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WO1998049150A1 - Derives de triazine, production de ces produits et composition agrochimique - Google Patents

Derives de triazine, production de ces produits et composition agrochimique Download PDF

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Publication number
WO1998049150A1
WO1998049150A1 PCT/JP1998/001872 JP9801872W WO9849150A1 WO 1998049150 A1 WO1998049150 A1 WO 1998049150A1 JP 9801872 W JP9801872 W JP 9801872W WO 9849150 A1 WO9849150 A1 WO 9849150A1
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group
substituted
optionally
compound
alkyl
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PCT/JP1998/001872
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English (en)
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Shigeyuki Itoh
Satoko Nakamura
Yasushi Tanaka
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Takeda Chemical Industries, Ltd.
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Priority to AU70802/98A priority Critical patent/AU7080298A/en
Priority to JP10159753A priority patent/JPH11302252A/ja
Publication of WO1998049150A1 publication Critical patent/WO1998049150A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/08—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/10—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Definitions

  • the present invention relates to a novel triazine derivative having excellent and selective herbicidal activity, a production method for the compound, and an agrochemical composition comprising the compound.
  • the triazine derivative of the invention is a novel compound having excellent herbicidal activity against paddy field and plow land weeds without inducing any material adverse responses in crop plants such as rice, wheat, barley, soybean, maize and other plants and finds application as a useful selective herbicide.
  • JP-A 241047/1988 discloses a rubber composition comprising a triazine derivative.
  • use as an agrochemical is not described.
  • JP-A 133968/1991 reports a tri-substituted 1, 3, 5-triazine-2 , 4,6-trione. Though use for a bactericide or a fungicide is described, use for a herbicide is not described.
  • JP-A 93539/1974, JP-A 47534/1974, WO91/01978, USP 3,505,323, USP 3,505,057 and JP-A 41542/1974 describe various triazine derivatives which can be used for an agrochemical or a herbicide.
  • a triazine derivative of the present invention is not disclosed in this literature in addition to (1) and (2) as mentioned above .
  • Q represents an aromatic ring group which may optionally be substituted
  • R represents a hydrogen atom or a hydrocarbon group which may optionally be substituted
  • R represents a hydrocarbon group which may optionally be substituted or R and R may form a ring together with the adjacent carbon atom wherein the ring may optionally be substituted, at the 1-position, and (ii) oxo group or thioxo group at the 2-position, and (iii) which may have a substituent at each 3- to 6-position, provided that said triazine derivative does not have oxo groups at both the 4- and 6-positions, or a salt thereof, has potent herbicidal activity with remarkably improved phytotoxic toward crop plants such as rice, wheat, barley, soybean, maize, and other plants, thus showing high specificity. They have made further research with diligence and have perfected the present invention.
  • the present invention relates to: [1] a partially hydrogenated or completely hydrogenated 1, 3 , 5-triazine derivative which has (i) a group of the formula: wherein Q represents an aromatic ring group which may optionally be substituted; R represents a hydrogen atom or a hydrocarbon group which may optionally be substituted; R represents a hydrocarbon group which may optionally be substituted or R 1 and R2 may form a ring together with the adjacent carbon atom wherein the ring may optionally be substituted, at the 1-position, and (ii) oxo group or thioxo group at the 2-position, and (iii) which may have a substituent at each 3- to 6-position, provided that said triazine derivative does not have oxo groups at both the 4- and 6-positions (hereinafter referred to as "compound (la)", or a salt thereof,
  • A represents an optionally substituted methylene group, carbonyl group or thiocarbonyl group
  • B represents an optionally
  • Q , R and R are the same or different and each represents a hydrogen atom or a group bonded through a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom; and W represents 0 or S,
  • a hydrocarbon group selected from the group consisting of a C ⁇ alkyl group, a C 3 _ 1 cycloalkyl group, a C 2 _ 6 alkenyl group, a C 3 _j .4 cycloalkenyl group, a C 2 _ 6 alkynyl group, a C 6 _ 14 aryl group and a C 7 .
  • lg aralkyl group when said hydrocarbon group is an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group or an alkynyl group, each of said groups may have one to three substituents selected from the group consisting of a C,.
  • alkylthio group halogen, a C,_ 6 alkoxy group, nitro, a C ⁇ g alkoxy-carbonyl group, a mono- or di-C j .g alkylamino group, a C 6 alkoxyimino group, hydroxyimino, a C ⁇ alkylsulfonyl group, cyano, carboxyl, hydroxy, a C,_ 6 alkylcarbonyloxy group, a C _ 7 alkanoyl group or a ⁇ _ 6 alkylimino group, and when said hydrocarbon group is an aryl group or an aralkyl group, each of said groups may have one to five substituents selected from the group consisting of (i) a Ci_ 6 alkyl group, (ii) a C 3 .
  • a 3- to 8-membered heterocyclic group or a condensed ring group thereof with benzene ring or a 3- to 8-membered heterocyclic ring which may optionally be substituted with one to three substituents selected from the group consisting of (i) a Cj_ 6 alkyl group, (ii) a C 3 . 6 cycloalkyl group, (iii) a C 2 . 6 alkenyl group, (iv) a C 2 _ 6 alkynyl group, (v) a ⁇ . 6 alkoxy group, (vi) an acyl group selected from the group consisting of a Ci_ 7 alkanoyl group, a C 6 .
  • an acyl group selected from the group consisting of a Ci. 7 alkanoyl group, a C 6 . aryl-carbonyl group, a C ⁇ _ 6 alkoxy-carbonyl group, a C 6 . 14 aryloxy-carbonyl group, a C 7 . 19 aralkyl-carbonyl group, a C 7 .
  • each group may has one to three substituents selected from the group consisting of a C x ._, alkylthio group, halogen, a C ⁇ _ 6 alkoxy group, nitro, a C ⁇ _ 6 alkoxy-carbonyl group, a mono- or di-C x .
  • each of said groups may have one to five substituents selected from the group consisting of (i) a C j .g alkyl group, (ii) a C 3 .
  • Q represents a hydrogen atom, a hydrocarbon group as defined in above (1) or an acyl group as defined in above (3);
  • Q represents a hydrocarbon group as defined in above (1) or an acyl group as defined in above (3), or Q and Q may form a ring together with the adjacent nitrogen atom, (6) a group of the formula:
  • a carbamoyl group which may optionally be substituted with 1 or 2 substituents selected from the group consisting of a hydrocarbon group as defined in above (1), a 3- to 8- membered heterocyclic group as defined in above (2) and an acyl group as defined in above ( 3 ) ,
  • ureido group which may optionally be substituted with 1 to 3 substituents selected from the group consisting of a hydrocarbon group as defined in above (1), a 3- to 8- membered heterocyclic group as defined in above (2) and an acyl group as defined in above (3),
  • a thiocarbamoyl group which may optionally be substituted with 1 or 2 substituents selected from the group consisting of a hydrocarbon group as defined in above (1), a 3- to 8- membered heterocyclic group as defined in above (2) and an acyl group as defined in above ( 3 ) , (11) carboxyl group, and
  • Cj__ 6 alkyl group which may optionally be substituted with one to three substituents selected from the group consisting of nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, carboxyl and halogen,
  • R 5 and R 6 are the same or different and each represents (1) hydrogen, (2) halogen, (3) a C 1 . 6 alkyl group which may optionally be substituted with one to three substituents selected from the group consisting of nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, carboxyl and halogen, or (4) a C 6 . l ⁇ aryl group which may optionally be substituted with one to three substituents selected from the group consisting of nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, halogen, a C 6 alkyl group and a C x .
  • a cyclic group selected from the group consisting of (i) a C 6 _ 14 aryl group, (ii) a 5- or 6-membered heterocyclic group bonded through a carbon atom or a condensed ring group thereof with benzene ring or a 5- or 6-membered heterocyclic ring, (iii) a 5- or 6-membered heterocyclic group bonded through a nitrogen atom or a condensed ring group thereof with benzene ring or a 5- or 6-membered heterocyclic ring, (iv) a C 3 . 1A cycloalkyl group and (v) a C 3 .
  • cycloalkenyl group wherein said cyclic group may have one to four substituents selected from the group consisting of nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, carboxyl, halogen, a C ⁇ _ 6 alkyl group and a C ⁇ _ 6 alkoxy group, (6) a C ⁇ _ 6 alkyl group which may optionally be substituted with one to three substituents selected from the group consisting of nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, carboxyl, halogen and a C,_ 6 alkoxyimino group, (7) a C 2 _ 6 alkenyl group, (8) an acyl group selected from the group consisting of a C x _ 6 alkyl-carbonyl group, a C 6 .
  • R represents a hydrogen atom, a Cj.g alkyl group, a C 6 _ 1 aryl group or an amino group which may optionally be substituted with one or two C ⁇ . 6 alkyl groups, (12) a C 3 . 6 cycloalkyloxy group, (13) a Cj .
  • cyclic group may have one to four substituents selected from the group consisting of nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, carboxyl, halogen, a x _ 6 alkyl group and a C x _ 6 alkoxy group,
  • R and R are the same or different, and each represents (1) a hydrogen atom, (2) hydroxy, (3) an optionally substituted C x . 6 alkyl group, (4) an optionally substituted C 3 . 1A cycloalkyl group, (5) an optionally substituted C 2 . 6 alkenyl group, (6) an optionally substituted C 2 . 6 alkynyl group, (7) an optionally substituted C x . 6 alkoxy group, (8) an optionally substituted C 2 _ 6 alkenyloxy group, (9) an optionally substituted C 2 .
  • R and R are the same or different, and each represents (1) a hydrogen atom, (2) an optionally substituted C_ 6 alkyl group, (3) an optionally substituted Cj__ 6 alkoxy group, (4) an optionally substituted C 6 _ 14 aryl group, (5) a C 7 . 19 aralkyl group, (6) an optionally substituted C 6 . 14 aryloxy group, (7) an optionally substituted carbamoyloxy group, (8) a C 1 .
  • acyl group (9) a mono- or di-substituted amino group, (10) a N-mono- or di-substituted carbamoyl group, (11) a group of -S(0) n -R wherein n is 0, 1 or 2 , and R represents a hydrogen atom, an optionally substituted C x _ 6 alkyl group, a C 6 . x _, aryl group or a mono- or di-substituted amino group, (12) a C 6 alkylcarbonyloxy group, (13) a
  • a C 6 alkyl group which may optionally be substituted with one to three substituents selected from the group consisting of (i) hydroxy, (ii) carboxyl, (iii) cyano, (iv) halogen, (v) a C,_ 6 alkoxy group, (vi) a C x _ 6 alkylthio group, (vii) a C _ 6 alkylsulfonyl group, (viii) an acyl group selected from the group consisting of a C 7 alkanoyl group, a C 6 . 1 arylcarbonyl group, a C x _ 6 alkoxycarbonyl group, a C 6 .
  • a C 3 _ cycloalkyl group which may optionally be substituted with one to three substituents selected from the group consisting of (i) hydroxy, (ii) carboxyl, (iii) cyano, (iv) halogen, (v) a C x _ 6 alkoxy group, (vi) a C _ 6 alkylthio group, (vii) a C x _ 6 alkylsulfonyl group, (viii) an acyl group selected from the group consisting of a C 1 . 7 alkanoyl group, a C 6 . 14 arylcarbonyl group, a C x _ 6 alkoxycarbonyl group, a C 6 .
  • (6) a C 2 . 6 alkynyl group which may optionally be substituted with one to three substituents selected from the group consisting of (i) hydroxy, (ii) carboxyl, (iii) cyano, (iv) halogen, (v) a C x _ 6 alkoxy group, (vi) a C x _ 6 alkylthio group, (vii) a C 6 alkylsulfonyl group, (viii) an acyl group selected from the group consisting of a Ci_ 7 alkanoyl group, a C 6 . 1A arylcarbonyl group, a C x _ 6 alkoxycarbonyl group, a C 6 .
  • a C 2 . 6 alkenyloxy group which may optionally be substituted with one to three substituents selected from the group consisting of (i) hydroxy, (ii) carboxyl, (iii) cyano, (iv) halogen, (v) a C ⁇ alkoxy group, (vi) a C x _ 6 alkylthio group, (vii) a C x _ 6 alkylsulfonyl group, (viii) an acyl group selected from the group consisting of a C x _ 7 alkanoyl group, a C 6 . 14 arylcarbonyl group, a C x _ 6 alkoxycarbonyl group, a C 6 .
  • a C 2 . 6 alkynyloxy group which may optionally be substituted with one to three substituents selected from the group consisting of (i) hydroxy, (ii) carboxyl, (iii) cyano, (iv) halogen, (v) a Ci_ 6 alkoxy group, (vi) a C x _ 6 alkylthio group, (vii) a C ⁇ alkylsulfonyl group, (viii) an acyl group selected from the group consisting of a C_,_ 7 alkanoyl group, a C 6 . ⁇ i , arylcarbonyl group, a C x _ 6 alkoxycarbonyl group, a C 6 .
  • a C 6 . 14 aryloxy group which may optionally be substituted with one to five substituents selected from the group consisting of nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, carboxyl, halogen, a C ⁇ alkyl group and a C x _ 6 alkoxy group,
  • (13) a carbamoyloxy group which may optionally be substituted with one or two substituents selected from the group consisting of (i) a C x _ 6 alkyl group, (ii) a 3 - 6 cycloalkyl group, (iii) a C 7 . 19 aralkyl group, (iv) a C,_ 7 alkanoyl group, (v) a C 6 _ 14 arylcarbonyl group, (vi) a C 6 alkoxycarbonyl group, (vii) a C 6 .
  • an acyl group selected from the group consisting of (i) a C 7 alkanoyl group which may optionally be substituted with one to three halogen atoms, (ii) a C 6 - I arylcarbonyl group, (iii) a C x _ 6 alkoxycarbonyl group, (iv) a C 6 . l ⁇ aryloxycarbonyl group, (v) a C 7 . 19 aralkylcarbonyl group and (vi) a C 7 .
  • aralkyloxycarbonyl group (15) an amino group which may optionally be substituted with one or two substituents selected from the group consisting of (i) a C ⁇ alkyl group, (ii) a C 3 . 6 cycloalkyl group, (iii) a C 7 . 19 aralkyl group, (iv) a Ci_ 7 alkanoyl group, (v) a C 6 . 1 arylcarbonyl group, (vi) a C x _ 6 alkoxycarbonyl group, (vii) a C 6 . aryloxycarbonyl group, (viii) a C 7 . 19 aralkylcarbonyl group, (ix) a carbamoyl group which may optionally be substituted with one or two Ci_ 6 alkyl groups and (x) a C x _ 6 alkylsulfonyl group,
  • a carbamoyl group which may optionally be substituted with one or two substituents selected from the group consisting of (i) a C x _ 6 alkyl group, (ii) a . 6 cycloalkyl group, (iii) a C 7 . 19 aralkyl group, (iv) a Ci_ 7 alkanoyl group, (v) a C 6 . ⁇ tl arylcarbonyl group, (vi) a C x _ 6 alkoxycarbonyl group, (vii) a C 6 . 14 aryloxycarbonyl group, (viii) a C 7 . 19 aralkylcarbonyl group, (ix) a carbamoyl group which may optionally be substituted with one or two C x . 6 alkyl groups and (x) a C 6 alkylsulfonyl group,
  • a thiocarbamoyl group which may optionally be substituted with one or two substituents selected from the group consisting of (i) a C x _ 6 alkyl group, (ii) a C 3 . 6 cycloalkyl group, (iii) a C 7 .
  • aralkyl group (iv) a C x _ 7 alkanoyl group, (v) a C 6 _ 14 arylcarbonyl group, (vi) a C ⁇ _ 6 alkoxycarbonyl group, (vii) a C 6 _ aryloxycarbonyl group, (viii) a C 7 _ 19 aralkylcarbonyl group, (ix) a carbamoyl group which may optionally be substituted with one or two C 6 alkyl groups and (x) a d. 6 alkylsulfonyl group,
  • a hydrogen atom (i) a C _ 6 alkyl group which may optionally be substituted with one to three substituents selected from the group consisting of (a) hydroxy, (b) carboxyl, (c) cyano, (d) halogen, (e) a C,_ 6 alkoxy group, (f) a C,_ 6 alkylthio group, (g) a C x _ 6 alkylsulfonyl group, (h) an acyl group selected from the group consisting of a C,_ 7 alkanoyl group, a C 6 . 14 arylcarbonyl group, a C x _ 6 alkoxycarbonyl group, a C 6 .
