NL8000112A - DIURETHANES, METHOD FOR PREPARING THE SAME, AND HERBICIDES BASED ON THESE COMPOUNDS. - Google Patents
DIURETHANES, METHOD FOR PREPARING THE SAME, AND HERBICIDES BASED ON THESE COMPOUNDS. Download PDFInfo
- Publication number
- NL8000112A NL8000112A NL8000112A NL8000112A NL8000112A NL 8000112 A NL8000112 A NL 8000112A NL 8000112 A NL8000112 A NL 8000112A NL 8000112 A NL8000112 A NL 8000112A NL 8000112 A NL8000112 A NL 8000112A
- Authority
- NL
- Netherlands
- Prior art keywords
- ester
- acid
- phenyl
- fluoro
- ethyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 51
- 239000004009 herbicide Substances 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 10
- -1 hutyl Chemical group 0.000 claims description 159
- 239000002253 acid Substances 0.000 claims description 90
- 150000002148 esters Chemical class 0.000 claims description 86
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 230000002363 herbicidal effect Effects 0.000 claims description 8
- MGDDHBBPSNIXFW-UHFFFAOYSA-N (3-fluorophenyl)-methylcarbamic acid Chemical compound OC(=O)N(C)C1=CC=CC(F)=C1 MGDDHBBPSNIXFW-UHFFFAOYSA-N 0.000 claims description 7
- WZOMBBOIBCHWCP-UHFFFAOYSA-N (4-fluorophenyl)-methylcarbamic acid Chemical compound OC(=O)N(C)C1=CC=C(F)C=C1 WZOMBBOIBCHWCP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 229920000742 Cotton Polymers 0.000 claims description 4
- UAEPXXFSZDCODC-UHFFFAOYSA-N ethyl-(4-fluorophenyl)carbamic acid Chemical compound C(C)N(C(O)=O)C1=CC=C(C=C1)F UAEPXXFSZDCODC-UHFFFAOYSA-N 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 150000007530 organic bases Chemical group 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- HPJTZWQEMAHWEC-UHFFFAOYSA-N [3-(propanethioylamino)phenyl] N-ethyl-N-(2-fluorophenyl)carbamate Chemical compound C(C)C(=S)NC=1C=C(C=CC1)OC(N(C1=C(C=CC=C1)F)CC)=O HPJTZWQEMAHWEC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- OLTPKMBOLARPFC-UHFFFAOYSA-N phenyl(2-phenylethyl)carbamic acid Chemical compound C=1C=CC=CC=1N(C(=O)O)CCC1=CC=CC=C1 OLTPKMBOLARPFC-UHFFFAOYSA-N 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- KPRWEGORVIVZNZ-UHFFFAOYSA-N (4-fluorophenyl)-(2-phenylethyl)carbamic acid Chemical compound FC1=CC=C(N(C(O)=O)CCC2=CC=CC=C2)C=C1 KPRWEGORVIVZNZ-UHFFFAOYSA-N 0.000 claims 3
- BSAYWCZHCBTSCD-UHFFFAOYSA-N ethyl-(2-fluorophenyl)carbamic acid Chemical compound CCN(C(O)=O)C1=CC=CC=C1F BSAYWCZHCBTSCD-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- IDUFFHCIDXAHEZ-UHFFFAOYSA-N (4-fluorophenyl)-propylcarbamic acid Chemical compound FC1=CC=C(N(C(O)=O)CCC)C=C1 IDUFFHCIDXAHEZ-UHFFFAOYSA-N 0.000 claims 1
- DGBOBTHKVUXHGJ-UHFFFAOYSA-N [3-(ethanethioylamino)phenyl] N-ethyl-N-(2-fluorophenyl)carbamate Chemical compound CC(=S)NC=1C=C(C=CC1)OC(N(C1=C(C=CC=C1)F)CC)=O DGBOBTHKVUXHGJ-UHFFFAOYSA-N 0.000 claims 1
- YQAWQVGLWINZDT-UHFFFAOYSA-N [3-(ethoxycarbonylamino)phenyl] N-ethyl-N-(2-fluorophenyl)carbamate Chemical compound C(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=C(C=CC=C1)F)CC)=O YQAWQVGLWINZDT-UHFFFAOYSA-N 0.000 claims 1
- IPZQWWZBDMZXGK-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] N-(2-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound COC(=O)NC=1C=C(C=CC1)OC(N(C1=C(C=CC=C1)F)CCC1=CC=CC=C1)=O IPZQWWZBDMZXGK-UHFFFAOYSA-N 0.000 claims 1
- VCJUJZHGRYCPGJ-UHFFFAOYSA-N butyl-(4-fluorophenyl)carbamic acid Chemical compound CCCCN(C(O)=O)C1=CC=C(F)C=C1 VCJUJZHGRYCPGJ-UHFFFAOYSA-N 0.000 claims 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical group CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims 1
- 238000002844 melting Methods 0.000 description 64
- 230000008018 melting Effects 0.000 description 62
- 241000196324 Embryophyta Species 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 235000011331 Brassica Nutrition 0.000 description 8
- 241000219198 Brassica Species 0.000 description 8
- 235000002634 Solanum Nutrition 0.000 description 7
- 241000207763 Solanum Species 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- DJTODVVYZSSTCR-UHFFFAOYSA-N ethyl-(3-fluorophenyl)carbamic acid Chemical compound CCN(C(O)=O)C1=CC=CC(F)=C1 DJTODVVYZSSTCR-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- CNRYLCJODAIULK-UHFFFAOYSA-N (2-fluorophenyl)-(2-phenylethyl)carbamic acid Chemical compound FC1=C(N(C(O)=O)CCC2=CC=CC=C2)C=CC=C1 CNRYLCJODAIULK-UHFFFAOYSA-N 0.000 description 1
- PATNMSXWIVJSHC-UHFFFAOYSA-N (3-fluorophenyl)-propylcarbamic acid Chemical compound FC=1C=C(N(C(O)=O)CCC)C=CC1 PATNMSXWIVJSHC-UHFFFAOYSA-N 0.000 description 1
- GIRGFOHZHDGCJA-UHFFFAOYSA-N 2-[(2,3,6-trichlorophenyl)methoxy]propan-2-ol Chemical compound CC(C)(O)OCC1=C(Cl)C=CC(Cl)=C1Cl GIRGFOHZHDGCJA-UHFFFAOYSA-N 0.000 description 1
- JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical class NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 description 1
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000219318 Amaranthus Species 0.000 description 1
- 235000003276 Apios tuberosa Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000010744 Arachis villosulicarpa Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- KCVMWGGDYSDGJK-UHFFFAOYSA-N C(C)C1(C(C=C(NC(O)=O)C=C1)F)F Chemical compound C(C)C1(C(C=C(NC(O)=O)C=C1)F)F KCVMWGGDYSDGJK-UHFFFAOYSA-N 0.000 description 1
- 244000192528 Chrysanthemum parthenium Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241001071900 Scapanus orarius Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- OSNYWZDRPLKWTF-UHFFFAOYSA-N [3-(ethanethioylamino)phenyl] N-(3-fluorophenyl)-N-propylcarbamate Chemical compound CC(=S)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)CCC)=O OSNYWZDRPLKWTF-UHFFFAOYSA-N 0.000 description 1
- OXHJYBHEDUETFK-UHFFFAOYSA-N [3-(ethoxycarbonylamino)phenyl] N-(3-fluorophenyl)-N-methylcarbamate Chemical compound C(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)C)=O OXHJYBHEDUETFK-UHFFFAOYSA-N 0.000 description 1
- MHRVTXVWOWITHP-UHFFFAOYSA-N [3-(ethoxycarbonylamino)phenyl] N-ethyl-N-(4-fluorophenyl)carbamate Chemical compound C(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)F)CC)=O MHRVTXVWOWITHP-UHFFFAOYSA-N 0.000 description 1
- CUQAZLABXWMPDB-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] N-(3-fluorophenyl)-N-methylcarbamate Chemical compound COC(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)C)=O CUQAZLABXWMPDB-UHFFFAOYSA-N 0.000 description 1
- GUQLNCYGMDJFGO-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] N-(4-fluorophenyl)-N-methylcarbamate Chemical compound COC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)F)C)=O GUQLNCYGMDJFGO-UHFFFAOYSA-N 0.000 description 1
- ZOXXVYOXSGKIES-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] N-ethyl-N-(3-fluorophenyl)carbamate Chemical compound COC(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)CC)=O ZOXXVYOXSGKIES-UHFFFAOYSA-N 0.000 description 1
- BCVQHUYAKQYMDY-UHFFFAOYSA-N [3-(prop-2-ynoxycarbonylamino)phenyl] N-(4-fluorophenyl)-N-propylcarbamate Chemical compound C(C#C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)F)CCC)=O BCVQHUYAKQYMDY-UHFFFAOYSA-N 0.000 description 1
- VFTZASBGFWQIGJ-UHFFFAOYSA-N [3-(prop-2-ynoxycarbonylamino)phenyl] N-butyl-N-(4-fluorophenyl)carbamate Chemical compound C(C#C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)F)CCCC)=O VFTZASBGFWQIGJ-UHFFFAOYSA-N 0.000 description 1
- RVEISNXKEUSLQP-UHFFFAOYSA-N [3-(propan-2-yloxycarbonylamino)phenyl] N-ethyl-N-(2-fluorophenyl)carbamate Chemical compound CC(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=C(C=CC=C1)F)CC)=O RVEISNXKEUSLQP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000001720 action spectrum Methods 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons 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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 239000007767 bonding agent Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 150000004891 diazines Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 150000003977 halocarboxylic acids Chemical class 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 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
- 239000006028 limestone Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SBNPVCZGSKLRSJ-UHFFFAOYSA-N n-ethyl-3-fluoroaniline Chemical compound CCNC1=CC=CC(F)=C1 SBNPVCZGSKLRSJ-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 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 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003560 thiocarbamic acids Chemical class 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07C271/06—Esters of carbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
\\
Nh * TO 8790Nh * TO 8790
Diurethanen, werkwijze voor het bereiden daarvan, alsmede op deze verbindingen gebaseerde herbiciden.Diurethanes, process for their preparation, as well as herbicides based on these compounds.
De uitvinding heeft betrekking op diurethanen, op een werkwijze voor het bereiden daarvan, alsmede op herbiciden op basis van deze verbindingen.The invention relates to diurethanes, to a process for their preparation, and to herbicides based on these compounds.
De herbicide-werking van diurethanen is reeds bekend. Be-5 kende actieve verbindingen van dit type bezitten een selectieve herbicidewerking, in het bijzonder met betrekking tot Beta-bieten (Duits octrooischrift 1.567*151) of sojabonen (Duits oc-trooischrift 2.658.897)*The herbicidal action of diurethanes is already known. Known active compounds of this type have a selective herbicidal action, in particular with respect to Beta beet (German patent 1,567 * 151) or soybeans (German patent 2,658,897) *
De onderhavige uitvinding heeft tot doel de ontwikkeling 10 van een herbicide, dat een zeer goede werking bezit ten opzich te van moeilijk te bestrijden onkruidsoorten en tegelijkertijd een verdraaglijkheid, in het bijzonder ten opzichte van katoen-culturen, vertoont.The object of the present invention is to develop a herbicide which has a very good effect on difficult to control weeds and at the same time exhibits tolerability, in particular with respect to cotton cultures.
Dit probleem wordt volgens de uitvinding opgelost door een 15 herbicide, dat gekenmerkt is, doordat het ten minste een ver binding met de algemene formule 1 bevat, waarin C^-C^-alkyl of fenylethyl; Rg C^C^-alkyl, halogeen-C,,-C^-alkyl, Cg-C^-alkenyl, halogeen-C^-C^-alkenyl, Cg-C^-alkynyl of halogeen-C^-C^-alkynyl} Y waterstof of fluor en X zuurstof of zwavel 20 voorstellen.This problem is solved according to the invention by a herbicide, characterized in that it contains at least one compound of the general formula 1, in which C 1 -C 2 alkyl or phenylethyl; Rg C ^ C ^ -alkyl, halogen-C, -C1 -alkyl, Cg-C ^ -alkenyl, halogen-C ^ -C ^ -alkenyl, Cg-C ^ -alkynyl or halogen-C ^ -C ^ -alkynyl} Y represent hydrogen or fluorine and X oxygen or sulfur.
