WO1997041116A1 - Derives du benzene substitues par des heterocycles, et herbicides - Google Patents

Derives du benzene substitues par des heterocycles, et herbicides Download PDF

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Publication number
WO1997041116A1
WO1997041116A1 PCT/JP1997/000340 JP9700340W WO9741116A1 WO 1997041116 A1 WO1997041116 A1 WO 1997041116A1 JP 9700340 W JP9700340 W JP 9700340W WO 9741116 A1 WO9741116 A1 WO 9741116A1
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WIPO (PCT)
Prior art keywords
group
compound
solvent
methyl
reaction
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Application number
PCT/JP1997/000340
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English (en)
Japanese (ja)
Inventor
Hiroyuki Adachi
Katsunori Tanaka
Masao Yamaguchi
Osamu Miyahara
Masami Koguchi
Takashi Kawana
Akihiro Takahashi
Shigeo Yamada
Original Assignee
Nippon Soda Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Application filed by Nippon Soda Co., Ltd. filed Critical Nippon Soda Co., Ltd.
Priority to AU16707/97A priority Critical patent/AU1670797A/en
Publication of WO1997041116A1 publication Critical patent/WO1997041116A1/fr

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Classifications

    • 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
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • A01N43/80—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 1,2
    • 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
    • C07D261/08—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Definitions

