtain a compound represented by formula (1-1).
  • the compound of the present invention and the compound of the present invention represented by the formula (1-2) can be produced.
  • Some of the compounds represented by formula (7) are known compounds, and some of them are commercially available.
  • the amount of the compound represented by formula (7) can be used in the range of 0.5 to 50 equivalents relative to 1 equivalent of the compound represented by formula (1-3).
  • the amount of the base that can be used can be used in the range of 0.5 to 50 equivalents with respect to 1 equivalent of the compound represented by the formula (1-3).
  • This reaction may be carried out without a solvent, but a solvent may be used, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2- Polar solvents such as imidazolinone, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride Halogenated hydrocarbons such as chloroform and carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane.
  • a solvent may be used, for example
  • the reaction temperature can be set to any temperature from ⁇ 80 ° C. to the reflux temperature of the reaction mixture.
  • the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set in the range of 5 minutes to 100 hours.
  • Manufacturing method B (In the formula, Q, R 6 , R 8a , R 9a , Z and q have the same meaning as described above.)
  • the compound of the present invention represented by the formula (1-3) by reacting the compound represented by the formula (9) and the compound represented by the formula (10) in the presence of a base in some cases [following This is abbreviated as compound (1-3). Can be manufactured.
  • Some of the compounds represented by formula (9) are known compounds. Others can also be produced according to known methods described in, for example, International Publication No. 2009/019005.
  • Some of the compounds represented by formula (10) are known compounds. Others can also be produced according to known methods described in, for example, Chemical Communications, (2011), 47 (27), page 7848.
  • the amount of the compound represented by formula (10) can be used in the range of 0.5 to 50 equivalents relative to 1 equivalent of the compound represented by formula (9).
  • the amount of the base that can be used can be used in the range of 0.5 to 50 equivalents with respect to 1 equivalent of the compound represented by the formula (9).
  • This reaction may be carried out without a solvent, but a solvent may be used, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2- Polar solvents such as imidazolinone, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride Halogenated hydrocarbons such as chloroform and carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane.
  • a solvent may be used, for example,
  • the reaction temperature can be set to any temperature from ⁇ 80 ° C. to the reflux temperature of the reaction mixture.
  • the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set in the range of 5 minutes to 100 hours.
  • the reaction can be carried out in the presence of an acid such as hydrochloric acid, sulfuric acid or p-toluenesulfonic acid or a base such as sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate.
  • an acid such as hydrochloric acid, sulfuric acid or p-toluenesulfonic acid or a base such as sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate.
  • the amount that can be used can be used in the range of 0.5 to 50 equivalents relative to 1 equivalent of the compound represented by Formula (1-3-1).
  • the reaction temperature can be set to any temperature from ⁇ 80 ° C. to the reflux temperature of the reaction mixture.
  • the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set in the range of 5 minutes to 100 hours.
  • Manufacturing method D (In the formula, Q, R 6 , R 8a , R 9a , Z and q have the same meaning as described above.)
  • the compound represented by the formula (11) By reacting the compound represented by the formula (11) with the compound represented by the formula (10-2) according to a known method described in, for example, International Publication No. 2016/098899, the compound ( 1-3) can be produced.
  • Some of the compounds represented by formula (11) are known compounds. Others can also be produced according to known methods described in, for example, International Publication No. 2016/098899.
  • Some of the compounds represented by formula (10-2) are known compounds, and some of them are commercially available. Others can also be produced according to known methods described in the literature.
  • Manufacturing method I (In the formula, A, Q, R 8a , R 9a , Z and q represent the same meaning as described above, and R 101 represents C 1 -C 6 alkyl.)
  • the compound represented by the formula (1-4-1) which can be produced by the production method A or the production method B, according to a known method described in, for example, International Publication No. 2012/108511
  • the compound of the present invention represented by the formula (1-4-2) can be produced.
  • Manufacturing method J (In the formula, A, Q, R 8a , R 9a , Z and q have the same meaning as described above.)
  • the compound represented by the formula (1-4-2) By reacting the compound represented by the formula (1-4-2) according to a known method described in, for example, International Publication No. 2014/007395, etc., via the formula (1-4-2b)
  • the compound of the present invention represented by the formula (1-4-3) can be produced.
  • Manufacturing method K (In the formula, A, Q, R 8a , R 9a , Z and q have the same meaning as described above.)
  • the compound of the present invention represented by the formula (1-5) can be obtained by subjecting the compound represented by (1-4-3) to a dehydration reaction.
  • This reaction may be carried out without a solvent, but a solvent may be used, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2- Amide solvents such as imidazolinone, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, chloride Halogenated hydrocarbons such as methylene, chloroform and carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane.
  • a solvent may be used, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide,
  • solvents may be used alone or as a mixture of two or more thereof.
  • the reaction can be carried out in the presence of an acid such as hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, thionyl chloride, phosphoryl chloride, trifluoroacetic anhydride, trichloroacetyl chloride and the like.
  • an acid such as hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, thionyl chloride, phosphoryl chloride, trifluoroacetic anhydride, trichloroacetyl chloride and the like.
  • the amount that can be used can be used in the range of 0.5 to 200 equivalents relative to 1 equivalent of the compound represented by the formula (1-4-3).
  • the amount of the base that can be used can be used in the range of 0.5 to 200 equivalents relative to 1 equivalent of the compound represented by formula (1-4-3).
  • the reaction temperature can be set to any temperature from ⁇ 80 ° C. to the reflux temperature of the reaction mixture.
  • the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set in the range of 5 minutes to 100 hours.
  • Manufacturing method L (In the formula, A 1 , Q, R 8a , R 9a , R 101 , J a , Z and q have the same meaning as described above.)
  • the compound represented by the formula (1-1) and the compound represented by the formula (14) are reacted with each other.
  • the compound of the present invention represented by -2) can be produced.
