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WO1998006709A1 - Composes d'urees cycliques, leur production et leur utilisation comme herbicides - Google Patents

Composes d'urees cycliques, leur production et leur utilisation comme herbicides Download PDF

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Publication number
WO1998006709A1
WO1998006709A1 PCT/JP1997/002799 JP9702799W WO9806709A1 WO 1998006709 A1 WO1998006709 A1 WO 1998006709A1 JP 9702799 W JP9702799 W JP 9702799W WO 9806709 A1 WO9806709 A1 WO 9806709A1
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group
substituted
optionally
compound
ring
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English (en)
Inventor
Shigeyuki Itoh
Shogo Kobayashi
Yasushi Tanaka
Hiroyuki Suzuki
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Takeda Pharmaceutical Co Ltd
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Takeda Chemical Industries Ltd
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Priority to AU37855/97A priority Critical patent/AU3785597A/en
Publication of WO1998006709A1 publication Critical patent/WO1998006709A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
    • C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
    • C07D273/04—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen 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
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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

Definitions

  • the present invention relates to a novel cyclic urea compound having excellent and selective herbicidal activity, a production method for the compound, and an agrochemical composition comprising the compound.
  • the cyclic urea compound of the invention is a novel compound having excellent herbicidal activity against paddy field and plowland 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 .
  • l-aryl-3-aralkyl-cyclic urea compounds have been reported. For example, a cyclic urea compound of the formula:
  • R represents benzyl, diphenylmethyl , or 1- phenylethyl ;
  • Rj represents phenyl, is disclosed in Chemical Abstracts Vol. 63, 1965, Col. 600, "Hydroxylamine derivatives, XIV. 3 , 5-Dioxo-l , 2 , 3-oxadi- azolidines" and a cyclic urea compound of the formula:
  • R represents phenyl
  • R [ represents benzyl
  • R [ represents benzyl
  • R [ is disclosed in Chemical Abstracts, Vol. 76, 1972, p461, 153677v.
  • a cyclic urea compound in which the methylene moiety of the benzyl group substituting one of ring-forming nitrogen atoms is mono- or di-substituted.
  • JP-A 176475/1991 describes a cyclic urea compound of the formula:
  • X represents hydrogen, halogen, alkyl, or alkoxy
  • Y represents halogen, alkyl, alkoxy, alkyl which is substituted with halogen, or phenoxy
  • Z represents oxygen or sulfur
  • m represents 0 or 1
  • n represents an integer of 0 to 3.
  • the literature does not disclose a cyclic urea compound having oxygen as a ring member.
  • JP-A 151364/1996 describes a cyclic urea compound of the formula:
  • R j represents t , alkyl; R represents hydrogen or C j.4 alkyl; X represents oxygen, sulfur, or NR 3 wherein R 3 represents hydrogen or methyl; Qj represents hydrogen, C 1-6 alkyl, C 3 . 7 cycloalkyl, C 3 _ 6 alkenyl, C 3 _ 6 alkynyl, phenyl which may be substituted, naphthyl which may be substituted, or heterocyclic group which may be substituted; Q 2 represents C ⁇ _ 6 alkyl, C 3 . 7 cycloalkyl, C 3 .
  • a cyclic urea or thiourea compound comprising (i) a group of the formula:
  • the present invention relates to: [1] a cyclic urea or thiourea compound comprising (i) a group of the formula:
  • Q represents an aromatic ring group which may optionally be substituted; and R and R are the same or different and each 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, as a substituent on one of the ring-forming nitrogen atoms, (ii) a group bonded through a carbon atom, a nitrogen atom or an oxygen atom as a substituent on the other ring-forming nitrogen atom, and (iii) oxygen atom as a further ring member (hereinafter referred to as "compound (la)”), or a salt thereof,
  • Q represents an aromatic ring group which may optionally be substituted
  • Q represents an optionally substituted aromatic ring group, an optionally substituted aliphatic heterocyclic group or an optionally substituted aliphatic hydrocarbon group
  • a and B are the same or different and each represents a single bond or a bivalent hydrocarbon group which may optionally be substituted
  • R and R are the same or different and each 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
  • W represents 0 or S, provided that both of A and B do not represent a single bond; or a salt thereof, [3] the compound as described in [2] above, wherein Q and Q are the same or different and each represents a C 6 _ 14 aryl group which may optionally be substituted, [4] the compound as described in [3] above, wherein said C 6-14 aryl group is phenyl, [5] the compound as described in [
  • C 6-l _, aryl group, 5- or 6-membered aromatic heterocyclic group or condensed ring may optionally be substituted with one to four substituents selected from the group consisting of hydroxy, amino, cyano, sulfamoyl, sulfamoyloxy , mercapto, nitro, halogen, sulfo and an organic residue selected from the group consisting of (1) a hydrocarbon group selected from the group consisting of a C 1-i6 alkyl group, a C 3- cycloalkyl group, a C 2 . 6 alkenyl group, a C 3-14 cycloalkenyl group, a C 2 _ 6 alkynyl group, a C 6 .
  • each group may has one to three substituents selected from the group consisting of a C 1-4 alkylthio group, halogen, a C ⁇ _ 6 alkoxy group, nitro, a C j .
  • each group may has one to five substituents selected from the group consisting of (i) a C 1-6 alkyl group, (ii) a C 2 . 6 alkenyl group, (iii) a C 2.6 alkynyl group, (iv) a C ⁇ alkoxy group, (v) an acyl group selected from the group consisting of a C-_ 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, and a C 7 _ 19 aralkyloxycarbonyl group, (vi) nitro, (vii) amino, (viii) hydroxy, (ix) cyano, (x) sulfa oyl, (xi) ercapto, (xii) halogen and (xiii) a C../, alkylthio group,
  • 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 C 1-6 alkyl group, (ii) a C 2 _ 6 alkenyl group, (iii) a C 2 _ 6 alkynyl group, (iv) a C ⁇ alkoxy group, (v) an acyl group selected from the group consisting of a C ⁇ _ 7 alkanoyl group, a C 6 .
  • an acyl group selected from the group consisting of a C L _ 7 alkanoyl group, a C 6 . Kl aryl-carbonyl group, a C 6 alkoxy-carbonyl group, a C 6 . 14 aryloxy-carbonyl group, a C 7 .
  • each group may has one to three substituent or substituents selected from the group consisting of a C ⁇ alkylthio group, halogen, a C._ 6 alkoxy group, nitro, a C ⁇ alkoxy-carbonyl group, a mono- or di-C- ⁇ alkylamino group, a Cj.
  • each group may has one to five substituents selected from the group consisting of (i) a C 1-6 alkyl group, (ii) a C 2 .
  • 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,
  • 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 )
  • a carba oyloxy 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),
  • Q represents (a) an aromatic ring group as defined above for Q , (b) a 4- to 6- membered aliphatic heterocyclic group which may optionally be substituted with one to four substituents selected from the group consisting of hydroxy, amino, cyano, sulfamoyl, sulfa oyloxy, mercapto, nitro, halogen, an organic residue selected from the group consisting of a hydrocarbon group as defined in above (1), a 3- to 8- membered heterocyclic group or a condensed ring group thereof with benzene ring or a 3- to 8-membered heterocyclic ring as defined in above (2) and an acyl group as defined in above (3) for Q , sulfo, oxo, thioxo and a C ⁇ _ 6 alkylidene;
  • an aliphatic hydrocarbon group selected from the group consisting of a C ⁇ alkyl group, a C 2 . 6 alkenyl group, a C 2 . 6 alkynyl group, a C 3 . 14 cycloalkyl group and a C 3 .
