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WO2001000580A1 - Derives de pyridine 2-(eventuellement substituee benzoylamino)-6-(eventuellement substituee phenoxy), preparation de ces derives et herbicides - Google Patents

Derives de pyridine 2-(eventuellement substituee benzoylamino)-6-(eventuellement substituee phenoxy), preparation de ces derives et herbicides Download PDF

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Publication number
WO2001000580A1
WO2001000580A1 PCT/JP2000/004115 JP0004115W WO0100580A1 WO 2001000580 A1 WO2001000580 A1 WO 2001000580A1 JP 0004115 W JP0004115 W JP 0004115W WO 0100580 A1 WO0100580 A1 WO 0100580A1
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Prior art keywords
group
alkyl
compound
unsubstituted
alkoxy
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Legal status (The legal status 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 status listed.)
Ceased
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PCT/JP2000/004115
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English (en)
Japanese (ja)
Inventor
Susumu Shimizu
Hisashi Kanno
Tsutomu Sato
Masato Arahira
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Kureha Corp
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Kureha Corp
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Publication date
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Priority to AU2000254293A priority Critical patent/AU2000254293A1/en
Publication of WO2001000580A1 publication Critical patent/WO2001000580A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

Definitions

  • the present invention relates to 2- (unsubstituted or substituted) benzoylamino-6- (unsubstituted or
  • 6- (unsubstituted or substituted) phenoxypicolinic acids are disclosed in Japanese Patent Application Laid-Open Nos. Hei 1991-1985, Hei 4-2-17959, and International Publication WO98. / 29391 publication.
  • 2- (unsubstituted or substituted) benzoylamino-6- (unsubstituted or substituted) phenoxypyridine derivative of the present invention is not described in the literature and is a novel compound.
  • herbicides that can reduce the abundance in the environment, show low herbicidal efficacy at low doses, herbicides that show selectivity between crops and weeds regardless of changes in environmental conditions, after double cropping There is a need to provide herbicides that do not cause harm to crops.
  • the present invention has been made in view of the above circumstances, and an object of the present invention is to provide a novel compound exhibiting an excellent herbicidal effect, a method for producing the same, and a novel herbicide containing the compound as an active ingredient. It is in.
  • the present inventors have conducted various studies to find a novel pyridine derivative which is industrially useful, and as a result, it is a novel compound which is not described in the above literature.
  • the inventors have found that a 2- (unsubstituted or substituted) benzoylamino-6- (unsubstituted or substituted) phenoxypyridine derivative has high herbicidal properties, and have completed the present invention.
  • a first gist of the present invention resides in a 2- (unsubstituted or substituted) benzoylamino-6- (unsubstituted or substituted) phenoxypyridine derivative represented by the general formula (I).
  • X is a halogen atom, C ⁇ ⁇ alkyl group, mouth alkyl group, (:.) ⁇ Alkoxy, C 4 haloalkoxy group, ( ⁇ ⁇ ⁇ 3 4 alkyl Chiomoto, C i to Ji 4 haloalkylthio group, a nitro group, a Shiano group, m.
  • Y is a halogen atom represents an integer of 0 - 5, C!
  • CA alkyl group ( ⁇ Ji ⁇ port alkyl groups, C] -C 4 alkoxy group, CCA haloalkoxy group, Ci ⁇ C 4 alkylthio groups, C ⁇ Ji, Roarukiruchio group, ⁇ C ⁇ alkylamino groups, C] - (- 4 dialkylamino group, a nitro group, a Shiano group, n represents an integer of 0 to 3 are shown.
  • Z represents a halogen atom, C!
  • m, n, and p are 2 or more, X, Y, and ⁇ are the same or different. And it may be.
