WO1998011079A1 - Derives d'isoxazolinone et compositions herbicides - Google Patents

Derives d'isoxazolinone et compositions herbicides Download PDF

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Publication number
WO1998011079A1
WO1998011079A1 PCT/JP1997/003210 JP9703210W WO9811079A1 WO 1998011079 A1 WO1998011079 A1 WO 1998011079A1 JP 9703210 W JP9703210 W JP 9703210W WO 9811079 A1 WO9811079 A1 WO 9811079A1
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Prior art keywords
group
lower alkyl
general formula
alkyl group
substituted
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PCT/JP1997/003210
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English (en)
Japanese (ja)
Inventor
Ken Morita
Toshiharu Ohno
Tsunehiro Kido
Kazuo Hirayama
Hiroyuki Okita
Yoshihisa Watanabe
Hirokazu Yoshizawa
Masahide Onoe
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Hokko Chemical Industry Co., Ltd.
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Priority to AU42196/97A priority Critical patent/AU4219697A/en
Publication of WO1998011079A1 publication Critical patent/WO1998011079A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D261/12—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to a novel isoxazolinonone derivative having herbicidal activity, and more particularly, to a novel 2- (N, N-disubstituted cal yarn).
  • the present invention relates to a herbicide characterized by containing a sodium soxazolinone derivative as an active ingredient. Therefore, the present invention is useful in the chemical industry and agriculture, particularly in the field of agrochemical manufacturing.
  • R> represents a lower alkyl group, a lower alkyl group, Lower alkylene group, halogen-substituted lower alkyl group, halogen-substituted lower alkyl group, lower alkoxy-substituted lower alkyl group, phenoxy-substituted group It indicates etc. lower ⁇ Honoré key le group, m indicates 0 or 1, n indicates 0, 1 or 2, R 2 is a hydrogen atom or indicates lower a Le key Le radical, R 3 represents a lower alkyl group, a lower alkyl group, etc., and R 4 is a lower alkyl group, a lower alkyl group, a benzyl group, a substituted phenyl group.
  • Y and Z may be the same or different and each represent an oxygen atom or a sulfur atom (JP-A-5-39275) reference).
  • Ri represents a hydrogen atom or a halogen atom
  • R 2 represents an alkynole group, a cycloalkynole group, a lower alkenyl group, a substituted benzyl group.
  • R 3 and R 4 is each der Ri each lower a Luque group
  • Ru Ah is R: $ is and indicates a lower alkyl group
  • R 4 is A compound represented by a halogen-substituted phenyl group, and A represents a sulfur atom, a sulfinyl group or a snorrenol group (JP-A-60-104074) Reference).
  • R 2 represents an alkyl group, a lower alkyl group, a lower alkyl group, a substituted alkyl group, Represents an aralkyl group or an aryl group which may be substituted, and A represents a sulfur atom, a sulfinyl group or a sulfonyl group ) (See JP-A-58-194869).
  • R i represents a halogen atom
  • R 2 represents a lower alkyl group
  • R 3 and R 4 are the same or different from each other, and each represents a lower alkylene group.
  • a cycloalkyl group, a phenyl group or a benzyl group (see JP-A-51-44637).
  • R i represents a hydrogen atom, a lower alkyl group or a halogen atom
  • R 2 represents a hydrogen atom or a lower alkyl group
  • R 3 and R 4 are the same or different. And each represents a lower phenol group
  • X represents a halogen atom
  • Y represents a lower phenol group
  • Ri represents a lower phenol group, an alkenyl group or a phenol group
  • R 2 represents a halogen radical
  • X represents a halogen atom
  • Y represents a lower alkyl group
  • Ri represents a lower alkylene group, an phenol group or a phenol group
  • R 2 represents a halogeno group.
  • X represents a halogen atom
  • ⁇ represents a lower alkynole group
  • R 1 represents a lower alkynole group, an anorecheninole group or an anolexinyl group
  • R 2 represents a quinolenyl group. And a phenol group
  • X represents a halogen atom
  • Y represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms
  • Ri represents a lower alkyl group or a lower alkenyl group having 1 to 4 carbon atoms
  • R 2 is a compound represented by a lower alkynole group or a lower anorecenyl group having 1 to 4 carbon atoms, or a phenyl group substituted with a halogen atom.
  • R2 represents a hydrogen atom or a straight chain such as a methyl, ethyl, bromo, isopropynole, butyl or tert-butynole group.
  • a lower or branched lower alkyl group or a phenyl group, or Ri and R 2 may be bonded to each other to form a benzene ring;
  • 3 represents a linear or branched lower alkyl group or a benzyl group such as a methylenol group, an ethyl group, a propynolene group, an isopropyl group, and a butyl group.
  • M is 0 or an integer of 1 to 2;
  • R 1 represents a hydrogen atom, a hydrogen atom, a halogen atom or an alkyl group
  • R 2 represents a hydrogen atom, an anoalkyl group or a substituted or unsubstituted phenyl group.
  • R i and R 2 may bond to each other to form a benzene ring
  • R 3 may be a substituted or unsubstituted azorealkyl group
  • R 4 represents a substituted or unsubstituted alkanol group, an alkanol group, an alkanol group, or an alkynol group.
  • X is preferably an oxygen atom or a sulfur atom) (see Japanese Patent Publication No. 49-72252).
  • X represents a halogen atom, a lower alkyl group or a hydrogen atom
  • Y represents a hydrogen atom or a lower alkyl group
  • X represents a halogen atom or a lower alkyl group.
  • R 2 represents a lower alkyl group, a cycloalkyl group, etc.
  • R 2 represents a substituted or unsubstituted phenyl group or a substituted or unsubstituted benzyl group (see JP-A-49-62636).
  • R! Represents a halogen atom, a lower alkyl group or a hydrogen atom
  • R 2 represents a hydrogen atom, a lower alkyl group, an alkoxycarbonyl group or a phenyl group.
  • R 3 and R 4 depends Ah Ru or phase of the same, respectively a lower alkyl group, shea click b a alkyl or a group or full E group, Oh Ru les, the R 3 And R4 combine with each other to form a single ring
  • R! Is a hydrogen atom, a lower A alkyl group or indicates Ha B gain NHara child
  • R 2 is shows a hydrogen atom or a lower alkyl group
  • R 3 is a hydrogen atom, a lower A Le key A lower phenol group, a lower phenol group, a lower phenol group, or a phenylene group which may have a halogen atom substitution group in the phenyl ring.
  • R 3 may have a substituent such as a lower phenolic group, a halogen atom, a nitro group, or a lower alkoxy group. Which represents a group) (see Japanese Patent Publication No. 46-24272).
  • R! Represents a lower alkyl group or a furyl group which may be substituted with a halogen atom
  • R 2 represents a hydrogen atom, a lower alkyl group or A halogen atom
  • R 3 represents a hydrogen atom, a lower alkyl group, a lower alkoxycarbonyl group, a lower dianoxycarbonyl group, an amino group, or (Indicating a phenyl group) (see Japanese Patent Publication No. 45-10144), (17)
  • X represents a hydrogen atom, a lower phenol group or a halogen atom
  • Y represents a hydrogen atom, a lower alkyl group or a phenyl group
  • R i represents And R 2 are a lower alkyl group, a dialkoxy quinole group, an alkanol carbonyl group, a cycloalkyl group, a cycloalkyl group, and an alkyl group
  • R 2 represents a hydrogen atom, a halogen atom or an alkyl group
  • R 2 represents a hydrogen atom, an alkynole group, an alkanol group, a dialkoxyalkyl group or an aryl group.
  • R 2 and R 3 may be bonded to each other to form a benzene ring, or R 3 may be a benzoyloxy group, substituted or unsubstituted. ⁇ , ary — roxoxy group, N-substituted or N, N-disubstituted amino group, etc.
  • X represents an oxygen atom or a sulfur atom