  • cycloalkenyl group which may optionally be substituted with one to four substituents selected from the group consisting of hydroxy, amino, cyano, sulfamoyl, sulfamoyloxy, mercapto, nitro, halogen, an organic residue selected from the group consisting of a hydrocarbon group as defined in above (1), a 3- to 8-membered heterocyclic group or a condensed ring group thereof with benzene ring or a 3- to 8-membered heterocyclic ring as defined in above (2) and an acyl group as defined in above (3) for Q , sulfo, oxo, thioxo and a C 1-6 alkylidene group;
  • a and B are the same or different and each represents a single bond or a bivalent hydrocarbon group selected from the group consisting of a C 1-6 alkylene group, a C j . 6 alkenylene group and a phenylene group, each of which may substituted with one to four substituents selected from the group consisting of hydroxy, amino, cyano, sulfamoyl, sulfamoyloxy , mercapto, nitro, halogen, an organic residue selected from the group consisting of a hydrocarbon group as defined in above (1), a 3- to 8-membered heterocyclic group or a condensed ring group thereof with benzene ring or a 3- to 8-membered heterocyclic ring as defined in above (2) and an acyl group as defined in above (3) for Q , sulfo, oxo and thioxo, provided that both of A and B do not represent a single bond;
  • R and R are the same or different and each represents a hydrocarbon group selected from the group consisting of a Cj. 6 alkyl group, a C 3 . 14 cycloalkyl group, a C 2-6 alkenyl group, a C 3 . 14 cycloalkenyl group, a C 2 . 6 alkynyl group, a C 6 . aryl group and a C 7- ⁇ 9 aralkyl group and each of which may optionally be substituted with one to four substituents selected from the group consisting of hydroxy, amino, cyano, nitro, and halogen, or R ⁇ and R ? may form a ring of C 3 .
  • each of said cycloalkane and cycloalkene may optionally be substituted with one to four substituents selected from the group consisting of hydroxy, amino, cyano, nitro, and halogen; W represents 0 or S; or a salt thereof,
  • Q ' represents (1) a C 6 . u aryl group which may optionally be substituted with one to four substituents selected from the group consisting of halogen and halo-C ⁇ alkyl or (2) a 5- or 6- membered aromatic heterocyclic group or a condensed ring group thereof with benzene ring or a 5- or 6- membered aromatic heterocyclic ring, which may optionally be substituted with one to four halogens;
  • Q represents (1) a C 6 . 14 aryl group which may optionally be substituted with one to four substituents selected from the group consisting of (i) a C ⁇ alkyl group which may optionally be substituted with one to three halogens, (ii) halogen, (iii) a C[. 6 alkoxy group, (iv) cyano and (v) nitro, (2) a C 3 .
  • Q represents (1) phenyl which may optionally be substituted with one to three substituents selected from the group consisting of (i) a C 6 alkyl group which may optionally be substituted with 1 to 3 halogens, (ii) halogen, (iii) a C 1-i6 alkoxy group, (iv) cyano and (v) nitro, (2) a C 3 _ 7 cycloalkyl group, (3) a C 3 .
  • a and B are the same or different and each represents a single bond, a C ⁇ alkylene group which may optionally be substituted with an oxo group or a C 2 _ 6 alkenylene group which may optionally be substituted with 1 or 2 C,_ 6 alkyl groups, provided that both of A and B do not represent a single bond;
  • R 1 and R2 are the same or different and each represents a C 1-6 alkyl group
  • W represents 0 or S; or a salt thereof,
  • Y represents hydrogen or a lower alkyl group, and the other symbols have the same meanings as defined in [2] above, or a salt thereof with a compound of the formula :
  • R and R are the same or different and each represents hydrogen or a hydrocarbon group which may optionally be substituted or a salt thereof to provide a compound of the formula:
  • R and R are as defined above; the other symbols have the same meanings as defined in [2] above, or a salt thereof;
  • R and R are as defined above; the other symbols have the same meanings as defined in [2] above, or a salt thereof; or
  • the present invention relates to:
  • Q represents an optionally substituted aromatic ring group, an optionally substituted aliphatic heterocyclic group or an optionally substituted aliphatic hydrocarbon group
  • A represents a single bond or a bivalent hydrocarbon group which may optionally be substituted
  • B represents a bivalent hydrocarbon group which may optionally be substituted
  • R 1 and R2 are the same or different and each 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
  • W represents 0 or S, or a salt thereof, [21] the compound as described in [2] above, wherein Q represents an aromatic ring group which may
  • Q represents an optionally substituted aromatic ring group, an optionally substituted aliphatic heterocyclic group or an optionally substituted aliphatic hydrocarbon group
  • A represents methylmethylene, dimethylmethylene, propylene, vinylene, carbonyl or carbonyl-C 1-2 alkyl
  • B represents a single bond
  • R and R are the same or different and each 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
  • A represents a C 1-6 alkylene group which may optionally be substituted with an oxo group or a C 2 . 6 alkenylene group which may optionally be substituted with 1 to 2 C 1-6 alkyl groups
  • B represents a single bond
  • R 1 and R2 are the same or different and each represents a C ⁇ _ 6 alkyl group
  • W represents 0 or S , or a salt thereof
  • the compound (Ia) of the invention has the following three structural features. (1)
  • the compound (Ia) has a group of formula (I')
  • the compound (la) has a group bonded through a carbon atom, a nitrogen atom or an oxygen atom on the other ring-forming nitrogen atom.
  • the compound (Ia) has oxygen as a ring member.
  • 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 includes C 6 _ 14 aryl such as phenyl, 1- or 2-naphthyl, 1-, 2-, or 5-anthranyl, etc.
  • the 5- or 6-membered aromatic heterocyclic group or its condensed ring group includes pyrrolyl (e.g. 1-, 2-, or 3- ⁇ yrrolyl), 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, 1 , 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, indolyl (e.g. 3H-indol-2-, 3-, 4-, 5-, 6- or 7-yl), quinolyl (e.g.
  • thieno[2,3- d]pyridin-3-yl ) thieno[2,3- d]pyridin-3-yl
  • 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.
  • 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,
  • 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
  • hydrocarbon group, heterocyclic group, and acyl group for the above-mentioned organic residue, the hydrocarbon group, heterocyclic group, and acyl group for Q°, and the hydrocarbon group and acyl group for Q or Q will be described in detail hereinafter.
  • carbamoyl, carbamoyloxy, and thiocarbamoyl may respectively be substituted by 1 or 2 substituents selected from the group consisting of the hydrocarbon group, heterocyclic group, and acyl group which will be described in detail hereinafter.
  • the above-mentioned ureido may be substituted by 1 to 3 substituents selected form the group consisting of the hydrocarbon group, heterocyclic group, and acyl group which will be described in detail hereinafter.
  • 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 C 1-19 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, 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-C,_ 4 alkyl such as benzyl, phenethyl , phenylpropyl; benzhydryl, and trityl.
  • hydrocarbon group is an alkyl group, an alkenyl group or an alkynyl group
  • said hydrocarbon group may optionally be substituted by 1 to 3 substituents selected from the group consisting of an alkylthio group (e.g. C 4 alkylthio such as ethylthio, ethylthio, n-propylthio, isopropylthio, etc.), halogen (e.g. fluorine, chlorine, bromine, iodine), an alkoxy group (e.g.
  • an alkylthio group e.g. C 4 alkylthio such as ethylthio, ethylthio, n-propylthio, isopropylthio, etc.
  • halogen e.g. fluorine, chlorine, bromine, iodine
  • an alkoxy group e.g.
  • C 1-6 alkoxy such as methoxy, ethoxy, n-propoxy, tert-butoxy, n-hexyloxy, etc.
