WO2015097071A1 - Dérivés haloalkylsulphonamide herbicides - Google Patents

Dérivés haloalkylsulphonamide herbicides Download PDF

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Publication number
WO2015097071A1
WO2015097071A1 PCT/EP2014/078594 EP2014078594W WO2015097071A1 WO 2015097071 A1 WO2015097071 A1 WO 2015097071A1 EP 2014078594 W EP2014078594 W EP 2014078594W WO 2015097071 A1 WO2015097071 A1 WO 2015097071A1
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alkyl
atom
group
phenyl
haloalkyl
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PCT/EP2014/078594
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English (en)
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Yoshihide Masuzawa
Yoshihiko Nakaya
Yosuke Nakayama
Yuuki MIYAKADO
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Syngenta Participations Ag
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
    • C07D211/86—Oxygen 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing >N—S—C≡(Hal)3 groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/38—2-Pyrrolones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
    • C07D223/12—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to novel halo alky lsulphonamide derivatives and salts thereof, and agrichemicals which contain the said haloalkylsulphonamide derivatives and salts thereof as active component, and in particular to herbicides.
  • agrichemical in the present invention means insecticide, acaricide, nematocide, herbicide, bactericide and the like.
  • the purpose of the present invention is to provide chemical substances which reliably display efficacy against various weeds at lower dosages and with which problems such as soil contamination, effects on future crops and the like are alleviated, which are very safe, and are useful as effective components of herbicides.
  • novel haloalkylsulphonamide derivatives represented by the following formula (1) of the present invention are very useful compounds which have excellent herbicidal activity as herbicides and are very safe towards the crops concerned, and have practically no harmful effects on non-target animals such as mammals, fish and beneficial insects, and thus accomplished the present invention.
  • the present invention relates to a haloalkylsulphonamide derivative represented by the formula (1):
  • W represents an oxygen atom or a sulphur atom
  • X represents a halogen atom, Ci-C 6 alkyl, Ci-C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, cyano, - C(0)R 46 , hydroxy, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy, amino, nitro or -S(0) q yR 49 , and when m represents a whole number 2 or more, the respective X may be the same or different, further, if 2 X are adjacent, the 2 adjacent X, by forming -CH 2 CH 2 CH 2 -, -CH 2 CH 2 0-, -CH 2 OCH 2 -, - OCH2O-, -CH2CH2S-, -CH
  • R 1 represents Ci-C 6 haloalkyl
  • R 2 represents a hydrogen atom, Ci-C 6 alkyl, (Ci-C 6 ) alkyl optionally substituted with R 10 , C 3 -C 6 cycloalkyl, (C 3 -C 6 ) cycloalkyl optionally substituted with R 10 , C 2 -C 6 alkenyl, (C 2 -C 6 ) alkenyl optionally substituted with R 10 , C 2 -C 6 alkynyl, (C 2 -C 6 ) alkynyl optionally substituted with R 10 , -C(0)R n or -S(0) 2 R 12 ,
  • R 3 and R 4 each independently represent a hydrogen atom, halogen atom, Ci-C 6 alkyl, Ci-C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, Ci-C 6 alkoxy or Ci-C 6 haloalkoxy or else R 3 by forming a C 2 -C 6 alkylene chain together with R 4 can form a 3 to 7-membered ring together with the carbon atom linking R 3 and R 4 ,
  • R 5 represents a hydrogen atom, Ci-C 6 alkyl, (Ci-C 6 ) alkyl optionally substituted with R 27 , C 3 -C 6 cycloalkyl, (C 3 -C 6 ) cycloalkyl optionally substituted with R 27 , C 2 -C 6 alkenyl, (C 2 -C 6 ) alkenyl optionally substituted with R , C 2 -C 6 alkynyl, (C 2 -C 6 ) alkynyl optionally substituted with R 27 , -C(0)R 28 , -S(0) 2 R 30 or D-l to D-9,
  • R 6 and R 7 each independently represent a hydrogen atom, halogen atom, Ci-C 6 alkyl, (Ci-C 6 ) alkyl optionally substituted with R 39 , C 3 -C 6 cycloalkyl, (C 3 -C 6 ) cycloalkyl optionally substituted with R 39 , C 2 -C 6 alkenyl, (C 2 -C 6 ) alkenyl optionally substituted with R 39 , C 2 -C 6 alkynyl, (C 2 -C 6 ) alkynyl optionally substituted with R 39 , phenyl, phenyl substituted with (R 40 ) q5 , -C(0)R 41 , cyano, -OR 42 or -S(0) q6 R 43 or else R 6 and R 7 on the same carbon, by together forming a C 2 -C 6 alkylene chain, can form a 3 to 7-membered ring together with the linking carbon atom, and in this
  • R 8 and R 9 each independently represent a hydrogen atom, halogen atom, Ci-C 6 alkyl, (Ci-C 6 ) alkyl optionally substituted with R 39 , C 3 -C 6 cycloalkyl, (C 3 -C 6 ) cycloalkyl optionally substituted with R 39 , C 2 -C 6 alkenyl, (C 2 -C 6 ) alkenyl optionally substituted with R 39 , C 2 -C 6 alkynyl, (C 2 -C 6 ) alkynyl optionally substituted with R 39 , phenyl, phenyl substituted with (R 40 ) q5 , -C(0)R 41 , cyano, -OR 42 or -S(0) q6 R 43 or else R 8 together with R 9 on the same carbon, by forming a C 2 -C 6 alkylene chain, can form a 3 to 7-membered ring together with the linking carbon atom, and in this
  • R 10 represents a halogen atom, phenyl, phenyl substituted with (R 13 ) q i, -C(0)R 14 , -OR 15 or -
  • R 1 1 represents C 1 -C 12 alkyl, (C 1 -C 12 ) alkyl optionally substituted with R 20 , C 3 -C 6 cycloalkyl, (C 3 -C 6 ) cycloalkyl optionally substituted with R 20 , C 2 -C 6 alkenyl, (C 2 -C 6 ) alkenyl optionally substituted with R 20 , C 2 -C 6 alkynyl, (C 2 -C 6 ) alkynyl optionally substituted with R 20 , phenyl, phenyl substituted with (R 13 ) q i, -OR 21 , -N(R 22 )R 23 or -SR 24 ,
  • R 12 represents Ci-C 6 alkyl, Ci-C 6 haloalkyl, phenyl, phenyl substituted with (R 13 ) q i or -
  • R 13 represents a halogen atom, Ci-C 6 alkyl, Ci-C 6 haloalkyl, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy, amino or nitro and when ql represents a whole number 2 or more, the respective R 13 may be the same or different, further, if 2 R 13 are adjacent, the 2 adjacent R 13 , by forming
  • R 14 represents Ci-C 6 alkyl, Ci-C 6 haloalkyl, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy, phenyl or phenyl substituted with (R 13 ) q i
  • R 15 represents a hydrogen atom, Ci-C 6 alkyl, Ci-C 6 haloalkyl, phenyl, phenyl substituted with (R 13 ) q i or -C(0)R 16 ,
  • R 16 represents Ci-C 6 alkyl, phenyl, phenyl substituted with (R 13 ) q i, Ci-C 6 alkoxy or - N(R 17 )R 18
  • R 17 and R 18 each independently represent a hydrogen atom, Ci-C 6 alkyl or Ci-C 6 haloalkyl or else R 17 , together with R 18 , by forming a C 2 -C 6 alkylene chain, can form a 3 to 7-membered ring together with the linking nitrogen atom, and in this case this alkylene chain may contain 1 oxygen atom, sulphur atom or nitrogen atom, and can optionally be substituted with a halogen atom, Ci-C 6 alkyl group, Ci-C 6 haloalkyl group, Ci-C 6 alkoxy group, formyl group, Ci-C 6 alkylcarbonyl group, Ci-C 6 alkoxycarbonyl group or oxo group,
  • R 19 represents Ci-C 6 alkyl, Ci-C 6 haloalkyl, phenyl or phenyl substituted with (R 13 ) q i,
  • R 20 represents a halogen atom, C 3 -C 6 cycloalkyl, phenyl, phenyl substituted with (R 13 ) q i, Ci- C 6 alkoxy, Ci-C 6 haloalkoxy or phenoxy,
  • R 21 represents C 1 -C 12 alkyl, (C 1 -C 12 ) alkyl optionally substituted with R 20 , C 3 -C 6 cycloalkyl, (C 3 -C 6 ) cycloalkyl optionally substituted with R 20 , C 2 -C 6 alkenyl, (C 2 -Ce) alkenyl optionally substituted with R 20 , C 2 -C 6 alkynyl, (C 2 -Ce) alkynyl optionally substituted with R 20 , phenyl or phenyl substituted with (R 13 ) q i,
  • R 22 and R 23 each independently represent a hydrogen atom, Ci-C 6 alkyl or Ci-C 6 haloalkyl or else R 22 , together with R 23 , by forming a C 2 -C 6 alkylene chain, can form a 3 to 7-membered ring together with the linking nitrogen atom, and in this case this alkylene chain may contain 1 oxygen atom, sulphur atom or nitrogen atom, and can optionally be substituted with a halogen atom, Ci-C 6 alkyl group, Ci-C 6 haloalkyl group, Ci-C 6 alkoxy group, formyl group, Ci-C 6 alkylcarbonyl group, Ci-C 6 alkoxycarbonyl group or oxo group,
  • R 24 represents Ci-C 6 alkyl or Ci-C 6 haloalkyl
  • R 25 and R 26 each independently represent a hydrogen atom or Ci-C 6 alkyl or else R 25 , together with R 26 , by forming a C 2 -C 6 alkylene chain, can form a 3 to 7-membered ring together with the linking nitrogen atom, and in this case this alkylene chain may contain 1 oxygen atom, sulphur atom or nitrogen atom, and can optionally be substituted with a halogen atom, Ci-C 6 alkyl group, Ci-C 6 haloalkyl group, C 1 -C6 alkoxy group, formyl group, Ci-C 6 alkylcarbonyl group, Ci-C 6 alkoxycarbonyl group or oxo group,
