• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    The invention relates to the production of ethers, in particular the substituted benzyl fluxes of a common f; CK, -CA (.) CH, 2.-Х-В, where a) B group -CH2- (oVRi E, -H; OCglis F; A E ,,. C1, F, Br, allyl-OXI-; - lkl. l - alkoxy - group or substituted by 1 torus; C, - or C-alkoxy group or / O / R means 1,3-benzodioxolane at R H, F; X is oxygen or sulfur, and XS, R, ethoxy group and B -SH-GZuOSbN. ;; N b) B -CH - OCgHs .. A -,; P, C — C-alkoxy; naphthyl, bromine, allyloxy; X oxygen, which exhibits insecticidal properties and can be used to kill German cockroaches. The goal is to create more active substances of the specified class. Their synthesis is carried out from the compounds j CA (CHF2) and BZ, where A, B, X — see above, Z is halogen, in the medium of an organic solvent in the presence of a base. New substances cause 80-100% mortality of cockroaches. 8 tab. and "about OJ
    公开号:SU1468402A3
    申请号:SU853960268
    申请日:1985-10-08
    公开日:1989-03-23
    发明作者:Франке Хельга；Франке Хайнрих；Крюгер Ханс-Рудольф；Йоппиен Хартмут
    申请人:Шеринг Аг (Фирма)；
    IPC主号:
    专利说明:

    162- (4-n-Butoxyphenyl) -2-difluoromethyl-1- (3-f-noxibenzyloxy) propane 1, 5492
    17 2- (4-n-butoxyphenyl) -2-difluoromethyl-1 (4-fluoro-3-phenoxybenzyloxy) propane 1.5410
    182- (4-Allyloxyphenyl) -2-difluoromethyl- - (3-phenoxybenzyloxy) propane1.5615
    192- (Allyloxyphenyl) -2-difluoromethyl-1 - (4-fluoro-3-phenoxbenzyloxy) propane 1,5530
    202-Difluoromethyl-2- 4- (2-4-methoxy) -phenyl - 1- (3-phenoxybenzloxy) -propan I, 550
    212-Difluoromethyl-1- (4-fluoro-3-phenoxybenzyl-hydroxy-2- (4-propargyloxyphenyl) propane 1.5547
    222- (4-Difluoromethoxyphenyl) -2-difluorome.til-1 (3-phenoxybenzyloxy) propane, 5382
    232- (4-Difluoromethoxyphenyl) -2-difluoromethyl-1- (4-fluoro-3-phenoxybenzyloxy) propane 1.5287
    242- (4-Bromophenyl) -2-di4 Tormethyl-1- (3-phenokeibenzyloxy) propane 1, 5767
    252- (4-Bromophenyl) -2-difluoromethyl-1- (4-fluoro-3-phenoxybenzyloxy) propane; 1.5681
    262- (4-Tert, -butylphenyl) -2-diphblmethyl-1- (3-phenoxybenzyloxy) propane1,5484
    272- (4-Tert.-butylphenyl) -2-difluoromethyl-1- (4-fluoro-3-phenoxybenzyloxy) propane 1.5404
    282-Difluoromethyl-2- (2-naphthyl) -1- (3-phenoxybenzyloxy) propane1.5969
    292-Difluoromethyl-2- (2-naphthyl) -1- (4-fluoro-3-phenoxybenzene-1) propane 1 5847
    302-Difluoromethyl-2- {3,4-dimethoxyphenyl) 1- (3-phenoxybenzyloxy) propane 1 5602
    312-Difluoromethyl-2- (3,4-dimethoxy4enyl) -1 (4-fluoro-3-phenoxybenzyloxy) propane 1.5555
    322- (1,3-Benzodioxol-5-yl) -2-difluoromethyl- 1- (3-phenoxybenzyloxy) propane 1.5692
    332- (1,3-Benzodioxol-5-yl) -2-difluoromethyl- 1- (4-fluoro-3-4 "noxibenzyloxy) propane 1.5602
    342-Difluoromethyl-1- (4-fluoro-3-phenoxy-benzyloxy) (2-fluoroethoxy) -phenylj-propan1, 5460
    35. 2-Difluoromethyl-1-1 3- (2-fluoroethoxy) -benzyloxy -2- (4-ethoxyphenyl) -propane1.5240
    362-, Ciforomethyl-1- 4- (2-fluoroethoxy) -benzyl- (4-ethoxyphenyl) -propan71-72 C
    372-Dipteromethyl-2- (4-ethoxyphenyl) (N-methylanilino) -benzyloxy-propane1, 5771
    382-Difluoromethyl-1- (3-phenoxybenzyloxy) (2,2,2-trifluoro-toxy) -phenyl) -propane 1,5283
    392-Difluoromethyl-1- (4-fluoro-3-phenoxy-benzyl-hydroxy-2-4-(2,2,2-trifluoroethoxy) -phenyl propane, 5209
    402-Difluoromethyl-2- (4-e toxiphenyl) -1- (3-L-ene-oxp1benzylthio) -propan1, 5783
    412-Difluoromethyl-2- (3,4-dimethoxyphenyl) -1- (6-phenox.-pyridin-2-ylmethoxy) propane 81.5-83.5 f.