De verbindingen volgens de uitvinding vertonen verrassen-derwijze een uitstekende verdraaglijkheid in katoenculturen, hetgeen bij de bekende verbindingen met analoge constitutie niet het geval is.The compounds of the invention surprisingly exhibit excellent tolerability in cotton cultures, which is not the case with the known analogous compounds.
25 De nieuwe verbindingen vertonen bovendien.een zeer goede werking ten opzichte van moeilijk te bestrijden onkruidsoorten, zoals Amaranthus, Stellaria, Matricaria, en andere, die zowel vóór als na het opkomen bestreden kunnen worden.The new compounds also show a very good effect against difficult to control weeds, such as Amaranthus, Stellaria, Matricaria, and others, which can be controlled both before and after emergence.
Toor het bestrijden van deze zaad-onkruidsoorten zijn in 800 0 1 12 - 2 - de regel toe te passen hoeveelheden van 1 tot maximaal 5 kg actieve verbinding/ha voldoende, waarbij de verbindingen volgens de uitvinding behalve bij katoen ook bij andere culturen van verbruiksplanten, zoals soja, aardnoten, aardappelen, maïs, 5 rijst, Sorghum en graan, een selectieve werking vertonen.In order to control these seed weed species, amounts of 1 to a maximum of 5 kg of active compound / ha are generally sufficient in 800 0 1 12 - 2 - the compounds according to the invention, in addition to cotton, also being used in other cultures of consumer plants. such as soy, groundnuts, potatoes, corn, rice, sorghum, and grain, exhibit a selective action.
De verbindingen volgens de uitvinding kunnen hetzij alleen, hetzij als mengsel onderling, hetzij als mengsel met andere actieve verbindingen worden toegepast. Desgewenst kunnen andere plantenbeschermingsmiddelen of middelen ter bestrijding van 10 schadelijke organismen, al naar gelang het gewenste doel, worden toegevoegd.The compounds of the invention can be used either alone or as a mixture with one another or as a mixture with other active compounds. If desired, other plant protection agents or agents for controlling harmful organisms, depending on the desired purpose, can be added.
Yoor zover een verbreding van het werkingsspeetrum beoogd wordt, kunnen ook andere herbiciden worden toegevoegd. Zo zijn b.v. als herbicide werkzame mengcomponenten geschikt: 15 actieve verbindingen uit-de groepen der triazinen, aminotriazo-len, aniliden, diazinen, uracilen, alifatische carbonzuren en halogeencarbonzuren, gesubstitueerde benzoëzuren en aryloxycar-bonzuren, hydraziden, amiden, nitrilen, 'esters van dergelijke carbonzuren,, carbamidezuuresters en thiocarbamidezuuresters, 20 ureumderivaten, 2,3,6-trichloorbenzyloxyisopropanol en thiocy-aan-bevattende middelen en andere. Onder andere toevoegsels dient b.v. ook te worden verstaan niet-fytotoxische toevoegsels, die bij herbiciden een synergistische verhoging van de werking tot stand brengen, zoals bevochtigingsmiddelen, emulgatoren, 25 oplosmiddelen en olie-achtige toevoegsels.As far as a broadening of the action spectrum is envisaged, other herbicides can also be added. For example, e.g. suitable herbicidal mixing components: active compounds from the groups of triazines, amino triazoles, anilides, diazines, uraciles, aliphatic carboxylic acids and halocarboxylic acids, substituted benzoic acids and aryloxycarboxylic acids, hydrazides, amides, nitriles, esters of such carboxylic acids, , carbamic acid esters and thiocarbamic acid esters, urea derivatives, 2,3,6-trichlorobenzyloxyisopropanol and thiocyanates and others. Among other additives, e.g. also to be understood non-phytotoxic additives which produce a synergistic increase in the effect of herbicides, such as wetting agents, emulsifiers, solvents and oily additives.
Het verdient aanbeveling de bovenomschreven nieuwe actieve verbindingen of mengsels daarvan toe te passen in de vorm van preparaten, zoals poeders, strooisels, granulaten, oplossingen, emulsies of suspensies, onder toevoeging van vloeibare en/of 30 vaste dragers of verdunningsmiddelen en desgewenst van bevoch-tigings-, hecht-, emulgeer- en/of dispergeermiddelen.It is recommended to use the above-described new active compounds or mixtures thereof in the form of preparations, such as powders, litters, granulates, solutions, emulsions or suspensions, with the addition of liquid and / or solid carriers or diluents and, optionally, of wetted toning, bonding, emulsifying and / or dispersing agents.
Geschikte vloeibare dragers zijn b.v. water, alifatische en aromatische koolwaterstoffen, zoals benzeen, tolueen, xyleen, cyclohexanon, isoforon, dimethylsulforyde, dimethylformamide en 800 0 1 12 * Λ - 3 - voorts frakties van minerale oliën.Suitable liquid carriers are e.g. water, aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulforyde, dimethylformamide and 800 0 1 12 * Λ - 3 - further fractions of mineral oils.
Als vaste dragers zijn geschikt: minerale aarden, b.v, tonsil, silicagel, talk, kaolien, attaclay, kalksteen, kiezel-zuur en plantaardige produkten, b.v. meelsoorten.Suitable solid carriers are: mineral earths, e.g., tonsil, silica gel, talc, kaolin, attaclay, limestone, silicic acid and vegetable products, e.g. flours.
5 Als oppervlakactieve stoffen kunnen b.v. worden genoemd: calciumligninesulfonaat, polyoxyethyleen-alkylfenolethers, naftaleensulfonzuren en zouten daarvan, fenolsulfonzuren en zouten daarvan, formaldehyde-condensatieprodukten, vetalcohol-sulfaten, alsmede gesubstitueerde benzeensulfonzuren en de zou-10 ten daarvan.As surfactants, e.g. are mentioned: calcium lignin sulfonate, polyoxyethylene alkyl phenol ethers, naphthalene sulfonic acids and their salts, phenol sulfonic acids and their salts, formaldehyde condensation products, fatty alcohol sulfates, as well as substituted benzene sulfonic acids and their salts.
Het gehalte aan actieve verbinding of actieve verbindingen in de verschillende preparaten kan binnen ruime grenzen variëren. Zo bevatten de middelen b.v. ongeveer 5 tot 95 gew.$ actieve verbindingen, ongeveer 95 tot 5 gew.$ vloeibare of vaste 15 dragers, alsmede desgewenst ten hoogste 20 geir.% oppervlakac tieve verbindingen.The content of active compound or active compounds in the different preparations can vary within wide limits. For example, the agents contain e.g. about 5 to 95% by weight of active compounds, about 95 to 5% by weight of liquid or solid carriers, and optionally at most 20% by weight surfactants.
Het toepassen van de middelen kan op de gebruikelijke wijze plaatsvinden, b.v..met.water als drager in te verspuiten hoeveelheden van ongeveer 50 tot 1000 liter/ha. Toepassing van 20 de middelen bij de zogenaamde "Low-volume"- en "Ultra-Low-Volu- me"-werkwijze is even zeer mogelijk als toepassing in de vorm van zogenaamde microgranulaten.The use of the agents can take place in the usual manner, for instance with amounts of about 50 to 1000 liters / ha to be sprayed with water as a carrier. The use of the agents in the so-called "Low-volume" and "Ultra-Low-Volume" process is just as possible as use in the form of so-called micro-granulates.
Voorbeelden van de in de algemene formule door B1 voorgestelde groepen zijn b.v. methyl, ethyl, propyl, isopropyl, 25 butyl, isobutyl, sec-butyl of 2-fenylethyl en voorbeelden van de door E^ voorgestelde groepen zijn methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, allyl, propargyl, ehloor-ethyl, 1-chloormethylethyl, 4-cbloorbutynyl, 1-methylpropynyl en 4-cbloorbutenyl.Examples of the groups represented by B1 in the general formula are e.g. methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or 2-phenylethyl and examples of the groups represented by E 1 are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, allyl, propargyl, chloroethyl, 1-chloromethyl ethyl, 4-chlorobutynyl, 1-methylpropynyl and 4-chlorobutyl.
30 Van de verbindingen volgens de uitvinding munten door een uitstekende selectieve herbicide-werking in het bijzonder uit: IT-ethyl-3-fluorcarbanilzuur-(3-ethoxycarbonylaminofenyl)-ester, lT-ethyl-3-fluorcarbanilzuur-(3-methoiycarbonylaminofenyl)-ester, N-ethyl-3-fluorcarbanilzuur-^3-(1-methylethoxycarbonylamino)- 800 0 1 12 - 4 - fenyl__7-ester, E-ethyl-4-fluorcarbanilzuur-(3-ethoxycarbonyl-aminofeny1)-ester, 4-fluor-E-methylcarbanilzuur-(3-e thoxycar-bony laminof eny l) -ester, N-ethyl-3-fluorcarbanilzuur-/~3-0-methylethoxycarbonylamino)-fenyl_7-ester, F-ethyl-4-fluorcar-5 banilzuur-/”3-(l-methylethoxycarbonylamino)-fenyl_7-ester, 4- fluor-E-methylcarbanilzuur-/- 3-(l-oethylethoxycarbonylamino)-fenyl_7-ester, 3-fluσr-l!T-methylcarbanilzuuΓ-/,'"3-(l-niethylethoxy-carbonylamino)-fenylJ7-ester, E-ethyl-3,4-difluorcarbanilzuur-(3-ethoxycarbonylaminofenyl)-ester en ÏT-ethyl-2-fluorcarbanil- 10 zuur-(3-niethoxycarbonylaminofenyl)-ester.The compounds according to the invention excel in particular by their excellent selective herbicidal action: IT-ethyl-3-fluorobarbanilic acid (3-ethoxycarbonylaminophenyl) ester, 1T-ethyl-3-fluorobarbanilic acid (3-methylcarbonylaminophenyl) - ester, N-ethyl-3-fluorocarbanilic acid- ^ 3- (1-methylethoxycarbonylamino) - 800 0 1 12 - 4 - phenyl-7-ester, E-ethyl-4-fluorocarbanilic acid (3-ethoxycarbonylaminopheny1) -ester, 4- fluoro-E-methylcarbanilic acid (3-thoxycarbony laminofenyl) ester, N-ethyl-3-fluorobarbanilic acid / ~ 3-0-methyl-ethoxycarbonylamino) -phenyl-7-ester, F-ethyl-4-fluorcarcar-5 banilic acid - / "3- (1-methyl-ethoxycarbonylamino) -phenyl-7-ester, 4-fluoro-E-methylcarbanilic acid - / - 3- (1-ethyl-ethoxycarbonylamino) -phenyl-7-ester, 3-fluoro-1! -methylcarbanil-acid, / 3- (1-Nonhylethoxy-carbonylamino) -phenyl-7-ester, E-ethyl-3,4-difluororcarbanilic acid (3-ethoxycarbonylaminophenyl) ester and -T-ethyl-2-fluorocarbanilic acid (3-nonhoxycarbonylaminophenyl) -ester.
De tot nu toe niet bekende verbindingen kunnen worden be reid volgens een voor analoge verbindingen bekende methode.The previously unknown compounds can be prepared by a method known for analogous compounds.
