WO2000029410A1 - Derives de la thiazolone presentant un heterocycle polycyclique en position 2, et pesticides le contenant comme ingredient actif - Google Patents

Derives de la thiazolone presentant un heterocycle polycyclique en position 2, et pesticides le contenant comme ingredient actif Download PDF

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Publication number
WO2000029410A1
WO2000029410A1 PCT/JP1999/006316 JP9906316W WO0029410A1 WO 2000029410 A1 WO2000029410 A1 WO 2000029410A1 JP 9906316 W JP9906316 W JP 9906316W WO 0029410 A1 WO0029410 A1 WO 0029410A1
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optionally substituted
substituted
alkoxy
lower alkyl
alkyl
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PCT/JP1999/006316
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English (en)
Japanese (ja)
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Koichi Morita
Toru Nakai
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Shionogi & Co., Ltd.
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    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01N43/84—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4

Definitions

  • the present invention relates to a novel thiazolone derivative useful as an active ingredient of a pesticide, particularly a herbicide.
  • An object of the present invention is to provide a compound having utility such as superior herbicidal activity.
  • the present inventors have conducted intensive studies to achieve the above object, and as a result, have found that the thiazolone derivatives described below have excellent herbicidal activity, and have completed the present invention. That is, the present invention
  • R 1 and R are each independently a hydrogen atom, a halogen atom, a hydroxy, a cyano, an optionally substituted phenyl, a lower alkoxycarbonyl, a halogenated lower alkoxycarbonyl, Lower alkenyloxycarbonyl, lower alkynyloxycarbonyl, optionally substituted phenyloxycarbonyl, optionally substituted carbamoyl, or lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy or lower alkenyl Nyloxy (the lower alkyl, the lower alkenyl, the lower alkynyl, the lower alkoxy, and the lower alkenyloxy include a halogen atom, cyano, hydroxy, lower alkoxy, mercapto, lower alkylthio, carboxyl, lower alcohol, Coxycarbonyl, lower alkoxycarbonyl halide, lower alkenyloxycarbonyl, alkenyloxycarbonyl,
  • M independently represents 0, S (0) m (where m represents 0, 1 or 2)) or NR 4;
  • A independently indicates CR 5 R 6 ,
  • B independently represents CR 7 ;
  • R 4 to R 7 each independently represent a hydrogen atom, a halogen atom, hydroxy, alkanoyl, nitro, cyano, optionally substituted phenyl, optionally substituted phenyl lower alkyl, substituted Phenyloxy, optionally substituted phenyl lower alkoxy, optionally substituted phenyloxy lower alkyl, lower alkoxycarbonyl, halogenated lower alkoxycarbonyl, lower alkenyloxycarbonyl, lower alkynyloxycarbonyl, substituted Phenyloxycarbonyl, optionally substituted rubamoyl, or lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy or Or lower alkenyloxy (the lower alkyl, the lower alkenyl, the lower alkynyl, the lower alkoxy and the lower alkenyloxy are a group consisting of a halogen atom, cyano, hydroxy, lower alkoxy, mercapto
  • W is — A— A—, —A— A— A—, — A— A— A—, one M— A— A one, or one M— A— A— A— (each (The meaning of the symbol is the same as defined above.),
  • R 4 to R 7 are each independently a hydrogen atom, a halogen atom, a hydroxy, an alkanoyl, a nitro, a cyano, or a lower alkyl, a lower alkenyl, a lower alkynyl, a lower alkoxy or a lower alkenyloxy
  • the lower alkyl, the lower alkenyl, the lower alkynyl, the lower alkoxy and the lower alkenyloxy may have a substituent selected from the group consisting of halogen atom, hydroxy, lower alkoxy, mercapto and lower alkylthio.
  • R 3 is independently a lower alkyl, a lower alkoxy, a di-lower alkylamino group or a halogen atom, and n is 0-4, any one of (2)-(4) A compound of the formula, a salt thereof, or a hydrate thereof,
  • (6) 11 1 Oyobi 11 2 it it independently, hydrogen, lower alkyl, halogenated lower alkyl, Shiano lower alkyl, lower alkoxy-lower alkyl, lower alkenyl, lower alkynyl, or halogen atom, a lower A compound according to any one of (1) to (5), which is phenyl or phenyl lower alkyl optionally having 1 to 3 substituents selected from the group consisting of alkyl and lower alkoxy; Its salts, or their hydrates,
  • W is — CH 2 CH 2 —,-CH 2 CH (CH 3) one,-CH 2 CH 2 CH 2 —,-CH (CH 3) CH 2 CH 2 —,-C (CH 3) 2 CH 2 CH 1 CH-CH 2 CH 2 CH (CH 3) CH-CH 2 CH 2 CH 2 CH 0 CH 2 CH 2-0 CH (CH 3) CH 2 -,-0 CH 2 CH (CH 3) -, - 0 CH ( CH 3) CH (CH 3) one, - 0 C (CH 3) 2 C H 2 -, - 0 CH 2 CH 2 CH 2 -, one S CH 2 CH 2 -, one S CH (CH 3) CH 2 ⁇ .-SCH 2 CH (CH 3) one, — S CH (CH 3) CH (CH 3 ) ⁇ ,-SC (CH 3 ) 2 ⁇ H 2 — or one SCH 2 CH 2 CH 2 — wherein the sulfur atom may be substituted by one or two oxo; R 1 and R are each independently a hydrogen atom,
  • R 1 and R are each independently a hydrogen atom, a halogen atom, Atom, hydroxy, cyano, optionally substituted phenyl, lower alkoxycarbonyl, halogenated lower alkoxycarbonyl, lower alkenyloxycarbonyl, lower alkynyloxycarbonyl, optionally substituted phenyloxycarbonyl, substituted Or lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy or lower alkenyl oxy (the lower alkyl, the lower alkenyl, the lower alkynyl, the lower alkoxy and the lower alkenyl oxy) , Halogen atom, cyano, hydroxy, Lower alkoxy, mercapto, lower alkylthio, carboxyl, lower al
  • lower is a straight or branched chain having 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms. Represents a branched group (except when carbon number 1 cannot be taken chemically).
  • the nitrogen atom bonded to the 2-position of the thiazolone ring represented by Examples of the polycyclic heterocyclic group which may be included include, as a ring-constituting atom, one heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom in addition to the above-mentioned nitrogen atom. And a substituted or unsubstituted bicyclic heterocyclic group which may have 4 to 4.
  • Examples of the substituent of the polycyclic heterocyclic group having a nitrogen atom bonded to the 2-position of the thiazolone ring as a ring-constituting atom include, for example, a group represented by R 3 described below.
  • M independently represents 0, S (0) m (where m represents 0, 1 or 2), or NR 4, but preferably 1) 0 or 2) S ( 0) m (m is as defined above).
  • W include, for example, one CH 2 CH 2 —, — CH 2 CH (CH 3) —, — CH 2 CH 2 CH 2 —, — CH (CH) CH 2 CH 2 —, —C ( CH 3) 2 CH 2 CH 2-,-CH 2 CH 2 CH (CH 3)-,-CH 2 CH 2 CH 2 CH 2 One O CH 2 CH 2-,-0 CH (CH 3) CH 2- , -0 CH 2 CH (CH 3) one,-0 CH (CH 3) CH (CH 3 ) one,-0 C (CHQ)
  • halogen atom represented by R 1 to R 7 and Y in the general formula (III) examples include fluorine, chlorine, bromine and iodine. Preferably, they are fluorine, chlorine and bromine.
  • Examples of the lower alkyl represented by R 1 to R ′ include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, pentyl, isopentyl, neopentyl, t-pentyl, 1 —Ethylpropyl, hexyl, isohexyl, heptyl and octyl. Of these, methyl, ethyl, propyl and n-butyl are preferred. Most preferred is methyl.
  • the lower alkenyl represented by R 1 to R 7 may preferably have one or two or more double bonds, for example, vinyl, aryl, isopropyl, 1-propenyl, 2-Methyl-1-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-ethyl-1-butenyl, 3-methyl-2-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl , 4-methyl-3-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-heptenyl and the like.