  • an alkoxy-carbonyl group e.g. C ⁇ _ fi alkoxy-carbonyl such as methoxycarbonyl , ethoxycarbonyl, n-propoxycarbonyl , isopropoxycarbonyl , n-butoxycarbonyl, isobutoxycarbonyl, sec- butoxycarbonyl , tert-butoxycarbonyl , etc.
  • an alkyla ino group e.g.
  • mono- or di-C 1-6 alkylamino such as methylamino, ethylamino, n-propylamino, n- butylamino, tert-butylamino, n-pentylamino, n- hexyla ino, dimethylamino, diethylamino, methylethylamino, di-(n-propyl ) amino, di-(n- butyl)amino, etc.], an alkoxyi ino group (e.g. C j .
  • alkoxyimino such as methoxyimino, ethoxyimino, n- propoxyimino , tert-butoxyimino, n-hexyloxy-imino, etc.
  • hydroxyimino such as methoxyimino, ethoxyimino, n- propoxyimino , tert-butoxyimino, n-hexyloxy-imino, etc.
  • 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 1 . 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 1 . 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 . ft alkynyl such as propargyl, 2-butynyl, 3-butynyl, 3- pentynyl, 3-hexynyl, etc.
  • an alkoxy group e.g.
  • C ⁇ _ 6 alkoxy such as methoxy, ethoxy, n-propoxy, tert-butoxy, n-hexyloxy, etc.
  • an acyl group e.g. C,_ 7 alkanoyl such as for yl, acetyl, propionyl , butyryl, isobutyryl, pentanoyl, hexanoyl, heptanoyl , etc.; C 6 . 14 aryl- carbonyl such as benzoyl, naphthalenecarbonyl , etc.; C- . ..
  • alkoxy-carbonyl such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl , tert-butoxycarbonyl, etc.; C 6 . 14 aryloxy-carbonyl such as phenoxycarbonyl , etc.; C 7 . 19 aralkyl-carbonyl such as phenyl-Cj. 4 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. Cj. 4 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 heteroatoms 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.
  • 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
  • thio orpholinyl quinolyl (e.g. 2-, 3-, 4-, 5-, 6-, 7-, or 8-quinolyl)
  • isoquinolyl pyrido [ 2 , 3-d ]pyrimidinyl
  • pyridof 2 , 3-d]pyrimidin-2-yl naphthyridinyl such as 1,5-, 1,6-, 1,7-, 1,8-, 2,6-, or 2 , 7-naphthyridinyl (e.g. l,5-naphthyridin-2- or 3-yl), thieno[2,3- d]pyridyl (e.g. thieno[2 , 3-d]pyridin-3-yl) , pyrazinoquinolyl (e.g. pyrazino[ 2 , 3-d]quinolin-2-yl ) , chromenyl (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 1-6 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 2-6 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. C 1-i6 alkoxy such as methoxy, ethoxy, n-propoxy, tert-butoxy, n-hexyloxy, etc.
  • an acyl group [e.g. ⁇ .
  • alkanoyl such as formyl , acetyl, propionyl , butyryl, isobutyryl, pentanoyl, hexanoyl , heptanoyl, etc.
  • C. 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 .
  • 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. C ⁇ alkylthio group such as methylthio, ethylthio, n-propylthio , isobutylthio , etc. ) .
  • alkylthio group e.g. C ⁇ alkylthio
  • the acyl group as used throughout this specification includes an acyl group of 1 to 20 carbon atoms, which is derived from any organic carboxylie acid. Specifically, mention can be made of an alkanoyl group, preferably a C ⁇ _ 7 alkanoyl group (e.g. for yl, acetyl, propionyl , butyryl , isobutyryl, pentanoyl , hexanoyl , heptanoyl, etc.), an arylcarbonyl group, preferably a C 6 . 14 aryl-carbonyl group (e.g.
  • alkoxycarbonyl group preferably a C ⁇ alkoxy-carbonyl group (e.g. methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl , isopropoxycarbonyl, butoxycarbonyl , isobutoxycarbonyl, sec-butoxycarbonyl , tert-butoxycarbonyl, etc.), an aryloxycarbonyl group, preferably a C 6 . 14 aryloxy- carbonyl group (e.g phenoxycarbonyl etc.), an aralkylcarbonyl group, preferably a C 7 . 19 aralkyl- carbonyl group (e.g.
  • phenyl-C- ⁇ alkylcarbonyl such as benzylcarbonyl , phenethylcarbonyl , phenylpropylcarbonyl ; benzhydrylcarbonyl ; naphthyl-Ci.,, 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.
  • a 5- or 6-membered heterocyclic-carbonyl group having 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) such as 5- or 6-membered heterocyclic- carbonyl or condensed heterocycle-carbonyl (e.g.
  • pyrrolylcarbonyl such as 2-, 3-, or 4-pyrrolylcarbonyl
  • pyrazolylcarbonyl such as 3-, 4-, or 5- pyrazolylcarbonyl
  • 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 1H- 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 an alkylthio group (e.g. C 1-4 alkylthio such as methylthio, ethylthio, n-propylthio, isopropylthio, etc.), halogen (e.g. fluorine, chlorine, bromine, iodine), an alkoxy group (e.g.
  • an alkylthio group e.g. C 1-4 alkylthio such as methylthio, ethylthio, n-propylthio, isopropylthio, etc.
  • halogen e.g. fluorine, chlorine, bromine, iodine
  • an alkoxy group e.g.
  • C _ 6 alkoxy such as methoxy, ethoxy, n-propoxy, tert-butoxy, n-hexyloxy, etc.
  • an alkoxy-carbonyl group e.g. C J-5 alkoxy-carbonyl such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl , isopropoxycarbonyl, n-butoxycarbonyl , isobutoxycarbonyl, sec- butoxycarbonyl , tert-butoxycarbonyl, etc.
  • an alkylamino group e.g.
  • mono- or di-C 1-6 alkylamino such as methylamino, ethyla ino, 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.
  • 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 heterocyclic-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 5 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 2-6 alkenyl such as allyl, isopropenyl, isobutenyl, 1-methylallyl , 2- pentenyl, 2-hexenyl, etc.
  • an alkynyl group e.g. C 2 - fi alkynyl such as propargyl, 2-butynyl, 3-butynyl, 3- pentynyl, 3-hexynyl, etc.
  • an alkoxy group e.g. C,_ 6 alkoxy such as methoxy, ethoxy, n-propoxy, tert-butoxy, n-hexyloxy, etc.
  • an acyl group e.g.
  • C 1-7 alkanoyl such as formyl, acetyl, propionyl, butyryl, isobutyryl, pentanoyl, hexanoyl , heptanoyl, etc.
  • C 6 ., 4 aryl- carbonyl such as benzoyl, naphthalenecarbonyl , etc.
  • C 1-6 alkoxy-carbonyl such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl , isopropoxycarbonyl, butoxycarbonyl , isobutoxycarbonyl, sec-butoxycarbonyl , tert-butoxycarbonyl, etc.
  • C 6.14 aryloxy-carbonyl such as phenoxycarbonyl , etc.
  • C 7-19 aralkyl-carbonyl such as phenyl-C 1-i4 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. C,_ 4 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 alkylsulf inyl 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 1-5 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 1-5 alkoxy or C 3-6 cycloalkyloxy such as methoxy, ethoxy, n-propoxy, isopropoxy, n- butoxy, isobutoxy, sec-butoxy, tert-butoxy, n- pentyloxy, sec-pentyloxy
  • the alkenyloxy group mentioned above is preferably a straight-chain, branched, or cyclic alkenyloxy group of 2 to 6 carbon atoms, such as allyloxy, isopropenyloxy, 1-butenyloxy, 2-pentenyloxy, 2- hexenyloxy, 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 phenyl-C ⁇ 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; imidazolyloxy 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 1H- 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-thienyloxy-l , 1-dioxide; 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 ⁇ 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 . 14 arylcarbonyloxy such as benzoyloxy and naphthoyloxy; heterocycle-carbonyloxy such as thienylcarbonyloxy and benzothienylcarbonyloxy , etc.