    13
    IA68402
    14 Continuation of table 1
    2-Difluoromethyl-1- (3-phenoxybeneyl) 2- (4-n-propoxyphenyl) -propane
    2-Difluoromethyl-l- (4-ftor-3- (J € nocibenziloxyl) -2- (4-n-proxyphenyl) -propan
    2-Difluoromethyl-2- (4-isopropoxyphenyl) 1- (3-phenoxybenzyloxy) propane
    2-Difluoromethyl-1- (4-fluoro-3-phenoxybenzyloxy) -2- (4-isopropoxyphenyl) propane
    2- (4-n-Butoxyphenyl) -2-difluoromethyl-1 (3-phenoxybenzyloxy) propane
    2- (4-Chlorophenyl) -2-difluoromethyl-1- (4fluoro-3-phenoxybenzyloxy) propane 2- (4-Chlorophenyl) -2-difluoromethyl-1- (3phenoxybenzyloxy) propane
    2-Difluoromethyl-2- (4-methylphenyl) -1- (3fekoxy6enzyloxy) propane
    2-Difluoromethyl-1- (4-tor-3-4 enoxybenzyloxy) -2- (4-methoxyphenyl) propane
    2-Difluoromethyl-2- (4-methoxyphenyl) -1- (3phenoxybenzyloxy) propane
    2-Difluoromethyl-2- (4-methoxyphenyl) -I- (3phenoxybenzyloxy) propane
    2-Difluoromethyl-2- (4-fluorophenyl) -1- (4-fluoro3-phenoxybenzyloxy) propane
    2-Difluoromethyl-2- (4-fluorophenyl) -1- (3-phenoxybenzyloxy) -11ropane
    2-Difluoromethyl-2- (4-ethoxyphenyl) -1- (3phenoxybenzyloxy) propane
    2-Difluoromethyl 2- (4-ethoxyphenyl) -G- (4fluoro-3-phenoxybenzyloxy) propane
    2-Difluoromethyl-2- (4-ethoxyphenyl) -1- (6phenoxypyridin-2-ylmethoxy) propane
    2-Difluoromethyl-2- (4-fluorophenyl) -1- (6-phenoxypyridin-2-ylmethoxy) propane
    Table
    Known compound.
     Known compound
    2- (4-Ethoxyphenyl) -2-methyl-1- (3 phenoxybenzyloxy) gropane 2 (4-Bromophenyl) -2-difluorometap-1- (3-phenoxybenzyloxy) -prin 2- (4-Bromophenyl) -2-difluoromethyl 1- (4-fluoro-3-phenoxybenzidoxy) -progan 2-Difluoromethyl-1- (3-phenoxybenzyloxy) -2- (4-p-propoxyphenyl) -propane 2-Difluoromethyl-1- (4-fluoro-3-phenoxybenzyloxy ) -2 (4-p-Propoxyphenyl) -propane 2-Difluoromethyl 1- (4-fluoro-3-4-xenoxybenzyloxy) -2 (4-isopropoxyphenyl) -propane 2- (4-Chlorophenyl) -2-difluoromethyl-1- (4-fluoro-3-phenoxybenzyloxy) -propane 2- (4-chlorophenyl) -2-difluoromethyl-1- (3-phenoxybenzyloxy) -propan 2-Dif Toremethyl-2- (4-methylphenyl) -1- (3- phenoxybenzyloxy ) propane 1-Difluoromethyl-2- (4-fluoro-3-phenoxybenzyloxy) -2 (4-methoxyphenyl) propane
    Table 6
    Table 7
    80
    00
    100
    78
    100
    100
    100
    95
    100
    100
    2-Difluoromethyl-2- (4-methoxy (teyl) -G-NW-phenoxybenelyloxy) propane 2-Difluoromethyl-2 (4-fluorophenyl) -1- (A-fluoro-3-phenoxybenzyloxy) propane
    2-Difluoromethyl-2- (4-fluoro phenyl) -1 - (3-f. Phenoxybenzylsyl) propane
    2-Difluoromethyl - 2- (4-e toxiphenyl) -1 - (3-phenoxybeksyloxy) propane 2-Difluoromethyl-2 "(4-ethoxyphenyl) -1- (D-fluoro-3-phenoxybenzyloxy) propane 2- Difluoromethyl-2- (4-ethoxyphenyl) -1- (6-phenoxypyridin-2-ylmethoxy) propane,
    2-Difluoromethyl-2- (4-fluorophenyl) -1- (6-phenoxypyridine-2-Ylmethoxy) propane 2- (4-difluoromethoxyphenyl) -2-difluoromethyl-1- (3-phenoxybenzyloxy) propane
    2- (4-D Fluoromethoxyphenyl) -2-difluoromethyl-1- (4-fluoro-3-phenoxybenzyloxy) paragan
    2-Difluoromethyl-1- (3-phenoxybenzyloxy) (2,
    2,2-trifluoroethoxy) -phenyl-propane
    2-Difluoromethyl-1- (4-fluoro-3-phenoxybenzyloxy) (2,2,2-trifluoroethoxy) -phenyl-propane
    2- (4-p-Butoxyphenyl) -2-difluoromethyl-1- (4-fluoro-3phenoxybenzyloxy) propane 2-difluoromethyl-2- (4-ethoxyphenyl) -1- (3 - $ "Noxibenzylthio) propane 2- (4 Allyloxy (| enyl) -2-difluoromethyl-1- (4-fluoro-3phenoxybenzyloxy) propane
    2-Difluoromethyl-1- (6-phenoxy-pyridin-2-ylmethoxy) 2- (4-p-propoxyphenyl) -prprpan
    2- (4-Bromophenyl) -2-difluoromethyl-1- (6-phenoxypyri in-2-yl-methoxy) propane
    Known compound
    81
    100
    100
    100
    iOO
    95
    95
    100
    ioo
    7.5
    95
    83
    100
    85
    80
    100
    Table
    权利要求:
    Claims (2)
    [1]
    Claim
    The method of obtaining substituted benzyl esters of the General formula
    CHF / cn 3 -c-cn 2 -x-c, And where if B is a group of the formula CHgEC ' 4 ' 1 'i 4 6 8 4 O 2
    1 о where R ( is hydrogen, fluorine, then A is prefluorine, bromine, allyloxy, where R is chlorine, s
    (C-Sc. - alkyl, - alkoxygroup, or means fluorine C, - or C ^ alkoxygroup, or
    I, 3-benzodioxolane at R 'is hydrogen, fluorine, X is oxygen, or, if X is sulfur, then R is an ethoxy group;
    w-sn 2 • os 6 n 5
    N ti (1, 'b,' then A - < r - where where K is C ^ -C ^ - alkoxy, bromine, allyloxy, naphthyl;
    X is oxygen, characterized in that the compound of the formula sn 2
    CH.-C-CHOHN
    And where A and X have the indicated meanings, they are reacted with a compound of the formula
    BZ. Where B has the indicated meanings;
    Z is halogen in an anhydrous organic solvent in the presence of a base.