  • an amino group which may optionally be substituted with one or two substituents selected from the group consisting of (a) a C x _ 6 alkyl group, (b) a C 3 . 6 cycloalkyl group, (c) a C 7 _ 19 aralkyl group, (d) a C x _ 7 alkanoyl group, (e) a C 6 . u arylcarbonyl group, (f) a Cj. ⁇ alkoxycarbonyl group, (g) a C 5 . aryloxycarbonyl group, (h) a C 7 .
  • aralkylcarbonyl group (i) a carbamoyl group which may optionally be substituted with one or two C x _ 6 alkyl groups and (j) a C x _ 6 alkylsulfonyl group, or
  • an acyl group selected from the group consisting of (a) a C]__ 7 alkanoyl group which may optionally be substituted with one to three halogen atoms, (b) a C 6 . arylcarbonyl group, (c) a C x _ 6 alkoxycarbonyl group, (d) a C 6 _ 14 aryloxycarbonyl group, (e) a C 7 . 19 aralkylcarbonyl group and (f) a C 7 . 19 aralkyloxycarbonyl group,
  • a C x _ 6 alkylsulfonyloxy group (21) a group of wherein R 2 and R 25 are the same or different, and each represents a hydrogen atom, a Ci. 6 alkyl group or a C x _ 6 alkoxy group, (22) a 5- or 6-membered heterocyclic group bonded through a nitrogen atom or condensed ring group thereof with benzene ring or a 5- or 6-membered heterocyclic ring, or
  • R represents a hydrogen atom or a alkyl group
  • R represents a C 3 alkyl group which may optionally be substituted with one to three halogen atoms; or R and R 2 may form a C 3 _ 7 cycloalkane ring together with the adjacent carbon atom;
  • A represents (1) a methylene group which may optionally be substituted with one or two halogen atoms or C x _ 6 alkyl groups, (2) a carbonyl group or (3) a thiocarbonyl group; B represents a methylene group which may optionally be substituted with one or two Cj__ 6 alkyl groups; Q represents (1) hydroxy,
  • acyl group selected from the group consisting of a C 1 _ 6 alkyl-carbonyl group, a C 6 _ 14 arylcarbonyl group and a C x _ 6 alkoxycarbonyl group,
  • a group of -N CR 21 R 22 wherein R 2 and R are the same or different, and each represents a hydrogen atom, a C x _ 6 alkyl group or a C ⁇ alkoxy group, or (16) a C 2 . 6 alkenyloxy group;
  • R and R are the same or different, and each represents
  • a C ⁇ s alkyl group which may optionally be substituted with one to three substituents selected from the group consisting of (i) carboxyl, (ii) cyano, (iii) halogen, (iv) a C x _ 6 alkoxy group, (v) a C x _ 6 alkylthio group, (vi) a C x _ 6 alkylsulfonyl group, (vii) a Ci. 7 alkanoyl group, (viii) a C x . 6 alkoxycarbonyl group, (ix) a C 6 _ 14 aryl group, (x) a C x diligent 6 alkylimino group, and (xi) hydroxy,
  • an acyl group selected from the group consisting of (i) a C j . 7 alkanoyl group which may optionally be substituted with one to three halogen atoms, (ii) a C,_ 6 alkoxycarbonyl group and (iii) a C 7 . 19 aralkyloxycarbonyl group,
  • thiocarbamoyl which may optionally be substituted with one or two C ⁇ g alkyl groups
  • R represents (i) a C j ⁇ alkyl group which may optionally be substituted with one to three halogen atoms, (ii) a C 6 . u aryl group, (iii) amino which may optionally be substituted with one or two substituents selected from the group consisting of a C x _ 6 alkyl group and a C x _ 6 alkoxycarbonyl group, and (iv) a C x _ 6 alkoxycarbonyl group,
  • Q represents a C 6 . 10 aryl group which may optionally be substituted with one to three substituents selected from the group consisting of (1) halogen, (2) a C x __, alkyl group which may optionally be substituted with one to five halogen atoms, (3) a C x ._, alkoxy group which may optionally be substituted with one to five halogen atoms, (4) a C ⁇ alkylthio group which may optionally be substituted with one to five halogen atoms and (5) an amino group which may optionally be substituted with one or two alkyl groups;
  • Q represents phenyl which may optionally be substituted with one to three halogen atoms;
  • R 1 and R2 are the same or different and each represents methyl which may optionally be substituted with one to three halogen atoms;
  • R represents a C ⁇ alkyl group, a C 2 .
  • a and B are the same or different and each represents methylene which may optionally be substituted with one or two C ⁇ .
  • _ 4 alkyl groups which may optionally be substituted with one to three halogen atoms; and W represents 0, [ 18 ] 1- [ 1- ( 3 , 5-dichlorophenyl ) -1-methylethyl ] -5-methyl- 3-phenyltetrahydro-l, 3,5-triazine-2( lH)one or a salt thereof,
  • R and R are the same or different and each represents a hydrogen atom or a hydrocarbon group which may optionally be substituted, or a salt thereof, a compound of the formula:
  • R and R are the same or different and each represents a hydrogen atom or a hydrocarbon group which may optionally be substituted, or a salt thereof, and a compound of the formula: R 3 -NH 2 wherein the respective symbols have the same meanings as defined in [2] above or a salt thereof to provide a compound of the formula: wherein R , R , R and R are as defined above; the other symbols have the same meanings as defined in [2] above or a salt thereof; (2) reacting a compound of the formula:
  • X is as defined above; the other symbols have the same meanings as defined in [2] above or a salt thereof with a compound of the formula: X 2 -A-NH-R 3 wherein X 2 is as defined above; A and R3 have the same meanings as defined in [2] above or a salt thereof to provide a compound of the formula: wherein the respective symbols have the same meanings as defined in [2] above or a salt thereof;
  • [25] a method for weeding from a paddy field, plowland, orchard or non-crop land, which comprises scattering an effective amount of the compound as described in [1] above on said paddy field, plowland, orchard or non-crop land.
  • Q represents an aromatic ring group which may optionally be substituted.
  • the aromatic ring group includes aryl, a 5- or 6-membered aromatic heterocyclic group which contains 1 to 4 hetero atoms selected from nitrogen (which may be in the oxide form) , oxygen, and sulfur (which may be in the mono-oxide or dioxide form) or a condensed ring group thereof with benzene ring or a 5- or 6-membered aromatic heterocyclic ring which contains 1 to 4 hetero atoms selected from nitrogen (which may be in the oxide form) , oxygen, and sulfur (which may be in the mono-oxide or dioxide form) .
  • said aryl group includes C 6 .
  • the 5- or 6-membered aromatic heterocyclic group or its condensed ring group includes pyrrolyl (e.g. 1-, 2-, or 3-pyrrolyl), pyrazolyl (e.g. 1-, 3-, 4-, or 5-pyrazolyl) , imidazolyl (e.g. 1-, 2-, 4-, or 5-imidazolyl) , triazolyl (e.g.
  • oxazolyl e.g. 2-, 4-, or 5-oxazolyl
  • isoxazolyl e.g. 3-, 4-, or 5-isoxazolyl
  • oxadiazolyl e.g. 1, 2 , 3-oxadiazol-4- or 5-yl, 1, 2 , 4-oxadiazol-3- or 5-yl, 1, 2 , 5-oxadiazol-3- yl, 1, 3,4-oxadiazol-2-yl
  • thiazolyl e.g. 2-, 4-, or 5-thiazolyl
  • isothiazolyl e.g.
  • thiadiazolyl e.g. 1 , 2 , 3-thiadiazol-4- or 5-yl, 1 , 2 , 4-thiadiazol-3- or 5-yl, 1 , 2 , 5-thiadiazol- 3-yl, l,3,4-thiadiazol-2-yl
  • pyridyl e.g. 2-, 3-, or 4-pyridyl
  • pyridyl in which the nitrogen atom is oxidized e.g. 2-, 3-, or 4-pyridyl-N-oxide
  • pyridazinyl e.g.
  • 3- or 4-pyridazinyl ) pyridazinyl in which one or both of the nitrogen atoms are oxidized (e.g. 3-, 4-, 5- or 6-pyridazinyl-N-oxide) , pyrimidinyl (e.g. 2-, 4-, or 5-pyrimidinyl ) , pyrimidinyl in which one or both of the nitrogen atoms are oxidized (e.g. 2- , 4-, 5- or 6-pyrimidinyl-N-oxide) , pyrazinyl, benzofuryl, indolyl (e.g. 3H-indol-2-, 3-, 4-, 5-, 6- or 7-yl), quinolyl (e.g.
  • pyrazinoquinolyl e.g. pyrazino[2 , 3-d]quinolin-2-yl
  • chromenyl e.g.
  • the aromatic ring group may optionally be substituted by 1 to 4 substituents selected from the group consisting of hydroxy, amino, cyano, sulfamoyl, sulfamoyloxy, mercapto, nitro, halogen, organic residues, and sulfo.
  • substituent groups are cyano, nitro, halogen, and organic residues. Particularly preferred are halogen and organic residues .
  • the halogen as mentioned just above includes fluorine, chlorine, bromine, and iodine.
  • the organic residue includes (1) a hydrocarbon group, (2) a heterocyclic group, (3) an acyl group, (4) a group of the formula -T-Q wherein Q represents a hydrocarbon group, a heterocyclic group, or an acyl group; T represents 0, (0)k S
  • Q represents a hydrogen atom, a hydrocarbon group, or an acyl group
  • Q represents a hydrocarbon group or an acyl group or Q and Q may form a ring together with the adjacent nitrogen atom, (6) a group of the formula:
  • heterocyclic group for said organic residue and the heterocyclic group for Q may optionally be substituted by 1 to 3 substituents selected from the group consisting of the hydrocarbon group, acyl group, and halogen which will be described in detail hereinafter.
  • the hydrocarbon group as used throughout this specification includes a straight-chain, branched, or cyclic aliphatic hydrocarbon group which may contain a double bond or a triple bond, an aryl group and an aralkyl group.
  • said hydrocarbon group includes an alkyl group, an alkenyl group, an alkynyl group, an aryl group, and an aralkyl group.
  • Particularly preferred are Cj_. 19 hydrocarbon group.
  • the alkyl group mentioned above is preferably a straight-chain or branched alkyl group of 1 to 6 carbon atoms or cycloalkyl group of 3 to 14 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, sec-pentyl, isopentyl, neopentyl, cyclopentyl, n-hexyl , isohexyl, cyclohexyl, etc.
  • the alkenyl group mentioned above is preferably a straight-chain or branched alkenyl group of 2 to 6 carbon atoms or cycloalkenyl group of 3 to 14 carbon atoms including allyl, isopropenyl, isobutenyl, 1- methylallyl, 2-pentenyl, 2-hexenyl, 2-cyclohexenyl, etc .
  • the alkynyl group mentioned above is preferably an alkynyl group of 2 to 6 carbon atoms, such as propargyl, 2-butynyl, 3-butynyl, 3-pentynyl, 3-hexynyl, etc.
  • the aryl group mentioned above is preferably an aryl group of 6 to 14 carbon atoms, such as phenyl, naphthyl, anthryl, etc.
  • the aralkyl group mentioned above is preferably an aralkyl group of 7 to 19 carbon atoms, including phenyl-Ci. ⁇ alkyl such as benzyl, phenethyl, phenylpropyl ; benzhydryl, and trityl .
  • hydrocarbon group is an alkyl group, cycloalkyl group, an alkenyl group, cycloalkenyl group or an alkynyl group
  • said hydrocarbon group may optionally be substituted by 1 to 3 substituents selected from the group consisting of hydroxy, cyano, sulfamoyl, mercapto, carboxy, an alkylthio group (e.g. C x __, alkylthio such as methylthio, ethylthio, n- propylthio, isobutylthio, etc.), halogen (e.g. fluorine, chlorine, bromine, iodine), an alkoxy group (e.g. Cj.
  • alkoxy such as methoxy, ethoxy, n-propoxy, tert-butoxy, n-hexyloxy, etc.
  • an alkoxycarbonyl group e.g. C x _ 6 alkoxy-carbonyl such as ethoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl , isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert- butoxycarbonyl, etc.
  • amino an alkylamino group [e.g.
  • alkylamino such as methylamino, ethylamino, n-propylamino, n-butylamino, tert- butylamino, n-pentylamino, n-hexylamino, dimethylamino, diethylamino, methylethylamino, di- (n-propyl) amino, di- ( n-butyl) amino, etc.]
  • an alkoxyi ino group e.g.
  • C x _ 6 alkoxyimino such as methoxyimino, ethoxyimino, n- propoxyimino, tert-butoxyimino, n-hexyloxy-imino, etc.
  • hydroxyimino an alkylsulfonyl group e.g. C x _ 6 alkylsulfonyl such as methylsulfonyl
  • cyano carboxyl, hydroxy, an alkylcarbonyloxy group (e.g. C 6 alkylcarbonyloxy such as methylcarbonyloxy) , an alkanoyl (e.g. C ⁇ alkanoyl such as formyl, acetyl), and an alkylimino group (e.g. C ⁇ alkylimino such as methylimino) .
  • hydrocarbon group when the hydrocarbon group is an aryl group or an aralkyl group, said hydrocarbon group may optionally be substituted by 1 to 5 (preferably 1 to 3 ) substituents selected from the group consisting of an alkyl group (e.g. C x _ 6 alkyl such as methyl, ethyl, n- propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert- butyl , n-pentyl, sec-pentyl, isopentyl, neopentyl, n- hexyl, and isohexyl, C 3 .
  • an alkyl group e.g. C x _ 6 alkyl such as methyl, ethyl, n- propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert- butyl , n-penty
  • cycloalkyl such as cyclohexyl, etc.
  • an alkenyl group e.g. C 2 . 6 alkenyl such as allyl, isopropenyl, isobutenyl, 1-methylallyl , 2- pentenyl, 2-hexenyl, etc.
  • an alkynyl group e.g. C 2 . 6 alkynyl such as propargyl , 2-butynyl, 3-butynyl, 3- pentynyl, 3-hexynyl, etc.
  • an alkoxy group e.g.
  • Ci_ 6 alkoxy such as methoxy, ethoxy, n-propoxy, tert-butoxy, n-hexyloxy, etc.
  • an acyl group e.g. C x _ 7 alkanoyl such as formyl , acetyl, propionyl , butyryl , isobutyryl, pentanoyl, hexanoyl , heptanoyl, etc.; C 6 . 1 arylcarbonyl such as benzoyl, naphthalenecarbonyl, etc.; C_.
  • alkoxy-carbonyl such as methoxycarbonyl, ethoxycarbonyl , propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl , etc.; C 6 _ 1A aryloxy-carbonyl such as phenoxycarbonyl, etc.; C 7 . 19 aralkyl-carbonyl such as phen l-Ci.z, alkylcarbonyl (e.g. benzylcarbonyl, phenethylcarbonyl, phenylpropylcarbonyl , etc.); C 7 .
  • aralkyloxycarbonyl such as benzyloxycarbonyl , etc.], nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, halogen (e.g. fluorine, chlorine, bromine, iodine), and an alkylthio group (e.g. C ⁇ alkylthio group such as methylthio, ethylthio, n-propylthio, isobutylthio, etc . ) .
  • halogen e.g. fluorine, chlorine, bromine, iodine
  • alkylthio group e.g. C ⁇ alkylthio group such as methylthio, ethylthio, n-propylthio, isobutylthio, etc .
  • the heterocyclic group as used throughout this specification includes 3- to 8-membered heterocyclic group, preferably 5- or 6-membered heterocyclic group which contains 1 to 4 hetero atoms selected from nitrogen (which may be in the oxide form) , oxygen, and sulfur (which may be in the mono- or dioxide form) or a condensed ring group thereof with benzene ring or a 3- to 8-membered heterocyclic ring, preferably 5- or 6- membered heterocyclic ring which may contain 1 to 4 hetero atoms selected from nitrogen (which may be in the oxide form) , oxygen, and sulfur (which may be in the mono- or dioxide form) , preferably condensed ring group of such 5- or 6-membered heterocyclic ring with a 5- or 6-membered heterocyclic ring which may contain 1 to 4 hetero atoms selected from nitrogen (which may be in the oxide form), oxygen, and sulfur (which may be in the mono- or dioxide form) .