  • the alkylthio group mentioned above is preferably a straight-chain, branched, or cyclic C 1-i6 alkylthio group, e.g. C l . 6 alkylthio and C 3-6 cycloalkylthio such as methylthio, ethylthio, n-propylthio, isopropyl thio , n-butylthio, isobutylthio, sec-butylthio, tert- butylthio, n-pentylthio, sec-pentylthio, isopentylthio, neopentylthio, cyclopentylthio, n-hexylthio, isohexylthio, cyclohexylthio, etc.
  • C 1-i6 alkylthio group e.g. C l . 6 alkylthio and C 3-6 cycloalkylthio such as
  • alkenylthio group mentioned above is preferably a straight-chain, branched, or cyclic C 2 . 6 alkenylthio group 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,. 4 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; imidazolylthio 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 1H- 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-thienylthio-l, 1-dioxide; and oxazolyl
  • the acylthio group mentioned above is a group of the formula T"-S- wherein T" represents above-mentioned acyl group, specifically including C 1-6 alkyl- carbonylthio such as acetylthio, propionylthio, butyrylthio, pentanoylthio, and hexanoylthio ; phenyl- C,_ 4 alkylcarbonylthio such as benzylcarbonylthio and phenethylcarbonylthio; C 6 . 14 arylcarbonylthio such as benzoylthio, and naphthoylthio; heterocycle- carbonylthio such as thienylcarbonylthio and benzothienylcarbonylthio, etc.
  • C 1-6 alkyl- carbonylthio such as acetylthio, propionylthio, butyrylthio, pentanoylthio, and hexan
  • alkyldithio group mentioned above is preferably a straight-chain, branched, or cyclic C,_ 5 alkyldithio group, e.g. C 1-6 alkyldithio or C 3-6 cycloalkyldithio such as methyldithio , ethyldithio, n- propyldithio, cyclopentyldithio, etc.
  • the aryldithio group mentioned above is preferably a C 5 . 14 aryldithio group such as phenyldithio, naphthyldithio, etc.
  • the aralkyldithio group mentioned above is preferably a C 7 . 19 aralkyldithio group e.g. phenyl-C, . _, alkyldithio such as benzyldithio, phenethyldithio , etc.
  • the alkylsulfinyl group mentioned above is preferably a straight-chain, branched, or cyclic C,_ 6 alkylsulfinyl group, e.g.
  • alkylsulfinyl or C 3.6 cycloalkylsul inyl 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 . 5 alkenylsulfinyl group 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 benzyl ⁇ ulfinyl .
  • 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-, 5- pyrazolylsulfinyl , etc.
  • the alkylsulfonyl group mentioned above is preferably a straight-chain, branched, or cyclic C, ⁇ alkylsulfonyl group, e.g. C, redesign 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 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-C,. 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.
  • an alkylamino group preferably a mono- or di-(C,. 6 alkyl)amino group, e.g. methylamino, ethylamino, n-propy.lamino, n-butylamino, tert-butylamino, n-pentylamino, n-hexylamino, dimethyla ino, diethylamino, methylethyla ino, 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.
  • cyclopropylamino cyclopentylamino , cyclohexylamino , dicyclohexylamino, etc.
  • an arylamino group preferably a C 6-
  • an aralkyla ino group preferably a C 7-19 aralkylamino group, e.g. phenyl-C,.
  • alkylamino such as benzylamino, 1-phenylethylamino , benzhydrylamino , tritylamino, etc.
  • an acylamino group i.e. a group of the formula T"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 6- arylcarbonylamino group, and a heterocycle-carbonylamino group wherein the alkyl, aryl, and heterocyclic group of the heterocycle- carbonyla ino are preferably those mentioned in the substituent of the aromatic ring group for Q I thus specifically including acetamido, propionamido, butyryla ino, pentanoyla ino, he
  • 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 mono- or di-alkylsulfamoyl group preferably a mono- or 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 .,
  • arylsulfamoyl group e.g. phenylsulfamoyl etc.
  • an aralkylsulfamoyl group preferably a C 7 . 19 aralkylsulfamoyl group, e.g. phenyl-C,.
  • alkylsulfamoyl such as benzylsulfamoyl ; benzhydrylsulfamoyl , tritylsulfamoyl , etc.
  • 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,_ 4 alkylcarbonylsulfamoyl such as benzylcarbonylsulfamoyl, heterocycle -carbonylsulfamoyl such as thienylcarbonylsulfamoyl, etc.
  • Q and Q' may form a ring together with the adjacent nitrogen atom, e.g. pyrrolidino, morpholino, thiomorpholino, 1- piperidinyl, aziridino, azetidino, etc.
  • the group of the formula Q A -S0 2 -0- specifically includes (1) an alkylsulfonyloxy group, preferably a C,_ 6 alkylsulfonyloxy group, e.g. methanesulfonyloxy, ethanesulfonyloxy, etc., (2) an arylsulfonyloxy group, preferably a C 6 . 14 arylsulfonyloxy group, e.g. benzenesulfonyloxy, etc., (3) an aralkylsulfonyloxy group, preferably a C 7 . 19 aralkylsulfonyloxy group, e.g.
  • phenyl-C ⁇ alkylsulfonyloxy such as benzylsulfonyloxy , phenethylsulfonyloxy, etc.
  • an acylsulfonyloxy group e.g. C,_ 6 alkylcarbonylsulfonyloxy such as acetylsulfonyloxy, butyrylsulfonyloxy, etc.
  • R 1 and R2 are the same or different and each represents 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.
  • the hydrocarbon group and its substituent or substituents mentioned just above includes those mentioned hereinbefore.
  • the ring formed by R 1 and R2 together with the adjacent carbon atom and which may optionally be substituted includes C 3 . 7 cycloalkanes , e.g. cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, etc. and C 3.7 cycloalkenes , e.g. cyclopropene, 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 R2.
  • C 3 . 7 cycloalkanes e.g. cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, etc.
  • C 3.7 cycloalkenes e.g. cyclopropene,
  • the group bonded through a carbon atom which is present as a substituent on one of nitrogen atoms of compound (la) 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, 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 1 .
  • the carbamoyl group may have 1 or 2 substituents, and the amidino group may have 1 to 3 substituents.
  • the substituents for said carbamoyl 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 raono- 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-, 4- perhydroazepinyl
  • perhydroazocinyl e.g. 2-, 3-, 4-, 5-perhydroazocinyl
  • 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. 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.
  • 1, 2,4-oxadiazol-3- or 5-yl 1, 2,4-oxadiazol-3- or 5-yl
  • oxadiazolyl e.g. 1,3,4- oxadiazolyl
  • thiadiazolyl e.g. 1, 2 , 4-thiadiazol-3- or 5-yl, 1, 3,4-thiadiazolyl, 1, 2 , 3-thiadiazol-4- or 5-yl, 1,2,5-thiadiazolyl
  • triazolyl e.g. 1 , 2 , 3-triazolyl , l,2,4-triazol-3- or 5-yl
  • tetrazolyl e.g. 1H- or 2H- tetrazol-5-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-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.
