WO2011065451A1 - Cétone et herbicide l'incluant - Google Patents

Cétone et herbicide l'incluant Download PDF

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Publication number
WO2011065451A1
WO2011065451A1 PCT/JP2010/071070 JP2010071070W WO2011065451A1 WO 2011065451 A1 WO2011065451 A1 WO 2011065451A1 JP 2010071070 W JP2010071070 W JP 2010071070W WO 2011065451 A1 WO2011065451 A1 WO 2011065451A1
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WIPO (PCT)
Prior art keywords
compound
formula
present
weeds
chloro
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PCT/JP2010/071070
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English (en)
Japanese (ja)
Inventor
雅人 高延
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住友化学株式会社
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Filing date
Publication date
Application filed by 住友化学株式会社 filed Critical 住友化学株式会社
Publication of WO2011065451A1 publication Critical patent/WO2011065451A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring

Definitions

  • the present invention relates to a ketone compound and a herbicide containing the same.
  • An object of the present invention is to provide a compound having an excellent weed control effect.
  • the present inventor has found that the ketone compound represented by the formula (I) has a weed control effect, and has led to the present invention.
  • the present invention is as follows. [1] Formula (I) A ketone compound represented by the following (hereinafter referred to as the present compound). [2] Formula (II) The method for producing a ketone compound according to [1], which comprises a step of reacting the compound represented by the formula with metachloroperbenzoic acid. [3] A herbicide containing the ketone compound according to [1] and an inert carrier.
  • [4] A method for controlling weeds, wherein an effective amount of the ketone compound according to [1] is applied to weeds, soil in which weeds grow, or soil in which weeds will grow in the future.
  • [5] Use of the ketone compound according to [1] for controlling weeds.
  • [6] Formula (II) A compound represented by [7] Formula (III): A compound of formula (IV): [Wherein, X represents a halogen atom. ]
  • the compound of the present invention has a weed control effect, it is useful as an active ingredient of a herbicide.
  • the compound of the present invention can be produced, for example, by the following production method.
  • (Production method 1) Formula (I): The compound of the present invention represented by the formula (II): It can manufacture by making the compound shown by and a metachloro perbenzoic acid react. The reaction is usually performed in a solvent. Examples of the solvent used for the reaction include halogenated hydrocarbons such as chloroform. The amount of metachloroperbenzoic acid used in the reaction is usually 2 to 4 moles per mole of the compound represented by the formula (II).
  • the reaction temperature is usually in the range of ⁇ 20 to 40 ° C.
  • the reaction time is usually in the range of 1 to 10 hours.
  • the compound of the present invention can be isolated by performing post-treatment operations such as pouring the reaction mixture into water and extracting the mixture with an organic solvent, and then drying and concentrating the organic layer.
  • the isolated compound of the present invention can be further purified by recrystallization, column chromatography or the like.
  • (Production method 2) Formula (II): The compound represented by the formula (III): A compound of formula (IV): [Wherein, X represents a halogen atom such as chlorine or bromine. ] It can manufacture by making it react with the compound shown by Lewis acid presence. The reaction is usually performed in a solvent. Examples of the Lewis acid used in the reaction include aluminum chloride.
  • the solvent used for the reaction examples include halogenated hydrocarbons such as chloroform.
  • the amount of the reagent used in the reaction is usually 1 to 2 mol of the compound represented by formula (IV) and 1 to 2 mol of Lewis acid based on 1 mol of the compound represented by formula (III). Is the ratio.
  • the reaction temperature is usually in the range of ⁇ 20 to 40 ° C.
  • the reaction time is usually in the range of 1 to 10 hours.
  • the compound represented by the formula (II) is isolated by performing post-treatment operations such as pouring the reaction mixture into water, extracting with an organic solvent, and then drying and concentrating the organic layer. can do.
  • the isolated compound represented by the formula (II) can be used in the next step without purification.