  • Japanese Patent Application Laid-Open No. 2-73 discloses a general formula [II]
  • WO 96/26206 discloses a pyrazole compound in which the 3-position of the benzoyl moiety is substituted with a heterocyclic ring according to the formula [VI] [VI]
  • An object of the present invention is to provide a herbicide which can be synthesized industrially advantageously, has a lower dose, is effective, has high safety, and has high crop selectivity.
  • the present invention is a herbicide comprising as an active ingredient a 4-benzoylpyrapool compound represented by the general formula [I] wherein the 3-position of the benzoyl moiety is substituted with a heterocyclic ring.
  • the present invention provides a compound represented by the general formula [I]:
  • R 1 represents a d-n alkoxy group or a C,-"haloalkoxy group.
  • R 3 represents a hydrogen atom or a d- fi alkyl group.
  • R G is a hydrogen atom, C, - 6 alkyl or -.. Which "represents a haloalkyl group] or a salt thereof, and a herbicide containing the same compound
  • the present invention in detail explained I do.
  • the present invention has the general formula (I)
  • R 1 is, main butoxy, E Bok alkoxy, Purobokishi, isoproterenol epoxy, butoxy, t-Butokin C Bok e alkoxy group such as a group, or Torifuruoro Roh butoxy, trichloroacetic main Bok alkoxy, Torifuruo Represents a C 6 -alkoxy group such as a roethoxy group.
  • R 2 is fluorine, chlorine, halogen atom such as bromine, triflate Ruo Russia methyl, C etc. triflate Ruoroechiru, - 6 haloalkyl group, methylthio, Echiruchio, Puropiruchi O, C preparative G alkylthio group such as isopropylthio, methylsulphinyl, Echiru sulfinyl, propyl sulfinyl represents C, Ryo Ruki Rusuru sulfinyl group or a methylsulfonyl, Echirusuruhoniru, propylsulfanyl Honiru, C 6 alkyl sulfonyl Le group such isopropylsulfonyl or isopropyl sulfinyl.
  • R '1 is a hydrogen atom or a methyl, Echiru, propyl, isopropyl, heptyl, I Sobu
  • R 4 and R 5 are each independently a hydrogen atom, C, such as methyl, ethyl, propyl, etc.
  • R " is C, such as a hydrogen atom, methyl, Echiru, propyl - I; represents an alkyl group or a triflate Ruoromechiru, triflumizole Ruo Roe C beta haloalkyl group chill like.
  • the compound of the present invention can be produced by the following method.
  • Compounds [Va] and [IVb] can be obtained by reacting compound [VII] with compound [1Vb] in the presence of a dehydrating condensing agent such as dicyclohexylcarpoimide (DCC).
  • a dehydrating condensing agent such as dicyclohexylcarpoimide (DCC).
  • DCC dicyclohexylcarpoimide
  • a solvent used in the reaction with DCC or the like methylene chloride, chloroform, toluene, ethyl acetate, DMF, THF, dimethoxetane, acetonitrile, t-amyl alcohol and the like are used.
  • the reaction mixture is stirred at a temperature ranging from ⁇ 10 ° C. to the boiling point of the solvent used until the reaction is completed.
  • the reaction mixture is worked up in the usual way.
  • Compounds [IVa] and [IVb] are used as a mixture in the next rearrangement reaction.
  • the rearrangement reaction is performed in the presence of a cyano compound and a mild base. That is, 1 mol of the compounds [IVa] and [IVb] is preferably 1 to 4 mol of a base, preferably Is reacted with 1-2 mol of a base and from 0.01 mol to 1.0 mol, preferably from 0.05 mol to 0.2 mol, of a cyanide compound to obtain a compound represented by the formula U] Things.
  • any of the above bases can be exemplified.
  • the cyano compound potassium cyanide, sodium cyanide, acetone cyanohydrin, hydrogen cyanide, a polymer holding potassium cyanide, or the like is used.
  • the reaction is completed in a shorter time by adding a small amount of a phase transfer catalyst such as crown ether.
  • the reaction temperature is preferably lower than 80 ° C, more preferably room temperature to 40 ° C.
  • the solvents used are 1,2-dichloroethane, chloroform, toluene, acetonitril, methylene chloride, ethyl acetate, DMF, methylisobutyl ketone, THF, dimethoxetane, and the like.
  • a similar reaction proceeds by adding the cyanide and the base to the reaction system without isolating the compounds [IVa] and [IVb].
  • This rearrangement reaction can also be carried out in a solvent in the presence of a base such as potassium carbonate, sodium carbonate, triethylamine, pyridine and the like.
  • a base such as potassium carbonate, sodium carbonate, triethylamine, pyridine and the like.
  • the amount of the base used is 0.5 to 2.0 mol with respect to the compounds [IVa] and [IVb], and the solvent is THF, dioxane, t-amyl alcohol, t-butyl alcohol. Etc. are used.
  • the reaction temperature is preferably from room temperature to the boiling point of the solvent used.
  • R 1 and R 2 have the same meanings as described above, and R 7 is a hydrogen atom or lower alkyl. And W represents a halogen atom.
  • toluene derivative (1) From the toluene derivative (1), a known method such as a simple halogen such as chlorine or bromine, or a halogenating agent such as N-bromosuccinic acid imide (NBS) or N-chlorosuccinic acid imid (NCS) is used.
  • NBS N-bromosuccinic acid imide
  • NCS N-chlorosuccinic acid imid
  • Benzyl halide derivative (2) by reacting in the presence of a radical initiator such as light or benzoylperoxide to obtain a benzyl halide derivative (2), for example, J. Am. Chem. Soc. , 7 1, 1 767 (1 949) can be used to produce the aldehyde form (3).
  • the carboxylic acid compound (4) is converted from the toluene derivative (1) by an oxidation reaction of permanganic acid or the like, or from the aldehyde compound (3) by a J0nes reagent, chromic acid or permanganate. It can be produced by a known method such as oxidation reaction of lime.
  • R 1, R; R 7 are as defined above, R H, R u represents a lower alkyl group.
  • the alcohol form (6) is produced by reacting the aldehyde form (3) with a Grignard reagent, and the alcohol form (6) is oxidized with activated manganese dioxide and chromic acids. Then, a 3-acyl body (7) can be obtained.
  • Examples of the catalyst used in the reaction for producing the aldol compound (10) include metal hydroxides such as sodium hydroxide and barium hydroxide, and organic bases such as piperidine and pyridine.
  • Examples of the catalyst used for the dehydration reaction include acids such as concentrated sulfuric acid and p-toluenesulfonic acid.
  • Examples of the solvent include hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as dichloromethane and chloroform.
  • the vinyl ketone compound (11) may be prepared by treating the aldehyde compound (3) and the phosphorane (9) in a suitable solvent at a temperature between room temperature and the boiling point of the solvent used for 10 minutes to 3 minutes. It can also be obtained by reacting for 0 hours.
  • the 3-diketon body (8) can be manufactured as follows.
  • R 1 , R 2 , and R 7 represent the same meaning as described above, and R and R ′ ⁇ R 1 ′ each independently represent a lower alkyl group.
  • R 1 , R 2 , R 4 , R 5 , and R 7 represent the same meaning as described above.
  • the isoxazole compound (13) is obtained by reacting the vinyl ketone compound (111) with hydroxylamine in an inert solvent at a temperature from 0 ° C to the boiling point of the solvent used for 0.5 to 5 hours. After obtaining the oxime form (12), it can be produced by further ring closure and oxidation reaction. In this oximation reaction, the hydroxyamine can be reacted in the form of sulfate or hydrochloride without neutralization, but can also be reacted after neutralization by using an appropriate base.
