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WO2004011429A1 - Nouveaux derives d'haloalkylsulfonanilide, herbicides et utilisation de ceux-ci - Google Patents

Nouveaux derives d'haloalkylsulfonanilide, herbicides et utilisation de ceux-ci Download PDF

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Publication number
WO2004011429A1
WO2004011429A1 PCT/JP2003/009405 JP0309405W WO2004011429A1 WO 2004011429 A1 WO2004011429 A1 WO 2004011429A1 JP 0309405 W JP0309405 W JP 0309405W WO 2004011429 A1 WO2004011429 A1 WO 2004011429A1
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group
alkyl
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Japanese (ja)
Inventor
Tomokazu Hino
Takashi Shimaoka
Yuzo Miura
Koki Mametsuka
Takahiro Kiyokawa
Shinji Murata
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Nihon Nohyaku Co Ltd
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Nihon Nohyaku Co Ltd
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    • 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
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur 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
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • 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
    • 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
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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

Definitions

  • the present invention relates to a sulfonanilide derivative or a salt thereof, a herbicide containing the compound as an active ingredient, and a method for using the herbicide.
  • dipheninoleether derivatives having a perfluoroalkylsulfonylamino group as a substituent have been known to be useful as herbicides or anti-inflammatory agents (for example, US Pat. No. No description or suggestion is made for skeletons other than diphenyl ether.
  • perfluoroalkyl sulfonanilide derivatives having a phenoxy group, a phenylthio group, a phenylsulfonyl group or the like as substituents are useful as herbicides or anti-inflammatory agents (for example, see German Patent Application Publication No.
  • a perrea derivative having a trifluoromethanesulfonylamino group as a substituent is useful as a herbicide (for example, see JP-A-60-87254). It is known that pyrazine derivatives having a trifluoromethanesulfonylamino group are useful as herbicides (see, for example, US Pat. No. 4,345,076).
  • the haloalkyl sulfonanilide derivative represented by the general formula (I) of the present invention is neither described nor suggested, and the haloalkyl sulfonyl derivative represented by the general formula (I) of the present invention is not described.
  • a sulfonanilide derivative having a 2-pyrimidinyloxy group at the 4-position and a herbicide containing the compound as an active ingredient are known. See Japanese Unexamined Patent Publication No. Hei 8—1931011 or Japanese Unexamined Patent Publication No. Hei 8-292911. It is described that rice has no phytotoxicity and its applicability to paddy fields, but the skeleton is different from that of the haloalkylsulfonanilide derivative represented by the general formula (I) of the present invention. There is no particular description or suggestion about this.
  • sulfonanilide derivatives having a pyrimidinyloxy group at the 2-position useful as herbicides for example, International Publication No. 93Z0909 pamphlet, International Publication No.
  • a sulfonanilide derivative compound useful as a herbicide having an aminomethylene group or an iminomethylene group in the bond between the 2-position of pyrimidine and the 2-position of aniline see, for example, Japanese Patent Application Laid-Open No. 2-1495677). Japanese Patent Application Laid-Open No.
  • a trifluoromethanesulfonanilide derivative having a pyrimidinyl group at the 2-position and an alkoxyalkyl group at the 6-position is used for paddy fields with low toxicity to mammals. It is useful as a herbicide (for example, see Japanese Patent Application Laid-Open No. 2000-633600), and difluoromethanesulfur having a dimethoxypyrimidinylhydroxymethyl group at the 2-position.
  • An anilide derivative is known as a herbicide having selectivity for rice (see, for example, JP-A-2000-44546). Both of these compounds have a dimethoxypyrimidinyl group or the like.
  • haloalkylsulfonanilide derivative represented by the general formula (I) of the present invention a nodroalkylsulfonanilide and a heterocycle are bonded via an alkylene group or the like.
  • the compound having the skeleton is not described or suggested. Also, their workability as herbicides is different.
  • a sulfonanilide derivative is a novel compound that has not been described in the literature. It has wide applicability to species, long-lasting effect, and excellent properties such as selectivity between crops and weeds, and has been found to be useful as a herbicide, particularly as a paddy field herbicide, and completed the present invention. Things. Disclosure of the invention
  • the present invention provides a compound of the general formula (I):
  • R 1 represents a halo (C Factory C 6 ) alkyl group.
