WO1997041117A1 - Nouveaux derives du benzene substitues par des heterocycles, et herbicides - Google Patents

Nouveaux derives du benzene substitues par des heterocycles, et herbicides Download PDF

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Publication number
WO1997041117A1
WO1997041117A1 PCT/JP1997/000342 JP9700342W WO9741117A1 WO 1997041117 A1 WO1997041117 A1 WO 1997041117A1 JP 9700342 W JP9700342 W JP 9700342W WO 9741117 A1 WO9741117 A1 WO 9741117A1
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Prior art keywords
methyl
compound
solvent
benzoyl
group
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PCT/JP1997/000342
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English (en)
Japanese (ja)
Inventor
Hiroyuki Adachi
Masao Yamaguchi
Osamu Miyahara
Masami Koguchi
Kazuyuki Tomita
Akihiro Takahashi
Takashi Kawana
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Nippon Soda Co., Ltd.
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Priority to AU16709/97A priority Critical patent/AU1670997A/en
Publication of WO1997041117A1 publication Critical patent/WO1997041117A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • C07D417/10—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 linked by a carbon chain containing aromatic rings

Definitions

  • the present invention relates to a birazol derivative in which a benzoyl group is substituted at the 4-position of the birazol ring, in particular, a novel benzozol derivative having an isoxazole-5-yl group at the 3-position of the benzoyl moiety, and the compound is effectively used. It relates to a herbicide as a component.
  • a compound represented by the formula (IV) is described in WO96 / 26206.
  • a 3-position heterocyclic group in the benzoyl moiety Z, oxazolyl 5-yl, thiazo Compounds such as Lou 2 -yl and isoxazol-3-yl groups have been specifically described and synthesized.
  • An object of the present invention is to provide a herbicide which can be synthesized industrially advantageously, has a lower dose, is more effective, and has high selectivity to crops.
  • the present applicants have conducted intensive studies and found that among the compounds represented by the general formula [IV], the 3-position heterocyclic group in the benzoyl moiety is a isoxazole-5-yl group, and the 2-position substituent Have found that compounds having a halogen atom have remarkably superior herbicidal activity and crop selectivity, especially wheat and corn selectivity, as compared with other heterocyclic group compounds.
  • the present invention provides a 4-benzoylvirazole compound or a salt thereof, in which the 3-position of the benzoyl moiety represented by the general formula [I] is substituted with an isooxosazole-l-5-yl group, and a salt thereof. It is a herbicide characterized by containing
  • R 1 represents a halogen atom such as fluorine, chlorine, and bromine
  • R 2 represents fluorine.
  • R 3 is a hydrogen atom or methyl, ethyl, propyl, or isopropyl
  • R 4 , R 5 and R 6 each independently represent a hydrogen atom, a methyl group or an ethyl group, etc.
  • R ′ is a chlorine atom
  • R 2 is a chlorine atom or a methylsulfonyl group
  • R 3 is a methyl group or an ethyl group, and is a methyl group.
  • a compound in which R 5 and R 6 are hydrogen atoms has particularly excellent herbicidal activity and is excellent in wheat and corn selectivity.
  • the compound of the present invention can be produced by the following method.
  • RR 2, R 3, R e are as defined above, Q is a halogen atom, an alkylcarbonyl O alkoxy group, an alkoxycarbonyl O alkoxy group or Benzoiru Okishi group, H et is a substituted group Represents an isoxazolyl 5-yl group which may have
  • compound [Vila] and [Vllb] are compound [V] and compound [V 1a] (Q represents the same meaning as described above.) It can be obtained by using 1 mol of each or one of them in excess and reacting in the presence of 1 mol or an excess of base.
  • the base used in this reaction is an alkali metal such as sodium hydroxide or sodium hydroxide, or an alkali metal such as sodium hydroxide or sodium carbonate.
  • Alkaline earth metal hydroxides such as metal carbonate, calcium hydroxide and magnesium hydroxide; alkaline earth metal carbonates such as calcium carbonate; triethylamine, triisopropylethylamine, etc.
  • Organic bases such as ( cfialkyl ) amine and pyridine, sodium phosphate and the like can be exemplified.