  • solvents examples include alcohols such as methanol, ethanol and isopropanol; hydrocarbons such as benzene and toluene; halogenated hydrocarbons such as dichloromethane and chloroform; ethers such as THF and dioxane; Examples thereof include nitriles such as tonitrile, DMF, pyridine, acetic acid, water and the like, and a mixed solvent of two or more of these solvents.
  • alcohols such as methanol, ethanol and isopropanol
  • hydrocarbons such as benzene and toluene
  • halogenated hydrocarbons such as dichloromethane and chloroform
  • ethers such as THF and dioxane
  • examples thereof include nitriles such as tonitrile, DMF, pyridine, acetic acid, water and the like, and a mixed solvent of two or more of these solvents.
  • the solvent examples include alcohols such as methanol, ethanol, and isopropanol; hydrocarbons such as benzene and toluene; halogenated hydrocarbons such as dichloromethane and chloroform; ethers such as THF and dioxane; and acetonitrile.
  • alcohols such as methanol, ethanol, and isopropanol
  • hydrocarbons such as benzene and toluene
  • halogenated hydrocarbons such as dichloromethane and chloroform
  • ethers such as THF and dioxane
  • acetonitrile examples include nitriles, DMF, pyridine, acetic acid, water and the like, and a mixed solvent of two or more of these solvents.
  • a solvent such as a non-protonic polar solvent or an alcohol such as methanol or ethanol
  • hydrochloric acid 1.0 mol to 2.0 mol of hydrochloric acid. It is carried out by reacting hydroxylamin or hydroxylamine sulfate. In addition, hydroxylamine is replaced with an appropriate base. And used in the free form. The reaction is carried out in a temperature range from room temperature to the boiling point of the solvent used. Further, it is also preferable to add an acid catalyst such as P-toluenesulfonic acid, sulfuric acid, or hydrochloric acid in order to complete the ring-closing reaction after adding hydroxyamine.
  • an acid catalyst such as P-toluenesulfonic acid, sulfuric acid, or hydrochloric acid
  • benzoic acids represented by the formula (1-1) react with the 4-carbohydrate represented by the formula (I-2) in the presence of a base in the presence of a mercaptan represented by R'SH. Therefore, it can be produced by converting it to the 4-SR 'isomer represented by the formula (I-13) and then oxidizing it.
  • R ′, R 2 , R 3 and R 7 have the same meaning as described above, and R ′ represents a d- ⁇ alkyl group.
  • Solvents used in the reaction include alcohols such as methanol and ethanol, ethers such as THF and 1,2-dimethoxetane (DME), and amines such as DMF and N, N-dimethylacetamide (DMA). And dimethylsulfoxide (DMSO), acetonitrile, benzene, toluene, xylene and the like.
  • the next oxidation reaction is carried out in an inert solvent such as water, an organic acid such as acetic acid, dichloromethane, chloroform, halogenated hydrocarbon such as carbon tetrachloride, hydrogen peroxide, peracetic acid, perbenzoic acid, m -It is carried out using an oxidizing agent such as peracid such as perbenzoic acid, sodium hypochlorite, and hypochlorous acid such as potassium hypochlorite.
  • an oxidizing agent such as peracid such as perbenzoic acid, sodium hypochlorite, and hypochlorous acid such as potassium hypochlorite.
  • isoxoxazole (13) can also be produced by the method described in WO 96Z26206. The method is described below.
  • 1-Ethyl hydrochloride 5 Dissolve 0.41 g (2.8 mimol) of hydroxypyrazole and 0.56 g (5.5 mimol) of triethylamine in 10 ml of methylene chloride.
  • Methoxyl 4-methanesulfonyl-3- (3-methyl-1-, 2-isoxazozol-5-yl) benzoyl chloride 0.82 g (2.5 mimol) of methylene chloride solution 3 m 1 was added dropwise at room temperature and stirred at room temperature for 1 hour. The reaction mixture was washed with 1N hydrochloric acid and then with saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
  • reaction mixture was poured into iced water, extracted with ethyl ether, washed with saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 2.04 g of methyl 2-methoxy-3- (3- Methyl-1,2-isoxazol-5-yl) -14-methylthiobenzoate was obtained.
  • Compound A used in Comparative Examples is a compound described in JP-A-2-1733
  • B is a compound described in W093 / 18031
  • C and D are WO It is a compound of the compound described in JP-A-96 / 26206.
  • the compound of the present invention shows high herbicidal activity under any conditions of upland crops, soil treatment and foliage treatment. Some compounds also show selectivity.
  • the compound of the present invention also includes a compound exhibiting a plant growth regulating action for producing growth suppression and the like against useful plants such as crops, ornamental plants and fruit trees.
  • the compound of the present invention has excellent herbicidal activity against various paddy weeds such as paddy weeds such as Nobie, Tamagayari, Omodaka and Firefly, and also includes a compound showing selectivity to rice.
  • the compound of the present invention can be applied to the control of weeds in orchards, lawns, track ends, vacant lots and the like.
  • the compounds of the present invention also include those having a plant growth regulating action, a bactericidal activity, and an insecticidal / miticidal activity. (Some intermediate compounds of the compound of the present invention include those having herbicidal activity.)
  • the herbicide of the present invention contains one or more of the compounds of the present invention as an active ingredient.
  • the compound of the present invention can be used in a pure form without adding other components, and can be used in the form of a general pesticide for the purpose of using it as a pesticide, that is, a wettable powder, a granule, a powder, It can also be used in the form of emulsions, aqueous solvents, suspensions, flowables and the like.
  • the herbicide of the present invention can also be used by mixing with known fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers, and the like.
  • the synergistic action of the mixed drug can be expected to have a higher effect. In that case, a combination with a plurality of known herbicides is also possible.
  • Suitable agents to be used in combination with the herbicide of the present invention include anilide-based herbicides such as diflufenican and propanil, and black mouth such as arachlor and pretilachlor.
  • anilide-based herbicides such as diflufenican and propanil
  • black mouth such as arachlor and pretilachlor.
  • Acetanilide herbicides 2,4-D, 2,4-DB, etc. aryloxyalkanoic acid herbicides, diclohop-methyl, phenoxaprop-ethyl, etc.
  • the above mixture was uniformly mixed and finely pulverized, and then granulated into particles having a diameter of 0.5 to 10 mm to obtain granules having an active ingredient content of 5%.
  • the numbers 1, 3, 5, 7, and 9 are intermediate values between 0 and 2, 2 and 4, 4 and 6, 6 and 8, and 8 and 10, respectively.
  • a 200 cm 2 pot was filled with soil, and seedlings of Inubu, Onomamomi, Aquinoe nokorogosa, Empaku, maize, and wheat were sown on the surface layer, and the seedlings were lightly covered and grown in a greenhouse.
  • seedlings of Inubu, Onomamomi, Aquinoe nokorogosa, Empaku, maize, and wheat were sown on the surface layer, and the seedlings were lightly covered and grown in a greenhouse.
  • crop damage and herbicidal effects were examined according to the above-mentioned survey criteria. The results are shown in Table 2.