  • herbicidal compounds In the development of new herbicides, selective and desirable herbicidal activities based on useful cultivated plants, i.e. differences in sensitivity to the drug between the crop and the weeds, etc. It is important to create new compounds that exhibit a sufficiently high herbicidal effect over a period of time. In other words, herbicidal compounds have a high herbicidal effect but can cause phytotoxicity to crops, or have a low herbicidal effect on crops but have a short-lasting herbicidal effect. Therefore, as a herbicide, it is difficult to say that it is not necessarily satisfactory in practical use.
  • the known isoxoxazolinone compounds described in the documents described in the above (1) to (: 18) have a herbicidal effect when used as a herbicide, as shown in the test examples described below. Is insufficient in some cases, or causes phytotoxicity to crops, or the persistence of the herbicidal effect is insufficient. It is not satisfactory as an active ingredient in herbicides.
  • the present invention provides excellent herbicidal activity and safety to crops in place of these known isoxosazolins.
  • the present inventors have synthesized a number of novel isoxazolinonone derivatives in order to achieve the above-mentioned object, and have intensively studied their herbicidal activity and practical utility.
  • a novel isoxazolinonone derivative generally represented by the following general formula (I) can be used for crops such as rice, wheat, barley, soybean, and corn.
  • novel isoxazozolin derivatives of the general formula (I) are effective against various major weeds in upland crops such as wheat, barley, maize and the like. It has been found that they show an excellent herbicidal effect at all. Based on these findings, the present invention has been completed.
  • R represents a hydrogen atom or a lower alkyl group
  • R 2 represents a lower alkyl group, a lower alkyl group, a lower alkyl group, Cycloalkyl group having 3 to 7 carbon atoms, phenolic-lower alkyl group, lower alkoxyalkyl group, lower cyanoalkyl group or benzyl group
  • a benzene ring of the group may be substituted with a halogen atom, a lower alkyl group or a lower phenol group
  • R 3 is a lower group.
  • m represents 0 or an integer of 1 to 5, preferably 0 or an integer of 1 to 3, and Y is the same or different.
  • Halogen atom, lower alkyl group, halo-lower alkyl group, lower alkoxy group olevonyl group, lower anorecanyl group, lower anoreoxy group, halo-lower alkoxy group Represents a substituted or unsubstituted phenyl group represented by the formula:
  • X may be the same or different, and may be a halogen atom, a lower alkyl group, a mouth-lower alkyl group, or a lower alcohol group.
  • W may be the same or different, and may be a hydrogen atom, a halogen atom, a lower alkyl group, a mouth-lower alkyl group, or a lower alkyl group.
  • R 5 is a lower phenyl group or a phenyl group, a is an integer of 1 to 2, and E may be the same or different; Represents a hydrogen atom, a halogen atom, a lower alkyl group, a c-lower alkyl group, a lower alkoxy group, or a c-lower alkyl group; Is an integer of 0 or 1) or a heterocyclic group-substituted methyl group, or (iv) Q is
  • R 6 is a lower alkoxy group] or a lower alkoxy carbonyl group represented by the following formula: 0
  • R 7 is a hydrogen atom or a lower alkyl group
  • R 8 is a hydrogen atom, a lower alkyl group or a phenyl group.
  • RR 2 , R 3 , R 4 , Rs, R 7, R 8 , E, X or Y or W represented by the general formula (I) is a lower alkyl group.
  • the lower alkyl group include a methyl group, an ethyl group, an n-propynole group, an isopropynole group, an n-butyl group, an isobutyl group, an s-butyl group, and a t-butyl group.
  • n-pentynole group iso-pentyl group, 2-methylbutyl group, neopentyl group, n-hexynole group, 4-methynolepentyl group, 3-methylpentynole group, 2-methylopenole group Methyl group, 3,3-dimethylbutyl group, 2,2-dimethylbutyl group, 1, dimethylbutylene group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group Group, 2,3-dimethylbutyl group, 1-ethynole-butyl group, 1-ethyl-2-methyl-propyl group, 2-methyl-1-ethylpropyl group Let's Do, Ru can and this Ru alkyl der carbon number 1-6 straight-chain or branched.
  • R 2 or R 3 represented by the above general formula (I) is a lower alkenyl group
  • the lower alkenyl group is, for example, a vinyl group, a 1-pro Benzyl group, 2-propyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 2-ethyl-2-propyl Mouthyl group, 2-butenyl group, 1-methynolebutenyl group, 2-methynole-2-buteninole group, 1-ethyl-2-buteninole group, 3-butenyl group, 2-pentenole, 3-pentenyl, 4-pentenole, 2-hexenyl, 3-hexenyl, 4-hexenyl
  • Such a alkenyl group may be a linear or branched alkenyl group having 2 to 6 carbon atoms.
  • R 2 or R 3 represented by the above general formula (I) is a lower alkynyl group
  • the lower alkynyl group is, for example, a 2-propynyl group , 1-methyl-2-propyninole, 2-butynyl, 1-methylbutynyl, 1-ethyl-2-butynyl, 3-butynole, 2-methyl-3-butyninole Group, 2-pentynyl group, 4-pentynyl group, 2-hexenyl group, 3-hexynyl group, 4-hexynyl group, 5-hexynyl group
  • Such a straight-chain or branched-chain alkynyl group having 3 to 6 carbon atoms can be used.
  • R 2 in the general formula (I) is a cycloalkyl group having 3 to 6 carbon atoms
  • the lower cycloalkyl group is, for example, a cyclopropynole group, Cyclobutyl group, cyclopentinole group, cyclohexenole group, 2-methylenopropyl group, 2-methylone mouth mouth Pentinole group, 2-methylone mouth mouth It can be a cycloalkyl group having 3 to 7 carbon atoms, which may have a side chain, such as a group.
  • halogen atom is fluorine, chlorine, bromine or iodine. You can.
  • R 2 , X, Y or W or E shown in the above general formula (I) is a non-open-lower alkyl group, it is, for example, a trif-norelomethyi.
  • X, Y, W or E in the general formula (I) is a lower alkoxy group, it may be, for example, a methoxy group, an ethoxy group, an n-proboxy group.
  • X, Y, W or E in the general formula (I) is a halo-lower alkoxy group, it may be, for example, a difluoromethoxy group, a trifluorene group. It can be a haloalkoxy group having 1 to 6 carbon atoms, such as a methoxy group or a 2,2,2-trino-oleoxy ethoxy group. Wear.
  • the lower alkoxyalkyl group may be, for example, For example, methoxymethyl group, ethoxymethyl group, ethoxymethyl group, n-propoxymethyl group, n-butoxymethyl group, n . It can be a phenolic alkoxy group in which a lower alkyl group having 1 to 4 carbon atoms is bonded to a lower alkyl group, such as a poxyl group.
  • R 2 shown in the general formula (I) is a lower cyanoalkyl group
  • it is, for example, a cyanomethyl group, a cyanoethynole group, a 2-cyanoethynole group, A straight-chain or branched-chain cyanoalkyl group having 2 to 5 carbon atoms, such as a cyanopropyl group, a 2-cyanopropyl group or a cyanobutyl group; And can be done.
  • R 2 in the general formula (I) is a benzyl group
  • the benzene ring of the group may be substituted with a halogen atom, a lower alkyl group or a lower alkoxy group.
  • the benzyl group or the substituted benzyl group may be, for example, a benzyl group, a 2-chloro benzene group, a 3-cyclo benzyl group, or a 4-cyclo benzene group.
  • Zinole group 2,4-Dichlorobenzinole group, 4-Bromobenzinole group, 4-Methoxybenzyl group, 2-Methylbenzyl group, 3-Methylenolbe Dimethoxy group, 4-methoxybenzino group, 2-methoxybenzino group, 3-methoxybenzyl group, 4-methoxybenzyl group You.
  • Y in the general formula (I) is a lower alkoxycarbonyl group, it is, for example, a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxy group.
  • Norebonyl group, Isop Mouth can be a hydroxyl group or an n-butoxycarbonyl group.
  • Y in the above general formula (I) is a lower aryl group, it is, for example, an acetyl group, a propionyl group, an n-butanol group, an isobutayl group. It can be a non-reactive group having 2 to 7 carbon atoms such as a non-reactive group.