  • Some of the compounds represented by formula (14) are known compounds, and some of them are commercially available. Others can also be produced according to known methods described in the literature. In this reaction, the amount of the compound represented by formula (14) can be used in the range of 0.5 to 200 equivalents relative to 1 equivalent of the compound represented by formula (1-6-1).
  • the amount of the base that can be used can be used in the range of 0.5 to 200 equivalents relative to 1 equivalent of the compound represented by the formula (1-6-1).
  • This reaction may be carried out without a solvent, but a solvent may be used, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2- Amide solvents such as imidazolinone, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, chloride Halogenated hydrocarbons such as methylene, chloroform and carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane.
  • a solvent may be used, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide,
  • the reaction temperature can be set to any temperature from ⁇ 80 ° C. to the reflux temperature of the reaction mixture.
  • the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set in the range of 5 minutes to 100 hours.
  • Manufacturing method M (In the formula, A, Q, R 8a , R 9a , R 101 , Z and q have the same meaning as described above.)
  • the present invention represented by the formula (1-6) Compounds can be produced.
  • the compound represented by Formula (10) used in Production Method B the compound represented by Formula (10-3) can be produced, for example, according to the production method described in Reaction Scheme 1.
  • Reaction example 1 (In the formula, R 7 , R 8a , R 9a and R 101 have the same meaning as described above.)
  • the compound represented by the formula (10-1) By reacting the compound represented by the formula (10-1) and the compound represented by the formula (10-2) according to a known method described in, for example, International Publication No. 2006/084031, etc.
  • the compound represented by the formula (10-3) can be produced.
  • Some of the compounds represented by formula (10-1) are known compounds, and some of them are commercially available. Others can also be produced according to known methods described in the literature.
  • Some of the compounds represented by formula (10-2) are known compounds, and some of them are commercially available. Others can also be produced according to known methods described in the literature.
  • the reaction from production method A to production method M may be performed in an inert gas atmosphere such as nitrogen or argon if necessary.
  • the reaction mixture after completion of the reaction is directly concentrated or dissolved in an organic solvent, concentrated after washing with water, or poured into ice water and concentrated after extraction with an organic solvent, followed by normal post-treatment.
  • the objective compound of the present invention can be obtained.
  • it can be separated and purified by any purification method such as recrystallization, column chromatograph, thin layer chromatograph, liquid chromatographic fractionation and the like.
  • the compound of the present invention can be used as a herbicide for paddy fields in any treatment method of soil treatment and foliage treatment under flooded water.
  • paddy weeds for example, weeping family (Potamogetonaceae) weeds represented by roundleaf ⁇ pondweed, Potamogeton distinctus, etc.
  • Algiataceae Algiataceae (Alismataceae) weeds, such as Sagittaria trifolia, Azegaya (chinese sprangletop, Leptochloa chinensis), Onidaseya (bearded sprangletop, Leptochloa fascicularis), Barnyard grass, Echinochgal ), Tainubie (late watergrass, Echinochloa oryzicola), Taiwan sea oyster (southern cutgrass, Leersia hexandra), Sea oyster (Homalocenchrus japonocus) Red-leaf millet (broadleaf signalgrass, Brachiaria platyphylla), Alexandergrass, Brachiaria plantaginea, Onihishiba (large crabgrass, Digitaria sanguinalis), Oriza sativa, bermuda grass, Cynodon dactylon, giant cricket (fall) panicum, Panicum dichotomiflorum) globe fringerush,
  • Hythraceae (Lythraceae) weeds represented by Ammannia multiflora and Kumashigusa (Indian toothcup, Rotala indica) etc. (Oenotheraceae) Weed, Abnomome (rushlike dopatrium, Dopatrium junceum), Giant Abnomome (Gratiola japonica), Chrysanthemum (dwarf ambulia, Limnophila sessilifolia), Azena (prostrate false pimpernel, Lindernia pyxidna) Represented Leguminosae (Scrophulariaceae) weeds, Leguminosae (Leguminosae) weeds, Alger terridium terridium ideals Amaranthaceae weeds represented by spiny amaranth, Amaranthus spinosus, etc.
  • Weeds represented by water acepepper, Polygonum hydropiper, etc. Polygonaceae weeds, representatives of Gooseweed, Sicaclea ze, etc. Sphenocleaceae weeds, Swamp morningglory, Ipomoea aquatica, and other species such as Convolvulaceae weeds, Densosou (Marsileaceae), such as water clover and Marsilea minuta American Sendangsa (devil's beggartick s, Bidens frondosa), Takasaburo (false daisy, Eclipta prostrata), Cuckoo thistle (goatweed, Ageratumzoconyzoides), Takokogi (three-lobe beggarticks, Bidens tripartita), and the like, including Asteraceae weeds.
  • Convolvulaceae weeds such as water clover and Marsilea minuta American Sendangsa (devil's beggartick s, Bi
  • the compound of the present invention can be used as a herbicide for upland fields and orchards in any treatment method of soil treatment, soil admixture treatment, and foliage treatment.
  • upland weeds include solanaceae weeds such as black owl (black nightshade, Solanum nigrum) and white moth (jimsonweed, Datura stramonium), and so on.
  • Geraniaceae weeds velvetleaf, Abutilon theophrasti, and American stag beetle (prickly sida, Sida spinosa), and other common mallow (Malvaceae) weeds, malva asagao (tall morning-glory, reareappu) Morning glory (Ipomoea spps.)