  • R represents a halogen atom, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, -C(0)R , -OR , - N(R 33 )R 34 , -S(0) q4 R 35 , tri(Ci-C 6 alkyl)silyl or D-l to D-9
  • R 28 represents Ci-C 6 alkyl, Ci-C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy, -N(R 36 )R 37 or -SR 38 ,
  • R 29 represents a halogen atom, Ci-C 6 alkyl, Ci-C 6 haloalkyl, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy, amino or nitro and when q 3 represents a whole number 2 or more, the respective
  • R 29 may be the same or different, further, if 29 acent, the 29
  • R are adj 2 adjacent R , by forming -CH 2 CH 2 CH 2 -, -CH 2 CH 2 O-, -CH 2 OCH 2 -, -OCH 2 O-, -CH 2 CH 2 S-, -CH 2 SCH 2 -, -
  • R 30 represents Ci-C 6 alkyl, Ci-C 6 haloalkyl, phenyl or phenyl substituted with (R 29 ) q 3,
  • R 31 represents Ci-C 6 alkyl, Ci-C 6 haloalkyl, Ci-C 6 alkoxy or Ci-C 6 haloalkoxy,
  • R 32 represents a hydrogen atom, Ci-C 6 alkyl, Ci-C 6 haloalkyl, phenyl or phenyl substituted with (R 29 ) q3
  • R 33 and R 34 each independently represent a hydrogen atom or 33
  • Ci-C 6 alkyl or else R , together with R 34 , by forming a C 2 -C 6 alkylene chain, can form a 3 to 7-membered ring together with the linking nitrogen atom, and in this case this alkylene chain may contain 1 oxygen atom, sulphur atom or nitrogen atom, and can optionally be substituted with a halogen atom, Ci-C 6 alkyl group, Ci-C 6 haloalkyl group, Ci-C 6 alkoxy group, formyl group, Ci-C 6 alkylcarbonyl group, Ci-C 6 alkoxycarbonyl group or oxo group,
  • R 35 represents Ci-C 6 alkyl, Ci-C 6 haloalkyl, phenyl or phenyl substituted with (R 29 ) q 3,
  • R 36 and R 37 each independently represent a hydrogen atom, Ci-C 6 alkyl or Ci-C 6 haloalkyl or else R 36 , together with R 37 , by forming a C 2 -C 6 alkylene chain, can form a 3 to 7-membered ring together with the linking nitrogen atom, and in this case this alkylene chain may contain 1 oxygen atom, sulphur atom or nitrogen atom, and can optionally be substituted with a halogen atom, Ci-C 6 alkyl group, Ci-C 6 haloalkyl group, Ci-C 6 alkoxy group, formyl group, Ci-C 6 alkylcarbonyl group, Ci-C 6 alkoxycarbonyl group or oxo group,
  • R 38 represents Ci-C 6 alkyl or Ci-C 6 haloalkyl
  • R 39 represents a halogen atom, C 3 -C 6 cycloalkyl, phenyl, hydroxy, Ci-C 6 alkoxy or Ci-C 6 haloalkoxy
  • R 40 represents a halogen atom, Ci-C 6 alkyl, Ci-C 6 haloalkyl, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy, amino or nitro, and when q 5 represents a whole number 2 or more, the respective
  • R 40 may be the same or different, further, if 2 R 40 are adjacent, the 2 adjacent R 40 , by forming -CH 2 CH 2 CH 2 -, -CH 2 CH 2 O-, -CH 2 OCH 2 -, -OCH 2 O-, -CH 2 CH 2 S-, -CH 2 SCH 2 -, -
  • R 41 represents Ci-C 6 alkyl, Ci-C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, hydroxy, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy or -N(R 44 )R 45 ,
  • R 42 represents a hydrogen atom, Ci-C 6 alkyl, Ci-C 6 haloalkyl, phenyl or phenyl substituted with (R 40 ) q5
  • R 43 represents Ci-C 6 alkyl, Ci-C 6 haloalkyl, phenyl or phenyl substituted with (R 40 ) q 5
  • R 44 and R 45 each independently represent a hydrogen atom, Ci-C 6 alkyl or Ci-C 6 haloalkyl or else R 44 , together with R 45 , by forming a C 2 -C 6 alkylene chain, can form a 3 to 7-membered ring together with the linking nitrogen atom, and in this case this alkylene chain may contain 1 oxygen atom, sulphur atom or nitrogen atom, and can optionally be substituted with a halogen atom, Ci-C 6 alkyl group, Ci-C 6 haloalkyl group, Ci-C 6 alkoxy group, formyl group, Ci-C 6 alkylcarbonyl group, Ci-C 6 alkoxycarbonyl group or oxo group,
  • R 46 represents a hydrogen atom, Ci-C 6 alkyl, Ci-C 6 alkoxy or -N(R 47 )R 48 ,
  • R 47 and R 48 each independently represent a hydrogen atom or Ci-C 6 alkyl or else R 47 , together with R 48 , by forming a C 2 -C 6 alkylene chain, can form a 3 to 7-membered ring together with the linking nitrogen atom, and in this case this alkylene chain may contain 1 oxygen atom, sulphur atom or nitrogen atom, and can optionally be substituted with a halogen atom, Ci-C 6 alkyl group, Ci-C 6 haloalkyl group, Ci-C 6 alkoxy group, formyl group, Ci-C 6 alkylcarbonyl group, Ci-C 6 alkoxycarbonyl group or oxo group, R 49 represents Ci-C 6 alkyl or Ci-C 6 haloalkyl, q 1 represents a whole number 1, 2, 3, 4 or 5, q 2 represents a whole number 0, 1 or 2, q 3 represents a whole number 1, 2, 3, 4 or 5, q 4 represents a whole number 0, 1 or 2, q
  • the preferred groups for A, W, X, m, n, p, q, t and all R numbers in any combination thereof are as set out below.
  • W represents an oxygen atom.
  • R 2 represents a hydrogen atom, Ci-C 6 alkyl, (Ci-C 6 ) alkyl optionally substituted with R 10 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, -C(0)R n or -S(0) 2 R 12 . More preferably, R 2 represents a hydrogen atom or -C(0)R n .
  • R 3 and R 4 represent hydrogen atoms.
  • R 5 represents a hydrogen atom, Ci-C 6 alkyl, (Ci-C 6 ) alkyl optionally substituted with R 27 , C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, -C(0)R 28 or D-7. More preferably, R 5 represents a hydrogen atom, Ci-C 6 alkyl, (Ci-C 6 ) alkyl optionally substituted with R 27 , -C(0)R 28 or D-7.
  • R 10 represents phenyl, -C(0)R 14 , -OR 15 or -S(0) q2 R 19 .
  • R 11 represents Ci-Ci 2 alkyl, (Ci-Ci 2 ) alkyl optionally substituted with R 20 , C3-C6 cycloalkyl, C 2 -C 6 alkenyl, phenyl, -OR 21 or -SR 24 . More preferably, R 11 represents - OR 21 .
  • R 12 represents Ci-C 6 alkyl, Ci-C 6 haloalkyl, phenyl or phenyl substituted with (R 13 ) q i.
  • R 13 represents a halogen atom, Ci-C 6 alkyl, Ci-C 6 haloalkyl or Ci-C 6 alkoxy.
  • R 14 represents Ci-C 6 alkoxy or phenyl.
  • R 15 represents a hydrogen atom, Ci-C 6 alkyl or -C(0)R 16 .
  • R 16 represents Ci-C 6 alkyl or Ci-C 6 alkoxy.
  • R 19 represents Ci-C 6 alkyl.
  • R 20 represents a halogen atom or phenoxy.
  • R 21 represents C 1 -C 12 alkyl, (d-C 12 ) alkyl optionally substituted with R 20 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or phenyl. More preferably, R 21 represents d-C 6 alkyl.
  • R 24 represents Ci-C 6 alkyl.
  • R 27 represents a halogen atom, -C(0)R 31 , -OR 32 , tri(Ci-C 6 alkyl)silyl or D-
  • R 28 and R 31 each independently represent Ci-C 6 alkoxy.
  • R 32 represents d-C 6 alkyl.
  • R ⁇ 9 represents a halogen atom, phenyl, hydroxy or Ci-C 6 alkoxy.
  • R 41 represents hydroxy or Ci-C 6 alkoxy.
  • R 42 represents a hydrogen atom, Ci-C 6 alkyl or phenyl.
  • R 43 represents d-C 6 alkyl or phenyl.
  • the present invention provides a haloalkylsulphonamide derivative or salt thereof as described above wherein:
  • W represents an oxygen atom
  • R represents a hydrogen atom, Ci-C 6 alkyl, (d-C 6 ) alkyl optionally substituted with R , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, -C(0)R u or -S(0) 2 R 12 ,
  • R 3 and R 4 represent hydrogen atoms
  • R represents a hydrogen atom, Ci-C 6 alkyl, (Ci-C 6 ) alkyl optionally substituted with R , -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, -C(0)R 28 or D-7,
  • R 10 represents phenyl, -C(0)R 14 , -OR 15 or -S(0) q2 R 19 ,
  • R 11 represents Ci-Ci 2 alkyl, (Ci-Ci 2 ) alkyl optionally substituted with R 20 , C3-C6 cycloalkyl, C 2 -C 6 alkenyl, phenyl, -OR 21 or -SR 24
  • R 12 represents Ci-C 6 alkyl, Ci-C 6 haloalkyl, phenyl or phenyl substituted with (R 13 ) q i
  • R 13 represents a halogen atom, Ci-C 6 alkyl, Ci-C 6 haloalkyl or Ci-C 6 alkoxy,
  • R 14 represents Ci-C 6 alkoxy or phenyl
  • R 15 represents a hydrogen atom, Ci-C 6 alkyl or -C(0)R 16 ,
  • R 16 represents Ci-C 6 alkyl or Ci-C 6 alkoxy
  • R 19 represents Ci-C 6 alkyl
  • R 20 represents a halogen atom or phenoxy
  • R 21 represents Ci-Ci 2 alkyl, (Ci-Ci 2 ) alkyl optionally substituted with R 20 , C 2 -C 6 alkenyl, C 2 - C 6 alkynyl or phenyl,
  • R 24 represents Ci-C 6 alkyl
  • R 27 represents a halogen atom, -C(0)R 31 , -OR 32 , tri(Ci-C 6 alkyl)silyl or D-l,
  • R 28 and R 31 each independently represent Ci-C 6 alkoxy, R represents Ci-C 6 alkyl,
  • R 39 represents a halogen atom, phenyl, hydroxy or Ci-C 6 alkoxy,
  • R 41 represents hydroxy or Ci-C 6 alkoxy
  • R 42 represents a hydrogen atom, Ci-C 6 alkyl or phenyl
  • R 43 represents Ci-C 6 alkyl or phenyl.
