DE1913043A1 - Substituted phenyl carbamates - Google Patents
Substituted phenyl carbamatesInfo
- Publication number
- DE1913043A1 DE1913043A1 DE19691913043 DE1913043A DE1913043A1 DE 1913043 A1 DE1913043 A1 DE 1913043A1 DE 19691913043 DE19691913043 DE 19691913043 DE 1913043 A DE1913043 A DE 1913043A DE 1913043 A1 DE1913043 A1 DE 1913043A1
- Authority
- DE
- Germany
- Prior art keywords
- anilide
- carboxylic acid
- acid
- carbamoyloxy
- oximinopentane
- Prior art date
- 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.)
- Granted
Links
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical class NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 title description 9
- 150000003931 anilides Chemical class 0.000 claims description 185
- -1 hydrocarbon radical Chemical class 0.000 claims description 144
- 239000002253 acid Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000004215 Carbon black (E152) Substances 0.000 claims description 13
- 229930195733 hydrocarbon Natural products 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 230000002363 herbicidal effect Effects 0.000 claims description 5
- 239000004009 herbicide Substances 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 150000007530 organic bases Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 241000251730 Chondrichthyes Species 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 150000002923 oximes Chemical class 0.000 claims description 2
- 150000003606 tin compounds Chemical class 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- NAQQTJZRCYNBRX-UHFFFAOYSA-N n-pentan-3-ylidenehydroxylamine Chemical compound CCC(CC)=NO NAQQTJZRCYNBRX-UHFFFAOYSA-N 0.000 claims 2
- 125000004188 dichlorophenyl group Chemical group 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- HZCRFUPEBRNAAI-UHFFFAOYSA-N n-(3-methylbutan-2-ylidene)hydroxylamine Chemical compound CC(C)C(C)=NO HZCRFUPEBRNAAI-UHFFFAOYSA-N 0.000 claims 1
- FWSXGNXGAJUIPS-UHFFFAOYSA-N n-pentan-2-ylidenehydroxylamine Chemical compound CCCC(C)=NO FWSXGNXGAJUIPS-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 11
- 210000003608 fece Anatomy 0.000 description 11
- 241000219198 Brassica Species 0.000 description 10
- 235000003351 Brassica cretica Nutrition 0.000 description 10
- 235000003343 Brassica rupestris Nutrition 0.000 description 10
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 10
- 235000010460 mustard Nutrition 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 240000003768 Solanum lycopersicum Species 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 244000042664 Matricaria chamomilla Species 0.000 description 4
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 244000105624 Arachis hypogaea Species 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000209504 Poaceae Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 235000020232 peanut Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 244000274883 Urtica dioica Species 0.000 description 2
- 235000009108 Urtica dioica Nutrition 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- UVMTZTPUIFOAGM-UHFFFAOYSA-N (3-chlorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC(Cl)=C1 UVMTZTPUIFOAGM-UHFFFAOYSA-N 0.000 description 1
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- RNVZSRCFFKMGCM-UHFFFAOYSA-N 3-hydroxyiminobutanoyl chloride Chemical compound ClC(=O)CC(C)=NO RNVZSRCFFKMGCM-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 244000007645 Citrus mitis Species 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 206010011878 Deafness Diseases 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 241000520028 Lamium Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 241000508727 Oloptum miliaceum Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 240000003705 Senecio vulgaris Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/60—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups having oxygen atoms of carbamate groups bound to nitrogen atoms
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
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- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
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- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
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- 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
- A01N43/10—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 with sulfur as the ring hetero atom
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- 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
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
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Description
SCHERING AGSCHERING AG
P.112 6.0 O/Dr.Li e/ßiP.112 6.0 O / Dr Li e / ßi
6. März 1969March 6, 1969
Substituierte Phenylcarbamate. Substituted phenyl carbamates .
Die Erfindung "betrifft neue substituierte Phenylcarbamate, deren Vervrendung als herbizide Mittel insbesondere mit selektiver herbizider Wirkung sowie Verfahren zur Herstellung dieser Verbindungen.The invention "relates to new substituted phenyl carbamates, their use as herbicidal agents, in particular with selective herbicidal action, and processes for their production of these connections.
Die herbizide Wirkung von substituierten Phenylcarbamaten ist bereits bekannt· Vertreter sind z.B. in der belgischen Patentschrift Nr. 679.283 beschrieben, wie 3-(Alkoxycarbonylaminophenyl)-N-arylcarbamate. .The herbicidal effects of substituted phenyl carbamates is already known Representatives are described e.g. in Belgian patent specification No. 679.283, such as 3- (alkoxycarbonylaminophenyl) -N-arylcarbamate. .
Diese Carbamate weisen zwar überwiegend eine ausgeprägte Wirkung gegen 2 «-keimblättrige Pflanzenarten auf, entfalten jedoch nur eine geringe Selektivität gegenüber Eulturgräsern.These carbamates mainly have a pronounced effect against 2 -cotyledonous plant species, unfold however, only a low selectivity for cultivated grasses.
Es wurde nun gefunden, daß Verbindungen der allgemeinen PormelIt has now been found that compounds of the general formula
0 - OY- Ε,0 - OY- Ε,
■in der■ in the
009838/2282009838/2282
P. 1126.00/Dr.Lie/RiP. 1126.00 / Dr Lie / Ri
R1 und Rp gleich oder verschieden sind und einen gegebenenfalls ein- oder mehrfach substituierten aromatischen, aliphatischen, cycloaliphatischen oder araliphatischen Kohlenwasserstoffrest,R 1 and Rp are the same or different and an optionally mono- or polysubstituted aromatic, aliphatic, cycloaliphatic or araliphatic hydrocarbon radical,
R-, außer der vorgenannten Bedeutung Wasserstoff,R-, except for the meaning given above, hydrogen,
R-, und Rg gemeinsam mit dem Kohlenstoffatom einen gegebenenfalls ein- oder mehrfach substituierten cycloaliphatischen Kohlenwasserstoffrest,R-, and Rg together with the carbon atom an optionally mono- or polysubstituted cycloaliphatic Hydrocarbon residue,
R, einen gegebenenfalls ein- oder mehrfach substituierten aliphatischen, cycloaliphatischen, aromatischen oder araliphatischen Kohlenwasserstoffrest, einen Alkoxy- oder einen Aryloxyrest, oder die GruppenR, an optionally mono- or polysubstituted aliphatic, cycloaliphatic, aromatic or araliphatic hydrocarbon radical, an alkoxy or an aryloxy radical, or the groups
oderor
A"A "
0 - IT =0 - IT =
mit R-)1» 5I1Vt Rp' und ^2" ^"n der Bedeutung von ^n und/oder R2, wobei R1 1 und R2 1 weiterhin gemeinsam mit dem ii-Atom für/gegebenenfalls weitere U"- und/oder O-Atome enthaltenden heterocyclischen Ring und R-, ' und R^" jeweils allein für einen heterocyclischen Rest und R1 1 außerdem für einen durch einen heterocyclischen Restwith R-) 1 »5 I 1 VT Rp 'and ^ 2' ^ 'n meaning of ^ n and / or R 2, wherein R 1 1 and R 2 1 further together with the ii-atom / optionally other U "- and / or O atom-containing heterocyclic ring, and R 'and R" each alone for a heterocyclic radical and R 1 1 is also applicable to a by a heterocyclic radical
009838/2282 - 3 -009838/2282 - 3 -
substituierten aliphatischen Kohlenwasserstoffrest stehen,substituted aliphatic hydrocarbon radical,
R. und Rc gleich oder=verschieden sind und Wasserstoff oder einen aliphatischen Kohlenwasserstoffrest undR. and Rc are identical or different and are hydrogen or an aliphatic hydrocarbon radical and
X und Y gleich oder verschieden sind und Sauerstoff oder Schwefel darstellen,X and Y are identical or different and are oxygen or Represent sulfur,
herbizid wirksam sind und insbesondere zur Bekämpfung von Unkräutern in Kulturgräsern verwendet werden können.are herbicidally effective and can be used in particular to control weeds in cultivated grasses.
Die Wirkung der erfindungsgemäßen Phenylcarbamate, im folgenden als O-Carbonsäureanilide bezeichnet, erstreckt sich bei einer Vielzahl ihrer Vertreter sowohl auf die Anwendung im Vorauflauf- als auch im Nachauflaufverfahren. Bei einer Reihe der Verbindungen ist die Nachauflaufwirkung besonders ausgeprägt. Diese Mittel entwickeln eine starke Kontaktwirkung auf die Blätter etablierter Unkräuter.The effect of the phenyl carbamates according to the invention, im hereinafter referred to as O-carboxylic acid anilides, extends in the case of a large number of their representatives, both pre-emergence and post-emergence applications. At a A number of compounds is the post-emergence effect in particular pronounced. These agents develop a strong contact effect on the leaves of established weeds.
Es hat sich außerdem gezeigt, daß die Verbindungen in der Regel eine selektive herbizide Wirkung besitzen und beispielsweise im Wachauflauf in Erdnüssen und in wichtigen Kulturgräsern wie z.B. in Saat- und Pflanzreis, in Mais und in anderen Getreidearten eingesetzt werden können. Dabei ist es möglich, mit einigen der Verbindungen aus Kulturgrasarten Ungräser zu vernichten, was bereits mitIt has also been shown that the compounds generally have a selective herbicidal action and for example in the casserole in peanuts and in important cultivated grasses such as in seed and plant rice, in maize and can be used in other grains. It is possible to do this with some of the connections Cultivated grass species weed to destroy what is already done with
009838/2282009838/2282
' A ' A
einer Aufwandmenge ab etwa 0,5 kg/ha Wirkstoff möglichan application rate of about 0.5 kg / ha active ingredient possible
In der oben gekennzeichneten allgemeinen Formel können die Symbole folgende Bedeutung haben:In the general formula marked above, you can the symbols have the following meanings:
Pur R-, und/oder R2 als aromatische Kohlenwasserstoffreste, z.B. Phenyl, α-Naphthyl, ß-Naphthyl u.a.,Pur R and / or R 2 as aromatic hydrocarbon radicals, e.g. phenyl, α-naphthyl, ß-naphthyl, etc.,
als aliphatische Kohlenwasserstoffreste z.B. solche mit 1 bis 12 Kohlenstoffatomen, wie Methyl, Äthyl usw. bis Dodecyl, Isopropyl, Isooctyl, tert. Butyl, 2,2-Dimethylpropyl, Allyl u.a.,as aliphatic hydrocarbon radicals, for example, those having 1 to 12 carbon atoms, such as methyl, ethyl, etc. to Dodecyl, isopropyl, isooctyl, tert. Butyl, 2,2-dimethylpropyl, Allyl et al.,
als cycloaliphatische Kohlenwasserstoffreste z.B. solche mit 3 bis 8 Kohlenstoffatomen, wie Cyclopropyl usw. bis Gyclooctyl, als araliphatische Kohlenwasserstoffreste z.B. Benzyl, Phenyläthyl, Phenylpropyl u.a.as cycloaliphatic hydrocarbon radicals, for example, those with 3 to 8 carbon atoms, such as cyclopropyl, etc. to Gyclooctyl, as araliphatic hydrocarbon radicals e.g. benzyl, phenylethyl, phenylpropyl and others
Substituienten für diese Reste sind gegebenenfalls z.B. Alicylreste mit Ibis 4 Kohlenstoffatomen, wie Methyl, A'thyl u.a., Halogenatome, wie Fluor, Chlor, Brom und Jod, niedere Alkoxyreste, wie Methoxy, Äthoxy,.Propoxy und Butoxy u.a., niedere Alkylmercaptoreste, wie Methylraercapto „und Äthylmercapto u.a., und die Uitrogruppe, wobei die Reste gegebenenfalls ein- oder mehrfach gleich oder verschieden substituiert sein können.Substituents for these radicals are optionally e.g. Alicyl radicals with ibis 4 carbon atoms, such as methyl, Ethyl inter alia, halogen atoms such as fluorine, chlorine, bromine and iodine, lower alkoxy radicals such as methoxy, ethoxy, propoxy and Butoxy et al., Lower alkyl mercapto radicals such as methylraercapto "And Ethylmercapto et al., And the Uitro group, where the radicals can optionally be substituted one or more times, identically or differently.
