WO2001014303A1 - Composes de tricetone, leur procede de production et herbicides les contenant - Google Patents

Composes de tricetone, leur procede de production et herbicides les contenant Download PDF

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Publication number
WO2001014303A1
WO2001014303A1 PCT/JP2000/005565 JP0005565W WO0114303A1 WO 2001014303 A1 WO2001014303 A1 WO 2001014303A1 JP 0005565 W JP0005565 W JP 0005565W WO 0114303 A1 WO0114303 A1 WO 0114303A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
compound
salt
reaction
atom
Prior art date
Application number
PCT/JP2000/005565
Other languages
English (en)
Japanese (ja)
Inventor
Yuji Nakamura
Christopher John Palmer
Hiroshi Kikugawa
Makiko Sano
Original Assignee
Ishihara Sangyo Kaisha, 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.)
Filing date
Publication date
Application filed by Ishihara Sangyo Kaisha, Ltd. filed Critical Ishihara Sangyo Kaisha, Ltd.
Priority to AU65971/00A priority Critical patent/AU6597100A/en
Publication of WO2001014303A1 publication Critical patent/WO2001014303A1/fr

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Classifications

    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
    • C07D309/06—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the solvent may be any solvent as long as it is inert to the reaction, for example, aromatic hydrocarbons such as benzene, toluene, xylene, and benzene; carbon tetrachloride, methyl chloride, and chloroform.
  • aromatic hydrocarbons such as benzene, toluene, xylene, and benzene
  • carbon tetrachloride methyl chloride, and chloroform.
  • Aliphatic hydrocarbons such as dichloromethane, dichloroethane, trichloroethane, hexane and cyclohexane
  • esters such as methyl acetate and ethyl acetate
  • alcohols such as methanol, ethanol, propanol and tert-butyl alcohol.
  • One or more kinds are appropriately selected from organic acids such as acetic acid and propionic acid; water and the like.
  • the base examples include alkali metals such as sodium and potassium; alkali metal alcoholates such as sodium methylate, sodium ethylate and potassium tertiary butylate; carbonates such as sodium carbonate and potassium carbonate; sodium bicarbonate Bicarbonates such as potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; monomethylamine, dimethylamine, triethylamine
  • pyridines such as pyridine and 4-dimethylaminopyridine are appropriately selected.
  • the base is used in an amount of 1 to 3 moles, preferably 1 to 1.5 moles, based on the compound of the formula (IV).
  • Aliphatic hydrocarbons such as REM, dichloromethane, dichloroethane, trichloroethane, hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran and getyl ether; esters such as methyl acetate and ethyl acetate; One or two or more nitriles such as acetonitrile, propionitrile and acrylonitrile; and one or more from ketones such as acetone and methylethylketone are appropriately selected.
  • REM dichloromethane
  • dichloroethane dichloroethane
  • trichloroethane hexane and cyclohexane
  • ethers such as dioxane, tetrahydrofuran and getyl ether
  • esters such as methyl acetate and ethyl acetate
  • One or two or more nitriles such as
  • Solvents such as water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methylisobutylketone, benzene, cyclohexane, dimethylsulfoxide, dimethylformamide, N-stil-2-pyrrolidone, alcohol, etc .; Fatty acid salt, benzoate, alkyl sulfosuccinate, dialkyl sulfosuccinate, polycarboxylate, alkyl sulfate, alkyl sulfate, alkyl aryl sulfate, alkyl diglycol ether sulfate, a Cholesulfate, alkyl sulfonate, alkyl aryl sulfonate, aryl sulfonate, lignin sulfonate, alkyl diphenyl ether disulfonate, polystyrene sulfonate,
  • the mixing ratio of the compound of the present invention and the active ingredient compound of other herbicides cannot be specified unconditionally due to differences in weather conditions, soil conditions, formulation of the drug, application time, application method, etc.
  • the other herbicide contains 0.001 to 10,000 parts by weight, preferably 0.01 to 1,000 parts by weight of the active ingredient compound per one kind.
  • the appropriate amount of application is 0.1 to 1000 g, preferably 0.2 to 5000 g, as the total amount of the active ingredient compound per hectare.
  • the present invention also includes a method for controlling harmful weeds by applying such a mixed herbicidal composition.
  • active ingredient compounds of other herbicides include the following (generic names; including those for which some applications have been filed), but even if not specified, salts, alkyl esters, etc. If present, they are of course included.