  • X in the general formula (I) is a cycloalkyloxy group having 3 to 7 carbon atoms, it is, for example, a cyclopropyloxy group, a cyclobutyloxy group, or a cyclobenoxyloxy group. Group, or a hexoxy group.
  • X in the general formula (I) is a lower alkylthio group
  • it is, for example, a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group.
  • X in the general formula (I) is a lower phenolyl phenyl group
  • it is, for example, a methyl phenyl phenyl group, a methyl phenyl phenyl group, a methyl phenyl phenyl group, Group, n-propynoles-no-finolene group, iso-open mouth pinoles-no-lefininole group, n-butynole-sno-lefininole group, s-butylinole-no-finolene group Infinole group, t-butylinolenorfile group, n-pentinolenorrefininole group, isopentinolenorsefininole group, n-hexene
  • a linear chain of 1 to 6 carbon atoms, such as silanol group Alternatively, it can be a branched-chain alkylphenol group.
  • X in the above general formula (I) is a lower alkylsulfonyl group, it is, for example, a methylsulfonyl group, a methylsulfonyl group, or an n-propynolesylonyl group.
  • Nore group, isopropynole, nonylone group, n -butyzorenole group, s-butynole group, n -butyone group, n -pentine group A straight-chain or branched-chain alkyl having 1 to 6 carbon atoms, such as a cinnoles honole group, an isopentyls phenol group, and an n-hexyls phenol group. It can be a ruthnole group.
  • X in the above general formula (I) is a lower alkoxymethyl group, it is, for example, a methoxymethyl group, an ethoxymethyl group, an n-propoxymethyl group.
  • Isopropoxymethyl group, n-butoxymethyl group, s-butoxymethyl group, butoxymethyl group, n-pentyloxymethyl group isopene A straight-chain or branched-chain alkoxymethyl group having 1 to 6 carbon atoms, such as an alkyloxymethyl group and an n-hexyloxymethyl group; be able to.
  • X in the general formula (I) is a lower alkylthiomethyl group
  • it is, for example, a methylthiomethyl group, an ethylthiomethyl group, an n-propylthiomethyl group, or an isopropylthiomethyl group.
  • Group, n-butylthiomethyl group, s-butylthiomethyl group, dibutylthiomethyl group, n-pentylthiomethyl group, isopentinthiomethyl group, n-hexynolethiomethyl group of It may be a linear or branched alkylthiomethyl group having 1 to 6 carbon atoms.
  • X in the above general formula (I) is a lower phenolic phenol group, it may be, for example, a methyl phenyl phenol group, a methyl phenyl phenol group, or a methyl phenol group.
  • X in the above general formula (I) is a lower vinyl sulfonylmethyl group, for example, it is, for example, a methylnorthylhonylmethyl group, a ethylnorthylhonylmethyl group, Methyl group, n-hole Mole group, n-butyl Mole group, n-butyl methyl group, n-butyl methyl group, s- butylate Norre scan Honoré e d Honoré main Chinore group, have Buchinore scan Noreho Ninore methylation group, n - Penchinore scan Noreho two Le main switch Honoré group, Lee Seo Bae Nchinore scan Honoré e d Honoré main Chinore group, n - the key sheet It may be a straight-chain or branched-chain anolequinoles-norefoninolemethylinole group having 1 to 6 carbon atoms, such as a
  • Q is substituted or unsubstituted.
  • R 1 is a lower alkyl group
  • R 2 is a lower alkyl group, a lower alkyl group, a cycloalkyl group having 3 to 7 carbon atoms or a c-lower alkyl group
  • R 3 is mono.
  • Q is a substituted phenyl group
  • Ri and R 2 are lower alkyl groups, and are mono-, di- or A tri-halo-substituted phenyl group
  • X is a nitrogen atom or a lower alkynol group
  • the isoxozolinone derivative of the general formula (I) according to the first present invention is characterized in that the substituent Q at the 4-position of the isoxozolin ring is substituted or unsubstituted.
  • An aryl group, a substituted or unsubstituted alkyl group, a heterocyclic group, a heterocyclic-methyl group, a lower alkoxycarbonyl group, or an N-mono-substituted, N, N-di- U.S. Pat. No. 4,440,018 discloses a known isooxozolin-3 compound represented by the general formula (Q), which is specified as a substituted or unsubstituted rubamoinole group.
  • the isoxozolinon derivative of the general formula (I) according to the first present invention has the following general formula (la)
  • the isoxazozolinone derivative of the first general formula (I) has the following general formula (lb)
  • RR 2 and R 3 are each defined in the above general formula (I). Has the same meaning as defined, and Q b is
  • R 4 , W and k have the same meanings as defined in the general formula (I)), and are a substituted or unsubstituted aralkyl group. Composed of isoxoxazolinone derivatives.
  • the isoxoxazolinone derivative of the general formula (I) according to the first invention has the following general formula (Ic)
  • the isoxoxazolinone derivative of the general formula (I) according to the first present invention has the following general formula (Id)
  • R 2 and R 3 each have the same meaning as defined in the above general formula (I), and Q d is 0
  • R 6 is a lower alkoxycarbonyl group of a lower alkoxy group as defined in the general formula (I)). It consists of a derivative.
  • R 7 and R 8 each have the same meaning as defined in the general formula (I)), and are substituted or unsubstituted rubamoyl groups. It is composed of a sosoxazolinone derivative.
  • R 1 is a lower alkanol group
  • R 2 is a lower alkyl group.
  • R 3 is mono-, di- or tri-no, a mouth-substituted phenyl group, a lower-alkyl-substituted phenol group, or a lower-alkoxy-substituted group.
  • Ethanol group cyano-substituted phenol group, c-lower phenol-substituted phenyl group, 2-pyridyl group or halo-substituted 2-pyridyl group
  • Qa is a phenyl group, or Qa is a nitrogen atom, a lower alkyl group, a lower alkoxy group, a c-lower alkoxy group. 1 or 2 substituents selected from the group consisting of a lower alkylthio group, a lower alkyl group, a lower alkyl group, and a lower alkyl group or a lower alkyl group. It is preferably a phenyl group substituted by.
  • R 1 and R 2 are lower alkyl groups, and R 3 is mono- or di-. Is a tri-substituted phenyl group, and Qa is a phenyl group mono- or di-substituted with a no, a halogen atom or a lower alkyl group. Is good.
  • the isoxoxazolinone derivative of the general formula (Ia) according to the first embodiment of the first present invention is, as one special mode thereof, a compound represented by the following general formula: Formula (Ia-1)
  • R is a hydrogen atom or a lower alkyl group, is a lower alkyl group
  • R 3a is mono-, di- or tri- A nitrogen-substituted phenyl group
  • Qa 2 is a mono-substituted or di-substituted nitrogen atom and / or a lower alkyl group. Or a tri-substituted substituted furyl group).
  • R 2a is an isopropyl group and R la is a hydrogen atom, a methyl group or an ethyl group.
  • der is, and mosquito ⁇ also R 1 a 2 - off Noreo port full et two Honoré group, 3 - off Honoré O b off e d Honoré group, 4 - off Honoré O b off e d Honoré group, 2, 4 -Diphenyl olefininole, 2,5 -Difluoro feninole, 3,5 -Diphenyl feninole, 2,3,4-Trifluorene mouth Phenyl group, 2,4,5-triphenyl phenol group, 2-chloro phenol group, 3-chloro phenol group, 4-chloro group Mouth phenyl group, 2,4-dichlorophenyl group, 3,4-dichlorophenol group, 3,5-dike
  • the isoxozolinone derivative of the general formula (la-1) is, as one particularly preferred embodiment thereof, the following: General formula (Ia-2)
  • R 2 is a hydrogen atom, a methyl group or an ethyl group
  • i-Pr is an isobromo group
  • R 3a2 is 2- fluorophenyl .
  • Mouth Mouth-4-Phenyl Mouth phenyl or 4-methylphenyl X is a phenolic phenol group, and X is a nitrogen atom or a lower phenol group, and n is 1.) Consists of a zolinone derivative.
  • Representative examples of the compound of the above general formula (la-1) include the following compounds:-