  • a second gist of the present invention is to provide a 2-amino-6- (unsubstituted or substituted) phenoxypyridine derivative represented by the general formula ( ⁇ ) as represented by the following reaction formula: 2- (unsubstituted or substituted) benzol represented by the general formula (I) characterized by reacting with (unsubstituted or substituted) benzoyl halide represented by (III) Ylamino-6- (unsubstituted or substituted) phenoxypyridine derivative.
  • X is a halogen atom, cc ⁇ alkyl group, c:!!] - (4 cutting edge alkyl group, C C alkoxy group, C 4 cutting edge alkoxy group, Ji-Ji alkyl Chiomoto, C ⁇ 4 haloalkylthio group, a nitro group, a Shiano group, m is an integer of 0 - 5.
  • Y is a halogen atom, C] -C 4 alkyl group, ( ⁇ - ( ⁇ port alkyl group,
  • a third gist of the present invention is that of general formula (I) 2 — (unsubstituted or substituted) benzoylamino-6- (unsubstituted or substituted) phenoxypyridine derivative Herbicide characterized by containing as an active ingredient.
  • Halogen atom for X chlorine atom, bromine atom, fluorine atom, the -C 4 alkyl group, a methyl group, Echiru group, (! ⁇ Ji, as the mouth alkyl group, triflate Ruo b methyl group, C to ( 4 alkoxy groups include methoxy groups and ethoxy groups, etc .; C to C 4 halo alkoxy groups include difluoromethoxy groups and trifluoromethoxy groups; C! To 4 alkylthio groups; main Chiruchio group, etc. Echiruchio group, the C ⁇ 4 haloalkylthio group, etc. Application Benefits full O b methyl thio group, further, a nitro group, Shiano group forces? like.
  • X in the above definition includes a halogen atom (a chlorine atom and a bromine atom), a methyl group, a difluoromethyoxy group, a trifluoromethyl group, a trifluoromethoxy group and the like, and among them, a trifluoromethyl group is particularly preferable. preferable.
  • halogen atom in Y examples include a chlorine atom, a bromine atom, a fluorine atom, and the like.
  • the C! C ⁇ alkyl group, a methyl group, Echiru group, ( ⁇ . ⁇ , As the Roaruki group, triflate Ruo b methyl group, C ⁇ -c 4 The alkoxy group main butoxy group, an ethoxy group, etc.
  • More preferable Y in the above definition includes a chlorine atom, a methyl group, a methoxy group, a methylthio group, a dimethylamino group, a methylamino group and the like, and among them, the methoxy group S is particularly preferable.
  • the range of ⁇ is usually from 0 to 3, and more preferably from 0 to 1. Among them, those having a substituent at the 4-position on the pyridine ring are particularly preferred.
  • the halogen atom in ⁇ is a chlorine atom, a bromine atom, a fluorine atom, etc.
  • the C alkyl group is a methyl group, an ethyl group, etc. (: :- ⁇ , the loalkyl group is a trifluoromethyl group, etc.
  • the i-C 4 alkoxy group include a methoxy group and an ethoxy group, and the like
  • examples of the C ⁇ -(: 4- halo alkoxy group include a trifluoromethoxy group and the like, and further, a nitro group and a cyano group.
  • Z in the above definition includes a chlorine atom, a fluorine atom, a bromine atom, a methyl group, a trifluoromethyl group, a methoxy group and the like.
  • Halogen atoms such as chlorine atom, fluorine atom and bromine atom are particularly preferred.
  • the range of p is usually from 0 to 5, and more preferably from 0 to 2.
  • X represents a substituent on the phenoxy ring.
  • the number preceding the substituent indicates the bonding position. For example, 3-CF 3 in compound (1-1) indicates that CF 3 is bonded to the third carbon atom on the phenoxy ring.
  • Y represents a substituent on the pyridine ring.
  • the number before the substituent indicates the bonding position.
  • 4- ⁇ CH 3 in compound number (1-4) indicates that ⁇ CH 3 is bonded to the carbon atom at the 4-position on the pyridin ring.
  • Z represents a substituent on the benzoyl ring.
  • the number preceding the substituent indicates the bonding position.
  • 2,4-Cl 2 in compound (1-17) indicates that the chlorine atom is bonded to the carbon atom at the 2- and 4-positions on the benzoyl ring.
  • aromatic hydrocarbons such as benzene, toluene, xylene, and methylnaphthalene