Yolgens de uitvinding kunnen de nieuwe verbindingen worden bereid door: 15 a) verbindingen met de algemene formule 2 in tegenwoordig heid van een zuuracceptor, b.v. onder toevoeging van overmaat amine of van een anorganische base, zoals b.v, natronloog, na-triumcarbonaat, kaliumcarbonaat of een tertiaire organische base, zoals b.v. triëthylamine, om te zetten met een amine met de al- 20 gemene formule 3» of b) verbindingen met de algemene formule 4» in tegenwoordigheid van een tertiaire organische base, zoals b.v. triëthylamine of pyridine of in de vorm van alkalizouten, bij temperaturen van 0° tot 100°C te laten reageren met carbamoylchloriden met de 25 algemene formule 5» of c) verbindingen met de algemene formule 6 katalytisch, b.v. onder toepassing van nikkel in methanol, tot het overeenkomstige amine te hydrogeneren en vervolgens in tegenwoordigheid van een zuuracceptor, b.v. een anorganische base, zoals natronloog, 30 natriumcarbonaat of kaliumcarbonaat of van een tertiaire organische base, zoals b.v. triëthylamine, met verbindingen met de algemene formule 7, om te zetten in de gewenste eindprodukten en deze daarna op de gebruikelijke wijze te isoleren? waarbij in deze formules , Eg, Y en X de eerdergenoemde 800 0 1 12 - 5 - * «ir betekenissen bezitten.According to the invention, the new compounds can be prepared by: a) compounds of the general formula 2 in the presence of an acid acceptor, e.g. adding excess amine or an inorganic base, such as, for example, caustic soda, sodium carbonate, potassium carbonate or a tertiary organic base, such as e.g. triethylamine, reacting with an amine of the general formula 3 »or b) compounds of the general formula 4» in the presence of a tertiary organic base, such as e.g. triethylamine or pyridine or in the form of alkali salts, reacting with carbamoyl chlorides of the general formula 5 »at temperatures from 0 ° to 100 ° C, or c) compounds of the general formula 6 catalytically, e.g. using nickel in methanol to hydrogenate to the corresponding amine and then in the presence of an acid acceptor, e.g. an inorganic base, such as caustic soda, sodium carbonate or potassium carbonate, or of a tertiary organic base, such as e.g. converting triethylamine, with compounds of the general formula 7, into the desired end products and then isolating them in the usual manner? wherein in these formulas, Eg, Y and X the aforementioned 800 0 1 12 - 5 - 5 ir meanings.
De bereiding van de verbindingen volgens de uitvinding wordt door het volgende voorbeeld (i) nader toegelioht.The preparation of the compounds according to the invention is further illustrated by the following example (i).
Voorbeeld IExample I
5 N-Ethyl-3-fluorcarbanilzuur-/""3-(ethylthio-carbonylamino)- fenyl_/-ester-5 N-Ethyl-3-fluorocarbanilic acid - / "" 3- (ethylthio-carbonylamino) - phenyl / - ester-
In een oplossing van 13,9 S (.0,1 mol) N-ethyl-3-fluorani-line in 70 ml ethylacetaat werd onder roeren en koelen tot 10 tot 15°C een oplossing van 26,0 g (0,1 mol) chloormierezuur-10 /~3-(ethylthio-carbonylamino)-fenyl_i7’-ester in 70 ml ethylace taat en tegelijkertijd een oplossing van 13,8 g (0,1 mol) kali-umcarbonaat in 50 ml water gedruppeld. Bij 15°C werd 30 min nageroerd en vervolgens de organische fase afgescheiden en onder toevoeging van ijs met verdund zoutzuur en water gewassen. Na 15 drogen met magnesiumsulfaat werd onder verminderde druk inge dampt. Het indampresidu werd uit ethylacetaat/pentaan herkris-talliseerd.In a solution of 13.9 S (0.1 mol) N-ethyl-3-fluoroaniline in 70 ml ethyl acetate, a solution of 26.0 g (0.1) was added with stirring and cooling to 10 to 15 ° C. moles of chloroformic acid 10 / 3- (ethylthio-carbonylamino) -phenyl-17'-ester in 70 ml of ethyl acetate and at the same time drop a solution of 13.8 g (0.1 mole) of potassium carbonate in 50 ml of water. The mixture was stirred at 15 ° C for 30 min and then the organic phase was separated and washed with dilute hydrochloric acid and water under ice, with addition of ice. After drying with magnesium sulfate, evaporation was carried out under reduced pressure. The evaporation residue was recrystallized from ethyl acetate / pentane.
Opbrengst» 29,4 g » 81$ N-ethyl-3-fluorcarbanilzuur-/"*3-(ethylthiocarbonylamino)-fenyl__7-ester, smeltpunt 127°C.Yield »29.4 g» 81% N-ethyl-3-fluorocarbanilic acid - / * 3- (ethylthiocarbonylamino) -phenyl-7-ester, mp 127 ° C.
20 Op analoge wijze konden de volgende verbindingen volgens de uitvinding worden bereid»The following compounds according to the invention could be prepared in an analogous manner »
Naam van de verbinding Fysische constante 3- Fluor-N-methylcarbanilzuur-(3-methoxy- Smeltpunt» 105-107°C carbonylaminofenyl)-esterName of compound Physical constant 3- Fluoro-N-methylcarbanilic acid (3-methoxy- Melting point »105-107 ° C carbonylaminophenyl) ester
25 N-Ethyl-3-flnorcarbanilzuur-(3-methoxy- Smeltpunt» 108-109°C25 N-Ethyl-3-flororcarbanilic acid (3-methoxy- Melting point »108-109 ° C
carbonylaminofenyl)-ester N-Ethyl-3-flnorcarbanilzuur-/'-5-(methyl- Smeltpunt» 125-127°C thio-carbonylamino)-fenylJ7-estercarbonylaminophenyl) ester N-Ethyl-3-flororcarbanilic acid - / - - 5- (methyl Melting point »125-127 ° C thio-carbonylamino) -phenylJ7 ester
4- Fluor-N-methylcarbanilzuur-(3-methoxy- Smeltpunt» 96-, 97°C4- Fluoro-N-methylcarbanilic acid- (3-methoxy- Melting point »96-, 97 ° C
50 carbonylaminofenyl)-ester 4-Fluor-N-methylcarbanilzuur-/~3“(methyl- Smeltpunt» 106-108°C thio-carbonylamino)-fenyl7-ester N-Ethyl-4-fluorcarbanilzuur-/”3-(®ethyl- Smeltpunt» 143-144°C thio-carbonylamino)-fenyl_i7-e8ter 80 0 0 1 12 - 6 -50 carbonylaminophenyl) ester 4-Fluoro-N-methylcarbanilic acid- / ~ 3 "(methyl Melting point» 106-108 ° C thio-carbonylamino) -phenyl7-ester N-Ethyl-4-fluorocarbanilic acid - / "3- (®ethyl - Melting point »143-144 ° C thio-carbonylamino) -phenyl_i7-e8ter 80 0 0 1 12 - 6 -
Naam van de verbinding Fysische constante lT-Ethyl-4-fluorcarbanilzuur-(3-methoxy- Smeltpunt: 117—118°C carbonylaminofenyl)-esterName of the compound Physical constant 1T-Ethyl-4-fluorocarbanilic acid (3-methoxy- Melting point: 117—118 ° C carbonylaminophenyl) ester
H-Ethyl-4-fluorcarbanilzuur-(3-ethoxy- Smeltpunt: 76- 77°CH-Ethyl-4-fluorobarbanilic acid (3-ethoxy) Melting point: 76-77 ° C
5 carbonylaminofenyl)-esterCarbonylaminophenyl) ester
!T-Ethyl-3-fluorcarbanilzuur-(3-ethoxy- Smeltpunt: 122°CT-Ethyl-3-fluorocarbanilic acid (3-ethoxy) Melting point: 122 ° C
carbonylaminofenyl)-es tercarbonylaminophenyl) -ter
3-Fluor-H-methylcarbanilzuur-(3-ethoxy- Smeltpunt: 91- 92°C3-Fluoro-H-methylcarbanilic acid- (3-ethoxy- Melting point: 91-92 ° C
carbonylaminofenyl)-estercarbonylaminophenyl) ester
10 3-Fluor-li-methylcarbanilzuur-/~3-(niethyl- Smeltpunt: 116°C10 3-Fluoro-li-methylcarbanilic acid- / ~ 3- (nonhyl- Melting point: 116 ° C
thio-carbonylamino)-fenyl(_7-esterthio-carbonylamino) -phenyl (7-ester
3- Fluor-N-methylcarbanilzuur-/_3-(ethyl- Smeltpunt: 124-125°C3- Fluoro-N-methylcarbanilic acid - / _ 3- (ethyl- Melting point: 124-125 ° C
thio-carbonylamino)-fenyl_7-e ster 4- Fluor-ïT-methylcarbanilzuur-(3-ethoxy- η^20: 1 *5472 15 carbonylaminofenyl)-esterthio-carbonylamino) -phenyl-7-e star 4-Fluorotmethylcarbanilic acid (3-ethoxy-η ^ 20: 1 * 5472 15-carbonylaminophenyl) -ester
4-Fluor-H-(2-fenylethyl)-carbanilzuur- Smeltpunt: 137°C4-Fluoro-H- (2-phenylethyl) -carbanilic acid- Melting point: 137 ° C
(3-methoxycarbonylaminofenyl)-ester(3-methoxycarbonylaminophenyl) ester
4-Fluor-U-(2-fenylethyl)-carbanilzuür- - "Smeltpunt: 103-104°C (3-e thoxy carb onylaminof eny1)-e s t e r 20 N-Ethyl-3~fluorcarbanilzuur-/”3-(l- Smeltpunt: 9S°C4-Fluoro-U- (2-phenylethyl) -carbanilic acid- - "Melting point: 103-104 ° C (3-thoxy carbonyl aminophenyl) ester 20 N-ethyl-3-fluorocarbanilic acid - /" 3- (l- Melting point: 9S ° C
methylethoxycarbonylamino)-fenyl_7-ester N'-Ethyl-4-fluorcarbanilzuur-^""3-,(l“ Smeltpunt: 84- 86°Cmethylethoxycarbonylamino) -phenyl-7-ester N'-Ethyl-4-fluorocarbanilic acid - ^ "" 3 -, (l "Melting point: 84- 86 ° C
methylethoxycarbonylamino)-fenyl_7-estermethyl ethoxycarbonylamino) -phenyl-7-ester
4-Fluor-N-methylcarbanilzuur-/”3-0- Smeltpunt: 88°C4-Fluoro-N-methylcarbanilic acid - / ”3-0- Melting point: 88 ° C
