llllillilllililliilliIllIiillilillililllililllillllllillillllilli
`
`(11)
`
`EP 1 122 244 B1
`
` )
`
`European Patent Office
`Office européen des brevets
`
`(19) a
`
`(12)
`
`EUROPEAN PATENT SPECIFICATION
`
`(45) Date Of PUblication and mention
`“the grant “the Patent:
`29.09.2004 Bulletin 2004/40
`(21) Application number: 01102178.9
`
`(22) Date of filing: 02.02.2001
`
`(54) Uracil compounds and their use
`
`Urazil Verbindungen und deren Verwendung
`
`(51) Int CI.7: C07D 239/54, C07D 401/12,
`CO7D 417/12, CO7D 403/12,
`C07D 239/52, 007D 213/69,
`C07D 213/70, A01 N 43/54
`
`Composés d’uracile et leur usage
`
`
`(84) Designated Contracting States:
`AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU
`MC NL PT SE TR
`
`- Sanemitsu, Yuzuru
`Kobe-shi, Hyogo (JP)
`
`(30) Priority: 04.02.2000 JP 2000028123
`29.02.2000 JP 2000053521
`06.09.2000 JP 2000269730
`
`(43) Date of publication of application:
`08.08.2001 Bulletin 2001/32
`
`(74) Representative: VOSSIUS & PARTNER
`Siebertstrasse 4
`81675 Ml'inchen (DE)
`
`(56) References cited:
`EP-A- 0 255 047
`DE-A- 19 853 864
`
`WO-A-98/41093
`
`(73) Proprietor: Sumitomo Chemical Company,
`Limited
`
`Remarks:
`The file contains technical information submitted
`
`Chuo-ku Osaka 541 -8550 (JP)
`
`(72) Inventors:
`- Tohyama, Yoshitomo
`Ashiya-shi, Hyogo (JP)
`
`afterthe application was filed and not included in this
`specification
`
`EP1122244B1
`
`
`
`Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give
`notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in
`a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art.
`99(1) European Patent Convention).
`
`Printed by Jouve, 75001 PARIS (FR)
`
`

`

`Description
`
`EP1 122 244 B1
`
`[0001] The present invention relates to uracil compounds and their use.
`[0002] An object of the present invention is to provide compounds having excellent herbicidal activity.
`[0003] Currently, a lot of herbicides are commercially available and used, however since there are many kinds of
`weeds to be controlled and generation thereof ranges over a long period, there are required herbicides which have
`higher herbicidal effect, have a wide range of herbicidal spectrum, and cause no phytotoxicity on crops.
`[0004] USA-4,859,229, W092/11244, W097/O1541, W097/05116 and W098/41093 disclose that certain kinds of
`phenyluracil compounds have herbicidal activity, however, these phenyluracil compounds do not have sufficient abilities
`as a herbicide.
`
`In a first embodiment, the present invention provides uracil compounds of the formula [I] (hereinafter, referred
`[0005]
`to as the present compound):
`
`of
`
`.
`
`[I]
`
`wherein, Q-R3 represents a R3-substituted group of a 5-membered or 6-membered heterocyclic ring having one ortwo
`nitrogen atoms selected from moieties represented by the following formulae :
`
`R3
`
`
`
`Rs
`K7“
`N\ N
`\l./
`
`0-6
`
`.
`
`//'N
`\ |
`
`/N_|_-R3 O \ R / NH
`\
`HN
`\ 0
`
`3
`
`.
`
`0-3
`
`0-4
`
`0-5
`
`N -
`( 5” .3
`_ —-.H
`N\
`
`‘
`
`A
`
`N
`N
`U
`\\ 3
`R,
`
`HN—N
`\
`\
`
`3
`
`R
`
`3
`R‘
`N-N
`\
`\
`
`0—7
`
`Q 8
`
`0-9 '
`
`Q-‘iO
`
`10
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`15
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`EP1 122 244 B1
`
`-N .
`
`.
`
`N-s,
`
`QrN‘Ra Raj/YN
`
`0-12
`
`on
`
`R3
`
`‘
`
`— ,
`
`\ NH
`
`0-11
`
`wherein this heterocyclic ring may be substituted with at least one kind of substituent selected from halogen, C1 to CB
`alkyl, C1 to CB haloalkyl, 02 to CB alkenyl, C2 to CB haloalkenyl, C2 to CB alkynyl, CZ to CB haloalkynyl, C1 to CB
`alkoxy C1 to C6 alkyl, C1 to CB alkoxy, C1 to CB haloalkoxy, C1 to CB alkoxycarbonyl C1 to CB alkoxy, C1 to CB
`alkoxycarbonyl C1 to CB alkyl, cyano, hydroxy, mercapto, oxo and thioxo, Y represents oxygen, sulfur, imino or C1 to