  • Urea compounds such as diuron, diuron, 1 inuron, isoproturon, metob en zuron, simazine, atrazine , Atraton (atrat one), simetryn (simetryn), promethrin (prome tryn), dimethamethrin (dim ime tham etr yn), metrivudine (me tri bu zi ne), terbutyrazine (ter bu t hv lazine) ), Cyanan (c yan azi ne), Triamone (ame tryn), sibutrin (cybutrin), triadifram (triazif 1 am), propazine (propazine), triazines such as bromacil (broma ci 1), renacil (1 enaci 1).
  • perillacile propanil (propani 1)
  • anilide such as cypromid (cypromid)
  • carbamate such as sphenp (swep), phenmedipham (phe nme diph am)
  • bromoxynil bromox) hydroxy benzonitrile, such as yn i 1), bromooxyn i 1 -octanoate, ioxy nil (io xy ni 1), other py ridates, bentazon ), Amicarbazone (amica rb az on e), etc., which are said to exhibit herbicidal efficacy by inhibiting photosynthesis in plants.
  • Quaternary ammonium such as paraquat and diguat, which are themselves considered as free radicals in plants and produce active oxygen to exhibit rapid herbicidal efficacy. Salt-based.
  • diclohop-methyl (dic 1 of op—methy 1), pyriphenop-nadium salt (pyri henop-sod i um), fJreadihop-butyl (f1 uazifo-butyl), haloxyfop-methyl (Ha 1 oxyfop-met hyl), quizalofop-ethyl (qu izalof op-ethy 1), cyhalofop-butyl (cyhalofop-butyl), fenoki sappropetyl (fe nox aprop-et hyl)
  • arijireokishifuenoxypropionic acid aroxydim sodium salt (a1loxydim-sodium), clesodymium (clet hod im), sethoxydim (set hoxydim), trarilecoxime (tralk oxyd im), buttox oxime (bu tr
  • Dinitroaniline such as trifluralin (trif 1 ura 1 in), oryzalin (oryza 1 in), nitralin (nitra 1 in), pendimehulin (pendimetha 1 in), ethalfluralin (ethalf 1 ura 1 in), and ami Organophosphorus compounds such as prophos-methyl (ami profos-methyl), bushu miphos (butamifos), anilofos (an ilofos), piperophos (pi pe ro phos), and chlorprofam (chlorpro) ph am), phenyl carbamates such as barban, daimuron, cumyluron, cumylamine such as bromobutide, and other ashrams (asu 1 am ), Dithiopyr (dithiopyr), thiazopyr (thiazo pyr), which are said to exhibit herbicidal efficacy by inhibiting cell mitosis in plants.
  • Trifluralin trif 1 ura
  • EPTC butyrate (buty 1 ate), molinet (mo 1 inate), dimepirate (dime pi pe rate), fluazolate (fluazolate), esprocalp (esproc arb), thiobencarb ( thi ob en carb), pyributicarb (py ri bu ticarb), thiocarbamate like triallate (triallate), araclo (a 1 ach 1 or), buta crawl (butachlor), pretilachlore, pretilachlor ), Methracloirille (me to 1 ach 1 or), S—metolachlor (S—me tolachlor), tenylchlor (t heny lchlor), dimethenamide dime the nami d), acetochlor (acetochlor), Chloroacetamides such as propachlor, other ethobe nzanide, mefuena (Me fena cet), refenaset (
  • R is alkyl
  • R 2 is halogen, haloalkyl, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, octaalkylsulfonyl, dialkylaminosulfonyl, di (octaalkyl) aminosulfonyl
  • R is alkyl
  • R 2 is halogen, alkylthio, alkylsulfinyl, alkylsulfonyl or nitro
  • A is a 5- or 6-membered saturated heterocyclic group containing 1-2 oxygen atoms (The heterocyclic group may be substituted with alkyl).
  • a wettable powder or emulsion prepared according to the usual formulation method of the compound of the present invention is weighed so as to have a predetermined amount of the active ingredient, and diluted with 500 liters of water per 1 ct. did. Further, 0.1% by volume of an agricultural spreading agent was added to the diluted solution, and foliage treatment was performed with a small spray.
  • a 1 / 1,000,000 hectare pot was filled with paddy field soil, and seeds of Nobie and Louisiana were sown and lightly covered with soil. After that, they were allowed to stand still in a greenhouse at a waterlogging depth of 0.5 to 1 cm, and the tuber of Perica was planted the next day or two days later. After that, the flooding depth was kept at 3 to 4 cm, and when the Nobie and Hoyurui reached the 0.5-leaf stage and Perica reached the primary-leaf stage, the compound of the present invention was hydrated according to the usual formulation method. A water-diluted solution of the agent or the emulsion was uniformly dropped by a pipe so as to have a predetermined amount of the active ingredient.
  • Paddy soil is packed in a 1,100,000 hectare pot, paddy is padded, the flooding depth is set to 3 to 4 cm, and rice of the second leaf stage (cultivar: Nipponbare) is transplanted the next day. cm.
  • the compound of the present invention was treated in the same manner as described above.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (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)