25 methylethoxycarbonylamino)-fenylJ7-esterMethyl ethoxycarbonylamino) phenyl J7 ester
!I-Ethyl-4-fluorcarbanilzuur-/”3-(ethyl- Smeltpunt: 79°C1-Ethyl-4-fluorobarbanilic acid - / - 3- (ethyl Melting point: 79 ° C
thiocarbonylaminoj-fenyl^-esterthiocarbonylamino-phenyl-1-ester
4-Fluor-li-methylcarbanilzuur-/”3-(ethyl- Smeltpunt: 97- 99°C4-Fluoro-li-methylcarbanilic acid - / ”3- (ethyl- Melting point: 97-99 ° C
thiocarbonylamino)-fenyl_7-esterthiocarbonylamino) -phenyl-7-ester
30 3-Fluor-F-methylcarbanilzuur-/”3-(2- Smeltpunt: 142-144°C30 3-Fluoro-F-methylcarbanilic acid - / ”3- (2- Melting point: 142-144 ° C
propynyloxycarbonylamino)-fenyl_J7-esterpropynyloxycarbonylamino) phenyl J7 ester
IT-Ethyl-3-fluorcarbanilzuur-/”3-( 2- Smeltpunt: 148-150°CIT-Ethyl-3-fluorobarbanilic acid - / ”3- (2- Melting point: 148-150 ° C
propynyloxycarbonylamino)-fenyl_/-e ster 80 0 0 1 12 • + - 7 -propynyloxycarbonylamino) -phenyl _ / - e star 80 0 0 1 12 • + - 7 -
Naam van de verbinding Fysische constanteName of the connection Physical constant
4-Fluor-N-(2-fenylethyl)-carbanilzuur- Smeltpunt! 117°C4-Fluoro-N- (2-phenylethyl) -carbanilic acid- Melting point! 117 ° C
£" 3-( ethylthio-carbonylamino) -feny1J-ester3- (ethylthio-carbonylamino) -phenyl-1-ester
5 4-Fluor-N-(2-fenylethyl)-carbanilzuur- Smeltpunt: 81- 83°C5 4-Fluoro-N- (2-phenylethyl) -carbanilic acid- Melting point: 81-83 ° C
/"*3-( 1 -methyle thoxy carbonylamino) -fenyl_J -ester/ "* 3- (1-methyl-thoxycarbonylamino) -phenyl-J -ester
N-Ethyl-4-fluorcarbanilzuur-(3-allyloay- Smeltpunt: 73- 74°CN-Ethyl-4-fluorocarbanilic acid- (3-allyloay- Melting point: 73- 74 ° C
carbonylaminofenyl)-estercarbonylaminophenyl) ester
10 N-Ethyl-4-fluorcarbanilzuur-(3-propynyl- Smeltpunt: 79- 80°C10 N-Ethyl-4-fluorocarbanilic acid- (3-propynyl- Melting point: 79-80 ° C
oxycarbonylaminofenyl)-esteroxycarbonylaminophenyl) ester
4-Fluor-N-(2-fenylethyl)-carbanilzuur-(3- Smeltpunt: 81°C4-Fluoro-N- (2-phenylethyl) -carbanilic acid- (3- Melting point: 81 ° C
allyloxycarbonylaminofenyl)-ester 3-Fluor-N-(2-fenylethyl)-carbanilzuur-(3- Smeltpunt: 112-113°C 15 methoxycarbonylaminofenyl)-esterallyloxycarbonylaminophenyl) ester 3-Fluoro-N- (2-phenylethyl) -carbanilic acid- (3- Melting point: 112-113 ° C 15-methoxycarbonylaminophenyl) ester
N-Ethyl-2-fluoroarbanilzuur-(3-methojcy- Smeltpunt 106-107°CN-Ethyl-2-fluoroarbanilic acid- (3-methojcy- Melting point 106-107 ° C
carbonylaminofenyl)-estercarbonylaminophenyl) ester
N-Ethyl-3»4-difluorcarbanilzuur-(3- Smeltpunt: 121-122°CN-Ethyl-3 »4-difluorocarbanilic acid (3- Melting point: 121-122 ° C
metho3cycarbonylaminofenyl)-estermetho3cycarbonylaminophenyl) ester
20 3-Plnor-N-(2-fenylethyl)-qarbanilzuur-(3- Smeltpunt: 115°C20 3-Plnor-N- (2-phenylethyl) -carbanilic acid- (3- Melting point: 115 ° C
ethorycarbanylaminofenyl)-esterethorycarbanylaminophenyl) ester
3-Fluor-N-(2-fenylethyl)-earbanilzuur- Smeltpunt: 91- 93°C3-Fluoro-N- (2-phenylethyl) -earbanilic acid- Melting point: 91-93 ° C
C 3-( ethylthio-carbonylaaino)-fenyl_7-C 3- (ethylthio-carbonylaaino) -phenyl_7-
3-Fluor-N-methylcarbanilzuur-/-3-(1- Smeltpunt: 74- 76°C3-Fluoro-N-methylcarbanilic acid - / - 3- (1- Melting point: 74-76 ° C
25 methylethoxycarbonylamino)-fenylJ7-esterMethyl ethoxycarbonylamino) phenyl J7 ester
3-Fluor-N-methylcarbanilzuur-(3-allyloxy- Smeltpunt: 78- 80°C3-Fluoro-N-methylcarbanilic acid- (3-allyloxy- Melting point: 78-80 ° C
carbonylaminofenyl)-ester 3-Fluor-N'-ethylcarbanilzuur-(3-allyloxy- Smeltpunt: 101-103°C carbonylaminofenyl)-ester 30 4-Fluor-N-methylcarbanilzuur-(3-allyloxy- n^20: 1.5536 carbonylaminofenyl)«estercarbonylaminophenyl) ester 3-Fluoro-N'-ethylcarbanilic acid- (3-allyloxy- Melting point: 101-103 ° C carbonylaminophenyl) -ester 30 4-Fluoro-N-methylcarbanilic acid- (3-allyloxy-n ^ 20: 1.5536 carbonylaminophenyl) Ester
N-Ethyl-3-fluorcarbanilzuur-/”3-(l-chloor- Smeltpunt: 68- 70°CN-Ethyl-3-fluorobarbanilic acid - / ”3- (1-chlorine- Melting point: 68-70 ° C
methylethoxycarbonylamimO-fenyl^-ester 800 0 1 12 - 8 -methylethoxycarbonylamimO-phenyl-ester 800 0 1 12 - 8 -
Haam van de verbinding Fysische constante H-Ethyl-3t4-<iifluorcarbanilzuur-(3-ethoxy- Smeltpunt: 69- 70°0 carbonylaminofenyl)-esterName of the compound Physical constant H-Ethyl-3t4- <iifluorocarbanilic acid (3-ethoxy) Melting point: 69- 70 ° 0 carbonylaminophenyl) ester
H-Ethyl-3,4-4ifluorcarbanilzuur-/"”3- Smeltpunt: 130-132°CH-Ethyl-3,4-4ifluorocarbanilic acid - / "” 3- Melting point: 130-132 ° C
5 (methylthiocarbonylamino)-fenyl_7-ester5 (methylthiocarbonylamino) -phenyl-7-ester
2-Fluor-H-(2-fenylethyl)-carbanilzuur- Smeltpunt: 125-126°C2-Fluoro-H- (2-phenylethyl) -carbanilic acid- Melting point: 125-126 ° C
(3-methoxycarbonylaminofenyl)-ester(3-methoxycarbonylaminophenyl) ester
2-Fluor-H-(2-fenylethyl)-carbanilzuur- Smeltpunt: 128-130°C2-Fluoro-H- (2-phenylethyl) -carbanilic acid- Melting point: 128-130 ° C
(3-ethoxycarbonylamiaofenyl)-ester(3-ethoxycarbonylamiaophenyl) ester
10 2-Fluor-U-(2-fenylethyl)-carbanilzuur- Smeltpunt: 148-149°C10 2-Fluoro-U- (2-phenylethyl) -carbanilic acid- Melting point: 148-149 ° C
Z*5-C methylthiocarbonylamino)-fenylJ-esterZ * 5-C methylthiocarbonylamino) -phenyl J ester
2- Fluor-ïir-(2-fenylethyl)-carbanilzuur-/,’3- Smeltpunt: 124°C2- Fluorine (2-phenylethyl) -carbanilic acid - /, 3- Melting point: 124 ° C
(ethylthiocarbonylamino)-fenyl_7-ester -l;.(ethylthiocarbonylamino) -phenyl-7-ester -1;
15 2-Fluor-H-(2-fenylethyl)-carbanilzuur-/~3” Smeltpunt: 109-110°C15 2-Fluoro-H- (2-phenylethyl) -carbanilic acid / ~ 3 ”Melting point: 109-110 ° C
(1 -methylethoxycarbonylamino) -feny 1J- . ester(1-methylethoxycarbonylamino) -pheny 1J-. ester
3- Fluor-N-propylcarbanilzuur-(5-methoxy- Smeltpunt: -90- 92°C3- Fluoro-N-propylcarbanilic acid- (5-methoxy- Melting point: -90- 92 ° C
carbonylamino)-fenylestercarbonylamino) -phenyl ester
20 3-Fluor-H-propylcarbanilzuur-/”3-(jnethyl- Smeltpunt: 103-105°C20 3-Fluoro-H-propylcarbanilic acid - / ”3- (methyl- Melting point: 103-105 ° C
thiocarbonylamino)-fenyl__7-esterthiocarbonylamino) -phenyl-7-ester
3-Fluor-N-propylcarbanilzuur-(3-ethoxy- Smeltpunt: 103-105°C3-Fluoro-N-propylcarbanilic acid- (3-ethoxy- Melting point: 103-105 ° C
carbonylamino)-fenylestercarbonylamino) -phenyl ester
H-Ethyl-3-fluorcarbanilzuur-/—3-(1-methyl- Smeltpunt: 100-101°CH-Ethyl-3-fluorocarbanilic acid - / - 3- (1-methyl- Melting point: 100-101 ° C
25 2-propenyloxycarbonylamino)-fenylJT-ester2-propenyloxycarbonylamino) phenyl JT ester
H-Ethyl-2-fluorcarbanilzuur-/~3-(l-methyl- Smeltpunt: 109-110°CH-Ethyl-2-fluorobarbanilic acid- / ~ 3- (1-methyl- Melting point: 109-110 ° C
2-propenyloxycarbonylamino)-fenyl_7-ester H-Ethyl-4-fluorcarbanilzuur-/_3-(‘I-methyl- Smeltpunt: 73- 74°C2-propenyloxycarbonylamino) -phenyl-7-ester H-Ethyl-4-fluorobarbanilic acid - / - 3 - ("I-methyl- Melting point: 73- 74 ° C
2- propenyloxycarbonylamino)-fenyl_7~ester2-propenyloxycarbonylamino) -phenyl-7-ester
30 H-Butyl-3-fluorcarbanilzuur-(3-methoxy- Smeltpunt: 79- 80°C30 H-Butyl-3-fluorocarbanilic acid- (3-methoxy- Melting point: 79-80 ° C
carbonylamino)-fenylestercarbonylamino) -phenyl ester
3- Fluor-H-methylcarbanilzuur-/”3-(2- Smeltpunt: 94- 95°C3- Fluoro-H-methylcarbanilic acid - / ”3- (2- Melting point: 94-95 ° C
methylpropoxycarbonylamino)-fenyl_7-ester 80 0 0 1 12 _ 0 * - 9 -methylpropoxycarbonylamino) -phenyl-7-ester 80 0 0 1 12 _ 0 * - 9 -
Naam van de verbinding Fysische constante 4-Fluor-N-(2-feuylethyl)-carbaailzuur-/~3- 0^20: 1.5578 (1-methyl-2-propeayloxycarboaylamiao)-fenyl_7-ester 5 3-Fluor-ïï-(2-feaylethyl)-carbaailzuur-/""3- a^20: 1.5632 (1 -methyl-2-propeayloxycarboaylamiao) -fenyl_7-ester 3- Fluor-N-methylearbaailzuur-/"’3-(1-methyl a^20: 1.55Ö9 -2-propenyloxyearboaylamiao)-feayl_7-ester 10 4-Fluor-F-methylcarbaailzuur-/~3-(1-methyl a^20: 1.5465 -2-propenylo3cycarbonylamino)-fenyl_i7-ester lf-Butyl-4“fluorcarbaailzuur-^"3-( 1 -methyl- ^20: 1.5298 2-propenyloxycarboaylamiao)-fenyl_7-ester 4- Fluor-N-methylcarbaailzuur-^"3-(2-methyl*a^20s 1.5313 15 propoxycarboaylamiao)-feayl_7-esterName of the compound Physical constant 4-Fluoro-N- (2-feuyl ethyl) -carboxylic acid- ~ 3- 0 ^ 20: 1.5578 (1-methyl-2-propeayloxycarboaylamiao) -phenyl-7-ester 5 3-Fluoro-1-( 2-pheaylethyl) -carbic acid - / "" 3- a ^ 20: 1.5632 (1-methyl-2-propeayloxycarboaylamiao) -phenyl-7-ester 3- Fluoro-N-methyl-carboxylic acid - / "" 3- (1-methyl a ^ 20 : 1.55O9 -2-propenyloxyearboaylamiao) -pheayl-7-ester 10 4-Fluoro-F-methylcarboxylic acid- / ~ 3- (1-methyl a ^ 20: 1.5465 -2-propenylo3cycarbonylamino) -phenyl-7-ester 1-Butyl-4 "fluorocarboxylic acid - ^ "3- (1-methyl- ^ 20: 1.5298 2-propenyloxycarboaylamiao) -phenyl-7-ester 4- Fluoro-N-methylcarboxylic acid - ^" 3- (2-methyl * a ^ 20s 1.5313-propylcarboaylamiao) -pheayl_7-ester