00983 8/22 8200983 8/22 82
13130431313043
R-, und Rp können gemeinsam mit dem Kohlenstoffatom einen aliphatischen 4 "bis 12 gliedrigen Ring bilden, wie z.B. Cyclobutyl usw. bis Cyclododecyl, der gegebenenfalls durch niedere Alkylreste, wie Methyl, Äthyl u.a., ein- oder mehrfach substituiert sein kann.R- and Rp together with the carbon atom can form an aliphatic 4 "to 12 membered ring, such as cyclobutyl etc. to cyclododecyl, which can optionally be substituted one or more times by lower alkyl radicals such as methyl, ethyl, etc.
R, kann bedeuten eine Gruppe der allgemeinen iOrmelR, can mean a group of the general iOrmel
/V/ V
in der die Reste gleich oder verschieden sind und folgende Bedeutung haben:in which the radicals are the same or different and have the following meanings:
Wasserstoff, aliphatische Kohlenwasserstoffreste mit 1 bis 18 Kohlenstoffatomen, wie Methyl usw. bis Octadecyl, Isopropyl, Isobutyl, Pentyl-(2), Pentyl~(3), 2,2-Dimethylpropyl, 2-Methylbutyl, 3-Methylbutyl, Hexyl-(2), Hexyl-(3), 2-Äthylhexyl, 4-Methylpentyl-(2), tert. Octyl, Allyl u.a., cycloaliphatische Kohlenwasserstoffreste mit 3 Ms 12 Kohlenstoffatomen, wie Cyclopropyl usw. bis Cyclododecyl, aromatische Kohlenwasserstoffreste, wie Phenyl, α-lTaphthyl, ß-Iiaphthyl u.a.Hydrogen, aliphatic hydrocarbon radicals with 1 to 18 carbon atoms, such as methyl etc. to octadecyl, isopropyl, isobutyl, pentyl- (2), pentyl ~ (3), 2,2-dimethylpropyl, 2-methylbutyl, 3-methylbutyl, hexyl- (2), hexyl- (3), 2-ethylhexyl, 4-methylpentyl- (2), tert. Octyl, allyl, etc., cycloaliphatic hydrocarbon radicals with 3 Ms 12 carbon atoms, such as cyclopropyl etc. to cyclododecyl, aromatic hydrocarbon radicals such as phenyl, α-l-taphthyl, β-iaphthyl et al.
Diese Reste können gegebenenfalls ein- oder mehrfach gleich oder verschieden substituiert sein, z.B. durch Halogenatome, wie ]?luor, Chlor, Brom, Jod, die üFitrogruppe, die Irifluormethyigruppe, Alkyl-, Alkoxy- oder Alkylmercaptoreste mit jeweils 1 bis 5 Kohlenstoffatomen.These radicals can optionally be substituted one or more times, identically or differently, for example by Halogen atoms, such as]? Luor, chlorine, bromine, iodine, the üFitro group, the irifluoromethyl group, alkyl, alkoxy or alkyl mercapto radicals each having 1 to 5 carbon atoms.
009838/2282009838/2282
R-, ' und Rp1 können weiterhin gemeinsam mit dem U-Atom einen gegebenenfalls weitere U- und/oder O-Atome enthaltenden heterocyclischen Ring, wie den Morpholin-, Piperidin- oder Pyirolidinring u.a., oder jeweils allein einen heterocyclischen Rest, wie den Pyridylrest u.a., darstellen und R-, ' kann außerdem für einen durch einen heterocyclischen Rest substituierten aliphatischen Kohlenwasserstoffrest stehen, wie z.B. Furfuryl u.a.R, 'and Rp 1 together with the U atom can furthermore contain a heterocyclic ring, optionally containing further U and / or O atoms, such as the morpholine, piperidine or pyirolidine ring, among others, or in each case alone a heterocyclic radical, such as the Pyridyl radical, inter alia, and R-, 'can also stand for an aliphatic hydrocarbon radical substituted by a heterocyclic radical, such as furfuryl and others
R, kann ferner bedeuten einen aromatischen Kohlenwasserstoffrest, wie Phenyl, α-ITaphthyl, ß-liaphthyl u.a., einen aliphatischen Kohlenwasserstoffrest mit 1 bis 18 Kohlenstoffatomen, wie Methyl usw. bis Octadecyl, Isopropyl, Isobutyl, Pentyl-(2), Hexyl-(2), tert. Octyl, Allyl u.a., einen cycloaliphatischen Kohlenwasserstoffrest mit 4 bis 10 Kohlenstoffatomen, wie Cyclobutyl usw. bis Cyclodecyl u.a., einen araliphatischen Kohlenwasserstoffrest, wie z.B. Benzyl, Phejiyläthyl u.a., eine Alkoxygruppe mit 1 bis 18 Kohlenstoffatomen, wie Methoxy, Äthoxy u.a., eine Aryloxygruppe, wie Phenoxy, Fapthoxy u.a., wobei die Kohlenwasserstoffreste gegebenenfalls ein- oder mehrfach gleich oder verschieden substituiert sein können, z.B. durch Halogenatome, wie Fluor, Chlor, Brom, Jod, niedere Alkylreste, wie Methyl, Äthyl u.a., niedere Alkoxyreste, wie Methoxy, Ä'thoxy u.a., niedere Alkylmercaptoreste, wie Methylmercapto u.a., und die Nitrogruppe u.a.R, can also mean an aromatic hydrocarbon radical, such as phenyl, α-ITaphthyl, β-liaphthyl and others, a aliphatic hydrocarbon radical with 1 to 18 carbon atoms, such as methyl etc. to octadecyl, isopropyl, Isobutyl, pentyl- (2), hexyl- (2), tert. Octyl, allyl, etc., a cycloaliphatic hydrocarbon radical with 4 to 10 carbon atoms, such as cyclobutyl etc. to cyclodecyl etc., an araliphatic hydrocarbon radical, such as benzyl, phenylethyl, etc., an alkoxy group having 1 to 18 carbon atoms such as methoxy, ethoxy and others, an aryloxy group such as phenoxy, fapthoxy and others, where the hydrocarbon radicals can optionally be substituted one or more times, identically or differently, e.g. by halogen atoms such as fluorine, chlorine, bromine, iodine, lower alkyl radicals such as methyl, ethyl, etc., lower Alkoxy radicals, such as methoxy, ethoxy, etc., lower alkyl mercapto radicals, such as methylmercapto et al., and the nitro group et al.
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Außerdem kann R, den RestIn addition, R, the rest
-0-N-0-N
darstellen, in dem IL" und Rp" gleich oder verschieden sind und die gleiche Bedeutung haben wie unter R-, und/oder Rp beschrieben.represent, in which IL " and Rp" are identical or different and have the same meaning as described under R- and / or Rp.
Pur R. und R5 kommen in Betracht Wasserstoff und aliphatische Kohlenwasserstoffreste mit 1 bis 4 Kohlenstoffatomen, wie Methyl, Äthyl u.a.Pur R. and R 5 are hydrogen and aliphatic hydrocarbon radicals with 1 to 4 carbon atoms, such as methyl, ethyl and others
Als besonders geeignete Wirkstoffe sind die substituierten Carbamoyloxyderivate der Oximinoalkan-0-carbonsäureanilide zu nennen.Substituted active ingredients are particularly suitable Carbamoyloxy derivatives of the oximinoalkane-0-carboxylic acid anilides to call.
Die bisher nicht bekannten Verbindungen können z.B. nach folgendem Verfahren hergestellt werden:The previously unknown compounds can be produced, for example, using the following process:
Durch Umsetzung von Verbindungen der allgemeinen Formel:By implementing compounds of the general formula:
OH oder gegebenenfalls deren SalsenOH or possibly their salsen
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■ P. 1126.Q0/jQr,Lie/Ei■ P. 1126.Q0 / j Qr, Lie / Ei
ä) mit Isocyanatan der allgemeinen Formelä) with isocyanatane of the general formula
1 ^>ΐί = c = ο : ■.·'"..■-■:"■-■ j -- " 1 ^> ΐί = c = ο : ■. · '".. ■ - ■:" ■ - ■ j - "
ν ■ ■ .·■ ; νν ■ ■. · ■ ; ν
zweckmäßigerweise in einem organischen Lösungsmittel, wie ' z.B. Aceton, Methylisobuty !keton, !Tetrahydrofuran oder Dioxan, und gegebenenfalls unter Zusats eines Katalysators? zweckmäßig einer tertiären organischen Base, z.B« !Triethylamin, oder einer organischen Zinnverbindung, S9B. Di-n-butyl-zinndilaurat, oderexpediently in an organic solvent, such as, for example, acetone, methyl isobutyl ketone, tetrahydrofuran or dioxane, and optionally with the addition of a catalyst ? expediently a tertiary organic base, for example triethylamine, or an organic tin compound, S 9 B. di-n-butyltin dilaurate, or
b) mit Halogeniden der allgemeinen SOrmelnb) with halides of the general formulas
H - 0Ϊ - HaI9 oderH - 0Ϊ - HaI 9 or
E "E "
1^ C = Ii - 0-CY - Hai, oder E " 1 ^ C = Ii - 0-CY - shark, or E "
E5-CY-HaI \ : VE 5 -CY-HaI \: V
vorzugsweise unter Zusatz einer anorganischen Base, ζ·Ββ NapCO- oder KpCO5, oder einer tertiären organischen Base, z.B. Triäthylamins, Pyridin, Dimethyl- oder Diäthylanilin, wobei es jeweils auch möglieh ist, zunächst die entsprechenden Salze starker Basen herzustellen und diese anschließend vorzugsweise in einem organischen Lösungsmittelj, z.B. Acetonitril oder MethylisobutylketoHj. mit dem ■preferably with the addition of an inorganic base, NapCO- or KpCO 5 , or a tertiary organic base, for example triethylamine, pyridine, dimethylaniline or diethylaniline, whereby it is also possible in each case to first prepare the corresponding salts of strong bases and then preferably in an organic solvent, for example acetonitrile or methyl isobutylketoH. with the ■
betreffenden Halogenid umzusetzen, oderto implement the halide concerned, or
c) mit Phosgen oder !Thiophosgen, zweckmäßigerweise unter Verwendung eines organischen Lösungsmittels, z«B» Essigester, Setrahydrofuranj Methylenchlorid, Äthylenchlorid oder Eetrashlor»c) with phosgene or! thiophosgene, expediently using an organic solvent, eg "B" ethyl acetate, setrahydrofuranj Methylene chloride, ethylene chloride or eetrashlor »
0098387228200983872282
■ -^V '· . 1913043 kohlenstoff, unter Zusatz eines säure bind enden Mittels,■ - ^ V '·. 1913043 carbon, with the addition of an acid binding agent,
■ z.B. der unter b) genannten Basen, und anschließende Umsetzung mit einem Amin der allgemeinen Formel y^l oder einem■ For example, the bases mentioned under b), and subsequent reaction with an amine of the general formula y ^ l or a
HEiHEi
Alkohol oder einem Phenol der allgemeinen Formel HO-R,,, oder einem Öxim der allgemeinen Formel HO-H-=O gegebenenfallsAlcohol or a phenol of the general formula HO-R ,,, or an Öxim of the general formula HO-H - = O, if appropriate
unter Zusatz einer der unter b) genannten Basen, wobei E5, R., R5, Ε™*, E2*, Rn", R2 11 und X die oben angegebene Bedeutung haben und Hai ein Halogenatom, insbesondere ein Chloratom darstellt.with the addition of one of the bases mentioned under b), where E 5 , R., R 5 , Ε ™ *, E 2 *, Rn ", R 2 11 and X have the meaning given above and Hal represents a halogen atom, in particular a chlorine atom .