  • morning glory ivyleaf morning-glory, Ipomoea hederacea
  • kogaigao japanese bindweed
  • Calystegia hederacea purple amaranth, Amaranthus lividus) redroot pigweed, Amaranthus retroflexus, Amaranthus tuberculatus, Amaranthus retroflexus, Amaranthaceae weeds, vancou burs, common burs Ragweed (common ragweed, Ambrosia artemisiaefolia), giant ragweed (giant ragweed, Ambrosia trifi
  • Plantaceae Plantaceae (Plantaginaceae) weeds, camellia (asiatic dayflower, Commelina communis) and bumblebees (Benghal dayflowe, Commelina benghalensis) Labiatae weeds, such as deadnettle, Lamium purpureum, etc., Drosophila (wild poinsettia, Euphorbia heterophylla), Euphorbia supina, and Spodoptera (spotted spurge, Euphorbia maculata) (Euphorbiaceae) Weeds, Yemgras (false cleavers, Galium spurium), Rubiaceae weeds represented by Asian madder, Rubia akane, etc., representatives of pansy, Viola tricolor, violet (Viola mandshurica), etc.
  • Violaceae weeds Leguminosae Fabaceae weeds, such as Hemp ⁇ sesbania, Sesbania exaltata, and Ebisusa (sicklepod, Cassia obtusifolia) Broad-leaved weeds such as Oxsaldaseae represented by (creeping woodsorrel, Oxsalis courniculata).
  • Wild sorghum (Sorgham bicolor), green foxtail (fall panicum, Panicum dichotomiflorum), shutter cane (shattercane, Sorgham bicolor), Johnson grass (johnson grass, Sorghum halepense), barnyard grass, loEchinochlia , Japanese squirrel (cockspur grass, Echinochloa crus-galli ⁇ var.
  • the compound of the present invention is a non-agricultural material that needs to control the growth of weeds such as turf, playground, open space, roadside, city holidays, and track ends in addition to the fields of agriculture and horticulture such as paddy fields, upland fields and orchards.
  • Land, or dike slopes, riverbeds, road shoulders and slopes, railway floors, park green spaces, grounds, parking lots, airports, factories and storage facilities, fallow land, or gardens, grass It can be used in any treatment method of soil treatment, soil admixing treatment, and foliage treatment in the ground, turf land, forestry land and the like.
  • the weeds include, but are not limited to, the blue spider (annualsbluegrass, Poa annua), the dandelion, Taraxacum officinale, the hairy fleabane, Conyza bonariensis, Conyza sumatrensis), Japanese wormwood (horseweed) green kyllinga, Cyperus brevifolius, Kyllinga brevifolia), horsetail (field horsetail, Equisetum arvense) and the like.
  • the blue spider annualsbluegrass, Poa annua
  • the dandelion Taraxacum officinale
  • the hairy fleabane Conyza bonariensis
  • Conyza sumatrensis Conyza sumatrensis
  • Japanese wormwood (horseweed) green kyllinga Cyperus brevifolius
  • Kyllinga brevifolia Kyllinga brevifolia
  • horsetail field horsetail, Equisetum arvense
  • the compound of the present invention can control undesired plant growth relative to useful plants.
  • useful plants include field crops, paddy field crops, horticultural crops, turf, fruit trees, etc., specifically, for example, corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut.
  • Crops such as buckwheat, sugar beet, rapeseed, sunflower, sugarcane and tobacco; solanaceous vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), cucurbitae vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), oilseed rape Vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, garlic, artichoke, lettuce, etc.), liliaceae vegetables (green onion, onion, garlic, asparagus) ), Celery family vegetables (carrot, parsley, celery, America Ufu, etc.), red crustacean vegetables (spinach, chard, etc.), perilla (vegetables, mint, basil, etc.), strawberry, sweet potato, yam, taro, etc .; fruits (apples, pears, Japanese pears, karin) , Quince, etc
  • Trees other than fruit trees such as croton, masaki and kanamochi; Shiba (Noshiba, Kourashiba, etc.), Bermudagrass (Gyogishiba, etc.), Bentgrass (Konukagusa, Hykonukagusa, Itokonukagusa, etc.), Bluegrass (Nagahagusa, Giant) Sparrows, etc.), fescues (such as Eurythus japonicus, duckweeds, etc.), ryegrass (such as mud wheat and barley), lawns such as hemlock and prickly crabs; oil crops such as oil palm and oilseed moth; Carne , Chrysanthemum, eustoma, gypsophila, gerbera, marigold, salvia, petunia, verbena, tulip, aster, gentian, lily, pansy, cyclamen, orchid, lily of the valley, lavender, stock,
  • useful plants in the present specification include HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors such as glyphosate, and glutamine synthetase inhibitors such as glufosinate.
  • HPPD inhibitors such as isoxaflutol
  • ALS inhibitors such as imazetapyr and thifensulfuron methyl
  • EPSP synthase inhibitors such as glyphosate
  • glutamine synthetase inhibitors such as glufosinate.
  • Tolerance to acetyl-CoA carboxylase inhibitors such as cetoxydim
  • PPO inhibitors such as flumioxazin
  • herbicides such as bromoxynil, dicamba and 2,4-D
  • 2,4-D also includes horticultural plants.
  • Examples of agricultural and horticultural plants that have been rendered tolerant by classical breeding methods include rapeseed, wheat, sunflower, rice and corn that are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapil. Already sold under the brand name.
  • SR corn and the like are examples of agricultural and horticultural plants imparted with resistance to acetyl-CoA carboxylase inhibitors such as trion oxime and aryloxyphenoxypropionic acid herbicides by classical breeding methods.
  • Agro-horticultural plants tolerated by acetyl-CoA carboxylase inhibitors are Procedures of the National Academy of Sciences of the United States of America (Proc.Natl.Acad) Sci. USA) 87, 7175-7179 (1990).
  • a plant resistant to an acetyl-CoA carboxylase inhibitor can be produced by introducing a mutation associated with imparting resistance into a plant by introducing a mutation into the plant acetyl-CoA carboxylase.
  • nucleic acid introduced with base substitution mutation represented by chimera plastic technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes.
  • Plants resistant to acetyl-CoA carboxylase inhibitors / herbicides can be created by inducing site-specific amino acid substitution mutations in the target) gene.