`C3 alkylimino, R1 represents C1 to C3 alkyl or C1 to C3 haloalkyl, R2 represents C1 to C3 alkyl, R3 represents carboxy
`C1 to CB alkyl, C1 to CB. alkoxycarbonyl C1 to CB alkyl, C1 to CB haloalkoxycarbonyl C1 to CB alkyl, CB to CB alke-
`nyloxycarbonyl C1 to CB alkyl, CB to CB haloalkenyloxycarbonyl C1 to CB alkyl, CS to CB alkynyloxycarbonyl C1 to CB
`alkyl, CB to CB haloalkynyloxycarbonyl C1 to CB alkyl, 0R7, SR8 or N(R9)R1°, X1 represents halogen, cyano, thiocar-
`bamoyl or nitro, X2 represents hydrogen, or halogen,
`wherein each of R7, R‘3 and R10 independently represents carboxy C1 to CB alkyl, C1 to CB alkoxycarbonyl C1 to CB
`alkyl, C1 to CB haloalkoxycarbonyl C1 to CB alkyl, C3 to CB alkenyloxycarbonyl C1 to CB alkyl, CS to CB haloalkenyl-
`oxycarbonyl C1 to CB alkyl, C3 to CB alkynyloxycarbonyl C1 to CB alkyl, C3 to CB haloalkynyloxycarbonyl C1 to CB
`alkyl, C3 to 08 cycloalkoxycarbonyl C1 to CB alkyl, C3 to 08 halocycloalkoxycarbonyl C1 to CB alkyl, 03 to C8 cy—
`cloalkenyloxycarbonyl C1 to CB alkyl, C3 to cs halocycloalkenyloxycarbonyl C1 to CB alkyl, C1 to CB alkoxycarbonyl
`C1 to CB alkoxycarbonyl C1 to CB alkyl, C1 to C8 alkylidenaminoxycarbonyl C1 to CB alkyl, phenoxycarbonyl C1 to
`CB alkyl which may be substituted, phenyl C1 to C4 alkoxycarbonyl C1 to CB alkyl which may be substituted, C1 to
`CB alkoxyaminocarbonyl C1 to CB alkyl, (C1 to CB alkoxy)(C1 to C3 alkyl) aminocarbonyl C1 to CB alkyl, C1 to CB
`alkylaminocarbonyl C1 to CB alkyl, (C1 to CB alkyl) C1 to CB alkylaminocarbonyl C1 to CB alkyl, phenylaminocarbonyl
`C1 to CB alkyl which may be substituted, or phenyl C1 to C4 alkylaminocarbonyl C1 to CB alkyl which may be substituted,
`and R9 represents hydrogen or C1 to CB alkyl, and herbicides containing at least one of them as an effective ingredient.
`[0006]
`In a second embodiment of the present invention, the heterocyclic ring in the above uracil compound may be
`substituted with at least one kind of substituent selected from halogen, C1 to CB alkyl, C1 to CB haloalkyl, C3 to CB
`alkenyl, C3 to CB haloalkenyl, CS to CB alkynyl, C3 to CB haloalkynyl, C1 to CB alkoxy C1 to CB alkyl, C1 to CB alkoxy,
`C1 to CB haloalkoxy, C1 to CB alkoxycarbonyl C1 to CB alkoxy, C1 to CB alkoxycarbonyl C1 to CB alkyl, cyano,hydroxy,
`mercapto, oxo and thioxo, R3 represents carboxy C1 to CB alkyl, C1 to CB alkoxycarbonyl C1 to CB alkyl, C1 to CB
`haloalkoxycarbonyl C1 to CB alkyl, C3 to CB alkenyloxycarbonyl C1 to CB alkyl, 03 to CB haloalkenyloxycarbonyl C1
`to CB alkyl, C3 to CB alkynyloxycarbonyl C1 to CB alkyl, C3 to CB haloalkynyloxycarbonyl C1 to CB alkyl, 0R7, SR3 or
`N(R9)R1O,
`wherein each of W, R8 and R10 independently represents carboxy C1 to CB alkyl, C1 to CB alkoxycarbonyl C1 to C4
`alkyl, C1 to CB haloalkoxycarbonyl C1 to C4 alkyl, CS to CB alkenyloxycarbonyl C1 to C4 alkyl, C3 to CB alkynyloxy-
`carbonyl C1 to C4 alkyl, phenoxycarbonyl C1 to C4 alkyl which may be substituted, phenyl C1 to C4 alkoxycarbonyl
`C1 to C4 alkyl which may be substituted, C1 to CB alkoxyaminocarbonyl C1 to C4 alkyl, (C1 to CB alkoxy) (C1 to C3
`alkyl) aminocarbonyl C1 to C4 alkyl, C1 to CB alkylaminocarbonyl C1 to C4 alkyl, (C1 to CB alkyl) C1 to CB alkylami-
`nocarbonyl C1 to C4 alkyl, phenylaminocarbonyl C1 to C4 alkyl which may be substituted, or phenyl C1 to C4 alkylami-
`nocarbonyl C1 to C4 alkyl which may be substituted, and R9 represents hydrogen or C1 to CB alkyl.
`[0007]
`In a third embodiment of the present invention, as the group represented by Q-R3, for example, there are
`listed groups of the following formulae:
`
`
`
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`

`EP1 122 244 B1
`
`R3
`
`Z‘
`/
`. ~sz
`\ R3
`
`2.1
`_,sz
`
`\
`
`R“
`
`/
`
`21
`— 22
`
`3
`R 2'
`/—.sz
`,
`
`R?