  • Examples of the solvent used include water, methylene chloride, chloroform, and toluene.
  • phase transfer catalyst such as a quaternary ammonium salt
  • the compounds [VI Ia] and [Vl Ib] can be obtained by reacting the compound [V] with the compound [Vlb] in the presence of a dehydrating condensing agent such as DCC. Can be done.
  • Solvents used in the reaction with DCC, etc. include methylene chloride, chloroform, toluene, ethyl acetate, dimethylformamide, THF, dimethoxetane, acetonitril, and t-amyl alcohol. And the like. Reaction temperatures range from 110 ° C. to the boiling point of the solvent used.
  • the subsequent rearrangement is performed in the presence of a cyano compound and a mild base.
  • One mole of the compounds [VIIa] and [VIIb] are treated with 1 to 4 moles of a base, preferably 1 to 2 moles of a base and 0.01 to 1 moles of the above compound, for example.
  • the reaction is carried out with 0 mol, preferably 0-0.5 mol to 0.5 mol of the cyanide.
  • the base used here is an alkali metal such as hydroxide hydroxide, sodium hydroxide, etc.
  • Organic bases such as l- (d- ⁇ - alkyl) amine and pyridine, sodium phosphate and the like can be exemplified.
  • the cyano compound potassium cyanide, sodium cyanide, acetate cyanohydrin, hydrogen cyanide, a polymer having a cyanide power beam, or the like is used. .
  • a phase transfer catalyst such as crown ether since the reaction is completed in a shorter time.
  • the reaction temperature is lower at 80, preferably from room temperature to 40 ° C.
  • Solvents used include 1,2-dichloroethane, toluene, acetate nitrile, methylene chloride, culoform form, ethyl acetate, dimethylformamide, methylisoptilketone, THF, dimethylkisthetan, and the like.
  • This rearrangement reaction can also be carried out in a solvent in the presence of a base such as sodium carbonate, sodium carbonate, triethylamine, or pyridine.
  • a base such as sodium carbonate, sodium carbonate, triethylamine, or pyridine.
  • the amount of the base used is 0.5 to 2.0 mol for the compounds [Vila] and [Vllb], and the solvents are THF, dioxane, t-amino alcohol, t-butyl. Alcohol or the like is used.
  • the reaction temperature is preferably from room temperature to the boiling point of the solvent used.
  • compound [I] can also be produced by reacting a base with a dehydrating condensing agent such as DCC without isolating compounds [Vila] and [Vllb].
  • the base used in the reaction includes potassium carbonate, sodium carbonate, triethylamine, pyridine and the like, and the amount of the base used is preferably that relative to compound (I). , 0.5 to 2.0 times mol.
  • the solvent used is THF, dioxane, t-amino alcohol, t-butyl alcohol and the like, and the reaction proceeds smoothly in a temperature range from room temperature to the boiling point of the solvent used.
  • 5-Hydroxypyrazoles represented by the general formula [V] can be prepared by a known method, for example, as described in JP-A-62-234069 and JP-A-3-44437. And the like.
  • the aldehyde (3) and the carboxylic acid (4), which are important synthetic intermediates for producing the compound of the present invention, can be produced as follows.
  • R 1 and R 2 represent the same meaning as described above, R represents a hydrogen atom or a lower alkyl group, and W represents a halogen atom.
  • halogenation such as chlorine or bromine
  • halogenating agent such as N-bromosuccinic acid imide (NBS) or N-chlorosuccinic acid imid (NCS)
  • NBS N-bromosuccinic acid imide
  • NCS N-chlorosuccinic acid imid
  • a benzyl halide derivative (2) is obtained by reacting in the presence of a radical reaction initiator such as benzoyl peroxide, for example, J. Am. Chem. Soc., 71
  • the aldehyde form (3) can be produced by the method described in J., 167 (1949).
  • an alkali metal salt of a ditroalkane such as 2-nitroprono with a metal salt in an alcohol solvent such as methanol or ethanol at a temperature between 0 ° C and the boiling point of the solvent.