  • Examples of agricultural and horticultural plants that have been rendered tolerant by genetic recombination technology include glyphosate-resistant corn, soybean, cotton, rapeseed, and sugar beet varieties. RoundupReady (trade name) AgrisureGT) (brand name) and other brand names are already sold. Similarly, there are glufosinate-tolerant corn, soybean, cotton and rapeseed varieties by genetic recombination technology, which are already sold under trade names such as Liberty Link (trade name). Similarly, bromoxynyl-resistant cotton using genetic recombination technology is already sold under the brand name BXN.
  • the agricultural and horticultural plants also include plants that can synthesize selective toxins known in the genus Bacillus using genetic recombination techniques.
  • insecticidal toxins expressed in such genetically modified plants include insecticidal proteins derived from Bacillus cereus and Bacillus popilliae; Cry1Ab derived from Bacillus thuringiensis , Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C and other ⁇ -endotoxins, VIP1, VIP2, VIP3, VIP3A and other insecticidal proteins; nematode-derived insecticidal proteins; scorpion toxin, spider toxin, bee toxin or Toxins produced by animals such as insect-specific neurotoxins; filamentous fungi toxins; plant lectins; agglutinins; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatins, papain inhibitors; ricin, corn- Ribosome inactivating protein (RIP) such as RIP, abrin, saporin,
  • toxins expressed in such genetically modified plants Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C and other ⁇ -endotoxin proteins, VIP1, VIP2, VIP3, VIP3A and other insecticidal proteins
  • Hybrid toxins, partially defective toxins, and modified toxins are also included.
  • Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques.
  • Cry1Ab lacking a part Cry1Ab lacking a part of the amino acid sequence is known.
  • the modified toxin one or more amino acids of the natural toxin are substituted.
  • Examples of these toxins and recombinant plants capable of synthesizing these toxins include, for example, EP-A-0374753, WO93 / 07278, WO95 / 34656, EP-A-0427529, EP-A-451878, WO03 / 052073, etc. It is described in the patent literature. Toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Diptera pests, and Lepidoptera pests. In addition, genetically modified plants that contain one or more insecticidal insect resistance genes and express one or more toxins are already known, and some are commercially available.
  • Examples of these genetically modified plants include YieldGard (trade name) (a corn variety that expresses Cry1Ab toxin), YieldGard Rootworm (trade name) (a corn variety that expresses Cry3Bb1 toxin), YieldGard Plus (trade name) (a corn variety that expresses Cry1Ab and Cry3Bb1 toxins), Herculex I (trade name) (phosphino to confer resistance to Cry1Fa2 toxin and glufosinate Corn varieties expressing tricine N-acetyltransferase (PAT), NuCOTN33B (trade name) (cotton varieties expressing Cry1Ac toxin), Volgard I (trade name) (cotton varieties expressing Cry1Ac toxin), Bollgard II (trade name) (cotton varieties expressing Cry1Ac and Cry2Ab toxins), VIPCOT (trade name) (VIP toxin Expressed cotton varieties), NewLeaf (trade name) (potato varieties expressing Cry
  • the useful plants include those that have been imparted with the ability to produce an anti-pathogenic substance having a selective action using genetic recombination techniques.
  • anti-pathogenic substances include PR proteins (PRPs, described in EP-A-0392225); sodium channel inhibitors, calcium channel inhibitors (virus-produced KP1, KP4, KP6 toxins, etc.) Ion channel inhibitors; stilbene synthase; bibenzyl synthase; chitinase; glucanase; peptide antibiotics, heterocyclic antibiotics, protein factors involved in plant disease resistance (called plant disease resistance genes) And substances produced by microorganisms such as those described in WO03 / 000906).
  • Such anti-pathogenic substances and genetically modified plants that produce them are described in EP-A-0392225, WO95 / 33818, EP-A-0353191, and the like.
  • the useful plants include crops to which useful traits such as oil component modification and amino acid content enhancing traits have been imparted using genetic recombination techniques. Examples include VISTIVE (trade name) (low linolenic soybean with reduced linolenic content) or high-lysine (hig hoil) corn (corn with increased lysine or oil content).
  • the compound of the present invention may be mixed and applied with other types of herbicides, various insecticides, fungicides, plant growth regulators, synergists, and the like, as necessary, during formulation or spraying.
  • herbicides various insecticides, fungicides, plant growth regulators, synergists, and the like
  • cost reduction due to a decrease in the amount of applied medicine expansion of the herbicidal spectrum due to the synergistic action of the mixed drugs, and higher herbicidal effects can be expected.
  • a combination with a plurality of known herbicides is also possible.
  • Preferred herbicides for use in combination with the compounds of the present invention include, for example, acetochlor, acifluorfen, acronifen, alachlor, alloxydim, alloxydim sodium (Alloxydim-sodium), amethrin (ametryn), amicarbazone, amidosulfuron, aminocyclopirachlor, aminocyclopirachlor salts and esters (aminocyclopirachlor-salts and esters), aminopyralid ), Salts and esters of aminopyralid (aminopyralid-salts and esters), amiprophos-methyl, amitrol, anilofos, asuram, atrazine, azafenidin, Azimuth Azimsulfuron, beflubutamid, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bensulide, bensulide benta
  • safeners include AD-67, benoxacor, cloquintocet-mexyl, cyomerinil, dichlormid, dicyclonone, cyprosulfamide , Diethorate, DKA-24, dymron, fenclorazole-ethyl, fenclorim, hexim (HEXIM), flurazole, flxofenim, furilazole, Isoxadifen (isoxadifen), isoxadifen-ethyl, MCPA, mecoprop, meetcamifen, mefenpyr, mefenpyr-ethyl, mefenpyr-me diethyl), mephenate, MG-1 91, NA (Naphthalic anhydride), OM (Octamethylene-diamine), oxabetrinil, PPG-1292, R-29148 and the like. These components can be used alone or in admixture of two or
  • the compound of the present invention in applying the compound of the present invention as a herbicide, it is usually mixed with a suitable solid carrier or liquid carrier, and if desired, a surfactant, a penetrating agent, a spreading agent, a thickening agent, an antifreezing agent, a binder, a solid carrier.