    Table 1
    When “measures Compound G ---Physical constants: η or so pl. 1 About l 3 2 2- (4 “Chlorophenyl) ~ 2-dif'Tormethyl-1- (3-phenoxybenzyloxy) prop.an 1,5659 3 2-Difluoromethyl-2- (4-methylphenip) -1- (3-phen-oxybenzyloxy) propane 1.5596 4 2-Difluoromethyl-1 ~ (4-fluoro ~ 3 ~ phenoxybenzyl-oxi) -2- (4-methoxyphenyl) propane 1.5581 5 1-Difluoromethyl-2- (4-methoxyphenyl) -1- (3-phenoxybenzyloxy) propane 1, 5615 6 2- Difluoromethyl-2- (4-fluorophenyl) ~ 1- (4-fluoro-3- phenoxybenzyloxy) propane 1.5427 7 2-Difluoromethyl-2- (4-fluorophenyl) -1- (3-phenok-sibenzyloxy) propane 1.5520 8 2-Difluoromethyl-2- (4-ethoxyphenyl) -1- (3phenoxybenzyloxy) propane 1, 5575 9 2-Difluoromethyl-2- (4-ethoxyphenyl) -1- (4-fluoro-3 ~ phenoxybenzyloxy) ~ propane 1, 5486 10eleven 2-Difluoromethyl ~ 2- (4-ethoxyphenyl-1- (6-phenoxypyridin-2-ylmethoxy) -propane2-Difluoromethyl-2- (4 ~ fluorophenyl ~ 1- (b-phen 1, 5557 hydroxypyridin-2-ylmethoxy) propane 1,5502 12 2-Difluoromethyl-1- (3-phenoxybenzyloxy) -2- (4-n-propoxyphenyl) propane 1.5532 thirteen 2-Difluoromethyl-i- (4-fluoro-3-phenoxybenzyl-hydroxy) -2- (4-n-propoxyphenyl) propane 1,5439 14 2-Difluoromethyl-2- (4-isopropoxyphenyl) -1-(3-phenoxybenzyloxy) propane 1.5528 fifteen 2-Difluoromethyl-1- (4-fluoro-3-phenoxybenzyloxy) -2- (4-ieopropoxyphenyl) propane 1, 5440
    eleven
    12
    Continuation of table 1
    [2]
    2 3
    16 2- (4-n ~ Butoxyphenyl) -2-difluoromethyl-1- (3fsnoxybenzyloxy) propane
    17 : 2- (4-n-butoxyphenyl) -2-difluoromethyl-1 ~ (4 ~ fluoro-3 ~ phenoxybenzyloxy) propane
    18 2- (4-Allyloxyphenyl) -2-difluoromethyl-1- (3 ~ phenoxybenzyloxy) propane
    19 2- (Allyloxyphenyl) -2-difluoromethyl-1- (4 fluoro-3 ~ phenoxybenzyloxy) propane
    20 2-Difluoromethyl-2- [4- (2-fluoroethoxy) phenyl] -
    1- (3-phenoxybenzyloxy) propane
    21 2-Difluoromethyl-1- (4 ~ fluoro-3-phenoxybenzyloxy-2- (4-propargyloxyphenyl) propane
    22 2- (4-Difluoromethoxyphenyl) -2-difluoromethyl-1 (3-phenoxybenzyloxy) propane
    23 2- (4-Difluoromethoxyphenyl) -2-difluoromethyl 1- (4-fluoro ~ 3 ~ phenoxybenzyloxy) propane
    24 2- (4-Bromophenyl) -2-difluoromethyl ~ 1- (3phenoxybenzyloxy) propane
    25 2- (4-Bromophenyl) -2-difluoromethyl-1- (4 fluoro-3-phenoxybenzyloxy) propane
    26 2- (4-Tert.-butylphenyl) -2-Difluoromethyl-1 (3-phenoxybenzyloxy) propane
    27 2- (4-Tert.-butylphenyl) -2-difluoromethyl-1 (4-fluoro-3-phenoxybenzyloxy) propane
    28 2-Difluoromethyl ~ 2- (2-naphthyl) -1- (3-phenoxybenzyloxy) propane
    29 2-Difluoromethyl-2- (2-naphthyl ') - 1- (4-fluoro-3 ~ phenoxybenzyloxy) propane
    30 2-Difluoromethyl-2- (3,4-dimethoxyphenyl) 1 (3-phenoxybenzyloxy) propane
    31 2-Difluoromethyl ~ 2 ~ (3,4-dimethoxyphenyl) - Ι-
    Ο /; - fluoro-3-phenoxybenzyl oxy) propane
    32 2- (1,3-Benzodioxol-5 ~ yl) -2-difluoromethyl-
    1- (3-Phenoxybenzyloxy) propane
    33 2- (1,3-Benzodioxol-5-yl) -2-difluoromethyl 1- (4 ~ fluoro-3-phenoxybenzyloxy) propane
    34 2-Difluoromethyl-1- (4-fluoro-3-phenoxybenzyloxy) -2- £ 4- (2-fluoroethoxy) phenyl] propane
    35. 2-Difluoromethyl-1- £ 3- (2-fluoroethoxy) benzyl-oxy] -2- (4-ethoxyphenyl) propane
    36 2-Difluoromethyl-1- [4- (2-fluoroethoxy) -5enzyloxy] -2- (4-ethoxyphenyl) propane
    37 2-Difluoromethyl ~ 2- (4-ethoxyphenyl) -1- [3- (Ν’methyl anilino) benzyloxy] propane