  • R 2 is a hydrogen atom, a (C 6 C) alkyl group, a (CC 6 ) alkoxy (CfC 6 ) alkyl group, a (-C 6 ) alkyl carbonyl group, a nodro (() alkylcarbonyl group, a phenylcarbonyl group A substituted phenylcarbonyl group having at least one substituent selected from Y (Y is shown below), (-c 6 ) alkoxycaponyl group, phenoxycarbonyl group May be the same or different, and a substituted phenyloxycarbonyl group having at least one substituent selected from ⁇ ( ⁇ is described below), (C Factory C 6 ) alkylsulfonyl group, phenol (C Factory C 6 ) represents an alkylsulfonyl group, a phenylsulfonyl group or a substituted phenylsulfonyl group which may be the same or different and has one or more substituent
  • Q represents an optionally substituted heterocycle in which at least one of the constituent atoms is a nitrogen atom, and the nitrogen atom is a bonding site with A.
  • A is a (Cf C 6 ) alkylene group, which may be the same or different, and is selected from a halogen atom, a hydroxyl group, a (C Factory C 6 ) alkoxy group, a (C-Cs) alkoxycarbonyl group or a cyano group 1 or more substitutions having substituent (c r c 6) alkylene group, (c 2 - c 6)
  • Aruke two alkylene groups, the same or different and a halogen atom, a hydroxyl group, (C ⁇ c 6) an alkoxy group shows the - (c 6 c 2) alkenylene or (c 2 -c 6) alkynylene group (Cr) alkoxycarbonyl group or substituted with one or more location substituent selected from Shiano group.
  • G is an oxygen atom, a sulfur atom, N—R 3 (where R 3 is a hydrogen atom, an alkyl group of. (C Factory C 6 ), a cyano group, a nitro group, a phenyl (C Factory C 6 ) alkyl group, the same or A substituted phenyl (C-wide C 6 ) alkyl group having at least one substituent selected from Y (Y will be described below) on the ring, a phenyl group, or the same or different; Y represents a substituted phenyl group having at least one substituent selected from the following.), N—OR 4 (wherein, is a hydrogen atom, a (C r C 6 ) alkyl group, phenyl) (c r c 6 ) alkyl group or the same or different, and Y (Y is shown below) You.
  • R 5 and R 6 may be the same or different, may be a hydrogen atom, a phenyl group or the same or different, and are selected from Y (Y is shown below.) And R 5 and R 6 may be taken together to represent a (C 3 -C 6 ) alkylene group.
  • n an integer of 0 or 1.
  • X may be the same or different; a hydrogen atom, a halogen atom, a (C 2 C 6 ) alkyl group, a (C 2 -C 6 ) alkenyl group, a (C 2 -C 6 ) alkynyl group, a cyclo (C 3 -C 6 ) Alkyl group, Noro (C Factory C 6 ) alkyl group, cycloha (C 3 -C 6 ) alkyl group, (C Factory C 6 ) alkoxy group, halo (C Factory C 6 ) alkoxy group, (-C 6) alkylthio groups, halo (C ⁇ c 6) alkylthio groups, (C ⁇ C 6) alkylsulfinyl group, Nono port (C ⁇ c 6) alkylsulfinyl group, (c r c 6) alkylsulfonyl group, /, mouth (C factory c 6 ) alkylsulfony
  • Substituted phenyl having at least one substituent selected from (Cfc 6 ) represents 1 to 4 substituents selected from an alkylaminocarbonyl group, a hydroxyl group, an amino group, a cyano group and a nitro group.
  • Y may be the same or different, a halogen atom, (C t -C 6) alkyl group, (C 2 - C 6) ⁇ alkenyl group, (c 2 - C 6) alkynyl group, consequent opening (C 3 - C 6) alkyl group, halo (C ⁇ c 6) Al kill group, Shikuroha port (C 3 - C 6) alkyl groups, (C ⁇ C 6) alkoxy groups, halo (C ⁇ C 6) alkoxy groups, (C Factory C 6 ) alkylthio group, halo (-C 6 ) alkylthio group, (CFactory c 6 ) alkinolesulfinyl group, nodro (C r C 6 ) alkylsulfinyl group, (CFactory c 6 ) alkylsulfonyl group, Halo (C factory c 6 ) alkylsulfonyl group, phenyl group
  • C Factory 6 Substituted phenyl having 1 to 5 substituents on the ring selected from an alkylaminocarbonyl group, a hydroxyl group, an amino group, a cyano group or a nitro group.