  • an alcohol solvent such as methanol or ethanol
  • the carboxylic acid compound (4) is converted from the toluene derivative (1) by an oxidation reaction such as permanganate rim, or from the aldehyde compound (3) by the Jones reagent, chromic acid or permanganate. It can be produced by a known method such as an oxidation reaction using an oxidizing agent such as a rim.
  • R 1 , R 2 , R 4 , and R 5 represent the same meaning as described above, R represents a lower alkyl group, and V represents a halogen atom.
  • the alcohol form (6) is prepared by reacting the aldehyde form (3) with a Grignard reagent to produce an alcohol form (5), and the alcohol form (5) is activated with manganese dioxide and chromium. Oxidation with an acid can produce the corresponding acyl form (6).
  • the vinyl ketone compound (7) can be prepared by a method known in the literature, for example, aldehyde according to the method described in 0 rg.Syn., Co11.Vo1., ⁇ , 77 (1941).
  • the reaction is carried out at 0 for 1 to 50 hours to produce an aldol derivative (8), and the aldol derivative (8) is dehydrated in an appropriate solvent in the presence of a catalyst.
  • Examples of the catalyst used in the reaction for producing the aldol derivative (8) include metal hydroxides such as sodium hydroxide and barium hydroxide, and organic bases such as piperidine and pyridine. And the like.
  • Examples of the catalyst used in the dehydration reaction include concentrated sulfuric acid and p-toluenesulfonic acid.
  • examples of the solvent for the dehydration reaction include hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as dichloromethane and chloroform. Can be used.
  • the vinyl ketone (7) reacts the aldehyde (3) and phosphorane (10) in a suitable solvent at a temperature between room temperature and the boiling point of the solvent used for 10 minutes to 30 hours. It can also be manufactured by performing the above.
  • the diketone body (12) can be manufactured as follows.
  • R 1 , R 2 , R 4 , R 5 , and R represent the same meaning as described above, and R 6 represents a lower alkyl group.
  • the carboxylic acid compound (4) is converted to phosgene, thionyl chloride, oxalyl chloride, etc. in an inert solvent such as hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as methylene chloride and macroform.
  • an inert solvent such as hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as methylene chloride and macroform.
  • the diketone form (12) is produced by reacting the 3-ketoester (13) with a magnesium salt obtained from magnesium alcoholate and the carbonyl chloride form (11) according to a known method. can do.
  • the isoxazolyl ring intermediate can be produced by the method shown below.
  • the isooxazole derivative represented by the general formula (15) is obtained by converting the vinylketone derivative (7) and hydroxyamine into a suitable solvent at a temperature between 0 ° C and the boiling point of the solvent used. The reaction can be carried out for 5 to 30 hours to obtain an oxime compound (14), which can be further subjected to ring closure and oxidation reaction to produce the compound. Hydroxylamine used in this oximation reaction is used in the form of sulfate or hydrochloride, and can be reacted without neutralization, or can be reacted after neutralization with an appropriate base.
  • Bases used for neutralization include sodium bicarbonate, carbonates such as carbon dioxide spheres, sodium hydroxide, alkali metal hydrates such as hydroxide spheres and the like. And carboxylic acid salts such as sodium acetate, metal alcoholates such as sodium methylate and sodium ethylate, and organic bases such as triethylamine and pyridine.
  • the solvent to be used include alcohols such as methanol, ethanol and isopropanol, hydrocarbons such as benzene and toluene, halogenated hydrocarbons such as dichloromethane and chloroform, and TH.
  • Examples thereof include ethers such as F and dioxane, nitriles such as acetate nitrile, DMF, pyridine, acetic acid, water and the like, and a mixed solvent of two or more of these solvents.
  • ethers such as F and dioxane
  • nitriles such as acetate nitrile, DMF, pyridine, acetic acid, water and the like
  • a mixed solvent of two or more of these solvents for the ring closure / oxidation reaction, potassium iodide, N-prosuccinimide, palladium catalyst system and the like are used, and are described in J. Amer. Chem. Soc., 94, 9 respectively. J. H eterocycl. Chem., 14, 1289 (1977); T etrahedron Lett.
  • the isoxazole compound represented by the general formula (16) can be produced by reacting the diketone compound (12) with a hydroxylamine or a hydroxylamine salt, respectively.