Im folgenden wird die Herstellung der neuen Phenylcarbamate erläutert:The following is the preparation of the new phenyl carbamates explained:
a) 2-0ximinopropan-Q-carbonaäure-3'-(N-methylcarbamoyloxy)-anilid a) 2-oximinopropane-Q-carboxylic acid 3 '- (N-methylcarbamoyloxy) anilide
20,8 g (0,1 Mol) 2-0ximinopropan-0-carbonsäure-31-hydroxyanilid
werden in 100 ml !Tetrahydrofuran aufgenommen und mit
0,5 ml Triäthylamin und 6,2 ml Methylisocyanat versetzt. Nach 15 Std. bei Raumtemperatur wird das gebildete Carbamat
durch Zugabe von Pentan gefällt.
Ausbeute: 25,5 g = 96,3$ der !Cheorie F. 133 - 1340C20.8 g (0.1 mol) of 2-oximinopropane-0-carboxylic acid-3 1 -hydroxyanilide are taken up in 100 ml of tetrahydrofuran, and 0.5 ml of triethylamine and 6.2 ml of methyl isocyanate are added. After 15 hours at room temperature, the carbamate formed is precipitated by adding pentane.
Yield: 25.5 g = 96.3 $ of Cheorie F. 133-134 0 C!
b) 2-Oxiininopropan-0-carbonsäure-3-(lf-3!if-'pentamethylencarbamoyloxy)-anilid b) 2-Oxininopropane-0-carboxylic acid 3- (lf-3! i f-pentamethylene carbamoyloxy) anilide
Das aus 16,7 g (0,08 Mol) 2-Oximinopropan-O-carbonsäure-3t-hydroxyanilid mit ETaOH in Methanol hergestellteThat prepared from 16.7 g (0.08 mol) of 2-oximinopropane-O-carboxylic acid-3 t -hydroxyanilide with ETaOH in methanol
009838/2282009838/2282
■ 1813043■ 1813043
Ha-SaIz wird nach Trocknung in 50 ml Acetonitril auf-* · genommen. Unter Rühren werden bei ca, 15°0 13,0 g (0,88 Mol) Piperidin-H-carbonsäurechlorid eingetropft. 1 Stunde wird bei Raumtemperatur nachgerührt, dann filtriert, in Vakuum eingedampft, der Rückstand mit 200 ml Äther versetzt und das Garbamat abgesaugt. Ausbeute: 15,1 g = 59,4$ der Theorie P. 118-119QCAfter drying, Ha-SaIz is taken up in 50 ml of acetonitrile. 13.0 g (0.88 mol) of piperidine-H-carboxylic acid chloride are added dropwise at about 15 ° C. with stirring. The mixture is stirred at room temperature for 1 hour, then filtered, evaporated in vacuo, 200 ml of ether are added to the residue and the garbamate is filtered off with suction. Yield: 15.1 g = 59.4 $ of theory P. 118-119 Q C
c) 3-0ximinopentan-0-carbonsäure-3'- (äthoxycarbonyloxy )'-. anilid c) 3-0ximinopentane-0-carboxylic acid-3'- (ethoxycarbonyloxy) '-. anilide
23,6 g (0,1 Mol) 3-Oximinopentan-0-carbonsäure-3fhydroxyanilid werden in 5 0 ml Pyridin aufgenommen und nach Zugabe von 13,0 g Ghlorameisensäureäthylester 1 Stunde auf dem Dampfbad erhitzt. Dann wird im Vakuum eingedampft, der Rückstand in Äther/Eiswasser aufgenommen und die organische Phase der Reihe nach gewaschen mit verdünnter Salzsäure, Eiswasser, kalter KpCO^-Lösung und Eiswasser. Hach dem Trocknen mit MgSO- wird eingedampft und im Vakuum getrocknet. . Ausbeute? 23 g = .75$ der Theorie n-p20 « 1,533223.6 g (0.1 mol) of 3-oximinopentane-0-carboxylic acid-3 f hydroxyanilide are taken up in 50 ml of pyridine and, after addition of 13.0 g of ethyl chloroformate, heated on the steam bath for 1 hour. It is then evaporated in vacuo, the residue taken up in ether / ice water and the organic phase washed in sequence with dilute hydrochloric acid, ice water, cold KpCO ^ solution and ice water. After drying with MgSO- is evaporated and dried in vacuo. . Yield? 23 g = .75 $ of the theory np 20 «1.5332
In der folgenden Tabelle sind erfindungsgemäße Verbindungen aufgeführts - - .The following table lists compounds according to the invention - -.
Verbin- Harne der Verbindung PhysikalischeConn- ures the connection physical
dung Konstantedung constant
Hr. - ■ \Mr. - ■ \
2-0ximinopropan-0-carbonsäure-4t- Ϊ. = 109 - 1110C'2-0ximinopropane-0-carboxylic acid-4 t - Ϊ. = 109 - 111 0 C '
(H-methylcarbamoyloxy)-anilid 2-0ximinopropan-0-carbonsäure-4f- J1*. = 113 - 1150G(H-methylcarbamoyloxy) -anilide 2-oximinopropane-0-carboxylic acid-4 f - J 1 *. = 113-115 0 G
(H-äthylcarbamoyloxy)-anilid(H-ethylcarbamoyloxy) anilide
009838/2282009838/2282
- Ii -- Ii -
dung
Nr.Connect
manure
No.
Hiysilcaliscne
Konstante1913043
Hiysilcaliscne
constant
(N-propylcarbamoyloxy)-anilid2 * -oximinopropane-0-carboxylic acid-4 '-
(N-propylcarbamoyloxy) anilide
(N-isopropylcarbamoyloxy)-anilid2-Oxiniinopropa2i-Ö-oarboxylic acid-4 '-
(N-isopropylcarbamoyloxy) anilide
(N-n-butyl0arbamöyloxy)-anilid2-oximinopropane-0-carboxylic acid-4'-
(Nn-butyl carbamoyloxy) anilide
aiiilid ι πΓμ19 ** ^ β ^ ββ ^^ & Ι ^^ Γ j I ^ I ^ i ^ TlXf 1 ϊ «^^ ßL * 8 ^ i ^ flWi rt ^ lfi I ^^ T'V * I * ■
aiiilid
(N-methylcarbamoyloxy}-anilid2-0ximinQpröpan-ö-carboxylic acid-3'-
(N-methylcarbamoyloxy} anilide
(N-äthylcarbamoyloxy)-anilid2-0ximinopropane-6-carboxylic acid-3 V-.
(N-ethylcarbamoyloxy) anilide
(N-ühenylcarbamoyloxy)-anilid2-0ximinopa? Opane-0-carboxylic acid-3 -
(N-phenylcarbamoyloxy) anilide
2-0ximinopropan«0~carbonsäure-3'- Q 2-oximinopropane «0 ~ carboxylic acid 3'- Q
CN-i8opropylcarbamoyloxy)-anilid P. a 134 - 135 0CN-18opropylcarbamoyloxy) anilide P. a 134-135 0
g-Öximinopropan-O-carbonsäure-S*- o g-Oximinopropane-O-carboxylic acid-S * - o
(N-tert.-butylcarbaaioyloxy)-anilid F. * 133 - 134 C(N-tert-butylcarbaaioyloxy) anilide F. * 133-134 C
2-Oximinop3?o|tan-0-carbonsäure-3l-2-Oximinop3? O | tan-0-carboxylic acid-3 l -
(N-n-octylcarbamoylöxyJ-attilid Pe = 101 - 102uC(Nn-octylcarbamoylöxyJ-attilid P e = 101-102 C u
2-.0adLiainoi)ropan-0-carbohsäure-3f- ' n 2-.0adLiainoi) ropan-0-carboic acid-3 f - ' n
(H«allylearbamoyloxy)-anilid P. = 121 - 122°C(H «allylearbamoyloxy) anilide P. = 121-122 ° C
2-0xiiainopyopaii-ö-oarbonsämre-5f-2-0xiiainopyopaii-ö-oarbonsämre-5 f -
(N{3l!tMIll)il(N {3 l! TMIll) il
({3ypy)yy) _({3ypy) yy) _
anilid P. = 152 - 1530Canilide P. = 152-153 0 C
2-Oxiffiinopropan-O-carbonsäure-3f-2-oxiffiinopropane-O-carboxylic acid-3 f -
CH-(48l-mei;hylplienyl)-öarbaiaoyloxy)- n CH- (4 8l -mei; hylplienyl) -öarbaiaoyloxy) - n
anilia- P. ».140 - 1410O anilia- P. ». 140 - 141 0 O
If 2If 2
C(3y)yy)C (3y) yy)
anilid P* = 148 - 1490Oanilide P * = 148 - 149 0 O
^-öximinopröpan-Ö-carbonsäure^'-^ -öximinopröpan-Ö-carboxylic acid ^ '-
(ii<-(4uchlorphenyl)»carbamoyloxy)- _(ii <- (4 u chlorophenyl) »carbamoyloxy) - _
· P. = 129 - 13O0C· P. = 129 - 13O 0 C
0098387128200983871282
- 12 -- 12 -
Verbin- Name der Verbindung . . _ n , o Physikalische dung 1 91 3 U 4 ο KonstanteConnection name of the connection. . _ n , o physical education 1 91 3 U 4 ο constant
·. 2-0ximinopropan-0-carbonsäure-3l-·. 2-0ximinopropane-0-carboxylic acid-3 l -
(N(3"-chlor-4"-methylphenyl)- 0 (N (3 "-chloro-4" -methylphenyl) - 0
carbamoyloxy)-anilid *P, =145 - 146 p ^ carbamoyloxy) anilide * P, = 145 - 146 p ^
2-0ximinopropan-0-carbonsäure-3l-2-0ximinopropane-0-carboxylic acid-3 l -
(N-(3"-trifluormethy!phenyl)- ο*(N- (3 "-trifluoromethy! Phenyl) - ο *
carbamoyloxy)-anilid ί1· =159 - 160 0 ·carbamoyloxy) anilide ί 1 = 159 - 160 0
2-0ximinopropan-0-carbonsäure-3t- on2-0ximinopropane-0-carboxylic acid-3 t -one
(N-methyl-N-phenylcarbamoyloxy)- 33^ =1,5760 anilid · -(N-methyl-N-phenylcarbamoyloxy) - 33 ^ = 1.5760 anilide -
2-0ximinopropan-0-carbonsäure-3l-2-0ximinopropane-0-carboxylic acid-3 l -
(N-furfurylcarbsmoyloxy)-anilid P* »' 88- 89 0(N-furfurylcarbsmoyloxy) anilide P * »'88- 89 0
· 2-Oximinopropan-0-carbonsäure-3'~ o · 2-Oximinopropane-O-carboxylic acid-3 '~ o
(morpholino-li-carbonyloxy)-anilid F# = 160 »161 0(morpholino-li-carbonyloxy) anilide F # = 160 »161 0
2-0ximinopropan-0-carbonsäure-31- o 2-0ximinopropane-0-carboxylic acid-3 1 - o
(li-sek.-butylcarbamoyloxyj-anilid .P. =125 - 126°G(li-sec.-butylcarbamoyloxyj-anilide .P. = 125 - 126 ° G
'25 3-Oximinopentan-O-carbonsäure~3l-'25 3-Oximinopentane-O-carboxylic acid ~ 3 l -
(Ii-methylcarbamoyloxy)-anilid i1, =115 - 116 C(II-methylcarbamoyloxy) -anilide i 1 , = 115-116C
3-Oximinopentan-0-carbonsäure-3l-3-oximinopentane-0-carboxylic acid-3 l -
(N-äthylcarbamoyloxy)-anilid Pe = 81 - 02 0(N-ethylcarbamoyloxy) anilide P e = 81-02 0
3-Oximiriopentan-0-earbonßäure-3'- ■3-oximiriopentane-0-earbonic acid-3'- ■
(N-n-propylcarbamoyloxy)-anilid P. = 78 - ■ 80 C(N-n-propylcarbamoyloxy) anilide P. = 78 - ■ 80 C
3-Oximinopentan-0-carbonsäure-3l- ο3-oximinopentane-0-carboxylic acid-3 l - ο
(B"-isopropylcarbamoyloxy)-anilid P· = 113 - 114 G(B "-isopropylcarbamoyloxy) anilide P · = 113-114 G
3-Oximinopentan-0-carbonsäure-31-* -_■"■"3-Oximinopentane-0-carboxylic acid-3 1 - * -_ ■ "■"
(li-n-butylcarbamoyloxy)-anilid P. = 71- 72 0(li-n-butylcarbamoyloxy) anilide P. = 71-720
3-Oximinopentan-0-carbonsäure-31- o 3-Oximinopentane-0-carboxylic acid-3 1 - o
(iT-sek.-butylcarbamoyloxy)-anilid P» = 109 - 111 O(iT-sec-butylcarbamoyloxy) anilide P »= 109-111 O
3-Oximinopentan-0-carbonsäure-3s~ o 3-Oximinopentane-0-carboxylic acid-3 see above
(N-tert.-butylcarbainoyloxy)-anilid P· =79 - 80 C . S-Oximinopentan-O-earbonsäure-ü'- -(N-tert-butylcarbainoyloxy) anilide P = 79-80 C . S-Oximinopentane-O-carboxylic acid-ü'- -
(K-n-oetylcarbamoyloxy)-(K-n-oetylcarbamoyloxy) -
anilid P, = 47 - 48 C ·anilide P, = 47 - 48 C
3-Oximinopentan-0-earbonsäure-31- .3-oximinopentane-0-carboxylic acid-3 1 -.