  • the isoxazolinone derivative of the above general formula (lb) according to the second embodiment of the first present invention has one of the following general formulas (Ib -1) [In the formula, Qb is as defined in the above general formula (I).
  • R 4 , W and k have the same meanings as defined in the general formula (I)), and are a substituted or unsubstituted aranoloxy group.
  • R lb is Ri hydrogen atom or a lower alkyl group der
  • R 2 b is lower ⁇ Norekiru group, a lower a Le Quai two group, a lower a Le key two Le group or having a carbon number of 3-6 consequent b
  • R 3 b is a lower anoalkyl group or the following m
  • Y is a halogen atom, a lower alkyl group, a haguchi-lower phenol group, a lower phenol group as defined in the general formula (I).
  • I is a substituted or unsubstituted phenyl group, wherein m is 0 or an integer of 1 to 5). It consists of sosoxazolinone derivatives.
  • R 4 is a hydrogen atom or a lower alkyl group
  • W is a nitrogen atom or a lower phenol group
  • k is 0 or an integer of 1-2.
  • a substituted or unsubstituted aralkyl group represented by
  • Representative examples of the compounds of the above general formula (ib-1) include the following compounds:-
  • the isoxozazolinone derivative of the general formula (Ic) according to the third embodiment of the first invention is characterized in that it has one special embodiment and And the following general formula (Ic-1)
  • Qe is a methyl group substituted by a heterocyclic group or a heterocyclic ring as defined in the above general formula (IC), and Ric is a hydrogen atom or a lower alkyl group.
  • R 2c is a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a cycloalkyl group having 1 to 6 carbon atoms, and further a lower phenol group. The group is
  • Yc may be the same as or different from each other, and may be a halogen atom, a lower alkyl group, a halo-lower alkyl group, a lower phenolic alkoxy group, or a lower alkyl group.
  • M- is a substituted or unsubstituted phenyl group, wherein m is or an integer of 1 to 5). Consists of derivatives.
  • the compounds of the general formula (Ic-1) is, as its preferred correct state like, the general formula (Ic-1) Ole Te,, Ric and R 2 c are both a lower alkyl Honoré group RSc is a mono- or di-halogen-substituted phenyl group, and Qc is represented by the following formula:
  • R 5 represents a lower alkynole group or a phenyl group
  • a represents 0 or an integer of 1 to 2
  • E is the same.
  • isoxazolinonone derivative represented by the above general formula (Ic-1) is represented by the following general formula (Ic-2) as another preferred embodiment.
  • R lc2 represents a hydrogen atom, a methyl group or an ethyl group
  • i-Pr represents an isopropyl group, and furthermore, a chlorine atom and / or a fluorine atom.
  • R 5 represents a lower alkylene group or a phenyl group
  • a represents 0 or an integer of 1-2
  • E represents the same. May be different or different, such as hydrogen atom, halogen atom,
  • It can be composed of a linone derivative.
  • Representative examples of the compounds of the above general formula (Ic-2) include the following compounds:
  • R 6 is Ri low grade Al co key sheet groups der of Ri Contact and defined the general formula (Id), R 1 d is Ri hydrogen atom or a lower Anorekiru group der, R 2 d is lower alkyl group, lower alkyl group, low Is a lower alkyl group or a cycloalkyl group having 36 carbon atoms, and R 3d is a lower alkyl group or a compound represented by the following formula:
  • Yc may be the same or different, and a halogen atom, a lower alkyl group, a halo-lower alkyl group, a lower alkyloxy group or- Lower alkoxy group, m is 0 or 1
  • a substituted or unsubstituted phenyl group (which is an integer of 5).
  • Rid and R2d are both lower phenols, and R3d is mono- or di-. And a halogen-substituted phenyl group, and R 6 is preferably a lower alkoxy group.
  • isoxozazolinon derivative of the above-mentioned general formula (Id-1) has the following general formula (Id-2) as a preferred embodiment thereof.
  • Rid 2 represents a hydrogen atom, a methyl group or an ethyl group
  • i-Pr represents an isopropyl group
  • R 3 d 2 represents a chlorine atom and (and Is a mono- or di-substituted phenyl group with a fluorine atom
  • R 6 is a lower alkoxy group. It can be composed of a soxazolinone derivative.
  • R 7 is a hydrogen atom or a lower alkyl group
  • R 8 is water
  • a substituted or unsubstituted alkyl group which is a hydrogen atom, a lower alkyl group or a phenyl group
  • R le is a hydrogen atom or a lower phenol group
  • R 2e represents a lower alkyl group
  • R 3e represents a mono- or di-halogen-substituted phenyl group.
  • the compound of the above general formula (Ie-1) is preferably represented by the following general formula (Ie-2)
  • R 7e and R 8e are both lower alkyl groups
  • R 2 is a hydrogen atom, a methyl group or an ethyl group
  • i-Pr is an isopropyl group
  • R 2 is a mono- or di-substituted phenyl group which is mono- or di-substituted by chlorine atom and / or fluorine atom. It can be.
  • Representative examples of the compounds of the above general formula (le-1) include the following compounds:-
  • Table 1 exemplary compound examples of the isoxazolinone derivative of the general formula (la) according to the first embodiment of the first invention are shown in Table 1 below, and their compound Nos. Shown together with No. 1 to No. 490.
  • the compound No. shown in Table 1 is also referred to in Examples and Test Examples described later.
  • Me is an abbreviation for methyl
  • Et is an abbreviation for ethyl
  • i-Pr is an abbreviation for isopropyl
  • n-Pr is an n-propyl.
  • Exemplary compound examples of the isoxazolinone derivative of the general formula (Ic) according to the third embodiment of the first invention are shown in Table 3 below, and the compound Nos. 581 to 730 are shown. And are shown together.
  • the compound No. shown in Table 3 is also referred to in the examples and test examples described later.
  • Qc represents a heterocyclic group or a methyl group substituted by a heterocyclic ring.
  • Exemplary compound examples of the isoxazolinonone derivative of the general formula (Id) according to the fourth embodiment of the first invention are shown in Table 4 below and the compound No. 731 is shown. These compound Nos. Shown together with 760 to 760 are also referred to in the examples and test examples described later.
  • Qd represents a lower alkoxycarbonyl group of the formula Re—CO—.
  • RG represents a lower alkoxy group.
  • N-C0- represents a substituted or unsubstituted rubamoyl group.
  • R 7 is a hydrogen atom or a lower Al kill group
  • r R 8 is mean a hydrogen atom, a lower alkyl group or a Tilia two Le group
  • the isoxoxazolinone derivative represented by the above general formula (I) is contained as an active ingredient, Provided is a herbicidal composition characterized by containing an acceptable carrier.
  • a second herbicidal composition according to the present invention is a herbicidal composition comprising, as an active ingredient, the isoxoxazolinone derivative represented by the above general formula (Ia), Or a herbicide composition containing the isoxoxazolinone derivative represented by the general formula (lb) as an active ingredient, or represented by the general formula (Ic)
  • a herbicidal composition containing an isoxoxazolinone derivative as an active ingredient; or an isoxazozolinone derivative represented by the above general formula (Id) as an active ingredient In the form of a herbicide composition containing, as an active ingredient, or an isoxoxazolinone derivative represented by the above general formula (Ie). You can do it.
  • the first isoxoxazolinone derivative of the general formula (I) according to the present invention and more specifically, the general formulas (la), (lb), (Ic), As shown in the test examples below, the isoxozazolinonone derivative (Id) or (Ie) has excellent herbicidal activity and controls unwanted weeds. It can be used as a herbicide for soup.