  • the heterocyclic group includes aziridinyl (e.g. 1- or 2-aziridinyl) , azirinyl (e.g. 1- or 2-azirinyl), azetyl (e.g. 2-, 3- or 4-azetyl), azetidinyl (e.g. 1-, 2-, or 3-azetidinyl) , perhydroazepinyl (e.g. 1-, 2-, 3-, or 4- perhydroazepinyl), perhydroazocinyl (e.g. 1-, 2-, 3-, 4-, or 5-perhydroazocinyl ) , pyrrolyl (e.g.
  • pyrazolyl e.g. 1-, 3-, 4- or 5- pyrazolyl
  • imidazolyl e.g. 1-, 2-, 4-, or 5- imidazolyl
  • triazolyl e.g. 1, 2 , 3-triazol-l- , 4- or 5- yl, 1,2,4-triazol-l-, 3-, 4- or 5-yl
  • tetrazolyl e.g. tetrazol-1-, 2- or 5-yl
  • furyl e.g. 2- or 3-furyl
  • thienyl e.g. 2- or 3-thienyl
  • thienyl in which the sulfur atom is oxidized e.g.
  • thiadiazolyl e.g. 1,2 ,3-thiadiazol-4- or 5-yl, 1 , 2 , 4-thiadiazol-3-, or 5- yl, 1,2 ,5-thiadiazol-3-yl, 1, 3, 4-thiadiazol-2-yl
  • pyrrolidinyl e.g. 1-, 2-, or 3-pyrrolidinyl
  • pyridyl 2, 3-, or 4-pyridyl
  • pyridyl in which the nitrogen atom is oxidized e.g. 2-, 3-, or 4-pyridyl-N-oxide
  • pyridazinyl e.g.
  • 3- or 4-pyridazinyl pyridazinyl in which one or both of the nitrogen atoms are oxidized (e.g. 3-, 4-, 5- or 6-pyridazinyl-N-oxide) , pyrimidinyl (e.g. 2-, 4-, or 5-pyrimidinyl ) , pyrimidinyl in which one or both of the nitrogen atoms are oxidized (e.g. 2- , 4-, 5- or 6-pyrimidinyl-N-oxide) , pyrazinyl, piperidinyl (e.g. 1-, 2-, 3-, or 4-piperidinyl) , piperazinyl (e.g.
  • indolyl e.g. 3H-indol-2-, 3-, 4-, 5-, 6- or 7-yl
  • pyranyl e.g. 2-, 3-, or 4-pyranyl
  • thiopyranyl e.g. 2-, 3-, or 4- thiopyranyl
  • thiopyranyl in which the sulfur atom is oxidized e.g. 2-, 3-, or 4-thiopyranyl-l , 1-dioxide
  • morpholinyl e.g. 2-, 3-, or 4-morpholinyl
  • thiomorpholinyl e.g. quinolyl (e.g.
  • heterocyclic group may optionally be substituted by 1 to 3 substituents selected from the group consisting of an alkyl group (e.g.
  • C j __ 6 alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n- pentyl, sec-pentyl, isopentyl, neopentyl, n-hexyl, and isohexyl, C 3 . 6 cycloalkyl such as cyclohexyl, etc.), an alkenyl group (e.g. C 2 .
  • alkenyl such as allyl, isopropenyl, isobutenyl, 1-methylallyl, 2-pentenyl, 2- hexenyl, etc.
  • alkynyl group e.g. C 2 . 6 alkynyl such as propargyl, 2-butynyl, 3-butynyl, 3-pentynyl, 3- hexynyl, etc.
  • alkoxy group e.g. C ⁇ alkoxy such as methoxy, ethoxy, n-propoxy, tert-butoxy, n-hexyloxy, etc.
  • an acyl group e.g.
  • C ⁇ alkanoyl such as formyl, acetyl, propionyl, butyryl, isobutyryl, pentanoyl, hexanoyl , heptanoyl , etc.
  • C 6 . 14 aryl-carbonyl such as benzoyl, naphthalenecarbonyl , etc.
  • C 6 alkoxy-carbonyl such as methoxycarbonyl, ethoxycarbonyl , propoxycarbonyl, isopropoxycarbonyl , butoxycarbonyl, isobutoxycarbonyl , sec-butoxycarbonyl , tert- butoxycarbonyl, etc.
  • C 6 . 14 aryl-carbonyl such as benzoyl, naphthalenecarbonyl , etc.
  • C 6 alkoxy-carbonyl such as methoxycarbonyl, ethoxycarbonyl , propoxycarbonyl, isopropoxycarbonyl , but
  • aryloxy-carbonyl such as phenoxycarbonyl , etc.
  • C 7 . 19 aralkyl-carbonyl such as phenyl-C j ⁇ alkylcarbonyl (e.g. benzylcarbonyl , phenethylcarbonyl, phenylpropylcarbonyl, etc.); C 7 . 19 aralkyloxycarbonyl such as benzyloxycarbonyl , etc.], nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, halogen (e.g. fluorine, chlorine, bromine, iodine), and an alkylthio group (e.g.
  • alkylthio group such as methylthio, ethylthio, n-propylthio, isobutylthio, etc .
  • the acyl group as used throughout this specification includes an acyl group of 1 to 20 carbon atoms, which is derived from any organic carboxylic acid. Specifically, mention can be made of an alkanoyl group, preferably a C ⁇ alkanoyl group (e.g.
  • arylcarbonyl group preferably a C 6 _ 1 aryl-carbonyl group (e.g. benzoyl, naphthalenecarbonyl, etc.), an alkoxycarbonyl group, preferably a C x _ 6 alkoxy-carbonyl group (e.g.
  • aryloxycarbonyl group preferably a C 6 _ l ⁇ aryloxycarbonyl group (e.g phenoxycarbonyl etc.)
  • aralkylcarbonyl group preferably a C 7 . 19 aralkylcarbonyl group (e.g.
  • phenyl-C ⁇ alkylcarbonyl such as benzylcarbonyl , phenethylcarbonyl , phenylpropylcarbonyl; benzhydrylcarbonyl ; naphthyl-C ⁇ alkylcarbonyl such as naphthylethylcarbonyl, etc.
  • an aralkyloxycarbonyl group preferably a C 7 . 19 aralkyloxycarbonyl (e.g.
  • phenyl-C ⁇ alkoxycarbonyl such as benzyloxycarbonyl, phenethyloxycarbonyl , phenylpropyloxycarbonyl, etc.
  • pyrrolylcarbonyl such as 2-, or 3- pyrrolylcarbonyl
  • pyrazolylcarbonyl such as 3-, 4-, or 5- ⁇ yrazolylcarbonyl
  • imidazolylcarbonyl such as 2-, 4-, or 5-imidazolylcarbonyl
  • triazolylcarbonyl such as 1,2 , 3-triazol-4-ylcarbonyl, and 1, 2 , 4-triazol-3-yl- carbonyl
  • tetrazolylcarbonyl such as IH- or 2H- tetrazol-5-ylcarbonyl
  • furylcarbonyl such as 2- or 3- furylcarbonyl
  • thienylcarbonyl such as 2- or 3- thienylcarbonyl
  • oxazolylcarbonyl such as 2-, 4-, or 5- oxazolylcarbonyl
  • isoxazolylcarbonyl such as 3-, 4-, or 5-isoxazolylcarbonyl
  • acyl group is an alkanoyl group or an alkoxy-carbonyl group
  • said acyl group may optionally be substituted by 1 to 3 substituents selected from the group consisting of hydroxy, cyano, sulfamoyl, mercapto, carboxy, an alkylthio group (e.g. C x _ ⁇ alkylthio such as methylthio, ethylthio, n-propylthio, isopropylthio, isobutylthio, etc.), halogen (e.g. fluorine, chlorine, bromine, iodine) , an alkoxy group (e.g.
  • C x _ 6 alkoxy such as methoxy, ethoxy, n-propoxy, tert-butoxy, n-hexyloxy, etc.
  • an alkoxycarbonyl group e.g. C x _ 6 alkoxy-carbonyl such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl , isopropoxycarbonyl , n-butoxycarbonyl , isobutoxycarbonyl, sec-butoxycarbonyl, tert- butoxycarbonyl , etc.
  • amino an alkylamino group [e.g.
  • alkylamino such as methylamino, ethylamino, n-propylamino, n-butylamino, tert- butylamino, n-pentylamino, n-hexylamino, dimethylamino, diethylamino, methylethylamino, di- (n-propyl ) amino, di- ( n-butyl) amino, etc.], an alkoxyimino group (e.g.
  • C x _ 6 alkoxyimino such as methoxyimino, ethoxyimino, n- propoxyimino, tert-butoxyimino, n-hexyloxy-imino, etc . ) , and hydroxyimino .
  • the acyl group is an aryl-carbonyl group, an aryloxy-carbonyl group, an aralkyl-carbonyl group, an aralkyloxycarbonyl group, a 5- or 6-membered heterocycle-carbonyl group or a 5- or 6-membered heterocycle-acetyl group
  • said acyl group may optionally be substituted by 1 to 5 (preferably 1 to 3 ) substituents selected from the group consisting of an alkyl group (e.g.
  • C x _ 6 alkyl such as methyl, ethyl, n- propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert- butyl, n-pentyl, sec-pentyl, isopentyl, neopentyl, n- hexyl, and isohexyl, C 3 . 6 cycloalkyl such as cyclohexyl, etc.), an alkenyl group (e.g. C 2 .
  • alkenyl such as allyl, isopropenyl, isobutenyl, 1-methylallyl, 2- pentenyl, 2-hexenyl, etc.
  • alkynyl group e.g. C 2 . 6 alkynyl such as propargyl, 2-butynyl, 3-butynyl, 3- pentynyl, 3-hexynyl, etc.
  • alkoxy group e.g. Cj_ 6 alkoxy such as methoxy, ethoxy, n-propoxy, tert-butoxy, n-hexyloxy, etc.
  • an acyl group e.g.
  • C ⁇ alkanoyl such as formyl , acetyl, propionyl, butyryl, isobutyryl, pentanoyl , hexanoyl , heptanoyl, etc.
  • C 6 . 14 arylcarbonyl such as benzoyl, naphthalenecarbonyl, etc.
  • C x _ 6 alkoxy-carbonyl such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl , butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, etc.
  • aryloxy-carbonyl such as phenoxycarbonyl, etc.
  • C 7 . 19 aralkyl-carbonyl such as phenyl-Ci. ⁇ alkylcarbonyl (e.g. benzylcarbonyl, phenethylcarbonyl, phenylpropylcarbonyl, etc.); C 7 . 19 aralkyloxycarbonyl such as phenyl-C ⁇ alkyloxycarbonyl (e.g. benzyloxycarbonyl, etc.)], nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, halogen (e.g.
  • alkylthio group e.g. Cj. ⁇ alkylthio group such as methylthio, ethylthio, n-propylthio, isobutylthio, etc.
  • the group represented by the formula -T-Q specifically includes an alkyloxy group, an alkenyloxy group, an aryloxy group, an aralkyloxy group, a heterocycle-oxy group, an acyloxy group, an alkylthio group, an alkenylthio group, an arylthio group, an aralkylthio group, a heterocycle-thio group, an acylthio group, an alkyldithio group, an aryldithio group, an aralkyldithio group, an alkylsulfinyl group, an alkenylsulfinyl group, an arylsulfinyl group, an aralkylsulfinyl group, a heterocycle-sulfinyl group, an alkylsulfonyl group, an alkenylsulfonyl group, an arylsulfonyl group, an aralkylsulfon
  • the alkyloxy mentioned above is preferably a straight-chain, branched or cyclic alkyloxy group of 1 to 6 carbon atoms, e.g. C _ 6 alkoxy or C 3 _ 6 cycloalkyloxy such as methoxy, ethoxy, n-propoxy, isopropoxy, n- butoxy, isobutoxy, sec-butoxy, tert-butoxy, n- pentyloxy, sec-pentyloxy, isopentyloxy, neopentyloxy, cyclopentyloxy, n-hexyloxy, isohexyloxy, cyclohexyloxy, etc .
  • C _ 6 alkoxy or C 3 _ 6 cycloalkyloxy such as methoxy, ethoxy, n-propoxy, isopropoxy, n- butoxy, isobutoxy, sec-butoxy, tert-butoxy, n- pentyloxy, sec
  • the alkenyloxy group mentioned above is preferably a straight-chain, branched, or cyclic alkenyloxy group of 2 to 6 carbon atoms, e.g. C. 6 alkenyloxy such as allyloxy, isopropenyloxy, 1-butenyloxy, 2-pentenyloxy, or 2-hexenyloxy, C 3 . 6 cycloalkenyloxy such as 2- cyclohexenyloxy, etc.
  • the aryloxy group mentioned above is preferably an aryloxy group of 6 to 14 carbon atoms, such as phenoxy, naphthyloxy, etc.
  • the aralkyloxy group mentioned above is preferably an aralkyloxy group of 7 to 19 carbon atoms, such as alkyloxy, e.g. benzyloxy, phenethyloxy, phenylpropyloxy, etc.
  • the heterocycle-oxy group mentioned above is a group of the formula T'-O- wherein T' represents above- mentioned heterocyclic group, specifically including pyrrolyloxy such as 2- or 3-pyrrolyloxy; pyrazolyloxy such as 3-, 4-, or 5-pyrazolyloxy; i idazolyloxy such as 2-, 4-, or 5-imidazolyloxy; triazolyloxy such as 1,2 , 3-triazol-4-yloxy and 1,2 , 4-triazol-3-yloxy; tetrazolyloxy such as IH- or 2H-tetrazol-5-yloxy; furyloxy such as 2- or 3-furyloxy; thienyloxy such as 2- or 3-thienyloxy; thienyloxy in which the sulfur atom is oxidized such as 2- or 3-thienyl-l, 1-dioxide-oxy; oxazolyloxy such as 2-, 4-, or 5-oxazolyloxy, etc.
  • the acyloxy group mentioned above is a group of the formula T"-0- wherein T" represents above-mentioned acyl, specifically including C_ 6 alkyl-carbonyloxy such as acetoxy, propionyloxy, butyryloxy, pentanoyloxy, and hexanoyloxy; C 7 . 19 aralkylcarbonyloxy such as phenyl-C ⁇ alkylcarbonyloxy, (e.g. benzylcarbonyloxy, phenethylcarbonyloxy, etc.; C 6 .
  • alkylthio group mentioned above is preferably a straight-chain, branched, or cyclic C _ 6 alkylthio group, e.g. C x _ 6 alkylthio and C 3 .
  • cycloalkylthio such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert- butylthio, n-pentylthio, sec-pentylthio, isopentylthio, neopentylthio, cyclopentylthio, n-hexylthio, isohexylthio, cyclohexylthio, etc.
  • the alkenylthio group mentioned above is preferably a straight-chain, branched, or cyclic C 2 _ 6 alkenylthio group, e.g. C 2 _ 6 alkenylthio and C 3 . 6 cycloalkenylthio such as allylthio, isopropenylthio, 1- butenylthio, 2-pentenylthio, 2-hexenylthio, and cyclohexenylthio, etc.
  • the arylthio group mentioned above is preferably a C 6 . 14 arylthio group such as phenylthio, and naphthylthio, etc.
  • the aralkylthio group mentioned above is preferably a C 7 . 19 aralkylthio group, e.g. phenyl-C ⁇ alkylthio such as benzylthio, phenethylthio, and phenylpropylthio, etc.
  • the heterocyclethio group mentioned above is a group of the formula T'-S- wherein T' represents above- mentioned heterocyclic group, specifically including pyrrolylthio such as 2- or 3-pyrrolylthio; pyrazolylthio such as 3-, 4-, or 5-pyrazolylthio; i idazolylthio such as 2-, 4-, or 5-imidazolylthio; triazolylthio such as 1 , 2 , 3-triazol-4-ylthio and 1,2,4- triazol-5-ylthio; tetrazolylthio such as IH- or 2H- tetrazol-5-ylthio; furylthio such as 2- or 3-furylthio; thienylthio such as 2- or 3-thienylthio; thienylthio in which the sulfur atom of the thienyl group is oxidized such as 2- or 3-thienyl-l, 1-dioxide-thio; and o
  • the acylthio group mentioned above is a group of the formula T"-S- wherein T" represents above-mentioned acyl group, specifically including C x _ 6 alkyl- carbonylthio such as acetylthio, propionylthio, butyrylthio, pentanoylthio, and hexanoylthio; phenyl- C X . alkylcarbonylthio such as benzylcarbonylthio and phenethylcarbonylthio; C 6 . 14 arylcarbonylthio such as benzoylthio, and naphthoylthio; heterocycle- carbonylthio such as thienylcarbonylthio and benzothienylcarbonylthio, etc.