(N-2", 2"-dimethylpropylcarba-(N-2 ", 2" -dimethylpropylcarba-
moyloxy)-anilid P. » 93 - 940C ·moyloxy) -anilide P. »93 - 94 0 C ·
- 13' 009838/2282 - 13 ' 009838/2282
Verbin-* Name der Verbindung PhysikalischeConnection- * Name of the connection physical
dung Konstantedung constant
3-Oximinopentan-Q-carbonsäure-3'- ?0 3-Oximinopentane-Q-carboxylic acid-3'- ? 0
(N-(2"-äthylhexyl)-carbamoyloxy)- ngw = 1,5210 aniiid(N- (2 "-ethylhexyl) -carbamoyloxy) - ng w = 1.5210 aniiid
3-0ximinopeni;an-0-carbonsäure-3I- o 3-0ximinopeni; an-0-carboxylic acid-3 I - o
■ (N-allylcarbamoyloxy)-aniiid P. = 82 - 83 C■ (N-allylcarbamoyloxy) -aniiid P. = 82-83 C
3-Oximinopentan-0-carbonsäure-3I- „203-Oximinopentane-0-carboxylic acid-3 I - "20
(N,N-diäthylcarbamoyloxy)-anilid 11D = 1,5410(N, N-diethylcarbamoyloxy) anilide 11 D = 1.5410
3-Oximinopentan-0-car'bonsäure-3l- „ ft 3-oximinopentane-0-carboxylic acid-3 l - " ft
(N-cyclohexylcarbamQyloxyJ-anilid P. = 128 - 129 0(N-cyclohexylcarbamQyloxyJ-anilide P. = 128 - 129 0
3-Oximinopentan-0-car'bonsäure-3l- Q 3-Oximinopentane-0-carboxylic acid-3 l - Q
(n-phenyloarbamoyloxy)-anilid P.. = 127 - 128 G(n-phenyloarbamoyloxy) anilide P .. = 127 - 128 G
3-Oximinopentan-0-car'bonsäure-3t-3-oximinopentane-0-carboxylic acid-3 t -
(H'-(3ll-me-t;hylphenyl)-carlDamoyloxy)- Λ (H '- (3 ll -me-t; hylphenyl) -carlDamoyloxy) - Λ
aniiid P. = 110 - 1110Caniiid P. = 110-111 0 C.
3-0ximinopentan-0-carbonsäure-3l-3-0ximinopentane-0-carboxylic acid-3 l -
(N-(4"-methylphenyl)-carbamoyloxy)- n (N- (4 "-methylphenyl) -carbamoyloxy) - n
aniiid . P. « 133 - 1340Caniiid. P. "133-134 0 C
3-Oximinopen1;an-Q-carbonsäure-31-3-Oximinopen1; an-Q-carboxylic acid-3 1 -
(K- (2 " ■-, 4 " -dim ethy !phenyl) -carba-(K- (2 "■ -, 4" -dim ethy! Phenyl) -carba-
moyloxy)-aniiid P. « 132 - 133WCmoyloxy) -aniiid P. "132-133 W C
3-0ximinopentan-0-carbonsäure-3 *-3-0ximinopentane-0-carboxylic acid-3 * -
(U-(3", 4M-dlchlorphenyl)-carba-(U- (3 ", 4 M -dlchlorphenyl) -carba-
moyloxy)-aniiid F. = 138 - 139 Cmoyloxy) -aniiid F. = 138-139 C
3-0ximinopen1;an-0-carbonsäure-3t-3-0ximinopen1; an-0-carboxylic acid-3 t -
(¥-(2», 6"-dimethylphenyl)- "(¥ - (2 », 6" -dimethylphenyl) - "
carbamoyloxy)-anilid P. = 124 - 126ÜCcarbamoyloxy) -anilide P. = 124-126 C Ü
3~0ximinopentan-0-carbonsäure-3l-3 ~ 0ximinopentane-0-carboxylic acid-3 l -
(F-(3"-chlorphenyl)-carbamoyloxy)-(F- (3 "-chlorophenyl) -carbamoyloxy) -
aniiid . F. = 115 - 116 Caniiid. F. = 115-116 C.
3-Oximinopentan-0-carbonsäure-3t-3-oximinopentane-0-carboxylic acid-3 t -
(N- (4ll-chlQrphenyl)-carbamoyloxy )-(N- (4 ll -chlQrphenyl) -carbamoyloxy) -
aniiid P, = 107 - 1080Caniiid P = 107-108 0 C.
3"*Oximinopentan-0~carbonsäure-3l-3 "* Oximinopentane-0 ~ carboxylic acid-3 l -
(N-(3»-chlor-4II-methylphenyl)-(N- (3 »-chlor-4 II -methylphenyl) -
carbamoyloxy)-anilid P# - 120 - 121°Ccarbamoyloxy) anilide P # - 120 - 121 ° C
,47 3-Oximinopentan-Q~carbonsäure-3I- po, 47 3-Oximinopentane-Q ~ carboxylic acid-3 I - po
(NjN-pentametnylencärbamoyloxy)- ηΏ = 1,5466 aniiid ""(NjN-pentametnylencarbamoyloxy) - η Ώ = 1.5466 aniiid ""
83 8/2252 - 14 -83 8/2252 - 14 -
Verbin- Name der Verbindung PhysikalischeConnection- Name of the connection physical
- dung Konstante- dung constant
Nr.No.
3-Oximinopentan-0-carbonsäure-3'-3-oximinopentane-0-carboxylic acid-3'-
(N-methyl-N-phenylcarbamoyloxy)- ni = 1,5760 anilid(N-methyl-N-phenylcarbamoyloxy) - ni = 1.5760 anilide
4-0ximino-2-methylpentan-0-carbon-4-0ximino-2-methylpentane-0-carbon-
säure-3'-(N-methylcarbamoyloxy)-acid-3 '- (N-methylcarbamoyloxy) -
anilid P. = 114 - 115anilide P. = 114-115
2-Oximino-n-undecan-O-carbonsäure-2-oximino-n-undecane-O-carboxylic acid
3'-(N-n-propylcarbamoyloxy)-3 '- (N-n-propylcarbamoyloxy) -
anilid · Harzanilide resin
2-0ximino-undecan-0-carbonsäure-3f—2-0ximino-undecane-0-carboxylic acid-3 f -
(N-allylcarbamoyloxy)-anilid P. = 61 - 62 C(N-allylcarbamoyloxy) anilide P. = 61-62 C
^ 52 l-Oximino-3,3>5-trimethylcyclohexen-P (5)-0-carbonsäure-3'-(N-n-butyl-^ 52 l-oximino-3,3> 5-trimethylcyclohexene-P (5) -0-carboxylic acid-3 '- (N-n-butyl-
carbamoyloxy)-anilid P· = 145carbamoyloxy) anilide P = 145
l-0ximino-3,3,5-trimethylcyclohexen-l-oximino-3,3,5-trimethylcyclohexene
(5)-O-carbonsäure-3'-(N-cyclohexylcarbamoyloxy)-anilid P. = 139 C 2-0ximino-n-undecan-0-carbonsäure-(5) -O-carboxylic acid 3 '- (N-cyclohexylcarbamoyloxy) anilide P. = 139 C 2-0ximino-n-undecane-0-carboxylic acid
3'-(N-n-butylcarbamoyloxy)-anilid P. = 78 - 79 2-0ximinopropan-0-carbonsäure-3'-3 '- (N-n-butylcarbamoyloxy) -anilide P. = 78-79 2-0ximinopropane-0-carboxylic acid-3'-
(N-n-hexylcarbamoyloxy)-anilid 2-0ximinopropan-0-carbonsäure-3'-(N-n-hexylcarbamoyloxy) anilide 2-0ximinopropane-0-carboxylic acid-3'-
(N-isobutylcarbamoyloxy)-aniiid 3-Oximinopentan-0-carbonsäure-3'-(N-isobutylcarbamoyloxy) -aniiid 3-oximinopentane-0-carboxylic acid-3'-
(N- (3"-methoxyphenyl)-carbamoyloxy)-λ anilid(N- (3 "-methoxyphenyl) -carbamoyloxy) -λ anilide
2-0xiiainopropan-0-carbonsäure-3 ' —2-0xiiainopropane-0-carboxylic acid-3 '-
(N, N-pentamethylencarbamoyloxy )·- anilid(N, N-pentamethylene carbamoyloxy) - anilide
2-Oximino-n-undecan-O-carbonsäure-2-oximino-n-undecane-O-carboxylic acid
3'-(N-äthylcarbamoyloxy)-anilid 2-0ximinopropan-0-carbonsäure-3'-3 '- (N-ethylcarbamoyloxy) anilide 2-0ximinopropane-0-carboxylic acid-3'-
(N-n-propylcarbamoyloxy)-anilid 2-0ximinopropan-0-carbonsäure-3'-(N-n-propylcarbamoyloxy) anilide 2-0ximinopropane-0-carboxylic acid-3'-
(N-cyclohexylcarbamoyloxyJ-anilid P. = 129 - 130 C(N-cyclohexylcarbamoyloxyJ-anilide P. = 129 - 130 C
009838/2282009838/2282
P. 1126.00/Pr.Lie/RiP. 1126.00 / Pr.Lie / Ri
Verbin- Name der Verbindung PhysikalischeConnection- Name of the connection physical
dung Konstantedung constant
62 2-Oximinopropan-0-carbonsäure-3'-62 2-oximinopropane-0-carboxylic acid-3'-
(N-(3"»4M-dichlorphenylJ-carbamoyl-(N- (3 "» 4 M -dichlorophenylJ-carbamoyl-
oxyj-anilid F. a 164 - 165 Coxyj-anilide F. a 164-165 C
63 2-0ximinopropan-0-carbonsäure-31--63 2-oximinopropane-0-carboxylic acid-3 1 -
(2",5"-dichlorphenyl)-earbamoyloxy)-(2 ", 5" -dichlorophenyl) -earbamoyloxy) -
anilid F. « 136 - 1370Canilide F. "136 to 137 0 C
64 2-Oximinopropan-0-carbonsäure-3'-64 2-oximinopropane-0-carboxylic acid-3'-
(N-neopentylcarbamoyloxy)-anilid(N-neopentylcarbamoyloxy) anilide
65 2-0ximinopröpan-0-carbonsäure-3 *-65 2-0ximinoproepane-0-carboxylic acid-3 * -
{N-n-butyloarbamoylöxy)-anilid{N- n -butyloarbamoyl oxy) anilide
66 2-Oximinopropan-0-carbonsäure-3f-66 2-oximinopropane-0-carboxylic acid-3 f -
(N-a-naphthylcarbamoyloxy)-anilid(N-α-naphthylcarbamoyloxy) anilide
67 2-0ximinopropan-0-carbonsäure-3'-67 2-0ximinopropane-0-carboxylic acid-3'-
(N-pentyl-t2)-carbamoyloxy)-anilid(N-pentyl-t2) carbamoyloxy) anilide
68 S-Oximinopentan-O-carbonsäure^'-68 S-Oximinopentane-O-carboxylic acid ^ '-
(N,N-dimethylcarbamoyloxy)-anilid(N, N-dimethylcarbamoyloxy) anilide
69 2-0ximinopropan-0-carbonsäure-3'-69 2-0ximinopropane-0-carboxylic acid-3'-
(N-(3"-sethoxyphenyl)-carbamoyloxy)«(N- (3 "-sethoxyphenyl) -carbamoyloxy)«
anilid F. = 133 - 1340Oanilide F. = 133-134 0 O
p 2np 2 n
isopropylidenamino-oxycarbonyloxy- nt = 1,5277 anilid ■"isopropylideneamino-oxycarbonyloxy- nt = 1.5277 anilide ■ "
71 J-Oxirainopentan-O-carbonsäure-S *-71 J-Oxirainopentane-O-carboxylic acid-S * -
( N- ( 2 ", 5 " -»dimethylplienyl) -c arbamoyl-(N- (2 ", 5" - »dimethylplienyl) -carbamoyl-
oxy)-anilid F.*= 90- 920Coxy) -anilide F. * = 90-92 0 C
72 J-Oximinopentan-O-carbonsäure^1-72 J-Oximinopentane-O-carboxylic acid ^ 1 -
*(N-n-hexylcarbamoyloxy)-anilid P. = 48 - 50 C* (N-n-hexylcarbamoyloxy) -anilide P. = 48-50 C.