  • the present invention provides a
  • R 5 represents a hydrogen atom, Ci-C 6 alkyl, (Ci-C 6 ) alkyl optionally substituted with R 27 , - C(0)R 28 or D-7, and R 6 , R 7 , R 8 and R 9 represent hydrogen atoms.
  • the present invention provides a
  • R 2 represents a hydrogen atom or -C(0)R n ,
  • R 1 1 represents -OR 21
  • R 21 represents Ci-C 6 alkyl
  • the present invention provides a pesticide containing as active component 1 or 2 or more selected from haloalkylsulphonamide derivatives or salts thereof as described above.
  • the present invention provides a herbicide containing as active component 1 or 2 or more selected from haloalkylsulphonamide derivatives or salts thereof as described above.
  • the herbicide is in the form of a composition comprising the active component and, in addition, at least one agriculturally acceptable adjuvant or diluent.
  • the present invention also provides the use of a
  • the present invention also provides a method of controlling plants which comprises applying to the plants or to the locus thereof a herbicidally effective amount of a haloalkylsulphonamide derivative or salts thereof as described above.
  • the present invention also provides a method of inhibiting plant growth which comprises applying to the plants or to the locus thereof a herbicidally effective amount of a haloalkylsulphonamide derivative or salts thereof as described above.
  • the present invention also provides a method of controlling weeds in crops of useful plants, comprising applying to said weeds or to the locus of said weeds, or to said useful crop plants, a compound or a composition of the invention.
  • the present invention also provides a method of selectively controlling grasses and/or weeds in crops of useful plants which comprises applying to the useful plants or locus thereof or to the area of cultivation a herbicidally effective amount of a haloalkylsulphonamide derivative or salts thereof as described above.
  • the compounds of the present invention have excellent herbicidal activity against various weeds and are very safe towards the crops concerned, have practically no harmful effects on non-target animals such as mammals, fish and beneficial insects, and as they have low residue, they are also low-polluting towards the environment.
  • the present invention can provide herbicides valuable in the field of farming and horticulture, for example in paddy fields, farms and orchards.
  • E-form and Z-form geometrical isomers may be present in the compounds included in the present invention, and the present invention includes these E-forms, Z-forms or mixtures containing the E-form and Z-form in any proportion.
  • optically active forms due to the presence of 1 or 2 or more asymmetric carbon atoms are present, and the present invention includes all optically active forms or racemic forms.
  • those which can be made into acid addition salts by usual methods can be made into salts of hydrogen halides such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, and hydriodic acid, salts of inorganic acids such as nitric acid, sulphuric acid, phosphoric acid, chloric acid and perchloric acid, salts of sulphonic acids such as methanesulphonic acid, ethanesulphonic acid, tri-fluoromethanesulphonic acid, benzenesulphonic acid and p-toluenesulphonic acid, salts of carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, and citric acid or salt
  • hydrogen halides such as hydrofluoric acid
  • those which can be made into metal salts by usual methods can for example be made into salts of alkali metals such as lithium, sodium and potassium, salts of alkaline earth metals such as calcium, barium and magnesium or salts of aluminium.
  • suitable salts also include those derived from ammonia and amines.
  • Preferred cations include ammonium cations of the formula N + (R 19 R 20 R 21 R 22 ) wherein R 19 , R 20 , R 21 and R 22 are independently selected from hydrogen, Ci-C 6 alkyl and Ci-C 6 hydroxyalkyl.
  • Salts of the compounds of formula (I) can be prepared by treatment of compounds of formula (I) with a metal hydroxide, such as sodium hydroxide, or an amine, such as ammonia, trimethylamine, diethanolamine, 2- methylthiopropylamine, bisallylamine, 2-butoxyethylamine, morpholine,
  • a metal hydroxide such as sodium hydroxide
  • an amine such as ammonia, trimethylamine, diethanolamine, 2- methylthiopropylamine, bisallylamine, 2-butoxyethylamine, morpholine
  • Amine salts are often preferred forms of the compounds of formula (I) because they are water-soluble and lend themselves to the preparation of desirable aqueous based herbicidal compositions.
  • n- means normal, i- iso, s- secondary, and tert- tertiary respectively, and Ph means phenyl.
  • halogen atoms in the present specification, the fluorine atom, chlorine atom, bromine atom and iodine atom are mentioned. It should be noted that "halo" in the present specification indicates these halogen atoms.
  • C a -C b alkyl in the present specification indicates a linear or branched hydrocarbon group with a number of carbon atoms a to b, for example methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, tert-butyl group, n-pentyl group, 1 , 1-dimethylpropyl group, n-hexyl group and the like are mentioned as specific examples, and they are selected in the respective specified carbon atom number range.
  • C a -C b cycloalkyl in the present specification indicates a cyclic hydrocarbon group made up of a number of carbon atoms a to b, and single ring or multiple ring structures of 3-membered rings to 6-membered rings can be formed. Further, each ring can be optionally substituted with alkyl groups with the specified numbers of carbon atoms.
  • cyclopropyl group, 1-methylcyclopropyl group, 2-methylcyclopropyl group, 2,2-dimethylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and the like are mentioned as specific examples, and they are selected in the respective specified carbon atom number range.
  • C a -C b alkenyl in the present specification indicates a linear or branched unsaturated hydrocarbon group with a number of carbon atoms a to b which has 1 or 2 or more double bonds in the molecule, for example a vinyl group, 1-propenyl group, 2-propenyl group, 1-methylethenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 3-methyl-2- butenyl group, l , l-dimethyl-2-propenyl group and the like are mentioned as specific examples, and they are selected in the respective specified carbon atom number range.
  • C a -C b alkynyl in the present specification indicates an unsaturated hydrocarbon group with a number of carbon atoms a to b which has 1 or 2 or more triple bonds in the molecule, for example an ethinyl group, 1-propinyl group, 2-propinyl group, 1- butinyl group, 2-butinyl group, 3-butinyl group, l ,l-dimethyl-2-propinyl group and the like are mentioned as specific examples, and they are selected in the respective specified carbon atom number range.
  • C a -C b haloalkyl in the present specification indicates a linear or branched hydrocarbon group made up of a number of carbon atoms a to b, wherein the hydrogen atoms linked to carbon atoms are optionally substituted with halogen atoms, and, in this case, if they are substituted with 2 or more halogen atoms, these halogen atoms can be the same or different.
  • halogen atoms can be the same or different.
  • bromomethyl group iodomethyl group, difluoromethyl group, dichloromethyl group, trifluoromethyl group, chlorodifluoromethyl group, trichloromethyl group,
  • bromodifluoromethyl group 2-fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2,2- trichloroethyl group, 1 , 1 ,2,2-tetrafluoroethyl group, 2-chloro- 1 , 1 ,2-trifluoroethyl group, pentafluoroethyl group, 3,3,3-trifluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 1 , 1 ,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group, 2,2,2-trifluoro-l- (trifluoromethyl)ethyl group, l ,2,2,2-tetrafluoro-l-(
  • 2,2,3,3,4,4,4-heptafluorobutyl group, nonafluorobutyl group and the like are mentioned as specific examples, and they are selected in the respective specified carbon atom number range.
  • C a -C b haloalkenyl in the present specification indicates a linear or branched unsaturated hydrocarbon group made up of a number of carbon atoms a to b, which has 1 or 2 or more double bonds in the molecule, wherein the hydrogen atoms linked to carbon atoms are optionally substituted with halogen atoms, and, in this case, if they are substituted with 2 or more halogen atoms, these halogen atoms can be the same or different.
  • the 1-chloroethenyl group, 2-chloroethenyl group, 2-fluoroethenyl group, 2,2- dichloroethenyl group, 3-chloro-2-propenyl group, 3-fluoro-2-propenyl group, 2-chloro-2- propenyl group, 4-chloro-3-butenyl group and the like are mentioned as specific examples, and they are selected in the respective specified carbon atom number range.
  • C a -C b haloalkynyl in the present specification indicates a linear or branched unsaturated hydrocarbon group made up of a number of carbon atoms a to b, which has 1 or 2 or more triple bonds in the molecule, wherein the hydrogen atoms linked to carbon atoms are optionally substituted with halogen atoms, and for example the chloroethinyl group, fluoroethinyl group, bromoethinyl group, 3-chloro-2-propinyl group, 4-chloro-2- butinyl group and the like are mentioned as specific examples, and they are selected in the respective specified carbon atom number range.