`N-N
`\
`
`- z2
`
`z"
`
`
`
`wherein R3 is the same as defined above, each of Z1 and Z2 independently represents hydrogen, halogen, C1 to C6
`alkyl, C1 to CS haloalkyl, 02 to C6 alkenyl, C2 to CB haloalkenyl, C2 to C6 alkynyl, C2 to 06 haloalkynyl, C1 to C6
`alkoxy C1 to C6 alkyl, C1 to C6 alkoxy, C1 to C6 haloalkoxy, C1 to 06 alkoxycarbonyl C1 to C6 alkoxy or cyano, wherein
`the halogen represented by Z1 or 22 means fluorine, chlorine, bromine or iodine, and examples of the C1 to C6 alkyl
`include methyl, ethyl, propyl, isopropyl, butyl, s—butyl and t—butyl, examples ofthe C1 to C6 haloalkyl include bromome—
`thyl, chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl, chlorodifluoromethyl, bromodifluor-
`omethyl, trifluoromethyl, pentafluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2,2-trichloroethyl, 3,3,3-trifluoropropyl and
`3,3,3-trichloropropyl, examples of the C2 to C6 alkenyl
`include allyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl,
`1-butenyl, 2-butenyl and 3-butenyl, examples of the C2 to C6 haloalkenyl include 1-chloroallyl, 1-bromoallyl, 2-chloro-
`allyl and 3,3-dichloroallyl, examples of the C2 to C6 alkynyl include 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-
`2-propynyl, 2-butynyl, 3-butynyl and 1-methyl-2-butenyl, examples of the C2 to C6 haloalkynyl include 3-bromo-2-pro-
`pynyl, 3-iodo-2-propynyl, 1-fluoro-2-propynyl, 1-chloro-2-propynyl, 1-bromo-2-propynyl and 1-chloro-2-butynyl, exam-
`ples of the C1 to C6 alkoxy C1 to C6 alkyl include methoxymethyl, 2-methoxyethyl, 1-methoxyethyl, 3-methoxypropyl,
`ethoxymethyl, 2-ethoxyethyl, 3-ethoxypropyl, isopropoxymethyland 2-isopropoxyethyl, examples of the C1 to C6 alkoxy
`include methoxy, ethoxy, propoxy, isopropoxy, butyloxy, s—butyloxy and t—butyloxy, examples ofthe C1 to C6 haloalkoxy
`include chloromethoxy, bromomethoxy, dichloromethyloxy, trichloromethyloxy, trifluoromethyloxy, 2—fluoroethyloxy and
`2,2,2-trichloroethyloxy, examples of the C1 to C6 alkoxycarbonyl C1 to C6 alkoxy include methoxycarbonylmethoxy,
`ethoxycarbonylmethoxy, propoxycarbonylmethoxy, isopropoxycarbonylmethoxy, 1-methoxycarbonylethoxy, 1-ethoxy-
`carbonylethoxy, 1-propoxycarbonylethoxy, 1-isopropoxycarbony|ethoxy, 2-methoxycarbonylethoxy, 2-ethoxycarbo-
`nylethoxy, 2-propoxycarbonylethoxy and 2-isopropoxycarbonylethoxy, and like, examples of the C1 to C6 alkoxycar-
`bonyl C1 to 06 alkyl include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycar-
`bonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-pro-
`poxycarbonylethyl, 1-isopropoxycarbony|ethyl, 1-butoxycarbonylethyl and 1-t-butoxycarbonylethyl)].
`[0008] Examples of the carboxy C1 to CB alkyl represented by R3 include carboxymethyl, 1-carboxyethyl and 2-car-
`boxyethyl, examples of the C1 to C6 alkoxycarbonyl C1 to CB alkyl include methoxycarbonylmethyl, ethoxycarbonyl-
`methyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butox-
`
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`15
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`

`EP1 122 244 B1
`
`ycarbonylmethyl, amyloxycarbonylmethyl isoamyloxycarbonylmethyl, t—amyloxycarbonylmethyl, 1—methoxycarbonyle—
`thyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxy-
`carbonylethyl, 1-t-butoxycarbonylethyl, 2—methoxycarbonylethyl and 2—ethoxycarbonylethyl, examples of the C1 to CB
`haloalkoxycarbonyl C1 to CB alkyl include chloromethyloxycarbonylmethyl, 2-fluoroethyloxycarbonylmethyl, 2-chloro-
`propyloxycarbonylmethyl, 1-chloro-2-propyloxycarbonylmethyl and 2,2,2-trifluoroethyloxycarbonylmethyl, examples of
`the CBto C6 alkenyloxycarbonyl C1 to C6 alkyl include allyloxycarbonylmethyl, 1-methyl-2-propenyloxycarbonylmethyl,
`2-methyl-2-propenyloxycarbonylmethyl, 2-butenyloxycarbonylmethyl, 1-allyloxycarbonylethyl, 1-(1-methyl-2-propeny-
`loxycarbonyl)ethyl, 1-(2-methyl-2-propenyloxycarbonyl)ethy|, 2-allyloxycarbonylethyl and 2-(2—methyl-2-propenyloxy-
`carbonyl)ethyl, examples of the CB to CB haloalkenyloxycarbonyl C1 to CB alkyl include 1 -ch|oroallyloxycarbonylmethyl,
`1-(1-chloroallyloxycarbonyl)ethyl, 2—chloroallyloxycarbonylmethyl and 1-(2-chloroallyloxycarbonyl)ethyl, examples of
`the CB to CB alkynyloxycarbonyl C1 to CB alkyl include propargyloxycarbonylmethyl, 1—methyl—2—propynyloxycarbonyl—
`methyl, 1—propargyloxycarbonylethyl,
`1—(1—methy|—2—propynyloxycarbonyl)ethyl, 2—propargyloxycarbonylethyl and
`2—(1—methyl—2—propynyloxycarbonyl)ethyl, examples of the CB to CB haloalkynyloxycarbonyl C1 to CB alkyl include
`(B-chloro-2—propynyloxycarbonyl)methyl, 1-(3-chloro-2—propynyloxycarbonyl)ethyl, (1-chloro-2-propynyloxycarbonyl)
`methyl and 1-(1-chlore-2-propynyloxycarbonyl)ethyl, examples of the C1 to C3 alkylimino represented by Y include
`methylimino and ethylimino, the C1 to CB alkyl represented by R1 means methyl, ethyl, propyl or isopropyl, and exam-
`ples of the Ct to CB haloalkyl include bromomethyl, chloromethyl, fluoromethyl, dichloromethyl, chlorodifluoromethyl,
`trichloromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, 1 ,1-difluoroethyl, 2,2,2-trifluoroethyl and B,B,B-trifluor-
`opropyl, the C1 to CB alkyl represented by R2 means methyl, ethyl, propyl or isopropyl, examples of the carboxy C1
`to CB alkyl represented by R7, R8 or R10 include carboxymethyl, 1-carboxyethyl and 2—carboxyethyl, examples of the
`C1 to CB alkoxycarbonyl C1 to 06 alkyl include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylme-
`thyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, s-butoxycarbonylmethyl, t-butoxy-
`carbonylmethyl, amyloxycarbonylmethyl isoamyloxycarbonylmethyl, t—amyloxycarbonylmethyl, 1—methoxycarbonyle—
`thyl, 1—ethoxycarbonylethyl, 1—propoxycarbonylethyl, 1—isopropoxycarbonylethyl, 1—butoxycarbonylethyl, 1—isobutoxy—
`carbonylethyl, 1—s—butoxycarbonylethyl, 1—t—butoxycarbonylethyl, 2—methoxycarbonylethyl and 2—ethoxycarbonylethyl,
`examples of the C1 to CB haloalkoxycarbonyl C1 to CB alkyl include chloromethyloxycarbonylmethyl, 2—fluoroethyl-
`oxycarbonylmethyl, 2—chloropropyloxycarbonylmethyl, 1-chloro-2—propyloxycarbonylmethyl and 2,2,2—trifluoroethyl-
`oxycarbonylmethyl, examples of the CB to C6 alkenyloxycarbonyl C1 to C6 alkyl include allyloxycarbonylmethyl, 1-me-
`thy|-2-propenyloxycarbonylmethyl, 2-methyl-2—propenyloxycarbonylmethyl, 2-butenyloxycarbonylmethyl, 1-allyloxy-
`carbonylethyl, 1-(1-methy|—2-propenyloxycarbonyl)ethyl, 1-(2-methyl-2-propenylowcarbonyl)ethyl, 2-allyloxycarbo-
`nylethyl, 2-(1-methyl-2-propenyloxycarbonyl)ethyl and 2-(2-methyl-2-propenyloxycarbonyl)ethyl, examples of the CB
`to CB haloalkenyloxycarbonyl C1 to CB alkyl include 1-chloro-2-propenyloxycarbonylmethyl and 1-(2-chloro-2-prope-
`nyloxycarbonyl)ethyl, examples of the CB to C6 alkynyloxycarbonyl C1 to C6 alkyl include propargyloxycarbonylmethyl,
`1-methyl-2-propynyloxycarbonylmethyl,
`1-propargyloxycarbonylethyl,
`1-(1-methyl-2-propynyloxycarbonyl)ethyl,
`2—propargyloxycarbonylethyl and 2—(1—methy|—2—propynyloxycarbonyl)ethyl, examples of the CB to C6 haloalkynyloxy—
`carbonyl C1 to C6 alkyl include 1—bromo—2—propynyloxycarbonyl methyl and 1—(1—chloro—2—propynyloxycarbonyl)ethyl,
`examples of the CB to CS cycloalkoxycarbonyl C1 to CB alkyl include cyclopropyloxycarbonylmethyl, cyclopentyloxy—
`carbonylmethy] and 1-(cyclobutyloxycarbonyl)ethyl, examples of the C3 to C8 halocycloalkoxycarbonyl C1 to C6 alkyl
`include 2,2—difluorocyclopentyloxycarbonylmethyl, 2—bromocyclopentyloxycarbonylmethyl and 1-(2-chlorocyclobuty-
`loxycarbonyl)ethyl, examples of the CB to 08 cycloalkenyloxycarbonyl C1 to CB alkyl include 2—cyclopentenyloxycar-
`bonylmethyland 1-(2-cyclobutenyloxycarbonyl)ethy|, examples of the CB to C8 halocycloalkenyloxycarbonyl C1 to C6
`alkyl include 4-bromo-2-cyclobutenyloxycarbonylmethyl and 1-(4-bromo-2-cyclopentenyloxycarbonyl)ethyl, examples
`of the C1 to CB alkoxycarbonyl C1 to C6 alkoxycarbonyl C1 to CB alkyl include methoxycarbonylmethoxycarbonylme-
`thyl, 2—(methoxycarbonyl)-2-propoxycarbonylmethyl and 1-[1-(ethoxycarbonyl)ethoxycarbonyl]ethyl, examples of the
`C1 to 08 alkylidenaminoxycarbonyl C1 to CB alkyl include isoprpylidenaminoxycarbonylmethyl and 2—(isoprpylidenami-
`noxycarbonyl)ethyl, examples of the phenoxycarbonyl C1 to CB alkyl which may be substituted include phenoxycarb-
`onylmethyl and 1—phenyoxycarbonylethyl, examples of the phenyl C1 to C4 alkoxycarbonyl C1 to CB alkyl which may
`be substituted include benzyloxycarbonylmethyl and 1—benzyloxycarbonylethyl, examples of the C1 to C6 alkoxyami—
`nocarbonyl C1 to C6 alkyl include methoxyaminocarbonylmethyl, 1-methoxyaminocarbonylethyl, ethoxyaminocarbo-
`nylmethyl and 1-ethoxyaminocarbonylethyl, examples of the (C1 to C6 alkoxy)(C1 to CB alkyl)aminocarbonyl C1 to CB
`alkyl include (methoxy)(methyl)aminocarbonylmethyl, 1-(methoxy)(methyl)aminocarbonylethyl, (ethoxy)(methyl)ami-
`nocarbonylmethyl and 1-(ethoxy)(methyl)aminocarbonylethyl, examples of the Ct to CB alkylaminocarbonyl C1 to CB
`alkyl include methylaminocarbonylmethyl, ethylaminocarbonylmethyl, isopropylaminocarbonylmethyl, 1-methylamino-
`carbonylethyl and 1-isobutylaminocarbonylethyl, examples ofthe (C1 to CB alkyl)(C1 to CB alkyl)aminocarbonyl C1 to
`CB alkyl include dimethylaminocarbonylmethyl and 1-dimethylaminocarbonylethyl, examples of the phenylaminocar-
`bonyl C1 to CB alkyl which may be substituted include phenylaminocarbonylmethyland 1-phenylaminocarbonylethyl,
`and examples of the phenyl C1 to C4 alkylaminocarbonyl C1 to CB alkyl which may be substituted include benzylami-
`nocarbonylmethyl and 1-benzylaminocarbonylethyl, examples of the C1 to CB alkyl represented by R9 include methyl,
`
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`

`EP1 122 244 B1
`
`ethyl, propyl, isopropyl and butyl, and the halogen represented by X1 and X2 means fluorine, chlorine, bromine or iodine.