  • piperidinyl e.g. 2- or 3-piperidinyl
  • pyranyl e.g. 2- or 3-pyranyl
  • thiopyranyl e.g. 2- or 3- thiopyranyl
  • oxazinyl e.g. 1 , 4-oxazin-2- or 3-yl
  • thiazinyl e.g. 1 , 4-thiazin-2- or 3-yl
  • thiazinyl e.g. 1, 3-thiazinyl
  • piperazinyl e.g. 2- or 3- piperazinyl
  • pyridazinyl e.g.
  • 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 6 alkoxy-carbonyl group (e.g. methoxycarbonyl, ethoxycarbonyl, etc.), (9) sulfo, (10) halogen (e.g. fluorine, chlorine, bromine, iodine),
  • a C 1 _ 6 alkoxy group e.g. methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, etc.
  • 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- , -, or p-chlorophenoxy, o-, m-, or p- bromophenoxy, etc.
  • a C ⁇ alkylthio group e.g.
  • 6 alkylcarbonylamino group e.g. acetylamino, propionylamino, etc.
  • 6 alkylamino group e.g. methylamino, ethylamino, n- propylamino, isopropylamino, n-butylamino, dimethylamino , diethylamino, etc.
  • (21) imino (22) a Ci.s alkylimino group (e.g. methylimino, ethyl imino, propylimino, butylimino, etc.), (23) hydroxyimino, (24) a Ci.
  • halogen e.g. fluorine, chlorine, bromine, iodine
  • a C,_ 4 alkyl group e.g. methyl, ethyl, propyl , isopropyl, etc.
  • halophenoxy e.g. phenoxy which is substituted by 1 to 3 halogens such as o-, -, 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-imid
  • the group bonded through a nitrogen atom which is present as a substituent on one of the nitrogen atoms of compound (la) is not particulary limited but can be any group which is bonded through a nitrogen atom.
  • there can be used any of (1) nitro, (2) a group of the formula -NR R wherein each of R and R represents hydrogen, a hydrocarbon group which may optionally be substituted, an acyl group which may optionally be substituted, a heterocyclic group which may optionally be substituted, hydroxy, or a group of the formula -SO p R wherein R represents hydrogen or hydrocarbon group which may optionally be substituted; p represents 1 or 2, (3) a heterocyclic group bonded through a nitrogen atom, which may optionally be substituted, and (4) a group of the formula -N C(R a )R 9
  • R and R are the same or different and each represents hydrogen, a hydrocarbon group which may optionally be substituted, a heterocyclic group which may optionally be substituted, a hydrocarbon-oxy group which may optionally be substituted, or a group of the formula -NR R wherein R and R each represents hydrogen or a hydrocarbon group which may optionally be substituted .
  • the hydrocarbon group which may optionally be substituted as mentioned for R , R 6 , R , R 8 , R 9 , R 10 , 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 1 .
  • the optionally substituted hydrocarbon group of the hydrocarbon-oxy group which may 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 or R includes the same acyl 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 , R , R , or R includes the same 3- to 8-membered heterocyclic group which contains 1 to 4 heteroatoms 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 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, 2H-tetrazol-2-yl , 1-piperidinyl , 4-thiomorpholinyl , 4- morpholinyl, 1-dihydropyridyl , 1-tetrahydropyridyl , 2- or 4-oxodihydropyridin-l-yl, 1-tetrahydropyrimidyl , 1- perhydropyri idyl ,
  • the group bonded through an oxygen atom which is present as a substituent on one of the nitrogen atoms of compound (Ia) is not particularly limited but can be any group which is bonded through an oxygen atom.
  • it may for example be a group of the formula - OR wherein 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, or (5) -SiR 3 wherein
  • R 13 represents a hydrocarbon group which may optionally be substituted.
  • 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 or R .
  • the acyl group for R includes the same acyl group as mentioned for the substituent of the aromatic ring group for Q .
  • the number of oxygen as a ring member in compound (la) is preferably one.
  • the compound (Ia) includes both cyclic urea compounds and cyclic thiourea compounds.
  • Compound (la) is preferably a compound of the following formula (I), or a salt thereof (hereinafter referred to as “compound (I ) " );
  • Q represents an optionally substituted aromatic ring group, an optionally substituted aliphatic heterocyclic group or an optionally substituted aliphatic hydrocarbon group
  • a and B are the same or different and each represents a single bond or a bivalent hydrocarbon group which may optionally be substituted, provided that both of A and B do not represent a single bond
  • W represents O or S; the other symbols have the same meanings as defined hereinbefore.
  • the optionally substituted aromatic ring group as mentioned for Q 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 for Q 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 for Q includes a straight-chain or branched C,_ hydrocarbon group and an alicyclic C 3 . 14 hydrocarbon group .
  • the above-mentioned straight-chain or branched aliphatic hydrocarbon group includes a C,. 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 . 6 alkenyl group such as allyl, isopropenyl, isobutenyl, 2-pentenyl, 2-hexenyl, etc., and 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 . 14 cycloalkyl group, preferably C 3-7 cycloalkyl group such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, perhydronaphthyl , perhydro- anthranyl, bicyclof 2.2.1 ]heptyl , etc. and C 3 ., 4 cyclo- alkenyl 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 . 14 cycloalkyl group preferably C 3-7 cycloalkyl group such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, perhydron
  • the aliphatic heterocyclic group and aliphatic hydrocarbon group may respectively have 1 to 4 substituents, for example, hydroxy, amino, cyano, sulfamoyl, sulfamoyloxy , mercapto, nitro, halogen, organic residue, sulfo, oxo, thioxo, and a C,_ 6 alkylidene group.
  • substituents for example, hydroxy, amino, cyano, sulfamoyl, sulfamoyloxy , mercapto, nitro, halogen, organic residue, sulfo, oxo, thioxo, and a C,_ 6 alkylidene group.
  • the above-mentioned halogen and organic residue have the same meaning as defined in substituent of the aromatic ring group for Q 1 as mentioned above.
  • the bivalent hydrocarbon group mentioned for A and B includes an alkylene group, an alkenylene group, and phenylene. Preferred are an alkylene group and an alkenylene group.
  • the above-mentioned alkylene group is preferably a straight-chain or cyclic C,_ 6 alkylene group such as methylene, methylmethylene, dimethylmethylene, ethylene, propylene, trimethylene, tetramethylene , pentamethylene, hexamethylene , cyclopropylene, 1,2- cyclobutylene, 1 , 3-cyclobutylene, cyclopentylene, 1,3- cyclopentylene, cyclohexylene, 1 , 3-cyclohexylene , 1,4- cyclohexylene, etc.
  • C,_ 6 alkylene group such as methylene, methylmethylene, dimethylmethylene, ethylene, propylene, trimethylene, tetramethylene , pentamethylene, hexamethylene , cyclopropylene, 1,2- cyclobutylene, 1 , 3-cyclobutylene, cyclopentylene, 1,3- cyclopentylene, cycl
  • alkenylene group is preferably a straight-chain, branched, or cyclic alkenylene group of 1 to 6 carbon atoms, such as vinylene, propenylene, 1-propen-l , 2-ylene , 2-propen-l , 2-ylene , butenylene (e,g, 1-buten-l, 4-ylene, 2-buten- 1 , 4-ylene , etc.), pentenylene (e.g. 1-penten-l , 5-ylene , 2-penten-l , 5- ylene, etc.), hexenylene (e.g.
  • cyclopropenylene e.g. 1-cyclopropen-l , 2-ylene, 2- cyclopropen-1, 2-ylene
  • cyclobutenylene e.g. 1- cyclobuten-1 , 2-ylene, 1-cyclobuten-l , 3-ylene, 2- cyclobuten-l,2-ylene, 3-cyclobuten-l, 2-ylene
  • cyclopentenylene e.g.