  • Formula (III) The compound represented by the formula (V): It can manufacture by making the compound and sulfide salt shown by react.
  • the reaction is usually performed in a solvent.
  • the solvent used for the reaction include aprotic polar compounds such as 1-methyl-2-pyrrolidone.
  • Examples of the sulfide salt used in the reaction include sodium sulfide nonahydrate.
  • the amount of the sulfide salt used in the reaction is usually 1 to 4 moles per mole of the compound represented by the formula (V).
  • the reaction temperature of the reaction is usually in the range of 0 to 180 ° C.
  • the reaction time is usually in the range of 1 to 20 hours.
  • the compound represented by the formula (III) is isolated by performing post-treatment operations such as pouring the reaction mixture into water, extracting with an organic solvent, and then drying and concentrating the organic layer. can do.
  • the isolated compound represented by the formula (III) can be further purified by column chromatography or the like.
  • the isolated compound represented by the formula (III) can be used in the next step without purification.
  • (Reference production method 2) Formula (V): The compound represented by the formula (VI): It can manufacture by making the compound shown by p-toluenesulfonyl chloride react. The reaction is usually performed in a basic solvent such as pyridine.
  • the amount of paratoluenesulfonyl chloride used in the reaction is usually 1 to 4 moles per mole of the compound represented by the formula (VI).
  • the reaction temperature is usually in the range of -10 to 50 ° C.
  • the reaction time is usually in the range of 1 to 10 hours.
  • the compound represented by the formula (V) is isolated by performing post-treatment operations such as pouring the reaction mixture into water, extracting with an organic solvent, and then drying and concentrating the organic layer. can do.
  • the isolated compound represented by the formula (V) can be further purified by column chromatography or the like.
  • the isolated compound represented by the formula (V) can be used in the next step without purification.
  • the compound represented by the formula (VI) is described in, for example, Journal of Medicinal Chemistry (2007) Vol. 50, (No. 12), P2818-2841.
  • the compound of the present invention has an excellent weed control effect and can be used as an active ingredient of a herbicide.
  • weeds for which the compound of the present invention is effective include paddy field weeds such as Tainubie, Inu firefly, Azena, Urikawa and the like.
  • the herbicide of the present invention contains the compound of the present invention and an inert carrier.
  • Examples of the inert carrier contained in the herbicide of the present invention include a liquid carrier and a solid carrier.
  • the herbicide of the present invention usually contains 0.01 to 90% by weight of the compound of the present invention.
  • the liquid carrier include water, alcohols (for example, methanol, ethanol, 1-propanol, 2-propanol, and ethylene glycol), ketones (for example, acetone and methyl ethyl ketone), ethers (for example, dioxane, tetrahydrofuran).
  • Solid carriers include vegetable powders (eg, soybean powder, tobacco powder, wheat flour, and wood powder), mineral powders (eg, clays such as kaolin, bentonite, acid clay, clay; talc powder, wax stone powder, etc. Talc; silica such as diatomaceous earth and mica powder), alumina, sulfur powder, activated carbon, saccharides (for example, lactose and glucose), inorganic salts (for example, calcium carbonate and sodium bicarbonate), and glass hollow bodies Can be mentioned.
  • the liquid carrier or solid carrier is contained in the herbicide of the present invention in a proportion of usually 1 to 99% by weight, preferably about 10 to 99% by weight, based on the total amount.
  • Surfactants are usually used as emulsifiers, dispersants, spreaders, penetrants, wetting agents and the like used in the formulation.
  • examples of such surfactants include negative alkyl sulfate salts, alkyl aryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphate esters, lignin sulfonates, naphthalene sulfonate formaldehyde polycondensates, and the like.
  • binder and thickener examples include, for example, dextrin, sodium salt of carboxymethyl cellulose, polycarboxylic acid polymer compound, polyvinyl pyrrolidone, polyvinyl alcohol, sodium lignin sulfonate, calcium lignin sulfonate, sodium polyacrylate, gum arabic, Examples include sodium alginate, mannitol, sorbitol, bentonite mineral, polyacrylic acid and its derivatives, sodium salt of carboxymethyl cellulose, white carbon, and natural sugar derivatives (eg, xanthan gum, guar gum, etc.).