4-Fluor-N-propylcarbaailzuur-^”3-(l-methyl Smeltpuat: 75- 76°C4-Fluoro-N-propyl carboxylic acid - ^ ”3- (1-methyl Melting point: 75-76 ° C
-2-propenyloxycarboaylamiao)-£eayl_7-ester-2-propenyloxycarboaylamiao) - eayl_7-ester
N-Ethyl-2-fluorcarbaailzuur-(3-ethoxy- Smeltpuat: 151 —153°CN-Ethyl-2-fluorocarboxylic acid (3-ethoxy- Melting point: 151 - 153 ° C
carbonylamiaofeayl)-estercarbonylamiaopheayl) ester
20 iï-Ethyl-2-fluorcarbaailzuur-(3-(methyl- Smeltpuat: 160-162°C20 i-Ethyl-2-fluorocarboxylic acid (3- (methyl- Melting point: 160-162 ° C
thiocarboaylamiao)-feayl)-esterthiocarboaylamiao (pheayl) ester
N-Ethyl-2-fluorcarbaailzuur-(3-ethylthio- Smeltpuat: 146-147°CN-Ethyl-2-fluorocarboxylic acid (3-ethylthio- Melting point: 146-147 ° C
carboaylamiao)-feayl)-estercarboaylamiaO-pheayl) ester
ÏT-Ethyl-2-fluorcarbaailzuur- (3-(1 -methyl- Smeltpuat: 126-127°CIT-Ethyl-2-fluorocarboxylic acid (3- (1-methyl- Melting point): 126-127 ° C
25 ethoxycarboaylamiao)-feayl)-esterEthoxycarboaylamiaO-pheayl) ester
N-Ethyl-2-fluorcarbaailzuur-(3-(2-propy- Smeltpuat: 150°CN-Ethyl-2-fluorocarboxylic acid- (3- (2-propy- Melting point: 150 ° C)
ayloxycarboaylamiao)-feay1)-esterayloxycarboaylamiao) -feay1) -ester
2-Fluor-N-(2-feaylethyl)-carbaailzuur-(3- Smeltpuat: 72- 73°C2-Fluoro-N- (2-feaylethyl) -carboxylic acid- (3-Melting point: 72-73 ° C
allyloxycarboaylamiao)-feayl)-esterallyloxycarboaylamiao) -feayl) -ester
30 2-Fluor-Ii-(2-feaylethyl)-carbaailzuur-(3- Smeltpuat: 57- 58°C30 2-Fluoro-II- (2-feaylethyl) -carboxylic acid- (3-Melting point: 57- 58 ° C
(2-me thylpropoxycarboay lamiao.) -f eayl) -ester 4-Fluor-N-propylcarbaailzuur-3-(methoxy- β^20: 1.5345 carboaylamiaofeayl)-ester 80 0 0 1 12 - 10 -(2-methylpropoxycarboay lamiao.) -F eayl) ester 4-Fluoro-N-propylcarboxylic acid 3- (methoxy- β ^ 20: 1.5345 carboaylamiaopheayl) ester 80 0 0 1 12 - 10 -
Faam van de verbinding Fysische constanteFame of the connection Physical constant
4-Fluor-N-propylcarbanilzuur-3-(ethoxy- Smeltpunt: 64- 66°C4-Fluoro-N-propylcarbanilic acid-3- (ethoxy- Melting point: 64- 66 ° C
carhonylaminofenyl)-ester F-Butyl-4-fluorcarbanilzuur-3-(methoxy- n^20: 1.5322 5 carbonylaminofenyl)-ester F-Butyl-4-fluorcarbanilzuur-3-(ethoxy- n.^20 ï 1.5305 carbonylaminofenyl)-e stercarhonylaminophenyl) ester F-Butyl-4-fluorobarbanilic acid-3- (methoxy-n-20: 1.5322 5-carbonylaminophenyl) -ester F-Butyl-4-fluorobarbanilic acid-3- (ethoxy-n. ^ 20 ï 1.5305 carbonylaminophenyl) -e star
4-Fluor-F-butylcarbanilzuur-(3-(l-methyl- Smeltpunt: 81- 83°C4-Fluoro-F-butylcarbanilic acid- (3- (1-methyl- Melting point: 81-83 ° C)
ethoxycarbonylamino)-fenyl)-esterethoxycarbonylamino) -phenyl) ester
10 4-Fluor-F-butylcarbanilzuur-(3-ethylthio- Smeltpunt: 73- 75°C10 4-Fluoro-F-butylcarbanilic acid- (3-ethylthio- Melting point: 73-75 ° C
carbonylamino)-f eny1)-e ster F-Butyl-4-fluorcarbanilzuur-(3-(2- n^20: 1.5439 propynyloxycarbonylamino)-fenyl)-estercarbonylamino) -f eny1) -e star F-Butyl-4-fluorobarbanilic acid- (3- (2- n ^ 20: 1.5439 propynyloxycarbonylamino) -phenyl) -ester
4-Fluor-F-propylcarbanilzuur-(3-(ethyl- Smeltpunt: 53- 55°C4-Fluoro-F-propylcarbanilic acid- (3- (ethyl- Melting point: 53- 55 ° C
15 thiocarbonylamino)-fenyl)-ester 4-Fluor-3S’-propylcarbanilzuur-(3-(2- n^20: 1 · 54^1 propynyloxycarbonylamino)-fenyl)-ester15 thiocarbonylamino) -phenyl) ester 4-Fluoro-3S-propylcarbanilic acid- (3- (2- n ^ 20: 1 54 ^ 1 propynyloxycarbonylamino) -phenyl) ester
N-Butyl-4-fluorcarbanilzuur-(3-(methyl- Smeltpunt: 85- 89°CN-Butyl-4-fluorocarbanilic acid- (3- (methyl- Melting point: 85-89 ° C
thiocarbonylamino)-fenyl)-e sterthiocarbonylamino) -phenyl) -e star
20 2-Fluor-F-(2-fenylethyl)-carbanilzuur- Smeltpunt: 93- 94°C20 2-Fluoro-F- (2-phenylethyl) -carbanilic acid- Melting point: 93-94 ° C
5-(2-propynyloxycarbonylamino)-feny1_7-ester5- (2-propynyloxycarbonylamino) -phenyl-7-ester
De verbindingen volgens de uitvinding zijn oplosbaar in aceton, cyclohexanon, isoforon, tetrahydrofuran, dimethylform-25 amide, dimethylsulfoxyde en ethylacetaat.The compounds of the invention are soluble in acetone, cyclohexanone, isophorone, tetrahydrofuran, dimethylformamide, dimethyl sulfoxide and ethyl acetate.
De nu volgende voorbeelden dienen ter toelichting van de toepassingsmogelijkheden, alsmede ter vergelijking met bekende verbindingen.The following examples serve to illustrate the applications, as well as for comparison with known compounds.
Voorbeeld IIExample II
30 In een broeikas werden de in de hierna volgende tabel ver melde verbindingen volgens de uitvinding in een toe te passen hoeveelheid van 5 kg actieve verbinding/ha, geëmulgeerd in 500 liter water/ha, op Brassica en Solanum als te toetsen planten na het opkomen gespoten. Drie weken na de behandeling werd het 80 0 0 1 12 • * - 11 - behandelingsresultaat gewaardeerd, waarbij O = geen werking en 4 * vernietiging van de planten betekent.In a greenhouse, the compounds of the invention listed in the table below were emulsified in 500 liters of water / ha to be used as test plants after emergence in an amount of 5 kg of active compound / ha to be used. sprayed. Three weeks after the treatment, the 80 0 0 1 12 • * - 11 - treatment result was valued, where O = no effect and 4 * means destruction of the plants.
5 Zoals uit de tabel blijkt werd een vernietiging van de proefplanten bereikt.As shown in the table, destruction of the test plants was achieved.
Verbindingen volgens de uitvinding Solanum Brassica 3- Fluor-N-methylcarbanilzuur-(3-methoxy- carbonylaminofenyl)-ester 4 4 10 N-Ethyl-3-fluorcarbanilzuur-(3-methoxy- carbonylaminofenyl)-ester 4 4 N-Ethyl-3-fluorcarbanilzuur-/"" 3-(®ethyl-thio-carbonylamino)-fenyl__7-ester 4 4 4- Fluor-ft-methylcarbanilzuur-(3-methoxy- 15 carbonylaminofenyl)-ester 4 4 4-Fluor-ÏT-methylcarbanilzuur-/'” 3-(®ethyl-thio-carbonylamino)-fenyl_7-ester 4 4 N-Ethyl-4-fluorcarbanilzuur-/_ 3“(®ethyl-thio-carbonylamino)-fenyl_7-ester 4 4 20 ïï-Ethyl-4-fluorcarbanilzuur-(3-methoxy- carbonylaminofenyl)-ester 4 4 N-Ethyl-4-fluorcarbanilzuur-(3~ethoxy- carbonylaminofenyl)-ester 4 4 !T-Ethyl-3-fluoroarbanilzuur-(3-ethoxy-25 carbonylaminofenyl)-ester 4 4 3-Fluor-N-methylcarbanilzuur-(3-ethoxy- carbonylaminofenyl)-ester 4 4 3- Fluor-rr-methylcarbanilzuur-/"" 3-(methyl- thio-carbonylamino)-fenyl_7-ester 4 4 30 3-FlTior''ft*,®e‘fchylcarbanilzuur-/"" 3-(ethyl- thio-carbonylamino)-fenyl_7-ester 4 4 4- Fluor-ÏI-methylcarbanilzuur-( 3-ethoxy- carbonylaminofenyl)-ester 4 4 800 0 1 12 - 12 -Compounds according to the invention Solanum Brassica 3-Fluoro-N-methylcarbanilic acid (3-methoxy-carbonylaminophenyl) ester 4 4 10 N-Ethyl-3-fluorocarbanilic acid (3-methoxy-carbonylaminophenyl) -ester 4 4 N-Ethyl-3 -Fluorocarbanilic acid- / "" 3- (ethylethyl-thio-carbonylamino) -phenyl-7-ester 4 4 4-Fluoro-ft-methylcarbanilic acid (3-methoxy-carbonylaminophenyl) -ester 4 4 4-Fluoro-IT-methylcarbanilic acid- / '”3- (ethylethyl-thio-carbonylamino) -phenyl-7-ester 4 4 N-Ethyl-4-fluorobarbanilic acid - / 3 3“ (®-ethyl-thio-carbonylamino) -phenyl-7-ester 4 4 20 ï-Ethyl- 4-Fluorecarbanilic acid (3-methoxy-carbonylaminophenyl) ester 4 4 N-Ethyl-4-fluorocarbanilic acid (3-ethoxy-carbonylaminophenyl) -ester 4 4-T-Ethyl-3-fluoroarbanilic acid (3-ethoxy-25-carbonylaminophenyl) ) -ester 4 4 3-Fluoro-N-methylcarbanilic acid- (3-ethoxy-carbonylaminophenyl) -ester 4 4 3-Fluoro-rr-methylcarbanilic acid- / "" 3- (methylthio-carbonylamino) -phenyl-7-ester 4 4 30 3-FlTior'ft *, ®e'fchylcarbanilic acid- / "" 3- (ethylthio-carbonylamino) -phenyl-7-ester 4 4 4-Fluoro-II-methylcarbanil acid (3-ethoxy-carbonylaminophenyl) ester 4 4 800 0 1 12 - 12 -