  • broadleaf weeds that can be controlled include Schibi (Abuton genus), vagate ( ⁇ 4ma_ra 2t 2us genus), and Inubu iA us ⁇ ), ragweed), kosen dang ⁇ (Bidens) ⁇ ⁇ Chenopodi um phoenix, ⁇ ⁇ D D D D (Datura phoenix), Yaem dara ( Gahum ⁇ ), Manole baa sagao (genus omoea), Hirugao (genus pomoea, genus azena indernia), force beetle (Matricaria phoenix), inutade (Persicaris,), suberihi (Portulaca), Kika Shigusa (RotaJa), American Golden Godzica (S) 'da), Vietnamese Domstad (Sinapis style), Nokobe (Stellaria), Mire (Genus), fir tree (a
  • Grapeaceous crops that receive substantially no or no phytotoxicity even when treated with the compounds of the present invention include wheat (Ordeum spp.), Rice (Orj ⁇ a spp.), And sats There are mushrooms (genus Sacc / iaruin), wheat (Triticum lice), and corn (genus Zea).
  • Broadleaf crops that are substantially or completely free of phytotoxicity even when treated with the compounds of the present invention include peanuts (Arac's), Tensai Beta) and abrana. Brassica sp.), Dies (JycieJh), ) And tomato (genus Lycopersicon).
  • the herbicidal composition according to the second aspect of the present invention comprises the isoxoxazolinone derivative of the general formula (I) according to the first aspect of the present invention as an active ingredient, and a carrier. It is formulated in the form of a composition.
  • the herbicidal composition is formulated in this way, the compound of the general formula (I) as an active ingredient is added to a carrier or a diluent, if desired, and if appropriate, to a carrier or a diluent.
  • fungicides, insecticides, herbicides, dust killers, safeners (safeners), plant growth regulators, fertilizers, soil conditioners, etc. can be further added.
  • herbicides for example, fungicides, insecticides, herbicides, dust killers, safeners (safeners), plant growth regulators, fertilizers, soil conditioners, etc.
  • safeners safeners
  • plant growth regulators fertilizers, soil conditioners, etc.
  • any carrier that is commonly used for agricultural chemicals can be blended with either a solid or liquid carrier.
  • solid supports that can be included in the composition include mineral powders (kaolin, bentonite, cres, monmorillonite, tanolek, diatomaceous earth, Mica, vermiculite, quartz, canecarbonate, limestone, white lime — bon, slaked lime, silica sand, ammonium sulfate, urea, etc., vegetable powder (soybean powder) , Wheat flour, wood flour, tobacco flour, starch, crystalline phenolic cellulose, etc.), polymer compounds (petroleum resin, vinyl chloride, ketone resin, etc.), aluminum , Silicates, glycopolymers, highly dispersible silicates, and waxes.
  • liquid carrier examples include water, phenolic compounds (methyl alcohol, phenolic alcohol, phenolic alcohol, n-propyl). ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ Nole, ethyl alcohol, benzyl alcohol, etc., aromatic hydrocarbons (toluene, benzene, xylene, ethylenbenzene) , Methinolenephthalene, etc.), norogenated hydrocarbons (chlorophore, carbon tetrachloride, chloronomethane, chloronoethylene, monoc) Lorenobenzen, Tricyclone noretromethane, Zykronorhe noreorometan, etc.), Ethenoles (Echile-one tenore, Echile) Oxide, gioxan, tetrahydrofuran, etc., ketones (aceton, methinole etinoleketone,
  • the herbicidal composition according to the present invention When the herbicidal composition according to the present invention is formulated into an emulsion, a wettable powder, a flowable, or the like, the composition may be emulsified, dispersed, solubilized, moistened, foamed, lubricated, and spread.
  • a surfactant is added. Examples of such surfactants include non-ionic surfactants (polyoxyethylene alkylene-tenol, polyoxyethylene phenol).
  • amphoteric surfactants e.g., carboxylic acid (betaine type), ester sulfate, etc.
  • carboxylic acid betaine type
  • ester sulfate etc.
  • polyvinyl alcohol PVA
  • canoleboxinolexenolose CMC
  • arabia gum It is possible to mix various adjuvants such as polyvinyl acetate, sodium anoregate, gelatin, and tragacanth.
  • the isooxozolinone derivative represented by the general formula (I) is added to the total weight of the composition. 0 There Nitsu 00 1% to 95%. (weight 0/0; the same below), the preferred and rather 0 0 1% to 7 present compositions Let 's you containing 5% range. It can be formulated.
  • the isoxozolinone derivative can be contained at a ratio in the range of 0.01% to 5%.
  • the herbicidal composition of the present invention thus prepared can be used, for example, in the case of granules and florables as it is on the soil surface, in soil or in water.
  • the compound of the general formula (I) can be applied in a range of about 0.3 g to 300 g per 10 ares as a converted amount of the active ingredient.
  • the compound of the formula (I) is converted into an effective ingredient in an amount of about 0.3 g to 300 g per 10 a. Spray in the range of.
  • isoxozolinonone derivatives of the general formula (I) according to the first present invention are 3 to 10 per 10 anoles of paddy field. Even when applied at a low application rate in the g range, the main weeds of paddy field weeds, such as Tainubie and other weeds, are completely killed with almost 100% herbicidal rate. It was recognized that the herbicidal effect was excellent because of the ability to do this. Many of the compounds of the general formula (I) show excellent selective herbicidal activity between various weeds and upland crops at the upland crop cultivation site, In other words, it was found that it did not cause phytotoxicity to the field crops, but exhibited excellent herbicidal effects on the main weeds in the fields.
  • compounds No. 4 and No. 348 in Table 1 above were used in cultivated areas such as wheat and barley.
  • 1.6 g to 100 g per 10 ares, and preferably 1.6 g to 25 g per gal (Galium spp.) .
  • weeds in a paddy field or a field of paddy field are preferably in a range of 0.3 g to 300 g per 10 ares of the paddy field or the field.
  • the compound of general formula (I) or a herbicidal composition containing the compound is required to control weeds that have grown in rice paddy fields.
  • the material can be sprayed on the paddy water surface or mixed with the paddy soil.
  • weeds can be controlled by mixing the compound of the present invention or its composition in field soil, or bringing the compound of the present invention into contact with weed stems and leaves.
  • the compound of the present invention can be applied in an amount that does not cause phytotoxicity to the growing crop and that is effective for controlling weeds.
  • the compound of the general formula (I) according to the first aspect of the present invention is a compound represented by the following general formula (II), which is represented by the following general formula (II): (Ii) reacting a chlorocalponilating agent with an isoxazozolin represented by the general formula (III) described below to give a compound represented by the following general formula (III):
  • the first step is produced by reacting an amine derivative represented by the following general formula (IV) with the compound of the general formula (III).
  • the compound can be produced by a method comprising the second step of producing the compound of the general formula (I).
  • hydroxyisoxazoles represented by are represented by the following general formula ( ⁇ ′)
  • the hydroxyisoxazoles of the general formula (II) or isoxoxazolino of the general formula (II), which is a tautomer thereof For phenols, phosgene, triphosphogen (ie, bis (trichloromethyltinole) carbonate) or chlorinated phenols as lipophoric agents
  • phosgene, triphosphogen ie, bis (trichloromethyltinole) carbonate
  • chlorinated phenols as lipophoric agents