  • the content ratio of the compound of the present invention in the preparation is, for example, as follows. 1.
  • Emulsions, wettable powders, granular wettable powders, liquids, aqueous solvents, flowables, tablets, and dry flowables Usually in a proportion of 1 to 90% by weight. 2. For oils and powders: usually 0.01 to 10% by weight. 3. Granules and jumbo agents: Usually 0.05 to 25% by weight. Emulsions, wettable powders, granular wettable powders, liquids, aqueous solvents, flowables and the like are usually used after being diluted about 100 to 100,000 times with water or the like.
  • the weed control method of the present invention is carried out by applying an effective amount of the compound of the present invention to weeds, soils on which weeds grow, or soils on which weeds will grow in the future.
  • the method for controlling weeds of the present invention is usually carried out by applying the preparation of the compound of the present invention to weeds, soils where weeds will grow, or soils where weeds will grow in the future.
  • the application method when using the compound of the present invention for controlling weeds the same methods as those for applying known ordinary agricultural chemicals are used. Examples of such application methods include soil treatment and foliage treatment.
  • the application amount of the compound of the present invention is usually 1 to 5000 g per 10,000 m 2 of application site.
  • the compound of the present invention can be used for controlling weeds in paddy fields.
  • the amount of the compound of the present invention is usually 1 to 5000 g per 10,000 m 2 of paddy field.
  • the herbicide of the present invention is usually applied before or after emergence of weeds for paddy field weed control.
  • the compound of the present invention is formulated into an emulsion, wettable powder, granule wettable powder, aqueous solvent, flowable agent, dry flowable agent, etc., the water is added so that the concentration of the compound of the present invention becomes 0.1 to 1000 ppm. It is applied by spraying after dilution.
  • the formulation is usually applied as it is.
  • the herbicide of the present invention may be applied and / or mixed simultaneously with one or more other herbicides, plant growth regulators, fungicides, insecticides, acaricides, nematicides and the like as necessary. Can be applied. .
  • a phenoxy fatty acid herbicidal compound for example, (1) a phenoxy fatty acid herbicidal compound, (2) benzoic acid herbicidal compound, (3) urea herbicidal compound, (4) a triazine herbicidal compound, (5) bipyridinium herbicidal compound, (6) hydroxybenzonitrile herbicidal compound, (7) dinitroaniline herbicidal compound, (8) an organophosphorus herbicidal compound, (9) carbamate herbicidal compounds, (10) an acid amide herbicidal compound, (11) a chloroacetanilide herbicidal compound, (12) diphenyl ether herbicidal compound, (13) a cyclic imide herbicidal compound, (14) a pyrazole herbicidal compound, (15) a triketone herbicidal compound, (16) Aryloxyphenoxypropionic acid herbicidal compound, (17) a trione oxime herbicidal compound, (18) a sulf
  • a disinfectant for example, (1) a polyhaloalkylthio fungicidal compound, (2) organophosphorus fungicidal compound, (3) benzimidazole bactericidal compound, (4) Carboxamide fungicidal compound, (6) acylalanine bactericidal compound, (7) azole fungicidal compound, (8) Morpholine bactericidal compound, (9) strobilurin bactericidal compound, (10) Antibiotics, and (11) Dithiocarbamate bactericidal compounds.
  • a polyhaloalkylthio fungicidal compound for example, (1) a polyhaloalkylthio fungicidal compound, (2) organophosphorus fungicidal compound, (3) benzimidazole bactericidal compound, (4) Carboxamide fungicidal compound, (6) acylalanine bactericidal compound, (7) azole fungicidal compound, (8) Morpholine bactericidal compound, (9)
  • an active ingredient of such an insecticide for example, (1) organophosphorus insecticidal compound, (2) carbamate insecticidal compounds, (3) pyrethroid insecticidal compound, (4) nereistoxin insecticidal compound, (5) Neonicotinoid insecticidal compound, (6) Benzoylphenylurea insecticidal compound, and (7) Macrolide insecticidal compound.