  • C x _ 6 alkyl- carbonylthio such as acetylthio, propionylthio, butyrylthio, pentanoylthio
  • the alkyldithio group mentioned above is preferably a straight-chain, branched, or cyclic C ⁇ alkyldithio group, e.g. C x _ 6 alkyldithio or C 3 _ 6 cycloalkyldithio such as methyldithio, ethyldithio, n- propyldithio, cyclopentyldithio, etc.
  • the aryldithio group mentioned above is preferably a C 6 _ l ⁇ aryldithio group such as phenyldithio, naphthyldithio, etc.
  • the aralkyldithio group mentioned above is preferably a C 7 . 19 aralkyldithio group e.g. alkyldithio such as benzyldithio, phenethyldithio, etc.
  • the alkylsulfinyl group mentioned above is preferably a straight-chain, branched, or cyclic C x _ 6 alkylsulfinyl group, e.g. C 6 alkylsulfinyl or C 3 .
  • cycloalkylsulfinyl such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n- hexylsulfinyl, cyclohexylsulfinyl, etc.
  • the alkenylsulfinyl group mentioned above is preferably a straight-chain, branched, or cyclic C 2 . 6 alkenylsulfinyl group, e.g. C 2 . 6 alkenylsulfinyl or C 3 . 6 cycloalkenylsulfinyl gorup such as allylsulfinyl .
  • the arylsulfinyl group mentioned above is preferably a C 6 . 14 arylsulfinyl group such as phenylsulfinyl .
  • the aralkylsulfinyl group mentioned above is preferably a C 7 . 19 aralkylsulfinyl group, e.g. phenyl-C ⁇ 4 alkylsulfinyl such as benzylsulfinyl .
  • the heterocycle-sulfinyl group mentioned above is a group of the formula T'-SO- wherein T' represents above-mentioned heterocyclic group, specifically including pyrrolylsulfinyl such as 2- or 3- pyrrolylsulfinyl; pyrazolylsulfinyl such as 3-, 4- or 5-pyrazolylsulfinyl, etc.
  • the alkylsulfonyl group mentioned above is preferably a straight-chain, branched, or cyclic C x _ 6 alkylsulfonyl group, e.g. C x _ 6 alkylsulfonyl or C 3 . 6 cycloalkylsulfonyl such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, cyclohexylsulfonyl, etc.
  • the alkenylsulfonyl group mentioned above is preferably a straight-chain, branched, or cyclic C 2 _ 6 alkenylsulfonyl group, e.g. C 2 . 6 alkenylsulfonyl or C 3 . 6 cycloalkenylsulfonyl gorup such as allylsulfonyl .
  • the arylsulfonyl group mentioned above is preferably a C 6 . 14 arylsulfonyl group such as phenylsulfonyl, naphthylsulfonyl, etc.
  • the aralkylsulfonyl group mentioned above is preferably a C 7 . 19 aralkylsulfonyl group, e.g. phenyl-Cj. 4 alkylsulfonyl such as benzylsulfonyl , phenethylsulfonyl, phenylpropylsulfonyl, etc.
  • the heterocycle-sulfonyl group mentioned above is a group of the formula T'-S0 2 - wherein T' represents above-mentioned heterocyclic group, specifically including pyrrolylsulfonyl such as 2- or 3- pyrrolylsulfonyl; pyrrazolylsulfonyl such as 3-, 4-, or 5-pyrazolylsulfonyl, etc.
  • T' represents above-mentioned heterocyclic group, specifically including pyrrolylsulfonyl such as 2- or 3- pyrrolylsulfonyl; pyrrazolylsulfonyl such as 3-, 4-, or 5-pyrazolylsulfonyl, etc.
  • T' represents above-mentioned heterocyclic group, specifically including pyrrolylsulfonyl such as 2- or 3- pyrrolylsulfonyl; pyrrazolylsulfonyl such as 3-, 4-, or 5-pyrazo
  • an alkylamino group preferably a mono- or di-(C 1 . 6 alkyl) amino group, e.g. methylamino, ethylamino, n-propylamino, n-butylamino, tert-butylamino, n-pentylamino, n-hexylamino, dimethylamino, diethylamino, methylethylamino, di-(n- propyl ) amino, di- (n-butyl) amino, etc., (2) a cycloalkylamino group, preferably a mono- or di-(C 3 . 6 cycloalkyl) amino group, e.g.
  • ⁇ alkylamino such as benzylamino, 1-phenylethylamino, benzhydrylamino, tritylamino, etc.
  • an acylamino group i.e. a group of the formula ⁇ "T"'N- wherein T" represents above-mentioned acyl group; T"' represents hydrogen, a hydrocarbon group as mentioned above, or an acyl group as mentioned above; T" and T"' may form a ring together with the adjacent nitrogen atom; such as a C ⁇ alkylcarbonylamino, a C(,_ it arylcarbonylamino group, and a heterocycle- carbonylamino group wherein the alkyl, aryl, and heterocyclic group of the heterocycle-carbonylamino are preferably those mentioned in the substituent of the aromatic ring group for Q 1 thus specifically including acetamido, propionamido, butyrylamino, pentanoylamino,
  • Q and Q may form a ring together with the adjacent nitrogen atom, preferably a 3- to 7-membered ring, e.g. pyrrolidino, piperidino, morpholino, thiomorpholino, 1-piperazinyl , aziridino, azetidino, etc.
  • a 3- to 7-membered ring e.g. pyrrolidino, piperidino, morpholino, thiomorpholino, 1-piperazinyl , aziridino, azetidino, etc.
  • ⁇ * specifically includes (1) a mono- or di-alkylsulfamoyl group, preferably a mono- or di(C 1 . 6 alkyl ) sulfamoyl group, e.g. methylsulfamoyl , ethylsulfamoyl, n- propylsulfamoyl , n-hexylsulfamoyl, dimethylsulfamoyl , diethylsulfamoyl, methylethylsulfamoyl , di(n- butyl) sulfamoyl, etc., (2) a cycloalkylsulfamoyl group, preferably a C 3 .
  • cycloalkylsulfamoyl group e.g. cyclopropylsulfamoyl, cyclohexylsulfamoyl , etc.
  • an arylsulfamoyl group preferably a C 6 _ 14 arylsulfamoyl group, e.g. phenylsulfamoyl etc.
  • an aralkylsulfamoyl group preferably a C 7 . 19 aralkylsulfamoyl group, e.g.
  • alkylsulfamoyl such as benzylsulfamoyl or phenylethylsulfamoyl ; benzhydrylsulfamoyl, tritylsulfamoyl, etc., and (5) an acylsulfamoyl group, i.e. a group of the formula T"T"'NS0 2 - wherein the respective symbols have the same meanings as defined hereinbefore, e.g.
  • C _ 6 alkylcarbonylsulfamoyl such as acetylsulfamoyl, phenyl- C X _ alkylcarbonylsulfamoyl such as benzylcarbonyl- sulfamoyl, heterocyclecarbonylsulfamoyl such as
  • Q and Q may form a ring together with the adjacent nitrogen atom, e.g. pyrrolidino, piperidino, morpholino, thiomorpholino, 1-piperadinyl, aziridino, azetidino, etc .
  • the group of the formula Q -S0 2 -0- specifically includes (1) an alkylsulfonyloxy group, preferably a C x . 6 alkylsulfonyloxy group, e.g. methanesulfonyloxy, ethanesulfonyloxy, etc., (2) an arylsulfonyloxy group, preferably a C 6 . l ⁇ arylsulfonyloxy group, e.g. benzenesulfonyloxy, p-toluenesulfonyloxy, etc., (3) an aralkylsulfonyloxy group, preferably a C 7 .
  • aralkylsulfonyloxy group e.g. phenyl-C ⁇ alkylsulfonyloxy such as benzylsulfonyloxy, phenethylsulfonyloxy, etc.
  • an acylsulfonyloxy group e.g. C x _ 6 alkylcarbonylsulfonyloxy such as acetylsulfonyloxy, butyrylsulfonyloxy, etc.
  • R 1 represents a hydrogen atom or a hydrocarbon group which may optionally be substituted.
  • R represents a hydrocarbon group which may optionally be substituted.
  • R and R may form a ring together with the adjacent carbon atom, wherein the ring may optionally be substituted.
  • the hydrocarbon group and its substituent or substituents for R 1 or R 2 mentioned just above includes those mentioned hereinbefore.
  • the ring formed by R and R together with the adjacent carbon atom and which may optionally be substituted includes C A _ 7 cycloalkanes , e.g. cyclobutane, cyclopentane, cyclohexane, cycloheptane, etc. and C 4 _ 7 cycloalkenes , e.g.
  • cyclobutene cyclopentene, cyclohexene, cycloheptene, etc., each of which may optionally be substituted by the substituent or substituents as mentioned for the hydrocarbon group for R 1 and R 2 .
  • the substituent which may be present at 3- to 6- position in the triazine derivative of the present invention includes a group bonded through a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom or halogen (e.g. fluorine, chlorine, bromine, iodine) .
  • halogen e.g. fluorine, chlorine, bromine, iodine
  • the group bonded through a carbon atom is not particularly limited but can be any group which is bonded through a carbon atom.
  • a hydrocarbon group which may optionally be substituted, an acyl group which may optionally be substituted, cyano, a carbamoyl group which may optionally be substituted, a thiocarbamoyl group which may optionally be substituted, an amidino group which may optionally be substituted, or a heterocyclic group bonded through a carbon atom which may optionally be substituted can be mentioned.
  • the hydrocarbon group, its substituent or substituents, and the acyl group, its substituent or substituents may be the same groups as mentioned hereinbefore for substituents on Q .
  • the carbamoyl group or thiocarbamoyl gorup may have 1 or 2 substituents, and the amidino group may have 1 to 3 substituents.
  • the substituents for said carbamoyl, thiocarbamoyl and amidino may for example be the above- mentioned hydrocarbon group, heterocyclic group or acyl group .
  • the above-mentioned heterocyclic group bonded through a carbon atom includes a 3- to 8-membered heterocyclic group which contains 1 to 4 hetero atoms selected from nitrogen (which may be in the oxide form) , oxygen, and sulfur (which may be in the mono- or dioxide form) besides carbon and a condensed ring group thereof with benzene ring or a 3- to 8-membered heterocyclic ring which contains 1 to 4 hetero atoms selected from nitrogen (which may be in the oxide form) , oxygen, and sulfur (which may be in the mono- or dioxide form) .
  • aziridinyl e.g. 2-aziridinyl
  • azirinyl e.g. 2-azirinyl
  • azetyl e.g. 2- or 3-azetyl
  • azetidinyl e.g. 2- or 3- azetidinyl
  • perhydroazepinyl e.g. 2-, 3- or 4- perhydroazepinyl
  • perhydroazocinyl e.g. 2-, 3-, 4- or 5-perhydroazocinyl
  • thienyl e.g. 2- or 3-thienyl
  • furyl e.g. 2- or 3-furyl
  • pyrrolidinyl e.g.
  • 2- or 3- pyrrolidinyl 2- or 3-pyrrolidinyl
  • pyrrolyl e.g. 2- or 3-pyrrolyl
  • oxazolyl e.g. 2-, 4-, or 5-oxazolyl
  • thiazolyl e.g. 2-, 4-, or 5-thiazolyl
  • pyrazolyl e.g. 3-, 4-, or 5- pyrazolyl
  • imidazolyl e.g. 2-, 4-, or 5-imidazolyl
  • isoxazolyl e.g. 3-, 4-, or 5-isoxazolyl
  • isothiazolyl e.g. 3-, 4-, or 5-isothiazolyl
  • oxadiazolyl e.g.
  • 2-, 3-, or 4-pyridyl pyridyl in which the nitrogen atom is oxidized (e.g. 2-, 3- or 4-pyridyl-N-oxido) , pyrimidinyl (e.g. 2-, 4-, or 5-pyrimidinyl) , pyrimidinyl in which one or both of the nitrogen atoms are oxidized (e.g. 2-, 4-, 5- or 6- pyrimidinyl-N-oxido) , thiomorpholinyl (e.g. 2- or 3- thiomorpholinyl) , morpholinyl (e.g. 2- or 3- morpholinyl) , triazinyl (e.g.
  • 3- or 4-pyridazinyl) pyrazinyl, pyridazinyl in which one or both of the nitrogen atoms are oxidized (e.g. 3-, 4-, 5- or 6-pyridazinyl-N-oxido) , benzofuryl, benzothiazolyl , benzoxazolyl, tetrazolof 1, 5- b]pyridazinyl, triazolof 4 , 5-b]pyridazinyl , imidazo[l,2- a]pyridinyl, benzimidazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolidinyl, quinolidinyl, naphthyridinyl (e.g.
  • 1,8- naphthyridinyl 1,8- naphthyridinyl
  • purinyl pteridinyl, dibenzofuranyl, carbazolyl, acridinyl, phenanthridinyl, chromanyl, benzoxazinyl, phenazinyl, phenothiazinyl, phenoxazinyl, etc .
  • the substituent for said heterocyclic group bonded through a carbon atom includes (1) nitro, (2) hydroxy, (3) oxo, (4) thioxo, (5) cyano, (6) carbamoyl, (7) carboxy, (8) a C ⁇ alkoxy-carbonyl group (e.g. methoxycarbonyl, ethoxycarbonyl, etc.), (9) sulfo, (10) halogen (e.g. fluorine, chlorine, bromine, iodine), (11) a C x _ 6 alkoxy group (e.g.
  • a C 6 . 14 aryloxy group e.g. phenoxy, naphthyloxy, etc.
  • a C 6 . 14 aryloxy group which is halogenated by 1 to 3 halogens e.g. halophenyloxy such as o-, m-, or p-chlorophenoxy, o-, m-, or p- bromophenoxy, etc.
  • a C x _ 6 alkylthio group e.g.
  • halogen e.g. fluorine, chlorine, bromine, iodine
  • a C ⁇ alkyl group e.g. methyl, ethyl, propyl, isopropyl, etc.
  • halophenoxy e.g. phenoxy which is substituted by 1 to 3 halogens such as o-, m- , or p-chlorophenoxy, o-, m-, or p-bromophenoxy, etc.
  • thienyl such as 2- or 3-thienyl, furyl such as 2- or 3-furyl
  • pyrazolyl such as 3-, 4-, or 5- pyrazolyl
  • thiazolyl such as 2-, 4-, or 5-thiazolyl
  • isothiazolyl such as 3-, 4-, or 5-isothiazolyl
  • oxazolyl such as 2-, 4-, or 5-oxazolyl
  • isoxazolyl such as 3-, 4-, or 5-isoxazolyl
  • imidazolyl such as 2-, 4-, or 5-imidazo
  • the number of substituents may range from 1 to 5 within the limit of substitutable positions available and preferably 1 to 3.
  • the group bonded through a nitrogen atom is not particularly limited but can be any group which is bonded through a nitrogen atom. For example, there can be used any of (1) nitro, (2) a group of the formula -
  • the hydrocarbon group which may optionally be substituted as mentioned for R, R , R , R , R , or R includes the same hydrocarbon group which may optionally be substituted as mentioned above for the substituent of the aromatic ring group for Q .
  • the optionally substituted hydrocarbon group of the hydrocarbon-oxy group which may optionally be substituted or the hydrocarbon-thio group which may ⁇ 1 optionally be substituted as mentioned for R or R includes the same hydrocarbon group which may optionally be substituted as mentioned above for the substituent of the aromatic ring group for Q .
  • the acyl group which may optionally be substituted mentioned for R 9 or R10 includes the same acyl group which may optionally be substituted as mentioned above for the substituent of the aromatic ring group for Q .
  • R 9 10 substituted mentioned for R or R includes the same carbamoyl group which may optionally be substituted as mentioned above for the substituent of the aromatic ring group for Q .
  • the heterocyclic group mentioned for R 9 , R10, R12, or R 13 includes the same 3- to 8-membered heterocyclic group which contains 1 to 4 hetero atoms selected from nitrogen (which may be in the oxide form) , oxygen, sulfur (which may be in the mono- or dioxide form) , besides carbon and its condensed ring group with benzene ring or a 3- to 8-membered heterocyclic ring which may contain 1 to 4 hetero atoms selected from nitrogen (which may be in the oxide form) , oxygen, and sulfur (which may be in the mono- or dioxide form) as mentioned above for the substituent of the aromatic ring group for Q .
  • the substituent for this heterocyclic group includes the same substituent as those mentioned for the heterocyclic group bonded through a carbon atom.
