CS212336B2 - Herbicide means and method of making the active substances of the same - Google Patents
Herbicide means and method of making the active substances of the same Download PDFInfo
- Publication number
- CS212336B2 CS212336B2 CS80312A CS31280A CS212336B2 CS 212336 B2 CS212336 B2 CS 212336B2 CS 80312 A CS80312 A CS 80312A CS 31280 A CS31280 A CS 31280A CS 212336 B2 CS212336 B2 CS 212336B2
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- Czechoslovakia
- Prior art keywords
- acid
- ester
- fluoro
- phenyl
- ethyl
- Prior art date
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- 230000002363 herbicidal effect Effects 0.000 title claims description 12
- 239000013543 active substance Substances 0.000 title 1
- 239000004009 herbicide Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 3-ethoxycarbonylaminophenyl Chemical group 0.000 claims description 149
- 150000002148 esters Chemical class 0.000 claims description 81
- 239000002253 acid Substances 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 10
- 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 8
- 230000000694 effects Effects 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 238000002360 preparation method Methods 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
- 238000000034 method Methods 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 240000008042 Zea mays Species 0.000 claims description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- XOOUNMBHFMARDR-UHFFFAOYSA-N (3,4-difluorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=C(F)C(F)=C1 XOOUNMBHFMARDR-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 240000007594 Oryza sativa Species 0.000 claims 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims 1
- 235000005822 corn Nutrition 0.000 claims 1
- 229910052731 fluorine Chemical group 0.000 claims 1
- 239000011737 fluorine Chemical group 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 238000002844 melting Methods 0.000 description 48
- 230000008018 melting Effects 0.000 description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 42
- 241000196324 Embryophyta Species 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- WZOMBBOIBCHWCP-UHFFFAOYSA-N (4-fluorophenyl)-methylcarbamic acid Chemical compound OC(=O)N(C)C1=CC=C(F)C=C1 WZOMBBOIBCHWCP-UHFFFAOYSA-N 0.000 description 10
- 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 description 9
- MGDDHBBPSNIXFW-UHFFFAOYSA-N (3-fluorophenyl)-methylcarbamic acid Chemical compound OC(=O)N(C)C1=CC=CC(F)=C1 MGDDHBBPSNIXFW-UHFFFAOYSA-N 0.000 description 8
- 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 7
- 235000002634 Solanum Nutrition 0.000 description 7
- 241000207763 Solanum Species 0.000 description 7
- 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 7
- 235000011331 Brassica Nutrition 0.000 description 6
- 241000219198 Brassica Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 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 description 5
- 230000035784 germination Effects 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 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
- BSAYWCZHCBTSCD-UHFFFAOYSA-N ethyl-(2-fluorophenyl)carbamic acid Chemical compound CCN(C(O)=O)C1=CC=CC=C1F BSAYWCZHCBTSCD-UHFFFAOYSA-N 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 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 description 3
- 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
- 229920000742 Cotton Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 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 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 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- IPQQXQKSRWITLK-UHFFFAOYSA-N (2-fluorophenyl)-methylcarbamic acid Chemical compound OC(=O)N(C)C1=CC=CC=C1F IPQQXQKSRWITLK-UHFFFAOYSA-N 0.000 description 1
- PCBXHSGXUDAMAR-UHFFFAOYSA-N (3,4-difluorophenyl)-ethylcarbamic acid Chemical compound CCN(C(O)=O)C1=CC=C(F)C(F)=C1 PCBXHSGXUDAMAR-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
- 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
- 235000016068 Berberis vulgaris 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
- 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
- 244000042664 Matricaria chamomilla Species 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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> 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
- 241000607479 Yersinia pestis Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- CQSOKXLEBDACLH-UHFFFAOYSA-N [3-(2-methylpropoxycarbonylamino)phenyl] N-(2-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound CC(COC(=O)NC=1C=C(C=CC1)OC(N(C1=C(C=CC=C1)F)CCC1=CC=CC=C1)=O)C CQSOKXLEBDACLH-UHFFFAOYSA-N 0.000 description 1
- MFKALTIEVGGMSB-UHFFFAOYSA-N [3-(but-3-en-2-yloxycarbonylamino)phenyl] N-(4-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound CC(C=C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)F)CCC1=CC=CC=C1)=O MFKALTIEVGGMSB-UHFFFAOYSA-N 0.000 description 1
- ZIHZVPIPUBVZCD-UHFFFAOYSA-N [3-(ethoxycarbonylamino)phenyl] N-(2-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound C(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=C(C=CC=C1)F)CCC1=CC=CC=C1)=O ZIHZVPIPUBVZCD-UHFFFAOYSA-N 0.000 description 1
- VLCYJUKOBQMFTC-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] N-(3,4-difluorophenyl)-N-ethylcarbamate Chemical compound COC(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=C(C=C1)F)F)CC)=O VLCYJUKOBQMFTC-UHFFFAOYSA-N 0.000 description 1
- JQPDTEKUVAUJIQ-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] N-(3-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound COC(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)CCC1=CC=CC=C1)=O JQPDTEKUVAUJIQ-UHFFFAOYSA-N 0.000 description 1
- PGOWLWQMOCDWQH-UHFFFAOYSA-N [3-(prop-2-ynoxycarbonylamino)phenyl] N-ethyl-N-(3-fluorophenyl)carbamate Chemical compound C(C#C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)CC)=O PGOWLWQMOCDWQH-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 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
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 150000004891 diazines Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- GABQKHQNXWNJJJ-UHFFFAOYSA-N diphenylcarbamic acid Chemical compound C=1C=CC=CC=1N(C(=O)O)C1=CC=CC=C1 GABQKHQNXWNJJJ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003673 groundwater Substances 0.000 description 1
- 150000003977 halocarboxylic acids Chemical class 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 150000007529 inorganic bases Chemical class 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
- 235000009973 maize 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
- 235000010446 mineral oil Nutrition 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
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 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
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 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
212336 2212336 2
Vynález se týká herbicidního prostředku a způsobu výroby jeho účinné látky. Konkrétnáse zde pojednává o nových dluretanech, způsobu výroby táchto sloučenin, jakož 1 herbicidnichprostředcích, obsahujících alespoň jednu z táchto sloučenin.The present invention relates to a herbicidal composition and to a process for the preparation of an active ingredient thereof. Specifically, new dlurethanes, a process for making such compounds, and 1 herbicidal compositions containing at least one of these compounds are discussed herein.