  • Rua amino carbonyl group phenyl (C ⁇ c 6) alkyl ⁇ Mino Cal Group, which may be identical or different, halogen atom, (C ⁇ C 6) alkyl groups, (C 2 - C 6) alkenyl, (C 2 - C 6) alkynyl, cyclo (C 3 - C 6) Alkyl group, halo (C factory c 6 ) alkyl group, cycloha (C 3 -C 6 ) alkyl group, (C factory c 6 ) alkoxy group, halo (c r c 6 ) alkoxy group, (( ⁇ -C 6) alkylthio group, Bruno, mouth (C, - C B) alkylthio groups, (C -!) alkyl sulfide group, Nono b (CC 6) alkylsulfinyl group, (C ⁇ c e) an alkylsulfonyl group, Nodro (d-C 6
  • Y may be the same as or different from adjacent carbon atoms on the benzene ring, and may be an oxygen atom, a sulfur atom, or a nitrogen atom (the nitrogen atom is a hydrogen atom, a (C Factory C 6 ) alkyl group, C 2 - C 6) Al Group, may be interrupted by - - (c 6 c 3) 1 to hetero atoms two of the selected from may) be substituted by an alkyl group (c 2 c 6) alkynyl group or a cycloalkyl.
  • a (d-C 4 ) alkylene group may form a 5- or 6-membered ring.
  • halogen atom represents a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.
  • the “(-C 6 ) alkylene group” is a linear or branched C 1-6 alkylene such as methylene, ethylene, propylene, trimethylene, dimethylenolethylene, tetramethylene, isoptylene, dimethylethylene, and hexamethylene.
  • (C r C 6 ) alkyl group means, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, neopentyl, n — Represents a linear or branched alkyl group having 1 to 6 carbon atoms such as hexyl.
  • “(: ⁇ ) haloalkyl group” means a straight or branched alkyl group having 1 to 6 carbon atoms, which may be the same or different and may be substituted with one or more halogen atoms.
  • (C 3 -C 6 ) cycloalkynole group refers to an alicyclic group having 3 to 6 carbon atoms such as cyclopropynole, cycloptynole, cyclopentynole, cyclohexynole, 2-methylcyclopentyl, and 2-methylcyclopentyl. Shows a formula alkyl group.
  • (C Factory C 6 ) alkoxy group means, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, s-butoxy, t-butoxy, n-pentinoleoxy, isopentyloxy, neopentyl A linear or branched alkoxy group having 1 to 6 carbon atoms such as oxy, n-hexyloxy and the like.
  • halo (Cr) alkoxy group refers to a straight or branched alkyl group having 1 to 6 carbon atoms substituted by one or more halogen atoms, which may be the same or different.
  • (C r C 6 ) alkoxycarbonyl group means, for example, methoxycarbonyl, ethoxycanoleponinole, n-propoxycanoleponinole, isopropoxycanoleboninole, n-butoxycarbonyl, t-butoxycarbonyl, etc. It represents a linear or branched alkoxy group having 1 to 6 carbon atoms.
  • (C Factory C 6 ) alkylthio group means, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, s-butylthio, t-butylthio, n-pentylthio, isopentylthio, n-hexylthio, etc. It represents a chain or branched alkylthio group having 1 to 6 carbon atoms.
  • (-) Alkyl sulfier group means, for example, methylsorefininole, ethinolesnorefinole, n-propinoresorefininole, isopropinoles norefininole, n-butinoresorefininole , S-butynolesulfininole, t-butynoles norefininole, n —pentinolesnorefininole, isopentylsnorefininole, n —hexylsulfinyl and other straight or branched chain carbon atoms Represents 1 to 6 alkylsulfinyl groups.