    38 2-Difluoromethyl-1- (3 ~ phenoxybenzyloxy) -2 [4- (2,2,2-trifluoroethoxy) phenyl / propane
    39 2-Difluoromethyl-1- (4-fluoro-3-phenoxybenzyloxy) -2- [4- (2,2,2-trifluoroethoxy) phenyl] propane
    40 2-Difluoromethyl-2- (4-ethoxyphenyl) -1 ~ (3-phenoxybenzylthio) propane
    41 2-Difluoromethyl-2- (3,4-dimethoxyphenyl) -1 (6-phenoxypyridin-2 ~ ylmethoxy) propane
    1, 5492
    I, 5410
    1, 5615
    I, 5530
    1 ’, 550
    1, 5547
    1,5382
    1, 5287
    1, 5767
    1,5681
    1,5484
    1,5404
    1,5969
    10847
    1,5602
    1,5555
    1, 5692
    1,5602
    1, 5460
    1,5240
    71-72 ° C.
    1,5771
    1,5283
    1,5209
    1,5783
    81.5-83.5 ° C
    thirteen
    14
    - Continuation of table 1 - 1 1 gI 5 42 2- (4-Bromophenyl) -2-difluoromethyl-1- (6-phenoxypyridin-2-ylmethoxy) propane 1,5750 43 2-Difluoromethyl ~ 2- (2-naphthyl) -1- (6-phenoxy-pyridin-2-ylmethoxy) -procane 1, 5951 44 , 2- (4-allyloxyphenyl) -2-difluoromethyl-1-(b-phenoxypyridin-2-ylmethoxy) propane 1,5600 45 2-Difluoromethyl-1- (6-phenoxypyridin-2-ilmethoxy) -2- (4-n-propoxyphenyl) propane 1,5509 46 2-Difluoromethyl ~ 2- (4-ethoxyphenyl) ~ Na-methyl 3-phenyl benzyl hydroxy) propane 1,5621
    table 2
    Compound The concentration of biologically active substances, 7, Assets-nost7s 1 2 3 2-Difluoromethyl-1- (3-phenoxybenzyloxy) -2- (4-n-propoxyphenyl) propane 0.1 100 2-Difluoromethyl- 1- (4-fluoro-3 ~ 4'enoxybenzyloxy) -2- (4-n-propoxyphenyl) propane 0.1 100 2-Difluoromethyl-2- (4-isopropoxyphenyl) -1- (3-phenoxybenzyloxy) propane 0.1 100 2-Difluoromethyl-1- (4-fluoro-3 ~ phenoxybenzyloxy) -2- (4-isopropoxyphenyl) propane 0.1 100 2- (4-n ~ butoxyphenyl) ~ 2-difluoromethyl-1 (3-phenoxybenzyloxy) propane 0.1 100 2- (4-Chlorophenyl) -2-difluoromethyl-1- (4 fluoro-3-phenoxybenzyloxy) propane . 0.1 100 2- (4 ~ Chlorophenyl) -2-difluoromethyl-1- (3 ~ phenoxybenzyloxy) -propane 0.1 100 2-Difluoromethyl-2- (4-methylphenyl) -1- (3phenoxybenzyloxy) propane 0.1 100
    2-Difluoromethyl-1 - (4-fluoro ~ 3- (1 enoxy benzyl-
    hydroxy) -2- (4-methoxyphenyl) propane 0.1 100 2-Difluoromethyl-2- (4-methoxyphenyl) - | - (3-phenoxybenzyloxy) propane 0.1 100 2-Difluoromethyl-2- (4-methoxyphenyl) ~ 1- (3-phenoxybenzyloxy) propane 0.1 100 2- Difluoromethyl-2- (4-fluorophenyl) -1- (4-fluoro-3- phenoxybenzyloxy) propane 0.1 100 2-Difluoromethyl-2- (4-fluorophenyl) -1- (3-phen-oxybenzyloxy) propane 0.1 100 2-Dif ormethyl-2- (4-toxiphenyl) -1- (3phenoxybenzyloxy) propane 0.1 100 2-Difluoromethyl ~ 2- (4-ethoxyphenyl) -1- (4-fluoro-3-phenoxybenzyloxy) -propane 0.1 100 2-Difluoromethyl-2- (4 ~ ethoxyphenyl) -1- (6-phenoxypyridin-2 ~ ylmethoxy) -propane 0.1 100 2-Difluoromethyl-2- (4-fluorophenyl) -1- (6-phenoxypyridin-2-ylmethoxy) propane 0.1 100
    fifteen
    16
    Continuation of Table 2
    4 2 3 2-Difluoromethyl-2- (3-4-dimethoxyphenyl) -1 ~ (3 ~ phenoxybenzyloxy) ”propane 0.1 65 2-Difluoromethyl-2 ~ (3,4-dimethoxyphenyl) -1- (4-fluoro ~ 3 ~ phenoxybenzyloxy) propane 0.1 94 2 - (. 1 s 3 ”Benzodioxol-5-yl) -2-difluoromethyl-1- (3-phenoxybenzylrxi) -propane 0.1 100 2- (1 3 3 ~ Benzodioxol ~ 5-yl) ~ 2-difluoromethyl-1- (4 ~ fluoro ~ 3-phenoxybenzyloxy) - propane 0.1 65 2-Difluoromethyl-2- (4-ethoxyphenyl) - 1- [3-(Ν-methylanilino) -benzyloxy] propane 0.1 88 2-Difluoromethyl-2- (2-naphthyl) -1- (3-phenoxy-benzyloxy) propane 0.1 100 2-Difluoromethyl. ~ ’2 ~ (2-naphthyl) -1- (4-fluoro-3-phenoxybenzyloxy) propane 0.1 100 2- Elevator type 2 - (2. - n aftyl) -1- (6 * pheno to si-py.ridin-2-ylmethoxy) propane 0.1 90 2- (4 ~ Difluoro methoxyphenyl) -. 