  • aliphatic hydrocarbons such as petroleum ether, pentane, hexane, heptane, methylcyclohexane, methylene chloride, and chloroform
  • Halogenated hydrocarbons such as oral form, carbon tetrachloride, and chlorobenzene
  • amides such as dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, getyl ether, dimethyloxetane, diisopropyl ether, Ethers such as tetrahydrofuran, diglyme, and dioxane
  • alcohols such as methanol and ethanol.
  • solvents used include water, carbon disulfide, acetonitrile, ethyl acetate, pyridine, dimethyl sulfoxide, hexamethylphosphoramide, and the like. These solvents may be used as a mixture of two or more kinds.
  • the individual reaction steps of the process according to the invention are advantageously carried out in a solvent or a mixture of solvents.
  • a solvent composition composed of solvents that do not form a uniform layer with each other can also be used.
  • a phase transfer catalyst to the reaction system for example, the force? Is suitable to add a fourth ammonium two ⁇ beam salts or Kuraun'eteru customary.
  • This compound (I) is obtained by converting a 2-amino-6- (unsubstituted or substituted) phenoxypyridine derivative represented by the following general formula (II) into a compound represented by the following general formula (III) (unsubstituted or substituted). Substitution) Obtained by reacting with benzoyl chloride. This is represented by the following reaction formula.
  • the reaction is usually carried out by mixing compound ( ⁇ ) and compound ( ⁇ ) in a solvent. It is very effective to use the following bases as catalysts.
  • the amount of compound (III) to be used is generally 0.5 to 5 moles, preferably 0.8 to 1.5 moles, relative to compound (II).
  • the reaction temperature is usually 0 to 200 ° C, preferably 10 to 150 ° C.
  • the reaction time is a few minutes to a few days.
  • tertiary amines, dialkylamido Organic bases of noanilines and pyridines for example, triethylamine, N, ⁇ ,, ′, N′-tetramethylethylenediamine (TMEDA), ⁇ , ⁇ -dimethylaniline, ⁇ , ⁇ ⁇ -jetylaniline, pyridine , 4-dimethylaminopyridine
  • inorganic bases such as alkali metal and alkaline earth metal hydroxides, carbonates and bicarbonates, for example, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, water Examples thereof include sodium oxide, potassium hydroxide, and calcium hydroxide.
  • carboxylic acid halide As the compound ( ⁇ ), a commercially available carboxylic acid halide can be used.
  • Carboxylic acid halides are derived, for example, by deriving (unsubstituted or substituted) benzoic acid compounds from carboxylic acids using halogenating reagents such as thionyl chloride, phosphoryl chloride, phosphorus pentachloride, phosphorus trichloride, and phosphoryl bromide.
  • halogenating reagents such as thionyl chloride, phosphoryl chloride, phosphorus pentachloride, phosphorus trichloride, and phosphoryl bromide.
  • Compounds that can be manufactured using existing technologies, such as the above, can be used.
  • Compound ( ⁇ ) can be produced by the following method. That is, the compound represented by the general formula (II) is easily converted to a compound represented by the general formula (II) by subjecting the compound represented by the general formula (V) to Lossen rearrangement in the presence of a base and subjecting the resulting isocyanate compound (IV) to water addition and decarboxylation. Can be obtained. These are shown by the following reaction formulas.
  • the production method for obtaining the compound ( ⁇ ) is shown below.
  • the reaction for obtaining compound (IV) will be described.
  • the reaction is usually carried out by mixing compound (V) in an organic solvent and using a base as a catalyst.
  • the amount of the base to be used is generally 1 to 2 moles, preferably 1 to 1.5 moles, per 1 mole of Compound (V).
  • the reaction temperature is 0 to 200 ° C, preferably 10 to 150 ° C.
  • the reaction time is several minutes to several days.