  • C a -C b alkoxy in the present specification indicates an alkyl-O- group wherein made up of a number of carbon atoms a to b has the aforesaid meaning, and for example the methoxy group, ethoxy group, propyloxy group, i-propyloxy group, butyloxy group, i-butyloxy group, s-butyloxy group, t-butyloxy group, pentyloxy group, 1- methylbutyloxy group, 2-methylbutyloxy group, 3-methylbutyloxy group, 1 , 1- dimethylpropyloxy group, 1 ,2-dimethylpropyloxy group, 2,2-dimethylpropyloxy group, 1- ethylpropyloxy group, hexyloxy group, 1-methylpentyloxy group, 2-methylpentyloxy group, 3-methylpentyloxy group, 4-methylpentyloxy group, 1 , 1-dimethylbutyloxy group, 1
  • C a -Cb haloalkoxy in the present specification indicates a haloalkyl-O- group, wherein made up of a number of carbon atoms a to b has the aforesaid meaning, and for example fluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, chlorodifluoromethoxy group, bromodifluoromethoxy group, dichloro fluoromethoxy group, chloromethoxy group, dichloromethoxy group, trichloromethoxy group, bromomethoxy group, 1-fluoroethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2-bromoethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, 1 ,1,2,2-tetrafluoroethoxy group, pentafluoroethoxy group, 2,2,2-trichloroethoxy group, 2,2,2-trifluoroeth
  • C a -C b alkylcarbonyl in the present specification indicates an alkyl- C(O)- group wherein made up of a number of carbon atoms a to b has the aforesaid meaning, and for example the CH 3 C(0)- group, CH 3 CH 2 C(0)- group, CH 3 CH 2 CH 2 C(0)- group, (CH 3 ) 2 CHC(0)- group, CH 3 (CH 2 ) 3 C(0)- group, (CH 3 ) 2 CHCH 2 C(0)- group,
  • CH 3 (CH 2 ) 5 C(0)- group and the like are mentioned as specific examples, and they are selected in the respective specified carbon atom number range.
  • the expression C a -C b alkoxycarbonyl in the present specification indicates an alkyl-O-
  • C(O)- group wherein made up of a number of carbon atoms a to b has the aforesaid meaning, and for example the CH 3 OC(0)- group, CH 3 CH 2 OC(0)- group, CH 3 CH 2 CH 2 OC(0)- group, (CH 3 ) 2 CHOC(0)- group, CH 3 (CH 2 ) 3 OC(0)- group, (CH 3 ) 2 CHCH 2 OC(0)- group,
  • (CH 3 ) 3 COC(0)- group and the like are mentioned as specific examples, and they are selected in the respective specified carbon atom number range.
  • the trimethylsilyl group, triethylsilyl group and the like are mentioned as specific examples of the expression tri(C a -Cb alkyl)silyl in the present specification, and they are selected in the respective specified carbon atom number range.
  • R 3 and R 4 can form a 3 to 7-membered ring by bonding together" in the present specification, for example cyclopropane, cyclobutane, cyclopentane, cyclohexane and the like are mentioned, and they are selected in the respective specified atom number range.
  • R 6 together with R 7 , by forming a C 2 -C 6 alkylene chain, can form a 3 to 7-membered ring together with the linking carbon atom, and in this case this alkylene chain may contain 1 oxygen atom, sulphur atom or nitrogen atom" in the present specification, for example aziridine, azetidine, azetidin-2-one, pyrrolidine, pyrrolidin-2-one, oxazolidine, oxazolidin-2-one, thiazolidine, thiazolidin-2-one,
  • imidazolidine, imidazolidin-2-one, piperidine, piperidin-2-one, morpholine, tetrahydro-1,3- oxazin-2-one, thio morpholine, tetrahydro-l,3-thiazin-2-one, piperazine, tetrahydropyrimidin- 2-one, homopiperidine, homopiperidin-2-one and the like are mentioned, and they are selected in the respective specified atom number range.
  • Expressions such as (C a -Cb) alkyl optionally substituted with R 10 in the present specification indicate an alkyl group wherein hydrogen atoms bonded to the carbon atoms can be optionally replaced by any R 10 and wherein made up of a number of carbon atoms a to b has the aforesaid meaning and they are selected in the respective specified carbon atom number range.
  • the respective R 10 can be the same or different.
  • Expressions such as (C a -C b ) cycloalkyl optionally substituted with R 10 in the present specification indicate a cycloalkyl group wherein hydrogen atoms bonded to the carbon atoms can be optionally replaced by any R 10 and wherein made up of a number of carbon atoms a to b has the aforesaid meaning and they are selected in the respective specified carbon atom number range.
  • the respective R 10 can be the same or different.
  • Expressions such as (C a -Cb) alkenyl optionally substituted with R 10 in the present specification indicate an alkenyl group wherein hydrogen atoms bonded to the carbon atoms can be optionally replaced by any R 10 and wherein made up of a number of carbon atoms a to b has the aforesaid meaning and they are selected in the respective specified carbon atom number range. In this case, when 2 or more substituents R 10 are present on the respective (C a -Cb) alkenyl optionally substituted with R 10 in the present specification indicate an alkenyl group wherein hydrogen atoms bonded to the carbon atoms can be optionally replaced by any R 10 and wherein made up of a number of carbon atoms a to b has the aforesaid meaning and they are selected in the respective specified carbon atom number range. In this case, when 2 or more substituents R 10 are present on the respective (C a -
  • Expressions such as (C a -Cb) alkynyl optionally substituted with R 10 in the present specification indicate an alkynyl group wherein hydrogen atoms bonded to the carbon atoms can be optionally replaced by any R 10 and wherein made up of a number of carbon atoms a to b has the aforesaid meaning and they are selected in the respective specified carbon atom number range.
  • the respective R 10 can be the same or different.
  • haloalkylsulphonamide derivatives represented by the formula (1) can for example be produced by reacting a compound represented by the formula (2) and a compound represented by the formula (3).
  • the compounds of the present invention represented by the formula (1) can be produced by reacting a compound represented by the formula (2) [in the formula, W, X , R 1 , R , R , R , R , R , R , R , m, n and p have the same meanings as aforesaid] or salts thereof and a compound represented by the formula (3) [in the formula, R 5 has the same meanings as aforesaid] or salts thereof in a solvent or with no solvent, using a base if necessary, and adding additives if necessary.
  • a compound represented by the formula (3) in the range from 0.1 to 100 equivalents of the compound represented by the formula (3) can be used per equivalent of the compound represented by the formula (2) ⁇
  • the solvent used is preferably inert in the reaction and for example polar solvents such as N,N-dimethylformamide, ⁇ , ⁇ -dimethylacetamide, acetonitrile, dimethyl sulphoxide, l,3-dimethyl-2-imidazolinone and water, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxan, 1 ,2-dimethoxyethane and diphenyl ether, alcohols such as ethanol and methanol, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride and 1 ,2-dichloroethane, and aliphatic hydrocarbons such as n-pentane and n-hexane are mentioned.
  • polar solvents such as N,N-dimethylformamide, ⁇ , ⁇ -dimethylace
  • a base as the base used, an organic base such as triethylamine, pyridine and 4-(dimethylamino)pyridine or an inorganic base such as potassium carbonate, sodium carbonate, potassium acetate and sodium acetate can be used, and can be used in the range from 0.1 to 50 equivalents per equivalent of the compound represented by the formula (2).
  • an organic base such as triethylamine, pyridine and 4-(dimethylamino)pyridine
  • an inorganic base such as potassium carbonate, sodium carbonate, potassium acetate and sodium acetate
  • ethers such as 1,4,7, 10,13, 16-hexaoxa- cyclooctadecane, quaternary ammonium salts such as tetra-n-butylammonium bromide and the like can be used, and can be used in the range from 0.1 to 50 equivalents per equivalent of the compound represented by the formula (2).
  • reaction temperature any temperature in the range from -78°C to the reflux temperature of the reaction mixture can be set, and the reaction time varies depending on the concentration of the reactants and the reaction temperature, but can normally be set anywhere in the range from 5 mins to 100 hrs.
  • the haloalkylsulphonamide derivatives represented by the formula (1) can for example be produced by reacting a compound represented by the formula (4) and a compound represented by the formula (5).
  • the compounds of the present invention represented by the formula (1) can be produced by reacting a compound represented by the formula (4) [in the formula, W, X , R 1 , R , R , R , R , R , R , R , m, n and p have the same meanings as aforesaid] which can be produced according to the method described in production method A or salts thereof and a compound represented by the formula (5) [in the formula, R 5 has the same meaning as aforesaid, and L represents a leaving group such as a halogen atom] or salts thereof in a solvent or with no solvent, using a base if necessary, and adding additives if necessary.
  • the solvent used is preferably inert in the reaction and for example polar solvents such as N,N-dimethylformamide, ⁇ , ⁇ -dimethylacetamide, acetonitrile, dimethyl sulphoxide, l,3-dimethyl-2-imidazolinone and water, ethers such as diethyl ether, tetrahydrofuran, 1 ,4-dioxan, 1 ,2-dimethoxyethane and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride and 1 ,2-dichloroethane, and aliphatic hydrocarbons such as n-pentane and n-hexane are mentioned.
  • polar solvents such as N,N-dimethylformamide, ⁇ , ⁇ -dimethylacetamide, acetonitrile
  • a base as the base used, an organic base such as triethylamine, pyridine or 4- (dimethylamino)pyridine or an inorganic base such as potassium carbonate, sodium carbonate or sodium hydrogen carbonate can be used, and from 0.1 to 50 equivalents can be used per equivalent of the compound represented by the formula (4).
  • an organic base such as triethylamine, pyridine or 4- (dimethylamino)pyridine
  • an inorganic base such as potassium carbonate, sodium carbonate or sodium hydrogen carbonate
  • ethers such as 1,4,7, 10,13, 16-hexaoxa- cyclooctadecane, quaternary ammonium salts such as tetra-n-butylammonium bromide and the like can be used, and from 0.1 to 50 equivalents can be used per equivalent of the compound represented by the formula (4).
  • reaction temperature any temperature in the range from -78°C to the reflux temperature of the reaction mixture can be set, and the reaction time varies depending on the concentration of the reactants and the reaction temperature, but can normally be set anywhere in the range from 5 mins to 100 hrs.
  • the compounds of the present invention can be obtained by performing normal postprocessing, in that the reaction mixture after the end of the reaction is concentrated directly or extracted with an organic solvent and concentrated after washing with water, or poured into ice-water and concentrated after organic solvent extraction. Further, when purification is necessary, they can be isolated and purified by any purification method such as recrystallization, column chromatography, thin layer chromatography or liquid chromatography fractionation.