73 3-0ximino-2-methylbutan-0-carbon-73 3-0ximino-2-methylbutane-0-carbon-
8äure-3'-(N~äthylcarbamoyloiy)-8-acid-3 '- (N ~ ethylcarbamoyloiy) -
anilid F. = 114 - 1160Canilide mp = 114-116 0 C.
74 3-0ximino-2~methylbutan-0-carbon-74 3-0ximino-2 ~ methylbutane-0-carbon-
säure-3'-(N~( 3"-chlorplienyl )-acid-3 '- (N ~ (3 "-chlorplienyl) -
carbamoyloxy)-anilid F. = 125 - 1270Ccarbamoyloxy) anilide mp = 125-127 0 C.
75 3-0ximino-2-methylbutan-0-carbon-75 3-0ximino-2-methylbutane-0-carbon-
Bäure-3'-(N-Cp-chlorphenyl)-Acid-3 '- (N-Cp-chlorophenyl) -
carbamoyloxyj-anilid F, = 128 - 130 Ccarbamoyloxyj-anilide F, = 128-130 C
- 16 -- 16 -
ie - ie -
P, 1126.00/Dr.3ae/RiP, 1126.00 / Dr.3ae / Ri
Verbindung Nr.Connection no.
Uame. der Verbindung Physikalische KonstanteUame. the connection physical constant
3-Oximino-2-methylbutan-O-carbonsäure-3'-(N-cyclohexylcarbamoyloxy)-anilid 3-Oximino-2-methylbutane-O-carboxylic acid 3 '- (N-cyclohexylcarbamoyloxy) anilide
3-0ximino-2-methylbutan-O-carbonsäure-3'-(K-(3"-methylphenyl)-carbamoyloxy)-aniIid 3-0ximino-2-methylbutane-O-carboxylic acid 3 '- (K- (3 "-methylphenyl) -carbamoyloxy) -aniIide
3-0ximino-2-methylbutan-O-cärbonsäure-3'-(N-phenylcarbamoyloxy)-anilid 3-0ximino-2-methylbutane-O-carboxylic acid 3 '- (N-phenylcarbamoyloxy) anilide
3-0ximino-2-methylbutan-O-carbonsäure-3'-(N-n-propylcarbamoyloxy)-anilid 3-0ximino-2-methylbutane-O-carboxylic acid 3 '- (N-n-propylcarbamoyloxy) anilide
3-0ximino-2-methylbutan-0-carbonsäure-3 l-(N-(3"-trifliiormethylphenyl)-carbamoyloxy)-anilid 3-0ximino-2-methylbutane-0-carboxylic acid-3 l - (N- (3 "-trifliiormethylphenyl) -carbamoyloxy) -anilide
2-0ximinopentan-0-carbonsäure-3'— ( Ml-is opropylcar bamoyloxy)-anilid2-0ximinopentane-0-carboxylic acid-3'- (Ml-is opropylcar bamoyloxy) anilide
2-0ximinopentan-0-carbonsäure-3l-(ΐί-methylcarbamoyloxy )-anilid2-0ximinopentane-0-carboxylic acid-3 l - (ΐί-methylcarbamoyloxy) -anilide
2-0ximinopentan-0-carbonsäure-3 *- (N-sek·-butylcarbamoyloxy)-anilid2-0ximinopentane-0-carboxylic acid 3 * - (N-sec · -butylcarbamoyloxy) -anilide
2-0ximinopentan-0-carbonsäure-3*- * (li-ß-chloräthylcarbamoyloxy )-anilid 2-0ximinopentane-0-carboxylic acid-3 * - * (li-ß-chloroethylcarbamoyloxy) anilide
0x1111^0211^1^^^^003^0^ säure-3'-(tt-allylcarbamoyloxy)-anilid ' F, = 114°C . «= 116°C0x1111 ^ 0211 ^ 1 ^^^^ 003 ^ 0 ^ acid 3 '- (tt-allylcarbamoyloxy) anilide 'F, = 114 ° C. «= 116 ° C
P. β 129 CP. β 129 C
P. = 93°0P. = 93 ° 0
P. a 122°0P. a 122 ° 0
P. = 104 - 106°CP. = 104-106 ° C
P. «= 127 - 128°CP. «= 127 - 128 ° C
P· ■β 88 - 89 CP · ■ β 88-89 C
P. β· 115 -P. β 115 -
P. » 940OP. »94 0 O
3-0ximino-2-methylbutan-0-carbonsäure-3'-(N-ß-chloräthyl-carbamoyloxy)-anilid p. B 126 - 1290C3-0ximino-2-methylbutane-0-carboxylic acid 3 '- (N-ß-chloroethyl-carbamoyloxy) -anilide p. B 126 - 129 0 C
= 1,5190 *= 1,5215 = 1,5332 "= 1.5190 * = 1.5215 = 1.5332 "
2-Oximinopropan-0-carbonsäure-3f-(pivalyloxy)-anilid 2-Oximinopropane-0-carboxylic acid-3 f - (pivalyloxy) -anilide
3-Oximinopentan-0-carbonsäure-3l- 203-oximinopentane-0-carboxylic acid-3 l - 20
(pivalyloxy)-anilid nD(pivalyloxy) anilide n D
3-Oximinopentan-0-carbonsäure-3I- 20 (äthoxycarbonyloxy)-anilid D3-Oximinopentane-0-carboxylic acid-3 I - 20 (ethoxycarbonyloxy) anilide D
009838/2282 - 17 - 009838/2282 - 17 -
P. 1126.00/Dr.Iiie/RiP. 1126.00 / Dr.Iiie / Ri
Verbin- Name der Verbindung PhysikalischeConnection- Name of the connection physical
dung ' Konstantedung 'constant
• 90 3-0ximino-2-methylbutan~0-carbonsäure-3'-(N-methylcarbamoyloxy)-anilid P. = 155 - 1580C• 90 3-0ximino-2-methylbutane ~ 0-carboxylic acid 3 '- (N-methylcarbamoyloxy) -anilide P. = 155-158 0 C.
Sl 3-Qximino~2-methylbutan-0-carbon-Sl 3-Qximino ~ 2-methylbutane-0-carbon-
säure-(N*-a-naphthylcarbamoyloxy)-acid- (N * -a-naphthylcarbamoyloxy) -
anilid - P. = 136 - 1380Canilide - P. = 136 to 138 0 C
92 3-0ximno-2~methylbutan-0-carbon- ,92 3-0ximno-2 ~ methylbutane-0-carbon-,
säure-3l-(N-(3",4"-dimethylphenyloxy)-acid-3 l - (N- (3 ", 4" -dimethylphenyloxy) -
anilid P. = 176 - 177 Canilide P. = 176 - 177 C
93 3-0ximino-2-methylbutan-0-carbon-93 3-0ximino-2-methylbutane-0-carbon-
säure-3·-(N-(2 «,3"-dimethylphenylίο arbamoyl oxy)-anilid P· = 158 - 1600C acid 3 · - (N- (2 ", 3" -dimethylphenylίο arbamoyl oxy) -anilide · P = 158-160 0 C.
94 3-0ximino-2-methylbutan-0-carbon-94 3-0ximino-2-methylbutane-0-carbon-
säure-3t-(N-(2"-methyl-4"-chlorphenyl)-carbamoyloxy;-anilid acid-3 t - (N- (2 "-methyl-4" -chlorophenyl) -carbamoyloxy; -anilide
95 2-0ximinopen1;an-0-carbonsäure-3l-95 2-0ximinopen1; an-0-carboxylic acid-3 l -
(N-äthylcarbamoyloxy)-anilid(N-ethylcarbamoyloxy) anilide
96 2-0ximinopentan-0-carbonsäure-3f-96 2-0ximinopentane-0-carboxylic acid-3 f -
(N-n-propylcarbamoyloxy)-anilid(N-n-propylcarbamoyloxy) anilide
97 2-0ximinopentan-0-carbonsäure-3'-97 2-0ximinopentane-0-carboxylic acid-3'-
(N^isopropylcarbamoyloxyJ-anilid Harz(N ^ isopropylcarbamoyloxyJ-anilide resin
98 2-0ximinopentan-0-carbonsäure-3t-98 2-0ximinopentane-0-carboxylic acid-3 t -
(N'-n-butylcarbamoyloxy)-anilid P. = 91 - 94 0(N'-n-butylcarbamoyloxy) anilide P. = 91-94 0
99 3-0ximino-2-methylbutan-0-carbon-99 3-0ximino-2-methylbutane-0-carbon-
säure-3'-(N'-n-hexylcarbamoyloxy)-anilid Harzacid 3 '- (N'-n-hexylcarbamoyloxy) anilide resin
100 3-0ximino-2-methylbutan-0-carbon-100 3-0ximino-2-methylbutane-0-carbon-
säure-3'-(N'-furfurylcarbamoyloxy)-■ anilid Harzacid-3 '- (N'-furfurylcarbamoyloxy) - ■ anilide resin
101 3-0ximino-2-methylbutan-0-carbon-101 3-0ximino-2-methylbutane-0-carbon-
s äure-3-(N'-n-o etylcarbamoyloxy)-acid-3- (N'-n-o etylcarbamoyloxy) -
anilid P. = 78 - 81°Canilide P. = 78 - 81 ° C
102 3-0ximino-2-methylbutan-0-carbon-102 3-0ximino-2-methylbutane-0-carbon-
säure-3'-(N-isobutylcarbamoyloxy)-acid-3 '- (N-isobutylcarbamoyloxy) -
anilid P. = 77 - 79 Canilide P. = 77-79 C.