  • examples of the base used include hydrides, hydroxides, carbonates and bicarbonates of alkali metals and alkaline earth metals, such as sodium hydride, examples thereof include lithium hydride, sodium hydroxide, lithium hydroxide, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, and potassium carbonate. Particularly preferred bases are sodium hydride and potassium carbonate.
  • a production method for obtaining the compound (II) by adding water and decarboxylating the compound (IV) will be described below. First, the reaction is usually performed in a mixed solvent obtained by mixing water with the reaction solution used in the reaction for obtaining the compound (IV) without isolating the compound (IV). These do not have to form a uniform layer with each other.
  • the reaction can proceed sufficiently without adding a catalyst, and of course, an acid or a base may be added as a catalyst.
  • an acid or a base may be added as a catalyst.
  • an inorganic acid such as hydrochloric acid, hydrobromic acid or sulfuric acid is usually used as the catalyst.
  • an alkali metal base such as sodium hydroxide or potassium hydroxide is usually used as the catalyst.
  • the hydrolysis temperature is usually in the range of 0 to the reflux point.
  • the reaction time is several minutes to several hours.
  • the compound of the formula (V) can be easily obtained by mixing the compound of the formula (VI) with hydroxyamine. These are represented by the following reaction formulas.
  • W 1 represents a halogen atom or a CC ⁇ lower alkoxy group.
  • Compound (VII) can be produced, for example, by the method described in International Patent Publication No. 98/29391.
  • This compound (I) can be used as it is as a herbicide. Usually, it is formulated into various forms such as powders, wettable powders, granules and emulsions together with formulation aids. In this case, one or more of the present compounds in the formulation (I), usually 0.:! ⁇ 95 wt%, preferably from 0.5 to 90 wt%, more preferably is 2 to 70 weight 0/0 containing organic You.
  • Examples of carriers, diluents, and surfactants used as formulation aids include solid carriers, such as talc, kaolin, bentonite, diatomaceous earth, white power—bon, clay, and the like .
  • Examples of the diluent include water, xylene, toluene, benzene, cyclohexane, cyclohexanone, dimethyl sulfoxide, dimethylformamide, and alcohol. It is better to use different surfactants depending on their effects.
  • emulsifiers generally include polyoxyethylene alkylaryl ether, polyoxyethylene alkyl ether, polyoxyethylene sorbitan monolaurate, and the like.
  • Dispersants include lignin sulfonate, Dibutyl naphthalene sulfonate No.
  • the wetting agent generally include an alkyl sulfonate and an alkylphenyl sulfonate.
  • the concentration of this compound (I) is usually in the range of 0.001 to 1.0%.
  • the amount of the present compound (I) to be used is usually 0.001 to: L0 kg, preferably 0.01 to 5 kg per lha. Since the concentration and amount of use differ depending on the dosage form, time of use, method of use, place of use, target crop, etc., it is possible to increase or decrease without being limited to the above range. Further, the present compound (I) can be used in combination with other active ingredients such as fungicides, insecticides, acaricides, herbicides and the like.
  • 2-Amino-4-methoxy-6-[(3-trifluoromethyl) phenoxy] pyridine (0.20 g, 0.00070 mol) was dissolved in benzene (about 20 ml), and 3-bromobenzoyl chloride (0.17 g, 0.00070 XI. Lmol) and triethylamine (0.084 g, 0.00070 XI.2 mol) were added, and the mixture was refluxed for about 2 hours. After cooling, ethyl acetate was added to the reaction mixture, followed by washing with water.
  • 2-Amino-4-methoxy-6 _ [(3-trifluoromethyl) phenoxy] pyridine (0.20 g, 0.00070 mol) is dissolved in benzene (about 20 ml), and 4-chlorobenzoyl chloride (0.135 g) is dissolved.
  • benzene about 20 ml
  • 4-chlorobenzoyl chloride 0.135 g
  • triethylamine 0.084 g, 0.00070 XI.2 mol
  • Test example 1 (Test for herbicidal effect by foliage and soil treatment):
  • Herbicidal rate is 20% or more and less than 40%
  • Herbicidal rate is 80% or more