  • acids such as sulfuric acid and p-toluenesulfonic acid can be used as a catalyst.
  • the solvent include alcohols such as methanol, ethanol, and isopropanol; hydrocarbons such as benzene and toluene; and halogenated hydrocarbons such as dichloromethane and chloroform. , Ethers such as THF and dioxane, nitriles such as acetonitril, DMF, pyridin, acetic acid, water and the like, and a mixed solvent of two or more of these solvents.
  • the isoxazole compound represented by the general formula (16) is obtained by using the 3-acyl compound (6) as a starting material and N, N-dimethyl such as N, N-dimethylformamide dimethyl acetal. After reacting with an alkyl amide dialkyl acetal to obtain a dialkyl amino methylidene compound represented by the formula (17), this is reacted with hydroxylamine or hydroxyamine salt. It can also be manufactured by making it work.
  • reaction in the previous step is performed without solvent or in an inert solvent such as benzene, toluene and xylene from room temperature to the boiling point of the solvent used (in the absence of solvent, the boiling point of N, N dimethylalkylamide dimethyl acetal) It is performed in the temperature range up to.
  • an inert solvent such as benzene, toluene and xylene
  • reaction is carried out, for example, using dioxane, ether, tetrahydrofuran, ether solvents such as 1,2-dimethyloxetane (DME), N, N-dimethylformamide (DMF),
  • ether solvents such as 1,2-dimethyloxetane (DME), N, N-dimethylformamide (DMF)
  • DME 1,2-dimethyloxetane
  • DMF N, N-dimethylformamide
  • a nonprotonic polar solvent such as tyl sulfoxide (DMS ⁇ ) or a solvent such as alcohol such as methanol or ethanol
  • DME 1,2-dimethyloxetane
  • DMF 1,2-dimethyloxetane
  • DMF 1,2-dimethyloxetane
  • DMF 1,2-dimethyloxetane
  • DMF 1,2-dimethyloxetane
  • DMF 1,2-dimethyloxe
  • the reaction is carried out from room temperature It is carried out in the temperature range up to the boiling point. Further, it is also preferable to add an acid catalyst such as p_toluenesulfonic acid, sulfuric acid, or hydrochloric acid after completing the addition of hydroxylamin to complete the ring closure reaction.
  • an acid catalyst such as p_toluenesulfonic acid, sulfuric acid, or hydrochloric acid
  • the isoxazole form represented by the general formula (19) is represented by R'SH in the presence of a base in the 2,4-dichloroform body represented by the formula (20) the Merukabuta down by a work, 4 one SR "After the body (2 1), the corresponding 4 by the oxidation reaction - S 0 2 R" can be produced body (1 9).
  • the base used when reacting R'SH include sodium hydroxide, hydroxides such as sodium hydroxide, sodium methoxide, sodium ethoxide and the like. Alkoxides, sodium carbonate, carbonated lithium
  • Examples thereof include carbonates such as sodium hydride, hydrides such as sodium hydride, and organic bases such as tritylamine, diisopropylamine, pyridine, pyridine, and DBU.
  • the next oxidation reaction is carried out in water, an organic acid such as acetic acid, a halogenated solvent such as dichloromethane, chloroform, carbon tetrachloride, hydrogen peroxide, peracetic acid, perbenzoic acid, and m-chloroperoxide. This is performed using an oxidizing agent such as benzoic acid.
  • the reaction is carried out in a temperature range from room temperature to the boiling point of the solvent used.
  • a mercapbutane salt is prepared by reacting mercaptan with a base in advance, and this is reacted with a compound represented by the formula (20) to obtain a compound represented by the formula:
  • the compound represented by (21) can be obtained.
  • the compound (13) can be produced by the method described in WO966Z22606. The method is described below.
  • the compound [I] contains a free hydroxyl group by the above-mentioned method, that is, the compound [I], the corresponding salt, particularly an agro-horticulturally acceptable one, is obtained from the compound.
  • the resulting salt can be derived.
  • Agro-horticulturally acceptable salts include salts of sodium, calcium, calcium, ammonium and the like.