  • the heterocyclic group bonded through a nitrogen atom includes a 3- to 8-membered heterocyclic group which contains 1 to 4 hetero atoms selected from nitrogen, oxygen, and sulfur besides carbon and a condensed ring group thereof with benzene ring or a 3- to 8-membered heterocyclic ring which may contains 1 to 4 hetero atoms selected from nitrogen, oxygen, and sulfur.
  • 1-aziridinyl 1-azirinyl, 1-azetyl, 1-azetidinyl, 1-perhydroazepinyl , 1-perhydroazocinyl, 1-pyrrolidinyl, 1-pyrrolinyl , 1- pyrrolyl, 1-pyrazolyl, 1-imidazolyl, 1, 2 , 3-triazol-l.- or 2-yl, 1, 2 , 4-triazol-l- or 4-yl, lH-tetrazol-1-yl,
  • the substituent for this heterocyclic group bonded through a nitrogen atom includes the same substituent as those mentioned for the heterocyclic group bonded through a carbon atom.
  • the group bonded through an oxygen atom is not particularly limited but can be any group which is bonded through an oxygen atom.
  • R represents (1) hydrogen, (2) a hydrocarbon group which may optionally be substituted, (3) a heterocyclic group which may optionally be substituted, (4) an acyl group, (5) a carbamoyl group which may optionally be substituted, (6) -SiR 3 wherein R represents a hydrocarbon group which may optionally be substituted, or (7) -SO p R wherein p and R have the same meanings as mentioned above.
  • the hydrocarbon group which may optionally be substituted as mentioned for R or R includes the same hydrocarbon group which may optionally be substituted as those mentioned hereinbefore for the substituent of the aromatic ring group for Q .
  • the heterocyclic group which may optionally be substituted as mentioned for R includes the same heterocyclic group which may optionally be substituted as mentioned above for R 9 or R10.
  • the acyl group for R includes the same acyl group as mentioned for the substituent of the aromatic ring group for Q .
  • the carbamoyl group which may optionally be substituted for R includes the same carbamoyl group which may optionally be substituted as mentioned for the substituent of the aromatic ring group for Q .
  • the group bonded through a sulfur atom is not particularly limited but can be any group which is bonded through a sulfur atom. For example, there can
  • R represents (i) a hydrogen atom, (ii) a hydrocarbon group which may optionally be substituted, or (iii) a heterocyclic group which may optionally be substituted; n represents 0, 1 or 2 , (2) a group of the
  • R represents (i) a hydrogen atom, (ii) a hydrocarbon group which may optionally be substituted, or (iii) a heterocyclic group which may optionally be substituted, (3) a group of the formula - SCOOR wherein R represents (i) a hydrocarbon group which may optionally be substituted, or (ii) a heterocyclic group which may optionally be substituted, or (4) a group of the formula -SNR 32 COOR 33 wherein R 32 and R 3 are the same or different and each represents (i) a hydrocarbon group which may optionally be substituted, or (ii) a heterocyclic group which may optionally be substituted.
  • hydrocarbon group which may optionally benzoyl
  • R , R , R or R includes the same hydrocarbon group which may optionally be substituted as mentioned above for the substituent of the aromatic ring group for Q .
  • the heterocyclic group which may optionally be substituted as mentioned for R 8 , R , R , R or R includes the same heterocyclic group which may
  • the group bonded through a phosphorous atom is not particularly limited but can be any group which is bonded through a phosphorous atom.
  • R 30 can be used any of (1) a group of the formula -P0(0R ) 2 wherein R represents a hydrocarbon group which may optionally be substituted or a heterocyclic group which may optionally be substituted, or (2) a group of the formula -P0(R ) OR wherein R and R are the same or different and each represents a hydrocarbon group which may optionally be substituted or a heterocyclic group which may optionally be substituted.
  • the hydrocarbon group which may optionally be substituted as mentioned for R , R or R includes the same hydrocarbon group which may optionally be substituted as mentioned above for the substituent of the aromatic ring group for Q .
  • the heterocyclic group which may optionally be substituted as mentioned for R , R or R includes the same heterocyclic group which may optionally be substituted as mentioned for R 9 or R10.
  • the triazine derivative may preferably have an optionally substituted aromatic ring group, an optionally substituted aliphatic heterocyclic group or an optionally substituted aliphatic hydrocarbon group at the 3-position.
  • the optionally substituted aromatic ring group as mentioned above includes the same aromatic ring group which may optionally be substituted as mentioned for Q 1 .
  • the aliphatic heterocyclic group of said optionally substituted aliphatic heterocyclic group as mentioned above includes 4- to 6-membered aliphatic heterocyclic group which contains 1 to 3 hetero atoms selected from nitrogen, oxygen, and sulfur, such as oxiranyl , azetidinyl, oxetanyl, thietanyl, pyrrolidinyl, tetrahydrofuryl , thiolanyl, piperidyl, tetrahydropyranyl , morpholinyl, thiomorpholinyl , piperazinyl, etc.
  • the aliphatic hydrocarbon group of the optionally substituted aliphatic hydrocarbon group as mentioned above includes a straight-chain or branched C x _ 6 hydrocarbon group and an alicyclic C 3 . 14 hydrocarbon group .
  • the above-mentioned straight-chain or branched aliphatic hydrocarbon group includes a C x _ 6 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, sec-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, etc., a C 2 .
  • alkenyl group such as allyl, isopropenyl, isobutenyl, 2-pentenyl, 2-hexenyl, etc.
  • a C 2 . 6 alkynyl group such as propargyl, 2-butynyl, 3-butynyl, 3-pentynyl, 3- hexynyl, etc.
  • the above-mentioned alicyclic hydrocarbon group includes a C 3 . cycloalkyl group, preferably C 3 . 7 cycloalkyl group such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, perhydronaphthyl , perhydro- anthranyl, bicyclo[2.2. l]heptyl, etc. and C 3 . 1 cycloalkenyl group, preferably C 3 . 7 cycloalkenyl group such as cyclopropenyl, cyclobuten-1- or 3-yl, cyclopenten-1- , 3-, or 4-yl, cyclohexen-1- or 3-yl, etc.
  • C 3 cycloalkyl group preferably C 3 . 7 cycloalkyl group such as cyclopropyl, cyclobuten-1- or 3-yl, cyclopenten-1- , 3-, or 4-yl,
  • the aliphatic heterocyclic group and aliphatic hydrocarbon group may respectively have 1 to 4 substituents, selected from for example, hydroxy, amino, cyano, sulfamoyl, sulfamoyloxy, mercapto, nitro, halogen, organic residue, sulfo, oxo, and thioxo .
  • halogen and organic residue have the same meaning as defined in substituent of the aromatic ring group for Q as mentioned above.
  • the compound (la) is preferably a compound (I)-(IV) of the formula:
  • Q represents an aromatic ring group which may optionally be substituted
  • R represents a hydrogen atom or a hydrocarbon group which may optionally be substituted
  • R represents a hydrocarbon group which
  • A represents an optionally substituted methylene group, carbonyl group or thiocarbonyl group
  • B represents an optionally substituted methylene group
  • Q , R and R are the same or different and each represents a hydrogen atom or a group bonded through a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom
  • W represents 0 or S : or a salt thereof.
  • Q is preferably phenyl which may optionally be substituted, naphthyl which may optionally be substituted, partially hydrogenated naphthyl (e.g. 1, 2 , 3 , 4-tetrahydro-5- or 6- naphthyl), pyridyl (e.g. 2-, 3- or 4-pyridyl) which may optionally be substituted, thienyl (e.g. 2- or 3-thienyl) which may optionally be substituted or benzofuryl which may optionally be substituted.
  • phenyl which may optionally be substituted is preferred.
  • the substituent for such phenyl, naphthyl, pyridyl, thienyl or benzofuryl group as mentioned above is preferably (1) hydroxy, (2) amino which may optionally be substituted with one or two C ⁇ alkyl groups (e.g. methyl, ethyl, propyl), (3) cyano, (4) sulfamoyl, (5) sulfamoyloxy, (6) mercapto, (7) nitro,
  • halogen e.g. fluorine, chlorine, bromine, iodine
  • sulfo (10) a C x _ 6 alkyl group which may optionally be substituted with one to three substituents selected from the group consisting of nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, carboxy, halogen (e.g. fluorine, chlorine, bromine, iodine), a Cj . . 6 alkoxy group (e.g. methoxy) and a C ⁇ . 6 alkylthio group (e.g.
  • methylthio wherein the alkyl group includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, etc.), (11) a C _ 6 alkoxy group which may optionally be substituted with one to three substituents selected from the group consisting of nitro, amino hydroxy, cyano, sulfamoyl, mercapto, carboxy and halogen (e.g.
  • alkoxy group includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy), (12) a C 7 . 19 aralkyloxy group (e.g. phenyl-C ⁇ alkyloxy such as benzyloxy, phenethyloxy, etc.), (13) a Cj . _ 6 alkylthio group which may optionally be substituted with one to three substituents selected from the group consisting of cyano and halogen (e.g.
  • a C x _ 6 alkylsulfinyl group e.g. methylsulfinyl
  • a C x _ 6 alkylsulfonyl group e.g. methylsulfonyl
  • a C ⁇ . x _ l aryloxy group e.g. phenoxy
  • a C _ 6 alkylsulfonyloxy group e.g. methylsulfonyloxy
  • a C x _ 6 alkoxycarbonyloxy group e.g.
  • halogen or a C _ 6 alkyl group which may optionally be substituted with one to three substituents selected from the group consisting of nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, carboxy, halogen, a Cj_ 6 alkoxy group and a C x _ 6 alkylthio group.
  • halogen or a C_. 3 alkyl group which may optionally be substituted with one to three halogen atoms, wherein the alkyl group includes methyl, ethyl, n-propyl or isopropyl .
  • R is preferably hydrogen or a C 6 alkyl group (e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl) which may optionally be substituted.
  • a C x . 3 alkyl group such as methyl, ethyl, n-propyl or isopropyl.
  • R 2 is preferably a C x _ 6 alkyl group (e.g.
  • Ci_ 3 alkyl group such as methyl, ethyl, n-propyl or isopropyl.
  • the C x _ 6 alkyl group for R and R as mentioned above may optionally be substituted with one to three substituents selected from the group consisting of nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, carboxy and halogen (e.g. fluorine, chlorine, bromine, iodine) .
  • Both R and R may be preferably methyl.
  • the methylene which may optionally be substituted for A or B is represented for example a group of the formula:
  • R and R are the same or different and each represents hydrogen or a hydrocarbon group which may optionally be substituted.
  • R or R is preferably (1) hydrogen, (2) halogen such as fluorine, chlorine, bromine, iodine, (3) a C x _ 6 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, in which the alkyl group may optionally be substituted with one to three substituents selected from the group consisting of nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, carboxy and halogen (e.g.
  • aryl group such as phenyl, in which the aryl group may optionally be substituted with one to three substituents selected from the group consisting of nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, carboxy, halogen (e.g. fluorine, chlorine, bromine, iodine), a Cj__ 4 alkyl group (e.g.
  • R or R is preferably hydrogen or a C x _ 6 alkyl group.
  • Especially preferred is hydrogen or a C ⁇ alkyl group such as methyl, ethyl, n-propyl or isopropyl.
  • a group bonded through a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom for Q has the same meaning as defined above.
  • Q is preferably (1) hydroxy, (2) a C ⁇ alkoxy group, (2) a C 2 . 6 alkenyloxy group, (4) a C 2 . 6 alkynyloxy group, (5) an optionally substituted cyclic group, (6) an optionally substituted C 6 alkyl group, (7) an optionally substituted C 2 . 6 alkenyl group, (8) a C 1 . 20 acyl group, (9) an optionally substituted carbamoyl group, (10) an optionally substituted amidino group,
  • (11) a group of the formula -S(0) n R 20 wherein n is 0, 1 or 2 and R 20 represents a hydrogen atom, a C x . 6 alkyl group, a C 6 . aryl group or an optionally substituted amino group, (12) a C 3 .
  • the alkoxy group as mentioned above includes methoxy, ethoxy, n-propoxy, or isopropoxy.
  • the alkenyloxy group as mentioned above includes allyloxy, isopropenyloxy or isobutenyloxy .
  • the alkynyloxy group as mentioned above includes propargyloxy, 2-butynyloxy, or 3-butynyloxy .
  • the cyclic group as mentioned above includes (i) a C 6 - H aryl group, (ii) a 5- or 6-membered heterocyclic group bonded through a carbon atom or a condensed ring group thereof with benzene ring or a 5- or 6-membered heterocyclic ring, (iii) a 5- or 6-membered heterocyclic group bonded through a nitrogen atom or a condensed ring group thereof with benzene ring or a 5- or 6-membered heterocyclic ring, (iv) a C 3 . 14 cycloalkyl group or (v) a C 3 . 14 cycloalkenyl group.
  • the C 6 . 14 aryl group includes phenyl, 1-naphthyl or 2-naphthyl.
  • the 5- or 6-membered heterocyclic group bonded through a carbon atom or a condensed ring group thereof with benzene ring or a 5- or 6-membered heterocyclic ring includes thienyl (e.g. 2- or 3-thienyl), furyl (e.g. 2- or 3-furyl), pyrrolidinyl (e.g. 2- or 3- pyrrolidinyl ) , pyrrolyl (e.g. 2- or 3-pyrrolyl), oxazolyl (e.g. 2-, 4-, or 5-oxazolyl), thiazolyl (e.g. 2-, 4-, or 5-thiazolyl) , pyrazolyl (e.g.
  • 2-, 4-, or 5- pyrimidinyl pyrimidinyl in which one or both of the nitrogen atoms are oxidized (e.g. N-oxido-2-, 4- or 5- pyrimidinyl) , thiomorpholinyl (e.g. 2- or 3- thiomorpholinyl) , morpholinyl (e.g. 2- or 3- morpholinyl) , piperidinyl, pyranyl, thiopyranyl, oxazinyl (e.g. 1, 4-oxazinyl) , thiazinyl (e.g. 1,4- thiazinyl, 1, 3-thiazinyl ) , piperazinyl (e.g.
  • N-oxido- 3- or 4-pyridazinyl) benzofuryl, benzothiazolyl , benzoxazolyl, tetrazolo[ 1, 5-b]pyridazinyl , triazolo[4 , 5-b]pyridazinyl, imidazof 1 , 2-a]pyridinyl, benzimidazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl , quinoxalinyl, indolidinyl, quinolidinyl, naphthyridinyl (e.g.
  • the 5- or 6-membered heterocyclic group bonded through a nitrogen atom or a condensed ring group thereof with benzene ring or a 5- or 6-membered heterocyclic ring includes 1-pyrrolidinyl, 1- pyrrolinyl, 1-pyrrolyl, 1-pyrazolyl, 1-imidazolyl, 1,2,3-triazol-l- or 2-yl, 1, 2 , 4-triazol-l- or 4-yl, 1H- tetrazol-1-yl, 2H-tetrazol-2-yl, 1-piperidinyl, 4- thiomorpholinyl, 1-morpholinyl, 1-dihydropyridyl, 1- tetrahydropyridyl , 2- or 4-oxodihydropyridin-l-yl, 1- tetrahydropyrimidyl , 1-perhydropyrimidyl, 1- dihydrotriazinyl, 1-tetrahydrotriazinyl,
  • the C 3 . ⁇ e ⁇ cycloalkyl group includes a C 3 . 7 cycloalkyl group such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl.
  • the C 3. cycloalkenyl group includes 2-cyclohexen-l-yl or 3-cyclohexen-l-yl .
  • the substituent for the cyclic group is preferably nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, carboxy, halogen (e.g. fluorine, chlorine, bromine, iodine), a C x _ 6 alkyl group (e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl) and a C x _ 6 alkoxy group (e.g. methoxy, ethoxy).
  • halogen e.g. fluorine, chlorine, bromine, iodine
  • a C x _ 6 alkyl group e.g. methyl, ethyl, n-propyl
  • the number of the substituents for the cyclic group is 1 to 4 , preferably 1 to 3 , especially preferably 1 or 2.
  • the C x _ 6 alkyl group for the optionally substitued C x _ 6 alkyl group includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, sec-pentyl, isopentyl, neopentyl or n-hexyl.
  • the substituent for the C x _ 6 alkyl group includes nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, carboxy, halogen (e.g. fluorine, chlorine, bromine, iodine), or a C x _ 6 alkoxyimino group (e.g. methoxyimino, ethoxyimino) .