  • a surfactant e.g., sodium sulfate, sodium sulfate, sodium sulfate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate
  • Examples of solid carriers include quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth, and other minerals, calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride. Examples include salts, synthetic silicic acid and synthetic silicates.
  • Examples of the liquid carrier include alcohols such as ethylene glycol, propylene glycol and isopropanol, aromatic hydrocarbons such as xylene, alkylbenzene and alkylnaphthalene, ethers such as butyl cellosolve, ketones such as cyclohexanone, and esters such as ⁇ -butyrolactone.
  • acid amides such as N-methylpyrrolidone and N-octylpyrrolidone
  • vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil, and water.
  • solid and liquid carriers may be used alone or in combination of two or more.
  • surfactant examples include polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester and polyoxyethylene sorbitan.
  • Nonionic surfactant such as fatty acid ester, alkyl sulfate, alkylbenzene sulfonate, lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate, salt of formalin condensate of naphthalene sulfonate, Salt of formalin condensate of alkylnaphthalenesulfonic acid, polyoxyethylene alkylaryl ether sulfate and phosphate, polyoxyethylene polystyrene Anionic surfactants such as phenyl ether sulfate and phosphate, polycarboxylate and polystyrene sulfonate, cationic surfactants such as alkylamine salt and alkyl quaternary ammonium salt, and amphoteric interfaces such as amino acid type and betaine type An activator is mentioned. The content
  • the compound of the present invention may be mixed and applied with other types of herbicides, various insecticides, fungicides, plant growth regulators, synergists, and the like, as necessary, during formulation or spraying.
  • herbicides various insecticides, fungicides, plant growth regulators, synergists, and the like
  • cost reduction due to a decrease in the amount of applied medicine expansion of the herbicidal spectrum due to the synergistic action of the mixed drugs, and higher herbicidal effects can be expected.
  • a combination with a plurality of known herbicides is also possible.
  • the dosage of the compound of the present invention varies depending on the application scene, application timing, application method, cultivated crops, etc., but generally the amount of the active ingredient is suitably about 0.005 to 50 kg per hectare (ha).
  • Wettable compound of the present invention 0.1 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts Others include, for example, anti-caking agents and decomposition inhibitors.
  • Emulsified compound of the present invention 0.1 to 30 parts Liquid carrier 45 to 95 parts Surfactant 4.9 to 15 parts Others 0 to 10 parts Others include, for example, spreading agents and decomposition inhibitors.
  • Flowable agent compound of the present invention 0.1-70 parts Liquid carrier 15-98.89 parts Surfactant 1-12 parts Others 0.01-30 parts Others include, for example, anti-freezing agents, thickeners, etc. It is done.
  • Dry flowable agent compound of the present invention 0.1 to 90 parts Solid carrier 0 to 98.9 parts
  • Surfactant 1 to 20 parts Others 0 to 10 parts Others include, for example, binders, decomposition inhibitors, etc. .
  • Liquid Compound of the Present Invention 0.01-70 parts
  • Liquid carrier 20-99.99 parts Others 0-10 parts Others include, for example, antifreezing agents, spreading agents and the like.
  • Granules Invention compound 0.01 to 80 parts
  • Solid carrier 10 to 99.99 parts Others 0 to 10 parts
  • Others include, for example, binders, decomposition inhibitors and the like.
  • Powder Compound of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 10 parts Others include, for example, drift inhibitors and decomposition inhibitors. In use, the preparation is sprayed as it is or diluted 1 to 10000 times with water.
  • composition Example 2 Milk Compound No. of the present invention. 1-001 5 parts Xylene 75 parts N-methylpyrrolidone 15 parts Solpol 2680 5 parts (anionic surfactant: Toho Chemical Co., Ltd. trade name) The above is uniformly mixed to obtain an emulsion.
  • composition Example 3 Flowable Agent Compound No. 1-001 25 parts Agrisol S-710 10 parts (Nonionic surfactant: trade name of Kao Corporation) Lnox 1000C 0.5 part (anionic surfactant: Toho Chemical Co., Ltd. trade name) Xanthan gum 0.02 parts Water 64.48 parts After uniformly mixing the above, wet milling to obtain a flowable agent.
  • Dry flowable agent Compound No. 1-001 75 parts Hightenol NE-15 5 parts (Anionic surfactant: Daiichi Kogyo Seiyaku Co., Ltd. trade name) Vanillex N 10 parts (anionic surfactant: Nippon Paper Industries Co., Ltd. trade name) Carplex 2 80 10 parts (Synthetic hydrous silicate: Shionogi Pharmaceutical Co., Ltd. trade name) After uniformly mixing and pulverizing the above, a small amount of water is added and stirred and kneaded, granulated with an extrusion granulator, and dried to obtain a dry flowable agent.
  • the present invention will be described in more detail by specifically describing, as examples, synthesis examples and test examples of oxime compounds represented by formula (1) used as an active ingredient.
  • the present invention is not limited by these.
  • the medium pressure preparative liquid chromatography described in the synthesis example used an intermediate pressure preparative device manufactured by Yamazen Co., Ltd .; YFLC-Wprep (flow rate 18 ml / min, silica gel 40 ⁇ m column).