103 3-0ximino-2-methylbutan-0-carbon-103 3-0ximino-2-methylbutane-0-carbon-
säure-3'-(N-n-butylcarbamoyloxy)-acid-3 '- (N-n-butylcarbamoyloxy) -
anilid P. = 80 - 82°Canilide P. = 80 - 82 ° C
009833/2282009833/2282
- 18 -- 18 -
P. 1126.0Q/Dr.Lie/RlP. 1126.0Q / Dr.Lie / Rl
Verbin- Name der Verbindung PhysikalischeConnection- Name of the connection physical
dung · Konstante Nr.dung constant no.
2-0ximinopentan-0-carbonsäure-3'-2-0ximinopentane-0-carboxylic acid-3'-
(N-phenylcarbamoyloxy)-anilid Ρ· = 133 - 136 C(N-phenylcarbamoyloxy) -anilide Ρ = 133 - 136 C
2-0ximinopentan-0-carbonsäure-3f-(N-cyclohexylcarbamoyloxy)-anilid P. = 104 - 1OS0O2-0ximinopentane-0-carboxylic acid-3 f - (N-cyclohexylcarbamoyloxy) -anilide P. = 104-1OS 0 O
2-0ximinopentan-0-carbonsäure-3'-2-0ximinopentane-0-carboxylic acid-3'-
(N-(2"-methylphenyl)-carbamoyloxy)-(N- (2 "-methylphenyl) -carbamoyloxy) -
anilid P. = 113 - 116°0anilide P. = 113 - 116 ° 0
2-0ximinopentan-0-carbonsäure-3l-2-0ximinopentane-0-carboxylic acid-3 l -
(N-(4"-methylphenyl-carbamoyloxy)-(N- (4 "-methylphenyl-carbamoyloxy) -
anilid F. = 159 -. 161,5anilide F. = 159 -. 161.5
2-0ximinopentan-0-carbonsäure-3f-2-0ximinopentane-0-carboxylic acid-3 f -
(N-(3"-methylphenyl-carbamoyloxy)-(N- (3 "-methylphenyl-carbamoyloxy) -
anilid ■ P. = I31 - 134anilide ■ P. = I31-134
2-0ximinopentan-0-carbonsäure-3t-2-0ximinopentane-0-carboxylic acid-3 t -
(N-n-hexylcarbamoyloxy)-anilid P. = 99 - 102 3-0ximino-2-methylbutan-0-carbon- «n(N-n-hexylcarbamoyloxy) -anilide P. = 99-102 3-0ximino-2-methylbutane-0-carbon- «n
säure-3t-(N,N-dimethylcarbamoyl- n-rj « 1,5561 oxy)-anilid 3-0ximino-2-methylbutan-0-carbon-acid-3 t - (N, N-dimethylcarbamoyl- n-rj «1,5561 oxy) -anilide 3-0ximino-2-methylbutane-0-carbon-
säure-3*-(N,N-diäthylcarbamoyloxy)-9n acid-3 * - (N, N-diethylcarbamoyloxy) - 9n
anilid n^u = 1,5200anilide n ^ u = 1.5200
3-0ximino-2-methylbutan-0-carbon-3-0ximino-2-methylbutane-0-carbon-
säure-3'-(N-methyl-N-phenylcarbamo-o n acid-3 '- (N-methyl-N-phenylcarbamo-o n
yloxy)-anilid · n^ = 1,5690 2-0ximinopentan-0-carbonsäure-3'-yloxy) anilide * n ^ = 1.5690 2-0ximinopentane-0-carboxylic acid-3'-
(N-tert.-butylcarbamoyloxy)-aniaid P, = 125 -128 C 2-0ximinopentan-0-carbonsäure-3!-(N-tert-butylcarbamoyloxy) -aniaid P, = 125 -128 C 2-oximinopentane-0-carboxylic acid-3 ! -
(N-(2",4"-dimethylphenyl)-carbamoyl-(N- (2 ", 4" -dimethylphenyl) -carbamoyl-
oxy)-anilid P. = 140 - 1420Coxy) -anilide P. = 140-142 0 C
2-0ximinopentan-0-carbonsäure-3I- '2-0ximinopentane-0-carboxylic acid-3 I - '
(N-(3"-methoxyphenyl)-carbamoyloxy)-(N- (3 "-methoxyphenyl) -carbamoyloxy) -
anilid P. =139 - 141,5anilide P. = 139-141.5
2-0ximinopentan-0-carbonsäure-3l-2-0ximinopentane-0-carboxylic acid-3 l -
(N- ( 3 "-chlorphenyl) -carbamoyloxy )-(N- (3 "-chlorphenyl) -carbamoyloxy) -
anilid Pe = 146 - 1490Canilide P e = 146-149 0 C.
009838/2282 "009838/2282 "
" 1S " P. I126.00/Dr.Lie/Ri " 1S " P. I126.00 / Dr.Lie / Ri
Verbin- Käme der Verbindung PhysikalischeConnection would be the connection physical
dung Konstantedung constant
- 117 3-Oximino-2-methylbutan-0-carbon- 9n - 117 3-oximino-2-methylbutane-0-carbon- 9n
eä\ire-3I-(N-2l^äthylhexylcarba- n£ = 1,5188eä \ ire-3 I - (N-2 l ^ äthylhexylcarba- n £ = 1.5188
moyloxy)-anilidmoyloxy) anilide
3-Qxin»ino-2-methylbutan-0-earbon-3-Qxin »ino-2-methylbutane-0-earbon-
eäure^'-CN-te" ,4H-dimethylphenyl)-acid ^ '- CN-te ", 4 H -dimethylphenyl) -
carbamoyloxy)-anilid Ρ· « 156 - 158 Ccarbamoyloxy) anilide Ρ · «156 - 158 C
3-0ximino-2-methylbutan-Q-carbon-3-0ximino-2-methylbutane-Q-carbon-
ßäure-3'-(N-(3"-methoxyphenyl)-acid-3 '- (N- (3 "-methoxyphenyl) -
carbamoyloxy)-anilid P. « 134 - 135 0carbamoyloxy) anilide P. «134-135 0
3-0ximino-2-methylbutan-0-carbon-3-0ximino-2-methylbutane-0-carbon-
säure-3l-(N-(4l1-äthylphenyl)-acid-3 l - (N- (4 l1 -ethylphenyl) -
carbamoyloxyj-anilid F. « 164 - 165 0carbamoyloxyj-anilid F. «164 - 165 0
2-0ximinobutan-0-carbonsäure-3l-2-0ximinobutane-0-carboxylic acid-3 l -
(N-methylcarbamoyloxy)-anilid P. = I31 - I33 C 2-0ximinobutan-0-carbon8äure-3l-(N-methylcarbamoyloxy) -anilide P. = I31 - I33 C 2-0ximinobutane-0-carbon8 acid-3 l -
(N-äthylcarbamoyloxy)-anilid P. a 143 - 145 C 2-Oximinobutan-0-carbonsäure-3l-(N-ethylcarbamoyloxy) -anilide P. a 143 - 145 C 2-oximinobutane-0-carboxylic acid-3 l -
(N-n-propylcarbamoyloxy)-anilid P. = 131- 132 C 2-0ximinobutan-0-carbonsäure-3l-(Nn-propylcarbamoyloxy) -anilide P. = 131-132 C 2-0ximinobutane-0-carboxylic acid-3 l -
(N-isopropylcarbamoyloxy)-anilid P. = 134 - 135 C 2-Oximinobutan-0-carbonsäure-3I-(N-isopropylcarbamoyloxy) -anilide P. = 134 - 135 C 2-oximinobutane-0-carboxylic acid-3 I -
(H-phenylcarbamoyloxy)-anilid P# « 146 - 148 C 2-0ximinobutan-0-carbonsäure-31-(H-phenylcarbamoyloxy) -anilide P # «146 - 148 C 2-oximinobutane-0-carboxylic acid-3 1 -
(N-n-butylcarbamoyloxy)-anilid P, « 107 - 1090O 2-0ximinobutan-0-carbonsäure-3'-(Nn-butylcarbamoyloxy) -anilide P, « 107-109 0 O 2-oximinobutane-0-carboxylic acid-3'-
(NrS ek·-butylc arbamoyloxy)-(NrS ek -butylc arbamoyloxy) -
anilid P. * II9 - 1220Canilide P. * II9 - 122 0 C
2-0ximinobutan-0-carbonsäure-3f-2-0ximinobutane-0-carboxylic acid-3 f -
(N-t ert·-butylcarbamoyloxy)-(N-t ert -butylcarbamoyloxy) -
anilid P. * 98 - 1010Canilide P. * 98-101 0 C.
2-0ximinobutan-Ö-carbonsäure-3f-2-0ximinobutane-Ö-carboxylic acid-3 f -
(N-n-hexylcarbamoyloxy)-anilid P, « 100 - 1010C(Nn-hexylcarbamoyloxy) anilide P, "100 to 101 0 C
' 130 2-Oximinobutan-0-carbonBäure-3l-'130 2-Oximinobutane-0-carbonic acid-3 l -
(N-allylcarbamoyloxy)-anilid P. « 127- 1290C 2-Oximinobutan-0-carbonsäure-3l-(N-allylcarbamoyloxy) -anilide P. «127-129 0 C 2-oximinobutane-0-carboxylic acid-3 l -
(K-cyclohexylcarbamoyloxy)-anilid P, = 128 - 1310C(K-cyclohexylcarbamoyloxy) -anilide P = 128-131 0 C.