  • (C Factory C 6 ) alkylsulfonyl group means, for example, methylsulfonyl, ethynolesnorefonyl, n-propynolesulfoninole, isopropylsnolehoninole, n-butynolesnorefonyl, s-butino Straight or branched chain carbon atoms of 1 to 6 such as lesnolephonyl, t-butinoresolephoninole, n-pentinoresulfonolone, isopentylsnorefonyl, and n-hexinolesulfoninole Alkylsulfonyl groups.
  • the nitrogen atom Is a 4- to 13-membered hetero ring in which the bonding position with A is a nitrogen atom and contains the nitrogen atom, and the hetero ring is 4 to 8 A condensed ring in which a benzene ring or a 4 to 7-membered hetero ring is further condensed to a membered hetero ring.
  • the heterocyclic ring may include, in addition to one or more nitrogen atoms, other heteroatoms such as an oxygen atom, a sulfur atom, and a phosphorus atom.
  • GG 2 may be the same or different; oxygen atom, sulfur atom, N—R 3 ′ (wherein, R 3 ′ is a hydrogen atom, (C Factory C 6 ) alkyl group, cyano group, nitro group And a phenyl (CfC 6 ) alkyl group, which may be the same or different, and have a substituted phenyl (C Factory C 6) having at least one substituent selected from ⁇ ′ (where ⁇ ′ is described below) on the ring. ) Alkyl group, phenyl group or the same or different, and ⁇ , ( ⁇ , are shown below) It represents a substituted furyl group having one or more substituents selected. ), N—OR 4 '
  • R ′ 1 ′ may be a hydrogen atom, a ((C 6 C) alkyl group, a phenyl (C C 6 ) alkyl group or may be the same or different, and ⁇ ′ ( ⁇ ′ will be described later.)
  • J 1 is an oxygen atom, a sulfur atom, or N—R 9 (wherein R 9 is a hydrogen atom, a (-C 6 ) alkyl group, a phenyl (C-Factory C 6 ) alkyl group, which may be the same or different; , ( ⁇ , are shown below), a substituted phenyl (C r C 6 ) alkyl group having at least one substituent selected from the following on the ring, a phenyl group, which may be the same or different, and Y ′ ( Y and are described below.)
  • a substituted fuunyl group having one or more substituents selected from the group consisting of a heterocyclic group and a heterocyclic group may be the same or different.
  • (Ci-Cs) alkyl group (the heterocyclic group is as defined above.), Mono (C ⁇ C 6) alkylaminocarbonyl group, the same or different and may di (Cf) alkylaminocarbonyl group, Fueniruamino A carbonyl group or a substituted or unsubstituted phenylaminocarbonyl group having at least one substituent selected from ⁇ ′ ( ⁇ ′ is shown below) which may be the same or different. Show.
  • J 2 and J 3 may be the same or different, and include an oxygen atom, a sulfur atom, N—R 9 (wherein R 9 is as defined above), R 1Q —C—R 11 (wherein R 1Q and Pi R 11 may be the same or different, a hydrogen atom, (c -!
  • J 4 and J 5 may be the same or different, and C—R 12 (where R 12 is a hydrogen atom, a halogen atom, a (C Factory C 6 ) alkyl group, a halo (C Factory C 6 ) alkyl group , (C Factory C 6 ) alkoxy group, Haguchi (CFactory C 6 ) alkoxy group, (Cf C 6 ) alkylthio group, Haguchi (CFactory C 6 ) alkylthio group, (CfCs) alkylsulfinyl group, nodro ( C factory c 6 ) alkylsulfinyl group, (c r c 6 ) alkynolesnorefonyl group, nodro (C factory C 6 ) anorecylsulfoninole group, phenyl (C factory c 6 ) alkyl group, same or different And a phenyl (C Factory c 6 )
  • J 6 represents an oxygen atom, a sulfur atom, N_R 9 (where R 9 is the same as described above), or R 1Q —C 1 R 11 (where R ll) and R ′′ are the same as described above).
  • R 9 is the same as above.