  • vinyl, aryl and isoprolenyl are preferred. Most preferred is aryl.
  • Examples of the lower alkynyl represented by R 7 include ethynyl, 1-propynyl, propargyl, 2-pentene 4-ynyl and the like. Preferred is propargyl.
  • Examples of the lower alkoxy represented by R 1 to R ′ include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentoxy, and isopentoxy. Preferably, it is methoxy.
  • the lower alkenyloxy represented by R 1 to R 7 the lower alkenyl is the same as defined above, for example, bieroxy, aryloxy, 1-propenyloxy, 2-methyl-11-provenyloxy, 1 And alkenyloxy such as butenyloxy, 2-butenyloxy, 3-butenyloxy and 2-ethyl-1-butenyloxy.
  • it is aryloxy.
  • Examples of the optionally substituted amino substituent represented by R 3 include lower alkyl, lower alkenyl, halogenated lower alkyl, halogenated lower alkenyl, lower alkylcarbonyl, and lower alkoxycarbonyl.
  • Preferable specific examples of the “optionally substituted amino group” include amino, mono-lower alkylamino (eg, methylamino and ethylamino), di-lower alkylamino (eg, dimethylamino and acetylamino), and acetylamino.
  • Examples of the optionally substituted mercapto represented by R 3 include lower alkylthio. Specific examples include methylthio, ethylthio and propylthio.
  • Examples of the optionally substituted silyl represented by R 3 include silyl optionally substituted by lower alkyl. Specific examples include trimethylsilyl, triethylsilyl, and triprovilsilyl.
  • Examples of the substituent of the optionally substituted phenyl represented by R 1 to R ′ include lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy and lower alkenyloxy represented by R 1 and R 2.
  • lower alkyl, lower alkyl halide, lower alkenyl, lower alkenyl halide, lower alkynyl and the like can be mentioned.
  • the meaning of the lower alkyl moiety is the same as described above, but the substituents of the lower alkyl moiety are represented by R 1 and R
  • R 1 and R The same substituents as those exemplified for the lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, and lower alkenyloxy groups are exemplified.
  • lower alkyl, halogenated lower alkyl, lower alkenyl, halogenated lower alkenyl, lower alkynyl and the like Specifically, benzyl, phenethyl, 2-chlorophenylmethyl, 3-chlorophenylmethyl,
  • R 3 to R 7 Monomethylphenyl, 4-methoxyphenylmethyl, 2- (3-chlorophenyl) ethyl and 1-methyl-2- (2-methylphenyl) ethyl.
  • substituent of the optionally substituted phenyloxy represented by R 3 to R 7 include lower alkyl, lower alkenyl, lower alkynyl, lower alkenyl represented by R 1 and R ′′.
  • Lower alkyl, halogenated lower alkyl, lower alkenyl, halogenated lower alkenyl, lower alkynyl, and the like, in addition to the same substituents as those exemplified for the lower alkoxy and the lower alkenyloxy, are exemplified. Specific examples include 4-methylphenyloxy, 3-methoxyphenyloxy, 2,4-dichlorophenyloxy and 3-methylphenyloxy.
  • the meaning of the lower alkoxy moiety is the same as described above, but the substituent of the lower alkoxy moiety is represented by R 1 and R 2
  • Substituents of lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, and lower alkenyloxy are the same as those exemplified above, and the substituent of the phenyl moiety is the same as the substituent of the lower alkoxy moiety.
  • Other examples include lower alkyl, halogenated lower alkyl, lower alkenyl, halogenated lower alkenyl and lower alkynyl.
  • R 3 to R 7 the meaning of the lower alkyl portion is the same as described above, but the substituents of the lower alkyl portion include R 1 and R 2
  • substituents for the lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy and lower alkenyloxy include the same substituents as those exemplified above, and the substituent for the phenyl moiety includes the substituent for the lower alkyl moiety.
  • lower alkyl halogenated lower alkyl, lower alkenyl, halogenated lower alkenyl, lower alkynyl and the like.
  • Specific examples include phenyloxymethyl, 3-methylphenyloxymethyl, 4-methoxyphenyloxymethyl, and 2-chlorophenyloxymethyl.
  • alkanol represented by R to R examples include alkanols having 2 to 6 carbon atoms, preferably 2 to 4 carbon atoms. Specifically, acetyl, ethyl carbonyl, n-propylcarbonyl, isopropylcarbonyl and n-butylethyl Luponyl and the like.
  • Halogen atom and lower alkoxy selected as substituents of lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy and lower alkenyloxy represented by R 1 to R ′ have the same meaning as described above.
  • the lower alkylthio the lower alkyl is the same as described above, and examples thereof include methylthio, ethylthio, n-propylthio, isopropyl, n-butylthio, and t-butylthio.
  • it is methylthio.
  • the lower alkoxycarbonyl represented by R 1 and R the lower alkoxy is the same as described above, and examples thereof include methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, And alkoxycarbonyl such as butoxycarbonyl. Preferred are methoxycarbonyl and ethoxycarbonyl.
  • halogenated lower alkoxycarbonyl represented by R 1 and R 2 include a lower alkoxycarbonyl substituted with 1 to 5 nitrogen atoms (eg, fluorine, chlorine, bromine and iodine) (as defined above).
  • alkoxycarbonyl halides such as chloromethoxycarbonyl, 2-chloromouth ethoxycarbonyl, 3-fluoro-n-propoxycarbonyl, and 4-promo n-butoxycarbonyl.
  • it is chloromethoxycarbonyl.
  • the lower alkenyloxycarbonyl represented by R 1 and R 2
  • the lower alkenyl is the same as described above, for example, vinyloxycarbonyl, aryloxycarbonyl, isopropenyloxycarbonyl, Phenoxycarbonyl and alkenyloxycarbonyl such as 2-butenyloxycarbonyl.
  • it is aryloxycarbonyl.
  • the lower alkynyloxycarbonyl represented by R 1 and R 2 is the same as described above, for example, ethynyloxycarbonyl, And alkynyloxycarbonyl such as propynyloxycarbonyl, 2-propynyloxycarbonyl and 2-pentene-4-ynyloxycarbonyl. Preferably, it is 2-propieroxycarbonyl.
  • R 1 and R which may be substituted phenylalanine O alkoxycarbonyl represented by 2
  • R 1 and R 2 a substituent of the lower alkenyl Oyo fine lower alkynyl represented by R 1 and R 2
  • R 1 and R 2 substituent of the lower alkenyl Oyo fine lower alkynyl represented by R 1 and R 2
  • lower alkyl, lower alkyl halide, lower alkenyl, lower alkenyl halide and lower alkynyl can be mentioned.
  • Specific examples include phenyloxycarbonyl, 4-methylphenyloxycarbonyl, 3-methoxyphenyloxycarbonyl and 2-methylphenyloxycarbonyl.
  • R 1 and R R 1 and R similar to those exemplified as substituents of lower alkyl, lower alkenyl and lower alkynyl represented by
  • lower alkyl, halogenated lower alkyl, lower alkenyl, halogenated lower alkenyl, lower alkynyl and the like can be mentioned.
  • Specific examples thereof include carbamoyl, N-methylcarbamoyl, N, N-dimethylcarbamoyl, N-ethylcarbamoyl, N, N-methylcarbamoyl and N-butylcarbamoyl.
  • Rings formed by R 1 and R 2 together with adjacent carbon atoms include hydrocarbon rings and hetero rings.
  • the above-mentioned hydrocarbon ring is a saturated or unsaturated hydrocarbon ring. It preferably has at least a methylene chain to form a ring.
  • cycloalkyl cycloalkenyl and cycloalkadienyl.
  • examples of the cycloalkane thus formed include cycloalkanes having 3 to 8 carbon atoms such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane and cyclooctane. Preference is given to cyclobutene, cyclobutane, cyclopentane and cyclohexane.
  • Examples of the cycloalkene formed include cycloalkenes having 4 or 8 carbon atoms, such as 2-cyclopentene, 3-cyclopentene, 2-cyclohexene, and 3-cyclohexene.