  • the proton nuclear magnetic resonance chemical shift value of the Example was measured at 300 MHz using Me 4 Si (tetramethylsilane) as a reference material. Moreover, the solvent used for the measurement is described in the following synthesis examples. Moreover, the symbol in the proton nuclear magnetic resonance chemical shift value of an Example represents the following meaning. s: singlet, brs: broad singlet, d: doublet, t: triplet, q: quartet, m: multiplet
  • Step 1 Preparation of ethyl 3-amino-3- (methoxyimino) propanoate
  • Step 2 Preparation of ethyl 3-amino-2- (4-hydroxy-3-mesityl-2-oxocyclopent-3-en-1-yl) -3- (methoxyimino) propanoate International Publication No. 2009/019005
  • ethyl 3-amino-3- (methoxyimino) propanoate 7 g and 5.8 g of potassium carbonate were sequentially added, and the mixture was stirred at room temperature for 15 hours. After completion of the reaction, 50 ml of water was added to the reaction solution.
  • Step 2 Preparation of methyl 3- (4-hydroxy-3-mesityl-2-oxocyclopent-3-en-1-yl) -2- (methoxyimino) butanoate Methyl 3- (4-hydroxy-3-mesityl) To a mixed solution of 40 mg of -2-oxocyclopent-3-en-1-yl) -2-oxobutanoate and 5 ml of methanol, 20 mg of O-methylhydroxylamine hydrochloride was added and stirred at room temperature for 15 hours. . After completion of the reaction, 15 ml of water was added to the reaction solution and extracted with 15 ml of ethyl acetate. The obtained organic layer was washed with water, dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 15 mg of the desired product as a white solid. Melting point 182-183 ° C
  • Synthesis examples of production intermediates for producing the compounds of the present invention are specifically described below as Reaction Examples 1 to 9, but the production intermediates of the present invention are not limited to these.
  • Reaction Example 1 Production of 2- (2-methoxy-4,6-dimethylphenyl) cyclopent-4-ene-1,3-dione
  • Step 1 Production of 2-methoxy-4,6-dimethylbenzaldehyde
  • JP 2010/241919 A To a mixed solution of 13.7 g of 2-hydroxy-4,6-dimethylbenzaldehyde and 150 ml of N, N-dimethylformamide synthesized by the method described in JP 2010/241919 A, 29 g of potassium carbonate and 12.1 ml of dimethyl sulfate were added at 0 ° C. After sequentially adding 7 g, the mixture was stirred at room temperature for 15 hours.
  • Step 2 Production of furan-2-yl (2-methoxy-4,6-dimethylphenyl) methanol
  • a mixed solution of 5.2 g of furan and 75 ml of tetrahydrofuran was cooled to ⁇ 10 ° C. under a nitrogen atmosphere.
  • 53 ml of n-butyllithium (1.6M tetrahydrofuran solution, manufactured by Kanto Chemical Co., Inc.) was added and stirred at the same temperature for 30 minutes.
  • reaction solution After adding a mixed solution of 13.8 g of 2-methoxy-4,6-dimethylbenzaldehyde and 75 ml of tetrahydrofuran to the reaction solution at ⁇ 10 ° C., the reaction solution was warmed to room temperature and stirred for 12 hours. After completion of the reaction, the reaction solution was poured into ice water, and the solvent was distilled off under reduced pressure. To the obtained residue, 100 ml of water was added, followed by extraction with 100 ml of ethyl acetate. The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 20.7 g of the desired product as a brown oil.
  • Step 3 Preparation of 4-hydroxy-5- (2-methoxy-4,6-dimethylphenyl) cyclopent-2-en-1-one Furan-2-yl (2-methoxy-4,6-dimethylphenyl) methanol A mixed solution of 14 g of polyphosphoric acid, 50 ml of acetone and 25 ml of water was added to a mixed solution of 20.7 g, 170 ml of acetone and 55 ml of water, and stirred at 55 ° C. for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure until the volume of the reaction mixture became half. After adding 150 ml of water to the obtained residue, extraction was performed with 100 ml of ethyl acetate.
  • the obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • the obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (2: 1 to 1: 1 gradient) to obtain 11.5 g of the desired product as a black oil. It was.
  • Step 4 Preparation of 2- (2-methoxy-4,6-dimethylphenyl) cyclopent-4-ene-1,3-dione
  • Reaction Example 2 Production of 2- (2-ethoxy-4,6-dimethylphenyl) cyclopent-4-ene-1,3-dione Then, it was synthesized by the same method as in Step 1 to Step 4 of Reaction Example 1. Melting point: 102-104 ° C
  • Reaction Example 3 Preparation of ethyl 3- ⁇ (allyloxy) imino ⁇ -3-aminopropanoate According to the method according to Step 1 of Synthesis Example 1, O-allylhydroxylamine hydrochloride instead of O-methylhydroxylamine hydrochloride Synthesized using salt.
  • 1 H NMR (CDCl 3 ) ⁇ 6.07-5.85 (m, 1H), 5.40-5.05 (m, 2H), 4.48-4.35 (m, 2H), 4.25-4.00 (m, 2H), 3.43-3.10 (m , 2H), 1.33-1.17 (m, 3H) (NH 2 proton was not observed).
  • Reaction Example 4 Preparation of ethyl 3-amino-3- ⁇ (benzyloxy) imino ⁇ propanoate According to the method according to Step 1 of Synthesis Example 1, O-benzylhydroxylamine hydrochloride instead of O-methylhydroxylamine hydrochloride was synthesized.
  • 1 H NMR (CDCl 3 ) ⁇ 7.45-7.25 (m, 5H), 5.50-4.65 (m, 4H), 4.25-4.10 (m, 2H), 3.16 (s, 2H), 1.32-1.18 (m, 3H ).
  • Reaction Example 6 Preparation of ethyl 3-amino-3- ⁇ (2,2,2-trifluoroethoxy) imino ⁇ propanoate According to the method according to Synthesis Example 1, Step 1, instead of O-methylhydroxylamine hydrochloride Synthesized using O-2,2,2-trifluoroethylhydroxylamine.
  • 1 H NMR (CDCl 3 ) ⁇ 5.25-4.70 (m, 2H), 4.37-4.05 (m, 4H), 3.12 (s, 2H), 1.40-1.18 (m, 3H).