  • R 13 and R w may be the same or different, and may be a hydrogen atom, a halogen atom, a (C Factory C 6 ) alkyl group, a halo (C Factory C 6 ) alkyl group, a (C Factory C 6 ) alkoxy group, a halo (C "C 6 ) alkoxy group, (C Factory C 6 ) alkylthio group, halo (C Factory C 6 ) alkylthio group, (C Factory C 6 ) alkylsulfinyl group, ⁇ ⁇ (CFactory C 6 ) alkylsulfinyl group, A C r C 6 ) alkylsulfonyl group, a halo (C Factory C 6 ) alkylsulfonyl group, a phenyl (C r C 6 ) alkyl group may be the same or different, and ⁇ ( ⁇ ) is described below.
  • C Factory C 6 alkyl group, phenyl group having one or more substituents on the ring, which may be the same or different, and ⁇ ′ ( ⁇ ′ is shown below).
  • a heterocyclic (C ⁇ C 6 ) alkyl group (heterocyclic group Same as above.
  • R 15 and R 16 may be the same or different and represent a hydrogen atom or a (C Factory C 6 ) alkyl group.
  • X ′ may be the same or different, and include a hydrogen atom, a halogen atom, a (Cfc 6 ) alkyl group, a (c 2 -c 6 ) alkenyl group, a (c 2 -g alkynyl group, a cyclo (c 3 -c 7 ) alkyl group, Nono port (c ⁇ c 6) alkyl group, Shikuroha port (c 3 - 7) alkyl group, (c ⁇ c 6) alkoxy groups, halo
  • C factory c 6 anorequinoles refininole group, phenol (c r c 6 ) anore cyls norefinyl group, (c r c 6 ) anorekylsulfonyl group, phenol (C factory C 6 ) an alkylsulfonyl group, a phenyl group, the same or different, and a substituted phenyl group, a phenoxy group having one or more substituents selected from ⁇ ′ ( ⁇ ′ is described below). May be the same or different;
  • C factory c 6 alkylaminocarbonyl group, same or different di ((: c 6 ) alkylaminocarbonyl group, phenylaminocarbonyl group, same or different A substituted phenylaminocarbonyl group having one or more substituents selected from the group consisting of Y ′ ( ⁇ ′ is described below), phenyl (C Factory c 6 ) alkylaminocarbinole Groups, which may be the same or different, are selected from ⁇ , ( ⁇ 'is shown below)
  • substituents selected from a substituted phenyl (CfCe) alkylaminocarboxy group, a hydroxyl group, an amino group, a cyano group and a nitro group having at least one substituent on a ring.
  • Y may be the same or different, and include a hydrogen atom, a halogen atom, a (c r c 6 ) alkyl group, a (c 2 -c 6 ) alkenyl group, a (c 2 -c 6 ) alkynyl group, a cyclo (c 3- c 6 ) alkyl group, phenol (c factory c 6 ) alkyl group, cycloha (c 3 -c 6 ) alkyl group, (-alkoxy group, phenol (C factory C 6 ) alkoxy group, (C r C 6 ) Alkylthio group, halo (-Ce) alkylthio group,
  • the groups represented can be mentioned.
  • heterocyclic group examples include a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyrazinyl group, a triazinole group, a furyl group, a tetrahydrofuryl group, a phenyl group, a tetrahydrophenyl group, a tetrahydrovinylanyl group, and a tetrahydrovinyl group.
  • Examples thereof include a thiopyranyl group, an oxazolyl group, an isoxazolyl group, an oxdiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, an imidazolyl group, a triazolyl group, a pyrazolyl group, and a morpholinyl group.
  • the salt of the haloalkylsulfonanilide derivative of the present invention may be any salt that can be used when applied as a pesticide, for example, salts with an alkali metal such as lithium salt, sodium and potassium, calcium and magnesium Salts with alkaline earths such as, salts with heavy metals such as iron, salts with inorganic metals such as salts with other metals such as aluminum and zinc, salts with organic bases such as ammonium salts, etc. These may form hydrates.
  • the haloalkylsulfonanilide derivative represented by the general formula (I) of the present invention may contain one or more asymmetric carbon atoms or asymmetric centers in its structural formula, and may have two or more types.
  • Optical isomers and diastereomers may exist, and the present invention includes all optical isomers and mixtures containing them in any ratio.
  • the haloalkylsulfonanilide derivative represented by the general formula (I) of the present invention has two kinds of geometric isomers derived from a carbon-carbon double bond or a carbon-nitrogen double bond in its structural formula.