  • cycloalkadiene formed therefrom examples include, for example, cycloalkadienes having 4 to 8 carbon atoms such as 2,4-cyclopentadiene, 2,4-cyclohexadiene, and 2,5-cyclohexadiene. No.
  • hydrocarbon groups include, for example, indane, indene, 2H-indene, 1,4-dihydronaphthylene, and the like.
  • substituent for the above-mentioned hydrocarbon ring include the same substituents as those exemplified for the lower alkyl, lower alkenyl and lower alkynyl represented by R 1 and R, as well as lower alkyl, lower alkyl and halogenated halogen. Examples include lower alkyl and halogenated lower alkenyl.
  • heterocyclic ring examples include a 5- to 10-membered monocyclic or polycyclic ring containing from 1 to 4 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms.
  • Formula heterocycles are mentioned.
  • the monocyclic hetero ring formed include, for example, tetrahydroplothiophene, tetrahydrofuran, tetrahydropyran, 2-pyran, tetrahydropyropenyl, 2-chlorone, xanthene, 2x —Pyrrol, pyrrolidine, pyrroline, imidazolidin, imidazoline, vilazolidine, virazoline, piperidine, piperazine and morpholine.
  • Tetrahidrofuran And tetrahydropyran are examples of the monocyclic hetero ring formed.
  • condensed polycyclic hetero ring formed examples include, for example, isochroman, chroman, indoline, isoindoline, and quinocridine.
  • substituent for the above-mentioned hetero ring include the same as those exemplified as the substituent for the lower alkyl, lower alkenyl and lower alkynyl represented by R 1 and R ", as well as lower alkyl, lower alkenyl and halogen. Lower alkyl and halogenated lower alkenyl.
  • the lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy and lower alkenyloxy represented by R to R 7 have a substituent selected from the group consisting of halogen atom, hydroxy, lower alkoxy, mercapto and lower alkylthio. It may be.
  • the number of substituents is 1 to 5, preferably 1 to 3.
  • the substituents may be the same or different.
  • the position of the substituent is not particularly limited. Hereinafter, those substituted with one type of substituent will be exemplified, but this is not intended to exclude two or more types.
  • Examples of the lower alkyl substituted with a halogen atom include lower alkyl substituted with 1 to 4 halogen atoms (eg, fluorine, chlorine, bromine, iodine, etc.), specifically, 2-fluoroethyl, 2 , 2,2-Trifluoroethyl, 3-Fluoropropyl, Chloromethyl, 2-Chloroethyl, 3-Chloropropyl, 4-Chlorobutyl, 2-Bromoethyl, 2-Fedoethyl, 3-Fluoropropyl, 3-Chloropropyl Propyl, 3-bromopropyl, 3-iodopropyl, 4-chlorobutyl and 4-bromobutyl and the like.
  • halogen atoms eg, fluorine, chlorine, bromine, iodine, etc.
  • Examples of the lower alkenyl substituted with a halogen atom include lower alkenyl substituted with 1 to 4 halogen atoms (eg, fluorine, chlorine, bromine, and iodine), specifically, 2-fluorovinyl, 3-fluorovinyl and the like. Examples include fluoroallyl, 2-chlorovinyl, 3-chloroallyl, 4-chloro-1-butenyl, 2-bromovinyl, 3-bromoaryl, and 4-bromo-2-butenyl.
  • halogen atoms eg, fluorine, chlorine, bromine, and iodine
  • lower alkynyl substituted with a halogen atom examples include lower alkynyl substituted with 1 to 4 halogen atoms (eg, fluorine, chlorine, bromine, iodine, etc.), specifically, 2-fluorethynyl, 3 — Chloro-1-propenyl, 3-fluoro-2-propynyl and 1-chloro-2-penten-1-ynyl and the like.
  • halogen atoms eg, fluorine, chlorine, bromine, iodine, etc.
  • Examples of the lower alkoxy substituted with a halogen atom include methoxy, ethoxy, propoxy, isopropoxy, butoxy, substituted with 1 to 4 halogen atoms (eg, fluorine, chlorine, bromine, iodine, etc.). And lower alkoxy such as isobutoxy, s-butoxy, t-butoxy, pentoxy and isopentoxy. Specifically, preferred are fluoromethoxy, chloromethoxy, difluoromethoxy, trifluoromethoxy, trichloromethoxy, 2-bromoethoxy, 1,2-dichloromethylpropyl and the like.
  • Examples of the lower alkenyloxy substituted with a halogen atom include those substituted with 1 to 4 halogen atoms (eg, fluorine, chlorine, bromine and iodine).
  • halogen atoms eg, fluorine, chlorine, bromine and iodine.
  • vinyloxy, aryloxy, 1-pro Lower alkenyloxy such as niloxy, 2-methyl-1-propenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy and 2-ethyl-1-butenyloxy and the like.
  • 2-fluoro-vinyloxy, 3-fluoro-aryloxy, 3-fluoro-1-propenyloxy, 2-methyl-1-propenyloxy, 1-butenyloxy, 2-butenyloxy, 3 -Butenyloxy and 2-ethyl-1-butenyloxy and the like are preferred.
  • Examples of the lower alkyl substituted with cyano include lower alkyl substituted with one to three cyano. Specific examples include cyanomethyl, 2-cyanoethyl and 3-cyanopropyl.
  • Examples of the lower alkenyl substituted by cyano include lower alkenyl substituted by 1 to 3 cyano, specifically, 2-cyanovinyl, 3-cyanoallyl, 3 Examples include 4-cyanoaryl, 4-cyano-1-butenyl and 4-cyano-2-buthel.
  • lower alkynyl substituted with cyano includes lower alkynyl substituted with 1 to 3 cyano, specifically, 2-cyanoethynyl, 3-cyano 1-provinyl, 3-cyano-1-propynyl and 1—Cianault 2—Pentene 4-inyl
  • the above-mentioned lower alkoxy substituted with cyano includes methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentoxy and isopentoxy substituted with 1 to 3 cyano. And the like. Specifically, cyanomethoxy, dicyanomethoxy, tricyanomethoxy, 2-cyanoethoxy, 1,2-dicyanopropyl and the like are preferable.
  • lower alkenyloxy substituted with cyano includes, for example, vinyloxy, aryloxy, 1-propenyloxy, 2-methyl-1-propenyloxy, 1-butenyloxy, substituted with 1 to 3 cyano.
  • lower alkenyloxy such as 2-butenyloxy, 3-butenyloxy and 2-ethyl-1-butenyloxy.
  • lower alkyl substituted with the above-mentioned hydroxy examples include lower alkyl substituted with 1 to 4 hydroxy, specifically, hydroxymethyl, 2-hydroxyl and 1,2-dihydroxyl, and the like. Is mentioned.
  • lower alkenyl substituted with hydroxy examples include lower alkenyl substituted with 1 to 4 hydroxy, specifically, 2-hydroxyvinyl and 3-hydroxy.
  • Examples of the lower alkynyl substituted by hydroxy include lower alkynyl substituted by 1 to 4 hydroxy. Specific examples include 2-hydroxyxetinyl, 3-hydroxy-11-propynyl, 3-hydroxy-12-propynyl, and 1-hydroxy-2-pentene-4-ynyl.
  • Examples of the lower alkoxy substituted with the above-mentioned hydroxy include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, neobutoxy, t-butoxy, pentoxy and isopene substituted with 1 to 4 hydroxy.
  • lower alkoxy such as toxic.
  • 2-hydroxyethoxy, 1,2-dihydroxy-1-n-propyl, 2,3-dihydroxy-1-n-propyl and the like are preferable.
  • the lower alkenyloxy substituted with the above-mentioned hydroxy includes, for example, vinyloxy, aryloxy, 1-propenyloxy, 2-methyl-1-prol substituted with 1 to 4 hydroxy groups.
  • lower alkenyloxy such as niloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy and 2-ethyl-1-butenyloxy.
  • Examples of the lower alkyl substituted with the lower alkoxy include lower alkoxy (eg, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy and t-butoxy). And lower alkyl. Specific examples include methoxymethyl, ethoxymethyl, 2-methoxyethyl and 2-ethoxyxethyl.