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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)
  • Pyridine Compounds (AREA)

Abstract

Cette invention concerne des dérivés de 2-benzoylamino-6-phénoxypyridine représentés par la formule générale (I), un procédé de préparation de ces dérivés ainsi que des herbicides renfermant ces dérivés comme principe actif.
PCT/JP2000/004115 1999-06-29 2000-06-23 Derives de pyridine 2-(eventuellement substituee benzoylamino)-6-(eventuellement substituee phenoxy), preparation de ces derives et herbicides Ceased WO2001000580A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2000254293A AU2000254293A1 (en) 1999-06-29 2000-06-23 2-(optionally substituted benzoylamino)-6-(optionally substituted phenoxy)pyridine derivatives, process for the preparation thereof and herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP11/183455 1999-06-29
JP18345599 1999-06-29

Publications (1)

Publication Number Publication Date
WO2001000580A1 true WO2001000580A1 (fr) 2001-01-04

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PCT/JP2000/004115 Ceased WO2001000580A1 (fr) 1999-06-29 2000-06-23 Derives de pyridine 2-(eventuellement substituee benzoylamino)-6-(eventuellement substituee phenoxy), preparation de ces derives et herbicides

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WO (1) WO2001000580A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10130397A1 (de) * 2001-06-23 2003-01-09 Bayer Cropscience Gmbh Herbizide substituierte Pyridine, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbzide und Pflanzenwachstumsregulatoren
WO2005007627A1 (fr) * 2003-07-18 2005-01-27 Nihon Nohyaku Co., Ltd. Derive de phenylpyridine, produit intermediaire correspondant, et herbicide contenant ledit derive de phenylpyridine en tant qu'ingredient actif
CN113773264A (zh) * 2021-08-11 2021-12-10 池州飞昊达化工有限公司 一种应用于除草剂的嘧啶酰胺化合物及制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0488474A1 (fr) * 1990-11-28 1992-06-03 Shell Internationale Researchmaatschappij B.V. Dérivés herbicides de carboxamide
JPH04330059A (ja) * 1990-11-27 1992-11-18 Tosoh Corp カーバメート誘導体及びそれを有効成分とする除草剤
WO1998029391A1 (fr) * 1996-12-26 1998-07-09 Kureha Kagaku Kogyo Kabushiki Kaisha Acides phenoxypicoliniques non substitues ou substitues en position 6, procede de preparation desdits acides et germicides agricoles/horticoles les contenant

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04330059A (ja) * 1990-11-27 1992-11-18 Tosoh Corp カーバメート誘導体及びそれを有効成分とする除草剤
EP0488474A1 (fr) * 1990-11-28 1992-06-03 Shell Internationale Researchmaatschappij B.V. Dérivés herbicides de carboxamide
WO1998029391A1 (fr) * 1996-12-26 1998-07-09 Kureha Kagaku Kogyo Kabushiki Kaisha Acides phenoxypicoliniques non substitues ou substitues en position 6, procede de preparation desdits acides et germicides agricoles/horticoles les contenant

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10130397A1 (de) * 2001-06-23 2003-01-09 Bayer Cropscience Gmbh Herbizide substituierte Pyridine, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbzide und Pflanzenwachstumsregulatoren
WO2003000679A3 (fr) * 2001-06-23 2003-04-24 Bayer Cropscience Gmbh Pyridine substituee herbicide, son procede de fabrication et son utilisation comme herbicide et regulateur de croissance des plantes
US6794336B2 (en) 2001-06-23 2004-09-21 Aventis Crop Science Gmbh Herbicidal substituted pyridines, their preparation, and their use as herbicides and plant growth regulators
RU2304141C2 (ru) * 2001-06-23 2007-08-10 Байер Кропсайенс Гмбх Производные пиридина и гербицидное средство на их основе
WO2005007627A1 (fr) * 2003-07-18 2005-01-27 Nihon Nohyaku Co., Ltd. Derive de phenylpyridine, produit intermediaire correspondant, et herbicide contenant ledit derive de phenylpyridine en tant qu'ingredient actif
CN113773264A (zh) * 2021-08-11 2021-12-10 池州飞昊达化工有限公司 一种应用于除草剂的嘧啶酰胺化合物及制备方法

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122 Ep: pct application non-entry in european phase