  • the reaction of trichloroacetic acid with phenolic forenoic acid is carried out to give a compound of the general formula (III) Produces carbamoyluk mouth lights represented by.
  • the production of the carbamoyl alkoxides of the general formula (III) in the above first step is carried out in an organic solvent in the presence of the hydrocyanic oxazoles of the general formula (II).
  • phosgene, triphosphogene ie, visogen
  • Solvents used in this reaction include, for example, aromatic hydrocarbons such as benzene, tonolene, and xylene, dichloromethane, and chloroform.
  • Harogens such as honolem, carbon tetrachloride, dichloronorethane, trickle lutean, and tetrachloretane Esters such as hydrogenated hydrocarbons, ethyl acetate and ethyl propionate, and nitriles such as acetonitril and propionitol Etc. can be used, preferably using toluene.
  • the reaction temperature is usually from room temperature to 150 ° C, preferably from 70 to 100 ° C.
  • the reaction time varies depending on the reaction temperature and the reaction substrate, but the reaction is usually completed in 30 minutes to 10 hours.
  • the compound of formula (III) can be collected by removing the solvent from the reaction solution. This can be used as is in the next second step without purification.
  • the reaction for forming the target compound of the general formula (I) is carried out in an organic solvent by using a compound represented by the general formula (III) and a compound represented by the general formula (IV) This is achieved by mixing and reacting the amide derivative with a dehydrochlorinating agent.
  • the dehydrochlorinating agents used in this reaction include triethylamine, tributinoleamine, getylisopropylamine, 4-dimethylaminopropylamine.
  • Solvents used in the reaction of the second step include, for example, aromatic hydrocarbons such as benzene, toluene, and xylene, dichloromethane, and chloromethane.
  • Halogenated hydrocarbons such as lohonolem, carbon tetrachloride, dichloronoletan, trichloronoletan, tetrachloronetan, and acetonitrile.
  • Trinoles, propionyl trinitoles such as trinole, ethyl acetate, esters such as ethyl propionate, jechinore ethenole, tetra Ethers such as hydrofuran can be used, or a mixed solvent of these can be used.
  • the reaction temperature is usually from room temperature to 150 ° C, preferably from 20 to 30 ° C.
  • the reaction time varies depending on the reaction temperature and the reaction substrate, but the reaction is usually completed in 30 minutes to 10 hours.
  • the desired compound of the general formula (I) is collected by usual post-treatment.
  • the target compound can be obtained by adding water to the reaction solution, washing with water, and distilling off the solvent.
  • the obtained target compound can be purified, if necessary, by an operation such as column chromatography, recrystallization, or the like. Examples of the production of the compound of the general formula (I) by a method comprising the above two steps are shown in Examples 1 to 24 described below.
  • the compound represented by the general formula (II) or (II ′), which is a starting material used in the above method, is obtained by reacting the following formula (V) with a / 3-keto ester compound.
  • the above step A is carried out by reacting the hydroxylamine of the formula (VI) with the / 3-ketoesters of the general formula (V). It produces the hydroxyamic acid represented by (VI I).
  • This step is preferably performed in a solvent in the presence of a base.
  • Solvents used herein include methanol, ethanol, isopropyl alcohol such as isopropanol, and ethyl alcohol.
  • ethers such as tetrahydrofuran and dioxane, or a mixed solvent of these organic solvents and water, preferably with alcohol. It is a mixed solvent with water.
  • Bases used in the above reaction include sodium hydroxide, potassium hydroxide, and other metal hydroxides, sodium carbonate, and carbonate.
  • Alkali metal carbonates such as lithium, sodium methoxide, and alkaline metal oxides, such as sodium methoxide Power to produce; power to produce; preferably Alkali metal hydroxide
  • the above base is used in an amount of about 1 equivalent, and that the hydroxyamine is usually 1 to 10 equivalents, preferably 2 to 1 equivalent. Use 5 equivalents.
  • Hydroxamine used as a reactant is usually used in the form of hydrochloride, sulfate or hydrate.
  • the reaction temperature is usually ⁇ 78 to 10 ° C., preferably ⁇ 30 ° C. to 0 ° C.
  • the time required for the reaction varies depending on the reaction temperature, the solvent and the like, but is usually 10 minutes to 5 hours.
  • an acid is added to the reaction solution obtained in the step A at a time without isolating the intermediate hydroxamic acid (VII). This is done by heating quickly.
  • the acid used here include inorganic acids such as hydrochloric acid, sulfuric acid, and nitric acid, and acids such as sulfuric acid, benzensulphonic acid, and paraenthenolefonic acid.
  • the organic acid can be removed, but is preferably hydrochloric acid.
  • the above-mentioned acids are used in an amount of 1 equivalent or more, preferably in an amount of 5 to 15 equivalents. Reaction temperature is 40-200.
  • the power is C; it is preferably 50 to 150 ° C, and the time required for the reaction is usually 30 minutes to 3 hours, although it depends on the reaction substrate, the reaction temperature and the like.
  • the compound of the general formula (II) or (II) is collected from the reaction solution obtained in the step B according to a conventional method.
  • the compound (II) or (II) is precipitated from the reaction solution by cooling the reaction solution, and the compound is recovered by filtration. In the case where no precipitation occurs, it can be recovered by extracting from the reaction solution with a solvent and concentrating by distilling off the solvent.
  • Production examples of the compound of the formula (ii) or ( ⁇ ') are shown in Reference Production Examples 1 to 9 below.
  • reaction solution was washed successively with 1N-hydrochloric acid, a 5% aqueous solution of sodium hydrogen carbonate and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off.
  • Yield 68% Melting point 176-: L78 ° C was indicated.
  • reaction solution was washed successively with 1N-hydrochloric acid, a 5% aqueous sodium hydrogen carbonate solution and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off.
  • the product was purified by silica gel chromatography to obtain 2.7 g (yield: 66%) of the target compound of the title. It showed a melting point of 112-114 ° C.
  • reaction solution was washed successively with 1N-hydrochloric acid, 5% aqueous sodium hydrogen carbonate solution and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off.
  • the product was purified by silica gel column chromatography to obtain 2.8 g (yield: 72%) of the title compound. Melting point 129-: showed 13 l'C.
  • reaction solution was washed successively with 1N-hydrochloric acid, 5% aqueous sodium hydrogen carbonate solution and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off.
  • the product was purified by silica gel column chromatography to obtain the title compound (3.0 g, yield 70%). The melting point was 131-133 ° C.
  • reaction solution was sequentially washed with 1N-hydrochloric acid, a 5% aqueous sodium hydrogen carbonate solution and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off.
  • Object to silica gel force Purification by column chromatography gave 2.5 g (74% yield) of the title compound. It showed a melting point of 124-125 ° C.
  • reaction solution was washed successively with 1N-hydrochloric acid, 5% aqueous sodium hydrogen carbonate solution and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off.
  • the product was purified by silica gel column chromatography to obtain 2.9 g (yield: 68%) of the target compound of the title. Melting point 110 or more: ll ° C was shown.