  • the phenylene mentioned above includes o- phenylene, m-phenylene, and p-phenylene.
  • the bivalent hydrocarbon group for A and B may have 1 to 4 substituents which is the same or different, as selected from for example, hydroxy, amino, cyano, sulfamoyl, sulfamoyloxy , mercapto, nitro, halogen, organic residue, sulfo, oxo, and thioxo.
  • the above-mentioned halogen includes fluorine, chlorine, bromine, and iodine.
  • the organic residue includes the same groups mentioned for the substituent of the aromatic ring group for Q .
  • a and B each represents a single bond, a C,_ 6 alkylene group which may optionally be substituted, or a C 2 . 6 alkenylene group, and both of A and B do not represent a single bond.
  • B is preferably a bivalent hydrocarbon residue which may optionally be substituted.
  • the preferable substituent for above-mentioned C. .6 alkylene group is oxo.
  • the preferable substituent for above-mentioned C 2-6 alkenylene group is C,_ 6 alkyl, especially methyl.
  • the number of substituent is 1 to 3, preferably 1 to 2. represents 0 or S .
  • 14 aryl group which may optionally be substituted with one to four substituents selected from the group consisting of (i) a C,_ 6 alkyl group which may optionally be substituted with one to three halogens, (ii) halogen, (iii) a C,_ 6 alkoxy group, ( iv ) cyano and (v) nitro, (2) a C 3 . 14 cycloalkyl group, (3) a C 3 .
  • a and B are the same or different and each represents a single bond, a C,_ 6 alkylene group which may optionally be substituted with oxo or a C 2 .
  • R 1 and R 2 are the same or different and each represents a C 1-5 alkyl group
  • W represents 0 or S; or a salt thereof, (2) the compound (I) as described in (1) above, wherein Q represents (1) phenyl which may optionally be substituted with one or two substituents selected from the group consisting of halogen and tri-halo-C, ⁇ alkyl or (2) pyridyl (e.g. 2-, 3- or 4- pyridyl) which may optionally be substituted with a halogen, furyl (e.g.
  • thienyl e.g. 2- or 3-furyl
  • thienyl e.g. 2- or 3- thienyl
  • imidazof 1 2-a]pyridyl
  • 2-a]pyridyl e.g. 2-, 3-, 5-, 6-, 7- or 8- imidazo[ 1 , 2-a]pyridyl
  • halogen e.g. 2-, 3-, 5-, 6-, 7- or 8- imidazo[ 1 , 2-a]pyridyl
  • Q 2 represents (1) phenyl which may optionally be substituted with one to three substituents selected from the group consisting of (i) a C,_ 6 alkyl group which may optionally be substituted with 1 to 3 halogens, (ii) halogen, (iii) a C,_ alkoxy group, (iv) cyano and (v) nitro, (2) a C 3 . 7 cycloalkyl group, (3) a C 3 . 7 cycloalkenyl group, (4) thienyl (e.g. 2- or 3- thienyl), (5) thiazolyl (e.g. 2 - , 4- or 5-thiazolyl ) , (6) pyridyl (e.g.
  • 2-, 3- or 4-pyridyl (7) imidazof 1, 2-a]pyridyl (e.g. 2-, 3-, 5-, 6-, 7- or 8- imidazo[ 1 , 2-a]pyridyl ) , (8) pyrrolidinyl (e.g. 1-, 2- or 3-pyrrolidinyl ) which may optionally be substituted with a phenyl group, (9) piperidyl (e.g. 1-, 2-, 3- or 4-piperidyl) which may optionally be substituted with a C,. 6 alkoxy-carbonyl group, (10) pyrrolyl (e.g. 1-, 2- or 3-pyrrolyl), (11) tetrahydrofuryl (e.g.
  • tetrahydro- 2- or 3-furyl which may optionally be substituted with an oxo group, (12) morpholinyl (e.g. 2-, 3- or 4- morpholinyl) ,( 13) benzyl or (14) a C,_ 6 alkyl group;
  • a and B are the same or different and each represents a single bond, a C 1-6 alkylene group which may optionally be substituted with an oxo group or a C 2 . 6 alkenylene group which may optionally be substituted with 1 or 2 C,. 6 alkyl groups, provided that both of A and B do not represent a single bond;
  • R and R are the same or different and each represents a C,. 6 alkyl group; W represents O or S; or a salt thereof,
  • Q represents an optionally substituted aromatic ring group, an optionally substituted aliphatic heterocyclic group or an optionally substituted aliphatic hydrocarbon group
  • A represents methylmethylene, dimethylmethylene, propylene, vinylene, carbonyl or carbonyl-Ci. 2 alkyl
  • B represents a single bond
  • R and R are the same or different and each represents a hydrocarbon group which may optionally be substituted or R 1 and R may form a ring together with the adjacent carbon atom wherein the ring may optionally be substituted
  • Q represents an optionally substituted aromatic heterocyclic group or an optionally substituted cyclic aliphatic hydrocarbon group
  • A represents a bivalent hydrocarbon group which may optionally be substituted
  • B represents a single bond
  • R 1 and R2 are the same or different and each 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
  • Q represents (1) a 5- or 6- membered aromatic heterocyclic group or a condensed ring group thereof with benzene ring or a 5- or 6- membered aromatic heterocyclic ring or (2) a C 3 .
  • A represents a Cj.g alkylene group which may optionally be substituted with an oxo group or a C 2 . 6 alkenylene group which may optionally be substituted with 1 or 2 C,_ 6 alkyl groups;
  • B represents a single bond;
  • R 1 and R? are the same or different and each represents a C ⁇ _ 6 alkyl group;
  • W represents 0 or S, or a salt thereof,
  • W represents 0 or S, or a salt thereof, and (10) the compound (I) as described in (8) above, wherein Q represents furyl (e.g. 2- or 3-furyl), thienyl (e.g. 2- or 3-thienyl), pyridyl (e.g. 2-, 3- or 4- pyridyl) or imidazo[ 1 , 2-a Jpyridyl (e.g.
  • the compounds of the present invention may contain acidic groups such as sulfo and carboxy in substituents, they 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. calcium etc.), and ammonia
  • the salt of compound (Ia) with an organic base includes salts with dimethylamine, triethyla ine, N,N-dimethylaniline , piperazine, pyrrolidine, piperidine, pyridine, 2-phenylethylamine, benzyla ine, ethanolamine, diethanolamine, 1,8- diazabicyclo[ 5 ,4 , 0 ] -7-undecene (hereinafter sometimes referred to briefly as DBU) .
  • alkali metals e.g. sodium, potassium, etc.
  • alkaline earth metals e.g. calcium etc.
  • the salt of compound (Ia) with an organic base includes salts with dimethylamine, triethyla ine, N,N-dimethylaniline
  • the inorganic acid addition salt of compound (Ia) includes salts with hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid, and perchloric acid and the organic acid addition salt of compound (la) includes salts with formic acid, acetic acid, propionic acid, oxalic acid, succinic acid, benzoic acid, p-toluenesulfonic acid, methanesulfonic acid, and trifluoroacetic acid.
  • the compound or a salt thereof of the present invention can be used as a highly safe agrochemical typically herbicide.
  • weeds such as those listed below
  • the list of weeds which can be controlled include paddy field weeds such as Echinochloa crus- ⁇ alli var. oryzicola, C ⁇ perus dif formis Linnaeus, Scirpus iuncoides Roxburgh var.