  • the present invention encompasses all geometric isomers and mixtures containing them in any proportion.
  • the heterocycle of Q is a 5-membered to 6-membered compound containing 1 to 4 nitrogen atoms, 0 to 1 oxygen atom and 0 to 1 sulfur atom. It is also preferable that the 5- or 6-membered hetero ring forms a condensed ring. Particularly preferred are Q-1, Q-2, Q-3 and the like.
  • Suitable as the substituent on Q is, phenyl (C ⁇ C 6) alkyl group, a substituted phenyl (C ⁇ C 6) alkyl group, Hue group, a substituted phenyl group, pyridyl group and substitution pyridyl group is there.
  • the haloalkyl as R 1 is preferably fluoromethyl, more preferably trifluoromethyl or difluoromethyl, and the substitution position is preferably the 2-position.
  • R 2 is preferably a hydrogen atom.
  • G and G 1 are preferably oxygen atoms.
  • m is preferably 0.
  • haloalkylsulfonamide derivative represented by the general formula (I) of the present invention can be produced, for example, by the production method shown below.
  • R 2 ′ is a (Cf C 6 ) alkyl group, (C 6 -C 6 ) alkyl A carbonyl group, a nitro group (C Factory C 6 ) alkyl carbonyl group, which may be the same or different, and a phenylcarbonyl group having at least one substituent selected from Y (Y is the same as described above); c 6) alkyl sulfonyl group, a halo (C ⁇ c 6) alkylsulfonyl group, or the same or different and may, Y (Y is phenylene Noresuruho radicals having 1 or more substituents selected from the same.) to the Is shown.
  • L represents a leaving group such as a halogen atom.
  • the compound represented by the general formula (II) is reacted with a heterocyclic compound represented by the general formula QH in the presence of a base and, if necessary, using a phase transfer catalyst in the presence or absence of an inert solvent.
  • the compound represented by the general formula (III) is reacted to give a compound represented by the general formula (I) by isolating or not isolating the compound and reacting with a reducing agent or the like in the presence or absence of an inert solvent.
  • An amino compound represented by the formula (IV) is isolated or isolated without isolation, and is prepared by the reaction of I ⁇ S 0 2 _L (in the formula, in the presence of a base, in the presence or absence of an inert solvent) R 1 and L are the same as described above.) Or (1 ⁇ 3 ⁇ 2 ) 2 R (wherein, R 1 is the same as described above.) By reacting a haloalkylsulfonyl derivative represented by the general formula ( 1 ). The compound of the present invention represented by 1-1) can be produced.
  • the compound represented by the general formula (1-1) is isolated or not isolated, and the compound represented by the general formula R 2 — L (wherein, and in the presence of a base, in the presence or absence of an inert solvent)
  • the compound of the present invention represented by the general formula (1-2) can be produced by reacting the compound represented by the same formula.
  • the compound represented by the general formula (1-1) or (1-2) is isolated or not isolated, and in the presence or absence of an inert solvent, the compound represented by the general formula H 2 N—R 3 ( In the formula, R 3 is the same as described above.)
  • the heterocyclic ring represented by Q—H is, for example, 2,3-dihydro 3H-1,2,41-triazol-3-one derivative can be prepared by the method described in WO 98-381176 or the like.
  • tetrazole derivatives can be produced by the method described in J. Heterocycl. Chem., 35 (2), 405 (1998) or the like, or other heterocycles represented by Q—— are described in international patents. Publication W ⁇ 91-3470, J. Chem.
  • the inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include linear or cyclic ethers such as getyl ether, tetrahydrofuran, and dioxane, and benzene, toluene, and xylene.
  • linear or cyclic ethers such as getyl ether, tetrahydrofuran, and dioxane, and benzene, toluene, and xylene.
  • Ketones such as acetonitrile, esters such as ethyl acetate, amides such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, 1,3
  • inert solvents such as —dimethyl-2-imidazolinone and water. These inert solvents may be used alone or in combination of two or more. To be able to use.
  • Bases that can be used in this reaction include, for example, nitrogen-containing organic bases such as triethylamine, diisopropinoletinoleamine, 1,8-diazabicyclo mouth [5.4.0] 17-indene, pyridine, sodium carbonate, and carbonic acid.