  • Reaction Example 7 Preparation of ethyl 3-amino-3- ⁇ (2-methoxyethoxy) imino ⁇ propanoate According to the method according to Step 1 of Synthesis Example 1, O-methoxyethylhydroxyl instead of O-methylhydroxylamine hydrochloride Synthesized using amine hydrochloride.
  • 1 H NMR (CDCl 3 ) ⁇ 5.20-4.80 (m, 2H), 4.25-4.05 (m, 4H), 3.65-3.56 (m, 2H), 3.38 (s, 3H), 3.15 (s, 2H), 1.35-1.20 (m, 3H).
  • Reaction Example 8 Preparation of ethyl 3-amino-3- ⁇ (cyclopropylmethoxy) imino ⁇ propanoate According to the method according to Step 1 of Synthesis Example 1, O-cyclopropylmethylhydroxyl instead of O-methylhydroxylamine hydrochloride Synthesized using amine hydrochloride.
  • 1 H NMR (CDCl 3 ) ⁇ 5.20-4.75 (m, 2H), 4.27-4.05 (m, 2H), 3.83-3.65 (m, 2H), 3.55-3.10 (m, 2H), 1.48-1.00 (m , 4H), 0.60-0.42 (m, 2H), 0.35-0.17 (m, 2H).
  • Reaction Example 9 Preparation of 4-hydroxy-5- (2-methoxy-4,6-dimethylphenyl) cyclopent-2-en-1-one
  • Step 1 Production of 2- ⁇ furan-2-yl (hydroxy) methyl ⁇ -3,5-dimethylphenol
  • furfural 1 6 g and 1.2 g of magnesium chloride (anhydrous) were sequentially added and stirred for 30 minutes.
  • 1.7 g of triethylamine was added, and the mixture was stirred at a temperature at which the solvent was refluxed for 2 hours. After completion of the reaction, the solvent of the reaction solution was distilled off under reduced pressure.
  • the obtained residue was adjusted to pH 1 by adding 1 mol / L hydrochloric acid, and extracted with 30 ml of ethyl acetate.
  • the obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • the obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (5: 1) to obtain 0.55 g of the desired product as a white solid. Melting point: 94-96 ° C
  • Step 2 Preparation of furan-2-yl (2-methoxy-4,6-dimethylphenyl) methanol 0.3 g of 2- ⁇ furan-2-yl (hydroxy) methyl ⁇ -3,5-dimethylphenol and 5 ml of acetone To the mixed solution, 0.45 g of potassium carbonate and 0.21 g of dimethyl sulfate were sequentially added, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, 10 ml of a saturated aqueous ammonium chloride solution was added to the reaction solution, followed by extraction with 15 ml of ethyl acetate.
  • the obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • the obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (10: 1) to obtain 0.37 g of the desired product as a pale yellow viscous substance.
  • Step 3 Preparation of 4-hydroxy-5- (2-methoxy-4,6-dimethylphenyl) cyclopent-2-en-1-one Furan-2-yl (2-methoxy-4,6-dimethylphenyl) methanol To a mixed solution of 5 g, 130 ml of 1,4-dioxane and 80 ml of water, 11 g of zinc chloride and 0.1 ml of 1 mol / L hydrochloric acid were added and stirred at a temperature at which the solvent was refluxed for 1 hour. After completion of the reaction, the solvent of the reaction solution was distilled off under reduced pressure.
  • the compound of the present invention can be synthesized according to the above synthesis example.
  • Examples of the compounds of the present invention produced in the same manner as in Synthesis Examples 1 to 15 are shown in Tables 3 to 9, but the present invention is not limited to these.
  • C-Pr and Pr-c are cyclopropyl groups, n-Bu and Bu-n normal butyl groups, s-Bu and Bu-s are secondary butyl groups, i-Bu and Bu-i are isobutyl groups, T-Bu and Bu-t are tertiary butyl groups, c-Bu and Bu-c are cyclobutyl groups, n-Pen and Pen-n are normal pentyl groups, and c-Pen and Pen-c are Cyclopentyl group, n-Hex and Hex-n are normal hexyl groups, c-Hex and Hex-c are cyclohexyl groups, Hept is a heptyl group, Oct is an octyl group, Ph is a phenyl group Representing, respectively.
  • D2-32a, D2-33a, D2-34a, D2-92c, D2-93c, D2-103a, D2-103b, D2-103c, D2-103d, D2-103e, D2-103f, D2 -103g, D2-103h, D2-103i, D2-103j, D2-108, D3-2c, D3-3, D3-7a, D3-7b, D3-11a, D3-22a, D3-32a, D3-33a , D3-34a and D3-108 represent the following structures.
  • Table 1 shows 1 H-NMR data of compounds having no melting point in Tables 3 to 9.
  • the proton nuclear magnetic resonance chemical shift value was measured at 300 MHz in deuterated chloroform solvent, deuterated dimethyl sulfoxide solvent, deuterated methanol solvent or deuterated water using Me 4 Si (tetramethylsilane) as a reference substance.
  • deuterated dimethyl sulfoxide solvent deuterated methanol solvent or deuterated water
  • (DMSO-d 6 ) “(CD 3 OD)”, “(D 2 O)”
  • Compound No. Indicated for compounds measured in deuterated dimethyl sulfoxide solvent, deuterated methanol solvent or deuterated water, “(DMSO-d 6 )”, “(CD 3 OD)”, “(D 2 O)” and Compound No. Indicated.
  • surface represents the following meaning.
  • each chemical shift value is indicated by “and”.