2 ~ difluoromethyl-1 (3 - phenoxybenzyloxy) -propane 0.1 100 2- (4-Difluoromethoxyphenyl) -2-difluoromethyl ~1- (4-fluoro-3-phenoxybenzyloxy) propane 0., 1 100 2- (4-Tr. □-butylphenyl) -2-difluoromethyl-1-(3-phenoxybenzyloxy) propane ° 1 60 2- (4 ~ Tert, butylphenyl) -2- difluoromethyl-1 - (4-fluoro · -3- · pheno xyl benzyl si) -propane 0.1 70 2. ~ Difluoromethyl-2- (4-ethoxyphenyl) -1- (2-methyl-3-phenylbenzyloxy) propane 0.1 85 2-Difluoromethyl-1- (4-fluoro-3-phenoxybenzyl-about to her) - 2- (4- pr about p ar arilo xiphenyl) - pr opan 0.1 100 2-Difluoromethyl-1- (3-phenoxybenzyloxy) -2- G4- (2. 2 s . 2t-trifluoroethoxy) “phenyl] propane 0.1  100 2 -di ft op IU til- ΐ - (4-3-ft.or- fenok sibenziloksi) -2- j 4'- (2 P 2.2 ~ trifluoroethoxy) * phenyl] propane 0.1 100 2-Difluoromethyl-2-G4- (2-fluoroethoxy) phenyl] -1- (3-Phenoxybenzyloxy) propane ' 0.1 100 2-Difluoromethyl-1- (4-fluoro-3-phenoxybenzyl-hydroxy) -2 ~ [4- (2-fluoroethoxy) phenyl] propane 0.1 100 2-Difluoromethyl-1 - () 3- (2-fluoro ethoxy) benzyloxy] -2- (4-ethoxyphenyl) propane 0.1 100 2-Dif torme tyl-2- (4 ~ e-toxiphenyl) -1- (3-phenoxybenzylthio) -propane 0.1 . 100 2-Difluoromethyl-1- [4 - '(2-fluoroethoxy) benzyl-hydroxy] -2- (4-ethoxyphenyl) propane 0.1 100 2- (4-n ~ Butoxyphenyl) -2-dif’tor methyl-1- (4-fluoro-3-phenoxybenzyloxy) propane. 0.1 100 2- (4-allyloxyphenyl) -2 ~ difluoromethyl-1-(3-phenoxybenzyloxy) propane 0.1 100 2- (4 ~ Allylo to si phenyl) -2-difluoromethyl-1 (4-fluoro-3-phenoxybenzyloxy) propane 0.1 100 2-Difluoromethyl ~ 2 ~ (3 e 4-dimethoxyphenyl) - 1- (b-phenoxypyridin-2-ylmethoxy) - propane 0.1 65 2- (4-Bromophenyl) ~ 2 ~ difluoromethyl-1- (6 “phenoxypyridin-2-ylmethoxy) propane 0.1 100
    1 7
    . Continuation tab. 2 4 12 thirteen 2- (4-Bromophenyl) -2 ~ difluoromethyl ~ 1-(3-Phenoxybsynzyloxy) propane2- (4-Bromophenyl) -2-difluoromethyl-1- (4- . oh 1 100 . fluoro-3-phenoxybenzyloxy) propane2 ~ (4-allyloxyphenyl) -2-difluoromethyl- 0.1 1'00 1- (6-phenoxypyridin-2-ylmethoxy) ~propane 0.1 100 T a b l Ts a 3 Concentration Assets- Compound biologically nost active "7/about substances Z 2-Difluoromethyl-2- (4-ethoxyphenyl) -1- (3-phenoxybenzyloxy) propane2- Difluoromethyl-2- (4-ethoxyphenyl) -1 (4-fluoro-3-phenoxybenzyloxy) - 0.001 80 propane 0.001 100 2- (4-Difluoromethoxyphenyl) -2-difluoromethyl-1 - (4-fluoro-3-phenoxybeneyloxy) propane2- (4-Ethoxyphenyl) -2-methyl-1- (3- 0.001 100 phenoxybenzyloxy) propane 0.001 55 Tables a 4
    Compound The concentration of biologically active substances,% Assets-% 2-Difluoromethyl-2- (4-ethoxyphenyl) - 0.0025 90 1- (4-fluoro-3 ~ phenoxybenzyloxy) - 0.0010 fifty propane2- (4-Ethoxyphenyl) -2-methyl-1- 0.0025 10 (3-Phenoxybenzyloxy) propane 0.0010 0 1 Table and 5
    Concentration Assets- Compound biologically nost active % substances,%
    2-Difluoromethyl-2- (4-ethoxyphenyl) -1 (4-fluoro-3-phenoxybenzyloxy) propane
    2- (4-Difluoromethoxyphenyl) -2-difluoromethyl-l- (4-φτop-3-phenoxybenzyloxy) -propane | - (4-Eth hydroxyphenyl) ** 2-methyl-1- (3phenoxybenzyloxy) propane *
    0,064 100 0.0025 100 0.001 80 0.0064 100 0.0025 100 0.001 80 0.0064 90 0.0025 70 0.001 0
    Known compound.