  • halogen e.g. fluorine, chlorine, bromine, iodine
  • a C x _ 6 alkoxyimino group e.g. methoxyimino, ethoxyimino
  • Especially preferred is a C ⁇ alkoxyimino group.
  • the number of the substituents for the alkyl group is 1 to 3.
  • the C 2 _ 6 alkenyl group includes allyl, isopropenyl, isobutenyl, 1-methylallyl , 2-pentenyl or 2-hexenyl.
  • the substituent for the C. 6 alkenyl group includes nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, carboxyx or halogen (e.g. fluorine, chlorine, bromine, iodine) .
  • the number of the substituents for the alkenyl group is 1 to 3.
  • the Ci ⁇ o acyl group includes (1) a C ⁇ alkyl-carbonyl such as formyl, acetyl, propionyl, butyryl, isobutyryl, pentanoyl or hexanoyl , (2) a C 6 . 1A arylcarbonyl group such as benzoyl or naphthalenecarbonyl, or (3) a C ⁇ alkoxycarbonyl group such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl or tert-butoxycarbonyl .
  • a C ⁇ alkyl-carbonyl such as formyl, acetyl, propionyl, butyryl, isobutyryl, pentanoyl or hexanoyl
  • a C 6 . 1A arylcarbonyl group such as benzoyl or n
  • the optionally substituted carbamoyl group includes carbamoyl or a mono- or di-Cj.g alkylcarbamoyl group such as methylcarbamoyl or dimethylcarbamoyl .
  • the substituent for the optionally substituted amidino group includes a C x _ 6 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, sec-pentyl, isopentyl, neopentyl or n-hexyl.
  • the number of the substituents is 1 to 3.
  • the Cj__ 6 alkyl group for R as mentioned above includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, sec-pentyl, isopentyl, neopentyl or n-hexyl.
  • R 20 for R includes phenyl, 1-naphthyl or 2-naphthyl .
  • the substituent for the amino group of R 20 includes a C x . 6 alkyl group as mentioned above. The number of the substituents is 1 to 2.
  • the C 3 . 6 cycloalkyloxy group as mentioned above includes cyclopropyloxy, cyclobutyloxy, cyclopentyloxy or cyclohexyloxy.
  • the C x _ 6 alkylcarbonyloxy group includes acetyloxy, propionyloxy, butyryloxy, isobutyryloxy, pentanoyloxy or hexanoyloxy.
  • the C 6 . arylcarbonyloxy group includes phenylcarbonyloxy.
  • the substituent for the carbamoyloxy includes a
  • C x _ 6 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, sec-pentyl, isopentyl, neopentyl or n-hexyl.
  • the substituent for the amino group includes (1) a
  • C_ ⁇ _ 6 alkyl group e.g. methyl, ethyl, propyl
  • a C ⁇ alkyl-carbonyl group e.g. methylcarbonyl, ethylcarbonyl
  • a C x _ 6 alkylsulfonyl group e.g. methylsurfonyl, ethylsulfonyl
  • aminocarbonyl which may optionally be substituted with one or two C x _ 6 alkyl groups, in which the alkyl group has the same meaning as mentioned for the substituent for the carbamoyloxy group.
  • the number of the substituents is 1 to 2.
  • the C j. , 6 alkyl group for R 2 1 or R22 has the same meaning as mentioned for the substituent for the carbamoyloxy group.
  • the C x . ⁇ alkoxy group for R 21 or R22 includes methoxy or ethoxy.
  • R 22 includes methylthio or ethylthio .
  • Q is preferably an optionally cyclic group.
  • a C 6 _ 14 aryl group such as phenyl
  • aryl group may optionally be substituted with one to five halogen atoms
  • (2) pyridyl such as 2-, 3- or 4-pyridyl
  • (3) pyrrolyl such as 1-pyrrolyl
  • thiazolyl such as 2 ⁇ , 4- or 5-thiazolyl
  • piperidyl such as 1-piperidyl
  • (6) morphorinyl such as 4-morphorinyl
  • imidazopyridyl and (8) a C 3 . 6 cycloalkyl group
  • a C 3 . 6 cycloalkyl group such as
  • cyclohexyl are preferable.
  • Q is phenyl which may optionally be substituted with one to three halogen atoms.
  • the group bonded through a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom for R or R has the same meaning as defined above. Among them, hydroxy, amino, cyano, sulfamoyl, sulfamoyloxy, mercapto, nitro, halogen, an organic residue or sulfo group is preferable.
  • the halogen or the organic residue has the same meaning as defined for Q .
  • R 3 or R is preferably (1) a hydrogen atom, (2) hydroxy, (3) an optionally substituted C x _ 6 alkyl group (e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, etc.), (4) an optionally substituted C 3 _ cycloalkyl group (e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.), (5) an optionally substituted C 2 _ 6 alkenyl group (e.g.
  • aryl group e.g. phenyl, 1-naphthyl, 2-naphthyl, etc.
  • a C 7 . 19 aralkyl group e.g. phenyl-C ⁇ alkyl such as benzyl, phenethyl or phenylpropyl; benzhydryl; trityl , etc.
  • an optionally substituted C 6 . 1A aryloxy group e.g. phenoxy, naphthyloxy, etc.
  • carbamoyloxy group e.g. a C ⁇ o acyl group
  • C ⁇ alkanoyl such as formyl , acetyl, propionyl, butyryl, isobutyryl, pentanoyl , hexanoyl or heptanoyl, which may optionally be substituted with one to three halogen atoms such as fluorine;
  • C 6 . 14 arylcarbonyl such as benzoyl or naphthalenecarbonyl;
  • C x _ 6 alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl , butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, or tert-butoxycarbonyl; C 6 .
  • aryloxycarbonyl such as phenoxycarbonyl; C 7 . 19 aralkylcarbonyl such as alkylcarbonyl, e.g. benzylcarbonyl, phenethylcarbonyl, phenylpropylcarbonyl; C 7 _ 19 aralkyloxycarbonyl such as benzyloxycarbonyl , etc.
  • an optionally substituted amino group (16) an optionally substituted carbamoyl group, (17) an optionally substituted thiocarbamoyl group, (18) a group of the formula -S(0) n -R wherein n is 0, 1 or 2 and R 2 represents a hydrogen atom, an optionally substituted C xtician 6 alkyl group (e.g.
  • a C 6 . 14 aryl group e.g. phenyl, naphthyl
  • an optionally substituted amino group or a C ⁇ o acyl group e.g. acyl group as mentioned above
  • a C x _ 6 alkylcarbonyloxy group e.g.
  • acetyloxy, propionyloxy, butyryloxy, isobutyryloxy, pentanoyloxy, hexanoyloxy, etc.), (20) a Cj . , 6 alkylsulfonyloxy group (e.g. methylsulfonyloxy, etc.), (21) a group of the formula -N CR R wherein R and R are the same or different, and each represents a hydrogen atom, a C x _ 6 alkyl group (e.g.
  • a C x _ 6 alkoxy group e.g. methoxy, ethoxy, etc.
  • 6-membered heterocyclic group bonded through a nitrogen atom or condensed ring group thereof with benzene ring or a 5- or 6-membered heterocyclic ring as defined for
  • Q represents a C x _ 6 alkoxy group (e.g. methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, sec-pentyloxy, isopentyloxy, neopentyloxy, etc. ) .
  • the substituent of the C j. _ 6 alkyl group for R 3 , R or R , or the substituent of the C 3 . 14 cycloalkyl group, C x _ 6 alkoxy group, C 2 . 6 alkenyl group, C 2 . 5 alkynyl group, C 2 . 6 alkenyloxy group, or C 2 _ 5 alkynyloxy group for R or R includes hydroxy, carboxy, cyano, halogen (e.g. fluorine, chlorine, bromine, iodine), a C _ 6 alkoxy group (e.g.
  • a Cj_. 6 alkylthio group e.g. methylthio, ethylthio, propylthio, etc.
  • a Cj__ 6 alkylsulfonyl group e.g. methylsulfonyl, ethylsulfonyl , propylsulfonyl , etc.
  • a Cj . 6 alkylthio group e.g. methylthio, ethylthio, propylthio, etc.
  • a Cj__ 6 alkylsulfonyl group e.g. methylsulfonyl, ethylsulfonyl , propylsulfonyl , etc.
  • a Cj . 6 alkylthio group e.g. methylthio, ethylthio, propylthio, etc.
  • acyl group e.g. C _ 7 alkanoyl such as formyl, acetyl, propionyl, butyryl , isobutyryl, pentanoyl, hexanoyl or heptanoyl ; C 6 _ 1 arylcarbonyl such as benzoyl or naphthalenecarbonyl; C x _ 6 alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl , butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, or tert-butoxycarbonyl; C 6 _ 1 aryloxycarbonyl such as phenoxycarbonyl; C 7 _ 19 aralkylcarbonyl such as phenyl-Cj_.
  • C 6 _ 7 alkanoyl such as formyl, acetyl, propionyl, butyryl ,
  • a alkylcarbonyl e.g. benzylcarbonyl, phenethylcarbonyl, phenylpropylcarbonyl; C 7 . 19 aralkyloxycarbonyl such as benzyloxycarbonyl, etc.), a C 6 . 1A aryl group (e.g. phenyl, naphthyl, etc.), a C x _ 7 alkanoyloxy group (e.g.
  • C x _ 6 alkylimino e.g. methylimino, ethylimino, etc.
  • the number of the substituent is 1 to 3.
  • the substituent of the C 6 . 1 aryl group, C 6 . 1 aryloxy group or C 3 _ 1A cycloalkyl group for R or R is preferably nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, carboxy, halogen (e.g. fluorine, chlorine, bromine, iodine), a C w alkyl group (e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl etc.) or a C x _ 6 alkoxy group (e.g. methoxy, ethoxy, etc.).
  • the number of the substituent is 1 to 5, preferably 1 to 3.
  • the substituent of amino for R , R , or R , or the substituent of carbamoyl, thicarbamoyl or carbamoyloxy is preferably a C x _ 6 alkyl group (e.g. methyl, ethyl), a C 3 . 5 cycloalkyl group (e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl), a C 7 . 19 aralkyl group (e.g. phenyl-Cj. 4 alkyl such as benzyl), a C _ 7 alkanoyl group (e.g.
  • a C 6 _ 1 arylcarbonyl group e.g. benzoyl, naphthalenecarbonyl, etc.
  • a C_ 6 alkoxycarbonyl group e.g. methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl , etc.
  • a C 6 _ 1 arylcarbonyl group e.g. benzoyl, naphthalenecarbonyl, etc.
  • a C_ 6 alkoxycarbonyl group e.g. methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl , etc.
  • aryloxycarbonyl group e.g. phenoxycarbonyl, etc.
  • a C 7 . 19 aralkylcarbonyl group e.g. phenyl-C ⁇ alkylcarbonyl such as benzylcarbonyl, phenethylcarbonyl, phenylpropylcarbonyl, etc.
  • carbamoyl which may optionally be substituted one or two C x _ 6 alkyl groups (e.g. methyl, ethyl, propyl, etc.), or a C x _ 6 alkylsulfonyl group (e.g.
  • R or R is preferably (1) a C x _ 6 alkyl group which may optionally be substituted with one to three substituents selected from the group consisting of hydroxy, carboxy, halogen, a C _ 6 alkoxy group, a C ⁇ alkoxycarbonyl group and a C x _ 7 alkanoyloxy group, (2) a C x _ 6 alkoxy group, (3) a C 6 .
  • R represents a hydrogen atom or a C ⁇ alkyl group
  • R represents a C ⁇ alkyl group which may optionally be substituted with one to three halogen atoms; or R 1 and R2 may form a C 3 . 7 cycloalkane ring together with the adjacent carbon atom;
  • A represents (1) a methylene group which may optionally be substituted with one or two halogen atoms or C 6 alkyl groups, (2) a carbonyl group or (3) a thiocarbonyl group;
  • B represents a methylene group which may optionally be substituted with one or two C x _ 6 alkyl groups;
  • Q represents (1) hydroxy, (2) a Cj_ 6 alkoxy group,
  • an acyl group selected from the group consisting of a Cj__ 6 alkyl-carbonyl group, a C 6 _ 1A arylcarbonyl group and a C x _ 6 alkoxycarbonyl group, (7) a carbamoyl group which may optionally be substituted with one or two C x _ 6 alkyl groups,
  • a group of -N CR R wherein R and R are the same or different, and each represents a hydrogen atom, a C x _ 6 alkyl group or a C x _ 6 alkoxy group;
  • R and R are the same or different, and each represents
  • a C _ 6 alkyl group which may optionally be substituted with one to three substituents selected from the group consisting of (i) carboxyl, (ii) cyano, (iii) halogen, (iv) a C x _ 6 alkoxy group, (v) a C j _ 6 alkylthio group, (vi) a C x _ 6 alkylsulfonyl group, (vii) a C alkanoyl group, (viii) a C x _ 6 alkoxycarbonyl group, (ix) a C 6 . 1 aryl group, (x) a C 6 alkylimino group, and (xi) hydroxy,
  • carbamoyloxy which may optionally be substituted with one or two C x _ 6 alkyl groups
  • an acyl group selected from the group consisting of (i) a Ci. 7 alkanoyl group which may optionally be substituted with one to three halogen atoms, (ii) a C 1 . 6 alkoxycarbonyl group and (iii) a C 7 .
  • aralkyloxycarbonyl group (4) amino which may optionally be substituted with one or two substituents selected from the group consisting of (i) a C x _ 6 alkyl group, (ii) a C x _ 7 alkanoyl group, (iii) carbamoyl which may optionally be substituted with one or two C j __ 6 alkyl groups and (iv) a C _ 6 alkylsulfonyl group,
  • (21) a pyrrolidinyl group or a morpholinyl group, or (22) a group of -P0(R ) 2 wherein R represents a C _ 6 alkoxy group.
  • Compound (I) or (II) is especially preferable.
  • Especially preferred compound is a compound represented by the formula:
  • Q represents a C 6 . 10 aryl group which may optionally be substituted with one to three substituents selected from the group consisting of (1) halogen, (2) a C A alkyl group which may optionally be substituted with one to five halogen atoms, (3) a C alkoxy group which may optionally be substituted with one to five halogen atoms, (4) a Cj.
  • a alkylthio group which may optionally be substituted with one to five halogen atoms and (5) an amino group which may optionally be substituted with one or two Cj.
  • alkyl groups Q represents phenyl which may optionally be substituted with one to three halogen atoms; R 1 and R2 are the same or different and each represents methyl which may optionally be substituted with one to three halogen atoms; R represents a C X .
  • a and B are the same or different and each represents methylene which may optionally be substituted with one or two C ⁇ alkyl groups which may optionally be substituted with one to three halogen atoms; and W represents 0.
  • the compounds of the present invention may form agrochemically acceptable salts with bases such as inorganic or organic bases, and when the compounds contain the basic nitrogen atom and basic groups such as amino in substituents, they may form agrochemically acceptable acid addition salts with inorganic or organic acids.
  • the salt of compound (la) with an inorganic base includes salts with alkali metals (e.g. sodium, potassium, etc.), alkaline earth metals (e.g.
  • salt of compound (la) with an organic base includes salts with dimethylamine, triethylamine, piperazine, pyrrolidine, piperidine, 2- phenylethylamine, benzylamine, ethanolamine, or diethanolamine .
  • the inorganic acid addition salt of compound (la) includes salts with hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, and phosphoric acid
  • the organic acid addition salt of compound (la) includes salts with p-toluenesulfonic acid, methanesulfonic acid, formic acid and trifluoroacetic acid.
  • the compound or a salt thereof of the present invention can be used as a highly safe agrochemical typically herbicide. It is especially of value as a herbicide, since the compound or salt exhibits a broad spectrum against weeds, such as those listed below, at low concentrations substantially without doing any harm to crop plants such as rice, wheat, barley, maize, soybean, and other useful plants, that is to say with high safety.
  • the list of weeds which can be controlled includes paddy field weeds such as Echinochloa crus- galli var . oryzicola , Cyperus difformis Linnaeus, Scirpus iuncoides Roxburgh var. hotarui Ohwi,
  • the compound or a salt thereof of the invention shows a high selectivity against crop-weeds in its action, and is least toxic to mammals, fishes and shellfishes and can be used very safely as a herbicide for the paddy field, plow land, orchard, and non-crop land without polluting the environment.
  • the compound or a salt thereof of the present invention for application of the compound or a salt thereof of the present invention as an agrochemical, particularly a herbicide, it can be used in any application form that is known or available for agro- chemicals in general.