  • Examples of the lower alkenyl substituted by the lower alkoxy include lower alkoxy (eg, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy and t-butoxy). And lower alkenyl.
  • lower alkynyl substituted with lower alkoxy examples include lower alkoxy (eg, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy and t-butoxy). And lower alkynyl. Specific examples include 2-methoxetinyl, 3-methoxy-11-propynyl, 3-ethoxy-12-propynyl and 1-ethoxy-12-pentene-4-ynyl.
  • the lower alkoxy substituted with the above lower alkoxy includes, for example, 1 to 4 lower alkoxy (eg, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy and t-butoxy). And lower alkoxy such as methoxy, ethoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, neobutoxy, t-butoxy, pentoxy and isopentoxy. Specific examples include methoxy methoxy, ethoxy methoxy, 2-methoxy ethoxy and 2-ethoxy ethoxy.
  • lower alkenyloxy substituted with the lower alkoxy examples include, for example, lower alkoxy (eg, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy and t-butoxy). Lower-substituted, for example, vinyloxy, aryloxy, 1-propenyloxy, 2-methylol 1-propenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy and 2-ethyl-2-butenyloxy Alkenyloxy Is mentioned.
  • lower alkoxy eg, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy and t-butoxy
  • Lower-substituted for example, vinyloxy, aryloxy, 1-propenyloxy, 2-methylol 1-propenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy and 2-ethyl
  • 2-methoxyethoxyvinyloxy, 3-ethoxyethoxyallyloxy, 3-methoxy-1-propenyloxy, 3-ethoxy-2-methyl-1-propoxycarbonyl , 4-Methoxy-1-butenyloxy, 4-propoxy-12-butenyloxy, 2-methoxy-3-butenyloxy and 4-ethoxy-2-ethyl-1-butenyloxy are preferred.
  • Examples of the above-mentioned lower alkyl substituted with mercapto include lower alkyl substituted with 1 to 4 mercapto. Specific examples include mercaptomethyl, 2-mercaptoethyl and 1,2-dimercaptoethyl.
  • Examples of the lower alkenyl substituted with mercapto include, for example, lower alkenyl substituted with 1 to 4 mercapto. Specifically, 1-mercaptoaryl, 3-mercapto-1-propenyl, 3-mercapto-2-methyl-1,4-butenyl, 4-mercapto-1-butenyl, 4-mercapto-1-butenyl And 1-mercapto-13-butenyl and 4-mercapto-2-ethyl-1-butenyl.
  • lower alkynyl substituted with mercapto examples include, for example, lower alkynyl substituted with 1 to 4 mercapto. Specific examples include 3-mercapto-11-propynyl and 1-1-mercapto-12-pentene-4-ynyl.
  • lower alkoxy substituted with mercapto examples include, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentoxy substituted with 1 to 4 mercapto groups.
  • lower alkoxy such as isopentoxy. Specific examples include 2-mercaptoethoxy and 3-mercaptopropoxy.
  • Examples of the lower alkenyloxy substituted with mercapto include those substituted with 1 to 4 mercapto, for example, vinyloxy, aryloxy, 1-propenyloxy, 2-methyl-1-propenyloxy, 1-butenyloxy, 2—Buteni And lower alkenyloxy such as ruoxy, 3-butenyloxy and 2-ethyl-1-butenyloxy.
  • 3-mercapto-11-propenyloxy, 3-mercapto-1-methyl-1-propenyloxy, 4-mercapto-11-butenyloxy, 4-mercapto-12-butenyloxy, 2-mercapto-13- Butenyloxy and 4-mercapto-1-ethyl-1-butenyloxy are preferred.
  • lower alkyl substituted with the lower alkylthio examples include lower alkyls (eg, methylthio, ethylthio, n-propylthio, isopropylthio, and n-butylthio), and the like. . Specific examples include methylthiomethyl, dimethylthiomethyl, 2-methylthioethyl and 1,2-dimethylthioethyl.
  • lower alkenyl substituted by lower alkylthio examples include lower alkylthio (eg, methylthio, ethylthio, n-propylthio, isopropylthio, and n-butylthio) and the like. No. Specifically, 2-methylthiovinyl, 3-methylthioaryl, 1-methylthioaryl, 3-methylthio-1-propenyl, 3-methylthio-1-methyl-1-propyl, 4-ethylthio-1— Butenyl, 4-methylthio-1-butenyl, 1-methylthio-1-butenyl and 4-ethylthio-12-ethyl-1-butenyl.
  • lower alkylthio eg, methylthio, ethylthio, n-propylthio, isopropylthio, and n-butylthio
  • lower alkynyl substituted with lower alkylthio examples include lower alkylthio (eg, methylthio, ethylthio, n-propylthio, isopropylthio, and n-butylthio) and the like. No. Specific examples include 2-methylthioethynyl, 3-methylthio-11-propynyl, 3-methylthio-12-propynyl, and 1-methylthio-12-pentene-14-ynyl.
  • lower alkylthio eg, methylthio, ethylthio, n-propylthio, isopropylthio, and n-butylthio
  • lower alkoxy substituted with the lower alkylthio examples include lower alkyl Thio (eg, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, etc.) Substituted with 1 to 4, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy And lower alkoxy such as butoxy, pentoxy and isopentoxy. Specific examples include methylthiomethoxy, ethylthiomethoxy, 2-methylthioethoxy, and 3-ethylthiopropoxy.
  • lower alkyl Thio eg, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, etc.
  • 1 to 4 for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy,
  • lower alkenyloxy substituted with lower alkylthio examples include, for example, lower alkylthio (eg, methylthio, ethylthio, n-propylthio, isopropylthio, ⁇ -butylthio, etc.) Lower alkenyloxy such as vinyloxy, aryloxy, 1-propenyloxy, 2-methyl-1-propenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy and 2-ethyl-1-butenyloxy.
  • lower alkylthio eg, methylthio, ethylthio, n-propylthio, isopropylthio, ⁇ -butylthio, etc.
  • Lower alkenyloxy such as vinyloxy, aryloxy, 1-propenyloxy, 2-methyl-1-propenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy and 2-ethyl
  • Lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy and lower alkenyloxy represented by R 1 and R are different from R 3 to R ′, and are different from carboxysyl, lower alkoxycarbonyl, halogenated lower alkoxycarbonyl, lower alkenylo.
  • the number of substituents is 1 to 5, preferably 1 to 3.
  • the substituents may be the same or different.
  • the position of the substituent is not particularly limited. The meanings of the above substituents are the same as described above. No specific examples are given in R for those having a substituent. The following are described below.
  • Examples of the lower alkyl substituted with a carboxyl include a lower alkyl substituted with 1 to 3 hydroxycarbonyl groups. Specific examples include hydroxycarbonylmethyl, 1-hydroxycarbonylethyl and 2-hydroxycarbonylyl.
  • Examples of the lower alkenyl substituted with a carboxyl include lower alkenyl substituted with 1 to 3 hydroxycarbonyls. Specific examples include 2-hydroxycarbonylvinyl, 1-hydroxycarbonylaryl, and 3-hydroxycarbonylaryl.
  • Examples of the lower alkynyl substituted with a carboxyl include lower alkynyl substituted with 1 to 3 hydroxycarbonyls. Specific examples include 3-methoxycarbonyl-2-propynyl, 3-ethoxycarbonyl-111-propynyl, 3-n-propoxycarbonyl-2-propynyl and the like.
  • Examples of the lower alkoxy substituted with a carboxyl include lower alkylthios (eg, methylthio, ethylthio, n-propylthio, isopropylthio, and n-butylthio) substituted with 1 to 5 amino acids such as methoxy, ethoxy, and the like.
  • Lower alkoxy such as propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentoxy and isopentoxy.
  • Specific examples include methylthiomethoxy, ethylthiomethoxy, 2-methylthioethoxy, and 3-ethylthiopropoxy.
  • Examples of the above-mentioned lower alkenyloxy substituted by carboxyl include, for example, vinyloxy, aryloxy, 1-propenyloxy, 2-methyl-1-proxy substituted with 1 to 5 hydroxycarbonyls. Niloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy and 2-ethylyl 1-butyl And lower alkenyloxy such as tenyloxy.