`[0009]
`In afourth embodiment of the present invention, in the uracil compound according to any of the embodiments
`one to three, X1 is halogen.
`[0010]
`In afifths embodiment of the present invention, in the uracil compound according to any of the embodiments
`one to three, X1 is nitro.
`[0011]
`In a sixth embodiment of the present invention, in the uracil compound according to any of the embodiments
`one to three, X1 is chlorine.
`[0012]
`In a seventh embodiment ofthe present invention, in the uracil compound according to any of the embodiments
`one to six, X2 is hydrogen orfluorine.
`[0013]
`In an eighth embodiment of the present invention, in the uracil compound according to any of the embodiments
`one to three, X1 is chlorine and X2 is fluorine.
`[0014]
`In a ninth embodiment of the present invention, in the uracil compound according to any of the embodiments
`one to eight, R1 is CF3.
`[0015]
`In a tenth embodiment of the present invention, in the uracil compound according to any of the embodiments
`one to nine, R2 is methyl.
`[0016]
`In an eleventh embodiment of the present invention, in the uracil compound according to any of the embod-
`iments one to ten, Y is oxygen or sulfur.
`[0017]
`In a twelfth embodiment ofthe present invention, in the uracil compound according to any of the embodiments
`one to ten, Y is oxygen.
`[0018]
`In a thirteenth embodiment of the present invention, in the uracil compound according to any of the embodi-
`ments one to twelve, R3 is 0R7, SR3 or N(R9)R1°, and R7, R8 and R10 are C1 to C6 alkoxycarbonyl C1 to C6 alkyl, C1
`to C6 haloalkoxycarbonyl C1 to 06 alkyl, C3 to C6 alkenyloxycarbonyl C1 to CG alkyl, C3 to C6 alkynyloxycarbonyl C1
`to C6 alkyl or CS to C8 cycloalkoxycarbonyl C1 to C6 alkyl.
`[0019]
`In a fourteenth embodiment of the present invention, in the uracil compound according to any of the embod—
`iments one to twelve, R3 is 0R7, SR3 or N(R9)R1°, and R7, R3 and R10 are C1 to C6 alkoxycarbonyl C1 to C3 alkyl,
`C1 to C6 haloalkoxycarbonyl C1 to CB alkyl or CB to C8 cycloalkoxycarbonyl C1 to C3 alkyl.
`[0020]
`In a fifteenth embodiment ofthe present invention, in the uracil compound according to any of the embodiments
`one to twelve, R3 is OR7 or SR8, and R7 and R9 are C1 to C6 alkoxycarbonylmethyl or 1-{(C1 to C6 alkoxy)carbonyl}
`ethyl.
`In a sixteenth embodiment of the present invention, in the uracil compound according to any of the embodi-
`[0021]
`ments one to twelve, R3 is OR7 or SR8, and R7 and R8 are methoxycarbonylmethyl, ethoxycarbonylmethyl, 1-(methox-
`ycarbonyl)ethyl or 1-(ethoxycarbonyl)ethyl.
`in the uracil compound according to any of the em-
`[0022]
`In a seventeenth embodiment of the present invention,
`bodiments one to sixteen, the group represented by Q-R3 is a group of the following formula:
`
`zE,Ra
`
`In an eighteenth embodiment of the present invention, in the uracil compound according to any of the em—
`[0023]
`bodiments one to sixteen, the group represented by Q-R3 is any group selected from moieties of the following formula:
`
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`
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`

`EP1 122 244 B1
`
`
`
`Of
`
`In a nineteenth embodiment of the present invention, in the uracil compound according to any of the embod-
`[0024]
`iments one to sixteen, the group represented by Q-Fl3 is a group of the following formula:
`
`21
`l
`
`/ /1"?
`\ R3
`
`In a twentieth embodiment, the present invention provides a herbicidal composition comprising as an active
`[0025]
`ingredient the uracil compound according to any of the embodiments one to nineteen, and an inert carrier or diluent.
`[0026]
`In a twenty-first embodiment, the present invention provides a method for controlling weeds, which comprises
`applying an effective amount of the uracil compound according to any of the embodiments one to nineteen to weeds
`or a place where the weeds grow or will grow:
`[0027]
`In a twenty-second embodiment of the present invention, the uracil compound described in any of the em-
`bodiments one to nineteen is used as a herbizide.