  • Ra Rb Rc Rd (wherein, Ra, Rb, Rc, and R d are each independently Takoto 1 is replaced by, for example, heat Dorokishi group by hydrogen and optionally ⁇ C '° represents an alkyl group.) If any of Ra, Rb, Rc and Rd is an optionally substituted alkyl group, it is preferred that they contain 1-4 carbon atoms. These derivatives can be manufactured by a conventional method.
  • the compound of the present invention and various intermediates can be obtained by ordinary post-treatment.
  • the structures of the compound of the present invention and various intermediates are determined from IR, NMR, MS spectra and the like.
  • Hydrochloric acid 5 Hydroxy 1 — Methyl virazole 1.27 g and triethylamine 1.92 g are dissolved in methylene chloride 20 m 1, and 2,4 — dichloro mouth — 3 — ( 3—Methyl—1,2—Isoxazolyl 5- (yl) benzoyl chloride 2.70 g of methylene chloride (10 m) solution was added dropwise at room temperature, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was washed with 1N hydrochloric acid and then with saturated saline, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure.
  • Hydrochloric acid 1 Ethyl mono 5—Hydroxypyrazole 4.46 g and 2,4—Dichloro-1- (3-Methyl-1,2—Isoxazolyl-5—yl) benzoyl chloride 8.24 g was dissolved in black mouth form 40 m 1, and triethylamine 6.36 g was added dropwise under water cooling, followed by stirring at room temperature for 25 minutes. To the reaction mixture, 3.64 g of triethylamine and 0.51 g of acetantocyanhydrin were added, and the mixture was stirred at room temperature for one hour. Water was added to the reaction mixture, and the mixture was made alkaline with a 10% aqueous sodium hydroxide solution.
  • the obtained crude oxime compound was dissolved in 30 ml of toluene, 0.5 g of p-toluenesulfonic acid was added, and the mixture was stirred under heating and reflux for 14.5 hours. After cooling, the reaction solution was washed with water and saturated saline, and dried over magnesium sulfate. After the solvent was concentrated under reduced pressure, the obtained residue was purified by silica gel mouth chromatography to give the target product, methyl 2,4-dichloromethane-3— (4-me Chilly soxazole-5-yl) The benzoate 0.83 g was obtained.
  • the compound of the present invention shows high herbicidal activity under any conditions of upland crops, soil treatment and foliage treatment, and shows high potency against various field weeds such as Aquinoeno korogusa, Ponamimi, inubu and Empaku, It also contains compounds that are selective for crops such as corn, wheat, barley and other barley crops, and soybeans and ivy.
  • 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 weeds such as paddy field weeds such as Nobie, Tamagayari, Omodaka, and Hoyu Rui, and also includes compounds having rice selectivity.
  • the compound of the present invention can also be applied to the control of weeds in orchards, lawns, track ends, vacant lots and the like.
  • 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 in the form of a general pesticide for use as a pesticide, that is, a wettable powder, a granule It can also be used in the form of powders, emulsions, aqueous solvents, suspensions, flowables and the like.
  • soybean flour, flour and other plant powders When solid additives are used as additives and carriers, soybean flour, flour and other plant powders, diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay Organic and inorganic compounds such as mineral fine powder such as sodium benzoate, urea and sodium sulfate are used.
  • petroleum fractions such as kerosene, xylene and sorbent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetate , Trichlorethylene, methyl isoptil ketone, mineral oil, vegetable oil, water, etc. as solvents.
  • Surfactants can be added, if necessary, to obtain a uniform and stable form in these preparations.
  • the concentration of the active ingredient in the herbicide of the present invention varies depending on the form of the preparation described above.
  • the concentration is 5 to 90%, preferably 10 to 10%. 85%: 3 to 70% in emulsion, preferably 5 to 60%: 0.01 to 50% in granules, preferably 0.0 to 50% 5% to 40% concentration is used
  • the wettable powder and emulsion thus obtained are diluted to a predetermined concentration with water to form a suspension or emulsion, and the granules can be sprayed before or after germination of the weeds.
  • the soil will be mixed.
  • an appropriate amount of 0.1 g or more of the active ingredient is applied per hectare.