    Table 6
    Compound The concentration of biologically active substances,% Effect on mobile stages / eggs Tetranychus urticae),% 2- (4-Chlorophenyl) ~ 2 ~ difluoromethyl-1-(4-fluoro-3-phenoxybenzyloxy) propane2-Difluoromethyl-2- (4-fluorophenyl) -1 (4-fluoro-3-phenoxybenzyloxy) - 0.1 95/40 propane2-Difluoromethyl-2- (4-ethoxyphenyl) ~1- (4-fluoro-3-phenoxybenzyloxy) - 0.1 100/0 propane2-Difluoromethyl-2- (4-fluorophenyl) ~ 1 (6 ~ phenoxypyridin-2-ylmethoxy) - 0.1 75/25 propane 0.1 93/94 2- (4-Difluoromethoxyphenyl) -2-difluoromethyl-1 - (4-fluoro-3-phenoxybenzyloxy) propane2- (4 ~ Ethoxyphenyl) -2-methyl-1- (3- 0.1 100/0 phenoxybenzyloxy) propane * 0.1 38/4
    I
    Known Compound
    Table 7
    Connected! ® - - -Mortality,% 1 2
    2- (4-Ethoxyphenyl) -2-methyl-1- (3 ~ phenoxybenzyloxy) gropan * 80
    2 .- (4-Bromophenyl) “2-difluoromethyl-1 - (3-phenoxybenzyloxy) -prbpan100
    2- (4-Bromophenyl) -2-difluoromethyl ~ 1- (4-fluoro ~ 3-phenoxybenzyloxy) propane 100
    2-Difluoromethyl-1- (3-phenoxybenzyloxy) -2- (4-p ~ propoxyphenyl) propane78
    2-Difluoromethip-1- (4-fluoro-3-phenoxybenzyloxy) ~ 2 (4-p-Propoxyphenyl) propane 100
    2-Difluoromethyl ~ I - (4-fluoro-3-4enoxybenzyloxy) -2 ~ (4-isopropoxyphenyl) propane 100
    2- (4-Chlorphe_nyl) -2 ~ difluoromethyl-1 - (4-fluoro-3-phenoxybenzyloxy) propane 100
    2- (4 ~ chlorophenyl) -2-diFluoromethyl-1- (3-phenoxybenzyloxy) ~ propane95
    2-Difluoromethyl-2- (4-methylphenyl) -1- (3-phenoxybenzyloxy) propane 100
    1-Difluoromethyl-2- (4-fluoro-3-phenoxybenzyloxy) ~ 2 (A-methoxyphenyl) propane 100
    Continuation of Table 7
    2-Difluoromethyl-2- (4-methoxyphenyl) - 1- (3-phenoxybenzyloxy) propane81
    2-Difluoromethyl-2 ~ (4 — fluorophenyl) —1— (4 — fluoro-3-phenoxybenzyloxy) ~ propane100
    2-Difluoromethyl-2- (4-fluorophenyl) -1- (3-phenoxybenzyloxy) propane 100
    2-Difluoromethyl ~ 2- (4-ethoxyphenyl) -1- (3-phenoxybekzyloxy) propane 100
    2-Difluoromethyl-2g (4-ethoxyphenyl) -1- (4-fluoro-3-phenoxybenzyloxy) -propaneΐ00
    2-Difluoromethyl-2- (4-ethoxyphenyl) -! - (6-phenoxypyridin-2-ylmethoxy) propane95
    2-Difluoromethyl-2- (4-fluorophenyl) -1- (6-phenoxypyridin-2 ~ ylmethoxy) -propane95
    2- (4-Difluoromethoxyphenyl) -2-difluoromethyl-1- (3-phenoxybenzyloxy) propane .100
    2- (4-Difluoromethoxyphenyl) -2-difluoromethyl-1- (4fluoro-3 ~ phenoxybenzyloxy) propane 100
    2-Difluoromethyl-1- (3-phenoxybenzyloxy) -2- [4- (2, 2,2-trifluoroethoxy) phenyl] propane I7.5
    2-Difluoromethyl-1- (4-fluoro-3-phenoxybenzyloxy) 2- [4- (2,2,2-trifluoroethoxy) phenyl ^ propane95
    2- (4-p-Butoxyphenyl) -2-difluoromethyl-1- (4-fluoro-3phenoxybenzyloxy) propane83
    2-Difluoromethyl-2- (4-ethoxyphenyl) -1- (3-phenoxybenzylthio) propane 100
    2- (4 “Allyloxyphenyl) -2-difluoromethyl-1- (4-fluoro-3phenoxybenzyloxy) propane85
    2-Difluoromethyl-1- (6-phenoxy-pyridin-2-ylmethoxy) 2- (4-p-propoxyphenyl) propane80
    2- (4-Bromophenyl) -2-difluoromethyl-1- (6-phenoxypyri, gin-2-yl-methoxy) propane 100
    Known Compound
    Table 8
    Example Exit,Ζ Elemental analysis P 2656 1 2 3 4