  • brominating agent used for example, quaternary ammonium salts such as phenyl trimethylammonium bromide or phenyl trimethylammonium tribromide and the like are mentioned.
  • the solvent used is preferably inert in the reaction and for example polar solvents such as N,N-dimethylformamide, ⁇ , ⁇ -dimethylacetamide, acetonitrile, dimethyl sulphoxide and l,3-dimethyl-2-imidazolinone, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxan, 1 ,2-dimethoxyethane and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride and 1,2-dichloroethane, and aliphatic solvents such as N,N-dimethylformamide, ⁇ , ⁇ -dimethylacetamide, acetonitrile, dimethyl sulphoxide and l,3-dimethyl-2-imidazolinone, ethers such as dieth
  • hydrocarbons such as n-pentane and n-hexane are mentioned. These solvents can be used alone, and 2 or more of these can also be used mixed.
  • organic bases such as triethylamine, pyridine, 4- (dimethylamino)pyridine and diisopropylethylamine, or inorganic bases such as potassium carbonate and sodium carbonate can be used, and from 0.1 to 50 equivalents can be used per equivalent of compound represented by the formula (6).
  • silylating agents such as trimethylsilyl trifluoromethanesulphonate can be used, and from 0.1 to 50 equivalents can be used per equivalent of compound represented by the formula (6).
  • reaction temperature any temperature in the range from -78°C to the reflux temperature of the reaction mixture can be set, and the reaction time varies depending on the concentration of the reactants and the reaction temperature, but can normally be set anywhere in the range from 5 mins to 100 hrs.
  • the compounds represented by the formula (7) can be obtained by performing normal postprocessing, in that the reaction mixture after the end of the reaction is concentrated directly or extracted with an organic solvent and concentrated after washing with water, or poured into ice-water and concentrated after organic solvent extraction. Further, when purification is necessary, they can be isolated and purified by any purification method such as recrystallization, column chromatography, thin layer chromatography or liquid chromatography fractionation.
  • the compounds represented by the formula (7) produced by this method can be used as such in the reaction of the next stage without isolation or purification.
  • Some compounds represented by the formula (6) are known compounds, and can be produced by known methods. For example, they can be produced according to the methods described in International Laid-Open Specification No. 2010/026989 and International Laid- Open Specification No. 2013/061973.
  • the solvent used is preferably inert in the reaction and for example polar solvents such as N,N-dimethylformamide, ⁇ , ⁇ -dimethylacetamide, acetonitrile, dimethyl sulphoxide, l,3-dimethyl-2-imidazolinone and water, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride and 1 ,2-dichloroethane, and aliphatic hydrocarbons such as n-pentane and n-hexane are mentioned.
  • polar solvents such as N,N-dimethylformamide, ⁇ , ⁇ -dimethylacetamide, acetonitrile, dimethyl sulphoxide, l,3-dimethyl-2-imidazolinone and water
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • ethers such as 1,4,7, 10,13, 16-hexaoxa- cyclooctadecane, quaternary ammonium salts such as tetra-n-butylammonium bromide and the like can be used, and from 0.1 to 50 equivalents can be used per equivalent of compound represented by the formula (7).
  • reaction temperature any temperature in the range from -78°C to the reflux temperature of the reaction mixture can be set, and the reaction time varies depending on the concentration of the reactants and the reaction temperature, but can normally be set anywhere in the range from 5 mins to 100 hrs.
  • the compounds represented by the formula (9) can be obtained by performing normal postprocessing, in that the reaction mixture after the end of the reaction is concentrated directly or extracted with an organic solvent and concentrated after washing with water, or poured into ice-water and concentrated after organic solvent extraction. Further, when purification is necessary, they can be isolated and purified by any purification method such as recrystallization, column chromatography, thin layer chromatography or liquid chromatography fractionation. Further, the compounds represented by the formula (9) produced by this method can be used as such in the reaction of the next stage without isolation or purification.
  • the compounds represented by the formula (10) [in the formula, W, X , R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 8 , R 9 , m, n and p have the same meanings as aforesaid] can be produced by reacting a compound represented by the formula (9) or salts thereof and a base in a solvent or with no solvent.
  • organic bases such as triethylamine, pyridine and 4-(dimethylamino)- pyridine
  • inorganic bases such as potassium carbonate, sodium carbonate, potassium hydroxide and sodium hydroxide and the like are mentioned.
  • the solvent used is preferably inert in the reaction and for example polar solvents such as N,N-dimethylformamide, ⁇ , ⁇ -dimethylacetamide, acetonitrile, dimethyl sulphoxide, l,3-dimethyl-2-imidazolinone and water, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxan, 1 ,2-dimethoxy ethane and diphenyl ether, alcohols such as ethanol and methanol, aromatic hydrocarbons such as benzene, toluene and xylene, and aliphatic hydrocarbons such as n-pentane and n-hexane are mentioned.
  • polar solvents such as N,N-dimethylformamide, ⁇ , ⁇ -dimethylacetamide, acetonitrile, dimethyl sulphoxide, l,3-dimethyl-2-imidazolinone and water
  • reaction temperature any temperature in the range from -78°C to the reflux temperature of the reaction mixture can be set, and the reaction time varies depending on the concentration of the reactants and the reaction temperature, but can normally be set anywhere in the range from 5 mins to 100 hrs.
  • the compounds of the formula (10) can be obtained by performing normal
  • reaction mixture after the end of the reaction is concentrated directly or extracted with an organic solvent and concentrated after washing with water, or poured into ice-water and concentrated after organic solvent extraction.
  • purification when purification is necessary, they can be isolated and purified by any purification method such as recrystallization, column chromatography, thin layer chromatography or liquid
  • the compounds represented by the formula (10) produced by this method can be used as such in the reaction of the next stage without isolation or purification.
  • the compound represented by the formula (2) can be produced by reacting a compound represented by the formula (10) or salts thereof and an oxidizing agent in a solvent or with no solvent, and by adding additives if necessary. In this reaction, from 0.1 to 100 equivalents of oxidizing agent can be used per equivalent of compound represented by the formula (10).
  • chromic acid salts such as pyridinium chlorochromate and pyridinium dichromate
  • manganese compounds such as potassium permanganate and manganese dioxide
  • hypervalent iodine compounds such as 1,1,1- triacetoxy-l,l-dihydro-l,2-benzoiodoxol-3-(lH)-one (Dess-Martin periodinane)
  • radical compounds such as the 2,2,6,6-tetramethylpiperidin-l-oxy radical and the like are mentioned.
  • the solvent used is preferably inert in the reaction and for example polar solvents such as N,N-dimethylformamide, ⁇ , ⁇ -dimethylacetamide, acetonitrile, dimethyl sulphoxide, l,3-dimethyl-2-imidazolinone and water, ethers such as diethyl ether, tetrahydrofuran, 1 ,4-dioxan, 1 ,2-dimethoxyethane and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride and 1 ,2-dichloroethane, and aliphatic hydrocarbons such as n-pentane and n-hexane are mentioned.
  • polar solvents such as N,N-dimethylformamide, ⁇ , ⁇ -dimethylacetamide, acetonitrile
  • ethers such as 1,4,7, 10,13, 16-hexaoxa- cyclooctadecane, quaternary ammonium salts such as tetra-n-butylammonium bromide and the like can be used, and from 0.1 to 50 equivalents can be used per equivalent of compound represented by the formula (10).
  • reaction temperature any temperature in the range from -78°C to the reflux temperature of the reaction mixture can be set, and the reaction time varies depending on the concentration of the reactants and the reaction temperature, but can normally be set anywhere in the range from 5 mins to 100 hrs.
  • the production intermediates used as starting materials in production method A can be obtained by performing normal postprocessing, in that the reaction mixtures after the end of the reactions are concentrated directly or extracted with an organic solvent and concentrated after washing with water, or poured into ice- water and concentrated after organic solvent extraction. Further, when purification is necessary, they can be isolated and purified by any purification method such as recrystallization, column chromatography, thin layer
  • production intermediates produced by this method can be used as such in the reaction of the next stage without isolation or purification.
  • U represents the structures shown by U-l [in the formula, R 2 have the same meanings as aforesaid] or U-2 [in the formula, R 2 have the same meanings as aforesaid].
  • substituents represented by D-7a in the table have the following structures.
  • the compounds of the present invention can be used both for flooded soil treatment methods and for foliage treatment methods.
  • paddy field weeds for example, Potamogetonaceae weeds typified for example by Potamogeton distinctus,
  • Alismataceae weeds typified for example by Alisma canaliculatum, Sagittaria pygmaea and Sagittaria trifolia, Gramineae weeds typified for example by Leptochloa chinensis,
  • Pontederiaceae weeds typified for example by Monochoria korsakowii and Monochoria vaginalis
  • Elatinaceae weeds typified for example by Elatine triandra
  • Lythraceae weeds typified for example by Ammannia multifiora and Rotala indica
  • Oenotheraceae weeds typified for example by Lidwigia epilobioides
  • Scrophulariaceae weeds typified for example by Dop atrium junceum, Gratiola japonica, Limonphila sessilifolia, Lindernia pyxidaria and Lindernia dubia
  • Leguminosae weeds typified for example by Aeschynomene indica
  • Compositae weeds such as Bidens frondosa and Bidens tripartita weeds and the like are mentioned.
  • the compounds of the present invention can also be used as field and orchard herbicides, and can be used in soil treatment, soil incorporation treatment and foliage treatment methods.
  • field weeds for example, Solanaceae weeds typified for example by Solanum nigrum and Datura stramonium, Geraniaceae weeds typified for example by Granium carolinianum, Malvaceae weeds typified for example by Abutilon theophrasti and Sida spinosa, Convolvulaceae weeds typified for example by Ipomoea spps.
  • Ipomoea purpurea such as Ipomoea purpurea, Ipomoea hederacea and Calystegia spps.