  • reaction solution was washed successively with 1N-hydrochloric acid, a 5% aqueous sodium hydrogen carbonate solution and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off. Purification by silica gel column chromatography gave 2.4 g (71% yield) of the title compound. Melting point 113-: 114 ° C.
  • reaction solution was washed successively with 1N-hydrochloric acid, 5% aqueous sodium hydrogen carbonate solution and saturated saline, and dried over anhydrous sodium sulfate.
  • residue obtained was purified by silica gel chromatography and chromatographed on a silica gel column, yielding 4.5 g of the title compound (80% yield). I got 84-86 ° C.
  • reaction solution was washed with a saturated saline solution, dried over anhydrous sodium sulfate, and after distilling off the solvent, the obtained residue was subjected to silica gel chromatography chromatography. Purification gave 2.9 g (69% yield) of the title compound. Melting point 98-: 100 ° C.
  • reaction solution was washed successively with 1N-hydrochloric acid, a 5% aqueous sodium hydrogen carbonate solution and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off.
  • reaction solution was washed successively with 1N-hydrochloric acid, 5% aqueous sodium hydrogen carbonate solution and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off.
  • Tri-phosphogen that is, bis (tris) 1.5 g of a 25 ml solution of tonorenene was added, and the mixture was stirred at 90 ° C. for 1 hour. After distilling off the solvent and excess phosgene from the obtained reaction mixture under reduced pressure, the obtained residue was mixed with 25 ml of toluene and 25 ml of tetrahydrofuran.
  • reaction solution is washed with a saturated saline solution, dried over anhydrous sodium sulfate, and after distilling off the solvent, the obtained residue is purified by silica gel chromatography. Purification at a time gave 3.7 g (76% yield) of the title compound. 97-99 ° C.
  • reaction solution was sequentially washed with 1N-hydrochloric acid, a 5% aqueous sodium hydrogen carbonate solution and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off.
  • reaction solution was washed successively with 1N-hydrochloric acid, 5% aqueous sodium hydrogen carbonate solution and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off.
  • 1N-hydrochloric acid 5% aqueous sodium hydrogen carbonate solution and saturated saline
  • the solvent was distilled off.
  • silica gel chromatography the target compound of the title was purified.
  • reaction solution was washed successively with 1N-hydrochloric acid, 5% aqueous sodium hydrogencarbonate solution and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off.
  • the product was purified by silica gel chromatography and chromatograph to give 2.7 g (65% yield) of the title compound. 112-114 ° C.
  • reaction solution was washed successively with 1N-hydrochloric acid, 5% aqueous sodium hydrogen carbonate solution and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off.
  • the product was purified by silica gel chromatography and the target compound of the title was obtained.
  • reaction solution was washed successively with 1N-hydrochloric acid, a 5% aqueous solution of sodium hydrogen carbonate and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by silica gel chromatography to give 3.0 g (76% yield) of the title compound. Mp 67-69't.
  • reaction mixture was further stirred at -30 ° C for 2 hours, 7 ml of acetone was added at this temperature, and the mixture was stirred for 15 minutes.
  • the resulting reaction solution was returned to room temperature, acidified with 40 ml of concentrated hydrochloric acid, and heated at 80 ° C for 1 hour.
  • reaction mixture was further stirred at -30 ° C for 2 hours, 60 ml of acetate was added at this temperature, and the mixture was stirred for 15 minutes.
  • the reaction mixture was brought to room temperature, acidified with concentrated hydrochloric acid (40 ml) and heated at 80 ° C for 1 hour.
  • the obtained reaction solution was poured into water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and then distilled off with a solvent.
  • the obtained residue was purified by silica gel chromatography to obtain 9.5 g (yield: 45%) of the title compound as an oily substance.
  • the —ketoesters of the general formula (V) used as starting compounds in the above Reference Production Examples 1 to 8 can be obtained by a known method [organic synthesis] ⁇ Collective 'Volume 11, p. 487, and Organic Synthesis-Collective (See Volume II, p. 284) according to the following reaction formula from the cyanomethyl derivative of formula (VIII) having a substituent Q to formula (IX) It is easily synthesized via the compound of formula (1).
  • the wettable powder containing the compound of the present invention prepared according to Example 26 was diluted with water to prepare drug solutions containing the compound at various predetermined concentrations. A predetermined amount of these chemicals was dropped on the water surface. The amount of the applied drug was adjusted to the amount shown in the following table.
  • the dry weight of the surviving rice millet was measured to determine the herbicidal effect on the rice millet, and the herbicidal effect was calculated by the following formula and expressed in%.
  • a represents the dry weight (g) of the surviving weed in the treated plot
  • b represents the dry weight (g) of the weed in the untreated plot
  • Comparative drugs (1) to (17) are isoxazolinones described in the literature shown in Table 7 below. 7
  • This example shows a test for herbicidal effect on Thai millet (by weeding treatment during the growing season).
  • Subsequent management was carried out in a glass greenhouse, and when the seeds reached the 1.5-leaf stage, weeding was performed. That is, the wettable powder containing the compound of the present invention prepared according to Example 26 was diluted with water to prepare drug solutions containing the compound at various predetermined rates. A predetermined amount of the chemical solution was dropped on the water surface. The amount of chemical solution added was equivalent to the amount of applied drug shown in the following table.
  • 30 seeds of azena, oak, and squirrel were sown at a depth of 1 to 2 cm in the soil surface layer, respectively.
  • the water depth was kept at 2 cm.
  • Subsequent management was performed in a glass greenhouse, and weeding was performed one day after sowing. That is, the wettable powder prepared according to Example 26 was diluted with water to prepare chemical solutions having various concentrations, and a predetermined amount of the chemical solution was dropped.
  • Field soil (alluvial loam) was filled in a pot made of 1/5000 ares.
  • the surface lcm of soil in the pot and 50 weed seeds of each of the following plants are uniformly mixed with each other: After that, the surface layer was lightly pressed. Two days after sowing, weeding was performed. That is, a chemical solution prepared by diluting the emulsion prepared according to Example 27 with water was sprayed onto the soil surface at a rate of 100 liters per 10 ares. When the application amount of the active ingredient was converted, it was equivalent to 120 g per 10 ares.
  • Field soil (alluvial loam) was placed in unglazed pots, 1 / 10,000 a yard. Put the seeds of each crop (5 soybeans, 5 corns, 10 sugar beet, 10 rapeseed, 10 wheat and 10 oats) in separate pots Seeding was performed and the surface layer was lightly pressed. One day after sowing, weeding treatment was performed. That is, a chemical solution prepared by diluting the emulsion prepared according to Example 27 with water was sprayed onto the soil surface at a ratio of 100 liters per 10 aar. Converted amount of active ingredient applied is 10 A This was equivalent to 120 g.