  • the herbicide of the present invention may be mixed with pigments, fertilizers (for example, urea and the like) and the like.
  • the compound of the present invention can control weeds in farmland where crops such as rice are grown.
  • Production Example 1 Synthesis of 5-benzoyl-4-chloro-2,3-dihydrobenzo [b] thiophene-1,1-dioxide 1.00 g of 4-chloro-2,3-dihydrobenzo [b] thiophene and 1.20 g of aluminum chloride were added to 10 ml of chloroform. To this mixture, 1.0 ml of benzoyl chloride was added dropwise under ice cooling. The mixture was stirred for 2 hours under ice cooling.
  • Formulation Example 2 Compound of the present invention 1.5% by weight 2% by weight sodium lignin sulfonate Talc 40% by weight Bentonite 56.5% by weight Are mixed and kneaded and granulated to obtain granules.
  • Test example 1 A plastic pot ( ⁇ 9 cm ⁇ 10 cm) was filled with soil, water was added, and the mixture was left standing for 3 days. The pot was mixed with soil mixed with Azena seeds uniformly and left in a greenhouse (20-25 ° C.) for 6 days. Water was added to the pot to a depth of 3 cm.
  • the compound of the present invention showed efficacy 8 at a treatment dose of 4000 g / ha.
  • the compound of the present invention has a weed control effect. Weeds can be controlled by applying an effective amount of the compound of the present invention to weeds, soils where weeds will grow, or soils where weeds will grow in the future.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La présente invention concerne une cétone représentée par la formule (I) qui présente un effet de maîtrise des mauvaises herbes. Les mauvaises herbes peuvent être maîtrisées par application d'une quantité active du composé aux mauvaises herbes, au sol où croissent les mauvaises herbes ou au sol où les mauvaises herbes vont croître. La présente invention concerne également : une méthode de production d'une cétone de formule (I) ; et un intermédiaire de production d'une cétone de formule (I).
PCT/JP2010/071070 2009-11-24 2010-11-18 Cétone et herbicide l'incluant WO2011065451A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2009266024 2009-11-24
JP2009-266024 2009-11-24
JP2010-041895 2010-02-26
JP2010041895 2010-02-26

Publications (1)

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WO2011065451A1 true WO2011065451A1 (fr) 2011-06-03

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JP (1) JP2011195561A (fr)
TW (1) TW201127286A (fr)
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WO2013040057A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
WO2013040033A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
WO2013040021A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
WO2013040116A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
WO2013039990A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
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WO2013040117A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
WO2013040005A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
WO2014151255A1 (fr) 2013-03-15 2014-09-25 Monsanto Technology Llc Méthodes et compositions pour lutter contre les mauvaises herbes
WO2015108982A2 (fr) 2014-01-15 2015-07-23 Monsanto Technology Llc Procédés et compositions pour la lutte contre les mauvaises herbes utilisant des polynucléotides epsps
US9121022B2 (en) 2010-03-08 2015-09-01 Monsanto Technology Llc Method for controlling herbicide-resistant plants
US9540642B2 (en) 2013-11-04 2017-01-10 The United States Of America, As Represented By The Secretary Of Agriculture Compositions and methods for controlling arthropod parasite and pest infestations
US9777288B2 (en) 2013-07-19 2017-10-03 Monsanto Technology Llc Compositions and methods for controlling leptinotarsa
US9850496B2 (en) 2013-07-19 2017-12-26 Monsanto Technology Llc Compositions and methods for controlling Leptinotarsa