    2 94.7 s ge n g , s 1 g g o 4(402.9) FROM 68.57; N 5.25; C1 8.81; F 9.43 FROM 68.54; n 6.19; C1 9.02; F 9.45 3 98.0 ^ 24 ^ 2.4 ^ 2.02. (382.4) FROM 75.37; n 6.33; F 9.93 FROM 75.20; n 6.51; F 9.62 4 79.3(416.4) FROM 69.22; n 5.57; F 13.69 FROM 68.85; n 5.56; F 13.84 5 80.3С 24 Н «^ 0з (398.4) FROM 72.34; n 6.07; F 9.54 FROM 72.09 ; H, 6.02 ; f '9.64 6 84.5 Sc B 20 ^ 4 θ2 (404.4) FROM 68.31 "; N 4.99; F 18.79 FROM 68.54; N 5.02; F 19.18 7 89.3 ^ 23 V 2, (386.4) FROM 71, 49; 1 Η ί *, 48; : F 1 4.75 from 71.49; n 5.67; F 14.47
    Continuation of table. 8 '
    1 a ’3 4 8 95.5(412.5) C 72.50; H 6.35; F 9.21 C 73.07; H 6.74; F 9.20 9 86.2C 25 H „F 3 O g(430.5) c 69.75; H 5.86; F 13.24 c 69.78; H 5.73; F 13.64 10 66.8 c 24 h 25 f 2 no, (413.5) c 69.72; H 6.09; F 9.19; N 3.39 c 69.68; H 6.02; F 9.15; N 3.56 eleven 73.3 C 22 H 2 O F g NO 2(387.4) c 68.20; H 5.21; F 14.71; N 3.62 c 68.20; H 5.01; F 14.38; N 3,57 12 93.8 ^ 26 ^ 28 ^ -2θ3 (426.5) c 73.22; H 6.62; F 8.91 c 73.30; H 6.70; F 8.59 thirteen 72.0(444.5) c 70.25; H 6.12; F 12.83 c 70.26; H 6.28; F 12.77 14 92.4 c 26 h z8 f 2 o 3(426.5) c 73.22; H 6.62; F 8.91 c 73.21; H 6.58; F 8.76 fifteen 86.9 ^ 26 F g Oj (444.5) c 70.25; H 6.13; F 12.82 c 70.31; H 6.07; F 12.64 16 83,2S 27 N D F 2 C 3 (440.5) c 73.61; H 6.86; F 8.63 c 73.50; H 6.89; F 8.49 17 92.8(458.5) c 70.72; H 6.38; F 12,43 c 70.83; H 6.55; F 12.15 18 70,2(424.5) c 73.56; H 6.18; F 8.95 c 73.62; H 5.89; -F 8.56 19 89.0C 26 H 2 F 3 ° 3 (442.5) c 70.57; H 5.70; F 12.88 c 70.44; H 5.94; F 12.50 20 85.8C 2ALe ° 3 ’(430.5) c 69.75; H 5.85; F 13.24 c 70.07; H 5.90; F 13.1 1 21 95.1 v 26 ^ 2 3 ^ 3θ j (440.5) c 70.90; H 5.26; F 12.94 c 71.05; H 5.78; F 12.54 22 96.1 ^ 24 ^ 22 ^ 4 ^ 3 (434.4) c 66.35; P 5.11; F 17.49 c 66.76; H 4.93; F 17.42 23 91.0 0.74823 F ^ 0 Oe(452.4) c 63.71; H 4.68; F 21.00 c 63.68; H 4.75; F 21.32 24 98.0 C 23 H 7 , BrF 2 0 2(447.3) c 61.75; H 4.73; B 17.87; F 8.50 c 61.13; H 4.72; IN 18.22; F 8.24 ’ 25 65.3 ^ 23 ^ 20 ^^ 3 ^ 2 . (465.3) c 59.37; H 4.33; IN 17.17; F 12.25 c 59.40; H 4, H; IN 17.00; F 12.22 26 52.9 ^ 278 3o8 2 0 z(424.5) c 76.39; H 7.12; F 8.95 c 76.25; H 7.10; F 8.47 27 77.4 C 27 H 2 4 F g 0 2(442.5) c 73.28; H 6.61; F 12.88 c 73.26; H 6.56; F 12.67 28 79.0 C 27 8548 ^ 0 ^ (418.5) c 77.49; H 5.78; F 9.08 c 77.45; H 5.66; F 9.07 29 - 84.9 C 17 MA (436.5) c 74.30; H 5.31; F 13.06- c 73.78; H 4.94; F 12.53 thirty 97.7C 2 5 8 26 F 2 0 4(428.5) c 70.07; H 6.12; F 8.87 c 69.94; H 6.19; F 8.82 31 84,4F '2 8.75 83 θ4 (446.5) c 67.25; H 5.64; F 12.77 c 67.18; H 5.68; F 12.63 32 78,2 C 74 8 ^ 2 F ^ 0 4(412.4) c 69.89; H 5.38; F 9.21 c 69.75; H 5.61; F 9.06 33 92.4 0ι 4 Η α1 F g 0 4(430.4) c 66.97; H 4.92; F 13.24 c 66.51; H 4.62; F 13.18 34 91.6C 25 H 24 F 4 ° 3 (448.4 ^ c 66.95; H 5.39; F 16.95 c 67.15; H 5.43; F 17.00
    λ -,
    1 /. 687 02
    Continuation of that Ch. 8 1 . i * G11 435 67.5(382.4) C 65.95; N 6 . ’, 59; F 14.91. C 66.03;6 , 61; F 15.0036 30,0(382.4) C 65.95; • 1 p £ Щ9; F 14.91C 65.85; n 6 83: F 14.6337 82.1 c 26 h 7 , f 2 no, (425.5) C 73.39; n 6 , 37; F 8.93; N 3κ 29 S. 73.07; n b , 88; F 8.9.1;,thirty 38 90.3C 7.5 H Z3 F 5- 0 3 (466.4) C 64.37; TG 4 97; F 20.37C 64.40; n 5 , 04; F 20.7039 94.7 W 6 o B(484.4) C 61.98; n H- .59; F 23.53C 61.96; n 4 , 56; F 24.0140 70.9 ^ 25 ^ 26 (428.5) C 70.07; n 6 ,12; I 8.87; ς 7 , 48 C 69.9-6; n 6 , 06; F 8.85; S 7 , 22 41 79.2 C 24 H i3 1 · , N0 ^ (429.5) C, 67.12; n 5 , 87; D 8.85; N 3 rs r $ zo C 67, 07 ;, g6 i; F 8.71; N 3, 10 42 95.0 H ^ BrF ^ (448.3) C, 58.94; n 4, fifty; S 1 i t, j; F 8 - F 4 7; 3.12 1 C 58., 92; n 4 ; 68; B 17.43; F 8 .47; 3.04 43 62.0 c 26 h Z3 f 2 no 2(419.5) C 75.45: n 5 s5 3; .! 9.06; H 3 34 C 73.57; n 5 . 48: F 8.82: N 3, 00 44 86.0C 2S H 2S F 2 N ° 3 (425.0) C / 0.57; n ς 92; F 8.93; N 3, 29th C 70.26: m 6. 05: F 8.72; N 3. fifteen 45 82.3(427.5) C 70.24; and 6 s 37: F 8.88; N 3. 28 C 70.26; n 6 16; F 8.55; N 3. 22 4Έ 80.00 ^ 26 ^ 23 U, 0 2(410.5) C 76.07; n 6 88; F 9.26C 76.07; E 6 83; F 9.02
