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    • 1. 发明授权
    • Diphenylethers having herbicidal properties
    • 具有除草性能的二苯醚
    • US3849503A
    • 1974-11-19
    • US31715572
    • 1972-12-21
    • ISHIHARA MINING & CHEMICAL CO
    • YOKOMICHI IKIMURA FTAKAGI HNASU RTAKAHASHI RTOKI TSHIGEHARA INISHIYAMA RSOMEYA S
    • C07C6/12C07C7/13C07C205/38C07C43/20
    • C07C6/126C07C7/13C07C201/12C07C15/02C07C205/38
    • 1. A PROCESS FOR PRODUCING A DIPHENYLETHER HAVING THE GENERAL FORMULA:

      Y-(3-X,Z-1,4-PHENYLENE)-O-(3-(R-O-)-1,4-PHENYLENE)-NO2

      WHEREIN X REPRESENTS A HALOGEN ATOM OR A METHYL RADICAL IN THE 2-POSITION; Y REPRESENTS A HALOGEN ATOM OR AN ALKYL RADICAL HAVING UP TO 3 CARBON ATOMS IN THE 4-POSITION; Z REPRESENTS HYDROGEN OR HALOGEN IN THE 5- AND 6POSITIONS, WHEREIN BOTH THE 5- AND 6-POSITIONS MAY BE HYDROGEN, BUT ONLY ONE OF THE 5- OR 6-POSITIONS MAY BE HALOGEN; AND R REPRESENTS A SATURATED OR AN UNSATURATED HYDROCARBON HAVING UP TO 3 CARBON ATOMS, METHOXYETHYL OR AN ETHOXYETHYL RADICAL, WHICH COMPRISES REACTING IN THE PRESENCE OF AN ALKALI METHYL HYDROXIDE OR CARBONATE A 2,4-DIHALONITROBENZENE HAVING THE GENERAL FORMULA:

      1-(O2N-),2,4-DI(HAL-)-BENZENE

      WHEREIN HAL IS A HALOGEN ATOM, WITH A SUBSTITUTED PHENOL HAVING THE GENERAL FORMULA:

      Y-(3-X,Z-1,4-PHENYLENE)-O-(4-(O2N-)-1,3-PHENYLENE)-O-

      2-X,4-Y,Z-PHENOL WHEREIN THE MOLAR RATIO OF THE PHENOL TO THE 2,4-DIHALONITROBENZENE IS AT LEAST 2:1, AT A TEMPERATURE OF FROM 130* C. TO 160* C. TO PRODUCE A 2,4-BIS(SUBSTITUTED PHENOXY) NITRO BENZENE HAVING THE GENERAL FORMULA: 1-(O2N-),2,4-BIS((2-X,4-Y,Z-PHENYL)-O-)BENZENE THEN REACTING SAID 2,4-BIS(SUBSTITUTED PHENOXY) NITROBENZENE (IV) IN THE PRESENCE OF AN ALKALI METAL HYDROXIDE WITH AN ALCOHOL OF THE FORMULA ROH WHEREIN R IS AS DEFINED ABOVE AT A TEMPERATURE OF 20-100* C. TO PRODUCE SAID DIPHENYLETHER (I) AND A SUBSTITUTED PHENOL (III) AND THEREAFTER ISOLATING SAID DIPHENYLETHER (I).
    • 3. 发明专利
    • SE7511634L
    • 1976-04-18
    • SE7511634
    • 1975-10-16
    • ISHIHARA MINING & CHEMICAL CO
    • TAKAHASHI RFUJIKAWA KYOKOMICHI ITSUJII YSAKASHITA N
    • A01N39/02A01P13/02C07D213/63C07D213/64C07D213/643C07D213/75C07D521/00A01N43/40
    • 1491274 α - [4 - (5 - mono-substituted or 3,5 - di - substituted - pyridyl - 2 - oxy)phenoxy]- alkanecarboxylic acid derivatives ISHIHARA SANGYO KAISHA Ltd 10 Oct 1975 [17 Oct 1974 13 March 1975] 41560/75 Heading C2C Novel α - [4 - (5 - mono-substituted or 3,5 - di - substituted - pyridyl - 2 - oxy)- phenoxy] - alkanecarboxylic acid derivatives of the formula wherein X is a halogen atom; Y is a hydrogen atom, a halogen atom or a methyl group; R is a hydrogen atom or a straight or branched chain (C 1 -C 6 ) alkyl group; and R 1 is a hydroxy group; a (C 1 -C 9 ) alkoxy group in which the alkyl moiety thereof may have a straight or a branched chain and may be substituted with one or more of a halogen atom or a hydroxy group; an -(OC 2 H 4 ) n -O- (C 1 -C 4 ) alkyl group in which the alkyl moiety thereof may have a straight or a branched chain and n is 1, 2, 3, 4 or 5; a (C 1 -C 4 ) alkylthio group in which the alkyl moiety thereof may have a straight or a branched chain; a (C 2 -C 4 ) alkenyloxy group; a cyclohexyloxy group in which the cyclohexyl moiety thereof may be substituted with one or more of a halogen atom or a methyl group; a phenoxy group in which the aryl moiety thereof may be substituted with one or more of a halogen atom or a methyl group; a phenylthio group in which the aryl moiety thereof may be substituted with one or more of a halogen atom or a methyl group; a benzyloxy group in which the aryl moiety thereof may be substituted with one or more of a halogen atom or a methyl group; an amino group which may be substituted with one or more of a (C 1 -C 4 ) alkyl group in which the alkyl moiety thereof may have a straight or a branched chain and may be substituted with a hydroxy group; a mono-(C 1 -C 4 ) alkylamino group in which the alkyl moiety thereof may have a straight or a branched chain and is substituted with a -COOR 4 group in which R 4 is a hydrogen atom, a cation or a straight or branched chain (C 1 -C 4 ) alkyl group; an anilino group in which the aryl moiety thereof may be substituted with one or more of a halogen atom or a methyl group; a benzylamino group; an amino group substituted with a heterocyclic group in which the heterocyclic moiety thereof may be substituted with one or more of a halogen atom or a methyl group; a morpholino group; a piperidino group; an -OM group where M is a cation; or a halogen atom, are prepared by reacting a substituted pyridine of the formula with a substituted phenol of the formula wherein Z is a hydroxy group; a (C 1 -C 5 ) alkoxy group or a group of the formula wherein R 3 is a hydroxy group; a (C 1 -C 9 ) alkoxy group or an amino group, in the presence of an alkaline material in an amount of from 1 to 1À2 moles per mole of compound III at a temperature of at least 50‹ C. for 1 to 20 hours to give a substituted pyridyl phenyl ether of the formula and, when Z is other than optionally dealkylating the compound of Formula IV and reacting this compound with an α-haloalkanecarboxylic acid or a derivative thereof having the formula in the presence of an alkaline material in an amount of from 1 to 1À2 moles per mole of compound IV to give a compound of the formula and optionally converting the R 3 moiety into R 1 . The novel compounds possess herbicidal properties.