  • centrorubrum - Polyqonu blumei Meisner [ Persicaria blumei Gross], Portulaca oleracea Linnaeus, America kingojiga, Datura alba, Ipomoea purpurea, Xanthium strumarium. Echinochloa crus- alli var. praticola, ohkusakibi, Sorghum halepense, Cyperus rotundus Linnaeus, Avena fatua , black grass, umanochahiki , Stellaria media Villars, mustard plant, Cassia obtusifolia , Matricaria chamomilla , Commelina communis , etc.
  • 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 e ulsifiable 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.
  • 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- dimethyl formamide, 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 ( agalmatolite) powder, silicas such as diatomaceous earth, mica powder, etc.), alumina, sulfur powder, activated carbon, etc. Those materials can be used either singly or in combination.
  • 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 ( agalmatolite) powder, silicas such as diatomaceous earth, mica powder, etc.
  • silicas such as diatomaceous earth, mica powder, etc.
  • alumina alumina
  • sulfur powder
  • 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
  • TM TM aryl ethers e.g. Noigen and E-A142 (TM stands for trademark and the same applies below; Dai-ichi Kogyo Seiyaku Co. Ltd.)], polyoxyethylene aryl esters (e.g. NonalTM; Toho Chemical), alkyl sulfates (e.g. Emal 10TM,
  • TM TM salts e.g. Neogen , Neogen T , Dai-ichi Kogyo Seiyaku
  • Neopelex Kao Corporation
  • polyethylene glycol ethers e.g. Nonipol 85 , Nonipol 100 , Nonipol 160TM; Sanyo Chemical Industries, Ltd.
  • polyhydric alcohol esters e.g. Tween 20 TM, Tween 80TM; Kao Corporation
  • 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 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 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 plowland.
  • the compound or s salt thereof of the invention can be used with advantage as a preemergence soil treatment or a leaf- stem-soil treatment.
  • the herbicidal composition of the 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 , i azosulfuron, 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 [benthiocar
  • 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 (I) or (Ia) 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 (I') on one of the ring-forming nitrogen atoms and a group bonded through a carbon atom, a nitrogen atom, or an oxygen atom on the other ring-forming nitrogen atom is subjected to cyclization reaction.
  • said compound (I) or a salt thereof can be produced in accordance with the following reaction schemes 1 to 6.
  • salts of the following compounds (I), (II), (III), (IV), (V), (VI), and (VII) those of the same kinds as the salt of compound (la) described hereinbefore can be employed.
  • 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. methylsulfonylox , trifluoromethyl- sulfonyloxy, p-toluenesulfonyloxy, benzenesulfonyloxy , etc.
  • Particularly preferred is halogen, with chlorine or bromine being most advantageous .
  • compound (II) or a salt thereof and compound (III) or a salt thereof are used generally in substantially equimolar proportions. Also, the compound (III) or a salt thereof may be used in excess proportion if it does not interfere with the reaction. 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, dioxane, 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 sulfoxide (
  • phase transfer catalyst When the mixtures of such solvents does not solve each other, a phase transfer catalyst can be used.
  • the phase transfer catalyst includes trioctylmethylammonium chloride, cetyltrimethylammonium bromide, triethylbenzylammonium chloride and 18-crosn-6.
  • the base that can be used for this purpose includes organic bases such as triethylamine, tri-n- propylamine, N,N-dimethylaniline, pyridine, DBU, 1,4- 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 3 moles per mole of compound (II) 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 two-stage reaction.
  • the compound (IXa) or (IXb) or a salt thereof produced by the first-stage reaction between compound (II) or a salt thereof and compound (III) or a salt thereof may be isolated and submitted to the second-stage reaction or may be subjected to the second-stage reaction without prior isolation.
  • Reaction Scheme 2
  • 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. methylsulfonyloxy , trifluoromethyl- sulfonyloxy, p-toluenesulfonyloxy , benzenesulfonyloxy , etc.
  • Particularly preferred is halogen, with chlorine or bromine being most advantageous.
  • compound (IV) or a salt thereof and compound (V) or a salt thereof are used generally in a substantially equimolar ratio.
  • the compound (V) or a salt thereof may be used in excess proportion if it does not interfere with the reaction.
  • 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.
  • 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 3 moles per mole of compound (IV) 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 two-stage reaction.
  • the compound (Xa) or (Xb) or a salt thereof produced by the first-stage reaction between compound (IV) or a salt thereof and compound (V) or a salt thereof may be isolated and submitted to the second-stage reaction or may be subjected to the second-stage reaction without prior isolation.
  • This reaction is an addition-condensation reaction between 1 mole of compound (VII) and 2 moles of compound ( I ) .
  • reaction relative to compound (VII) or a salt thereof, generally about 2 molar equivalents to a large excess of compound (VI) or a salt thereof is used.
  • 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 an acid.
  • the acid mentioned just above includes inorganic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid, etc. and organic acids such as formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, p-toluenesulfonic acid, etc.
  • the acid can be used generally in a proportion of about 0.01 to 3 molar equivalents relative to compound (VII).
  • 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.
  • Y represents hydrogen or a lower alkyl group (preferably a C 1-6 alkyl group), and the other symbols have the same meanings as defined hereinbefore.
  • compound (II) or a salt thereof and compound (VI) or a salt thereof are used generally in substantially equimolar ratio.
  • the compound (VI) or a salt thereof may be used in excess proportion if it does not interfere with the reaction.
  • 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 an acid.
  • the acid which can be used for this purpose includes the same acids as those mentioned for the reaction according to Reaction Scheme 3.
  • the acid can be used generally in a proportion of about 0.01 to 3 moles per mole of compound (II) 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 .
  • compound (IV) or a salt thereof and compound (VI) or a salt thereof are used generally in a substantially equimolar ratio.
  • the compound (VI) or a salt thereof may be used in excess proportion if it does not interfere with the reaction.
  • 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 an acid.
  • the acid that can be used for this purpose includes the same acids as those mentioned for the reaction according to Reaction Scheme 3.
  • the acid can be used generally in a proportion of about 0.01 to 3 moles per mole of compound (IV) 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.
  • compound (VII) or a salt thereof and compound (VIII) or a salt thereof are used generally in a substantially equimolar ratio.
  • the compound (VIII) or a salt thereof may be used in excess proportion if it does not interfere with the reaction.
  • 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 3 moles per mole of compound (VII) 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 two-stage reaction.
  • the compound (IXa) or (IXb) or a salt thereof produced by the first-stage reaction between compound (VII) or a salt thereof and compound (VIII) or a salt thereof may be isolated and submitted to the second-stage reaction or may be subjected to the second-stage reaction without prior isolation.
  • the reaction product may be in the form of a salt with the 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 (I) produced is 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 the acid used. If such is the case, the salt can be converted to a free form of the compound by adding a base such as the above-mentioned base.
  • the compound (I) is 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 (I) 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 (II), (III), (IV), (V), (VI), and (VII), inclusive of their salts, are either known compounds or compounds which can be easily prepared from known compounds .
  • compound (II) or a salt thereof can be produced by the process described in Archiv der Pharmazie, 296. 420-426, 1963) or any process analogous thereto, e.g. in accordance with the following reaction scheme .
  • Compounds (III) and (V), such as bro ochloromethane, 1, 2-dichloroethane, chloroacetyl chloride, etc., are either known compounds or compounds which can be easily produced from known compounds .
  • Compound (VI) which is a carbonyl compound such as formaldehyde, acetone or the like, is either a known compound or a compound which can be easily produced from a known compound.
  • Equivalent carbonyl compounds such as paraformaldehyde and dialkoxymethane for formaldehyde, for instance, are also either known compounds or compounds which can be easily produced from known compounds .
  • Compound (VII) can also be produced by the process described in JP-A 6943/1976 or any process analogous thereto, e.g. in accordance with 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 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, plowland s, 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 tetra ethylsilane 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 reference examples and working examples have the following meanings.