  • Amaranthaceae weeds typified for example by Amaranthus lividus and Amarnathus retroflexus
  • Compositae weeds typified for example by Xanthium pensylvanicum, Xanthium strumarium, Ambrosia artemisiae folia, Helianthus annuus, Galinsoga ciliate, Circium arvense, Senecio vulgaris and Erigeron annus
  • Cruciferae weeds typified for example by Rorippa indica, Sinapis arvensis and Capsella Bursapastoris
  • Polygonaceae weeds typified for example by Polygonum Blumei and
  • Polygonum convolvulus Portulacaceae weeds typified for example by Portulaca oleracea, Chenopodiaceae weeds typified for example by Chenopodium album, Chenopodium ficifolium and Kochia scoparia, Caryophyllaceae weeds typified for example by Stellaria media, Scrophulariaceae weeds typified for example by Veronica persica, Commelinaceae weeds typified for example by Commelina communis, Labiatae weeds typified for example by Lamium amplexicaule and Lamium purpureum, Euphorbiaceae weeds typified for example by Euphorbia supina, Euphorbia heterophylla and Euphorbia maculata, Rubiaceae weeds typified for example by Galium spurium, Gallium aparine and Rubia akane, Violaceae weeds typified for example by Viola mandshurica, and broad-leave
  • the compounds of the present invention can also be used in soil treatment, soil incorporation treatment and foliage treatment methods on non-agricultural land, for example on lawns, sports grounds, waste land, road verges and railway verges.
  • weeds in addition to those mentioned under field and orchard weed killers, Poa annua, Taraxacum officinale, Conyza sumatrensis, Cardamine flexuosa, Trifolium repens, Hydrocotyle sibthorpioides, Plantago asiatica, Cyperus brevifolius/Kyllinga brevifolia, Equisetum arvense and the like are mentioned.
  • herbicide as used herein means a compound that controls or modifies the growth of plants.
  • herbicidally effective amount means the quantity of such a compound or combination of such compounds that is capable of producing a controlling or modifying effect on the growth of plants. Controlling or modifying effects include all deviation from natural development, for example: killing, retardation, leaf burn, albinism, dwarfing and the like.
  • plants refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.
  • locus is intended to include soil, seeds, and seedlings, as well as established vegetation and includes not only areas where weeds may already be growing, but also areas where weeds have yet to emerge, and also to areas under cultivation with respect to crops of useful plants.
  • “Areas under cultivation” include land on which the crop plants are already growing and land intended for cultivation with such crop plants.
  • weeds as used herein means any undesired plant, and thus includes not only agronomically important weeds as described below, but also volunteer crop plants.
  • the compounds of the invention can be applied before or after planting of the crops, before weeds emerge (pre-emergence application) or after weeds emerge (post-emergence application), and are particularly effective when applied pre-emergence.
  • Crops of useful plants in which the composition according to the invention can be used include, but are not limited to, perennial crops, such as citrus fruit, grapevines, nuts, oil palms, olives, pome fruit, stone fruit and rubber, and annual arable crops, such as cereals, for example barley and wheat, cotton, oilseed rape, maize, rice, soy beans, sugar beet, sugar cane, sunflowers, ornamentals, switchgrass, turf and vegetables, especially cereals, maize, rice and soy beans.
  • Crops are to be understood as also including those crops which have been rendered tolerant to herbicides or classes of herbicides (e.g. auxins or ALS-, EPSPS-, PPO- and HPPD-inhibitors) by conventional methods of breeding or by genetic engineering.
  • herbicides or classes of herbicides e.g. auxins or ALS-, EPSPS-, PPO- and HPPD-inhibitors
  • An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding is Clearfield® summer rape (canola).
  • crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® and LibertyLink®, respectively.
  • Crops are also to be understood as being those which have been rendered resistant to harmful insects by genetic engineering methods, for example Bt maize (resistant to European corn borer), Bt cotton (resistant to cotton boll weevil) and also Bt potatoes (resistant to Colorado beetle).
  • Bt maize are the Bt 176 maize hybrids of NK® (Syngenta Seeds).
  • the Bt toxin is a protein that is formed naturally by Bacillus thuringiensis soil bacteria.
  • Examples of toxins, or transgenic plants able to synthesize such toxins are described in EP-A-451 878, EP-A-374 753, WO 93/07278, WO 95/34656, WO 03/052073 and EP-A-427 529.
  • transgenic plants comprising one or more genes that code for an insecticidal resistance and express one or more toxins are KnockOut® (maize), Yield Gard® (maize), NuCOTIN33B® (cotton), Bollgard® (cotton), NewLeaf® (potatoes), NatureGard® and Protexcta®.
  • Plant crops or seed material thereof can be both resistant to herbicides and, at the same time, resistant to insect feeding ("stacked" transgenic events).
  • seed can have the ability to express an insecticidal Cry3 protein while at the same time being tolerant to glyphosate.
  • Crops are also to be understood as being those which are obtained by conventional methods of breeding or genetic engineering and contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavor). Any method of application to weeds/crop of useful plant, or locus thereof, which is routinely used in agriculture may be used, for example application by spray or broadcast method typically after suitable dilution of a compound of formula (1) (whether said compound is formulated and/or in combination with one or more further active ingredients and/or safeners, as described herein). At the time of formulation or spraying, the compounds of the present invention can also as necessary be used mixed with other types of herbicide, various insecticides, bactericides, plant growth regulators or synergists and the like.
  • mixtures of compounds of formula (1) with other herbicides include (wherein "1" represents a compound of formula (1)): 1 + 2,4-D (including the choline salt and 2-ethylhexyl ester thereof), 1 + acetochlor, 1 + acifiuorfen-sodium, 1 + aclonifen, 1 + alachlor, 1 + alloxydim, 1 + alloxydim sodium, 1 + ametryn, 1 +
  • amicarbazone 1 + amidosulfuron, 1 + aminocyclopyrachlor, 1 + aminocyclopyrachlor salts and esters, 1 + aminopyralid, 1 + aminopyralid salts and esters, 1 + amiprophos-methyl, 1 + amitrol, 1 + anilofos, 1 + asulam, 1 + atrazine, 1 + azafenidin, 1 + azimsulfuron, 1 + beflubutamid, 1 + benazolin ethyl, 1 + bencarbazone, 1 + benfluralin/benefin, 1 +
  • ethametsulfuron methyl 1 + ethofumesate, 1 + etobenzanid, 1 + ethoxysulfuron, 1 + flazasulfuron, 1 + fenoxaprop, 1 + fenoxaprop-ethyl, 1 + fenoxasulfone, 1 + fenquinotrione, 1 + fentrazamide, 1 + flamprop, 1 + flazasulfuron, 1 + florasulam, 1 + fluazifop, 1 + fluazifop butyl, 1 + fluazolate, 1 + flucarbazone sodium, 1 + flucetosulfuron, 1 + flucloralm, 1 + flufenacet, 1 + flufenpyl ethyl, 1 + fiumetralin, 1 + flumetsulam, 1 + flumiclorac-pentyl, 1 + flumioxazin, 1 + fluometuron, 1 + fluorogly
  • pyribenzoxim 1 + pyributicarb, 1 + pyridafol, 1 + pyridate, 1 + pyriftalid, 1 + pyriminobac methyl, 1 + pyrimisulfan, 1 + pyrithiobac sodium, 1 + pyroxasulfone, 1 + pyroxsulam, 1 + quinclorac, 1 + quinmerac, 1 + quinoclamine, 1 + quizalofop, 1 + quizalofop ethyl, 1 + quizalofop tefuryl, 1 + quizalofop-P, 1 + quizalofop-P ethyl, 1 + quizalofop-P tefuryl, 1 + rimsulfuron, 1 + saflufenacil, 1 + sethoxydim, 1 + siduron, 1 + simazine, 1 + simetryn, 1 + sulcotrione, 1 + sulfen
  • cyclopyrimorate 1 + SW-065 (test name), 1 + TCBA (2,3,6-TBA ), 1 + TCBA salts and esters (2,3,6-TBA salts and esters), 1 + TCTP (chlorthal-dimethyl, tetorachlorothiophene) , 1 + tebutam, 1 + tebuthiuron, 1 + tefuryltrione, 1 + tembotrione, 1 + tepraloxydim, 1 + terbacil, 1 + terbumeton, 1 + terbuthylazine, 1 + terbutryn, 1 + tetrapion (flupropanate), thenylchlor, 1 + thiazafluron, 1 + thiazopyr, 1 + thidiazimin, 1 + thidiazuron, 1 + thiencarbazone methyl, 1 + thifensulfuron methyl, 1 + tiafenacil, 1 + to
  • a compound of the formula (1) with a triazine (e.g. 1 + ametryn, 1 + atrazine, 1 + cyanazine, 1 + dimethametryn, 1 + metribuzin, 1 + prometon, 1 + prometryn, 1 + propazine, 1 + simazine, 1 + simetryn, 1 + terbumeton, 1 + terbuthylazine, 1 + terbutryn, 1 + trietazine).
  • a triazine e.g. 1 + ametryn, 1 + atrazine, 1 + cyanazine, 1 + dimethametryn, 1 + metribuzin, 1 + prometon, 1 + prometryn, 1 + propazine, 1 + simazine, 1 + simetryn, 1 + terbumeton, 1 + terbuthylazine, 1 + terbutryn, 1 + trietazine.
  • HPPD inhibitor e.g. 1 + isoxaflutole, 1 + mesotrione, 1 + pyrasulfotole, 1 + sulcotrione, 1 + tembotrione, 1 + topramezone, 1 + bicyclopyrone, 1 + benzobicyclon or 1 + 2-[[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3- oxo-2-quinoxalinyl]carbonyl] l,3-cyclohexanedione (CAS R 1342891-70-6)).