Verbindingen volgens de uitvinding Solanum Brassica 4-Fluor-H-(2-fenylethy1)-carbanilzuur- (3-methoxycarbonylaminofenyl)-ester 4 4 4-Fluor-ïf-( 2-fenylethyl) -carbanilzuur-5 (3-ethoxycarbonylaminofenyl)-ester 4 4 N-Ethyl-3-fluorcarbanilzuur-/” 3-0-methyl-ethoxycarbonylamino)-fenyl_7-ester 4 4 ÏT-Ethyl-4-fluorcarbanilzuur-/""3-( 1-methyl-ethoxycarbonylamino)-fenyl_7-ester 4 4 10 4-Fluor-ïï-methylcarbanilzuur-/- 3-(l-methyl- ethoxycarbonylamino)-fenylJ7-ester 4 4 ïf-Ethyl-4-fluorcarbanilzuur-/"" 3-(ethylthio-carbonylamino)-fenyl_7-ester 4 4 4-Fluor-H-methylcarbanilzuur-/"’ 3-(ethyl- 15 thiocarbonylamino)-fenyl_7-ester 4 4 3- Fluor-N-methylcarbanilzuur-/"" 3-(2- propynyloxycarbonylamino)-fenyl_J7-ester 4 4 U--Ethyl-3-fluorcarbanilzuur-/"’3-(2- propynyloxycarbonylamino)-fenyl_7-ester 4 4 20 4-Fluor-ïï-(2-fenylethyl )-carbanilzuur-/~* 3- ethylthiocarbonylamino)-fenyl_7-ester 4 4 4- Fluor-IT-( 2-f enylethyl)-carbanilzuur-/~ 3- (l-methylethoxycar'bonylamino)-fenyl_i7-ester 4 4 N-Ethyl-4-fluorcarbanilzuur-(3-allyloxy- 25 carbonylaminofenyl)-ester 4 4 U-Ethyl-4-fluorcarbanilzuur-(5-propynyl-oxycarbonylaminofenyl)-ester 4 4 4-Fluor-N-(2-fenylethyl)-carbanilzuur-(3-allyloxycarbonylaminofenyl)-ester 4 4 30 3-Fluor-ïï-(2-fenylethyl)-carbanilzuur-(3- methoxycarbonylaminofenyl)-ester 4 4 3-Fluor-N-methylcarbanilzuur-/~ 3-(1-methyl-ethoxycarbonylamino)-fenyl_7-ester 4 4 80 0 0 1 12 - 13 -Compounds according to the invention Solanum Brassica 4-Fluoro-H- (2-phenylethy1) -carbanilic acid- (3-methoxycarbonylaminophenyl) ester 4 4 4-Fluorofly- (2-phenylethyl) -carbanilic acid-5 (3-ethoxycarbonylaminophenyl) - ester 4 4 N-Ethyl-3-fluoro-carbanilic acid- / 3-0-methyl-ethoxycarbonylamino) -phenyl-7-ester 4 4-Ethyl-4-fluoro-carbanilic acid - / "" 3- (1-methyl-ethoxycarbonylamino) -phenyl_7- ester 4 4 10 4-Fluoro-1-methylcarbanilic acid - / - 3- (1-methyl-ethoxycarbonylamino) -phenyl-7-ester 4 4-Ethyl-4-fluorocarbanilic- / "" 3- (ethylthio-carbonylamino) -phenyl-7- ester 4 4 4-Fluoro-H-methylcarbanilic acid- / "3- (ethyl-thiocarbonylamino) -phenyl-7-ester 4 4 3-Fluoro-N-methylcarbanilic-acid /" "3- (2-propynyloxycarbonylamino) -phenyl_J7-ester 4 4 U - Ethyl-3-fluorocarbanilic acid - / "3- (2-propynyloxycarbonylamino) -phenyl-7-ester 4 4 20 4-Fluoro-2- (2-phenylethyl) -carbanilic- / ~ * 3-ethylthiocarbonylamino) - phenyl-7-ester 4 4 4-Fluoro-IT- (2-phenylethyl) -carbanilic acid- ~ 3- (1-methyl-ethoxycarbonylamino) -phenyl-7-ester 4 4 N-Ethyl-4-fluoro carbanilic acid (3-allyloxy-25-carbonylaminophenyl) -ester 4 4 U-Ethyl-4-fluorobarbanilic acid (5-propynyl-oxycarbonylaminophenyl) -ester 4 4 4-Fluoro-N- (2-phenylethyl) -carbanilic acid- (3- allyloxycarbonylaminophenyl) ester 4 4 30 3-Fluoro-2- (2-phenylethyl) -carbanilic acid- (3-methoxycarbonylaminophenyl) ester 4 4 3-Fluoro-N-methylcarbanilic acid / ~ 3- (1-methyl-ethoxycarbonylamino) - phenyl_7-ester 4 4 80 0 0 1 12 - 13 -
Verbindingen volgens de uitvinding Solanmn Brassica 3-Fluor-IT-methylcarbanilzuur-(3-allyl- oxycarbonylaminofenyl)-ester 4 4 3- Fluor-!i-etliylcarbanilzuur-(3-allyl- 5 oxycarbonylaminofenyl)-ester 4 4 4- Fluor-N-methylcarbanilzuur-(3-allyl- oxycarbonylaminofenyl)-ester 4 4 IT-Ethyl-3-i“luorcarbanilzuur-/"” 3-(1-chloormethylethoxycarbonylamino)-fenyl_7-10 ester 4 4 ïï-Ethyl-2-fluorcarbanilzuur-(3-methoxy- carbonylaminofenyl)-ester 4 4 N-Etliyl-3,4“difluorcarbanilzuur-(3- methoxycarbonylaminofenyl)-ester 4 4 15 3-Fluor-!i-( 2-fenylethyl)-carbanilzuur- (3-ethoxycarbonylaminofenyl)-ester 4 4 5- Fluor-N-(2-fenylethyl)-earbanilzuur-/” 3- (ethylthiocarbonylamino)-fenyl_7-ester 4 4 3-Fluor-ïï-(2-fenylethyl)-carbanilzuur-/”3- 20 (ethylthiocarbonylamino)-fenyl_7-ester 4 4 N-Ethyl-3,4-difluorcarbanilzuur-(3-ethory-carbonylaainofenyl)-ester 4 4 ïï-Ethyl-3,4-difluorcarbanilzuur-/-3- (methylthiocarbonylamino)-fenyl_7-ester 4 4 25 2-Fluor-N-(2-fenylethyl)-carbanilzuur-(3- methoxycarbonylaminofenyl)-ester 4 4 2-Fluor-]T-(2-fenyletiiyl)-carbanilzuur-(3-ethoxycarbonylaminofenyl)-ester 4 4 2-Flnor-ïï-(2-fenylethyl)-carbanilzuur-/” 3-30 (methylthiocarbonylamino)-fenyl_7-ester 4 4 2-Fluor-N-(2-fenylethyl)-carbanilzuur-/~3-(ethyltbiocarbonylamino)-fenyl^-ester 4 4 2-Fluor-N-(2-fenylethyl)-carbanilzuur-/” 3-(1-methylethorycarbonylamino)-fenyl-7'-ester 4 4 80 0 0 1 12 - 14 -Compounds according to the invention Solanmn Brassica 3-Fluoro-IT-methylcarbanilic acid (3-allyl-oxycarbonylaminophenyl) ester 4 4 3-Fluoro-1-etliylcarbanilic acid (3-allyl-oxycarbonylaminophenyl) ester 4 4 4-Fluor- N-methylcarbanilic acid (3-allyl-oxycarbonylaminophenyl) ester 4 4 IT-Ethyl-3-i-luorcarbanilic acid- / "3- (1-chloromethyl-ethoxycarbonylamino) -phenyl-7-10 ester 4 4-Ethyl-2-fluorocarbanilic acid- (3-methoxy-carbonylaminophenyl) ester 4 4 N-Etliyl-3,4 "difluorocarbanilic acid- (3-methoxycarbonylaminophenyl) ester 4 4 15 3-Fluoro-! I- (2-phenylethyl) -carbanilic acid- (3-ethoxycarbonylaminophenyl) ) -ester 4 4 5- Fluoro-N- (2-phenylethyl) -earbanilic acid- / "3- (ethylthiocarbonylamino) -phenyl-7-ester 4 4 3-Fluoro-1- (2-phenylethyl) -carbanilic acid - /" 3- 20 (ethylthiocarbonylamino) -phenyl-7-ester 4 4 N-Ethyl-3,4-difluorocarbanilic acid- (3-ethory-carbonylaainophenyl) -ester 4 4-Ethyl-3,4-difluorocarbanilic acid - / - 3- (methylthiocarbonylamino) -phenyl_7 ester 4 4 25 2-Fluoro-N- (2-phenylethyl) -carbanilic acid- (3-methoxycarbonylaminophenyl) -e star 4 4 2-Fluoro-] T- (2-phenyletiiyl) -carbanilic acid- (3-ethoxycarbonylaminophenyl) ester 4 4 2-Flnor-1- (2-phenylethyl) -carbanilic acid- / ”3-30 (methylthiocarbonylamino) - phenyl-7-ester 4 4 2-Fluoro-N- (2-phenylethyl) -carbanilic acid- / ~ 3- (ethyl-biocarbonylamino) -phenyl-ester 4 4 2-Fluoro-N- (2-phenylethyl) -carbanilic- / 3 - (1-methylethorycarbonylamino) -phenyl-7'-ester 4 4 80 0 0 1 12 - 14 -
Verbindingen volgens de uitvinding _ Solanum Brassica 2-Fluor-N-(2-fenylethylJ-carbanilzuur-/"" 3“ (2-propynyloxycarbonylamino)-fenyl_7-ester 4 4 Iï-Ethyl-2-fliiorcarbanilzuur-(3-etkoxy-* 3 carbonylaminofenyl)-ester 4 4 ET-Ethyl-2-fluorcarbanilzuur-(3-iaethyl-thiocarbonylamino)-fenyl)-ester 4 4 N-Ethyl-2-fluorcarbanilzuur-(3-(ethyl- thiocarbonylamino)-fenyl)-ester 4 4 10 N-Ethyl-2-fluorcarbanilzuur-(3-(1 -methyl- ethoxycarbonylamino)-fenyl)-ester 4 4 U-Ethyl-2-fluorcarbanilztrar-(3-(2-propy-nyloxycarbonylamino)-fenyl)-ester 4 4 2-Fluor-ïf-( 2-f enylethyl)-carbanilzuur-( 3-15 allyloxycarbonylamino)-fenyl)-ester 4 4 2-Fluor-IT-( 2-fenylethyl)-carbanilzuur-( 3-(2-methylpropoxycarbonylamino)-fenyl)-ester 4 4 4-Fluor-H-propylcarbanilzuur-3-(methoxy-carbonylaminofenyl)-ester 4 4 20 4-ï’luor-H-propylcarbanilzuur-3-(ethoxy- carbonylaminofenyl)-ester 4 4 N-Butyl-4-flnorcarbanilzuur-3-(methoxy- carbonylaminofenyl)-ester 4 4 ïï-Butyl-4-fluoroarbanilzuur-3-(ethoxy-25 carbonylaminofenyl)-ester 4 4 4-Fluor-IT-butylcarbanilzuur-( 3-( 1 -methyl-ethoxycarbonylamino)-fenyl)-ester 4 4 4-Fluor-N-butylcarbanilzuur-(3-ethylthio-carbonylamino)-fenyl)-ester 4 4 30 ïï-Butyl-4-fluorcarbanilzuur-(3-(2- propynyloxycarbonylamino)-fenyl)-ester 4 4 4-Fluor-U-propylcarbanilzuur-(3-(ethy1- thiocarbonylamino)-fenyl)-ester 4 4 80 0 0 1 12 «Γ - 15 -Compounds according to the invention - Solanum Brassica 2-Fluoro-N- (2-phenylethyl-J-carbanilic acid- / "" 3 "(2-propynyloxycarbonylamino) -phenyl-7-ester 4 4-Ethyl-2-flioriorcarbanilic acid- (3-etkoxy- * 3-carbonylaminophenyl) ester 4 4 ET-Ethyl-2-fluorocarbanilic acid (3-iaethyl-thiocarbonylamino) -phenyl) -ester 4 4 N-Ethyl-2-fluorocarbanilic acid (3- (ethyl-thiocarbonylamino) -phenyl) -ester 4 4 10 N-Ethyl-2-fluorocarbanilic acid- (3- (1-methyl-ethoxycarbonylamino) -phenyl) -ester 4 4 U-Ethyl-2-fluorocarbanilztrar- (3- (2-propy-nyloxycarbonylamino) -phenyl) - ester 4 4 2-Fluoro-2- (2-phenyl-ethyl) -carbanilic acid- (3-15 allyloxycarbonylamino) -phenyl) -ester 4 4 2-Fluoro-IT- (2-phenylethyl) -carbanilic acid- (3- (2 -methylpropoxycarbonylamino) -phenyl) ester 4 4 4-Fluoro-H-propylcarbanilic acid-3- (methoxy-carbonylaminophenyl) ester 4 4 20 4-Fluoro-H-propylcarbanilic acid 3- (ethoxy-carbonylaminophenyl) -ester 4 4 N-Butyl-4-flororcarbanilic acid-3- (methoxy-carbonylaminophenyl) ester 4 4-Butyl-4-fluoroarbanilic acid-3- (ethoxy-25-carbonylaminophenyl) ester 4 4 4-Fluoro-IT-butylcarbanilic acid (3- (1-methyl-ethoxycarbonylamino) -phenyl) -ester 4 4 4-Fluoro-N-butylcarbanilic acid (3-ethylthio-carbonylamino) -phenyl) -ester 4 4 30 Butyl 4-fluorocarbanilic acid (3- (2-propynyloxycarbonylamino) phenyl) ester 4 4 4-Fluoro-U-propylcarbanilic acid (3- (ethyl-1-thiocarbonylamino) phenyl) ester 4 4 80 0 0 1 12 « Γ - 15 -