US10041068B2 (en) 2013-01-01 2018-08-07 A. B. Seeds Ltd. Isolated dsRNA molecules and methods of using same for silencing target molecules of interest
US10240161B2 (en) 2012-05-24 2019-03-26 A.B. Seeds Ltd. Compositions and methods for silencing gene expression
US10378012B2 (en) 2014-07-29 2019-08-13 Monsanto Technology Llc Compositions and methods for controlling insect pests
US10557138B2 (en) 2013-12-10 2020-02-11 Beeologics, Inc. Compositions and methods for virus control in Varroa mite and bees
US10609930B2 (en) 2013-03-13 2020-04-07 Monsanto Technology Llc Methods and compositions for weed control
US10612019B2 (en) 2013-03-13 2020-04-07 Monsanto Technology Llc Methods and compositions for weed control
US10655136B2 (en) 2015-06-03 2020-05-19 Monsanto Technology Llc Methods and compositions for introducing nucleic acids into plants
US10683505B2 (en) 2013-01-01 2020-06-16 Monsanto Technology Llc Methods of introducing dsRNA to plant seeds for modulating gene expression
US10760086B2 (en) 2011-09-13 2020-09-01 Monsanto Technology Llc Methods and compositions for weed control
US10801028B2 (en) 2009-10-14 2020-10-13 Beeologics Inc. Compositions for controlling Varroa mites in bees
US10806146B2 (en) 2011-09-13 2020-10-20 Monsanto Technology Llc Methods and compositions for weed control
US10829828B2 (en) 2011-09-13 2020-11-10 Monsanto Technology Llc Methods and compositions for weed control
US10883103B2 (en) 2015-06-02 2021-01-05 Monsanto Technology Llc Compositions and methods for delivery of a polynucleotide into a plant
US10888579B2 (en) 2007-11-07 2021-01-12 Beeologics Inc. Compositions for conferring tolerance to viral disease in social insects, and the use thereof
US10968449B2 (en) 2015-01-22 2021-04-06 Monsanto Technology Llc Compositions and methods for controlling Leptinotarsa
US10988764B2 (en) 2014-06-23 2021-04-27 Monsanto Technology Llc Compositions and methods for regulating gene expression via RNA interference
US11091770B2 (en) 2014-04-01 2021-08-17 Monsanto Technology Llc Compositions and methods for controlling insect pests
US11807857B2 (en) 2014-06-25 2023-11-07 Monsanto Technology Llc Methods and compositions for delivering nucleic acids to plant cells and regulating gene expression

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US10801028B2 (en) 2009-10-14 2020-10-13 Beeologics Inc. Compositions for controlling Varroa mites in bees
US9121022B2 (en) 2010-03-08 2015-09-01 Monsanto Technology Llc Method for controlling herbicide-resistant plants
US11812738B2 (en) 2010-03-08 2023-11-14 Monsanto Technology Llc Polynucleotide molecules for gene regulation in plants
US9988634B2 (en) 2010-03-08 2018-06-05 Monsanto Technology Llc Polynucleotide molecules for gene regulation in plants
US10808249B2 (en) 2011-09-13 2020-10-20 Monsanto Technology Llc Methods and compositions for weed control
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US10829828B2 (en) 2011-09-13 2020-11-10 Monsanto Technology Llc Methods and compositions for weed control
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US10806146B2 (en) 2011-09-13 2020-10-20 Monsanto Technology Llc Methods and compositions for weed control
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US10240161B2 (en) 2012-05-24 2019-03-26 A.B. Seeds Ltd. Compositions and methods for silencing gene expression
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US10041068B2 (en) 2013-01-01 2018-08-07 A. B. Seeds Ltd. Isolated dsRNA molecules and methods of using same for silencing target molecules of interest
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US10568328B2 (en) 2013-03-15 2020-02-25 Monsanto Technology Llc Methods and compositions for weed control
WO2014151255A1 (fr) 2013-03-15 2014-09-25 Monsanto Technology Llc Méthodes et compositions pour lutter contre les mauvaises herbes
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