009838/2282009838/2282
- 20 -- 20 -
P. 1126.00/Dr.Ide/RiP. 1126.00 / Dr Ide / Ri
Verbin- Name der Verbindung PhysikalischeConnection- Name of the connection physical
dung Konstantedung constant
2-0ximinobutan-0-carbonsäure-3l-2-0ximinobutane-0-carboxylic acid-3 l -
(N-(2"-methylphenyl)-carbamoyloxy)-(N- (2 "-methylphenyl) -carbamoyloxy) -
anilid P. = 135 - 138°Canilide P. = 135 - 138 ° C
2-Oximinobutan-0-carbonsäure~3'-2-oximinobutane-0-carboxylic acid ~ 3'-
(N-(3"-methylphenyl)-carbamoyloxy)-(N- (3 "-methylphenyl) -carbamoyloxy) -
anilid P. = I40 - 141 0anilide P. = I40 - 141 0
2-Oximinobutan-0-carbonsäure-3'-·2-Oximinobutane-0-carboxylic acid-3'- ·
(N-(4"-methylphenyl)-carbamoyloxy)-(N- (4 "-methylphenyl) -carbamoyloxy) -
anilid · " P. = 144 - 1460Canilide · "P. = 144 to 146 0 C
3-0ximino-2-methylbutan-0-carbonsäure-3-0ximino-2-methylbutane-0-carboxylic acid
3'-(N-isopropylcarbamoyloxy)-anilid P. = 110 - 112 C 3-0ximino-2-methylbutan-0-carbonsäure-3 '- (N-isopropylcarbamoyloxy) anilide P. = 110-112 C 3-0ximino-2-methylbutane-0-carboxylic acid
3·-(N-2",2"-dimethylpropylcarbamoyloxy)-3 · - (N-2 ", 2" -dimethylpropylcarbamoyloxy) -
anilid P# = 123 - 124 Canilide P # = 123-124 C
3-0ximino-2-methylbutan-0-carbonsäure-3-0ximino-2-methylbutane-0-carboxylic acid
3'-(N-sek.-butylcarbamoyloxy)-3 '- (N-sec-butylcarbamoyloxy) -
anilid P. = 124 - 125 0anilide P. = 124 - 125 0
3-0ximino-2-methylbutan-0-carbon-3-0ximino-2-methylbutane-0-carbon-
säure-3'-(N-tert·-butylcarbamoyloxy)-acid-3 '- (N-tert -butylcarbamoyloxy) -
anilid P. = 97 - 980Canilide P. = 97-98 0 C
2-0ximinobutan-0-carbonsäure-3'-2-0ximinobutane-0-carboxylic acid-3'-
(N-is0butylcarbamoyloxy)-anilid P. = 92 - 93 0 2-0ximinobutan-0-carbonsäure-3l-(N-is0butylcarbamoyloxy) -anilide P. = 92 - 93 0 2-0ximinobutane-0-carboxylic acid-3 l -
(N-(2-äthylhexyl)-carbamoyloxy)- v (N- (2-ethylhexyl) carbamoyloxy) - v
anilid P. = 52 - 57 Canilide P. = 52 - 57 C
l-Oximino-l-phenyläthan-O-carbonsäure-l-oximino-l-phenylethane-O-carboxylic acid
3'-(N-methylcarbamoyloxy)-anilid P. ='ll8 - 122 C3 '- (N-methylcarbamoyloxy) anilide P. =' 118-122 C
Die neuen Phenylcarbamate sind löslich in organischen Lösungsmitteln, wie z.B. Aceton, Isophoron, Chloroform, Dimethylformamid, Dirnethylsulfoxid, Tetrahydrofuran, Dioxan, Essigsäur eäthylest er, Cyclohexanon u.a.The new phenyl carbamates are soluble in organic solvents, such as acetone, isophorone, chloroform, dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, dioxane, acetic acid ethyl ester, cyclohexanone etc.
Die für die Herstellung als Ausgangsprodukte benötigten . .The raw materials required for production. .
- 21 -- 21 -
009838/2282009838/2282
13130431313043
Oxim-O-CthioJ-carbonsäurehydroxyanilide lassen sich, aus den Chlorameisensäureestern von Oximen und Aminophenolen sowohl in Wasser als auch in einem organischen Lösungsmittel, z.B· Acetonitril, Tetrahydrofugan, Dioxan oder Essigester herstellen, wobei zweckmäßigerweise ein säurebindendes Mittel wie Na2CO3, KgCO,, NaOH, KOH, MgO oder Triethylamin zugesetzt werden kann·Oxime-O-CthioJ-carboxylic acid hydroxyanilides can be prepared from the chloroformic acid esters of oximes and aminophenols both in water and in an organic solvent, e.g. acetonitrile, tetrahydrofugan, dioxane or ethyl acetate, an acid-binding agent such as Na 2 CO 3 , KgCO ,, NaOH, KOH, MgO or triethylamine can be added ·
Im folgenden wird die Herstellung eines der Ausgangsprodukte beschrieben:The production of one of the starting products is described below:
2-Oximinopro-pan-0-carbonsäure-3t -hydroxy anilid 206 g (1,88 Mol) m-Aminophenol und 38 g MgO werden in 11 Essigester und 600 ml Wasser aufgenommen. Unter Rühren werden 255 g Chlorformylacetonoxim eingetropft, wobei die Reaktionstemperatur durch Kühlung bei ca, 150C gehalten wird. 20 Minuten wird bei dieser Temperatur nachgerührt, dann mit lO^iger Salzsäure angesäuert und anschließend das auskristallisierte Reaktionsprodukt abgesaugt und an der Luft getrocknet. Ausbeute: 323 g = 83$ der Iheorie F. 153-1540C 2-Oximinopro-pan-0-carboxylic acid 3-hydroxy anilide t 206 g (1.88 mol) of m-aminophenol and 38 g of MgO are added in Essigester 11 and 600 ml water. With stirring, 255 g Chlorformylacetonoxim wherein the reaction temperature by cooling at about 15 0 C is maintained are dropped. The mixture is stirred at this temperature for 20 minutes, then acidified with 10 ^ hydrochloric acid and then the reaction product which has crystallized out is filtered off with suction and dried in the air. Yield: 323 g = 83 $ of Iheorie F. 153-154 0 C.
Analog werden folgende Ausgangsprodukte erhalten: 2-Oximinobutan-0-carbonsäure-3'--hydroxyanilid P. 136-1370C 2-0ximinopentan-0-carbonsäure-3'-hydroxyanilid i1. 138-1390C 2-0ximino-3-methylbutan-0-carbonsäure-3 * -The following starting materials are obtained analogously: 2-oximinobutane-0-carboxylic acid 3'-hydroxyanilide P. 136-137 0 C 2-oximinopentane-0-carboxylic acid 3'-hydroxyanilide i 1 . 138-139 0 C 2-0ximino-3-methylbutane-0-carboxylic acid-3 * -
hydrox„. 'inüLd P. 85- 87 0hydrox ". 'inüLd P. 85-87 0
3-Oxiininopentan-0-carbonsäure-3l -3-oxininopentane-0-carboxylic acid-3 l -
hydroxyanilid S1. 119-12O0Chydroxyanilide S 1 . 119-12O 0 C
l-Oximino-l-phenyläthan-O-carbonsäure-S'-l-oximino-l-phenylethane-O-carboxylic acid-S'-
hydroxyanilid p# 134-136,50Chydroxyanilide p # 0 134 to 136.5 C
009838/2282009838/2282
- 22 -- 22 -
2-Oximino-4-methylpentan-0-carbonsäure-3 %- 2-oximino-4-methylpentane-0-carboxylic acid 3 % -
hydroxyanilid P. 121-123 Chydroxyanilide P. 121-123 C
2-Oximino-n-undecan-O—carbonsäure-3f- „ .2-Oximino-n-undecane-O-carboxylic acid-3 f - ".
hydroxyanilid P. 75- 760Chydroxyanilide P. 75- 76 0 C
l-Oximino-3· 3· 5-trimethylcyclohexan-(5 )-O-l-oximino-3 3 5-trimethylcyclohexane (5) -O-
carbonsäure-31-hydroxyanilid P· 166-168 Gcarboxylic acid 3 1 -hydroxyanilide P · 166-168 G
(Zersetzung)(Decomposition)
2-Oximinopropan-0-carbonsäure-4-f-hydroxyanilid P. 177-1780C2-Oximinopropane-0-carboxylic acid-4- f -hydroxyanilide P. 177-178 0 C
Die neuen Phenyl carbamate können allein oder als Mischungen untereinander und/oder mit anderen Herbiziden und/oder sonstigen Stoffen,z.B. Düngemitteln, zur Unkrautbekämpfung " angewandt werden·The new phenyl carbamates can be used alone or as mixtures with one another and / or with other herbicides and / or other substances, e.g. Fertilizers, for weed control "to be applied ·
Die Anwendung erfolgt zweckmäßig in einer für eine Unkrautbekämpfung üblichen Weise in Porm von Zubereitungen, wie z.B. Pulvern, Streumitteln, Granulaten, Lösungen, Emulsionen oder Suspensionen, unter Zusatz von flüssigen und/oder festen Trägerstoffen bzw. Verdünnungsmitteln und gegebenenfalls Netz-, Haft-, Emulgier- und/oder Dispergierhilfsmitteln.It is expediently used in a weed control Usually in the form of preparations such as powders, scattering agents, granules, solutions, emulsions or suspensions, with the addition of liquid and / or solid Carriers or diluents and optionally wetting agents, adhesives, emulsifying agents and / or dispersing agents.
Die Herstellung der verschiedenen Zubereitungsformen erfolgt in einer der für Pflanzenschutzmittel üblichen Pormen unter Verwendung flüssiger oder fester inerter Trägerstoffe bzw. Verdünnungsmittel und gegebenenfalls Zusatz von oberflächenaktiven Stoffen.The various preparation forms are produced in one of the porms customary for plant protection products Use of liquid or solid inert carriers or Diluent and, if necessary, addition of surface-active substances.
Geeignete flüssige Trägerstoffe sind z.B. organische Lösungsmittel wie Isophoron, Dimethylformamid, Dirnethylsulfoxyd, Tetrahydrofugan, Cyclohexanon u.a.Suitable liquid carriers are, for example, organic solvents such as isophorone, dimethylformamide, dimethyl sulfoxide, Tetrahydrofugan, cyclohexanone and others
009838/2282009838/2282
- 23 -- 23 -
Als feste Trägerstoffe kommen in Betracht z.B. Kalk, Kaolin, Talkum, natürliche oder synthetische Kieselsäure, Attaclay und andere Tone·Suitable solid carriers are e.g. lime, kaolin, Talc, natural or synthetic silica, attaclay and other clays
Als oberflächenaktive Stoffe eignen sich z.B. Salze der Ligninsulfosäure, Salze von alkylierten Benzolsulfonsäuren, sulfonierte Säureamide und deren Salze, PoIyglykole, Polyäthoxylierte Amine, Alkohole und Phenole.Suitable surface-active substances are e.g. salts of lignin sulfonic acid, salts of alkylated benzenesulfonic acids, sulfonated acid amides and their salts, polyglycols, Polyethoxylated amines, alcohols and phenols.
Die Zusammensetzung einer derartigen Zubereitung ist z.B.The composition of such a preparation is e.g.
wie folgt: . -as follows: . -
etwa θ Gewichtsprozent Wirkstoffabout θ percent by weight active ingredient
etwa 23 Gewichtsprozent oberflächenaktiver Stoffe etwa 69 Gewichtsprozent Lösungsmittelabout 23 weight percent surfactants about 69 weight percent solvent
Die herbizide Wirkung der erfindungsgemäßen Verbindung und ihre Verwendung als selektive herbizide Mittel geht aus den folgenden Versuchsbeispielen hervor:The herbicidal activity of the compound according to the invention and its use as selective herbicidal agents are based on the the following test examples:
Die in der Tabelle aufgeführten Verbindungen wurden in einer Aufwandmenge von 5 kg/ha Wirksubstanz, suspendiert in 600 l/ha, auf Senf und Tomaten als Testpflanzen gespritzt.The compounds listed in the table were suspended at an application rate of 5 kg / ha of active substance in 600 l / ha, sprayed on mustard and tomatoes as test plants.
