WO2001056979A1 - Derives de cyanoacetamide substitues et herbicides - Google Patents

Derives de cyanoacetamide substitues et herbicides Download PDF

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Publication number
WO2001056979A1
WO2001056979A1 PCT/JP2001/000603 JP0100603W WO0156979A1 WO 2001056979 A1 WO2001056979 A1 WO 2001056979A1 JP 0100603 W JP0100603 W JP 0100603W WO 0156979 A1 WO0156979 A1 WO 0156979A1
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group
alkoxy
alkyl
methyl
groups
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PCT/JP2001/000603
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English (en)
Japanese (ja)
Inventor
Hiroyuki Yamanaka
Satoshi Kajita
Katsunori Tanaka
Masami Koguchi
Shigeo Yamada
Akihiro Takahashi
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Nippon Soda Co., Ltd.
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Priority to AU2001227114A priority Critical patent/AU2001227114A1/en
Publication of WO2001056979A1 publication Critical patent/WO2001056979A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • 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
    • A01N43/08—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 oxygen 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
    • A01N43/02—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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—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
    • 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
    • C07D295/18—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 by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids

Definitions

  • the present invention relates to a substituted cyanoacetamide derivative in which a methylene moiety of a novel cyanoacetamide is substituted with a substituted benzoyl group, and a herbicide.
  • EP 0213892 describes a compound represented by the formula (A) having herbicidal activity and a method for producing the compound.
  • R 1 represents an alkyl group, a cycloalkyl group, and the like, and Q represents a heterocyclic group.
  • R 1 is bonded to a nitrogen atom as in the compound of the present invention. There is no description of the compound that is the group to be formed.
  • EP-A-625505 describes a compound represented by the following formula (C).
  • the compound represented by the formula (C) does not include a compound in which 1 to! ⁇ 5 is a heterocyclic group. Further, there is no description of a compound in which R 6 is an alkyl group or a cycloalkyl group and is a group formed by bonding to a nitrogen atom.
  • An object of the present invention is to provide a herbicide that can be synthesized industrially advantageously, is effective at a low dose, has high safety, and has good crop selectivity.
  • the present invention firstly provides a formula (1)
  • R 2 are each independently a hydrogen atom, a nitro group, Shiano group, a halogen atom, C 1-6 alkyl, C 1-6 alkoxy group, a haloalkyl group, C 1-6 Haroarukoki Represents a C 1-6 alkylthio group, an alkylsulfonyl group or a C 1-6 alkylsulfonyl group.
  • R 3 represents a nitro group, a cyano group, a halogen atom, an alkyl group, an alkoxy group, a C 6 haloalkyl group, a d- 6 haloalkoxy group, an alkylthio group, a C 1-6 alkylsulfenyl group or an alkylsulfonyl group.
  • n represents 0, 1 or 2.
  • R 4, R 5 are each independently a hydrogen atom, an alkyl group, C 2 - 6 alkenyl group, CI- 6 alkoxy group, C 1-6 haloalkyl group, C 1-6 hydroxycarboxylic alkyl group, Ji 6 Haroaru Kokishi group, C 3 - 8 cycloalkyl group, an alkoxy group, Haroaruko alkoxy C - 6 alkyl group, CI- 6 alkoxy C 1-6 alkoxy group, C 1-6 haloalkoxy CM ⁇ alkoxy group, alkylthio C - 6 Alkyl group, C 1-6 alkylthio C 1-6 alkoxy group, amino group, CM alkylamino group, dialkylamino group, alkylcarbonyl group, c1 -s alkoxycarbonyl group, haloalkylcarbonyl group, haloalkoxy carbonyl group, CM alkylsulfonyl group, the haloalky
  • R 4 and R 5 are joined together to form an alkylene chain having 2 to 5 carbon atoms, or R 4 and R 5 together with the bonded nitrogen atom are substituted with a C 1-6 alkyl group or the like. May form a 5- or 6-membered nitrogen-containing heterocyclic ring containing 2 to 4 oxygen or nitrogen atoms.
  • X represents an oxygen atom or a sulfur atom.
  • Z is a formyl group, di-d-6 alkoxymethyl group, C 2 _ 6 alkenyl, C 2-6 Arukini Le group, C 1-6 alkoxides Consequences amino methyl, C 1-6 halo alkoxides Consequences amino methyl group, C 2 _ 6 ⁇ Luque two Ruiminomechiru group, C 26 Haroaruke two Ruiminomechiru group, (halogen atom, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 haloalkyl group, Shiano group, such as nitro group)
  • the optionally substituted heterocyclic group in z of the compound represented by the formula (l) is preferably a kind of group selected from the group shown below.
  • R 6 and R 7 each independently represent a hydrogen atom, a halogen atom, a C 1-6 alkyl group, a haloalkyl group, or a C 1-6 alkoxy group.
  • the present invention provides a herbicide containing one or more of the compound represented by the formula (1) or a salt thereof as an active ingredient.
  • R i and R 2 are each independently a hydrogen atom, a nitro group, a cyano group,
  • Halogen atoms such as fluorine, chlorine, and bromine
  • a C 1-6 alkyl group such as methyl, ethyl, propyl, isopropyl, butyl, isoptyl, s-butyl, t-butyl, etc.
  • Alkoxy groups such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, s-butoxy, t-butoxy,
  • 6- haloalkyl groups such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 1,1-difluoroethyl, 1,1,1-trifluoroethyl and pentafluoroethyl , C such as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1-fluoroethoxy, 1,1-difluoroethoxy, 1,1,1-trifluoroethoxy, pentafluoroethoxy, etc. 1-6 noroanorecoxy group,
  • C w alkylthio groups such as methylthio, ethylthio, propylthio, isopropylthio, butylthio, and butylthio;
  • 6- alkyl sulfonyl groups such as methylsulfonyl, ethylsulfonyl, propylsulfenyl, isopropylsulfenyl, butylsulfenyl and t-butylsulfenyl;
  • Alkyl sulfonyl groups such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, t-butylsulfonyl, etc.
  • R 3 is a nitro group, a cyano group
  • Halogen atoms such as fluorine, chlorine, and bromine
  • alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isoptyl, S-butyl, t-butyl, etc.
  • Alkoxy groups such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, s-butoxy, t-butoxy,
  • haloalkyl groups chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1-fluoroethoxy, 1,1 difluoroethoxy, 1,1,1-trifluoroethoxy, pentafluoro Roethoxy etc.
  • CM alkylthio groups such as methylthio, ethylthio, propylthio, isopropylthio, butylthio, and t-butylthio;
  • a C 1-6 alkyl sulfonyl group such as methylsulfonyl, ethylsulfonyl, propylsulfenyl, isopropylsulfonyl, butylsulfonyl, t-butylsulfonyl, etc.
  • Alkylsulfonyl groups such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, and t-butylsulfonyl;
  • R 4 and R 5 are each independently a hydrogen atom
  • Ci-6 alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isoptyl, s-butyl, t-butyl, etc.
  • CM alkoxy groups such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, s-butoxy, t-butoxy,
  • Haloalkyl groups such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 1,1-difluoroethyl, 1,1,1-trifluoroethyl and pentafluoroethyl; C such as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1_fluoroethoxy, 1,1-difluoroethoxy, 1,1,11-trifluoroethoxy, pentafluoroethoxy, etc. 6 halo anolecoxy group,
  • C 3-8 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,
  • haloalkoxy C 1-6 alkyl group such as trifluoromethyloxymethyl, trifluoromethylethyl, etc.
  • Alkoxy c 1-6 alkoxy groups such as methoxy methoxy, methoxy ethoxy, ethoxy methoxy, etc.
  • C i- 6 haloal such as trifluorometoxime toxic, trifluorometoxetoxy, etc.
  • C 1-6 alkylthio 6 alkyl groups such as methylthiomethyl, methylthioethyl, ethylthiomethyl,
  • C 1-6 alkylthioalkoxy groups such as methylthiomethoxy, methylthioethoxy, and ethylthiomethoxy;
  • Alkylamino groups such as methylamino, ethylamino, propylamino, isopropylamino, and butylamino;
  • Dialkylamino groups such as dimethylamino, getylamino, and ethylmethylamino
  • Alkylcarbonyl groups such as acetyl, propionyl, and petyryl
  • D- 6 alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, t-butoxycarbonyl,
  • Haloalkylcarbonyl groups such as fluoroacetyl, chloroacetyl, trifluoroacetyl, trichloroacetyl,
  • R 4 and R 5 are joined together to form an alkylene chain having 2 to 5 carbon atoms of ethylene, trimethylene, tetramethylene, or pentamethylene, or R 4 and R 5 are a substituent together with a bonding nitrogen atom. May form a nitrogen-containing heterocycle containing 2 to 4 5- or 6-membered nitrogen or oxygen atoms.
  • Such heterocycles include morpholine 41-yl, piperazine 1-1-yl, 1,3,5-perhydrotriazine 1-yl, imidazole 11-yl, pyrazole 11-yl , 1, 2, 4-triazole-l-yl, oxazolidine-l-yl, tetrazol-l-yl and the like. These may be substituted with a C 1-6 alkyl group such as methyl and ethyl.
  • Z is a formyl group
  • Dialkoxymethyl groups such as dimethoxymethyl and diethoxymethyl
  • Echiniru 1 one propynyl, C 2 2-propynyl, and the like - 6 alkynyl group
  • Haloalkoxyminomethyl groups such as fluoromethinominomethyl, chloromethoxyminomethyl, trifinoleolomethoxyminomethyl, and trichloromethoxyminomethyl;
  • More preferred examples of the optionally substituted heterocyclic group for Z include the following groups.
  • R 6 and R 7 are each independently a hydrogen atom, a halogen atom such as fluorine, chlorine, or bromine; an alkyl group such as methyl or ethyl; a d- 6 haloalkyl group such as chloromethyl or trifluoromethyl; Represents a C 1-e alkoxy group such as methoxy and ethoxy.
  • X represents an oxygen atom or a sulfur atom.
  • Table 1 shows typical examples of the compound of the present invention.
  • the abbreviations of AZ1-Z30 used in column Z of this table and Table 2 have the following meanings.
  • the compound (2) and the compound represented by the formula: Ar COQ are reacted in the presence of a base in a solvent in an amount of 1 mol or an excess of each of them, whereby the compound represented by the formula (1) is obtained. Is obtained.
  • Solvents that can be used in this reaction include hydrocarbons such as benzene and toluene, ethers such as tetrahydrofuran (THF) and getyl ether, halogenated hydrocarbons such as methylene chloride and chloroform, and dimethylformamide. (DMF), dimethyl sulfoxide (DMSO), acetonitrile, water, or a mixed solvent thereof.
  • hydrocarbons such as benzene and toluene
  • ethers such as tetrahydrofuran (THF) and getyl ether
  • halogenated hydrocarbons such as methylene chloride and chloroform
  • dimethylformamide dimethylformamide
  • DMF dimethyl sulfoxide
  • acetonitrile water, or a mixed solvent thereof.
  • the base examples include aliphatic amines such as triethylamine and diisopropylethylamine; organic bases such as pyridine; alkali metal hydroxides such as KOH and NaOH; alkali metal carbonates such as sodium carbonate and potassium carbonate; Alkali earth metal hydroxides such as calcium hydroxide and magnesium hydroxide, alkaline earth metal carbonates such as calcium carbonate, alcoholates such as sodium methylate and magnesium ethylate, NaH, lithium Diisopropylamide (LDA) or the like can be used.
  • aliphatic amines such as triethylamine and diisopropylethylamine
  • organic bases such as pyridine
  • alkali metal hydroxides such as KOH and NaOH
  • alkali metal carbonates such as sodium carbonate and potassium carbonate
  • Alkali earth metal hydroxides such as calcium hydroxide and magnesium hydroxide, alkaline earth metal carbonates such as calcium carbonate, alcoholates such as sodium methylate
  • the reaction proceeds smoothly from ⁇ 78 ° C. to the boiling point of the solvent used, preferably from ⁇ 10 ° C. to room temperature.
  • the present compound (1) is the compound (2) wherein: A r C0 2 H (.
  • a r is said to represent the same meaning) dicyclohexyl a compound represented by cyclohexyl Cal positive imide (DC It can also be obtained by reacting in the presence of a dehydrating condensing agent such as C).
  • Examples of the solvent used in this reaction include methylene chloride, chloroform, toluene, ethyl acetate, DMF, THF, 1,2-dimethyloxetane (DME), and acetate nitrile.
  • the reaction mixture is stirred at 110 ° C to 50 ° C until the reaction is completed, and processed by a conventional method.
  • Compound (2) can be obtained, for example, by an amidation reaction between a cyanoacetic acid ester and a corresponding amine, a reaction between a cyanoacetic acid and an amine using a dehydrating condensing agent such as DCC, It can be produced by a general synthetic chemistry technique such as a reaction between chloride and amines.
  • the compound (1) of the present invention contains a free hydroxyl group
  • the compound can be obtained by a known method from an enamine or an analog thereof, an acylate, a sulfonate, a sulfamate, an ether, a thioether, a sulfoxide or a sulfone derivative. And so on.
  • Said suitable enamines or analogs thereof are those in which the OH moieties are each of the formula: — NR e R f (wherein 16 and 1 are each independently hydrogen or a substitution of 1 to 6 carbon atoms. Represents an alkyl group or an aryl group which may be substituted.), Halogen, S (0) g Rh (where Rh is an alkyl group or an aryl group having 1 to 6 carbon atoms which may be substituted) And g represents 0, 1 or 2.).
  • the OH portion is represented by the following formula: —OCOR i, —OR j or OCONRkR l (wherein, R i and R j have the same meanings as the above Rh. And Rk and R 1 have the same meaning as the above-mentioned R e.).
  • the compound represented by the formula (1) can be derived into a salt thereof, particularly, an agriculturally / horticulturally acceptable salt.
  • agriculturally and horticulturally acceptable salts include alkali metal salts such as sodium and potassium, alkaline earth salts such as calcium and ammonium salts, and the like.
  • ammonium salts include those of the formula: N + R a Rb R c R d (where R a, Rb, R c and Rd are each independently substituted by hydrogen or a hydroxy group, etc. And a 10- alkyl group.
  • R a, Rb, R c and Rd are each independently substituted by hydrogen or a hydroxy group, etc.
  • a 10- alkyl group When any of Ra, Rb, Rc, and Rd is a substituted alkyl group, these preferably contain 1 to 4 carbon atoms.
  • the compound (1) of the present invention may have, for example, the following tautomers.
  • R 4 or R 5 is a hydrogen atom, the following tautomers may exist.
  • the compound of the present invention can be obtained by carrying out a usual post-treatment after completion of the reaction.
  • the structure of the compound of the present invention can be determined by measuring various spectra such as IR, NMR and MS.
  • the herbicide of the present invention contains one or more of the compounds of the present invention as an active ingredient.
  • the compound of the present invention can be used in a pure form without adding other components.
  • it can be used in the form of general pesticides that can be used for pesticides, for example, wettable powders, granules, powders, emulsions, aqueous solvents, suspensions, flowables and the like.
  • mineral powder such as soy flour, flour, etc., vegetable powder, diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay, etc.
  • Organic and inorganic compounds such as sodium benzoate, urea, and sodium sulfate can be used. .
  • oil fractions such as kerosene, xylene and solvent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethyls
  • a surfactant may be added, if desired, to obtain a uniform and stable form in these preparations.
  • the surfactant is not particularly limited, and examples thereof include an alkylphenyl ether to which polyoxetylene is added, an alkyl ether to which polyoxetylene is added, a higher fatty acid ester to which polyoxyethylene is added, and a polyoxyethylene.
  • Nonionic surfactants such as sorbitan higher fatty acid esters to which oxyethylene is added, tristyrylphenyl ether to which polyoxyethylene is added, sulfate salts of alkylphenyl ether to which polyoxyethylene is added, alkyl naphthalene sulfonates, Examples include polycarboxylates, ligninsulfonates, formaldehyde condensates of alkylnaphthalenesulfonates, and copolymers of isobutylene-maleic anhydride.
  • the concentration of the active ingredient in the herbicide of the present invention can be changed to various concentrations depending on the form of the preparation described above.
  • concentrations for example, in a wettable powder, 5 to 90% by weight (hereinafter simply referred to as%), preferably 10 to 85%, and in an emulsion, 3 to 70%, preferably 5 to 90%.
  • the concentration can be adjusted to about 60%, in the case of granules, from 0.01 to 50%, preferably from 0.05 to 40%.
  • the wettable powder or emulsion thus obtained is diluted with water to a predetermined concentration to form a suspension or an emulsion, and the granules are directly sprayed or dispersed on soil before or after germination of the weeds. It is mixed.
  • the actual application amount of the herbicide of the present invention is preferably 0.1 g or more of the active ingredient per hectare.
  • the herbicide of the present invention can be used in combination with known fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers, and the like.
  • the synergistic action of the mixed drug can be expected to have even higher effects.
  • a combination with a plurality of known herbicides is also possible.
  • agents suitable for use in combination with the herbicide of the present invention include the following. It is.
  • Anilide herbicides such as diflupanican and propanil; chloroacetamide herbicides such as arlacrol and pretilachlor; aryloxyalkanoic acid herbicides such as 2,4-D, 2,4-DB; diclohop- Aryloxy phenoxy alkanoic acid herbicides such as methyl and phenyl oxapropetyl; arylcarboxylic acid herbicides such as dicampa and pyrithiobac; imidazoline herbicides such as imazaquin and imazethapyr Urea herbicides such as diperon and isoprolon; carbamate herbicides such as chlorprofam and phenmedipham; thiobencalp, EPTC and other chitosan-bameto herbicides; trifluralin, dinitroa such as pendimethalin, etc.
  • Diphenyl herbicides diphenyl ethers such as acifluorene and homesaphene Herbicides; Sulfonyl-peryl herbicides such as benzulfuron monomethyl and nicosulfuron; Triazinone herbicides such as metripzine and metamethanone; Triazine herbicides such as atrazine and cyanazine; Triazopyrimidines such as flumellam Herbicides; Nitrile herbicides such as promoxinil and dikopenyl; Phosphoric acid herbicides such as glyphosate and glyphosinate; Quaternary ammonium salt herbicides such as paracoat and dibenzozot; Cyclic imidic herbicides such as fluthiacet-methyl; benzoylaminopropionic acid herbicides such as benzoylp mouthpethyl and flancropethyl; others, isoxaben, etofumesate, oxadiazone,
  • Additives such as vegetable oils and oil concentrates can also be added to compositions combining these.
  • the compound of the present invention shows a high herbicidal activity in soil treatment and foliage treatment under upland cropping conditions, is effective for various upland weeds such as meadowgrass, Aquinoenoko mouth, Ichibi, and Inubu, and is effective for corn, wheat, soybean, peta, etc. Some compounds are selective for crops.
  • the compound of the present invention Objects can also be applied to the control of weeds in orchards, lawns, track ends, vacant lots, etc.
  • the compounds of the present invention also include compounds that exhibit a plant growth regulating effect such as a growth inhibitory effect on useful plants such as crops, ornamental plants and fruit trees.
  • the compounds of the present invention include compounds that have excellent herbicidal activity against various paddy weeds such as nobie, tamagayari, omodaka, firefly, etc., and have selectivity to rice.
  • the compounds of the present invention also include those having a plant growth regulating activity, a bactericidal activity, an insecticidal and acaricidal activity.
  • Table 2 shows typical examples of the compounds of the present invention obtained as described above, including the above Examples.
  • NMR-4 2.74 (3H, s) 3,28 (3H, s) 3.37 (3H, s) 3.86 (3H, s) 7.85 (1H, d) 8.23 (1H, d)
  • NMR-5 2.36 ( 3H, s) 2.73 (3H, s) 3.32 (6H, s) 7.69 (1 H, d) 8.37 (1 H, d) 8.39 (1 H, s)
  • NMR-6 2.36 (3H, s) 2.83 (3H , s) 3.38 (3H, s) 3.85 (3H, s) 7.72 (1H, d) 8.29 (1H, d)
  • the above ingredients are uniformly mixed and finely pulverized to obtain a wettable powder containing 20% of the active ingredient.
  • the herbicidal effect was investigated according to the following criteria and expressed as a herbicidal index.
  • 1, 3, 5, 7, and 9 are intermediate values between 0 and 2, 2 and 4, 4 and 6, 6 and 8, and 8 and 10, respectively.
  • a 200 cm 2 pot was filled with soil, and seedlings of Meechishiba, Achinonokorogosa, Inubu, Ichibi and Maize were sown on the surface layer, lightly covered with soil, and grown in a greenhouse.
  • the aqueous dilution of the emulsion shown in Example 8 for each test compound is added to 50 liters / 10 liters so that the active ingredient has a predetermined dose.
  • a Sprayed to the foliage of weeds with a small sprayer in an amount equivalent to the spray amount.

Abstract

L'invention concerne d'une part, des dérivés de cyanoacétamide substitués représentés par la formule générale (1) ainsi que leurs sels, lesdits produits possédant une excellente activité herbicide ; et d'autre part, des préparations qui contiennent lesdits dérivés ou leurs sels et qui sont utiles en tant qu'herbicides présentant une excellente sélectivité par rapport aux plantes cultivées : Dans ladite formule (1), R1 et R2 représentent chacun hydrogène, nitro, cyano, halogéno, C1-6alkyle, C1-6alkylsulfonyle ou analogue ; R3 représente nitro, cyano, halogéno, C1-6alkyle ou analogue ; n désigne 0, 1 ou 2 ; R4 et R5 représentent chacun hydrogène, C1-6alkyle, C1-6alcoxy ou analogue, ou alors ils peuvent être réunis pour former une chaîne alkylène, un groupe hétérocyclique ou analogue ; X désigne l'oxygène ou le soufre ; et Z représente formyle, di(C1-6alcoxy)méthyle, phényle, un groupe hétérocyclique ou analogue.
PCT/JP2001/000603 2000-01-31 2001-01-30 Derives de cyanoacetamide substitues et herbicides WO2001056979A1 (fr)

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007507444A (ja) * 2003-09-29 2007-03-29 イサグロ リチェルカ ソシエタ ア レスポンサビリタ リミタータ 除草性活性を有する１，３−ジオンの誘導体
WO2013040117A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
WO2013040021A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
US8765735B2 (en) 2009-05-18 2014-07-01 Infinity Pharmaceuticals, Inc. Isoxazolines as inhibitors of fatty acid amide hydrolase
WO2014151255A1 (fr) 2013-03-15 2014-09-25 Monsanto Technology Llc Méthodes et compositions pour lutter contre les mauvaises herbes
US8927551B2 (en) 2009-05-18 2015-01-06 Infinity Pharmaceuticals, Inc. Isoxazolines as inhibitors of fatty acid amide hydrolase
CN104817511A (zh) * 2015-04-27 2015-08-05 济南大学 一种丁烯二酸酐制备法匹拉韦关键中间体的方法
US9149465B2 (en) 2009-05-18 2015-10-06 Infinity Pharmaceuticals, Inc. Isoxazolines as inhibitors of fatty acid amide hydrolase
CN107652217A (zh) * 2017-10-24 2018-02-02 青岛清原化合物有限公司 取代的苯甲酰基二酮腈类化合物或其互变异构体、盐、制备方法、除草组合物及应用
EP3296402A2 (fr) 2011-09-13 2018-03-21 Monsanto Technology LLC Procédés et compositions pour lutter contre les mauvaises herbes
EP3382027A2 (fr) 2011-09-13 2018-10-03 Monsanto Technology LLC Procédés et compositions de lutte contre les mauvaises herbes
EP3434780A1 (fr) 2011-09-13 2019-01-30 Monsanto Technology LLC Procédés et compositions de lutte contre les mauvaises herbes

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EP0213892A2 (fr) * 1985-08-27 1987-03-11 Rohm And Haas Company Enols à activité herbicide
EP0372470A2 (fr) * 1988-12-08 1990-06-13 Ciba-Geigy Ag Cyano-alpha-oxo-bêta-propionamides
US5034410A (en) * 1989-10-11 1991-07-23 Syntex (U.S.A.) Inc. Anthelmintically active benzenepropanamide derivatives
WO1994024095A1 (fr) * 1993-04-16 1994-10-27 Abbott Laboratories Agents immunosuppresseurs

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Publication number Priority date Publication date Assignee Title
EP0213892A2 (fr) * 1985-08-27 1987-03-11 Rohm And Haas Company Enols à activité herbicide
EP0372470A2 (fr) * 1988-12-08 1990-06-13 Ciba-Geigy Ag Cyano-alpha-oxo-bêta-propionamides
US5034410A (en) * 1989-10-11 1991-07-23 Syntex (U.S.A.) Inc. Anthelmintically active benzenepropanamide derivatives
WO1994024095A1 (fr) * 1993-04-16 1994-10-27 Abbott Laboratories Agents immunosuppresseurs

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007507444A (ja) * 2003-09-29 2007-03-29 イサグロ リチェルカ ソシエタ ア レスポンサビリタ リミタータ 除草性活性を有する１，３−ジオンの誘導体
US8927551B2 (en) 2009-05-18 2015-01-06 Infinity Pharmaceuticals, Inc. Isoxazolines as inhibitors of fatty acid amide hydrolase
US9149465B2 (en) 2009-05-18 2015-10-06 Infinity Pharmaceuticals, Inc. Isoxazolines as inhibitors of fatty acid amide hydrolase
US8765735B2 (en) 2009-05-18 2014-07-01 Infinity Pharmaceuticals, Inc. Isoxazolines as inhibitors of fatty acid amide hydrolase
EP3296402A2 (fr) 2011-09-13 2018-03-21 Monsanto Technology LLC Procédés et compositions pour lutter contre les mauvaises herbes
WO2013040021A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
WO2013040117A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
EP3382027A2 (fr) 2011-09-13 2018-10-03 Monsanto Technology LLC Procédés et compositions de lutte contre les mauvaises herbes
EP3434779A1 (fr) 2011-09-13 2019-01-30 Monsanto Technology LLC Procédés et compositions de lutte contre les mauvaises herbes
EP3434780A1 (fr) 2011-09-13 2019-01-30 Monsanto Technology LLC Procédés et compositions de lutte contre les mauvaises herbes
WO2014151255A1 (fr) 2013-03-15 2014-09-25 Monsanto Technology Llc Méthodes et compositions pour lutter contre les mauvaises herbes
CN104817511A (zh) * 2015-04-27 2015-08-05 济南大学 一种丁烯二酸酐制备法匹拉韦关键中间体的方法
CN107652217A (zh) * 2017-10-24 2018-02-02 青岛清原化合物有限公司 取代的苯甲酰基二酮腈类化合物或其互变异构体、盐、制备方法、除草组合物及应用

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