  • Examples of the lower alkyl substituted with a lower alkoxycarboyl include lower alkyl substituted with 1 to 3 lower alkoxycarbonyl. Specific examples include methoxycarbonylmethyl, 1-methoxycarbonylethyl, ethoxycarbonylmethyl and 1-ethoxycarbonylethyl.
  • Examples of the lower alkenyl substituted with the lower alkoxycarbonyl include lower alkenyl substituted with 1 to 3 lower alkoxycarbonyls. Specifically, 2-methoxycarbonylvinyl, 3-methoxycarbonylaryl, 2-ethoxycarbonylvinyl and 3-ethoxycarbonylaryl are exemplified.
  • lower alkynyl substituted by lower alkoxycarbonyl examples include lower alkynyl substituted by 1 to 3 lower alkoxycarbonyl. Specifically, 3-methoxycarbonyl-2-propynyl, 3-ethoxycarbenyl-1-propynyl, 3-n-propoxycarbonyl-2-propynyl and the like can be mentioned.
  • Examples of the lower alkoxy substituted with the lower alkoxycarbonyl include, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, and t-butyl substituted with 1 to 5 lower alkoxycarbonyl. And lower alkoxy such as toxic, pentoxy and isopentoxy. Specifically, methoxycarbonyl methoxy, ethoxycarbonyl methoxy, 2-methoxy Toxylcarbonylethoxy and 3-n-propoxycarbonylpropoxy.
  • lower alkenyloxy substituted with the lower alkoxycarbonyl examples include, for example, vinyloxy, aryloxy, 1-propenyloxy, 2-methyl-1-pro-substituted by 1 to 5 lower alkoxycarbonyls.
  • Alkenyloxy such as di-niloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy and 2-ethyl-1-butenyloxy.
  • Examples of the lower alkyl substituted with the lower alkoxycarbonyl halide include lower alkyl substituted with 1 to 3 halogenated lower alkoxycarbonyl. Specific examples include chloromethoxycarbonylmethyl, 1-chloromethoxycarbonylethyl and 3- (2-chloroethoxycarbonyl) -n-propyl.
  • Examples of the lower alkenyl substituted with a halogenated lower alkoxycarbonyl include lower alkenyl substituted with 1 to 3 halogenated lower alkoxycarbonyls. Specifically, 2-chloromethoxycarbonylvinyl, 3-chloromethoxycarbonylaryl, 3- (2-fluoroethoxycarbonyl) 111-propenyl and 3- (1,2-dichloroethoxycarbonyl) And the like.
  • Examples of the lower alkynyl substituted with a halogenated lower alkoxycarbonyl include lower alkylcarbonyl substituted with 1 to 3 halogenated lower alkoxycarbonyls. Quinyl. Specific examples include 3-fluoromethoxycarbonyl-2-propynyl, 3-chloromethoxycarbonyl-1-propynyl and 1- (2-fluoroethoxycarbonyl) 1-2-pentene-4-ynyl.
  • the lower alkoxy substituted with the lower alkoxycarbonyl described above includes, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-substituted by 1 to 5 lower alkoxycarbonyl.
  • lower alkoxy such as toxic, pentoxy and isopentoxy.
  • Specific examples include methoxycarbonylmethoxy, ethoxycarbonylmethoxy, 2-methoxycarbonylethoxy, and 3-n-propoxycarbonylpropoxy.
  • lower alkenyloxy substituted by lower alkoxycarbonyl examples include, for example, vinyloxy, aryloxy, 1-propenyloxy, 2-methyl-1-substituted by 1 to 5 lower alkoxycarbonyl.
  • lower alkenyloxy such as propenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy and 2-ethyl-1-butenyloxy.
  • Examples of the lower alkyl substituted with the lower alkenyloxycarbonyl include lower alkyl substituted with 1 to 3 lower alkenyloxycarbonyls. Specific examples include vinyloxycarbonylmethyl, 1-aryloxycarbonylethyl, and 3 (1-propenyloxycarbonyl) monopropyl. Examples of the lower alkenyl substituted by the lower alkenyloxycarbonyl include lower alkenyl substituted by 1 to 3 lower alkenyloxycarbonyls. More specifically, 1-vinyloxycarbonylvinyl, 2-vinyloxycarbonylaryl, 3-aryloxycarbonyl-2-propenyl and 3- (1-propenyloxycarbonyl) 1-111 Monopropenyl and the like.
  • the above-mentioned lower alkynyl substituted by lower alkenyloxycarbonyl includes lower alkynyl substituted by 1 to 3 lower alkenyloxycarbonyls. Specifically, vinyloxycarbonyl-2-ethynyl, 3-vinyloxycarbonyl-1-ylpropynyl, 3-aryloxycarbonyl-2-propynyl and 1-aryloxycarbonyl-12-pentene4-11 Inyl and the like.
  • the lower alkoxy substituted with the lower alkenyloxycarbonyl includes, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy substituted with 1 to 5 lower alkenyloxycarbonyl.
  • lower alkoxy such as t-butoxy, pentoxy and isopentoxy.
  • Specific examples include vinyloxycarbonylmethoxy, aryloxycarbonylmethoxy, 2-vinyloxycarbonylethoxy, and 3-aryloxycarbonylpropoxy.
  • Examples of the lower alkenyloxy substituted with the lower alkenyloxycarbonyl include, for example, 1 to 5 lower alkenyloxycarbonyls, for example, vinyloxy, aryloxy, 1-propenyloxy, Lower alkenyloxy such as 2-methyl-1-propenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy and 2-ethyl-1-butenyloxy is exemplified.
  • Examples of the lower alkyl substituted with a lower alkynyloxycarbonyl include lower alkyl substituted with 1 to 5 lower alkynyloxycarbonyls. Specific examples include ethynyloxycarbonylmethyl, 11- (1-propynyloxycarbonyl) ethyl and 3- (2-propynyloxycarbonyl) propyl.
  • lower alkenyl substituted by lower alkynyloxycarbonyl examples include lower alkenyl substituted by 1 to 5 lower alkynyloxycarbonyl. Specifically, ethynyloxycarbonylvinyl, 2-ethynyloxycarbonylaryl, 3- (1-propynyloxycarbonyl) 1-2-propenyl and 3- (2-propynyloxycarbonyl) 1-1- Propenyl and the like.
  • Examples of the lower alkynyl substituted by the lower alkynyloxycarbonyl include lower alkynyl substituted by 1 to 5 lower alkynyloxycarbonyl. Specifically, ethynyloxycarbonyl-2-ethynyl, 3-ethynyloxycarbonyl-2-propynyl, 3- (1-propynyloxycarbonyl) 1-2-propynyl and 1-1 (2-propynyloxycarbonyl) 1-2 —Pentene-4-ynyl and the like.
  • the lower alkoxy substituted with the lower alkynyloxycarbonyl is, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy substituted with 1 to 5 lower alkynyloxycarbonyl. And lower alkoxy such as t-butoxy, pentoxy and isopentoxy. Specifically, ethynyloxycarbonylmethoxy, 1-propynyloxycarbonylmethoxy, 2-ethynyloxycarbonylethoxy and 3- (2 (Propynyloxycarbonyl) propoxy and the like.
  • Examples of the lower alkenyloxy substituted with the lower alkynyloxycarbonyl include, for example, 1 to 5 lower alkynyloxycarbonyl, for example, vinyloxy, aryloxy, 1-propenyloxy, Lower alkenyloxy such as 2-methyl-1-propenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy and 2-ethyl-1-butenyloxy and the like can be mentioned.
  • Examples of the lower alkyl substituted with the optionally substituted phenyloxycarbonyl include, for example, lower alkyl substituted with 1 to 3 optionally substituted phenyloxycarbonyl. No. Specific examples include phenyloxycarbonylmethyl, 1- (4-chlorophenyloxycarbonyl) ethyl and 31- (4-methoxyphenyloxycarbonyl) propyl. Examples of the lower alkenyl substituted with an optionally substituted phenyloxycarbonyl include lower alkenyl substituted with 1 to 3 optionally substituted phenyloxycarbonyl.