Verbindingen volgens de uitvinding Solanum Brassica 4-Fluor-N-propylcarbanilzuur-(3-( 2- propynyloxycarbonylamino)-fenyl)-ester 4 4 N-Butyl-4-fluorcarbanilzuur-(3-(inethyl-5 thiocarbonylamino)-fenyl)-ester 4 4 ÏT-Ethyl-3-f’luorcarbanilzuur-( 3-( 1 -methyl- 2-propenyloxycarbonylamino)-fenyl)-ester 4 4 N-Ethyl-2-fluorcarbanilzuur-(3-(1-methyl- 2-propenylorycarbonylamino)-fenyl)-ester 4 4 10 U-Ethyl-4-fluorcarbanilzuur-(3-(1-methyl- 2- propenyloxycarbonylainino)-fenyl)-ester 4 4 N-Butyl-3-fluorcarbanilzuur-(3-methoxy-carbonylamino)-fenylester 4 4 3- Fluor-ÏT-methylcarbanilzuur-(3-( 2-methyl- 15 propoxycarbonylamino)-fenyl)-ester 4 4 4- Fluor-IT-( 2-fenylethyl)-oarbanilzuur-(3-(1-methyl-2-propenyloxycarbonylamino)- fenyl)-ester 4 4 3 -Fluor-ïf- (2-f eny le thy 1) - carbanil zuur- (3 -20 (1 -methyl-2-propenyloxycarbonylainino)- fenyl)-ester 4 4 3- Fluor-N-iaethylcarban.ilzuur-( 3-( 1 -methyl- 2-propenyloxyearbonylamino)-fenyl)-ester 4 4 4- Fluor-N-methylcarbaailzuur-(3-(l-methyl- 25 2-propenyloxycarbonylamino)-fenyl)-ester 4 4 H'-Butyl-4-fluorcarbanilzuur-(3-(l -methyl- 2- propenyloxycarbonylamino)-fenyl)-ester 4 4 4-Fluor-N-methylcarbanilzuur-(3-C 2-methyl-propoxycarbonylamino)-fenyl)-ester 4 4 30 3-Fluor-N-propylcarbanilzuur-(3-methoxy- carbonylamino)-fenylester 4 4 3- Fluor-N-propylcarbanilzuur-(3-(methyl- thiocarbonylamino)-fenyl)-ester 4 4 80 0 0 1 12 - 16 -Compounds according to the invention Solanum Brassica 4-Fluoro-N-propylcarbanilic acid- (3- (2-propynyloxycarbonylamino) -phenyl) -ester 4 4 N-Butyl-4-fluorocarbanilic acid- (3- (inethyl-5-thiocarbonylamino) -phenyl) - ester 4 4--Ethyl-3-fluorocarbanilic acid- (3- (1-methyl-2-propenyloxycarbonylamino) -phenyl) -ester 4 4 N-Ethyl-2-fluorocarbanilic acid- (3- (1-methyl-2- propenylorycarbonylamino) -phenyl) ester 4 4 10 U-Ethyl-4-fluorobarbanilic acid- (3- (1-methyl-2-propenyloxycarbonylainino) -phenyl) -ester 4 4 N-Butyl-3-fluorobarbanilic acid (3-methoxy-) carbonylamino) -phenyl ester 4 4 3-Fluoro-IT-methylcarbanilic acid- (3- (2-methyl-propoxycarbonylamino) -phenyl) -ester 4 4 4-Fluorine-IT- (2-phenylethyl) -oarbanilic acid- (3- ( 1-methyl-2-propenyloxycarbonylamino) -phenyl) -ester 4 4 3 -Fluoro-1- (2-phenyle thy 1) -carbanil acid- (3 -20 (1-methyl-2-propenyloxycarbonylainino) -phenyl) ester 4 4 3- Fluoro-N-iaethylcarbanililic acid- (3- (1-methyl-2-propenyloxyearbonylamino) -phenyl) -ester 4 4 4- Fluoro-N-methylcarboxylic acid- (3- (1-methyl- 25 2-prope nyloxycarbonylamino) -phenyl) -ester 4 4 H'-Butyl-4-fluorobarbanilic acid- (3- (1-methyl-2-propenyloxycarbonylamino) -phenyl) -ester 4 4 4-Fluoro-N-methylcarbanilic acid- (3-C 2 -methyl-propoxycarbonylamino) -phenyl) -ester 4 4 30 3-Fluoro-N-propylcarbanilic acid (3-methoxy-carbonylamino) -phenyl ester 4 4 3-Fluoro-N-propylcarbanilic acid (3- (methylthiocarbonylamino) -phenyl ) -ester 4 4 80 0 0 1 12 - 16 -
Verbindingen volgens de uitvinding Solanum Brassica 3- Fluor-N-propylcarbanilzuur-(3-etho:cy- carbonylamino)-fenylester 4 4Compounds of the invention Solanum Brassica 3-Fluoro-N-propylcarbanilic acid (3-etho: cyccarbonylamino) phenyl ester 4 4
Voorbeeld IIIExample III
5 In een broeikas werden de in de hierna volgende tabel ver melde verbindingen volgens de uitvinding in een toe te passen hoeveelheid van 5 kg actieve verbinding/ha, geëmulgeerd in 600 liter water/ha, op Brassica en Solanum als proefplanten vóór het opkomen gespoten. Drie weken na de behandeling werd het be-10 handelingsresultaat gewaardeerd, waarbij 0 = geen werking en 4 * vernietiging van de planten betekent.In a greenhouse, the compounds of the invention listed in the table below were sprayed onto Brassica and Solanum as pre-emergence test plants in an amount of 5 kg of active compound / ha to be used, emulsified in 600 liters of water / ha. The treatment result was evaluated three weeks after the treatment, where 0 = no effect and 4 * means destruction of the plants.
Zoals uit de tabel blijkt, werd een vernietiging van de 15 proefplanten bereikt.As shown in the table, destruction of the 15 test plants was achieved.
Verbindingen volgens de uitvinding Solanum Brassica 4- Fluor-N-methylcarbanilzuur-(3-methoxy- carbonylaminofenyl)-ester '4 - — 4 U-Ethyl-4-fluorcarbanilzuur-(3-methoxy- 20 carbonylaminofeny1)-ester 4 4 IT-Ethyl-4-fluorcarbanilzuur-(3-ethoxy- carbonylaminofenyl)-ester 4 4 4-Fluor-lf-methylcarbanilzuur-(3-ethoxy- carbonylaminofenyl)-ester 4 4 25 N-Ethyl-4-fluorcarbanilzuur-/”~3-( 1 -methyl- ethoxycarbonylamino)-fenyl_7-ester 4 4Compounds according to the invention Solanum Brassica 4- Fluoro-N-methylcarbanilic acid (3-methoxy-carbonylaminophenyl) -ester 4 - 4 U-Ethyl-4-fluorobarbanilic acid (3-methoxy-carbonylaminophenyl) -ester 4 4 IT- 4-Fluoro-1-methylcarbanilic acid (3-ethoxy-carbonylaminophenyl) ester 4 4 25 N-Ethyl-4-fluorocarbanilic acid - / ~ 3- (1-methyl-ethoxycarbonylamino) -phenyl-7-ester 4 4
Onbehandeld O 0Untreated O 0
Voorbeeld IVExample IV
In een broeikas werden de in de navolgende tabel genoemde 30 planten na het opkomen met de vermelde middelen in een hoeveel heid van 1 kg actieve verbinding/ha behandeld. De middelen werden voor dit doel gelijkmatig over de planten versproeid. Hier vertoonden de middelen volgens de uitvinding drie weken na de behandeling een grote selectiviteit naast een uitstekende wer- 800 0 1 12 - Π - king ten opzichte ran het onkruid. Het rergelijkingsmiddel vertoonde de selectiviteit niet.In a greenhouse, the plants listed in the following table were treated with the stated agents in the amount of 1 kg of active compound / ha after emergence. The agents were sprayed evenly over the plants for this purpose. Here, the agents of the invention three weeks after treatment showed great selectivity in addition to excellent action against weeds. The comparator did not show selectivity.
800 0 1 12 _ - 18 - ΒοχιτοοτιτυοΕ ο ο ο ο so ο οο Τ- Τ~ τ— Ο Ο Ο Ο κ\ (D *— Ο ΒθΐϋΟίχ ΟΟ Ο Ο τ- ια ια ο snqq.xx'Bj'BiiiY οο ο ο so csj kso q.sCjïï ?°°° ejfli “ 2 ° 2 tceoq.BX 2 1 ? ° ^ in ^ o uaq.ottpj'BY o o o o o ι i o800 0 1 12 _ - 18 - ΒοχιτοοτιτυοΕ ο ο ο ο so ο οο Τ- Τ ~ τ— Ο Ο Ο Ο κ \ (D * - Ο ΒθΐϋΟίχ ΟΟ Ο Ο τ- ια ια ο snqq.xx'Bj'BiiiY ο ο so csj kso q.sCjïï? ° ° ° ejfli “2 ° 2 tceoq.BX 2 1? ° ^ in ^ o uaq.ottpj'BY ooooo ι io
P ® PP ® P
p © I I Ό CDp © I I Ό CD
© +s *~v *~s iH +»© + s * ~ v * ~ s iH + »
+9 03 O O E CD+9 03 O O E CD
CO CD ES S CCS ΦCO CD ES S CCS Φ
© I iH τ-I A I P© I iH τ-I A I P
l x-v S B P ^~s © ^—V rP © © CÖ ιΗ Ί-5 r+ >4 H H O >» © >4 Ö >4 >4 I S3 ® ES Φ Ei S3 * - <D ιl x-v S B P ^ ~ s © ^ —V rP © © CÖ ιΗ Ί-5 r +> 4 H H O> »©> 4 Ö> 4> 4 I S3 ® ES Φ Ei S3 * - <D ι
© Cp O O l-t «H© Cp O O l-t «H
«H O rO A >3 o rH«H O rO A> 3 o rH
O S P P £3 S3 f>3 S3 -rt CÖ Cd CD -H c •HEo o Cw B © B © >4 >4 » (Ö chO S P P £ 3 S3 f> 3 S3 -rt CÖ Cd CD -H c • HEo o Cw B © B ©> 4> 4 »(Ö ch
cd Tl x 8 <—- H Ocd T1 x 8 <-HO
rH >s O O >4 >» S3 >4 S3 Λ Λ 8 S3 -ΗrH> s O O> 4> »S3> 4 S3 Λ Λ 8 S3 -Η
S3 O +9 +» O O SS3 O +9 + »O O S
O fO φ © rt fQ CÖO fO φ © rt fQ CÖ
Ρ P rH r+ >> F-C «—IR P rH r + >> F-C «—I
P © >4 >4 O'-SCÖ''-'^'-·' ©O Λ Λ E O t— © t~-P ©> 4> 4 O'-SCÖ '' - '^' - · '© O Λ Λ E O t— © t ~ -
O >4 -P -P CÖ IA >4 CTS O OSO> 4 -P -P CÖ IA> 4 CTS O OS
>,8® © ,0^80,00 8 O E B P · ° · P · ΟΛ » I Ö h 33 CO Ö ®>, 8® ©, 0 ^ 80.00 8 O E B P · ° · P · ΟΛ »I Ö h 33 CO Ö ®
t£ ,£3 -P T- ' r- O VO -P KS O KSt £, £ 3 -P T- 'r- O VO -P KS O KS
S3 +3 © v— w I tA Φ so >4 so •Η © S I · ^.|·8·S3 +3 © v— w I tA Φ so> 4 so • Η © S I · ^. | · 8 ·
-ÖllfA KS rP τ- KS CM O CM-ÖllfA KS rP τ- KS CM O CM
© ks ks ! I >4 W A© ks ks! I> 4 W A
•p--- "\| 'vj c -P | -P +9 -P• p --- "\ | 'vj c -P | -P +9 -P
>111 I © «p p Cp © Cp +* Ρ Ρ P P «p i-i © τ! I ·Ρ> 111 I © «p p Cp © Cp + * Ρ Ρ P P« p i-i © τ! I Ρ
•P © © © © <H p S3 P KS P• P © © © © <H p S3 P KS P
© © © © © >4 ,© N ,© -0-9 A© © © © ©> 4, © N, © -0-9 A
NNN N .© O rP O I ONNN N. © O rP O I O
© r-i r-i rP A *d -Ρ © ·Η CD p 03 •βτΙιΗτΙ Ή £3 ® Ή S3 Ή © ·Ρ S3 S3 S3 S3 τΙ Β Ο © Ο © Ο © © © © cd Ί3) ι ο ,ο ο to ο© ri ri rP A * d -Ρ © · Η CD p 03 • βτΙιΗτΙ Ή £ 3 ® Ή S3 Ή © · Ρ S3 S3 S3 S3 τΙ Β Ο © Ο © Ο © © © © cd Ί3) ι ο, ο ο to ο
S3 ,α +2 ,α +3 © - Ρ Ρ Ρ Η Ρ tJS3, α +2, α +3 © - Ρ Ρ Ρ Η Ρ tJ