`
`[0028]
`
`In a twenty—third embodiment, the present invention provides a compound of the formula [XXXI]:
`
`R3
`
`x? [XXXI]
`
`x2
`
`l O
`
`wherein, X1, X2, R1, Q-R3 and Y are the same as defined in the first embodiment of the present invention.
`[0029]
`In a twenty-fourth embodiment of the present invention, the group represented by Q-R3 in the compound
`according to the twenty-third embodiment, is any group selected from moieties of the following formula:
`
`10
`
`15
`
`20
`
`25
`
`30
`
`35
`
`4o
`
`45
`
`50
`
`55
`
`

`

`EP1 122 244 B1
`
`
`
`wherein, X1 is halogen, cyano or nitro, X2 is halogen, Y is oxygen or sulfur, R1 is C1 to C3 haloalkyl, R3 is 0R7, SR8
`or N(R9)R1°, R7, R3 and R10 are C1 to C6 alkoxycarbonyl C1 to C6 alkyl, C1 to C6 haloalkoxycarbonyl C1 to C6 alkyl,
`C3 to C6 alkenyloxycarbonyl C1 to C6 alkyl, CB to C6 alkynyloxycarbonyl C1 to C6 alkyl or C3 to C8 cycloalkoxycarbonyl
`C1 to C6 alkyl, and Z1 and Z2 are the same as defined in the third embodiment of the present invention.
`[0030]
`In a twenty-fifth embodiment of the present invention, in the compound according to the twenty-third embod-
`iment, X1 is chlorine, X2 is fluorine, Y is oxygen, Q-R3 is the same as defined in the third embodiment, Z1 and Z2 are
`hydrogen, R1 is trifluoromethyl, R3 is OR7 or SR8, and R7 and R8 are methoxycarbonylmethyl, ethoxycarbonylmethyl,
`1-(methoxycarbonyl)ethyl or 1-(ethoxycarbonyl)ethyl.
`[0031]
`In a twenty-sixth embodiment of the present invention, in the compound according to the twenty-fourth em-
`bodiment, X1 is chlorine, X2 is fluorine, Y is oxygen, Z1 and Z2 are hydrogen, R1 is trifluoromethyl, R3 is OR7 or SR8,
`and R7 and R8 are methoxycarbonylmethyl, ethoxycarbonylmethyl, 1—(methoxycarbonyl)ethyl or 1—(ethoxycarbonyl)
`ethyl.
`[0032]
`
`In a twenty—seventh embodiment, the present invention provides a compound of the formula [XXXXXI]:
`
`H2N
`
`l\Ra
`Y
`
`x2
`
`x‘
`
`[XXXXX I]
`
`wherein, X1, X2, Y and Q-R3 are the same as defined in the first embodiment of the present invention.
`[0033]
`In a twenty-eighth embodiment of the present invention, the group represented by Q-R3 in the compound
`according to the twenty-seventh embodiment is any group selected from moieties of the following formula:
`
`
`
`wherein, X1 is halogen, cyano or nitro, X2 is halogen, Y is oxygen or sulfur, R3 is 0R7, SR8 or N(R9)R1°, R7, R8 and
`R10 are C1 to CB alkoxycarbonyl C1 to C6 alkyl, C1 to C6 haloalkoxycarbonyl C1 to C6 alkyl, CS to C6 alkenyloxycar-
`bonyl C1 to C6 alkyl, C3 to CB alkynyloxycarbonyl C1 to C6 alkyl or CS to CB cycloalkoxycarbonyl C1 to C6 alkyl, and
`Z1 and Z2 are the same as defined in the third embodiment of the present invention.
`
`10
`
`15
`
`20
`
`25
`
`30
`
`35
`
`4o
`
`45
`
`50
`
`55
`
`

`

`EP1 122 244 B1
`
`in the compound according to the twenty—seventh
`In a twenty—ninth embodiment of the present invention,
`[0034]
`embodiment, X1 is chlorine, X2 is fluorine, Y is oxygen, Q-R3 is the same as defined in the third embodiment of the
`present invention, Z1 and 22 are hydrogen, R3 is OR7 or SR3, and R7 and R3 are methoxycarbonylmethyl, ethoxycar-
`bonylmethyl, 1-(methoxycarbonyl)ethyl or 1-(ethoxycarbonyl)ethy|.
`[0035]
`In a thirtieth embodiment of the present invention, in the compound according to the twenty-eighth embodi-
`ment, X1 is chlorine, X2 is fluorine, Y is oxygen, 21 and Z2 are hydrogen, R3 is OR7 or SR3, and R7 and R3 are meth-
`oxycarbonylmethyl, ethoxycarbonylmethyl, 1-(methoxycarbonyl)ethyl or 1-(ethoxycarbonyl)ethyl.
`[0036]
`In a thirty-first embodiment, the present invention provides a compound according to the twenty-seventh em-
`bodiment, which is one selected from
`
`4—chloro—2—fl uoro—5—{2—(methoxycarbonyl)methoxy—S—pyridyloxy}aniline,
`4—chloro—2—fl uoro—5—{2—(ethoxycarbonyl)methoxy—S—pyridyloxy}aniline,
`4—chloro—2—fluoro—5—[2—{1—(methoxycarbonyl)ethoxy}—3—pyridyloxy]aniline,
`4-chloro-2-fluoro-5-[2—{1-(ethoxycarbony|)ethoxy}-3-pyridyloxy]aniline,
`4-chloro-2-fl uoro-5-[4-(methoxycarbonyl)m ethoxy-2-pyrim idyloxy]an il ine,
`4-chloro-2-fl uoro-5-[4-(ethoxycarbonyl)methoxy-2—pyrimidyloxy]aniline,
`4-chloro-2-fluoro-5-[4-{1-(methoxycarbonyl)ethoxy}-2—pyrimidyloxy]aniline, and
`4-chloro-2-fluoro-5-[4-{1-(ethoxycarbonyl)ethoxy}-2-pyrimidyloxy]aniline.