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  • Plural Heterocyclic Compounds (AREA)

Abstract

Nouveaux dérivés d'isoxazolinone représentés par la formule générale suivante (I) qu'on peut utiliser en tant qu'herbicides pour les rizières et les hautes terres, qui exercent une activité herbicide élevée et présentent une sélectivité importante de l'activité herbicide, ainsi qu'une rémanence excellente de cette activité, dans laquelle R1 représente alkyle inférieur ou hydrogène; R2 représente alkyle inférieur ou un analogue; R3 représente phényle mono-, di- ou tri-halogéné, un autre phényle substitué, 2-pyridyle, 2-pyridyle halogéné ou analogues; Q représente phényle substitué ou insubstitué, benzyle, un groupe hétérocyclique, un groupe méthyle substitué par un hétérocycle, alkoxycarbonyle ou carbamoyle N,N-disubstitué. La plupart de ces nouveaux dérivés peuvent détruire Echinochloa oryzicola et d'autres plantes nuisibles principales, en totalité ou presque complètement, même avec une faible dose, ne détériorent pas le riz brut, l'orge ou les plantes céréalières et présentent une activité herbicide résiduelle pendant une durée prolongée contre les plantes nuisibles poussant dans les rizières et dans les hautes terres.
PCT/JP1997/003210 1996-09-13 1997-09-11 Derives d'isoxazolinone et compositions herbicides WO1998011079A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU42196/97A AU4219697A (en) 1996-09-13 1997-09-11 Isoxazolinone derivatives and herbicide compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP8/243776 1996-09-13
JP24377696 1996-09-13

Publications (1)

Publication Number Publication Date
WO1998011079A1 true WO1998011079A1 (fr) 1998-03-19

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PCT/JP1997/003210 WO1998011079A1 (fr) 1996-09-13 1997-09-11 Derives d'isoxazolinone et compositions herbicides

Country Status (2)

Country Link
AU (1) AU4219697A (fr)
WO (1) WO1998011079A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1359150A3 (fr) * 1998-02-11 2003-11-19 Basf Aktiengesellschaft Procédé et intermediaires pour la préparation de 7-alkyltriazolopyrimidines fongicides

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4044018A (en) * 1974-08-19 1977-08-23 Sankyo Company Limited Isoxazolone derivatives, their preparation and their use as plant growth regulators
JPH0539275A (ja) * 1990-08-10 1993-02-19 Sankyo Co Ltd 除草性及び殺虫性イソオキサゾリノン化合物

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4044018A (en) * 1974-08-19 1977-08-23 Sankyo Company Limited Isoxazolone derivatives, their preparation and their use as plant growth regulators
JPH0539275A (ja) * 1990-08-10 1993-02-19 Sankyo Co Ltd 除草性及び殺虫性イソオキサゾリノン化合物

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1359150A3 (fr) * 1998-02-11 2003-11-19 Basf Aktiengesellschaft Procédé et intermediaires pour la préparation de 7-alkyltriazolopyrimidines fongicides

Also Published As

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AU4219697A (en) 1998-04-02

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