  • Criterion 5 More than 90% of herbicide rate (almost completely dead) 4 ... Herbicidal Rate 70% or more and less than 90% 3 ... Herbicidal Rate 40% or more and less than 70% 2 ... Herbicidal Rate 20% or more and less than 40% 1 ... Herbicidal Rate 5% or more but less than 20% 0 ... Herbicidal Rate 5% or less (almost effective) None)
  • Test Example 2 Herbicidal effect test by treatment with weed growing season in flooded condition After alluvial soil was put into a 1/10000 are Wagner pot, water was added and mixed to obtain a flooded condition of 4 cm in water depth. Tainubie, Inuhotarui and Konagi seeds were mixed and sown in the cup, and placed in a greenhouse at 25 to 30 ° C. to grow plants. When Tainubier, Inuhotarui and Konagi reached the 1st to 2nd leaf stage, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water so as to have a predetermined dosage and treated on the water surface. Three weeks after the drug treatment, the influence on various plants was investigated according to the criteria of Test Example 1. The results are shown in Table 12.
  • Test Example 3 Herbicidal effect test by foliar treatment After alluvial soil was put into a 1/10000 are Wagner pot, water was added and mixed to obtain a condition of water depth of 0.1 to 0.5 cm. Inobie, Azegaya, Kogomegatsutsu and rice seeds were sown and placed in a greenhouse at 25 to 30 ° C. to grow plants. After growing for 14 days, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dose, and uniformly treated with a small spray on the foliage. Three weeks after the drug treatment, the influence on various plants was investigated according to the criteria of Test Example 1. The results are shown in Table 13.
  • Test Example 4 Herbicidal effect test by soil treatment Put sterilized large soil in a plastic box 21cm long, 13cm wide and 7cm deep, and then weed bark, Enocorosa, Inobie, oats, blackgrass, Italian ryegrass, Atlantic cabbage, The seeds of Ichibi, Aogateto, Shiroza, Jacobe, Yamgra, Giant corn, corn, soybean, rice, wheat, beet and rapeseed were sown in a spot shape and covered with about 1.5 cm of soil.
  • the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dose, and uniformly treated with a small spray on the soil surface. Plants were grown by placing plastic boxes in a greenhouse at 25 to 30 ° C., and after 3 weeks of chemical treatment, the effects on various plants were investigated according to the criteria of Test Example 1. The results are shown in Table 14.
  • the oxime compound of the present invention is a novel compound and is useful as a selective herbicide for rice, corn, soybean, wheat, beet and rapeseed.

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

Abstract

Le problème décrit par la présente invention est d'obtenir un nouveau produit agrochimique, et en particulier un herbicide. La solution de l'invention porte sur un composé d'oxime représenté par la formule (1) et un herbicide le contenant. (Dans la formule (1), B représente B-1 ou similaire ; Q représente NOR7 ; A représente un atome d'hydrogène, alkyle en C1-C6, ou similaire ; R6 représente un atome d'halogène, -N(R6c)R6d, ou similaire ; R6c et R6d représentent un atome d'hydrogène ; R7 représente un atome d'hydrogène, alkyle en C1-C6, ou similaire ; R10, R11, et R12 représentent un atome d'hydrogène ; Z représente un alkyle en C1-C6 ou similaire ; et q représente un entier de 0 à 5.)
PCT/JP2017/022424 2016-06-17 2017-06-16 Composé d'oxime et herbicide WO2017217553A1 (fr)

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JP2016169574A JP2019142777A (ja) 2016-06-17 2016-08-31 オキシム化合物及び除草剤
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018131690A1 (fr) * 2017-01-13 2018-07-19 日産化学工業株式会社 Composé de cétone ou d'oxime et herbicide

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010000773A1 (fr) * 2008-07-03 2010-01-07 Syngenta Limited 5-hétérocyclylalkyl-3-hydroxy-2-phénylcyclopent-2-énones à utiliser comme herbicides
WO2010069834A1 (fr) * 2008-12-15 2010-06-24 Syngenta Participations Ag Nouveaux herbicides
WO2010089210A1 (fr) * 2009-02-04 2010-08-12 Syngenta Limited Nouveaux herbicides
WO2010102848A1 (fr) * 2009-01-22 2010-09-16 Syngenta Limited Herbicides dérivés de la cyclopentadione
WO2011007146A1 (fr) * 2009-07-16 2011-01-20 Syngenta Limited Dérivés 2-(substitution phényle)-cyclopentane-1,3-dione à activité herbicide
WO2016062585A1 (fr) * 2014-10-22 2016-04-28 Syngenta Participations Ag Composés herbicides
WO2016062587A1 (fr) * 2014-10-20 2016-04-28 Syngenta Participations Ag Composés herbicides
WO2016098899A1 (fr) * 2014-12-18 2016-06-23 日産化学工業株式会社 Cétone ou oxime, et herbicide

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010000773A1 (fr) * 2008-07-03 2010-01-07 Syngenta Limited 5-hétérocyclylalkyl-3-hydroxy-2-phénylcyclopent-2-énones à utiliser comme herbicides
WO2010069834A1 (fr) * 2008-12-15 2010-06-24 Syngenta Participations Ag Nouveaux herbicides
WO2010102848A1 (fr) * 2009-01-22 2010-09-16 Syngenta Limited Herbicides dérivés de la cyclopentadione
WO2010089210A1 (fr) * 2009-02-04 2010-08-12 Syngenta Limited Nouveaux herbicides
WO2011007146A1 (fr) * 2009-07-16 2011-01-20 Syngenta Limited Dérivés 2-(substitution phényle)-cyclopentane-1,3-dione à activité herbicide
WO2016062587A1 (fr) * 2014-10-20 2016-04-28 Syngenta Participations Ag Composés herbicides
WO2016062585A1 (fr) * 2014-10-22 2016-04-28 Syngenta Participations Ag Composés herbicides
WO2016098899A1 (fr) * 2014-12-18 2016-06-23 日産化学工業株式会社 Cétone ou oxime, et herbicide

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018131690A1 (fr) * 2017-01-13 2018-07-19 日産化学工業株式会社 Composé de cétone ou d'oxime et herbicide

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