  • the herbicide of the present invention can be used in combination with known fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers, and the like.
  • synergistic action of the mixed drug can be expected to have higher effects.
  • 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 herbicides such as diflupanican and propanil, and black-mouth aceroalide-based herbicides such as arlacrol and prepilachlor, and 2, 4-D. , 2,4-DB, etc. aryloxy-acid herbicides, diclohop-methyl, phenyloxaprop-ethyl, etc., aryloxy-phenyloxyalkanoic acid herbicides, dicampa, pyritiobac, etc.
  • anilide herbicides such as diflupanican and propanil
  • black-mouth aceroalide-based herbicides such as arlacrol and prepilachlor
  • 2, 4-D. , 2,4-DB, etc. aryloxy-acid herbicides, diclohop-methyl, phenyloxaprop-ethyl, etc., aryloxy-phenyloxyalkanoic acid herbicides, dicampa, pyr
  • Aryl carboxylic acid herbicides imazaquinone, imazethapyr, etc., imidazolinone herbicides, zirone, isoprolon, etc., urea herbicides, chlorprofam, fenmedifam, etc., carbamate herbicides Thiocarbamate herbicides such as thiobencalp, EPTC, etc., and dinitro-lower such as trifluralin and pendimethalin.
  • Herbicides difluoroether herbicides such as acifluorfen, homesaphene, etc .; sulfonylrea herbicides such as bensulfuron-methyl, nicosulfuron, etc .; Herbicides, triazine herbicides such as atrazine and cyanazine, triazopyrimidine herbicides such as flumellam, ditolyl herbicides such as promoxinil and diclobenyl, chloridazone Pyridazinone herbicides such as norflurazon, phosphoric acid herbicides such as glyphosate and glufosinate, and quaternary ammonium salt herbicides such as paracoat and difenzocolate; —Cyclic imid herbicides such as methyl, and others such as isoxaben and etofumeset Okisajiazon, kink opening rack, click Romazo down, Surco Application Benefits on, Shinmechiri down
  • Example 1 1 granule
  • Sodium alkyl sulfate 7 parts The above mixture was uniformly mixed and finely pulverized, and then granulated into particles having a diameter of 0.5 to 1.0 mm to obtain granules having an active ingredient of 5%.
  • the herbicidal effect was investigated according to the following criteria and expressed as a herbicidal index.
  • 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.
  • the compound of the present invention has excellent herbicidal activity and crop selectivity, particularly excellent crop selectivity for wheat and corn. Therefore, the composition containing the compound of the present invention is useful as a selective herbicide for wheat and corn.

Abstract

Composés représentés par la formule générale (I), ou leurs sels, dans laquelle R1 représente halogéno, R2 représente halogéno ou alkylsulfonyle C¿1?-C6, R?3¿ représente hydrogène ou alkyle C¿1?-C6, et R?4, R5 et R6¿ représentent chacun hydrogène ou alkyle C¿1?-C6. Ces composés présentent une sélectivité par rapport aux plantes cultivées telles que le blé et le maïs. Les compositions les contenant sont utiles comme herbicides sélectifs.
PCT/JP1997/000342 1996-04-26 1997-02-10 Nouveaux derives du benzene substitues par des heterocycles, et herbicides WO1997041117A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU16709/97A AU1670997A (en) 1996-04-26 1997-02-10 Novel benzene derivatives substituted by heterocycles and herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP8/131170 1996-04-26
JP13117096 1996-04-26

Publications (1)

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WO1997041117A1 true WO1997041117A1 (fr) 1997-11-06

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KR (1) KR20000065049A (fr)
AU (1) AU1670997A (fr)
WO (1) WO1997041117A1 (fr)

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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
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US6514910B1 (en) 1999-03-05 2003-02-04 Basf Aktiengesellschaft Herbicidal mixture containing a 3-heterocyclyl-substituted benzoyl derivative and an adjuvant
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WO2006000592A1 (fr) 2004-06-28 2006-01-05 Basf Aktiengesellschaft Utilisation de polymeres contenant des groupes ether en tant qu'agents de solubilisation
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