Abstract

L'invention concerne des composés de tricétone ou leurs sels représentés par la formule générale (I), dans laquelle W représente oxygène ou soufre, y est un nombre entier compris entre 1 et 6, A représente un hétérocycle saturé à 5 ou 6 chaînons éventuellement alkylé renfermant un ou deux atomes d'oxygène ou de soufre ou un dialkoxyméthyle, R1 représente (halo)alkyle, (halo)alcoxy,(halo)alkylthio,(halo)alkylsulfinyle, (halo)alkylsulfonyle, nitro ou cyano, R2 représente un des membres tels que définis en R1, halogène ou di((halo)alkyl)aminosulfonyle, R3, R4, R6, et R8 représentent chaque hydrogène ou alkyle, R5 représente hydrogène alkyle ou cycloalkyle ou R5 et R8 peuvent former ensemble un anneau de carbone saturé à 3 à 6 chaînons ou R5 et R6 peuvent former ensemble une cétone.
PCT/JP2000/005565 1999-08-19 2000-08-18 Composes de tricetone, leur procede de production et herbicides les contenant WO2001014303A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU65971/00A AU6597100A (en) 1999-08-19 2000-08-18 Triketone compounds, process for producing the same and herbicides containing the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP23257199 1999-08-19
JP11/232571 1999-08-19

Publications (1)

Publication Number Publication Date
WO2001014303A1 true WO2001014303A1 (fr) 2001-03-01

Family

ID=16941440

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2000/005565 WO2001014303A1 (fr) 1999-08-19 2000-08-18 Composes de tricetone, leur procede de production et herbicides les contenant

Country Status (2)

Country Link
AU (1) AU6597100A (fr)
WO (1) WO2001014303A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001053275A2 (fr) * 2000-01-17 2001-07-26 Bayer Aktiengesellschaft Arylcetones substituees
WO2005118530A1 (fr) * 2004-06-03 2005-12-15 Ishihara Sangyo Kaisha, Ltd. Composés de triketone, leur méthode de producion et celle d’herbicides les contenant
JP2006016389A (ja) * 2004-06-03 2006-01-19 Ishihara Sangyo Kaisha Ltd トリケトン系化合物、それらの製造方法及びそれらを含有する除草剤
JP2007507444A (ja) * 2003-09-29 2007-03-29 イサグロ リチェルカ ソシエタ ア レスポンサビリタ リミタータ 除草性活性を有する１，３−ジオンの誘導体
CN101742905A (zh) * 2007-07-13 2010-06-16 石原产业株式会社 除草性组合物
JP2010189299A (ja) * 2009-02-17 2010-09-02 Hokko Chem Ind Co Ltd 有効成分の安定化された農薬粒剤
KR101225441B1 (ko) * 2004-06-03 2013-01-22 이시하라 산교 가부시끼가이샤 트리케톤계 화합물, 이들의 제조 방법 및 이들을 함유하는제초제

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06271562A (ja) * 1993-03-23 1994-09-27 Hokko Chem Ind Co Ltd シクロヘキサンジオン誘導体および除草剤
JPH0769963A (ja) * 1993-08-30 1995-03-14 Hokko Chem Ind Co Ltd シクロヘキサンジオン誘導体および除草剤

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06271562A (ja) * 1993-03-23 1994-09-27 Hokko Chem Ind Co Ltd シクロヘキサンジオン誘導体および除草剤
JPH0769963A (ja) * 1993-08-30 1995-03-14 Hokko Chem Ind Co Ltd シクロヘキサンジオン誘導体および除草剤

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001053275A2 (fr) * 2000-01-17 2001-07-26 Bayer Aktiengesellschaft Arylcetones substituees
WO2001053275A3 (fr) * 2000-01-17 2003-04-17 Bayer Ag Arylcetones substituees
US6864219B2 (en) 2000-01-17 2005-03-08 Bayer Aktiengesellschaft Substituted aryl ketones
JP2007507444A (ja) * 2003-09-29 2007-03-29 イサグロ リチェルカ ソシエタ ア レスポンサビリタ リミタータ 除草性活性を有する１，３−ジオンの誘導体
WO2005118530A1 (fr) * 2004-06-03 2005-12-15 Ishihara Sangyo Kaisha, Ltd. Composés de triketone, leur méthode de producion et celle d’herbicides les contenant
JP2006016389A (ja) * 2004-06-03 2006-01-19 Ishihara Sangyo Kaisha Ltd トリケトン系化合物、それらの製造方法及びそれらを含有する除草剤
KR101225441B1 (ko) * 2004-06-03 2013-01-22 이시하라 산교 가부시끼가이샤 트리케톤계 화합물, 이들의 제조 방법 및 이들을 함유하는제초제
CN101742905A (zh) * 2007-07-13 2010-06-16 石原产业株式会社 除草性组合物
US8435928B2 (en) 2007-07-13 2013-05-07 Ishihara Sangyo Kaisha, Ltd. Herbicidal composition
CN105941398A (zh) * 2007-07-13 2016-09-21 石原产业株式会社 除草性组合物
CN105941398B (zh) * 2007-07-13 2019-07-26 石原产业株式会社 除草性组合物
JP2010189299A (ja) * 2009-02-17 2010-09-02 Hokko Chem Ind Co Ltd 有効成分の安定化された農薬粒剤

Also Published As

Publication number Publication date
AU6597100A (en) 2001-03-19

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