Im Gegensatz zum Vergleichsmittel Isopropyl-N-(3-chlorphenyl)-carbamat, das emulgiert in 600 1 Wasser/ha gespritzt wurde, erreichte man eine Vernichtung der Testpflanzen·In contrast to the comparison agent isopropyl-N- (3-chlorophenyl) -carbamate, which was sprayed emulsified in 600 l of water / ha, the test plants were destroyed
009838/2282009838/2282
191 3 OA 3191 3 OA 3
1 2 3 4 5 61 2 3 4 5 6
7 8 7 8
9 109 10
11 1211 12
13 14 15 1613 14 15 16
, 17, 17th
1818th
.19'.19 '
20 21 2220 21 22
2323
24 2524 25
009838/2282009838/2282
191306191306
Verbindung link ΉνΉν . Senf Tomaten. Mustard tomatoes
O 0 2 0O 0 2 0
5 O 5 O
5 65 6
- 26 -- 26 -
009838/2282009838/2282
P. 1126,00/Dr.Lie/HiP. 1126.00 / Dr Lie / Hi
009838/2282009838/2282
?. 1126.00/Dr.Ide/Ri?. 1126.00 / Dr Ide / Ri
009838/2282009838/2282
Senfmustard
Tomatentomatoes
phenyl)-carbamatIsopropyl-IT- (3-chloro-
phenyl) carbamate
10 β nicht geschädigt;10 β not damaged;
0 a total vernichtet0 a totally destroyed
Bei Behandlung auf unbewachsenen Sandboden wurden vor dem Auflaufen der -Unkräuter die aufgeführten Wirkstoffe in einer Aufwandmenge von 0,3 kg/ha gespritzt. Die erfindungsgemäßen Wirkstoffe wurden suspendiert ausgebracht, während das Vergleichsmittel, Isopropyl-N-(3~chlorphenyl)-carbamat, emulgiert gespritzt wurde. Alle Präparate wurden in einer Wasseraufwandmenge von 600 l/ha ausgebracht. Wie aus der Tabelle ersichtlich wird, erzielten die erfindungsgemäßen Mittel gegen hartnäckige Unkrautarten wie Franzosenkraut, Kreuzkraut, Kamille und Taubnessel eine gute Wirkung, während das Vergleichsmittel Isopropyl-H-(3-chlorphenyl)-carbamat gegen diese Unkräuter* überwiegend ohne Wirkung war.When treated on bare sandy soil were before emergence der -weeds sprayed the listed active ingredients at an application rate of 0.3 kg / ha. The invention Active ingredients were applied in suspension, while the comparison agent, isopropyl-N- (3-chlorophenyl) -carbamate, emulsified was injected. All preparations were applied with a water application rate of 600 l / ha. As can be seen from the table is achieved, the agents according to the invention against stubborn Weed species such as French cabbage, ragwort, chamomile and dead nettle have a good effect, while the comparison agent Isopropyl-H- (3-chlorophenyl) -carbamate against these weeds * was mostly ineffective.
009838/2282009838/2282
0? a b e 1 1 e0? a b e 1 1 e
Verbin- Erbsen Mohren Baum- Senf Vogel- Pran- Kreuz- Kamille dung ' wolle miere zosen- kraut ness@l Hr. kraut , .Verbin- peas carrots tree mustard bird pran cross chamomile dung 'wool miere zosenkraut ness @ l Hr. herb,.
0I.
0
N-(3-chlor-
phenyl)-
carbamatIsopropyl 10
N- (3-chloro-
phenyl) -
carbamate
10 = nicht geschädigt; 0 = total vernichtet10 = not damaged; 0 = totally destroyed
Beispiel 3Example 3
Bei Anwendung im Nachauflauf wurden die in der Safeelle auf gefüllten Verbindungen in einer Aufwandmenge von 1 kg Wirkst off/ha auf Kulturpflanzen und in einer Aufwandmenge von 0?5 kg Wirkstoff/ha auf Unkräuter, emulgiert in 600 1 Wasser/ha, gespritzt. Die Ergebnies© zeigen deutlich die bessere Verträglichkeit der erfindungsgemäßen lütt el gegenüber den Kulturpflanzen Weizen, Mais und Erdnüsse s während das Vergleichsmittel diese stark schädigte· Darüber hinaus wurde mit den erfindungsg'emäßen Mitteln zum Seil eine bessere Unkrautwirkung erzielt·When used post-emergence, the compounds filled in the Safeelle were applied to crops at an application rate of 1 kg of active ingredient / ha and at an application rate of 0 ? 5 kg active ingredient / ha on weeds, emulsified in 600 l water / ha, sprayed. The Ergebnies © clearly show the better tolerability of the invention lütt el against the crops of wheat, corn and peanuts s while the comparison means these highly damaged · In addition, achieves better weed control with the erfindungsg'emäßen means for cable ·
Verbin- Weizen Mais Erd- Senf Vogel- Kreuz- Kamille Saubdungnüsse miere kraut nesselCombined wheat corn peanut mustard bird cross chamomile saubnuts miere herb nettle
Hr.Mr. ||
Verbin- Weizen. Mais Erd- Senf Vogel- Kreuz- Kamille Taubdung nüsse miere kraut nessel Hr.Conn- wheat. Corn earth mustard bird cross chamomile deaf dung nuts miere kraut nettle Mr.
l'Iethyl-li-( 3-(H «-21,2t-l'ethyl-li- (3- (H «-2 1 , 2t-
dime thylpropylcarbamoyloxy) phenyl)carbamatdime thylpropylcarbamoyloxy) phenyl) carbamate
At hy 1-N- ( 3-K«- ( ?-chl orphenyl)earfoaooyloxy)phenyl carbamatAt hy 1-N- (3-K "- (? -Chlorophenyl) earfoaooyloxy) phenyl carbamate
7 97 9
2-Chlor-4-äthylamino-6-isopropylamino-1,3»5-triazin 2-chloro-4-ethylamino-6-isopropylamino-1,3 »5-triazine
1 10 11 10 1
10 = nicht geschädigt;009838/228210 = not damaged; 009838/2282
total vernichtettotally destroyed
Bei Anwendung im Nachauflauf auf Reis und Hirse wurden die in der Tabelle aufgeführten Verbindungen in einer Aufwandmenge von 1 kg Wirkst off/ha auf die Kulturpflanzen und in einer Aufwandmenge von 0,5 kg/ha auf die Hirse gespritzt. Aus den Ergebnissen geht die bessere Verträglichkeit bzw. die größere Wirkung der erfindungBgemäßen Verbindungen im Vergleich zu den bekannten Herbiziden hervor.When used post-emergence on rice and millet, the compounds listed in the table were applied in one amount of 1 kg of active ingredient / ha on the crop plants and in one application rate of 0.5 kg / ha sprayed onto the millet. The results show the better tolerance or the greater one Effect of the compounds according to the invention in comparison to the known herbicides.
1ν
1
dimethylpropyl-
carbamoyloxy)phenyl)
carbamatI-ethyl-Ii- (3- (1I 1 -2 1 , 2 ^
dimethylpropyl
carbamoyloxy ) phenyl)
carbamate
Propionsäure-(3,4-dichloranilid) 10 4Propionic acid (3,4-dichloroanilide) 10 4
0 0 90 0 9
10 = nicht geschädigt; 0 = total vernichtet10 = not damaged; 0 = totally destroyed
Claims (1)
N-CX- 0| 5
N-CX- 0
^R 'St.
^ R '
oder einem Oxim der allgmeinen IOrmelHO - R 5
or an oxime of the common IOrmel
einer tertiären organischen Base zur Umsetzung bringt, wobei in den allgemeinen Formeln R-, ', R-j% Ro8 und Rp" obenbezeichnete Bedeutung von S1 und/oder E9 besitzen,optionally with the addition of an inorganic or
brings a tertiary organic base to the reaction, where in the general formulas R-, ', Rj% Ro 8 and Rp "have the abovementioned meaning of S 1 and / or E 9 ,
Priority Applications (22)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691913043 DE1913043C3 (en) | 1969-03-11 | Substituted phenyl carbamates | |
| LU60296D LU60296A1 (en) | 1969-03-11 | 1970-02-03 | |
| RO62450A RO56476A (en) | 1969-03-11 | 1970-02-12 | |
| CH210370A CH563712A5 (en) | 1969-03-11 | 1970-02-13 | |
| YU00379/70A YU36371B (en) | 1969-03-11 | 1970-02-17 | Process for obtaining substituted phenyl-carbamates |
| ES376874A ES376874A1 (en) | 1969-03-11 | 1970-02-24 | Substituted phenylcarbamates |
| BG014082A BG17274A3 (en) | 1969-03-11 | 1970-02-28 | HERBICIDE |
| DK109470AA DK126321B (en) | 1969-03-11 | 1970-03-05 | Substituted phenyl carbamates for use in herbicides. |
| FI700599A FI51097C (en) | 1969-03-11 | 1970-03-05 | Use of substituted phenyl carbamates for weed control. |
| PL1970139209A PL80472B1 (en) | 1969-03-11 | 1970-03-06 | |
| AT214170A AT301251B (en) | 1969-03-11 | 1970-03-06 | Herbicides |
| CS1555A CS165339B2 (en) | 1969-03-11 | 1970-03-09 | |
| NO830/70A NO131171C (en) | 1969-03-11 | 1970-03-10 | |
| JP2041670A JPS5343570B1 (en) | 1969-03-11 | 1970-03-10 | |
| SE03157/70A SE350033B (en) | 1969-03-11 | 1970-03-10 | |
| IE315/70A IE34053B1 (en) | 1969-03-11 | 1970-03-10 | Substituted phenylcarbamates |
| IL34054A IL34054A (en) | 1969-03-11 | 1970-03-10 | Substituted phenylcarbamates |
| GB1167270A GB1308183A (en) | 1969-03-11 | 1970-03-11 | Substituted phenylcarbamates |
| FR7008701A FR2037943A5 (en) | 1969-03-11 | 1970-03-11 | |
| NLAANVRAGE7003504,A NL173636C (en) | 1969-03-11 | 1970-03-11 | METHOD FOR PREPARING A HERBICIDE PREPARATION; PROCESS FOR PREPARING AN OXIMINOALKANE-O-CARBANILIDE. |
| BE747208D BE747208A (en) | 1969-03-11 | 1970-03-11 | SUBSTITUTE PHENYL CARBAMATES, THEIR PREPARATION AND USE |
| YU2438/75A YU36697B (en) | 1969-03-11 | 1975-09-29 | Process for obtaining new substituted phenylcarbamates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691913043 DE1913043C3 (en) | 1969-03-11 | Substituted phenyl carbamates |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1913043A1 true DE1913043A1 (en) | 1970-09-17 |
| DE1913043B2 DE1913043B2 (en) | 1977-05-12 |
| DE1913043C3 DE1913043C3 (en) | 1978-01-05 |
Family
ID=
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5343570B1 (en) | 1978-11-21 |
| AT301251B (en) | 1972-08-25 |
| YU36697B (en) | 1984-08-31 |
| NO131171C (en) | 1975-04-16 |
| GB1308183A (en) | 1973-02-21 |
| YU37970A (en) | 1981-11-13 |
| IE34053B1 (en) | 1975-01-22 |
| NO131171B (en) | 1975-01-06 |
| NL7003504A (en) | 1970-09-15 |
| DE1913043B2 (en) | 1977-05-12 |
| LU60296A1 (en) | 1970-04-06 |
| FR2037943A5 (en) | 1970-12-31 |
| RO56476A (en) | 1975-01-15 |
| YU243875A (en) | 1981-11-13 |
| PL80472B1 (en) | 1975-08-30 |
| IL34054A (en) | 1972-12-29 |
| FI51097C (en) | 1976-10-11 |
| CS165339B2 (en) | 1975-12-22 |
| BG17274A3 (en) | 1973-07-25 |
| CH563712A5 (en) | 1975-07-15 |
| ES376874A1 (en) | 1972-05-16 |
| NL173636B (en) | 1983-09-16 |
| YU36371B (en) | 1983-06-30 |
| NL173636C (en) | 1984-02-16 |
| BE747208A (en) | 1970-09-11 |
| DK126321B (en) | 1973-07-02 |
| IL34054A0 (en) | 1970-05-21 |
| IE34053L (en) | 1970-09-11 |
| SE350033B (en) | 1972-10-16 |
| FI51097B (en) | 1976-06-30 |
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| C3 | Grant after two publication steps (3rd publication) | ||
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