  • the above-mentioned lower alkynyl substituted by phenyloxycarbonyl which may be substituted includes 1 to 3 phenyloxycarbonyl which may be substituted. And substituted alkynyl. Specifically, phenyloxycarpoylruetinyl, 3- (4-chlorophenyloxycarbonyl) 1-1 1 propinyl, 3- (4-methoxyphenyloxycarbonyl) 1-2-propynyl and 1-propynyl 1- (2-methoxyphenyloxycarbonyl) -12-pentene-4-ynyl and the like.
  • Examples of the lower alkoxy substituted with the optionally substituted phenyloxycarbonyl include 1 to 5 optionally substituted phenyloxycarbonyl, e.g., methoxy, Lower alkoxy such as ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentoxy and isopentoxy.
  • Specific examples include phenyloxycarbonyl methoxy, 4-chlorophenyloxycarbonyl methoxy, 2- (4-methoxyphenyloxycarbonyl) ethoxy and 3- (4-chlorophenylcarbonylcarbonyl). ) Propoxy and the like.
  • the lower alkenyloxy substituted with the optionally substituted phenyloxycarbonyl includes, for example, 1 to 5 optionally substituted phenyloxycarbonyl, for example, And lower alkenyloxy such as vinyloxy, aryloxy, 1-propenyloxy, 2-methyl-1-propenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy and 2-ethyl-1-butenyloxy.
  • 2-phenyloxycarboxylupinyloxy, 3- (4-methoxyphenyloxycarbonyl) -aryloxy, 3- (4-chlorophenyloxycarbonyl) -111-propenyloxy
  • Examples of the lower alkyl substituted with the optionally substituted rubamoyl include lower alkyl substituted with 1 to 3 optionally substituted rubamoyl. Specific examples include potash-rubamoylmethyl, 11- (potash-rubamoyl) ethyl and 3- (potash-rubamoyl) propyl.
  • Examples of the lower alkenyl substituted with the optionally substituted rubamoyl include lower alkenyl substituted with 1 to 3 optionally substituted rubamoyl. Specific examples include potash-rubamoyl vinyl, 2- (potash-rubamoyl) aryl, 3- (potash-rubamoyl) 1-2-propenyl, and 3- (potash-rubamoyl) 111-propenyl.
  • Examples of the lower alkynyl substituted with the optionally substituted rubamoyl include lower alkynyl substituted with 1 to 3 optionally substituted rubamoyl. Specific examples include sorbamoylethynyl, 3- (rumbamoyl) 1-1-propynyl, 3- (rumbamoyl) -2-propynyl and 1- (carbamoyl) 1-2-pentene-14-ynyl, etc. Is mentioned.
  • the lower alkoxy substituted with the optionally substituted carbamoyl includes, for example, methoxy, ethoxy, propoxy, isopropoxy, substituted with 1 to 5 optionally substituted rubamoyl. And lower alkoxy such as butoxy, isobutoxy, s_butoxy, t-butoxy, pentoxy and isopentoxy. Specifically, there are potato rubamoyl methoxy, 4 potato rubamoyl methoxy, 2- (potato rubamoyl) ethoxy, and 3- (potato rubamoyl) propoxy.
  • Examples of the lower alkenyloxy substituted with the optionally substituted carbamoyl include, for example, vinyloxy, aryloxy, and 1-pro substituted with 1 to 5 optionally substituted rubamoyl. Dinyroxy, 2-methyl-1-propenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyl And C2-C7 alkenyloxy, such as hydroxy and 2-ethyl-1-butenyloxy.
  • Examples of the lower alkenyl substituted with an optionally substituted phenyl include lower alkenyl substituted with one to three optionally substituted phenyl. Specifically, phenylvinyl, 2- (4-chlorophenyl) aryl, 3- (4-methoxyphenyl) 1-2-propenyl and 3- (4-methoxyphenyl) 1-1-1 And propenyl.
  • the above-mentioned lower alkynyl substituted with phenyl which may be substituted includes lower alkynyl substituted with 1 to 3 phenyl which may be substituted. Specifically, phenylechinyl, 3- (4-chlorophenyl) -l-piper, 3- (4-methoxyphenyl) 1-2-propynyl and 1- (4-methoxyphenyl) 1-2 —Pentene 4-inyl and the like.
  • the lower alkoxy substituted with the optionally substituted phenyl includes, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, substituted with 1 to 5 phenyl which may be substituted. And lower alkoxy such as isobutoxy, s-butoxy, t-butoxy, pentoxy and isopentoxy. Specifically, phenylmethoxy, 4-methoxyphenylmethoxy, 2- (4-chlorophenyl) ethoxy, and 3- (3-methoxyphenyl) propoxy. And so on.
  • Examples of the lower alkenyloxy substituted with an optionally substituted phenyl include, for example, 1 to 5 phenyl optionally substituted, for example, vinyloxy, aryloxy, Lower alkenyloxy such as niloxy, 2-methyl-1-propenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy and 2-ethyl-1-butenyloxy.
  • lower alkyl substituted with lower alkylcarbonyloxy examples include lower alkyl substituted with 1 to 3 lower alkylcarbonyloxy. Specific examples include methylcarbonyloxymethyl, 2-methylcarbonyloxyethyl, ethylcarbonylcarbonylmethyl and 2-ethylcarboxyloxyethyl.
  • lower alkenyl substituted by lower alkylcarbonyloxy examples include lower alkenyl substituted by 1 to 3 lower alkylcarbonyloxy. Specific examples include 2-methylcarbonyloxyvinyl, 1-methylcarboxyloxyaryl, 2-ethylcarbonyloxyvinyl and 1-ethylcarboxyloxyaryl.
  • lower alkynyl substituted by lower alkylcarbonyloxy examples include lower alkynyl substituted by 1 to 3 lower alkylcarbonyloxy. Specifically, 3-methylcarbonyloxy-1-propynyl, 3-ethylcarbonyloxy-1-propynyl and 3-n-propylcarbonyloxy — 1 — propynyl and the like.
  • lower alkoxy substituted with lower alkylcarbonyloxy examples include those substituted with 1 to 5 lower alkylcarbonyloxy, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s — And lower alkoxy such as butoxy, t-butoxy, pentoxy and isopentoxy.
  • Specific examples include methylcarbonyloxymethoxy, ethylcarbonyloxymethoxy, 2-methylcarbonyloxyethoxy, and 3-n-propylcarbonyldioxypropoxy.
  • lower alkenyloxy substituted with lower alkylcarbonyloxy examples include, for example, vinyloxy, aryloxy, 1-propenyloxy, 2-substituted by 1 to 5 lower alkylcarbonyloxy, Alkenyloxy such as methyl-1-pronenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy and 2-ethyl-1-butenyloxy.
  • n represents an integer of any of 0 to 4, but when n is 2 or more, R 3 may be different. Preferably, it is 0 or 1.
  • the compound of the present invention has an asymmetric carbon, its optically active and racemic forms are also included in the compound of the present invention.
  • the compounds of the present invention may further form salts at the amine moiety.
  • a chemically acceptable salt is preferable.
  • salts with organic acids examples include salts with hydrochloric acid, hydrofluoric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid, perchloric acid, hydroiodic acid, and the like.
  • Salts with organic acids include formic acid, acetic acid, trifluoroacetic acid, fumaric acid, oxalic acid, tartaric acid, maleic acid, cunic acid, succinic acid, malic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, methanesulfone Examples include salts with acids, p-toluenesulfonic acid, and benzenesulfonic acid.
  • the hydrate of the compound (I) of the present invention is preferably a chemically acceptable hydrate, and also includes a hydrate. Specific examples include monohydrate, dihydrate and hexahydrate. These salts and hydrates can be prepared according to a conventional method.
  • Compound (I) of the present invention [that is, a compound represented by the general formula (I). Hereinafter, the compounds represented by other formulas may be abbreviated similarly. ] Can be produced, for example, by a synthetic route shown below.