  • HPPD inhibitor e.g. 1 + isoxaflutole, 1 + mesotrione, 1 + pyrasulfotole, 1 + sulcotrione, 1 + tembotrione, 1 + topramezone, 1 + bicyclopyrone, 1 + benzobicyclon or 1 + 2-[[8-chloro-3,4-dihydro-4-(4-meth
  • auxin e.g. 1 + dicamba, 1 + 2,4-D, 1 + 2,4-DB, 1 + MCPA, 1 + fluroxypyr, 1 + picloram, 1 + triclopyr, 1 + quinclorac, 1 + clopyralid, 1 + aminopyralid, 1 + aminocyclopyrachlor, 1 + halauxifen, 1 + halauxifen- methyl).
  • auxin e.g. 1 + dicamba, 1 + 2,4-D, 1 + 2,4-DB, 1 + MCPA, 1 + fluroxypyr, 1 + picloram, 1 + triclopyr, 1 + quinclorac, 1 + clopyralid, 1 + aminopyralid, 1 + aminocyclopyrachlor, 1 + halauxifen, 1 + halauxifen- methyl).
  • metolachlor 1 + S-metolachlor, 1 + acetochlor, 1 + dimethenamid-P, 1 + pyroxasulfone, 1 + dimethachlor, 1 + flufenacet, 1 + metazachlor, 1 + napropamide, 1 + pretilachlor).
  • a triazolinone e.g.1 + amicarbazone.
  • a PPO inhibitor e.g. 1 + fomesafen, 1 + flumioxazin, 1 + sulfentrazone, 1 + acifluorfen-sodium, 1 + lactofen, 1 + oxyfluorfen, 1 + oxadiazon, 1 + butafenacil, 1 + carfentrazone-ethyl, 1 + [3-[2-chloro-4-fluoro-5-(l-methyl-6- trifluoromethyl-2,4-dioxo-l,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetic acid ethyl ester).
  • a PPO inhibitor e.g. 1 + fomesafen, 1 + flumioxazin, 1 + sulfentrazone, 1 + acifluorfen-sodium, 1 + lactofen, 1 + oxyfluorfen, 1 + oxadiazon, 1 +
  • the following mixtures are also preferred: 1 + glyphosate, 1 + glufosinate, 1 + paraquat, 1 + diquat, 1 + pendimethalin, 1 + trifluralin, 1 + metamitron, 1 + clomazone, 1 + prodiamine, 1 + saflufenacil, 1 + prosulfocarb, 1 + diflufenican, 1 + isoxaben, 1 + beflubutamide, 1 + flurtamone, 1 + benfluralin, 1 + chlorotoluron, 1 + linuron, 1 + isoproturon, 1 + triallate, 1 + hexazinone, 1 + diuron, 1 + propanil, 1 + indaziflam.
  • the following mixtures are preferred: 1 + ametryn, 1 + atrazine, 1 + cyanazine, 1 + dimethametryn, 1 + metribuzin, 1 + prometon, 1 + prometryn, 1 + propazine, 1 + simazine, 1 + simetryn, 1 + terbumeton, 1 + terbuthylazine, 1 + terbutryn, 1 + trietazine, 1 + isoxaflutole, 1 + mesotrione, 1 + pyrasulfotole, 1 + sulcotrione, 1 +
  • aminocyclopyrachlor 1 + halauxifen, 1 + halauxifen-methyl, 1 + metolachlor, 1 + S- metolachlor, 1 + acetochlor, 1 + dimethenamid-P, 1 + pyroxasulfone, 1 + dimethachlor, 1 + flufenacet, 1 + metazachlor, 1 + napropamide, 1 + pretilachlor, 1 + amicarbazone, 1 + chlorsulfuron, 1 + cinosulfuron, 1 + cloransulam, 1 + ethametsulfuron, 1 + flazasulfuron, 1 + foramsulfuron, 1 + flumetsulam, 1 + imazamethabenz, 1 + imazamox, 1 + imazapic, 1 + imazapyr, 1 + imazethapyr, 1 + iodosulfuron, 1 + iofensulfuron, 1 + metsulfuron, 1 + nicos
  • the following mixtures are particularly preferred: 1 + atrazine, 1 + terbuthylazine, 1 + isoxaflutole, 1 + mesotrione, 1 + S-metolachlor, 1 + acetochlor, 1 + pyroxasulfone, 1 + dimethachlor, 1 + flufenacet, 1 + nicosulfuron, 1 + fomesafen, 1 + glyphosate, 1 + glufosinate, 1 + paraquat, 1 + saflufenacil, 1 + prosulfocarb.
  • the present invention also includes three-way mixtures of a compound of formula (1), a herbicide as defined above and a further herbicide.
  • the following three-way mixtures are preferred: 1 + atrazine + mesotrione, 1 + atrazine + S-metolachlor, 1 + S-metolachlor + mesotrione, 1 + glyphosate + mesotrione, 1 + glufosinate + mesotrione, 1 + atrazine + isoxaflutole, 1 + S-metolachlor + isoxaflutole, 1 + glyphosate + isoxaflutole, 1 + glufosinate + isoxaflutole, 1 + glyphosate + fomesafen.
  • the present invention also includes four- way mixtures of a compound of formula (1), a herbicide as defined above and two further herbicides.
  • the following four-way mixture is preferred: 1 + atrazine + mesotrione + S-metolachlor.
  • the mixing partners of the compound of formula (1) may also be in the form of esters or salts, as mentioned e.g. in The Pesticide Manual, 14th Edition (BCPC), 2006.
  • BCPC The Pesticide Manual, 14th Edition
  • the reference to acifluorfen-sodium also applies to acifluorfen
  • the reference to dimethenamid also applies to dimethenamid-P
  • the reference to glufosinate-ammonium also applies to glufosinate
  • the reference to bensulfuron-methyl also applies to bensulfuron
  • the reference to cloransulam-methyl also applies to cloransulam
  • the reference to flamprop-M also applies to flamprop
  • the reference to pyrithiobac-sodium also applies to pyrithiobac, etc.
  • the mixing ratio of the compound of formula (1) to the mixing partner is preferably from 1 : 100 to 1000: 1.
  • Compounds of formula (1) may also be combined with herbicide safeners.
  • herbicide safeners are preferred, for example, (wherein "1" represents a compound of formula (1)) 1+ AD-67, benoxacor , 1 + cloquintocet-mexyl , 1 + cyomerinil , 1 + dichlormid , 1 + dicyclonone , 1 + cyprosulfamide , 1 + diethorate , 1 + DKA-24, dymron , 1 + fenclorazole ethyl , 1 + fenclorim , 1 + HEXIM , 1 + flurazole , 1 + fluxofenim , 1 + furilazole , 1 + isoxadifen , 1 + isoxadifen ethyl , 1 + MCPA, 1 + mecoprop , 1 + mefenpyr , 1 + mefenpyr ethyl , 1 + mefen
  • the following compound/safener combinations are preferred: 1 + cloquintocet-mexyl, 1 + cyprosulfamide, 1 + N-(2-methoxybenzoyl)-4- [(methylaminocarbonyl)amino]benzenesulfonamide, 1 + isoxadifen-ethyl, 1 + benoxacor, 1 + dichlormid and 1 + fluxofenim .
  • the safeners of the compound of formula (1) may also be in the form of esters or salts, as mentioned e.g. in The Pesticide Manual, 14th Edition (BCPC), 2006.
  • BCPC Pesticide Manual, 14th Edition
  • the reference to cloquintocet-mexyl also applies to cloquintocet and to a lithium, sodium, potassium, calcium, magnesium, aluminium, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salt thereof as disclosed in WO02/34048 and the reference to fenchlorazole-ethyl also applies to fenchlorazole, etc.
  • the mixing ratio of compound of formula (1) to safener is from 100: 1 to 1 : 10, especially from 20: 1 to 1 : 1.
  • active ingredient relates to the respective mixture of compound of formula (1) and any further active ingredient, in particular a further herbicide, with the safener).
  • the safener and a compound of formula (1) and one or more additional herbicide(s), if any, are applied simultaneously.
  • the safener, a compound of formula (1) and one or more additional herbicide(s), if any might be applied to the locus pre-emergence or might be applied to the crop post-emergence.
  • the safener and a compound of formula (1) and one or more additional herbicide(s), if any are applied sequentially.
  • the safener might be applied before sowing the seeds as a seed treatment and a compound of formula (1) and one or more additional herbicides, if any, might be applied to the locus pre-emergence or might be applied to the crop post-emergence.
  • the compounds of the present invention are used as herbicides, they are usually mixed with a suitable solid carrier or liquid carrier, and moreover surfactants, penetrants, spreading agents, thickeners, antifreeze agents, binders, anticaking agents, disintegrants, stabilizing agents and the like are added as desired, and they can be put to use in
  • formulations of any type such as wettable powders, emulsions, flowables, dry flowables, liquids, powders, granules or gels. Further, to save labour and increase safety, the aforesaid formulations of any type can be sealed into waterproof packages.
  • solid carriers for example natural mineral substances such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acidic clay, attapulgite, zeolite and diatomaceous earth, inorganic salts such as calcium carbonate, ammonium sulphate, sodium sulphate, potassium chloride, synthetic silicic acid and synthetic silicate salts are mentioned.
  • natural mineral substances such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acidic clay, attapulgite, zeolite and diatomaceous earth
  • inorganic salts such as calcium carbonate, ammonium sulphate, sodium sulphate, potassium chloride, synthetic silicic acid and synthetic silicate salts are mentioned.
  • liquid carriers for example alcohols such as ethylene glycol, propylene glycol and isopropanol, aromatic hydrocarbons such as xylene, alkylbenzenes and alkylnaphth-alenes, ethers such as butyl cellosolve, ketones such as cyclohexanone, esters such as ⁇ - butyrolactone, acid amides such as N-methylpyrrolidone and N-octylpyrrolidone, plant oils such as soya bean oil, rapeseed oil, cottonseed oil and castor oil, and water, are mentioned.
  • aromatic hydrocarbons such as xylene, alkylbenzenes and alkylnaphth-alenes
  • ethers such as butyl cellosolve
  • ketones such as cyclohexanone
  • esters such as ⁇ - butyrolactone
  • acid amides such as N-methylpyrrolidone and N-octyl
  • These solid and liquid carriers can be used alone or 2 or more can be used together.
  • nonionic surfactants such as polyoxy ethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene styryl phenyl ethers, polyoxyethylene polyoxypropylene block copolymers, polyoxyethylene fatty acid esters, sorbitan fatty acid esters and polyoxyethylene sorbitan fatty acid esters, anionic surfactants such as alkyl sulphate salts, alkylbenzenesulphonate salts, lignin-sulphonate salts, alkylsulphosuccinate salts, naphthalenesulphonate salts, alkylnaphthalenesulphonate salts, naphthalenesulphonic acid formalin condensate salts, alkylnaphthalenesulphonic acid formalin condensate salts, polyoxyethylene alkyl aryl ether sulphate and phosphate salts, polyoxyethylene styryl phen
  • these surfactants usually from 0.05 to 20 parts by weight per 100 parts by weight of the formulation of the present invention is preferable. Further, these surfactants can be used alone, or 2 or more can be used together. At the time of formulation or spraying, the compounds of the present invention can also as necessary be used mixed with other types of herbicide, various insecticides, bactericides, plant growth regulators or synergists and the like.
  • the dosage of the compounds of the present invention may differ depending on the use location, time of use, method of use, crop grown and the like, but in general from 0.005 to about 50 kg as active substance weight per hectare (ha) is suitable.
  • anticaking agents for example anticaking agents, stabilizing agents and the like are mentioned.
  • antidrift agents for example antidrift agents, stabilizing agents and the like are mentioned.
  • the aforesaid formlations are sprayed as such or after 1-10,000-fold dilution with water.
  • the above are made into a wettable powder by uniformly mixing and grinding.
  • Sorbol 2680 5 parts (Anionic surfactant: Toho Chemical Industries (Corp.) brand name)
  • Nonionic surfactant Kao (Corp.) brand name
  • a granule formulation is made by granulating in an extruding granulator and drying.
  • the proton nuclear magnetic resonance chemical shift values in the practical examples were measured at 300 MHz using Me4Si (tetramethylsilane) as the reference substance. Further, the solvents used for the measurements are stated in the following synthetic examples. Further, the symbols in the proton nuclear magnetic resonance chemical shift values in the practical examples have the following meanings. s: singlet, brs: broad singlet, d: doublet, t: triplet, q: quintet, m: multiplet.
  • Hydroxylamine hydrochloride (26 mg, 0.37 mmol) was added at room temperature to a mixed solution of l-[2-(N-ethoxycarbonyl-N- trifluoromethanesulphonyl)aminobenzyl]piperidin-2,3-dione (0.13 g, 0.31 mmol) and 3 ml ethanol. After the end of the addition, the said reaction mixture was stirred for 1 hr at room temperature. After the end of the reaction, the solvent in the said reaction liquid was distilled off under reduced pressure.
  • Trimethylsilyl trifluoromethanesulphonate (9.47 g, 42.6 mmol) was added with ice cooling to a mixed solution of l-[2-(N-ethoxycarbonyl-N-trifluoromethanesulphonyl)- aminobenzyl]piperidin-2-one (14.5 g, 35.5 mmol), triethylamine (5.37 g, 53.2 mmol) and 50 ml dichloromethane. After the end of the addition, the said reaction mixture was stirred for 1 hr with ice cooling. After the end of the stirring, phenyltrimethylammonium tribromide (20.0 g, 53.2 mmol) was added with ice cooling to the said reaction mixture.
  • Stage 4 Synthesis of l-[2-(N-ethoxycarbonyl-N-trifluoromethanesulphonyl)amino-benzyl]- 3 -hydroxypiperidin-2-one
  • Ethyl chloroformate (3.55 g, 32.7 mmol) was added at room temperature to a mixed solution of l-[2-(N-trifluoromethanesulphonyl)aminobenzyl]-3-hydroxypiperidin-2-one (7.68 g, 21.8 mmol), sodium hydrogen carbonate (2.75 g, 32.7 mmol) and 20 ml acetonitrile. After the end of the addition, the said reaction mixture was stirred for 3 hrs with heating under reflux.
  • Stage 5 Synthesis of l-[2-(N-ethoxycarbonyl-N-trifluoromethanesulphonyl)amino- benzyl]piperidin-2,3-dione l,l,l-triacetoxy-l,l-dihydro-l,2-benzoiodoxol-3-(lH)-one (0.31 g, 0.73 mmol) was added with ice cooling to a mixed solution of l-[2-(N-ethoxycarbonyl-N-trifluoro- methanesulphonyl)aminobenzyl]-3-hydroxypiperidin-2-one (0.26 g, 0.61 mmol) and 10 ml dichloromethane.
  • Examples of compounds of the present invention produced similarly to synthetic examples 1 to 3 are shown in tables 2 to 5, but the present invention is not limited only to these. It should be noted that the entry Me in the tables represents methyl group, and similarly below Et represents ethyl group, Pr propyl group, Bu butyl group, Ph phenyl group, n- normal and i- iso respectively.
  • the entry "m. p.” means "melting point”, and the entry means resinous state.
  • Sterilized alluvial soil was introduced into 21 cm wide, 13 cm deep, 7 cm high plastic boxes, seeds of barnyard grass, hairy fmgergrass, green foxtail, wild oat, short awn foxtail, Italian ryegrass, black-grass, Indian mallow, ragweed, blue cockscomb, white goosefoot, tufted knotweed, common chickweed, goosegrass, speedwell, maize, soya bean, rice, wheat and beet were sown at respective spots, and covered with ca. 1.5 cm of soil.
  • Sterilized alluvial soil was introduced into 21 cm wide, 13 cm deep, 7 cm high plastic boxes, seeds of barnyard grass, hairy fmgergrass, green foxtail, wild oat, short awn foxtail, Italian ryegrass, black-grass, Indian mallow, ragweed, blue cockscomb, white goosefoot, tufted knotweed, common chickweed, goosegrass, speedwell, maize, soya bean, rice, wheat and beet were sown at respective spots, and after covering with ca. 1.5 cm of soil, the plants were grown in a greenhouse at 25 to 30°C.
  • the dosage (g/a) reflects the fact that, when converting to the per are (la) basis, the concentrations were adjusted so that treatment was with the stated number of grams. Table 7 o.
  • Dosage (g/a) A B C a-01 2.52 4 5 5 1-02 2.52 5 5 5 0-03 2.52 5 5 5 0-04 2.52 5 5 5 0-05 2.52 5 5 5 2-06 2.52 5 5 5 0-07 2.52 5 5 5 5 0-08 2.52 5 5 5 5 0-09 2.52 5 5 0-10 2.52 5 5 5 0-11 2.52 5 5 5 0-12 2.52 5 5 5 5 0-13 2.52 5 5 5 5 1-14 2.52 5 5 5 5 0-15 2.52 5 4 4 0-16 2.52 5 5 5 1-17 2.52 5 5 5 0-18 2.52 4 5 5 1-19 2.52 5 5 5 0-20 2.52 5 5 5 5 0-21 2.52 5 5 5 0-22 2.52 5 5 5 0-23 2.52 5 5 5 1-24 2.52 5 5 5 0-25 2.5
  • haloalkylsulphonamide derivatives of the present invention are novel compounds and are useful as selective herbicides for rice, maize, soya bean, wheat/barley and rape.

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Abstract

La présente invention concerne des dérivés haloalkylsulphonamides de la formule (1): dans laquelle A représente un groupe -CH=CH- ou un atome de soufre, W représente un atome d'oxygène ou autre, R1 représente un groupe haloalkyle en C1-C6 , R2, R3 et R4 représentent chacun indépendamment des atomes d'hydrogène ou autre, R5 représente un atome d'hydrogène, un groupe alkyle en C1-C6 ou autre, R6, R7, R8 et R9 représentent chacun indépendamment des atomes d'hydrogène ou autre, X représente un atome d'halogène ou autre, m représente un nombre entier d'une valeur allant de 0 à 4, n représente un nombre entier d'une valeur allant de 1 à 4, et p représente un nombre entier d'une valeur allant de 0 à 1, ainsi que les herbicides les contenant et les procédés d'utilisation de ces composés pour réguler la croissance des plantes.
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Publication number Priority date Publication date Assignee Title
WO2016207082A1 (fr) * 2015-06-23 2016-12-29 Syngenta Participations Ag Composés haloalkylsulphonamide herbicides
WO2018135649A1 (fr) 2017-01-20 2018-07-26 北興化学工業株式会社 Dérivé d'isoxazolin-5-one et herbicide le contenant en tant que principe actif
WO2020022350A1 (fr) 2018-07-24 2020-01-30 北興化学工業株式会社 Dérivé d'isoxazolin-5-one, et herbicide le contenant en tant que principe actif
CN115073458A (zh) * 2022-07-04 2022-09-20 山东致泰医药技术有限公司 一种阿维巴坦钠的制备方法
CN115232113A (zh) * 2022-07-04 2022-10-25 山东致泰医药技术有限公司 5r-(((四氢-2h-吡喃-2-基)氧基)氨基)哌啶-2s-羧酸酯盐的制备方法
WO2023210623A1 (fr) * 2022-04-28 2023-11-02 株式会社エス・ディー・エス バイオテック Composé anilide haloalkylsulfoné et herbicide le contenant

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WO2023210623A1 (fr) * 2022-04-28 2023-11-02 株式会社エス・ディー・エス バイオテック Composé anilide haloalkylsulfoné et herbicide le contenant
CN115073458A (zh) * 2022-07-04 2022-09-20 山东致泰医药技术有限公司 一种阿维巴坦钠的制备方法
CN115232113A (zh) * 2022-07-04 2022-10-25 山东致泰医药技术有限公司 5r-(((四氢-2h-吡喃-2-基)氧基)氨基)哌啶-2s-羧酸酯盐的制备方法

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