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    同族专利:
    公开号 | 公开日
    CN85107643A|1986-08-20|
    BR8505133A|1986-07-29|
    AU4873685A|1986-04-24|
    PH22263A|1988-07-01|
    DD250451A5|1987-10-14|
    IL76643D0|1986-02-28|
    ZA857999B|1986-05-28|
    US4678811A|1987-07-07|
    DK475685A|1986-04-18|
    ES8604847A1|1986-03-16|
    KR860003192A|1986-05-21|
    DK475685D0|1985-10-17|
    ES547924A0|1986-03-16|
    HU196352B|1988-11-28|
    HUT41365A|1987-04-28|
    EP0179018A1|1986-04-23|
    DE3438483A1|1986-04-17|
    FI854049A0|1985-10-17|
    JPS61178945A|1986-08-11|
    引用文献:
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    US3966824A|1972-12-26|1976-06-29|University Of Illinois Foundation|P,P'-Disubstituted α-trichloromethylbenzylphenyl ethers|
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    US4397864A|1980-05-02|1983-08-09|Mitsuitoatsu Chemicals Inc.|2-Arylpropyl ether or thioether derivatives and insecticidal and acaricidal agents containing said derivatives|
    JPS6355500B2|1980-10-09|1988-11-02|Mitsui Toatsu Chemicals|
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    GB8605281D0|1986-03-04|1986-04-09|Ici Plc|Diphenyl ether derivatives|
    US4840971A|1986-04-07|1989-06-20|Sumitomo Chemical Company, Limited|Novel ether compound, a process for manufacturing the same, a composition containing the same and a use thereof|
    DE3628300A1|1986-08-21|1988-02-25|Schering Ag|ALKANE AND ALKOXYALKANE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND INSECTICIDES AND ACARICIDES CONTAINING THESE COMPOUNDS|
    GB8624831D0|1986-10-16|1986-11-19|Ici Plc|Insecticidal ethers|
    GB8625897D0|1986-10-29|1986-12-03|Ici Plc|Insecticidal thioethers derivatives|
    EP0276558B1|1987-01-08|1992-07-08|Imperial Chemical Industries Plc|Insecticidal ethers|
    GB8702717D0|1987-02-06|1987-03-11|Ici Plc|Insecticidal compounds|
    US5536442A|1987-09-25|1996-07-16|Merck Patent Gesellschaft Mit Beschrankter Haftung|Fluorinated liquid crystal compounds and liquid crystal medium containing same|
    US5324449A|1987-09-25|1994-06-28|Merck Patent Gesellschaft Mit Beschrankter Haftung|Substituted phenyl trifluoromethyl ethers|
    EP0315370A3|1987-11-04|1990-11-22|Sumitomo Chemical Company, Limited|Ether compounds and their production, and insecticidal and/or acaricidal compositions containing them|
    DE3909802A1|1988-07-27|1990-04-05|Merck Patent Gmbh|DIFLUORMETHYLVERBINDUNGEN|
    GB8822793D0|1988-09-28|1988-11-02|Ici Plc|Insecticidal compounds|
    GB8822792D0|1988-09-28|1988-11-02|Ici Plc|Insecticidal compounds|
    FR2645536B1|1989-04-10|1991-05-31|Rhone Poulenc Agrochimie|HERBICIDE COMPOUNDS AND COMPOSITIONS CONTAINING THEM|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19843438483|DE3438483A1|1984-10-17|1984-10-17|SUBSTITUTED BENZYL ETHER, PEST CONTROL, CONTAINING THESE COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF|
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