  • the compound represented by the general formula (Ilia) can be produced by reacting the compound (IV) with the compound (V) in an appropriate solvent.
  • the compound (V) used as a raw material in this reaction was Org. Synth. Collect. Vol. According to the method of 735 (1965), it can be produced by reacting the corresponding acid chloride or acid bromide with ammonium thiocyanate or potassium thiocyanate in a suitable solvent.
  • Compound (IV) used as a starting material in this reaction was produced according to the method of Synthesis 880 (1989), Chem. Pharm. Bull. 32, 2421 (1984), Chem. Pharm. Bull. 32, 4907 (1984), etc. can do.
  • compound (IV) can be used in an amount of 1 equivalent or more, preferably 1 to 3 equivalents, relative to compound (V).
  • Solvents that can be used include aromatic hydrocarbons (eg, toluene, benzene, xylene, etc.), ethers (eg, tetrahydrofuran, getyl ether, dioxane, etc.), halogenated hydrocarbons (chloride, etc.). Methylene, chloroform, 1,2-dichloroethane, etc., esters (ethyl acetate, etc.), nitrils (acetonitryl, etc.), ketones (acetone, 2-butynone, etc.), Examples include amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.) and their mixed solvents.
  • aromatic hydrocarbons eg, toluene, benzene, xylene, etc.
  • ethers eg, tetrahydrofuran, getyl ether, dioxane, etc.
  • halogenated hydrocarbons chloride, etc
  • the reaction temperature is from 0 to 150 ° C, preferably from 15 to 100 ° C.
  • the reaction time varies depending on the compound, but is 5 minutes to 2 hours, preferably 15 minutes to 1 hour.
  • the obtained compound (Ilia) can be used in the next step after purification by a reaction method or a crude product, or by a conventional method (eg, column chromatography, recrystallization, etc.).
  • compound (I) can be produced by reacting compound (Ilia) in the presence or absence of a base in an appropriate solvent.
  • bases examples include alkali metal hydrides (such as sodium hydride), alkali metal alkoxides (such as sodium methoxide, sodium ethoxide, potassium t-butoxide), and alkali inorganic substances (such as carbonate).
  • alkali metal hydrides such as sodium hydride
  • alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide
  • alkali inorganic substances such as carbonate.
  • Sodium, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, etc., and amines (triethylamine, pyridine, etc.) the amount of which is 1 to 3 equivalents to (II), preferably. Is 1-2 equivalents.
  • Solvents that can be used include, for example, aromatic hydrocarbons (benzene, toluene, xylene, etc.), halogenated hydrocarbons (methylene chloride, chloroform, 1,2-dichloroethane, etc.), ethers (tetrahydrofuran) , Dioxane), alcohols (methanol, ethanol, n-propanol, isopropanol, etc.), esters (ethyl acetate, etc.), nitriles (acetonitrile, etc.), ketones (acetone, 2- Amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), water and their mixed solvents.
  • aromatic hydrocarbons benzene, toluene, xylene, etc.
  • halogenated hydrocarbons methylene chloride, chloroform, 1,2-dichloroethane, etc.
  • ethers tetrahydrofuran
  • the reaction temperature is from 0 to 150 ° C, preferably from 20 to 100 ° C.
  • the reaction time is generally 15 minutes to 24 hours, preferably 30 minutes to 6 hours.
  • the obtained compound (I) can be purified by a conventional method (eg, column chromatography, recrystallization, etc.).
  • compound (I) can be produced from compound (V I) and compound (V I I) in the presence of a base in a suitable solvent.
  • compound (VII) can be used in an amount equivalent to or more than compound (VI).
  • bases examples include alkali metal hydrides (such as sodium hydride) and alkali metal alkoxides (such as sodium methoxide, sodium ethoxide, potassium t-butoxide), and the like.
  • the amount used is 1 to 3 equivalents, preferably 1 to 2 equivalents, relative to (V).
  • Solvents that can be used include, for example, aromatic hydrocarbons (benzene, toluene, xylene, etc.), ethers (tetrahydrofuran, dioxane, etc.), amides (N, N-dimethylformamide, N, N —Dimethylacetamide, etc.) and their mixed solvents.
  • aromatic hydrocarbons benzene, toluene, xylene, etc.
  • ethers tetrahydrofuran, dioxane, etc.
  • amides N, N-dimethylformamide, N, N —Dimethylacetamide, etc.
  • the reaction temperature is from 0 to 150 ° C, preferably from 20 to 100 ° C.
  • the reaction time is generally 0.5 to 24 hours, preferably 1 to 12 hours.
  • the obtained compound (I) can be purified by a conventional method (eg, column chromatography, recrystallization, etc.).
  • compound (la) can be produced from compound (VIII) and compound (VIII) in the presence of a base in a suitable solvent.
  • the compound (VII) can be used in an amount of 2 equivalents or more based on the compound (VIII).
  • Examples of the base that can be used include alkali metal hydrides (such as sodium hydride) and alkali metal alkoxides (such as sodium methoxide, sodium ethoxide, potassium t-butoxide).
  • the amount is 2 to 6 equivalents, preferably 2 to 4 equivalents, relative to (VII).
  • Examples of usable solvents include aromatic hydrocarbons (benzene, toluene, xylene, etc.), ethers (tetrahydrofuran, dioxane, etc.), amides (N, N-dimethylformamide, N, N —Dimethylacetamide, etc.) and their mixed solvents.
  • the reaction temperature is from 0 to 150 ° C, preferably from 20 to 100 ° C.
  • the reaction time is generally 0.5 to 24 hours, preferably 1 to 12 hours.
  • the resulting compound (la) can be purified by a conventional method (eg, column chromatography, recrystallization, etc.).
  • the compound (I) of the present invention exhibits excellent herbicidal activity at a low dose in paddy fields, especially against evening radish, which is a highly damaging weed in paddy fields, and has very little phytotoxicity to paddy rice. It also has a strong herbicidal effect against broadleaf weeds such as cyperaceae and broadleaf weeds such as oak, azaena, and red rush.
  • the compound (I) of the present invention is used as a herbicide, for example, Shiroza, Akaza, Koazaka, Keariyuso, etc., for the Akazaceae, Yaemdara, Hexokazura, Akane, etc. for the Akanetaceae, and Dinugarashi, Suzuki for the Brassicaceae.
  • Ascendaceae Echinacea japonica, Enokigusa, Enokigusa, etc.
  • Ascendaceae such as horsetail and linseed, etc., Solanaceae as perennial, etc .
  • the convolvulaceae such as sarcophagid and pedunculus
  • the convolvulaceae include convolvulus, the convolvulaceae, the pear squid, the American reed pear, the convolvulaceae, etc.
  • the compound (I) of the present invention has an excellent growth regulating action (eg, growth inhibitory action) on grasses and broadleaf weeds, particularly lawns and levee weeds as described above, and It is possible to suppress the growth of grass height on grass such as shores and golf courses for a long time.
  • growth regulating action eg, growth inhibitory action
  • a useful plant such as corn, sugar cane, sorghum, rice, wheat, oats, soybean, peanut, peta, etc. It shows little phytotoxicity and is easily recoverable even in the presence of phytotoxicity.
  • compound (I) can be used in fields, paddy fields, orchards, tea fields, mulberry fields, fallow fields, pastures, and other agricultural fields, as well as railroads, roads, lawns, industrial sites, riverbeds, residential lands, parks, forests, It can be used as a selective or non-selective herbicide or as a growth regulator (eg, a growth inhibitor, a mowing alleviator, a lodging alleviator, etc.) on non-agricultural land such as a newly constructed land or abandoned open space.
  • a growth regulator eg, a growth inhibitor, a mowing alleviator, a lodging alleviator, etc.
  • compound (I) when used as a herbicide, it can be mixed with various carriers depending on the use, and used as, for example, granules, wettable powders, emulsions, suspensions and the like.
  • the embodiments described above comprise at least one compound of the invention and suitable solid or liquid carriers and, if desired, suitable auxiliaries for improving the dispersibility and other properties of the active substance.
  • suitable auxiliaries for improving the dispersibility and other properties of the active substance.
  • a surfactant, a spreading agent, a dispersing agent, a stabilizing agent, an emulsifying agent, a suspending agent, a penetrating agent, a wetting agent, etc. can be obtained by a usual method.
  • solid carriers or diluents include botanicals (eg, cereal flour, coconut stalk flour, soy flour, walnut husk flour, vegetable flour, canna flour, bran, bark flour, fibrous flour, Vegetable extract residue), fibrous substances (eg, paper, cardboard, rags), artificial plasticity Powder, clay (eg, kaolin, diatomaceous earth, bentonite, clay, clay), talc and inorganic substances (pyroxene, sericite, pumice, sulfur powder, activated carbon), chemical fertilizers (eg, ammonium sulfate, ammonium phosphate, nitric acid) Ammonium, urea, ammonium chloride).
  • botanicals eg, cereal flour, coconut stalk flour, soy flour, walnut husk flour, vegetable flour, canna flour, bran, bark flour, fibrous flour, Vegetable extract residue
  • fibrous substances eg, paper, cardboard, rags
  • artificial plasticity Powder eg, clay (eg,
  • liquid carriers and diluents include water, alcohols (eg, methanol, ethanol), ketones (eg, acetone, methyl ethyl ketone), ethers (eg, Jethyl ether). , Dioxane, cellosolve, tetrahydrofuran), aromatic hydrocarbons (eg, benzene, toluene, xylene, methyl naphthylene), aliphatic hydrocarbons (eg, gasoline, kerosene, kerosene), esters, nitriles, Acid amides (eg, N, N-dimethylformamide, N, N-dimethylacetamide), halogenated hydrocarbons (eg, 1,2-dichloroethane, carbon tetrachloride), solvent naphtha, cyclohexane, etc. is there.
  • alcohols eg, methanol, ethanol
  • ketones eg, acetone, methyl
  • surfactants include alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, polyethylene glycol ethers, polyalcohol esters, and the like.
  • spreading or dispersing agents include casein, gelatin, starch, carboxymethylcellulose, acacia, alginic acid, lignin, bentonite, molasses, polyvinyl alcohol, pine oil and agar.
  • Stabilizers include PAP (isopropyl phosphate mixture), tricresyl phosphate (TCP), tall oil, epoxy oil, surfactants, fatty acids and their esters.
  • the preparation of the present invention can be used in combination with a fungicide, an insecticide, an acaricide, or a fertilizer, a soil treating agent (improving agent), or the like.
  • a fungicide such as MCP, CNP, IPC, Ashram, arachlor, trifluralin, etc.
  • MCP herbicide
  • CNP CNP
  • IPC Ashram
  • arachlor trifluralin
  • trifluralin etc.
  • the application rate of the herbicide containing the compound of the present invention depends on weather conditions, soil conditions, formulation, Depending on the type of the target weed, the application time, the combination of the composition, etc., the above-mentioned preparation generally contains at least one compound represented by the general formula (I) of the present invention in an amount of 0.1 to 95% by weight. Preferably, it contains 1.0 to 80% by weight. These preparations can be used alone or in a diluted form.
  • the compound of the present invention can be applied in an appropriate amount of 0.05 to 10 kg, preferably 0.1 to 1.0 kg, as an active ingredient per hectare. 5 kg.
  • H- NMR (CD C 1 3) values given in the examples was measured at 2 7 0 MH z, expressed in heavy black port Holm, value Te tetramethyl silane as an internal standard (p pm). Coupling constants (J) are indicated by Hz. De — In the evening, s means singlet, d means doublet, t means triplet, q means quadruplex, m means multiplet, and brs means wide singlet.
  • 2-Promobutyryl bromide was prepared by dissolving 0.84 g (0.011 mol) of ammonium thiocyanate in 10 ml of acetone and 5 ml of acetone under ice cooling.
  • N, N-Dimethylformamide 2 in 10 m 1 (dihidro 1,4,4-benzoxazine-1,4-yl) 1,5-ethyl 4- (5H) monothiazolone 1.25 g (0. 0 048 mo 1) and 1-promo 2-chloroethane 2.05 g (0.01 43 mo 1) are dissolved and sodium hydride 0.38 g (0, 0 0 95 mol ) was added. The mixture was stirred overnight at room temperature. After the reaction, the reaction solution was added to 50 ml of ice water, adjusted to pH 3 or less with 6 N hydrochloric acid, and extracted with 50 ml of ethyl acetate.
  • No in the test examples described below is represented by a compound number according to the combination shown in A to T in Table 1, a to z in Table 2, and 1 to 101 in Tables 3 to 5.
  • test compound 3 g of the test compound, 3 g of polyoxyethylene alkyl sulfate, 2 g of calcium lignin sulfonate, 20 g of bentonite and 72 g of kaolin Klein, then granulated and hayed, 3% granules was adjusted.
  • Paddy soil is packed in a 7.1 X 7.1 cm square pot, and 10 seeds / pot is seeded for evening vines and corn, and 5 grains are seeded for Yinho evening and 3 pots are immersed in 3 cm. Water was added, and immediately a treatment solution (0.7 ml / pot) of a predetermined amount was dropped.
  • the treatment solution was prepared by dissolving the test compound in a small amount of acetone and diluting it with distilled water containing a surfactant to a predetermined concentration. After the treatment, the plants were maintained in a greenhouse for 21 days to investigate the herbicidal effect and evaluated according to the following criteria.
  • Paddy soil is filled in a 7.1 x 7.1 cm square pot, and seeds of 10 varieties / pot are distributed for Tainubie and konagi, and 5 grains / pot are sown for Yinhoyui and 3 cm inundation.
  • the treatment solution (0.7 mlZ pot) at a predetermined dose was dropped.
  • the treatment solution was prepared by dissolving the test compound in a small amount of acetone and diluting it with distilled water containing a surfactant to a predetermined concentration. After the treatment, the plants were maintained in a greenhouse for 21 days, the herbicidal effects were investigated, and the evaluation was performed according to the same criteria as in Test Example 1.
  • the thiazolone derivative having a fused polycyclic hetero ring at the 2-position of the present invention is useful as an agricultural chemical, particularly as a herbicide.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
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  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention porte sur des composés pouvant servir d'herbicides, de formule générale (I) dans laquelle (a) représente un groupe hétérocyclique polycyclique substitué préparationsentant comme atome constitutif un atome d'azote en position 2 du cycle thiazolone, R1 et R2 représentent chacun indépendamment H, halogéno, cyano, phényle facultativement substitué, alkoxycarbonyle inférieur, alkoxycarbonyle inférieur halogéné, alcényloxycarbonyle inférieur, phényloxycarbonyle facultativement substitué, carbamoyle ou alkyle inférieur facultativement substitué alcényle inférieur, alkynyle inférieur, alkoxy inférieur ou alcényloxy présentant facultativement un substituant spécifique, ou dans laquelle R1 et R2 peuvent former ensemble un cycle avec l'atome de carbone contigu.
PCT/JP1999/006316 1998-11-17 1999-11-12 Derives de la thiazolone presentant un heterocycle polycyclique en position 2, et pesticides le contenant comme ingredient actif WO2000029410A1 (fr)

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JP10/326583 1998-11-17
JP32658398 1998-11-17

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0004129A2 (fr) * 1978-02-17 1979-09-19 Imperial Chemical Industries Plc Dérivés de thiazolidinone, procédé pour leur préparation, compositions pesticides les contenant et procédés pour le traitement des plantes
US4208327A (en) * 1979-04-03 1980-06-17 G. D. Searle & Co. 5-Aryl-1-(2-oxazolin-2-yl)-1H-1,4-benzodiazepines and related compounds

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0004129A2 (fr) * 1978-02-17 1979-09-19 Imperial Chemical Industries Plc Dérivés de thiazolidinone, procédé pour leur préparation, compositions pesticides les contenant et procédés pour le traitement des plantes
US4208327A (en) * 1979-04-03 1980-06-17 G. D. Searle & Co. 5-Aryl-1-(2-oxazolin-2-yl)-1H-1,4-benzodiazepines and related compounds

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