φ p Ρ Ρ p Ή Ks -Ρ cd -Ρ -Η -Ρ *30 ÖC © © © © A —' ο Ο Ο £3ο ι-l Μ r-IOÖO Ο Ρ I Ο Ρ Ο © Ο Φ © Ο Ρ Ρ Ρ Ρ Φ- ο A Τ3 τ) >ooo Ο > fe m © m ρ © Ρ ,Μ © © © Ρ © Ρ CD —' -Ρ rP +3 © -Ρ Φ Ρ S3rHrPiH©rP®*3C I Ή Cp ·ρ Ο ·Ρ >Φ ©CpCpCp+sCH+ifiKS© I ©·Ρ©©3 £ t£| I I 03 I Ο τ( Μ fl fi Ο fi Η Η ÖKSKSKS®rd-®Jrfl I © ® Φ © ρ ι ι ι ι ι i-rrSmpoQi-icDO©® ^,ρρρΚηΚτ! ι © ο «Cp © © Α Φ © >4 >4 >4 |>4 ΐΗΓΡΦσΦ^ω ώΦΜ τΙΛΛΛγΗΛΗ Φ >» *50 γη *30 Ρ Ϊ50 Μ o+4-p-P >4+9 >J 6£ Λ Η Λ Η ΙιΡΦ Β pHHHaHöP-POUO^OP ΙΙλ ©I I I φ I Φ © © > I ί> «·>© ο l>SUlS<Hi?<H>Ss9K3-w-lAwOOr 80 0 0 1 12φ p Ρ Ρ p Ή Ks -Ρ cd -Ρ -Η -Ρ * 30 ÖC © © © © A - 'ο Ο Ο £ 3ο ι-l Μ r-IOÖO Ο Ρ I Ο Ρ Ο © Ο Φ © Ο Ρ Ρ Ρ Ρ Φ- ο A Τ3 τ)> ooo Ο> fe m © m ρ © Ρ, Μ © © © Ρ © Ρ CD - '-Ρ rP +3 © -Ρ Φ Ρ S3rHrPiH © rP® * 3C I Ή Cp · ρ Ο · Ρ> Φ © CpCpCp + sCH + ifiKS © I © Ρ © © 3 £ t £ | II 03 I Ο τ (Μ fl fi Ο fi Η Η ÖKSKSKS®rd-®Jrfl I © ® Φ © ρ ι ι ι ι ι i-rrSmpoQi-icDO © ® ^, ρρρΚηΚτ! Ι © ο «Cp © © Α Φ ©> 4> 4> 4 |> 4 ΐΗΓΡΦσΦ ^ ω ώΦΜ τΙΛΛΛγΗΛΗ Φ> »* 50 γη * 30 Ρ Ϊ50 Μ o + 4-pP> 4 + 9> J 6 £ Λ Η Λ Η ΙιΡΦ Β pHHHaHöP-POUO ^ OP ΙΙλ © III φ I Φ © ©> I ί> «·> © ο l> SUlS <Hi? <H> Ss9K3-w-lAwOOr 80 0 0 1 12
Claims (27)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792901658 DE2901658A1 (en) | 1979-01-15 | 1979-01-15 | DIURETHANE, METHOD FOR PRODUCING THESE COMPOUNDS AND HERBICIDES CONTAINING THEM |
| DE2901658 | 1979-01-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8000112A true NL8000112A (en) | 1980-07-17 |
Family
ID=6060757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8000112A NL8000112A (en) | 1979-01-15 | 1980-01-08 | DIURETHANES, METHOD FOR PREPARING THE SAME, AND HERBICIDES BASED ON THESE COMPOUNDS. |
Country Status (35)
| Country | Link |
|---|---|
| JP (1) | JPS5823865B2 (en) |
| AR (1) | AR224143A1 (en) |
| AT (1) | AT365411B (en) |
| AU (1) | AU532736B2 (en) |
| BE (1) | BE881152A (en) |
| BG (2) | BG31465A3 (en) |
| BR (1) | BR8000161A (en) |
| CA (1) | CA1128061A (en) |
| CH (1) | CH645343A5 (en) |
| CS (1) | CS212336B2 (en) |
| DD (1) | DD148709A5 (en) |
| DE (1) | DE2901658A1 (en) |
| DK (1) | DK16380A (en) |
| EG (1) | EG14116A (en) |
| ES (1) | ES487720A1 (en) |
| FI (1) | FI794081A7 (en) |
| FR (1) | FR2446275A1 (en) |
| GB (1) | GB2040939B (en) |
| GR (1) | GR71679B (en) |
| HU (1) | HU181682B (en) |
| IL (1) | IL59126A (en) |
| IN (1) | IN153545B (en) |
| IT (1) | IT1130864B (en) |
| MA (1) | MA18702A1 (en) |
| MX (1) | MX5743E (en) |
| NL (1) | NL8000112A (en) |
| PH (1) | PH15195A (en) |
| PL (1) | PL125248B1 (en) |
| PT (1) | PT70692A (en) |
| RO (1) | RO79454A (en) |
| SE (1) | SE8000278L (en) |
| SU (1) | SU942587A3 (en) |
| TR (1) | TR20529A (en) |
| YU (1) | YU1180A (en) |
| ZA (1) | ZA80244B (en) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1567151C3 (en) * | 1965-04-09 | 1974-02-21 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Diurethanes, processes for the preparation of these compounds and herbicidal compositions containing them |
| US3535101A (en) * | 1966-09-07 | 1970-10-20 | Schering Ag | Herbicide and algicide means |
| US3901936A (en) * | 1966-10-15 | 1975-08-26 | Schering Ag | Process for the preparation of n-carbamoyloxyphenyl carbamates |
| DE2413933A1 (en) * | 1974-03-20 | 1975-09-25 | Schering Ag | DIURETHANE WITH SELECTIVE HERBICIDAL EFFECT |
| JPS5140073A (en) * | 1974-06-28 | 1976-04-03 | Siemens Ag | |
| DE2557552C2 (en) * | 1975-12-18 | 1984-12-20 | Schering AG, 1000 Berlin und 4709 Bergkamen | Diurethanes and herbicidal agents containing these compounds as active ingredients |
| DE2638897C2 (en) | 1976-08-28 | 1978-10-26 | Basf Ag, 6700 Ludwigshafen | Diurethanes and herbicides containing them |
| DE2650796A1 (en) * | 1976-11-03 | 1978-05-11 | Schering Ag | DIURETHANE, METHOD FOR PRODUCING THESE COMPOUNDS AND THE SELECTIVE HERBICIDAL PRODUCT CONTAINING THEM |
-
1979
- 1979-01-15 DE DE19792901658 patent/DE2901658A1/en not_active Withdrawn
- 1979-12-24 IN IN940/DEL/79A patent/IN153545B/en unknown
- 1979-12-28 FI FI794081A patent/FI794081A7/en not_active Application Discontinuation
-
1980
- 1980-01-03 YU YU00011/80A patent/YU1180A/en unknown
- 1980-01-08 NL NL8000112A patent/NL8000112A/en not_active Application Discontinuation
- 1980-01-10 TR TR20529A patent/TR20529A/en unknown
- 1980-01-11 DD DD80218424A patent/DD148709A5/en unknown
- 1980-01-11 PH PH23505A patent/PH15195A/en unknown
- 1980-01-11 MX MX808584U patent/MX5743E/en unknown
- 1980-01-11 SU SU802867755A patent/SU942587A3/en active
- 1980-01-11 AT AT0013980A patent/AT365411B/en not_active IP Right Cessation
- 1980-01-12 EG EG21/80A patent/EG14116A/en active
- 1980-01-14 PL PL1980221361A patent/PL125248B1/en unknown
- 1980-01-14 BG BG046235A patent/BG31465A3/en unknown
- 1980-01-14 BG BG046234A patent/BG31495A3/en unknown
- 1980-01-14 CA CA343,600A patent/CA1128061A/en not_active Expired
- 1980-01-14 SE SE8000278A patent/SE8000278L/en not_active Application Discontinuation
- 1980-01-14 MA MA18899A patent/MA18702A1/en unknown
- 1980-01-14 PT PT70692A patent/PT70692A/en unknown
- 1980-01-14 IT IT19194/80A patent/IT1130864B/en active
- 1980-01-14 GR GR60957A patent/GR71679B/el unknown
- 1980-01-14 HU HU8063A patent/HU181682B/en unknown
- 1980-01-14 RO RO8099869A patent/RO79454A/en unknown
- 1980-01-14 IL IL59126A patent/IL59126A/en unknown
- 1980-01-15 AR AR279638A patent/AR224143A1/en active
- 1980-01-15 CH CH32280A patent/CH645343A5/en not_active IP Right Cessation
- 1980-01-15 ES ES487720A patent/ES487720A1/en not_active Expired
- 1980-01-15 ZA ZA00800244A patent/ZA80244B/en unknown
- 1980-01-15 DK DK16380A patent/DK16380A/en not_active Application Discontinuation
- 1980-01-15 GB GB8001303A patent/GB2040939B/en not_active Expired
- 1980-01-15 AU AU54604/80A patent/AU532736B2/en not_active Ceased
- 1980-01-15 CS CS80312A patent/CS212336B2/en unknown
- 1980-01-15 BE BE0/198971A patent/BE881152A/en not_active IP Right Cessation
- 1980-01-15 FR FR8000793A patent/FR2446275A1/en active Granted
- 1980-01-16 JP JP55002672A patent/JPS5823865B2/en not_active Expired
- 1980-09-10 BR BR8000161A patent/BR8000161A/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3639474A (en) | N-substituted perfluoroalkane-sulfonamides | |
| CA2770801A1 (en) | Pesticidal carboxamides | |
| BRPI0614911A2 (en) | 3-acylaminobenzanilides insecticides | |
| DE69108356T2 (en) | Hydrazone derivatives, process for their preparation and their use. | |
| US6657085B2 (en) | Process for the preparation of aniline compounds | |
| DE3143303A1 (en) | PYRIDAZINONE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES | |
| NL8000112A (en) | DIURETHANES, METHOD FOR PREPARING THE SAME, AND HERBICIDES BASED ON THESE COMPOUNDS. | |
| NO135471B (en) | ||
| US4080193A (en) | (Trifluoromet hylphenoxy)-phenylurea compounds and herbicidal compositions | |
| NL7906464A (en) | CARBANILIC ACID ESTERS, METHOD FOR PREPARING THE SAME, AND HERBICIDES BASED ON THESE COMPOUNDS. | |
| FR2495609A1 (en) | ACYLUREES, PROCESSES FOR THEIR PREPARATION AND INSECTICIDAL PRODUCTS CONTAINING SUCH COMPOUNDS | |
| GB1572542A (en) | Herbicidally active diurethanes process for their manufacture and their use | |
| DE69223132T2 (en) | BENZOYL URINE DERIVATIZED PYRAZOLES, COMPOSITIONS AND APPLICATIONS | |
| PL91404B1 (en) | ||
| US4163659A (en) | Stunting plant growth with N-substituted perfluoroalkanesulfonamides | |
| HU187447B (en) | Herbicides containing tetrahydro-pyrimidinone derivatives as active ingredients and process for the preparation of the active ingredients | |
| EP0406700A1 (en) | 3-Anilino-benzisothiazoles and fungicides containing them | |
| PL81425B1 (en) | ||
| EP0328999A1 (en) | N-sulfenylated 2-amino-4-chloro-thiazole sulfon amides, their use, process for their production, and the 2,4-dichloro-thiazole sulfochloride and 2-amino-4-chloro-thiazole sulfon amide derivatives | |
| WO1999037603A1 (en) | Organic nitrile derivatives and their use as pesticides | |
| US3717668A (en) | Substituted biscarbamates | |
| JP2001335559A (en) | Phthalic acid diamide derivatives, agricultural and horticultural insecticides and methods of using the same | |
| CS195342B2 (en) | Selective herbicide | |
| SU1148561A3 (en) | Method of obtaining derivatives of 1,2,3-thiadiazol-5-yl-urea | |
| CN102464618A (en) | Pyrazole amides and their applications |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |