WO2014084410A1 - Composés cyclohexanones et herbicides les comprenant - Google Patents

Composés cyclohexanones et herbicides les comprenant Download PDF

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Publication number
WO2014084410A1
WO2014084410A1 PCT/JP2013/082651 JP2013082651W WO2014084410A1 WO 2014084410 A1 WO2014084410 A1 WO 2014084410A1 JP 2013082651 W JP2013082651 W JP 2013082651W WO 2014084410 A1 WO2014084410 A1 WO 2014084410A1
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group
alkyl
aryl
halogen atoms
optionally
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PCT/JP2013/082651
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English (en)
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Yosuke NAKASHIMA
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Sumitomo Chemical Company, Limited
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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
    • 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
    • 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
    • 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
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to cyclohexanone compounds and herbicides comprising the same.
  • Patent Document 1 US 4, 209,532
  • Patent Document 2 US 4,303,669
  • Patent Document 3 US 4,351,666
  • Patent Document 4 US 4,409,513
  • Patent Document 5 US 4,659,372
  • Patent Document 6 WO 2001/017972
  • Patent Document 7 WO 2003/059065
  • Patent Document 8 WO 2008/110308
  • Patent Document 9 WO 2010/046194
  • An object of the present invention is to provide a compound having an excellent efficacy for controlling weeds [0006]
  • the present inventors have intensively studied to find that compounds having an excellent efficacy for controlling weeds and as a result, found that a cyclohexanone compound of the . following formula (I) has an excellent efficacy for controlling weeds, which thus have completed the present invention.
  • the present invention includes the followings [1] to [7] .
  • n is an integer of any one of 1 to 5;
  • R represents a hydrogen atom or a methyl group;
  • R 2 and R 3 represent independently of each other a hydrogen atom, an Ci-e alkyl group, a Ci- 6 haloalkyl group, a C 3 -8 cycloalkyl group or a C3-8 halocycloalkyl group, alternatively R 2 and R 3 connect each other to represent an C2-5 alkylene chain, or R 2 and R 3 combine each other to represent an C1-3 alkylidene group optionally having one or more halogen atoms;
  • R 4 represents an C6-10 aryl group or a five- to six- membered heteroaryl group ⁇ with the proviso that the C6-10 aryl group and the five- or six- membered heteroaryl group may have optionally one or more substituents selected from the group consisting of a halogen atom, a pentafluorothio group,- an Ci-6 alkyl group, an C 2 -6 alkenyl group, an C2-6 alkynyl group, an Ci-6 alkoxy group, an Ci- 6 alkylthio group, an C3-6 alkenyloxy group,, an C3-6 alkynyloxy group, an Ci-g alkylsulfinyl group, an Ci-6 alkylsulfonyl group, an (Ci-6 alkyl ) carbonyl group, a hydroxycarbonyl group and a (Ci-6 alkoxy) carbonyl group, and when two or more substituents exist, the substituents may be same or different to each
  • G represents a hydrogen atom or a group of any one of the following formulae:
  • L represents an oxygen atom (0) or a sulfur atom (S);
  • R 5 represents an Ci_6 alkyl group, a C3-8 cycloalkyl group, an C 2 -6 alkenyl group, an C 2 _ 6 alkynyl group, an C6-10 aryl group, an (C6-10 ' aryl)Ci-6 alkyl group, an Ci_6 alkoxy group, a C3-8 cycloalkoxy group, an C3-6 alkenyloxy group, an C3-6 alkynyloxy group, an Ce- ⁇ aryloxy group, an (Ce- ⁇ aryl) Ci-6 alkoxy group, an (Ci- 6 alkyl) (Ci_ 6 alkyl) amino group, an (C3-6 alkenyl) (C 3 _ 6 alkenyl ) amino group, an (Ci-6 alkyl) ( ⁇ - ⁇ aryl) amino group or a five- to six- membered heteroaryl group (with the proviso that these
  • the C3-8 cycloalkyl group, the C6-10 aryl group, an aryl moiety of the (C6-10 aryl)Ci_6 alkyl group, the C3-8 cycloalkoxy group, the C 6 -io aryloxy group, an aryl moiety of the (C6-10 aryl)Ci_6 alkoxy group, an aryl moiety of the (Ci_6 alkyl) (C6-10 aryl) amino group and a five- to six-membered heteroaryl group may each have optionally one or more Ci-6 alkyl groups, and when two or more Ci-6 alkyl groups exist, the alkyl groups may be same or different to each other) ;
  • R 6 represents an Ci-6 alkyl group, an C6-10 aryl group or an (Ci-6 alkyl) (Ci-6 alkyl) amino group (with the proviso that these groups may each have optionally one or more halogen atoms and when two or more halogen atoms exist, the halogen atoms may be same or different to each other; and the C6-10 aryl group may have optionally one or more Ci_ 6 alkyl groups and when two or more Ci_ 6 alkyl groups exist, the alkyl groups may be same or different to each other);
  • R 7 represents a hydrogen atom or an Ci-6 alkyl group
  • W represents an Ci-6 alkoxy group, an Ci-6 alkylthio group, an Ci-6 alkylsulfinyl group or an Ci-6 alkylsulfonyl group (with the proviso that these groups may each have optionally one or more halogen atoms and when two or more halogen atoms exist, the halogen atoms may be same or different to each other) ⁇ ; and
  • Z represents a halogen atom, a cyano group, a nitro group, an Ci- 6 alkyl group, an C 2 -6 alkenyl group, an C 2 -6 alkynyl group, an Ci_ 6 alkoxy group, an (Ci-6 alkyl ) carbonyl group, an Ci-6 alkylthio group, an C 6 -io aryl group, a five- to six- membered heteroaryl group, an C6-10 aryloxy group, a five- or six- membered heteroaryloxy group or a C 3 _8 cycloalkyl group ⁇ with the proviso that the Ci_ 6 alkyl group, the C 2 -6 alkenyl group, the C 2 -6 alkynyl group, the Ci-6 alkoxy group, the (Ci- 6 alkyl ) carbonyl group and the Ci- 6 alkylthio group may each have optionally one - or more halogen atoms, and when two or more hal
  • n is an integer of any one of 1 to 3;
  • R 1 represents a hydrogen atom
  • R 2 and R 3 represent independently of each other a hydrogen atom or an Ci_ 3 alkyl group, alternatively R 2 and R 3 . connect each other to represent an C2-5 alkylene chain;
  • R 4 represents a phenyl group, a 2-pyridyl group, a 3- pyridyl group, a 2-pyrimidinyl group, a 2-pyrazinyl group, a 3-pyridazinyl group, a 3-furyl group, a 2-thienyl group or a 2-thiazolyl group (with proviso that the phenyl group, the 2-pyridyl group, the 3-pyridyl group, the 2-pyrimidinyl group, the 2-pyrazinyl group, the 3-pyridazinyl group, the 3-furyl group, the 2-thienyl group or the 2-thiazolyl group may each have optionally one or more substituents selected from the group consisting of a halogen atom, an C1-3 alkyl group, an (C1-3 alkyl ) carbonyl group, a (C1-3 alkoxy) carbonyl group, an C1-3 alkoxy group, a C1-3 haloalkyl group, an
  • R 5a represents an Ci_6 alkyl group, an C6-10 aryl group, an Ci-6 alkoxy group, an C 3 - 6 alkenyloxy group, an C 3 _ 6 alkynyloxy group or an Ce- ⁇ aryloxy group;
  • R 6a represents an Ci-6 alkyl group; and a represents an C 1 -3 alkoxy group ⁇ ;
  • Z represents a halogen atom, an C 1 -3 alkyl group, an C 2 -4 alkenyl group, an C 2 -4 alkynyl group, an Ci_3 alkoxy group, a C3_ 8 cycloalkyl group, a nitro group, a phenyl group or a five- to six- membered heteroaryloxy group (with the proviso that the .
  • C 1 -3 alkyl group, the C 2 -6 alkenyl group, the C 2 -6 alkynyl group, the C 1 -3 alkoxy group, the phenyl group and the five- to six- membered heteroaryloxy group may each have optionally one or more halogen atoms, and when two or more halogen atoms exist, the halogen atoms may be same or different to each other) .
  • R 2 and R 3 represent independently of each other a
  • R and R connect each other to represent an ethylene chain
  • R 4 represents a phenyl group or a 2-pyridyl group ⁇ with proviso that the phenyl group or the 2-pyridyl group may each have optionally one or more substituents selected from the group consisting of a chlorine atom, a bromine atom, an iodine atom, a fluorine atom, a methyl group, a methoxy group, an acetyl group, a methoxycarbonyl group, a pentafluorothio group, a pentafluoroethyl group, a difluoroethyl group, a heptafluoroisopropyl group, a trifluoromethylthio group, a trifluoromethoxy group and a trifluoromethyl group ⁇ ;
  • G represents a hydrogen atom, an acetyl group, a propionyl group, a butylcarbonyl group, a benzoyl group, a methylsulfonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, an allyloxycarbonyl group, a phenoxycarbonyl group, a methoxymethyl group or an ethoxymethyl group; and
  • Z represents a methyl group, an ethyl group, a phenyl group, a vinyl group, a cyclopropyl group, a nitro group, a fluorine atom, a chlorine atom, a bromine atom, a methoxy group, a trifluoromethyl group, a 5-trifluoromethyl-2- chloropyridyloxy group or an ethynyl group.
  • a herbicide comprising a cyclohexanone compound of any one of [1] to [4] as an active ingredient and an inert carrier.
  • a method for controlling weeds which comprises applying an effective amount of a cyclohexanone compound of formula (I) to weeds or soil where weeds grow, wherein the cyclohexanone compound of formula (I) is a compound represented by a formula:
  • n is an integer of any one of 1 to 5;
  • R 1 represents a hydrogen atom or a methyl group
  • R 2 and R 3 represent independently of each other a hydrogen atom, an Ci-6 alkyl group, a Ci-6 . haloalkyl group, a C3-8 cycloalkyl group or a C3-8 halocycloalkyl group, alternatively R 2 and R 3 connect each other to represent an C2-5 alkylene chain, or R 2 and R 3 combine each other to represent an C1-3 alkylidene group optionally having one or more halogen atoms;
  • ⁇ represents a binding site
  • R 4 represents an Ce- ⁇ aryl group or a five- to six- membered heteroaryl group ⁇ with the proviso that the C 6 - 10 aryl group and the five- or six- membered heteroaryl group may have optionally one or more substituents selected from the group consisting of a halogen atom, a pentafluorothio group, an Ci-6 alkyl group, an C 2 -e alkenyl group, an C 2 -6 alkynyl group, an Ci-s alkoxy group, an Ci_6 alkylthio group, an C3-6 alkenyloxy group, an C3-6 alkynyloxy group, an Ci_ 6 alkylsulfinyl group, an Ci-6 alkylsulfonyl group, an (Ci-6 alkyl ) carbonyl group, a hydroxycarbonyl group and a (Ci_ 6 alkoxy) carbonyl group, and when two or more substituents exist, the substituents may be same
  • G represents a hydrogen atom or a group of any one of the following formulae: ⁇ wherein
  • L represents an oxygen atom (0) or a sulfur atom (S);
  • R 5 represents an Ci_ 6 alkyl group, a C 3 - 8 cycloalkyl group, an C2-6 alkenyl group, an C2-6 alkynyl group, an C 6 _i 0 aryl group, an (C 6 -io aryl)Ci- 6 alkyl group, an Ci_ 6 alkoxy group, a C3-8 cycloalkoxy group, an C3-6 alkenyloxy group, an C 3 _6 alkynyloxy group, an C 6 -io aryloxy group, an (C 6 -io aryl)Ci-6 alkoxy group, an (Ci_ 6 alkyl) (Ci- 6 alkyl) amino group, an (C3-6 alkenyl) (C 3 _ 6 alkenyl ) amino group, an (Ci_ 6 alkyl) (C 6 -io aryl) amino group or a five-
  • aryl)Ci- 6 alkyl group the C 3 - 8 cycloalkoxy group, the C 6 -io aryloxy group, an aryl moiety of the (C 6 -io aryl)Ci_ 6 alkoxy group, an aryl moiety of the (Ci- 6 alkyl.) (C 6 -i 0 aryl) amino group and a five- to six-membered heteroaryl group may each have optionally one or more Ci_ 6 alkyl groups, and when two or more Ci-e alkyl groups exist, the alkyl groups may be same or different to each other) ;
  • R 6 represents an Ci_6 alkyl group, an C6-10 aryl group or an (Ci- 6 alkyl) (Ci_ 6 alkyl) amino group (with the proviso that these groups may each have optionally one or more halogen atoms and when two or more halogen atoms exist, the halogen atoms . may be same or different to each other; and the C6-10 aryl group may have optionally one or more Ci_6 alkyl groups and when two or more Ci-6 alkyl groups exist, the alkyl groups may be same or different to each other) ;
  • R 7 represents a hydrogen atom or an Cis alkyl group
  • W represents an Ci_ 6 alkoxy group, an Ci- 6 alkylthio group, an Ci-6 alkylsulfinyl group or an Ci_6 alkylsulfonyl group (with the proviso that these groups may each have optionally one or more halogen atoms and when two or more halogen atoms exist, the halogen atoms may be same or different to each other) ⁇ ; and
  • Z represents a halogen atom, a cyano group, a nitro group, an i-s alkyl group, an C 2 -6. alkenyl group, an C 2 -6 alkynyl group, an Ci-6 alkoxy group, an (Ci-6 alkyl ) carbonyl group, an Ci-6 alkylthio group, an Ce- ⁇ aryl group, a five- to six- membered heteroaryl group, an Ce- ⁇ aryloxy group, a five- or six- membered heteroaryloxy group or a C3-8 cycloalkyl group ⁇ with the proviso that the Ci-6 alkyl group, the C 2 -6 alkenyl group, the C 2 -6 alkynyl group, the Ci-6 alkoxy group, the (Ci- 6 alkyl ) carbonyl group and the Ci-6 alkylthio group may each have optionally one or more halogen atoms, and when two or more halogen atoms exist, the
  • n is an integer of any one of 1 to 5;
  • R 1 represents a hydrogen atom or a methyl group
  • R 2 and R 3 represent independently of each other a hydrogen atom, an Ci_ 6 alkyl group, a Ci_6 haloalkyl group, a C3-8 cycloalkyl group or a C3-8 halocycloalkyl group, alternatively R 2 and R 3 connect each other to represent an C2-5 alkylene chain, or R 2 and R 3 combine each other to represent an Ci_ 3 alkylidene. group optionally having one or more halogen atoms;
  • R 4 represents an Ce- ⁇ aryl group or a five- to six- membered heteroaryl group ⁇ with the proviso that the Ce- ⁇ aryl group and the five- or six- membered heteroaryl group may have optionally one or more substituents selected from the group consisting of a halogen atom, a pentafluorothio group, an Ci-e alkyl group, an C2-6 alkenyl group, an C2-6 alkynyl group, an Ci-6 alkoxy group, an Ci_ 6 alkylthio group, an C3-6 alkenyloxy group, an C3-6 alkynyloxy group, an C3.-6 alkylsulfinyl group, an Ci-6 alkylsulfonyl group, an (Ci-6 alkyl ) carbonyl group, a hydroxycarbonyl group and a (Ci-6 alkoxy) carbonyl group, and when two or more substituents exist, the substituents may be same or different to each other;
  • G represents a hydrogen atom or a group of any one of the following formulae:
  • L represents an oxygen atom (0) or a sulfur atom (S);
  • R 5 represents an Ci_ 6 alkyl group, a C 3 _ 8 cycloalkyl group, an C 2 -6 alkenyl group, an C 2 -6 alkynyl group, an C 6 -io aryl group, an (C 6 -io aryl)Ci- 6 alkyl group, an Ci- 6 alkoxy group, a C3-8 cycloalkoxy group, an C3-6 alkenyloxy group, an C 3 -6 alkynyloxy group, an e-10 aryloxy group, an ( ⁇ - ⁇ aryl)Ci_6 alkoxy group, an (Ci_ 6 alkyl) (Ci_ 6 alkyl)amino group, an (C3-.6 alkenyl) (C 3 - 6 alkenyl ) amino group, an (Ci_ 6 alkyl) (C6-10 aryl) amino group or a " five- to six
  • R 6 represents an Ci_ 6 alkyl group, an C6-10 aryl group or an (Ci_ 6 alkyl) (Ci_ 6 alkyl) amino group (with the proviso that these groups may each have optionally one or more halogen atoms and when two or more halogen atoms exist, the halogen atoms may be same or different to each other; and the C6-10 aryl group may have optionally one or more Ci-6 alkyl groups and when two or more Ci-6 alkyl groups exist, the alkyl groups may be same or different to each other) ;
  • R 7 represents a hydrogen atom or an Ci-6 alkyl group; represents an Ci-6 alkoxy group, an Ci-6 alkylthio group, an Ci-6 alkylsulfinyl group or an Ci-6 alkylsulfonyl group (with the proviso that these groups may each have optionally one or more halogen atoms and when two or more halogen atoms exist, the halogen atoms may be same or different to each other) ⁇ ; and
  • Z represents a halogen atom, a cyano group, a nitro group, an Ci_6 alkyl group, an C 2 -6 alkenyl group, an C 2 -6 alkynyl group, an Ci-6 alkoxy group, an (Ci_ 6 alkyl ) carbonyl group, an Ci_ 6 alkylthio group, an C 6 -io aryl group, a five- to six- membered heteroaryl group, an C6-10 aryloxy group, a five- or six- membered heteroaryloxy group or a C3-8 cycloalkyl group ⁇ with the proviso that the Ci-6 alkyl group, the C 2 -6 alkenyl group, the C 2 -6 alkynyl group, the Ci-6 alkoxy group, the (Ci_ 6 alkyl ) carbonyl group and the Ci- 6 alkylthio group may each have optionally one or more halogen atoms, and when two or more halogen atoms
  • n is an integer of 2 or more, Z may be same or different to each other ⁇ ] .
  • the compound of the present invention shows an efficacy for controlling weeds and is therefore useful as an active ingredient for herbicides.
  • the substituent of the present invention is explained.
  • the ''Ci-6 alkyl group' 1 to be used herein means an alkyl group having one to six carbon atoms, and includes, for example, a methyl group, an ethyl group, a normalpropyl group, an isopropyl group, a normalbutyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a normalpentyl group, a sec-pentyl group, an isopentyl group, a neopentyl group, a normalhexyl group and an isohexyl group.
  • the ' 'Ci-6 haloalkyl group' 1 to be used herein means an Ci-6 alkyl group wherein one or more hydrogen atoms of the alkyl group are substituted with one or more halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and includes, for example, a trifluoromethyl group, a chloromethyl group, a 2,2,2- trichloroethyl group, a 2 , 2 , 2-trifluoroethyl group and a 2,2, 2-trifluoro-1, 1-dichloroethyl group.
  • halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom
  • the ' ' C3-8 ' cycloalkyl group'' to be used herein means a cycloalkyl group having three to eight carbon atoms and includes, for example, a cyclopropyl group, a cyclopentyl group and a cyclohexyl group.
  • the ' 1 C3-8 halocycloalkyl group' ' to be used herein means a C3-8 cycloalkyl group wherein one or more hydrogen atoms of the C3-8 cycloalkyl group is/are substituted with one or. more halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom and includes, for example, a 2-chlorocyclopropyl group and a , -difluorocyclohexyl group.
  • the ' ' C 2 -5 alkylene chain 1 ' to be used herein means an alkylene chain having two to five carbon atoms and includes, for example, an ethylene chain, a propylene chain (i.e., a trimethylene chain), a butylene chain (i.e., a tetramethylene chain) and a pentylene chain (i.e., a pentamethylene chain) .
  • R 2 and R 3 When R 2 and R 3 connect each other to represent an C 2 -5 alkylene chain, R 2 and R 3 combine together with the carbon to which R 2 and R 3 are attached to form a C 3 - 6 cycloalkyl group.
  • R 2 and R 3 when R 2 and R 3 connect each other to represent an ethylene chain, R 2 and R 3 combine together with the carbon to which R 2 and R 3 are attached to form a C3 cycloalkyl group, i.e., a cyclopropyl group.
  • the ' ' Ci-3 alkylidene chain 1 ' to be used herein means an alkylidene chain having one to three carbon atoms and includes, for example, a methylidene group, an ethylidene group and an isopropylidene group.
  • the ''C 6 -io aryl group 1 ' to be used herein means an aryl group having six to ten carbon atoms and includes, for example, a phenyl group and a naphthyl group.
  • the 11 five- to six- membered heteroaryl group' 1 to be used herein means an aromatic five- or six- membered heterocyclic group having 1 to 3 heteroatoms selected from a nitrogen atom, an oxygen atom or a sulfur atom and includes, for example, a 2-pyridyl group, a 4-pyridyl group, a 3-furyl group, a pyrimidinyl group, a 3-thienyl group and a 1-pyrazolyl group.
  • the ' 'halogen atom' ' to be used herein includes, for example, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • the ''C 2 -6 alkenyl group'' to be used herein means an alkenyl group having two to six carbon atoms and includes, for example, a vinyl group, an allyl group, a l-butene-3-yl group, a 3-butene-l-yl group, a 1-pentenyl group and 1- hexenyl group.
  • the ' ' C2- alkenyl group' ' to be used herein means an alkenyl group having two to four carbon atoms and includes, for example, a vinyl group, an allyl group, a l-butene-3-yl group and a 3-butene-l-yl group.
  • the ' ' C 2 -6 alkynyl group'' to be used herein means an alkynyl group having two to six carbon atoms and includes, for example, an ethynyl group, a propargyl group, a 2- butynyl group, a.2-pentynyl group and 2-hexynyl group.
  • the 1 ' C2-4 alkynyl group' ' to be used herein means an alkynyl group having two to four carbon atoms and includes, for example, an ethynyl group, a propargyl group and a 2- butynyl group.
  • the ' ' Ci-6 alkoxy group'' to be used herein means an alkoxy group having one to six carbon atoms and includes, for example, a methoxy . group, an ethoxy group, a normalpropyloxy group, an isopropyloxy group, a normalbutoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a normalpentyloxy group, a sec- pentyloxy group, an isopentyloxy group, a neopentyloxy group, a normalhexyloxy group and an isohexyloxy group.
  • the 1 ' Ci-6 alkylthio group 1 ' to be used herein means an alkylthio group having one to six carbon atoms and includes, for example, a methylthio group, an ethylthio group and an isopropylthio group.
  • the ' ' Ci-3 alkylthio group'' to be used herein means an alkylthio group having one to three carbon atoms and includes, for example, a methylthio group, an ethylthio group and an isopropylthio group.
  • the ' 'C3-6 alkenyloxy group'' to be used herein means 201
  • the ' 'C3-6 alkynyloxy group' 1 to. be used herein means an alkynyloxy group having three to six carbon atoms and includes, for example, a propargyloxy group and a 2- butynyloxy group.
  • Ci_6 alkoxy group 1 ' to be used herein means an Ci_ 6 alkoxy group wherein one hydrogen atom of the alkoxy group is substituted with an C6-10 aryl group and includes, for example, a benzyloxy group and a phenethyloxy .
  • Ci-6 alkyl group'' to be used herein means an Ci_6 alkyl group wherein one hydrogen atom of the alkyl group is substituted with an ⁇ - ⁇ aryl group and includes, for example, a benzyl group and a phenethyl group.
  • the ' 1 C3-8 cycloalkoxy group'' means a cycloalkoxy group having three to eight carbon atoms and includes, for example, a cyclopropyloxy group, a cyclopentyloxy group and a cyclohexyloxy group.
  • the " ' ( C 1-6 alkyl) ( Ci- 6 . alkyl) amino group' ' to be used herein means an amino group wherein two hydrogen atoms of the amino group are substituted with two Ci-6 alkyl groups that may be same or different to each other and includes, for example, a dimethylamino group, a diethylamino group and an ethylmethylamino group.
  • amino group herein means an amino group wherein two hydrogen atoms of the amino group are substituted with two C3-6 alkenyl groups that may be same or different to each other and includes, for example, a diallylamino group and a di(3- butenyl) amino group.
  • the 11 (Ci-6 alkyl) (C 6 -io aryl) amino group 1 ' to be used herein means an amino group wherein two hydrogen atoms of the amino group are substituted with an Ci- 6 alkyl group and a C 6 -io aryl group and includes for example, a methylphenylamino group and an ethylphenylamino group.
  • the ''Ci- 6 alkylsulfinyl group' 1 to be used herein means an alkylsulfinyl group having one to six carbon atoms and includes, for example, a methylsulfinyl group, an ethylsulfinyl group and an isopropylsulfinyl group.
  • the ' 1 Ci- 6 alkylsulfonyl group'' to be used herein means an alkylsulfonyl group having one to six carbon atoms and includes, for example, a methylsulfonyl group, an ethylsulfonyl group and an isopropylsulfonyl group.
  • the ⁇ ' ⁇ - ⁇ aryloxy group 1 ' to be used herein means an aryloxy group having six to ten carbon atoms and includes, for example, a phenoxy group and a naphthyloxy group.
  • the ''five- to six- membered heteroaryloxy group'' to be used herein means an aromatic five- or six- membered heterocyclyloxy group having one to three heteroatoms selected from a nitrogen atom, an oxygen atom or a sulfur atom and includes, for example, a 2-pyridyloxy group and a 3-pyridyloxy group.
  • the '' (Ci-6 -alkoxy) carbonyl group'' to be used herein means a carbonyl group having an Ci_6 alkoxy group and includes, for example, a methoxycarbonyl group and an ethoxycarbonyl group.
  • the 1 1 (Ci-3 alkoxy) carbonyl group 1 ' to be used herein means, a carbonyl group having an C1-3 alkoxy group and includes, for example, a methoxycarbonyl group, an ethoxycarbonyl group and a propyloxycarbonyl group
  • the ' ' (Ci-6 alkyl ) carbonyl group' ' to be used herein means a carbonyl group having an Ci_ 6 alkyl group and includes, for example, a methylcarbonyl group, an ethylcarbonyl group and an isopropylcarbonyl group.
  • the '' (Ci-3 alkyl ) carbonyl group'' to be used herein means a carbonyl group having an alkyl group having one to three carbon atoms and includes, for example, a methylcarbonyl group, an ethylcarbonyl group and a propylcarbonyl group.
  • the ' ' Ci-3 alkyl group 1 ' to be used herein means an alkyl group having one to three carbon atoms and includes, for example, a methyl group, an ethyl group, a normalpropyl group and an isopropyl group.
  • the ' ' Ci-3 alkoxy group' ' to be used herein means an alkoxy group having one to three carbon atoms and includes, for example, a methoxy group, an ethoxy group, a normalpropyloxy group and an isopropyloxy group.
  • the ' 'Ci-3 haloalkyl group 1 ' to be used herein means an Ci-3 alkyl group wherein one or more hydrogen atoms of the alkyl group are substituted with one or more halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom and includes, for example, a trifluoromethyl group, a chloromethyl group, a 2 , 2 , 2-trichloroethyl group, a 2, 2, 2-trifluoroethyl group and a 2 , 2 , 2-trifluoro-1 , 1- dichloroethyl group.
  • halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom and includes, for example, a trifluoromethyl group, a chloromethyl group, a 2 , 2 , 2-trichloroethyl group, a
  • the ' 'Ci-3 haloalkoxy group' 1 to be used herein means an Ci-3 alkoxy group wherein one or more hydrogen atoms of the alkoxy group are substituted with one or more halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom and includes, for example, a trifluoromethoxy group, a 2 , 2 , 2-trichloroethoxy group, a 3, 3-difluoropropyloxy group and a 2 , 2 , 2-trifluoroethoxy group.
  • halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom and includes, for example, a trifluoromethoxy group, a 2 , 2 , 2-trichloroethoxy group, a 3, 3-difluoropropyloxy group and a 2 , 2 , 2-tri
  • the ' 'Ci-3 haloalkylthio group'' to be used herein means an Ci_ 3 alkylthio group wherein one or more hydrogen atoms of the alkylthio group are substituted with one or more halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom and includes, for example, a trifluoromethylthio group, a chloromethylthio group, a 2 , 2 , 2-trichloroethylthio group, a 2 , 2 , 2-trifluoroethylthio group and a 2 , 2 , 2-trifluoro-1 , 1-dichloroethylthio group.
  • halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom and includes, for example, a trifluoromethylthio group, a chloromethyl
  • the cyclohexanone compounds of the formula (I) may form agronomically acceptable salts with inorganic bases or organic bases and the present invention may encompass the salt forms of the cyclohexanone compound.
  • the salt includes, for example, salts that are formed by mixing the compound with inorganic bases (for example, hydroxides, carbonates, hydrogen carbonates, acetates or hydrides of alkali metals (for example,, lithium, sodium and potassium) ) , hydroxides or hydrides of alkaline- earth metals (for example, magnesium, calcium and barium) and ammonia), organic bases (for example, dimethylamine, triethylamine, piperazine, pyrrolidine, piperidine, 2- phenylethylamine, benzylamine, ethanolamine, diethanolamine, pyridine and collidine) or metal alkoxides (for example, sodium methoxide, potassium tert-butoxide and magnesium methoxide) .
  • inorganic bases for example
  • stereoisomers for example, enantiomer and diastereomer
  • the present compound may encompass all these stereoisomers and a mixture of two or more arbitrary stereoisomers.
  • geometric isomers for example, each E/Z or trans/cis isomer, each S-trans/S-cis isomer and the others
  • the present compound may encompass all these geometric isomers and a mixture of two or more arbitrary geometric isomers .
  • n 3;
  • R 4 represents a phenyl group
  • Z represents an Ci-6 alkyl group optionally having one or more halogen atoms, a halogen atom, a vinyl group or an ethynyl group;
  • n 3 ,
  • R 2 represents a hydrogen atom or a methyl group
  • R 3 represents a hydrogen atom or a methyl group
  • R 4 represents a phenyl group
  • Z represents an Ci_ 6 alkyl group optionally having one or more halogen atoms, a halogen atom, a vinyl group or an ethynyl group;
  • n 3 ,
  • R 2 and R 3 represent independently of each other a hydrogen atom or an Ci- 6 alkyl group
  • R 4 represents a phenyl group or a 2-pyridyl group
  • Z represents a halogen atom, an Ci- 6 alkyl group, an Ci- 6 alkenyl group, an Ci- 6 alkynyl group or an Ci- 6 alkoxy group.
  • the herbicide of the present invention comprises the present compound and inert carriers (hereinafter, sometimes referred to as '.'the present herbicide 1 ').
  • the present herbicide can be usually prepared by further adding auxiliary agents for formulation such as surfactants, stickers, dispersers and stabilizers to formulate into wettable powders, water dispersible granules, flowables, granules, dry flowables, emulsifiable concentrates, aqueous solutions, oil solutions, smoking agents, aerosols, microcapsules and the others.
  • the present herbicide usually contains the present compound in 0.1 to 80% by weight.
  • the inert carrier includes a solid carrier, a liquid carrier and a gaseous carrier.
  • solid carrier examples include clays (for example, kaolin, diatomaceous earth, synthetic hydrated silicon dioxide, Fubasami clay, bentonite and acid clay) , talcs or the other inorganic minerals (for example,
  • the liquid carrier examples include water, alcohols (for example, methanol and ethanol), ketones (for example, acetone and methyl ethyl ketone), aromatic hydrocarbons (for example, benzene, toluene, xylene, ethylbenzene and methyl naphthalene) , aliphatic hydrocarbons (for example, n-hexane, cyclohexane and
  • kerosene kerosene
  • esters for example, ethyl acetate and butyl acetate
  • nitriles for example, acetonitrile
  • diisopropylether diisopropylether
  • acid amides for example, N, N-dimethyl formamide and dimethylacetamide
  • halogenated hydrocarbons for example, dichloroethane, trichloroethylene and carbon tetrachloride
  • surfactants examples include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylenated compounds thereof, polyethylene glycol ethers, polyol esters and sugar alcohol derivatives [0018]
  • auxiliary agents for formulation examples include stickers and dispersers, specifically casein, gelatin, polysaccharides (for example, starch, gum arabic, cellulose derivatives and alginic acid) , lignin derivatives, bentonite, sugars, water-soluble synthetic polymers (for example, polyvinyl alcohol, polyvinyl pyrrolidone and polyacrylic acids)., PAP (acidic isopropyl phosphate), BHT (2, 6-di-tert-butyl-4-methylphenol ) , BHA (a mixture of 2- tert-butyl-4 -methoxyphenol and 3-tert-butyl-4- methoxyphenol ) , vegetable oils, mineral oils, fatty acids or fatty acid esters thereof and the others.
  • stickers and dispersers specifically casein, gelatin, polysaccharides (for example, starch, gum arabic, cellulose derivatives and alginic acid) , lignin derivatives, bentonite, sugars, water-soluble synthetic
  • the method for controlling weeds of the present invention comprises applying an effective amount of the present compound to weeds or to a soil where weeds grow (hereinafter, sometimes referred as to ''the present weeds controlling method 1 ').
  • the present herbicide is usually used.
  • the method of application comprises, for example, a foliage treatment of the weeds using the present herbicide, a treatment of the soil surface where the weeds grow, and . a soil incorporation treatment of the soil where the weeds grow.
  • the present compound is applied in amount of usually 1 to 5,000g and preferably 10 to l, 000g per 10, 000 m 2 of area to be controlled weeds .
  • the present compound can be applied to an agricultural land and the others where ' 'plant' ' as below-mentioned is cultivated.
  • solanaceous vegetables for example, eggplant, tomato, pimento, pepper and potato
  • cucurbitaceous vegetables for example, cucumber, pumpkin, zucchini, water melon and melon
  • cruciferous vegetables for example, Japanese radish, white turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, leaf mustard, broccoli and cauliflower.
  • asteraceous vegetables for example, burdock, crown daisy, artichoke and lettuce
  • liliaceous vegetables for example, green onion, onion, garlic and asparagus
  • ammiaceous vegetables for example, carrot, parsley, celery and parsnip
  • chenopodiaceous vegetables for example, spinach and Swiss chard
  • lamiaceous vegetables for example, Perilla frutescens,. mint and basil
  • pomaceous fruits for example, apple, pear, Japanese pear, Chinese quince and quince
  • stone fleshy fruits for example, peach, plum, nectarine, Prunus mume, cherry fruit, apricot and prune
  • citrus fruits for example, Citrus unshiu, orange, lemon, lime and grapefruit
  • nuts for example, chestnut, walnuts, hazelnuts, almond, pistachio, cashew nuts and macadamia nuts
  • berry fruits for example, blueberry, cranberry, blackberry and raspberry
  • grape kaki persimmon, olive, Japanese plum, banana, coffee, date palm, coconuts, oil palm and the others;
  • Trees other than fruit trees are other than fruit trees.
  • flowering plant for example, dwarf azalea, camellia hydrangea sasanqua, Illicium anisatunu cherry trees x tulip tree, crape myrtle and fragrant olive
  • roadside trees for example, ash, birch, dogwood, Eucalyptus, Ginkgo biloba, lilac, maple, Quercus, poplar, Judas tree, Liquidambar formosana, plane tree, zelkova, Japanese arborvitae, fir wood, hemlock, juniper, Pinus, Picea, Taxus cuspidate, elm and Japanese horse chestnut), Sweet viburnum, Podocarpus macrophyllus , Japanese cedar, Japanese cypress, croton, Japanese spindletree and Photinia glabra) ;
  • flowers for example, rose, carnation, chrysanthemum, Eustoma, gypsophila, gerbera, marigold, salvia, petunia, verbena, tulip, aster, gentian, lily, pansy, cyclamen, orchid, lily of the valley, lavender, stock, ornamental cabbage, primula, poinsettia, gladiolus, cattleya, daisy, cymbidium and begonia) ,
  • bio-fuel plants for example, jatropha, safflower, Camelina, switch grass, Miscanthus giganteus, Phalaris arundinacea, Arundo donax, Kenaf ⁇ Hibiscus cannabinus) , cassava ⁇ Manihot esculenta) , willow (Salicaceae) , etc.
  • the "crops” include genetically modified crops.
  • the present compound can be mixed or combined with other herbicides, phytotoxicity reducing agents, plant growth regulators, pesticides, miticides, nematicides, fungicides and/or synergists.
  • Examples of the active ingredient as the herbicides include the followings:
  • fluometuron isouron, tebuthiuron, methabenzthiazuron, cumyluron, daimuron, methyl-daimuron and the others;
  • amiprofos-methyl butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, glufosinate-P, bialaphos and the others;
  • oxadiazon cinidon-ethyl , carfentrazone-ethyl , surfentrazone, flumiclorac-pentyl , flumioxazin, pyraflufen- ethyl, oxadiargyl, pentoxazone, fluthiacet-methyl , butafenacil, benzfendizone, bencarbazone, saflufenacil and the others;
  • imazamethabenz-methyl imazamox, imazapic, imazapyr, imazaquin, imazethapyr and the others;
  • oxaziclomefone benfuresate, ACN, pyridate, chloridazon, norflurazon, flurtamone, diflufenican, .
  • picolinafen beflubutamid, clomazone, amicarbazone, pinoxaden, pyraclonil, pyroxasulfone, thiencarbazone-methyl , aminocyclopyrachlor, ipfencarbazone, methiozolin, fenoxasulfone and the others.
  • Examples of the active ingredient as the phytotoxicity reducing agents include the followings :
  • Examples of the active ingredient as the plant growth regulators include the followings:
  • hymexazol paclobutrazol , uniconazole-P, inabenfide, prohexadione-calcium, aviglycine, 1-naphthalene acetamide, abscisic acid, indolebutyric acid, ethychlozate, ethephon, cloxyfonac, chlormequat, dichlorprop, gibberellins , prohydroj asmon, benzyladenine, forchlorfenuron, maleic hydrazide, calcium peroxide, mepiquat-chloride, 4-CPA (4- chlorophenoxyacetic acid) and the others.
  • Examples of the active ingredient as the pesticides include the followings:
  • MEP fosthiazate, formothion, isofenphos
  • acrinathrin allethrin, beta-cyfluthrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, empenthrin, deltamethrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenoprox, flumethrin, fluvalinate, halfenprox, imiprothrin,
  • cartap bensultap, thiocyclam, monosultap, bisultap;
  • chlorfluazuron bistrifluron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron and the others;
  • aldrin dieldrin, chlordane, DDT, dienochlor,
  • bromopropylate bromopropylate, buprofezin, chlorphenapyr, cyromazine, DCIP (dichlorodiisopropyl ether), D-D ( 1 , 3-Dichloropropene ) , emamectin-benzoate, fenazaquin, flupyrazofos , hydroprene, methoprene, indoxacarb, metoxadiazone, milbemycin-A,
  • pymetrozine pyridalyl, pyriproxyfen, spinosad, sulfluramid, tolfenpyrad, triazamate, flubendiamide, lepimectin,
  • aluminium phosphide arsenous oxide, benclothiaz, calcium cyanamide, calcium polysulfide, DSP, flonicamid, flurimfen, formetanate, hydrogen phosphide, metam-ammonium, metam- sodium, methyl bromide, potassium oleate, spiromesifen, Sulfoxaflor, sulfur, metaflumizone, spirotetramat ,
  • X al represents a methyl group, a chlorine atom, a bromine atom or a fluorine atom
  • X a2 represents a fluorine atom, a chlorine atom, a bromine atom, a C1-C4 haloalkyl group or a C1-C4 haloalkoxy group
  • X a3 represents a fluorine atom, a chlorine atom or a bromine atom
  • X a4 represents an optionally substituted C1-C4 alkyl group, an optionally substituted C3-C4 alkenyl group, an optionally substituted C3-C4 alkynyl group, an optionally substituted C3-C5
  • X a5 represents a hydrogen atom or a methyl group
  • X a6 represents a hydrogen atom, a fluorine atom or a chlorine atom
  • X 7
  • X b2 represents an optionally substituted Ci-C 4 haloalkyl group such as a 2 , 2 , 2-trifluoroethyl group or an optionally substituted C3-C6 cycloalkyl group such as a cyclopropyl group
  • X b3 represents an optionally substituted C1-C4 alkyl group such as a methyl group
  • X b4 represents a hydrogen atom, a chlorine atom, a cyano group or a methyl group.
  • X cl represents an optionally substituted C1-C4 alkyl group such as a 3, 3, 3-trifluoropropyl group, an optionally substituted C1-C4 alkoxy group such as a 2,2,2- trichloroethoxy group, an optionally substituted phenyl group such as a 4-cyanophenyl group or an optionally substituted pyridyl group such as a 2-chloro-3-pyridyl group, X c2 represents a methyl group or a
  • X c3 represents a methyl group or a halogen atom.
  • Examples of the active ingredient as the miticides include the followings:
  • BPPS propargite
  • Examples of the active ingredient as the nematicides include the followings:
  • DCIP fosthiazate
  • levamisol levamisol
  • methyisothiocyanate morantel tartarate
  • imicya.fos imicya.fos and the others.
  • Examples of the active ingredient as the fungicides include the followings:
  • procymidone iprodione, vinclozolin and the others;
  • Morpholine compounds dodemorph, tridemorph, fenpropimorph and the others;
  • azoxystrobin kresoxim-methyl , metominostrobin, trifloxystrobin, picoxystrobin, pyraclostrobin,
  • proquinazid cyflufenamid, bordeaux mixture, dichlofluani cyprodinil, pyrimethanil , mepanipyrim, diethofencarb, pyribencarb, famoxadone, fenamidone, zoxamide, ethaboxam, amisulbrom, iprovalicarb, benthiavalicarb, cyazofamid, mandipropamid, metrafenone, fluopiram, bixafen and the others .
  • Examples of the active ingredient as the synergists include the followings:
  • Examples of the subjects to be , controlled by the present herbicide include the followings:
  • Digitaria ciliaris Eleusine indica, Setaria viridis, Setaria faberi, Setaria glauca, Echinochloa crus-galli, Panicum dichotomiflorum, Panicum teXanum, Brachiaria platyphylla, Brachiaria plantaginea, Brachiaria decumbens, Sorghum halepense, Andropogon sorghum, Cynodon dactylon, Avena fatua, Lolium multiflorum, Alopecurus myosuroides, Bromus tectorum, Bromus sterilis, Phalaris minor, Apera spica-venti , Poa annua, Agropyron repens, Cyperus iria, Cyperus rotundus, Cyperus esculentus, Portulaca oleracea , Amaranthus retroflexus, Amaranthus hybridus, Amaranthus palmeri , Amarant
  • Sucher of perennial plants (such as pomaceous fruits, stone fleshy fruits, berry fruits, nuts, citrus fruits, hop and grape ) .
  • the present compound can be prepared, for example, according to the below-mentioned process.
  • the present compound of formula (la) can be prepared by reacting a compound of formula (2) and a compound of formula (3) in the presence of copper sulfate and sodium ascorbate .
  • the reaction is usually carried out in a solvent.
  • the solvent to be used in the reaction include nitriles such as acetonitrile; amides such as dimethylformamide; sulfoxides such as dimethyl sulfoxide; and mixed solvents thereof.
  • the amount used of the compound of formula (3) to be used in the reaction is usually within a range of 1 to 10 molar equivalents and preferably within a range of 1 to 3 molar equivalents as opposed to 1 mole of the compound of formula (2) .
  • the amount used of copper sulfate to be used in the reaction is usually within a range of 0.02 to 0.2 molar equivalents as opposed to 1 mole of the compound of formula (2) .
  • the amount used of sodium ascorbate to be used in the reaction is usually within a range of 0.05 to 0.5 molar equivalents as opposed to 1 mole of the compound of formula (2) .
  • the reaction temperature is usually within a range of 20 to 100°C.
  • the reaction period of the reaction is usually within a range of 10 minutes to 30 hours.
  • reaction mixtures are mixed with water .and are extracted with an organic solvent, and the resulting organic layers are treated (for example, drying and concentration) to obtain the compound of formula da) .
  • the present compound of formula (Id) can be prepared by reacting a compound of formula (4) and trimethylsilyl iodide (hereinafter, sometimes described as ' 'TMSI' ' ) .
  • the reaction is usually carried out in a solvent under an inert gas atmosphere.
  • solvent to be used in the reaction include aromatic hydrocarbons such as benzene, toluene and xylene; ethers such as diethyl ether, diisopropylether, dioxane, tetrahydrofuran and
  • halogenated hydrocarbons such as
  • dichloromethane chloroform and 1 , 2-dichloroethane ; amides such as dimethylformamide and dimethylacetamide; sulfones such as sulfolane; and mixed solvents thereof.
  • Examples of the inert gas to be used in the reaction - include nitrogen and argon.
  • the amount used of trimethylsilyl iodide to be used in the reaction is usually within a range of 1 molar
  • the reaction temperature is usually within a range of -80 to 180°C, preferably within a range of -80 to 50°C and more preferably within a range of -20 to 40°C.
  • the reaction period of the reaction is usually within . a range of 10 minutes to 30 hours.
  • reaction mixtures are mixed with water, and are extracted with an organic solvent, and the resulting organic layers are treated (for example, drying and concentration) to obtain the compound of formula (lb) .
  • the present compound of formula (id) wherein G represents G 1 can be prepared by reacting a compound of
  • G 1 represents a group of any one of the formulae:
  • X 1 represents a halogen atom (for example, a chlorine atom, a bromine atom, an iodine atom and the like) or an Ci-3 alkylsulfonyloxy group optionally substituted with, one or more halogen atoms (for example, a methylsulfonyloxy group, a . trifluoromethylsulfonyloxy group) or a group of a formula: OG 1 (with the proviso that when G 1 represents a group of formula:
  • X 1 represents a halogen atom or an C1-3 alkylsulfonyloxy group optionally substituted with one or more halogen atoms) ;
  • the reaction is usually carried in a solvent.
  • the solvent to be used includes aromatic hydrocarbons such as benzene and toluene; ethers such as diethyl ether, diisopropylether, dioxane, tetrahydrofuran and dimethoxyethane; halogenated hydrocarbons such as dichloromethane, chloroform and 1 , 2-dichloroethane; amides such as dimethylformamide and dimethylacetami.de; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; and mixed solvents thereof.
  • Examples of the compound of formula (5) to be used in the reaction include carboxylic halides such as acetyl chloride, propionyl chloride, isobutyryl chloride, pivaloyl chloride, benzoyl chloride and cyclohexanecarboxylic acid chloride; carboxylic anhydrides such as acetic anhydride and trifluoroacetic anhydride; halides of carbonate half ester such as methyl chloroformate , ethyl chloroformate and phenyl chloroformate; carbamic halides such as dimethylcarbamoyl chloride; sulfonic halides such as methanesulfonyl chloride and p-toluenesulfonyl chloride; sulfonic anhydrides such as methanesulfonic anhydride and trifluoromethanesulfonic anhydride; alkyl halogenoalkyl ethers such as chloromethyl methyl ether
  • the amount used of the compound of formula (5) to be used in the reaction is usually within a range of 1 molar equivalent or more and preferably within a range of 1 to 3 molar equivalents as opposed to 1 mole of the compound of formula ( lc ) .
  • the reaction is usually carried out in the presence of a base.
  • a base examples include organic bases such as triethylamine , tripropylamine , pyridine, dimethylaminopyridine, 1 , 8-diazabicyclo [ 5.4.0 ] -7- undecene; and inorganic bases such as sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, calcium carbonate and sodium hydride.
  • the amount used of the base is usually within a range of 0.5 to 10 molar equivalents and preferably within a range of 1 to 5 molar equivalents as opposed to 1 mole of the compound of formula (lc) .
  • the reaction temperature is usually within a range of -30 to 180°C and preferably within a range of -10 to 50°C.
  • the reaction period of the reaction is usually :within a range of 10 minutes to 30 hours.
  • the completion of the reaction can be confirmed by sampling a part of the reaction mixtures followed by performing analytical means such as thin-layer chromatography and high-performance liguid chromatography.
  • the reaction mixtures are mixed with water and are extracted with an organic solvent, and the resulting organic layers are treated (for example, drying and concentration) to obtain the compound of formula (Id) .
  • the compound of formula (5) is a known compound, or may be prepared from a known compound.
  • the compounds that are prepared according to the above-mentioned processes 1 to 3 may be isolated and/or purified by other known means such as concentration, concentration under reduced pressure, extraction, re- extraction, crystallization, recrystallization and chromatography.
  • the compound of formula (2) can be prepared, for example, by reacting a compound of formula (6) and sodium azide in the presence, of 15-crown 5-ether.
  • R 1 , R 2 R 3 f n and Z are the same as, defined above;
  • R 8 represents an Ci_ 6 alkyl group or an C6-10 aryl group (with the proviso that the Ci- 6 alkyl group and the C6-10 aryl group may have optionally one or more halogen atoms, when two or more halogen atoms exist, the halogen atoms may be same or different to each other; and the C6-10 aryl group may have optionally one or more Ci- 6 alkyl groups, and when two or more Ci- 6 alkyl groups exist, the alkyl groups may be same or different to each other) ;
  • G 2 represents a hydrogen atom, a benzyl group or a group of the following formula:
  • the reaction is usually carried out in a solvent.
  • Examples of the solvent to be used in the reaction include amides such as dimethylformamide and dimethylacetamide;
  • sulfoxides such as dimethyl sulfoxide; and mixed solvents thereof .
  • the amount used of sodium azide to be used in the reaction is usually within a range of 1 to 20 molar
  • the amount used of 15-crown 5-ether to be used in the reaction is usually within a range of 0.02 to 0.2 molar equivalents as opposed to 1 mole of the compound of formula (6) .
  • the reaction temperature is usually within a range of -10 to 120°C.
  • the reaction period of the reaction is usually within a range of 10 minutes to.30 hours.
  • reaction completion can be confirmed by analyzing a part of the reaction mixtures on analytical means such as thin-layer chromatography and high- performance liquid chromatography.
  • analytical means such as thin-layer chromatography and high- performance liquid chromatography.
  • the compound of formula (6) can be prepared, for example, by reacting, a compound of formula (7a) and a compound of formula (8) .
  • the reaction is usually carried out in a solvent.
  • the solvent to be used in the reaction include aromatic hydrocarbons such as benzene and toluene; ethers such as diethyl ether, diisopropylether, dioxane, tetrahydrofuran and dimethoxyethane; halogenated hydrocarbons such as dichloromethane, chloroform and 1,2- dichloroethane; amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; and mixed solvents thereof.
  • Examples of the compound of formula (8) to be used in the reaction include sulfonic halides such as methanesulfonyl chloride and p-toluenesulfonyl chloride.
  • the amount used of the compound of formula (8) to be used in the reaction is usually within a range of 1 molar equivalent or more and preferably within a range of 1 to 3 molar equivalents as opposed to 1 mole of the compound of formula (7a) .
  • the reaction is usually carried out in the presence of a base.
  • the base to be used in the reaction include organic bases such as triethylamine , tripropylamine, pyridine, dimethylaminopyridine , 1 , 8-diazabicyclo [ 5.4.0 ] -7- undecene; and inorganic bases such as sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, calcium carbonate and sodium hydride.
  • the amount used, of the base to be used in the reaction is usually within a range of 0.5 to 10 molar equivalents and preferably within a range of 1 to 5 molar equivalents as. opposed to 1 mole of the compound of formula ( 7a ) .
  • the reaction temperature is usually within a range of -30 to 180°C and preferably within a range of -10 to 50°C.
  • the reaction period of the reaction is usually within a range of 10. minutes to 30 hours.
  • reaction completion can be confirmed by analyzing a part of the reaction mixtures on analytical means such as thin-layer chromatography and high- performance liquid chromatography.
  • analytical means such as thin-layer chromatography and high- performance liquid chromatography.
  • the reaction mixtures are mixed with water and are extracted with an organic solvent, and the resulting organic layers are. treated (for example, drying and concentration) to obtain the compound of formula (6) .
  • the compound of formula (8) is a known compound, or may be prepared from a known compound.
  • the compound of formula (7) can be prepared by, for example, according to the following method.
  • G 3 represents a benzyl group or a para- methoxybenzyl group; and G 2 , R 1 , R 2 , R 3 , Z and n are the. same as defined above]
  • a compound of formula (12) can be prepared, for exmaple, according to a method described in JP 63-146856 A.
  • a compound of formula (10) can be prepared, for example, by reacting a compound of formula (12) and a compound of formula (11) in the presence of a base.
  • the reaction is usually carried out in a solvent.
  • the solvent to be used in the reaction include aromatic hydrocarbons such as benzene, toluene and xylene; ethers such as diethyl ether, diisopropylether, dioxane, tetrahydrofuran and dimethoxyethane; halogenated hydrocarbons such as dichloromethane, chloroform and 1,2- dichloroethane; amides . such as dimethylformamide and. dimethylacetamide; sulfones such as sulfolane; and mixed solvents thereof. .
  • Examples of the base to be used in the reaction include organic bases such as triethylamine, tripropylamine , pyridine, dimethylaminopyridine , 1 , 8-diazabicyclo [ 5.4.0 ] -7- undecene.
  • the amount used of the base to be used in the reaction is usually within a range of 1 to 10 molar equivalents and preferably within a range of 2 to 5 molar equivalents as opposed to 1 mole of the compound of formula (12).
  • the amount used of the compound of formula (11) to be used in the reaction is usually within a range of 1 to 3 molar equivalents as opposed to 1 mole of the compound of formula ( 12 ) .
  • the reaction temperature is usually within a range of -60 to 180°C and preferably within a range of -10 to 100°C.
  • the reaction period of this reaction is usually within a range of 10 minutes to 30 hours.
  • reaction completion can be confirmed by analyzing a part of the reaction mixtures on analytical means such as fhin-layer chromatography and high- performance liquid chromatography.
  • analytical means such as fhin-layer chromatography and high- performance liquid chromatography.
  • A. compound of formula (9) can be prepared, for example, by reacting a compound of formula (10) and a compound of formula: G 2 -X 1 in the presence of a base.
  • the reaction is usually carried out in a solvent.
  • the solvent to be used in the reaction include aromatic hydrocarbons such as benzene and toluene; ethers such as diethyl ether, diisopropylether, dioxane, tetrahydrofuran and dimethoxyethane; halogenated hydrocarbons such as dichloromethane, chloroform and 1,2- dichloroethane; amides such as . dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; and mixed solvents thereof.
  • Examples of the compound of formula: G 2 -X 1 to be used in the reaction include carboxylic halides such as acetyl chloride, propionyl chloride, isobutyryl chloride, pivaloyl chloride, benzoyl chloride and cyclohexanecarboxylic acid chloride; halides of carbonate ester, such as methyl chloroformate, ethyl chloroformate and phenyl chloroformate; and carbamic halides such as dimethylcarbamoyl chloride .. '
  • the amount used of the compound of formula: G 2 -X 1 to be used in the reaction is usually within a range of 1 molar equivalent or more and preferably within a range of 1 to 3 molar equivalents as opposed to 1 mole of the compound of formula ( 10 ) .
  • Examples of the base to be . used in the reaction include organic bases such as triethylamine, tripropylamine, pyridine, dimethylaminopyridine, 1, 8-diazabicyclo [5.4.0] -7- undecene; and inorganic bases such as sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, calcium carbonate and sodium hydride.
  • organic bases such as triethylamine, tripropylamine, pyridine, dimethylaminopyridine, 1, 8-diazabicyclo [5.4.0] -7- undecene
  • inorganic bases such as sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, calcium carbonate and sodium hydride.
  • the amount used of the base is usually within a range of 0.5 to 10 molar equivalents and preferably within a range of 1 to 5 molar equivalents as opposed to 1 mole of the compound of formula (10) .
  • the reaction temperature is usually within a range of -30 to 180°C and preferably within a range of -10 to 50°C.
  • the reaction period of this reaction is usually within a range of 10 minutes to 30 hours.
  • reaction completion can be confirmed by analyzing a part of the reaction mixtures on analytical means such as thin-layer chromatography and high- performance liquid chromatography.
  • analytical means such as thin-layer chromatography and high- performance liquid chromatography.
  • the resulting mixtures are mixed with water, and are extracted with an organic solvent, and the resulting organic layers are treated (for example, drying and concentration) to obtain the compound of formula (9).
  • the compound of formula: G 2 -X 1 is a known compound, or may be prepared from a known compound.
  • a compound of formula (7) can be prepared, for example, by reacting a compound of formula (9) and a compound of formula (B) .
  • the reaction is usually carried out in a solvent.
  • the solvent to be used in the reaction include aromatic hydrocarbons such as benzene and toluene; ethers such as diethyl ether, diisopropylether, dioxane, tetrahydrofuran and dimethoxyethane; alcohols such as methanol and ethanol; esters such as ethyl acetate; and mixed solvents thereof.
  • Examples of the compound of formula (B) to be used in the reaction include palladium, platinum and ammonium cerium (IV) nitrate.
  • the amount used of the compound of formula (B) to be used in the reaction is usually within a range of 1 molar equivalent or more and preferably within a range of 1 to 5 molar equivalents as opposed to a mole of the compound of formula (9) .
  • the reaction temperature ' is usually within a range of -30 to 180°C and preferably within a range of -10 to 50°C.
  • the reaction period of this reaction is usually within a range of 10 minutes to -30 hours.
  • reaction mixtures are filtered through Celite (registered trademark) and the resulting filtrates are treated (for example, concentration under, reduced pressure) to obtain the compound of formula (7) .
  • a compound of formula (4) can be prepared, for example, by reacting a compound of formula (17) and a compound of formula ( 18 ) .
  • R 1 , R 2 , R 3 , R 4 , n and Z are the same as defined above; and X represents a hydrogen atom (for example, a chlorine atom, a bromine atom, an iodine atom and the like) ].
  • the reaction is usually carried out in a solvent.
  • the solvent to be used in the reaction include ethers such as diethyl ether, diisopropylether, dioxane, tetrahydrofuran and dimethoxyethane; and mixed solvents thereof.
  • the amount used of the compound of formula (18) to be used in the reaction is usually within a range of 1 to 10 molar equivalents and preferably within a range of 2 to 5 molar equivalents as opposed to 1 mole of the compound of formula ( 17 ) .
  • the reaction temperature is usually within a range of -30 to 180°C and preferably within a range of -10 to 100°C.
  • the reaction period of the reaction is usually within a range of 10 minutes to 30 hours.
  • the completion of the reaction can be confirmed by analyzing a part of the reaction mixtures on analytical means such as thin-layer chromatography and high- performance liquid chromatography.
  • analytical means such as thin-layer chromatography and high- performance liquid chromatography.
  • the resulting mixtures are mixed with water, and are extracted with an organic solvent, and the resulting organic layers are treated (for example, drying and concentration) to obtain the compound of formula (4).
  • the compound of formula (18) can be prepared, for exmaple, according to a method described in Journal of Medicinal Chemistry 2007, 50, p.6212.
  • a compound of formula (17). can be prepared, for example, by reacting a compound of formula (19) and a compound of formula (A) .
  • the reaction is usually carried out in a solvent.
  • the solvent to be used in the reaction include aromatic hydrocarbons such as benzene, toluene and xylene; ethers such as diethyl ether, diisopropylether, dioxane, tetrahydrofuran and dimethoxyethane ; halogenated hydrocarbons such as dichloromethane, chloroform and 1,2- dichloroethane; amides such as dimethylformamide and dimethylacetamide ; sulfones such as sulfolane; and mixed solvents thereof, and preferably include halogenated hydrocarbons such as dichloromethane, chloroform and 1,2- dichloroethane .
  • Examples of the compound (A) to be used in the reaction include thionyl chloride, phosphorus tribromide, phosphorus triiodide and l-chloro-2-methyl-l-propenyl dimethylamine, and preferably include l-chloro-2-methyl-l- propenyl dimethylamine.
  • the amount used of the compound (A) to be used in the reaction is usually within a range of 1 molar equivalent or more and preferably within a range of 1 to 2 molar equivalents as opposed to 1 mole of the compound of formula (19).
  • the reaction temperature is usually within a range of -30 to 150°C and preferably within a range of -10 to 30°C.
  • the reaction period of the reaction is usually within a range of 10 minutes to 30 hours.
  • the completion of the reaction can be confirmed by sampling a part of the reaction mixtures followed by concentrating the reaction mixtures under reduced pressure and performing analytical means such as nuclear magnetic resonance instrument on the resulting organic ' materials.
  • analytical means such as nuclear magnetic resonance instrument
  • the reaction mixtures are treated (for example, concentration under reduced pressure) to obtain the compound of formula (17).
  • a compound of formula (19) can be prepared, for exma le, by oxidizing a compound of formula (20).
  • a compound of formula (20) can be prepared, for example,
  • solvent to be used in the reaction examples include aromatic hydrocarbons such as benzene and toluene; halogenated hydrocarbons such as dichloromethane and chloroform; and mixed solvents thereof.
  • oxidizing agent to be used in the reaction examples include an oxidizing agent consisting of a combination of iodosobenzene . diacetate and 2,2,6,6- tetramethylpiperidine 1-oxyl, manganese dioxide, pyridinium chlorochromate (PCC) , pyridinium dichromate (PDC) , , Dess- Martin periodinane and N-tert-butylbenzenesulfinimidoyl chloride.
  • PCC pyridinium chlorochromate
  • PDC pyridinium dichromate
  • Dess- Martin periodinane and N-tert-butylbenzenesulfinimidoyl chloride.
  • the amount used of the oxidizing agent to be used in the reaction is usually within a range of 1 to 10 molar equivalents as opposed to 1 mole of the compound of formula (7b) .
  • the reaction temperature is usually within a range of 0 to 150°C.
  • the reaction period of the reaction is usually within a range of 5 minutes to 100 hours.
  • the progress of the reaction can be confirmed by analyzing a part of the reaction mixtures on analytical means such as thin-layer chromatography and high- performance liquid chromatography.
  • analytical means such as thin-layer chromatography and high- performance liquid chromatography.
  • the reaction mixtures are mixed with water and are extracted with an organic solvent, and the resulting organic layers are treated (for example, drying and concentration) to obtain the compound of formula (20).
  • a compound of formula (II) can be prepared by, for example, reacting a compound of formula (21) with zinc tetraacetate in the presence of a base according to a method described in Marie-Luise Huber and John T. Pinhey, Journal of Chemical Society Perkin Transion 1 (1990), p.721.
  • the compound of formula (21) is a known compound, or may be prepared from a known compound.
  • the compound of formula (21) can be prepared, for example, according to a method described in JP 2008-133252 or a similar method thereto.
  • the compound of formula (a-b) means the present compound (a-b) .
  • the ''room . temperature' 1 (hereinafter sometimes abbreviated to as ' ' RT ' ' ) described in Preparation Examples and Reference Examples means usually 10 to 30°C.
  • 1 H NMR means a proton nuclear magnetic resonance spectrum and Tetramethyl silane is used as an internal standard and chemical shift ( ⁇ ) is expressed in ppm.
  • CDCI 3 Deuterated chloroform
  • D 2 O Deuterated water
  • s singlet
  • d doublet
  • t triplet
  • q quartet
  • m multiplet
  • Me methyl group
  • Et ethyl group
  • OMe methoxy group
  • OAc acetoxy group
  • Bn benzyl group
  • Ms mesyl group
  • PMP p- methoxyphenyl group
  • TMS trimethylsilyl group
  • EtOAc ethyl acetate.
  • a compound of formula (9-1) 18.0 g was dissolved in ethyl acetate 300 ml. To the resulting solution was 10% palladium-carbon 9.0 g and the resulting mixture was stirred at 35°C for 18 hours. The reaction mixed solution was filtered through Celite (registered trademark) and the obtained filtrate was concentrated under reduced pressure to afford a compound of formula (7-1) 16.1 g.
  • a compound of formula (7-1) 300 mg and diisopropylethylamine 0.36 ml were dissolved in N,N- dimethylformamide (10 ml) . To the resulting mixture was added under ice-cooling methanesulfonyl chloride 115 mg (1.0 mmol) drop wise and the resulting mixture was stirred at RT for 1 hour. To the reaction mixture was added water and the resulting mixture was extracted with tert-butyl methyl ether. The organic layer was dried over anhydrous MgS0 4 and concentrated under reduced pressure to afford crude product of a compound of formula (6-1) .
  • the compound of formula (2-1) 110 mg and l-ethynyl-4-fluorobenzene 88 mg were dissolved in a mixed solution of acetonitrile 5 ml and dimethylsulfoxide 1 ml, and to the resulting mixed solution ' ere added sodium ascorbate 7 mg and copper sulfate ' 3 mg, and the resulting mixture was heated under reflux for about 5 hours.
  • the obtained reaction mixed solution was then concentrated under reduced pressure and purified by column chromatography (Si0 2 ) by eluting with EtOAc: hexane (3: 1) to afford a compound of formula (1-1) 92 mg.
  • the obtained filtrate was extracted with chloroform and the organic layer was washed with water and dried over anhydrous Na 2 S0 4 and filtered.
  • the obtained filtrate was concentrated under reduced pressure to afford yellow oil.
  • the obtained oil was purified by column chromatography (Si0 2 ) by eluting. with EtOAc: hexane (1: 2) to afford a compound of formula (10-2) 28.0 g.
  • a compound of formula (9-2) 21.9 g was dissolved in a mixed solution of acetonitrile 120 ml and water 30 ml. To the resulting mixed solution was added under ice-cooling cerium ammonium nitrate 59.4 g. The resulting reaction solution was stirred at the same temperature for about 3. hours and thereto was then added water 300 ml, and the organic layer was washed with 10% aqueous sodium sulfite solution and dried over anhydrous Na 2 S0 4 .
  • the compound of formula (18-1) can be prepared, for example, according to a method described in Journal of Medicinal Chemistry 2007, 50, p.6212.
  • the compound of formula (18-2) can be prepared, for example, according to a method described in Journal of Medicinal Chemistry 2007, 50, p.6212.
  • the compound (1-1) is replaced with any of the compounds (1-2) to (1-20) to obtain respective formulations.
  • the compound (1-1) is replaced with any of the compounds (1-2) to (1-20) to obtain respective formulations.
  • the compound (1-1) is replaced with any of the compounds (1-2) to (1-20) to obtain respective formulations.
  • the chemical diluted solution was prepared by dissolving a predetermined amount of the compound (1-1) in dimethylformamide solution containing 2% of Tween 20 (polyoxyetylene sorbitan fatty acid ester) (manufactured by MP Biomedicals Inc.) and then diluting the solution with deionized water. After spraying, plants were grown in a greenhouse and after 20 days of the treatment, the efficacy for Echinochloa crus-galli was observed and the controlling effect was evaluated.
  • Tween 20 polyoxyetylene sorbitan fatty acid ester

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  • Chemical & Material Sciences (AREA)
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  • Pest Control & Pesticides (AREA)
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  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

Abstract

La présente invention propose un composé ayant une excellente efficacité pour lutter contre des mauvaises herbes. L'invention concerne un composé cyclohexanone de la formule (I) dans laquelle n est un entier quelconque de 1 à 5 ; R1 représente un atome d'hydrogène ou un groupe méthyle ; R2 et R3 représentent un atome d'hydrogène, un groupe alkyle C1-6 et similaires ; Q représente un groupe des formules définies dans la description ; R4 représente un groupe aryle C1-6 ou un groupe hétéroaryle à cinq à six éléments ; G représente un atome d'hydrogène et similaire ; et Z représente un atome d'halogène, un groupe cyano, un groupe nitro, un groupe phényle, un groupe alkyle C1-6 et similaires ; ledit composé étant utile en tant qu'ingrédient actif pour des herbicides.
PCT/JP2013/082651 2012-11-30 2013-11-28 Composés cyclohexanones et herbicides les comprenant WO2014084410A1 (fr)

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Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4209532A (en) 1977-03-28 1980-06-24 Union Carbide Corporation Biocidal 2-aryl-1,3-cyclohexane dione compounds and alkali metal and ammonium salts thereof
US4303669A (en) 1980-03-25 1981-12-01 Union Carbide Corporation Hybrid 1,3-dione-carbamate compounds
US4351666A (en) 1980-06-27 1982-09-28 Union Carbide Corporation Enol derivatives of 2-aryl-1,3-cyclohexanedione compound as sugar enhancer for plants
US4409513A (en) 1980-04-30 1983-10-11 Rca Corporation Electrode for an electron gun
US4659372A (en) 1977-03-28 1987-04-21 Union Carbide Corporation Biocidal 2-aryl-1,3-cyclohexanedione enol ester compounds
WO2001017972A2 (fr) 1999-09-07 2001-03-15 Syngenta Participations Ag Nouveaux herbicides
WO2003059065A1 (fr) 2002-01-15 2003-07-24 Bayer Cropscience Aktiengesellschaft Ceto-enols cycliques substitues par un biphenyle
JP2008133252A (ja) 2006-03-17 2008-06-12 Sumitomo Chemical Co Ltd ピリダジノン化合物及びそれを含有する除草剤
WO2008110308A2 (fr) 2007-03-09 2008-09-18 Syngenta Participations Ag Nouveaux herbicides
WO2010046194A1 (fr) 2008-10-20 2010-04-29 Syngenta Limited Nouveaux herbicides

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4209532A (en) 1977-03-28 1980-06-24 Union Carbide Corporation Biocidal 2-aryl-1,3-cyclohexane dione compounds and alkali metal and ammonium salts thereof
US4659372A (en) 1977-03-28 1987-04-21 Union Carbide Corporation Biocidal 2-aryl-1,3-cyclohexanedione enol ester compounds
US4303669A (en) 1980-03-25 1981-12-01 Union Carbide Corporation Hybrid 1,3-dione-carbamate compounds
US4409513A (en) 1980-04-30 1983-10-11 Rca Corporation Electrode for an electron gun
US4351666A (en) 1980-06-27 1982-09-28 Union Carbide Corporation Enol derivatives of 2-aryl-1,3-cyclohexanedione compound as sugar enhancer for plants
WO2001017972A2 (fr) 1999-09-07 2001-03-15 Syngenta Participations Ag Nouveaux herbicides
WO2003059065A1 (fr) 2002-01-15 2003-07-24 Bayer Cropscience Aktiengesellschaft Ceto-enols cycliques substitues par un biphenyle
JP2008133252A (ja) 2006-03-17 2008-06-12 Sumitomo Chemical Co Ltd ピリダジノン化合物及びそれを含有する除草剤
WO2008110308A2 (fr) 2007-03-09 2008-09-18 Syngenta Participations Ag Nouveaux herbicides
WO2010046194A1 (fr) 2008-10-20 2010-04-29 Syngenta Limited Nouveaux herbicides

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
J. AM. CHEM. SOC., vol. 130, 2008, pages 13110 - 13119
JOURNAL OF MEDICINAL CHEMISTRY, vol. 50, 2007, pages 6212
MARIE-LUISE HUBER; JOHN T. PINHEY, JOURNAL OF CHEMICAL SOCIETY PERKIN TRANSION, vol. 1, 1990, pages 721

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