  • a suitable liquid vehicle or admixed with, or adsorbed on, a suitable solid carrier for use as an emulsifiable liquids, an oil-soluble, a spray, wettable powders, dusts, driftless (DL) powders, granules, fine granules, fine granules F, flowables, dry flowables, jumbo granules, and tablets.
  • a suitable liquid vehicle or admixed with, or adsorbed on, a suitable solid carrier for use as an emulsifiable liquids, an oil-soluble, a spray, wettable powders, dusts, driftless (DL) powders, granules, fine granules, fine granules F
  • liquid vehicle that can be used includes water, alcohols (e.g. methanol, ethanol, 1- propanol, 2-propanol, ethylene glycol, etc.), ketones (e.g. acetone, methyl ethyl ketone, etc.), ethers (e.g.
  • dioxane tetrahydrofuran
  • ethylene glycol monomethyl ether diethylene glycol monomethyl ether
  • propylene glycol monomethyl ether etc.
  • aliphatic hydrocarbons e.g. kerosene, fuel oil, machine oil, etc.
  • aromatic hydrocarbons e.g. benzene, toluene, xylene, solvent naphtha, methylnaphthalene, etc.
  • halogenated hydrocarbons e.g. dichloromethane, chloroform, carbon tetrachloride, etc.
  • acid amides e.g. N,N- dimethylformamide, N,N-dimethylacetamide, etc.
  • esters e.g.
  • nitriles e.g. acetonitrile, propionitrile, etc.
  • solvents can be used either singly or in combination.
  • the solid carrier includes vegetable powders (e.g. soybean meal, tobacco flour, wheat flour, sawdust, etc.), mineral powders (e.g. clays such as kaolin, bentonite, acid clay, and clay, and talcs such as talc powder, pyrophyllite
  • vegetable powders e.g. soybean meal, tobacco flour, wheat flour, sawdust, etc.
  • mineral powders e.g. clays such as kaolin, bentonite, acid clay, and clay
  • talcs such as talc powder, pyrophyllite
  • the liquid vehicle or solid carrier is used in a proportion of generally about 1 to 99 weight % and preferably about 1 to 80 weight % based on the whole composition.
  • the surfactant which can be used as said emulsifier, spreader, penetrating agent, or dispersant as necessary are not limited but includes nonionic and anionic surfactans such as soaps, polyoxyethylene alkyl aryl ethers [e.g. Noigen TM and E-A142TM (TM stands for trademark and the same applies below; Dai-ichi Kogyo Seiyaku Co. Ltd.)], polyoxyethylene aryl esters (e.g.
  • Nonal TM; Toho Chemical alkyl sulfates (e.g. Emal 10TM, Emal 40 ; Kao Corporation) , alkylbenzenesulfonic acid salts (e.g. Neogen TM, Neogen TTM, Dai-ichi Kogyo Seiyaku
  • Neopelex TM Kao Corporation
  • polyethylene glycol ethers e.g. Nonipol 85 TM, Nonipol 100TM, Nonipol
  • the surfactant can be used in a proportion of generally about 0.1% to about 50% and preferably about 0.1% to about 25% with respect to the whole composition.
  • the preferred concentration of the compound or a salt thereof of the present invention in herbicidal compositions is about 1 to 90 weight % for emulsifiable liquids and wettable powders, about 0.01 to 10 weight % for oil-solubles, dusts, and DL powders, and about 0.05 to 10 weight % for fine granules F and granules, although the concentration may be adjusted according to the intended application.
  • Emulsifiable liquids and wettable powders may be diluted (for example, 100- 100 , 000-fold) with water or the like in advance in the field and applied.
  • the amount of the compound or salt of the present invention for use as a herbicide varies with the type of field, season, application method, weeds to be controlled, and crop plants under cultivation. Generally, however, the proper amount in terms of the active ingredient, i.e. compound (la) or its salt is: about 0.05 to 50 g, preferably about 0.1 to 10 g, per are of paddy field, or about 0.05 to 50 g, preferably about 0.1 to 10 g, per are of plow land.
  • the compound or a salt thereof of the present invention can be used with advantage as a preemergence soil treatment or a leaf-stem-soil treatment.
  • the herbicidal composition of the present invention can be safely applied without harm to crop plants immediately after transplanting of rice seedlings or even 2-3 weeks after the transplanting, with a lasting herbicidal effect.
  • the agrochemical composition containing the compound or a salt thereof of the present invention can be supplemented, where necessary, with other herbicides, plant growth regulators, germicides (e.g. organochlorine fungicides, organosulfur fungicides, azole fungicides, antibiotics, etc.), insecticides (e.g.
  • sulfonylurea herbicides [bensulfuron-methyl , pyrazosulfuron-ethyl , imazosulfuron, sulfosulfuron, cinosulfuron, azimsulfuron, halosulfuron, ethoxysulfuron, l-(2- cyclopropylcarbonylphenylsulfamoyl) -3-( 4 , 6- dimethoxypyrimidin-2-yl)urea, etc.], (2) pyrazole herbicides [pyrazolate, pyrazoxyfen, benzofenap, etc.], (3) carbamate herbicides [benthiocarb, molinate
  • the compound or a salt thereof of the present invention can also be used as a pesticide or germicide in the same manner as above.
  • the compound (la) or a salt thereof of the present invention can be synthesized by a process in which a urea or thiourea compound, or a salt thereof, which has a group of the formula:
  • said compound (la) or a salt thereof can be produced in accordance with the following reaction schemes 1 to 9.
  • salts of the following compounds those of the same kinds as the salt of compound (la) described hereinbefore can be employed.
  • R and R are the same or different and each represents hydrogen or an optionally substituted hydrocarbon group, and the other symbols have the same meanings as defined hereinbefore.
  • R 7 and R8 has the same meanings as defined for R5 and R 6 .
  • This reaction is an addition-condensation reaction among compound (V), (VI), (VII) and (VIII).
  • reaction relative to compound (V) or a salt thereof, generally about equimolar to a large excess of compound (VI), (VII) and (VIII) or a salt thereof is used.
  • This reaction can be carried out in a solvent that does not interfere with the reaction.
  • the solvent suitable for this reaction includes aromatic hydrocarbons such as benzene, toluene, xylene, etc., halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1 , 2-dichloroethane, etc., ethers such as ethyl ether, isopropyl ether, di- oxane, tetrahydrofuran (hereinafter briefly, THF), 1,2- dimethoxyethane, etc., nitriles such as acetonitrile, propionitrile, etc., ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, etc., esters such as ethyl acetate, butyl acetate, etc., amides such as N,N-dimethylformamide (hereinafter briefly, DMF), N,N- dimethylacetamide, etc., dimethyl sulfox
  • reaction temperature is generally about -10 °C to 150°C and preferably about 10°C to 100°C.
  • the reaction goes to completion in about 30 minutes to about 20 hours and the completion of reaction can be ascertained by thin-layer chromatography or high- performance liquid chromatography.
  • the leaving group represented by X and X includes halogen (e.g. fluorine, chlorine, bromine, etc.) and a group of the formula:
  • Q and k have the same meanings as defined hereinbefore, e.g. methoxy, methylsulfonyloxy, trifluoromethylsulfonyloxy, p-toluenesulfonyloxy, benzenesulfonyloxy, etc. Particularly preferred is halogen, with chlorine or bromine being most advantageous .
  • This reaction is a condensation reaction between compound (V) and compound (IX).
  • compound (V) or a salt thereof and compound (IX) or a salt thereof are used generally in a substantially equimolar ratio.
  • This reaction can be carried out in a solvent that does not interfere with the reaction.
  • the solvent thus may be any of the solvents mentioned for the reaction according to Reaction Scheme 1.
  • the reaction can be generally promoted by adding a base.
  • the base that can be used for this purpose includes organic bases such as triethylamine, tri-n- propylamine, N,N-dimethylaniline, pyridine, 1,8- diazabicyclo[5.4.0. ] -7-undecene (hereinafter briefly, DBU) , l,4-diazabicyclo[2.2.2]octane, 1,5- diazabicyclo[4.3.0 ]non-5-ene, etc.; inorganic bases such as sodium hydride, potassium hydroxide, potassium carbonate, sodium carbonate, sodium hydroxide, etc.; n- butyllithium, lithium diisopropylamide, etc.
  • the base can be used generally in a proportion of about 0.01 to 5 moles per mole of compound (V) or a salt thereof.
  • the reaction temperature is generally about -10 °C to
  • reaction Scheme 3 Reaction Scheme 3
  • This reaction is a condensation reaction between compound (X) and compound (XI).
  • compound (X) or a salt thereof and compound (XI) or a salt thereof are used generally in a substantially equimolar ratio.
  • This reaction can be carried out in a solvent that does not interfere with the reaction, and the solvent that can be used includes the same solvents as those mentioned for the reaction according to Reaction Scheme 1.
  • This reaction can be generally promoted by adding a base.
  • the base that can be used for this purpose includes the same bases as those mentioned for the reaction according to Reaction Scheme 2.
  • the base can be used generally in a proportion of about 0.01 to 5 molar equivalents relative to one molar of compound (X) .
  • the reaction temperature is generally about -10 °C to 150°C and preferably about 10°C to 100°C.
  • the reaction goes to completion in about 30 minutes to about 20 hours and the completion of reaction can be ascertained by thin-layer chromatography or high- performance liquid chromatography.
  • This reaction is a condensation reaction between compound (XII) and compound (XI).
  • compound (XII) or a salt thereof and compound (XI) or a salt thereof are used generally in substantially equimolar ratio.
  • This reaction can be carried out in a solvent that does not interfere with the reaction.
  • the solvent which can be used includes the same solvents as those mentioned for the reaction according to Reaction Scheme 1.
  • This reaction can be generally promoted by adding a base.
  • the base which can be used for this purpose includes the same acids as those mentioned for the reaction according to Reaction Scheme 2.
  • the base can be used generally in a proportion of about 0.01 to 5 moles per mole of compound (XII) or a salt thereof.
  • the reaction temperature is generally about -10 °C to 150°C and preferably about 10°C to 100°C.
  • the reaction goes to completion in about 30 minutes to about 20 hours and the completion of reaction can be ascertained by thin-layer chromatography or high-performance liquid chromatography .
  • This reaction is a condensation reaction between compound (V) and compound (XIII).
  • compound (V) or a salt thereof and compound (XIII) or a salt thereof are used generally in a substantially equimolar ratio.
  • This reaction can be carried out in a solvent which does not interfere with the reaction.
  • the solvent that can be used includes the same solvents as those mentioned for the reaction according to Reaction Scheme 1.
  • This reaction can be generally promoted by adding a base.
  • the base that can be used for this purpose includes the same bases as those mentioned for the reaction according to Reaction Scheme 3.
  • the base can be used generally in a proportion of about 0.01 to 5 moles per mole of compound (V) or a salt thereof.
  • the reaction temperature is generally about -10°C to 150°C and preferably about 10° to 100°C.
  • the reaction goes to completion in about 30 minutes to about 20 hours and the completion of reaction can be ascertained by thin- layer chromatography or high-performance liquid chromatography .
  • This reaction is a condensation reaction between compound (XIV) and compound (XV) .
  • compound (XIV) or a salt thereof and compound (XV) or a salt thereof are used generally in a substantially equimolar ratio.
  • This reaction can be carried out in a solvent that does not interfere with the reaction.
  • the solvent may be any of the solvents mentioned for the reaction according to Reaction Scheme 1.
  • This reaction can be generally promoted by adding a base.
  • the base that can be used for this purpose includes the same bases as those mentioned for the reaction according to Reaction Scheme 1.
  • the base can be used generally in a proportion of about 0.01 to 5 moles per mole of compound (XIV) or a salt thereof.
  • reaction temperature is generally about -10 °C to 150°C and preferably about 10°C to 100°C.
  • the reaction goes to completion in about 30 minutes to about 20 hours, and the completing of reaction can be ascertained by thin-layer chromatography or high- performance liquid chromatography.
  • This reaction is a condensation reaction between compound (XVI) and compound (XV).
  • compound (XVI) or a salt thereof and compound (XV) or a salt thereof are used generally in a substantially equimolar ratio.
  • This reaction can be carried out in a solvent which does not interfere with the reaction.
  • the solvent that can be used includes the same solvents as those mentioned for the reaction according to Reaction Scheme 1.
  • This reaction can be generally promoted by adding a base.
  • the base that can be used for this purpose includes the same bases as those mentioned for the reaction according to Reaction Scheme 2.
  • the base can be used generally in a proportion of about 0.01 to 5 moles per mole of compound (XVI) or a salt thereof.
  • the reaction temperature is generally about -10 °C to 150°C and preferably about 10°C to 100°C.
  • the reaction goes to completion in about 30 minutes to about 20 hours and the completion of reaction can be ascertained by thin-layer chromatography or high-performance liquid chromatography .
  • the compound (la) can also be produced according to the following Reaction Scheme 8-13 or analogous method thereof.
  • This reaction is a condensation reaction between compound (XVII) and compound (XVIII).
  • reaction for this reaction, compound (XVII) or a salt thereof and compound (XVIII) or a salt thereof are used generally in a substantially equimolar ratio.
  • This reaction can be carried out in a solvent that does not interfere with the reaction.
  • the solvent may be any of the solvents mentioned for the reaction according to Reaction Scheme 1.
  • This reaction can be generally promoted by adding a base.
  • the base that can be used for this purpose includes the same bases as those mentioned for the reaction according to Reaction Scheme 2.
  • the base can be used generally in a proportion of about 0.01 to 5 moles per mole of compound (XVII) or a salt thereof.
  • the reaction temperature is generally about -10°C to 150°C and preferably about 10°C to 100°C.
  • the reaction goes to completion in about 30 minutes to about 20 hours, and the completing of reaction can be ascertained by thin-layer chromatography or high- performance liquid chromatography.
  • This reaction is a condensation reaction between compound (XIX) and compound (XVIII).
  • reaction for this reaction, compound (XIX) or a salt thereof and compound (XVIII) or a salt thereof are used generally in a substantially equimolar ratio.
  • This reaction can be carried out in a solvent that does not interfere with the reaction.
  • the solvent may be any of the solvents mentioned for the reaction according to Reaction Scheme 1.
  • This reaction can be generally promoted by adding a base.
  • the base that can be used for this purpose includes the same bases as those mentioned for the reaction according to Reaction Scheme 2.
  • the base can be used generally in a proportion of about 0.01 to 3 moles per mole of compound (XIX) or a salt thereof.
  • the reaction temperature is generally about -10°C to 150°C and preferably about 10°C to 100°C.
  • the reaction goes to completion in about 30 minutes to about 20 hours, and the completing of reaction can be ascertained by thin-layer chromatography or high- performance liquid chromatography.
  • This reaction is a condensation reaction between compound (XX) and compound (XXI).
  • compound (XX) or a salt thereof and compound (XXI) or a salt thereof are used generally in a substantially equimolar ratio.
  • This reaction can be carried out in a solvent that does not interfere with the reaction.
  • the solvent may be any of the solvents mentioned for the reaction according to Reaction Scheme 1.
  • This reaction can be generally promoted by adding a base.
  • the base that can be used for this purpose includes the same bases as those mentioned for the reaction according to Reaction Scheme 2.
  • the base can be used generally in a proportion of about 0.01 to 3 moles per mole of compound (XX) or a salt thereof.
  • the reaction temperature is generally about -10°C to 150°C and preferably about 10°C to 100°C.
  • the reaction goes to completion in about 30 minutes to about 20 hours, and the completing of reaction can be ascertained by thin-layer chromatography or high-performance liquid chromatography .
  • This reaction is a condensation reaction between compound (XXII) and compound (XXI).
  • compound (XXII) or a salt thereof and compound (XXI) or a salt thereof are used generally in a substantially equimolar ratio.
  • This reaction can be carried out in a solvent that does not interfere with the reaction.
  • the solvent may be any of the solvents mentioned for the reaction according to Reaction Scheme 1.
  • This reaction can be generally promoted by adding a base.
  • the base that can be used for this purpose includes the same bases as those mentioned for the reaction according to Reaction Scheme 2.
  • the base can be used generally in a proportion of about 0.01 to 3 moles per mole of compound (XXII) or a salt thereof.
  • the reaction temperature is generally about -10 °C to
  • reaction Scheme 12 Reaction Scheme 12
  • This reaction is a condensation reaction between compound (XXIII) and compound (XXI).
  • compound (XXIII) or a salt thereof and compound (XXI) or a salt thereof are used generally in a substantially equimolar ratio.