`
`[0037]
`
`In a thirty-second embodiment, the present invention provides a compound of the formula [XXXXXIII]:
`
`o|
`
`\Ra
`Y
`
`mm
`
`w_
`f
`[XXXXXIII]
`
`wherein, X1, X2, Y and Q-R3 are the same as defined in the first embodiment of the present invention.
`[0038]
`In a thirty-third embodiment of the present invention, the group represented by Q-R3 in the compound ac-
`cording to the thirty—second embodiment is any group selected from moieties of the following formula:
`
`
`
`wherein, X1 is halogen, cyano or nitro, X2 is halogen, Y is oxygen or sulfur, R3 is 0R7, SR8 or N(R9)R1°, R7, R3 and
`R10 are C1 to C6 alkoxycarbonyl C1 to C6 alkyl, C1 to C6 haloalkoxycarbonyl C 1 to C6 alkyl, C3 to C6 alkenyloxy-
`carbonyl C 1 to C6 alkyl, C3 to C6 alkynyloxycarbonyl C1 to C6 alkyl or C3 to C8 cycloalkoxycarbonyl C1 to C6 alkyl,
`and Z1 and Z2 are the same as defined in the third embodiment of the present invention.
`[0039]
`In a thirty-fourth embodiment of the present invention, in a compound according to the thirty-second embod-
`iment, X1 is chlorine, X2 is fluorine, Y is oxygen, Q-R3 is the same as defined in the third embodiment of the present
`invention, Z1 and 22 are hydrogen, R3 is OR7 or SR8, and R7 and R8 are methoxycarbonylmethyl, ethoxycarbonylmethyl,
`1-(methoxycarbonyl)ethyl or 1-(ethoxycarbonyl)ethyl.
`[0040]
`In a thirty-fifth embodiment of the present invention, in the compound according to the thirty-third embodiment,
`X1 is chlorine, X2 is fluorine, Y is oxygen, Z1 and Z2 are hydrogen, R3 is OR7 or SR8, and R7 and R8 are methoxycar-
`
`10
`
`15
`
`20
`
`25
`
`30
`
`35
`
`4o
`
`45
`
`50
`
`55
`
`

`

`5
`
`10
`
`15
`
`2‘0
`
`25
`
`30
`
`35
`
`40
`
`45
`
`50
`
`55
`
`EP1 122 244 B1
`
`bonylmethyl, ethoxycarbonylmethyl, 1—(methoxycarbonyl)ethyl or 1 —(ethoxycarbonyl)ethyl.
`[0041]
`In a thirty-sixth embodiment, the present invention provides a compound according to the thirty-second em-
`bodiment, which is one selected from
`
`4-chloro-2-fluoro-5-{2—(methoxycarbonyl)methoxy-S-pyridyloxy}phenyl isocyanate,
`4-chloro-2-fluoro-5-{2—(ethoxycarbony|)methoxy-3-pyridyloxy}phenyl isocyanate,
`4-chloro-2-fluoro-5-[2—{1-(methoxycarbonyl)ethoxy}-3-pyridyloxy]phenyl isocyanate,
`4-chloro-2-fluoro-5-[2-{1-(ethoxycarbonyl)ethoxy}-3-pyridyloxy]phenyl isocyanate,
`4-chloro-2-fluoro-5-[4-(methoxycarbonyl)methoxy-Z-pyrimidyloxy]phenyl isocyanate,
`4-chloro-2-fluoro-5-[4-(ethoxycarbony|)methoxy-2-pyrimidyloxy]phenyl isocyanate,
`4—chloro—2—fluoro—5—[4—{1—(methoxycarbonyl)ethoxy}—2—pyrimidyloxy]phenyl isocyanate, and
`4—chloro—2—fluoro—5—[4—{1—(ethoxycarbonyl)ethoxy}—2—pyrimidyloxy]phenol isocyanate.
`
`In a thirty-seventh embodiment, the present invention provides a compound according to the first embodiment,
`[0042]
`which is one selected from
`
`3-{2—chloro-4-fluoro-5-[3-me_hyl-2,6-dioxo-4-(trifluoromethyl)—1 ,2,3,6-te_rahydropyrimidin-1-yl]phenoxy}-2-(meth-
`oxycarbonyl)methoxypyridine,
`3-{2-chloro-4-fluoro-5-[3-me hyl-2,6-dioxo-4-(trifluoromethyl)-1 ,2,3,6-te rahydropyrimidin-1-yl]phenoxy}-2-(ethox-
`ycarbonyl)methoxypyridine,
`3-{2—ch|oro-4-fluoro-5-[3-me_hyl-2,6-dioxo-4-(trifluoromethyl)-1 2,3,6-te_rahydropyrimidin-1-yl]phenoxy}-2-
`{1 -(m ethoxycarbonyl)ethoxy}pyridine,
`3—{2—ch|oro—4—fluoro—5—[3—me_hyl—2,6—dioxo—4—(trifluoromethyl)—1 2,3,6—te_rahydropyrimidin—1—yl]phenoxy}—2—
`{1 —(ethoxycarbonyl)ethoxy}pyridine,
`2—{2—chloro—4—fluoro—5—[3—me_hyl—2,6—dioxo—4—(trifluoromethyl)—1 ,2,3,6—te_rahydropyrimidin—1—yl]phenoxy}—4—(meth—
`oxycarbonyl)methoxypyrimidine,
`2-{2—chloro-4-fluoro-5-[3-me_hyl-2,6-dioxo-4-(trifluoromethyl)—1 2,3,6-te_rahydropyrimidin-1-yl]phenoxy}-4-(ethox-
`ycarbonyl)methoxypyrimidine,
`2-{2-chloro-4-fluoro-5-[3-me_hyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-te_rahydropyrimidin-1-yl]phenoxy}-4-
`{1-(methoxycarbonyl)ethoxy}pyrimidine, and
`2-{2-chloro-4-fluoro-5-[3-me hyl-2,6-dioxo-4-(trifluoromethyl)-1 ,2,3,6-te rahydropyrimidin-1-yl]phenoxy}-4-
`{1 -(ethoxycarbonyl)ethoxy}pyrimidine.