  • Inorganic bases such as lime, sodium bicarbonate, sodium hydroxide, sodium hydroxide, sodium hydride, sodium metal, etc .; organic bases such as sodium acetate, sodium acetate; alcohol such as sodium methoxide and potassium t-butoxide And the like.
  • the base may be used in an amount sufficient to neutralize the acid generated by the reaction, but may be used in excess.
  • phase transfer catalyst examples include tetra n- 3 009405
  • phase transfer catalyst examples thereof include quaternary ammonium salts such as dimethylpromide and benzyltriethylammonium bromide, and crown ethers such as 18-crown-16-ether.
  • the amount of the phase transfer catalyst to be used may be appropriately selected from the range of from 0.01 to 1.5 times the mol of the compound represented by the general formula ( ⁇ ).
  • each reactant may be used in an equimolar amount, but any amount of the reactant may be used in excess.
  • the reaction can be carried out at a temperature of from 120 ° C. to the reflux temperature of the used inert solvent.
  • the reaction time is not fixed depending on the reaction scale, the reaction temperature, etc., but is appropriately in the range of several minutes to 48 hours. Just choose.
  • the target product can be produced by isolating the target product from the reaction system containing the target product by a conventional method and, if necessary, purifying the product by a recrystallization method, a distillation method, a column chromatography method or the like. Further, after the completion of the reaction, the target product can be used for the next reaction without isolation.
  • inert solvent examples include alcohols such as methanol and ethanol, ethers such as tetrahydrofuran and dioxane, and water. These inert solvents may be used alone or in combination of two or more. Can be used in combination. Further, an aqueous solution of an acid used as a reducing agent described below can be used as an inert solvent as it is.
  • Examples of the reducing agent that can be used in this reaction include metal monoacids and metal monoliths.
  • Examples of the metal include iron, tin, and zinc, and examples of the acid include minerals such as hydrochloric acid and sulfuric acid.
  • Acids, organic acids such as acetic acid and the like, tin chloride and the like, and examples of the salt include salt water ammonium and the like. It is also possible to use them in combination.
  • the amount of the reducing agent used is 1 to 10 times the molar amount of the compound represented by the general formula ( ⁇ ), and the acid and salt are appropriately selected from the range of 0.05 to 10 times the molar amount. I should do it.
  • the reaction temperature may be selected from the range of 0 ° C. to 150 ° C., and the reaction time is not constant depending on the reaction scale, the reaction temperature, and the like, but may be appropriately selected within the range of several minutes to 48 hours.
  • the reduction can also be carried out by catalytic hydrogenation in the presence of a catalyst.
  • a catalyst examples include palladium carbon, platinum, Raney nickel and the like.
  • the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method, and purifying the product, if necessary, by a recrystallization method, a distillation method, a column chromatography method or the like. Further, after the completion of the reaction, the target product can be used for the next reaction without isolation.
  • the inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction.
  • examples include linear or cyclic ethers such as getyl ether, tetrahydrofuran, and dioxane; benzene, toluene, and xylene.
  • Ketones such as acetonitrile, esters such as ethyl acetate, amides such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2- Inert solvents such as imidazolinone can be exemplified. These inert solvents may be used alone or in combination of two or more. Can be used.
  • Bases that can be used in this reaction include, for example, nitrogen-containing organic bases such as triethylamine, diisopropylethynoleamine, 1,8-diazabicycline [5.4.0] -17-indene, pyridine, sodium carbonate, carbonated lime, and the like.
  • Inorganic bases such as sodium hydrogencarbonate, sodium hydroxide, hydroxylated sodium, hydrogenated sodium, metal sodium, etc .
  • organic bases such as sodium acetate, sodium acetate
  • alcoholate such as sodium methoxide, potassium t-butoxide, etc.
  • nitrogen-containing organic bases such as pyridine can also be used as the solvent.
  • the base may be used in an amount sufficient to neutralize the acid generated by the reaction, but may be used in excess.
  • each reactant may be used in an equimolar amount, but any of the reactants may be used in excess.
  • the reaction can be carried out at a temperature of from 120 ° C to the reflux temperature of the inert solvent used.