Abstract

Composés représentés par la formule générale (I), ou leurs sels, dans laquelle R1 représente alcoxy C¿1?-C6 ou haloalkyle C1-C6, R?2¿ représente halogéno, alkylsulfonyle C¿1?-C6, etc., R?3¿ représente alkyle C¿1?-C6, haloalkyle C1-C6, etc., et R?4, R5 et R6¿ représentent chacun hydrogène, alkyle C¿1?-C6, etc. Les compositions contenant ces composés sont utiles comme herbicides sélectifs présentant une sélectivité par rapport aux plantes cultivées telles que le blé et le maïs.
PCT/JP1997/000340 1996-04-26 1997-02-10 Derives du benzene substitues par des heterocycles, et herbicides WO1997041116A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU16707/97A AU1670797A (en) 1996-04-26 1997-02-10 Benzene derivatives substituted by heterocycles and herbicides

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
JP8/131170 1996-04-26
JP13117096 1996-04-26
JP8/317154 1996-11-13
JP31715496 1996-11-13
JP31715396 1996-11-13
JP8/317153 1996-11-13
JP8/356866 1996-12-26
JP35686696 1996-12-26

Publications (1)

Publication Number Publication Date
WO1997041116A1 true WO1997041116A1 (fr) 1997-11-06

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AU (1) AU1670797A (fr)
WO (1) WO1997041116A1 (fr)

Cited By (86)

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EP0891972A1 (fr) * 1996-03-26 1999-01-20 Nippon Soda Co., Ltd. Derives d'acide benzoique a substitution 3-(isoxazol-5-yl) et leur procede de production
WO1999054328A1 (fr) * 1998-04-22 1999-10-28 Nippon Soda Co., Ltd. Nouveau composes de benzoylpyrazole et herbicide
WO2000034247A2 (fr) * 1998-12-04 2000-06-15 Basf Aktiengesellschaft Procede de production de derives de pyrazolylbenzoyl et nouveaux derives de pyrazolylbenzoyl
US6479437B1 (en) 1998-06-09 2002-11-12 Basf Aktiengesellschaft Herbicidal mixture containing a 3-heterocyclyl-substituted benzoyl derivative
US6514910B1 (en) 1999-03-05 2003-02-04 Basf Aktiengesellschaft Herbicidal mixture containing a 3-heterocyclyl-substituted benzoyl derivative and an adjuvant
JP2003518114A (ja) * 1999-12-22 2003-06-03 ビーエーエスエフ アクチェンゲゼルシャフト ３−（４，５−ジヒドロイソオキサゾール−５−イル）ベンゾイルピラゾール
US6610631B1 (en) 1999-09-30 2003-08-26 Bayer Aktiengesellschaft Substituted aryl ketones
US6746989B1 (en) 1999-03-27 2004-06-08 Bayer Aktiengesellschaft Substituted benzoylpyrazoles as herbicides
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US6864219B2 (en) 2000-01-17 2005-03-08 Bayer Aktiengesellschaft Substituted aryl ketones
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