  • reaction mixture was stirred at room temperature for 5.5 hours. At room temperature, the reaction mixture was diluted with water (5 ml) and extracted with ethyl acetate. After phase separation, the organic layer was washed 3 times with 15 ml each of saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate (MgS0 4 ) , subjected to filtration and concentrated.
  • MgS0 4 anhydrous magnesium sulfate
  • the mixture was stirred for 2 hours with an spontaneous increase in temperature to a room temperature.
  • the resulting solution was added to 50 ml of ice-water, and then the mixture was extracted with 50 ml of diethylether .
  • the organic layer was washed 3 times with 30 ml of saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated.
  • Polyethylene glycol ether (Nonipol 85TM) 5 weight %
  • Wettable powders Compound 1-2 50 weight %
  • the above components are kneaded with water and granulated to provide granules .
  • the above components are kneaded with water and granulated to provide granules .
  • the above components are kneaded with water and granulated to provide granules.
  • Compound 5-1 20 weight %
  • Compound 5-1 50 weight % Sodium ligninsulfonate 5 weight %
  • the above components are kneaded with water and granulated to provide granules .
  • the above components are kneaded with water and granulated to provide granules .
  • the above components are kneaded with water and granulated to provide granules .
  • Rectangular pTastic pots with a capacity of 150 cm were filled in with paddy field soil, flooded with water, and tilled, and seeds of Echinochloa crus- ⁇ alli var. orvzicola , Cvperus difformis , Scirpus iuncoides , and Rotala indica were sown and cultivated at a submersion depth of 2 cm for a predetermined time.
  • the depth of flooding water was increased to 3 cm and dilutions of compound (Ia) were dripped over the body of water in the pots at a predetermined dose (g/a).
  • Rectangular plastic pots with a capacity of 150 cm were filled in with paddy field soil, flooded with water, and tilled. Seeds of Echinochloa crus- ⁇ alli var. orvzicola and Scirpus iuncoides were sown and one stock of rice seedlings was transplanted. Under 3 cm- deep flooding, dilutions of compound (la) were dripped over the body of water in the pots at a predetermined dose (g/a). The dilutions were prepared by the same procedure as described in Test Example 1. After the treatment, the plants were further grown in a greenhouse and at 3 weeks after treatment, the herbicidal effect on each weed and the possible harmful effect on the rice plant were scored in accordance with the criteria shown in Table 15. The results are shown in Table 17. [ Table 17 ]

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Abstract

Cette invention se rapporte à un composé d'urée ou de thio-urée cyclique, qui comprend: (i) un groupe représenté par la formule (I'), où Q1 représente un groupe cyclique aromatique qui peut éventuellement être substitué; et R1 et R2, qui sont identiques ou différents, représentent chacun un groupe hydrocarbure qui peut éventuellement être substitué ou R1 et R2 peuvent former un cycle conjointement avec l'atome de carbone adjacent, ce cycle pouvant éventuellement être substitué, ce groupe venant substituant sur l'un des atomes d'azote formant le cycle; (ii) un groupe lié par un atome de carbone, un atome d'azote ou un atome d'oxygène, comme substituant sur l'autre atome d'azote formant le cycle; et (iii) un atome d'oxygène comme autre élément cyclique; ou à un sel de ce composé; ainsi qu'à un procédé pour la production de ce composé; et à une composition. Ce composé ou un sel de ce composé possèdent une action herbicide puissante contre un large spectre de mauvaises herbes, telles que les mauvaises herbes des rizières et les mauvaises herbes des sols labourés, à des concentrations basses. Ce composé est en outre moins phytotoxique pour les plantes cultivées, telles que le riz, le blé, l'orge, le soja et le maïs, possédant par conséquent une action herbicide sélective très satisfaisante. Cette action herbicide et sélective a en outre la caractéristique de durer longtemps. Ce composé ou un sel de ce composé, qui n'ont pas d'effet néfaste sensible sur les mammifères, les poissons et les crustacés, ne créent en outre pas de problème de pollution et ils peuvent être utilisés de façon très sûre comme herbicide dans des rizières, des sols labourés, des vergers et des terres non cultivées.
PCT/JP1997/002799 1996-08-14 1997-08-11 Composes d'urees cycliques, leur production et leur utilisation comme herbicides Ceased WO1998006709A1 (fr)

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EP0959174A1 (fr) * 1998-05-18 1999-11-24 Ciba SC Holding AG Procédé de traitement de matériaux fibreux en polyamide synthétique ou naturel
US8658797B2 (en) 2011-02-25 2014-02-25 Helsinn Healthcare Sa Asymmetric ureas and medical uses thereof
US9975886B1 (en) 2017-01-23 2018-05-22 Cadent Therapeutics, Inc. Potassium channel modulators
US10501479B2 (en) 2016-03-22 2019-12-10 Helsinn Healthcare Sa Benzenesulfonyl-asymmetric ureas and medical uses thereof
US10774064B2 (en) 2016-06-02 2020-09-15 Cadent Therapeutics, Inc. Potassium channel modulators
US10894797B2 (en) 2018-09-18 2021-01-19 Nikang Therapeutics, Inc. Fused tricyclic ring derivatives as SRC homology-2 phosphatase inhibitors
US11993586B2 (en) 2018-10-22 2024-05-28 Novartis Ag Crystalline forms of potassium channel modulators

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0959174A1 (fr) * 1998-05-18 1999-11-24 Ciba SC Holding AG Procédé de traitement de matériaux fibreux en polyamide synthétique ou naturel
US8658797B2 (en) 2011-02-25 2014-02-25 Helsinn Healthcare Sa Asymmetric ureas and medical uses thereof
US9751836B2 (en) 2011-02-25 2017-09-05 Helsinn Healthcare Sa Asymmetric ureas and medical uses thereof
US10407390B2 (en) 2011-02-25 2019-09-10 Helsinn Healthcare Sa Asymmetric ureas and medical uses thereof
US10501479B2 (en) 2016-03-22 2019-12-10 Helsinn Healthcare Sa Benzenesulfonyl-asymmetric ureas and medical uses thereof
US10774064B2 (en) 2016-06-02 2020-09-15 Cadent Therapeutics, Inc. Potassium channel modulators
US9975886B1 (en) 2017-01-23 2018-05-22 Cadent Therapeutics, Inc. Potassium channel modulators
US10717728B2 (en) 2017-01-23 2020-07-21 Cadent Therapeutics, Inc. Potassium channel modulators
US10351553B2 (en) 2017-01-23 2019-07-16 Cadent Therapeutics, Inc. Potassium channel modulators
US10894797B2 (en) 2018-09-18 2021-01-19 Nikang Therapeutics, Inc. Fused tricyclic ring derivatives as SRC homology-2 phosphatase inhibitors
US11034705B2 (en) 2018-09-18 2021-06-15 Nikang Therapeutics, Inc. Fused tricyclic ring derivatives as Src homology-2 phosphate inhibitors
US11459340B2 (en) 2018-09-18 2022-10-04 Nikang Therapeutics, Inc. Tri-substituted heteroaryl derivatives as Src homology-2 phosphatase inhibitors
US11518772B2 (en) 2018-09-18 2022-12-06 Nikang Therapeutics, Inc. Fused tricyclic ring derivatives as Src homology-2 phosphate inhibitors
US12264167B2 (en) 2018-09-18 2025-04-01 Nikang Therapeutics, Inc. Fused tricyclic ring derivatives as SRC homology-2 phosphate inhibitors
US11993586B2 (en) 2018-10-22 2024-05-28 Novartis Ag Crystalline forms of potassium channel modulators

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