`
`
`
`
`
`In a thirty-eighth embodiment, the present invention provides a compound according to the twenty-third em-
`[0043]
`bodiment, which is one selected from
`
`3—{2—chloro—4—fluoro—5—[2,6—dioxo—4—(trifluoromethyl)—1,2,3,6—tetrahydropyrimidin—1—yl]phenoxy}—2—(methoxycarbo—
`nyl)methoxypyridine,
`3-{2—chloro-4-fluoro-5-[2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-(ethoxycarbo-
`nyl)methoxypyridine,
`3-{2-chloro-4-fluoro-5-[2,6-dioxo-4-(thifluoromethyI)-1,2,3,6-tetrahydropyrimidin-1-y|]phenoxy}-2-{1-(methoxycar-
`bonyl)ethoxy}pyridine,
`3-{2-chloro-4-fluoro-5-[2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-{1-(ethoxycarbo-
`nyl)ethoxy}pyridine,
`2—{2—chloro-4-fluoro-5-[2,6-dioxo-4-(trifluoromethyl)-1,2,3,6—tetrahydropyrimidin-1-yl]phenoxy}-4-(methoxycarbo-
`nyl)methoxypyrimidine,
`2—{2—chloro—4—fluoro—5—[2,6—dioxo—4—(trifluoromethyl)—1,2,3,6—tetrahydropyrimidin—1—yl]phenoxy}—4—(ethoxycarbo—
`nyl)methoxypyrimidine,
`2—{2—chloro-4-fluoro-5-[2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-4-{1-(methoxycarb-
`onyl)ethoxy}pyrimidine, and
`2-{2—chloro-4-fluoro-5-[2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-4-{1-(ethoxycarbo-
`nyl)ethoxy}pyrimidine.
`
`[0044]
`
`In a thirty-ninth embodiment, the present invention provides a compound of the formula:
`
`10
`
`

`

`EP1 122 244 B1
`
`N\ O\
`
`R7
`
`/
`
`OH
`
`wherein, R7 is the same as defined in the first embodiment of the present invention.
`[0045]
`In a fortieth embodiment, the present invention provides a compound according to the thirty-ninth embodiment
`of the invention, which is one selected from
`
`2—(methoxycarbonyl)methoxy—B—hydroxypyridine,
`2—(ethoxycarbonyl)methoxy-3-hydroxypyridine,
`2-{1-(methoxycarbony|)ethoxy}-3-hydroxypyridine, and
`2—{1-(ethoxycarbonyl)ethoxy}-3-hydroxypyridine.
`
`[0046]
`
`In a forty-first embodiment, the present invention provides a compound of the formula:
`
`N\'
`
`s\R34
`
`/OH
`
`wherein R34 is C1 to CB alkoxycarbonyl methyl, 1-(C1 to C6 alkoxycarbonyl)ethy|, C1 to C6 haloalkoxycarbonyl methyl,
`1-(C1 to C6 haloalkoxycarbonyl)ethyl, C3 to 08 cycloalkoxycarbonyl methyl, 1-(C3 to CB cycIoalkoxycarbonyl)ethyl.
`[0047]
`In the present compounds, from the standpoint of herbicidal activity, those are preferable wherein Q-R3 is Q-
`1, 0-2 or 0-6, Y is oxygen or sulfur, more preferably oxygen, R1 is methyl substituted with fluorine (for example,
`trifluoromethyl, chlorodifluoromethyl or difluoromethyl), or ethyl substituted with fluorine (for example, pentafluoroethyl
`or 1,1-difluoroethyl), more preferably trifluoromethyl, R2 is methyl or ethyl, more preferably methyl, R3 is C1 to C4
`alkoxycarbonyl C1 to C4 alkyl, C1 to C4 alkoxycarbonyl C1 to C4 alkoxy, C3 to C7 cycloalkoxycarbonyl C1 to C4 alkoxy,
`C1 to C4 alkoxycarbonyl C1 to C4 alkylthio or C1 to C4 alkoxycarbonyl C1 to C4 alkylamino, more preferably C1 to
`CZ alkoxycarbonyl C1 to 02 alkoxy, X1 is halogen, more preferably chlorine, and/or X2 is halogen, more preferably
`fluorine.
`
`Sometimes, geometrical isomers based on double bond, optical isomers and diastereomers based on asym-
`[0048]
`metric carbon, may be present in the present compound, and the present compound also includes these isomers and
`mixtures thereof.
`
`[0049] Next, methods for producing the present compounds will be illustrated.
`[0050] The present compound can be produced, for example, by the following (Production Method 1) to (Production
`Method 10).
`
`(Production Method 1)
`
`[0051] Ofthe present compounds, the compound [l]wherein R3 is 0R7, SR8 or N(R9)R1o can be produced by reacting
`a com