  • This reaction can be carried out in a solvent that does not interfere with the reaction.
  • the solvent may be any of the solvents mentioned for the reaction according to Reaction Scheme 1.
  • This reaction can be generally promoted by adding a base.
  • the base that can be used for this purpose includes the same bases as those mentioned for the reaction according to Reaction Scheme 2.
  • the base can be used generally in a proportion of about 0.01 to 5 moles per mole of compound (XXIII) or a salt thereof.
  • the reaction temperature is generally about -10°C to 150°C and preferably about 10°C to 100°C.
  • the reaction goes to completion in about 30 minutes to about 20 hours, and the completing of reaction can be ascertained by thin-layer chromatography or high- performance liquid chromatography.
  • This reaction is a condensation reaction between compound (XXIV) and compound (XXI).
  • compound (XXIV) or a salt thereof and compound (XXI) or a salt thereof are used generally in a substantially equimolar ratio.
  • This reaction can be carried out in a solvent which does not interfere with the reaction.
  • the solvent that can be used includes the same solvents as those mentioned for the reaction according to Reaction Scheme 1.
  • This reaction can be generally promoted by adding a base.
  • the base that can be used for this purpose includes the same bases as those mentioned for the reaction according to Reaction Scheme 2.
  • the base can be used generally in a proportion of about 0.01 to 3 moles per mole of compound (XXIV) or a salt thereof.
  • the reaction temperature is generally about -10°C to
  • reaction goes to completion in about 30 minutes to about 20 hours and the completion of reaction can be ascertained by thin-layer chromatography or high-performance liquid chromatography.
  • Reaction Scheme 14 wherein X or X represents a C x _ 6 alkoxy group, and the other symbols have the same meanings as defined hereinbefore .
  • the alkoxy group mentioned for X and X includes methoxy, ethoxy, n-propoxy or isopropoxy.
  • This reaction is a condensation reaction between compound (XXII) and compound (XXIII).
  • compound (XXII) or a salt thereof and compound (XXIII) or a salt thereof are used generally in a substantially equimolar ratio.
  • This reaction can be carried out in a solvent that does not interfere with the reaction.
  • the solvent may be any of the solvents mentioned for the reaction according to Reaction Scheme 1.
  • This reaction can be generally promoted by adding an acid.
  • the acid that can be used for this purpose includes inorganic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, etc.; organic acids such as formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, p-toluenesulfonic acid, etc.; and Lewis acids such as trifluoroborane, titanium tetrachloride, zinc chloride etc.
  • the acid can be used generally in a proportion of about 0.01 to 5 moles per mole of compound (XXII) or a salt thereof.
  • the reaction temperature is generally about -10°C to 150°C and preferably about 10°C to 100°C.
  • the reaction goes to completion in about 30 minutes to about 20 hours, and the completing of reaction can be ascertained by thin-layer chromatography or high-performance liquid chromatography .
  • This reaction is a condensation reaction between compound (XXIV) and compound (XXIII).
  • compound (XXIV) or a salt thereof and compound (XXIII) or a salt thereof are used generally in a substantially equimolar ratio.
  • This reaction can be carried out in a solvent that does not interfere with the reaction.
  • the solvent may be any of the solvents mentioned for the reaction according to Reaction Scheme 1.
  • This reaction can be generally promoted by adding an acid.
  • the base that can be used for this purpose includes the same acids as those mentioned for the reaction according to Reaction Scheme 14.
  • the acid can be used generally in a proportion of about 0.01 to 5 moles per mole of compound (XXIV) or a salt thereof.
  • the reaction temperature is generally about -10°C to
  • reaction Scheme 16 ⁇
  • This reaction is a condensation reaction between compound (XXV) and compound (XI).
  • compound (XXV) or a salt thereof and compound (XI) or a salt thereof are used generally in a substantially equimolar ratio.
  • This reaction can be carried out in a solvent that does not interfere with the reaction.
  • the solvent may be any of the solvents mentioned for the reaction according to Reaction Scheme 1.
  • This reaction can be generally promoted by adding a base.
  • the base that can be used for this purpose includes the same bases as those mentioned for the reaction according to Reaction Scheme 2.
  • the base can be used generally in a proportion of about 0.01 to 5 moles per mole of compound (XXV) or a salt thereof.
  • the reaction temperature is generally about -10°C to 150°C and preferably about 10°C to 100°C.
  • the reaction goes to completion in about 30 minutes to about 20 hours, and the completing of reaction can be ascertained by thin-layer chromatography or high- performance liquid chromatography.
  • This reaction is a condensation reaction between compound (XXVI) and compound (XI).
  • compound (XXVI) or a salt thereof and compound (XI) or a salt thereof are used generally in a substantially equimolar ratio.
  • This reaction can be carried out in a solvent that does not interfere with the reaction.
  • the solvent may be any of the solvents mentioned for the reaction according to Reaction Scheme 1.
  • This reaction can be generally promoted by adding a base.
  • the base that can be used for this purpose includes the same bases as those mentioned for the reaction according to Reaction Scheme 2.
  • the base can be used generally in a proportion of about 0.01 to 5 moles per mole of compound (XXVI) or a salt thereof.
  • the reaction temperature is generally about -10°C to 150°C and preferably about 10°C to 100°C.
  • the reaction goes to completion in about 30 minutes to about 20 hours, and the completing of reaction can be ascertained by thin-layer chromatography or high- performance liquid chromatography.
  • compound in which R is an alkyl group can be synthesized by using compound having carboxy on R as a starting material according to the reaction described in J. Chem. Soc., Chem. Commun., pl298, 1984.
  • compound in which R is hydroxy can be synthesized by using compound having hydrogen at the 1- position of R as a starting material according to the reaction described in J. Org . Chem., P6239, 1992.
  • compound in which R is a group bonded through an oxygen atom can be synthesized by using compound in which such R is hydroxy as a starting material .
  • R is amino
  • compound in which R is hydrogen as a starting material according to the reaction described in Synth., PI, 1977.
  • compound in which R is a group bonded through a nitrogen atom can be synthesized by using compound in which R is amino as a starting material.
  • Compound (III) can be synthesized by using compound (XVII) and (XIX) as starting materials according to the reaction described in Bull. Chem. Soc. Jpn., P1297, 1974.
  • the reaction product may be in the form of a salt with a base used in the reaction. If such is the case, the salt can be converted to a free form of the compound by adding an acid such as the above-mentioned acid.
  • the compound (la) produced and (I) -(IV) are a free form of the compound, it can be converted to a base salt by adding the corresponding base such as the above- mentioned base.
  • the above reaction conducted in the presence of an acid may yield a salt with an acid used.
  • the salt can be converted to a free form of the compound by adding a base such as the above- mentioned base.
  • a base such as the above- mentioned base.
  • the compound (la) and (I)-(IV) obtained as a free form of the compound it can be converted to form an acid addition salt with the corresponding acid such as the above-mentioned acid.
  • the compound (la) or a salt thereof thus obtained can be isolated and purified by the per se known procedures such as concentration, concentration under reduced pressure, extraction, redistribution, crystallization, recrystallization, and chromatography.
  • the starting compounds inclusive of their salts, which are used for producing the compound (la) are either known compounds or compounds which can be easily prepared from known compounds .
  • compound (V) or a salt thereof can be produced by the process described in Chemical Review, 43, p203, 1948 or any process analogous thereto, e.g. in accordance with the following reaction scheme.
  • Reaction Scheme 18
  • Compound (VI) or (VII) or a salt thereof is for example formaldehyde, acetaldehyde or acetone, and is either a known compound or can be produced easily from known compound. Also, it is a carbonyl equivalent such as paraformaldehyde or dimethoxyethane, and is also either a known compound or can be produced wasily from known compound.
  • Compound (VIII) or a salt thereof is for example amines such as ammonia, methylamine, aniline or 0- methylhydroxylamine, and is either a known compound or can be produced wasily from known compound.
  • Compound (IX) or a salt thereof is for example bischloromethylmethylamine, and is either a known compound or can be produced easily from known compound.
  • Compound (X) or a salt thereof can be produced for example by the following reaction scheme. Reaction Scheme 20
  • Compound (X) or a salt thereof can be produced, for example, by the following reaction scheme.
  • Compound (XIII) or a salt thereof in for example chlorobenzylideneurethane is a known compound or can be produced from known compound easily.
  • Compound (XV) or a salt thereof is for example N- methylurethane, and such a compound is a known compound or can be produced from known compound easily.
  • Compound (XVI) can also be produced for example by the following reaction scheme.
  • Compound (XVIII) and compound (XVIII) or salts thereof are for example methyl iodide, acetyl chloride, N,N-dimethylcarbanoyl chloride, etc., and such a compound is known compound or can be produced from known compound easily.
  • Compound (XXI) or salts thereof are for example allyl iodide, benzoyl chloride, chloroethyl carbonate, N,N-dimethylcarbamoyl chloride, or methane sulfonyl chloride, etc., and such a compound is known compound or can be produced from known compound easily.
  • Compound (XXII) or salts thereof can be produced for example by the following reaction scheme.
  • Compound (XXIII) or salts thereof are for example dimethoxymethane, etc., and such a compound is known compound or can be produced from known compound easily.
  • Compound (XXIV) or salts thereof can be produced for example by the following reaction scheme.
  • Compound (XXV) or salts thereof can be produced for example by the following reaction scheme.
  • Compound (XXVI) or salts thereof can be produced for example by the following reaction scheme.
  • the compound or a salt thereof of the present invention has potent herbicidal activity against a broad spectrum of weeds including paddy field weeds and plow land weeds at low concentrations. Furthermore, it is least phytotoxic to crop plants such as rice, wheat, barley, soybean, and corn plants, thus having very satisfactory selective herbicidal activity. Moreover, this selective herbicidal action lasts long. In addition, the compound or a salt thereof of the present invention does no substantial harm to mammalian animals and fish, is free from the pollution problem, and can be used very safely as a herbicide in paddy fields, plow lands, orchards, and non-crop lands.
  • room temperature is generally used to mean a temperature within the range of about 10 to 30 °C.
  • H-NMR stands for proton nuclear magnetic resonance spectrum. The NMR spectra were recorded with Bruker AC200P Spectrometer (200 MHz) using tetramethylsilane as internal standard and the chemical shifts ( ⁇ ) were expressed in ppm.
  • IR stands for infrared absorption spectrum. The IR spectra were recorded with Shimadzu IR420 or IR435 Infrared Spectrophotometer and the absorption bands were expressed in wave-numbers (cm " ) . The other symbols used in the working examples have the following meanings.
  • DMSO-d 6 deuterated dimethyl sulfoxide; s: singlet; d: doublet; t: triplet; q: quartet; dd: doublet doublet; ddd: doublet doublet doublet; dt: doublet triplet; td: triplet doublet; qd: quartet doublet; m: multiplet, br.: broad; J: coupling constant; %: weight percent; v/v: volume-to-volume ratio; Me: methyl; Et: ethyl; n-Pr: n-propyl; i-Pr: isopropyl; n-Bu: n-butyl; dec: decomposition; def.s: defused singlet.
  • the solvent was then distilled off and the residue was diluted with ethyl acetate and water. Then, under ice-cooling, the mixture was acidified with 2 N hydrochloric acid. After phase separation, the aqueous layer was further extracted with ethyl acetate. The ethyl acetate layers were combined and dried over anhydrous magnesium sulfate, and the solvent was distilled off.
  • the ice-water bath was then removed and the reaction mixture was irradiated with a high- pressure mercury vapor lamp for 10 minutes (at ca 0°C) .
  • the solvent was then distilled off and the residue was diluted with water and extracted with chloroform.
  • the chloroform layer was washed with saturated aqueous solution of sodium hydrogen carbonate and dried over : anhydrous magnesium sulfate and the solvent was distilled off.
  • dimethyl sulfate 42 ⁇ l , 0.44 mmol
  • 60% sodium hydride/oil 10 mg, 0.25 mmol
  • reaction mixture was cooled to room temperature and added dropwise to a solution of l-[ l-( 3 , 5-dichlorophenyl) -1- methylethyl]-3-phenylurea (9.70 g, 30.0 mmol) in dichloromethane (100 ml) under ice-cooling. Then, a solution of triethylamine (9.15 ml, 66.0 mmol) in dichloromethane (50 ml) was added dropwise and the mixture was stirred under ice-cooling for 30 minutes. This reaction mixture was added dropwise into 10% sodium hydroxide/water and stirred for 15 minutes under ice-cooling.
  • the dichloromethane layer was separated and the aqueous layer was further extracted with 100 ml of dichloromethane.
  • the dichloromethane layers are combined, washed with 300 ml of water twice, 0.1N- hydrochloric acid, and saturated NaCl/H 2 0 in that order and dried over MgSO A .
  • reaction mixture was added in small portions to 25 ml of saturated sodium hydrogencarbonate/H 2 0 under ice-cooling and extracted with 30 ml of ethyl acetate. After phase separation, the organic layer was washed with 25 ml of saturated NaCl/H 2 0 and dried over MgS0 A and the solvent was distilled off.

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Abstract

La présente invention concerne un dérivé de 1,3,5-triazine totalement hydrogéné ou complètement hydrogéné, qui présente (i) un groupe selon la formule (a). Dans cette dernière, Q1 représente un groupe de chaîne aromatique qui peut éventuellement être substitué; R1 représente un atome d'hydrogène ou un groupe d'hydrocarbone qui peut être éventuellement substitué; R2 représente un groupe d'hydrocarbure qui peut éventuellement être substitué ou R1 et R2 peuvent former une chaîne ensemble avec l'atome de carbone adjacent. Cette chaîne peut éventuellement être substituée, en position -1, et (ii) des groupes oxo ou thioxo en position -2, et (iii) qui peuvent être substitués à chaque position -3 à -6, à condition que ce dérivé de triazine ne présente pas de groupes oxo au niveau des deux positions -4 et -6, ou un sel de ces derniers. L'invention traite également d'un procédé pour sa production et une composé. Le composé ou le sel de ce dernier présente une forte activité herbicide contre un large spectre de mauvaises herbes, y compris les mauvaises herbes des rizières, et les mauvaises herbes de labour, à de faibles concentrations. En outre, il est moins phytotoxique pour les plantes cultivées telles que le riz, le blé, l'orge, le soja et le maïs et présente ainsi une action herbicide sélective très satisfaisante. En outre, cette action herbicide sélective est une action à longue durée. Par ailleurs, ce composé ou ce sel ne nuit sensiblement pas aux animaux mammifères, aux poissons et aux coquillages. Il n'entraîne également aucune pollution et peut être utilisé en toute sécurité comme herbicide dans des rizières, des labours, des vergers, et des terres non cultivées.
PCT/JP1998/001872 1997-04-25 1998-04-23 Derives de triazine, production de ces produits et composition agrochimique WO1998049150A1 (fr)

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US7928227B2 (en) * 2003-02-28 2011-04-19 Bayer Healthcare Llc 2-oxo-1,3,5-perhydrotriazapine derivatives useful in the treatment of hyper-proliferative, angiogenesis, and inflammatory disorders
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RU2551688C1 (ru) * 2013-11-05 2015-05-27 Федеральное Государственное Бюджетное Учреждение Науки Институт Нефтехимии И Катализа Ран Способ получения n-[4-(ти)оксо-1,3,5-триазинан-1-ил]ариламидов
US11897871B1 (en) 2021-06-14 2024-02-13 Scorpion Therapeutics, Inc. Methods for treating cancer
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US7897623B2 (en) 1999-01-13 2011-03-01 Bayer Healthcare Llc ω-carboxyl aryl substituted diphenyl ureas as p38 kinase inhibitors
US8124630B2 (en) 1999-01-13 2012-02-28 Bayer Healthcare Llc ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
US8841330B2 (en) 1999-01-13 2014-09-23 Bayer Healthcare Llc Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
US7838541B2 (en) 2002-02-11 2010-11-23 Bayer Healthcare, Llc Aryl ureas with angiogenesis inhibiting activity
US8242147B2 (en) 2002-02-11 2012-08-14 Bayer Healthcare Llc Aryl ureas with angiogenisis inhibiting activity
US7928227B2 (en) * 2003-02-28 2011-04-19 Bayer Healthcare Llc 2-oxo-1,3,5-perhydrotriazapine derivatives useful in the treatment of hyper-proliferative, angiogenesis, and inflammatory disorders
US8796250B2 (en) 2003-05-20 2014-08-05 Bayer Healthcare Llc Diaryl ureas for diseases mediated by PDGFR
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