  • the reaction time depends on the reaction scale, reaction temperature, etc. Although it is not constant, it may be appropriately selected in the range of several minutes to 48 hours.
  • the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method, and purifying the product, if necessary, by a recrystallization method, a distillation method, a column chromatography method or the like. Further, after the completion of the reaction, the target product can be used for the next reaction without isolation.
  • This reaction can be carried out according to (1-3).
  • the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method, and purifying the product, if necessary, by a recrystallization method, a distillation method, a column chromatography method or the like. Further, after the completion of the reaction, the target product can be used for the next reaction without isolation.
  • Any inert solvent may be used as long as it does not significantly inhibit the progress of this reaction.
  • examples thereof include alcohols such as methanol, ethanol, n-propanol, and the like, and chain or cyclic ethers such as getyl ether, tetrahydrofuran, and dioxane.
  • Aromatic hydrocarbons such as benzene, toluene, and xylene, and halogenated aromatic hydrocarbons such as benzene and dichlorobenzene, and these inert solvents can be used alone or individually. Two or more can be used in combination.
  • Examples of the acid that can be used in this reaction include organic acids such as formic acid, acetic acid, and propionic acid, and mineral acids such as hydrochloric acid and sulfuric acid.
  • each reactant may be used in an equimolar amount, but any of the reactants may be used in excess.
  • the reaction can be carried out at a temperature of from 120 ° C. to the reflux temperature of the used inert solvent.
  • the reaction time is not fixed depending on the reaction scale, the reaction temperature, etc., but is appropriately in the range of several minutes to 48 hours. Just choose.
  • the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method, and purifying the product, if necessary, by a recrystallization method, a distillation method, a column chromatography method or the like.
  • R 17 is an amino group, 2-hydroxyethyla It represents a mino group or a hydrazino group.
  • the compound represented by the general formula (V) as a starting material is described in, for example, J. Chem. Soc., 1 800 (1925), J. Chem. Soc., 2348 (1 926), or the like, or can be produced according to them.
  • haloalkylsulfonanilide derivatives represented by the general formula (I) of the present invention are shown in Tables 1 to 13, but the present invention is not limited thereto.
  • the physical properties indicate the melting point (° C) or the refractive index.
  • Me represents a methyl group
  • E t represents an ethyl group
  • P r represents a propyl group
  • Bu represents a butyl group
  • P en represents a pentyl group
  • H ex is a hexyl group
  • Ph is a phenyl group
  • Pyn is a pyridyl group
  • ⁇ ym is a pyrimidyl group
  • P yd is a pyridazyl group
  • Ac is an acetyl group.
  • substitution position indicates the substitution position of the alkylsulfonylamino group.

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Abstract

L'invention concerne des dérivés d'haloalkylsulfonanilide représentés par la formule générale (I) et leurs sels ; des herbicides contenant ces composés, et leur utilisation. Dans la formule, R1 représente halo(C1-C6)alkyle ; R2 représente H, alkyle en C1-C6 ou analogue ; A représente alkylène en C1-C6 ou analogue ; G représente OS, NR3 ou analogue ; m égale 0 ou 1 ; X représente phényle substitué, phénoxy ou analogue ; et Q représente un hétérocycle éventuellement substitué comportant au moins un atome d'azote constitutif du noyau, par lequel l'hétérocycle est lié à A.
PCT/JP2003/009405 2002-07-26 2003-07-24 Nouveaux derives d'haloalkylsulfonanilide, herbicides et utilisation de ceux-ci Ceased WO2004011429A1 (fr)

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US7312248B2 (en) * 2004-09-23 2007-12-25 Schering-Plough Animal Health Corporation Control of parasites in animals by the use of novel trifluoromethanesulfonanilide oxime ether derivatives
US7906538B2 (en) * 2004-09-23 2011-03-15 Schering-Plough Animal Health Corporation Control of parasites in animals by the use of novel trifluoromethanesulfonanilide oxime ether derivatives
KR100890886B1 (ko) * 2005-02-24 2009-03-31 니혼노야쿠가부시키가이샤 신규 할로알킬설폰아닐리드 유도체, 제초제 및 이의 이용방법
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