Herbicidní účinek diuretanů je jiř znán. Známé účinné látky tohoto druhu mají selek-tivní herbicidní účinek zejména vůči řepá nebo vůči bobůn sóji. Úlohou vynálezu je vyvinutí herbicidnlho prostředku, která má velmi dobrou účinnostvůči těžce potíratelnému plevelu a současná vykazuje dobrou snášenlivost zejména u bavlní-kových kultur.The herbicidal effect of diurethanes is already known. The known active compounds of this kind have a selective herbicidal action, in particular against beet or soybean. SUMMARY OF THE INVENTION It is an object of the present invention to provide a herbicidal composition which has a very good potency in hard-to-control weeds and currently exhibits good tolerance, especially in cotton crops.
Tato úloha je podle vynálezu vyřešena herbicidním prostředkem, který se vyznačujetím, že jako účinnou látku obsahuje alespoň jednu sloučeninu obecného vzorce kde B, znamená methylový, ethylový, propylový, lsopropylový, butylový, isobutylový, sek.butylový nebo 2-fenylethylový zbytek aThis object is achieved according to the invention by a herbicidal composition comprising at least one compound of the general formula wherein B is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or 2-phenylethyl and
Hg ' znamená methylový, ethylový, propylový, isopropylový, butylový, isobutylový, sek. butylový, allylový, propargylový, ehlorethylový, 1-chlormethylethylový, 4-chlorbuti-nylový, 1-methylpropinylový nebo 4-chlorbutenylový zbytek, Y znamená vodík nebo fluor a X znamená kyslík nebo síru.Hg 'is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, allyl, propargyl, chloroethyl, 1-chloromethylethyl, 4-chlorobutinyl, 1-methylpropinyl or 4-chlorobutenyl, Y is hydrogen or fluoro, and X is oxygen or sulfur.
Sloučeniny podle vynálezu' jsou s překvapením znamenitá snášeny bavlníkovými kulturami,což nelze tvrdit o známých sloučeninách analogické konstituce.The compounds of the invention are surprisingly well tolerated by cotton cultures, which cannot be claimed of known compounds analogous to constitution.
Kromě toho vykazují velmi dobrý účinek na plevele, které lze jen velmi obtížnápotírat, jako je amaranthus, stellaria, matricaria a jiné, které lze potírat jak předvyklíčením tak i po vyklíčení. K potírání těchto semenných plevelů postačují zpravidla používaná množství 1 až 5 kgúčinné látky/ha, přičemž sloučeniny podle vynálezu působí selektivně kromě u bavlníku i ujiných kultur užitkových rostlin, jako u sóji, podzemnice olejně, brambor, kukuřice, rý-že, ciroku a obilí.In addition, they have a very good effect on weeds, which are very difficult to coat, such as amaranthus, stellaria, matricaria and others, which can be combated by both pre-germination and germination. Usually, amounts of 1 to 5 kg of active ingredient / ha are sufficient to control these seed weeds, with the compounds of the invention acting selectively except for cotton crops and other crop plants such as soybean, groundnut, potato, maize, rye, sorghum and grain. .
Sloučeniny podle vynálezu se mohou používat buá samotné nebo ve vzájemné směsi nebove směsi s jinými účinnými látkami. Popřípadě lze přidávat jiné prostředky rostlinnéochrany nebo prostředky pro potírání škůdců, a to vždy podle požadovaného účelu.The compounds of the invention may be used either alone or in admixture with each other or with other active ingredients. Other plant protection or pest control agents may optionally be added, depending on the desired purpose.
Pokud se sleduje rozšíření spektra účinku lze přidávat i jiné herbicidní prostředky.Například jako herbicidná účinní partneři se hodí účinné látky vybrané ze skupin triazinů,aminotriazolů, anilidů, diazinů, uracilů, alifatických karboxylových kyselin a halogen-karboxalových kyselin, substituovaných benzoových kyselin a aryloxykarboxylových kyselin,hydrazidů, amidů, nitrilů, esterů takovýchto karboxylových kyselin, esterů kyseliny kar-bamidové a thiokarbamidové, močoviny, 2,3,6-trichlorbenzyloxyisopropanolu a prostředků,obsahujících rhodan aj. Pod pojmem jiné přísady lze rozumět i nefytotoxické přísady,které u herbicidnich prostředků vyvolávají synergické zvýáení účinku, jako smáčedla, emul-gátory, rospouětědla o olejovité přísady. 3 212336 S výhodou a· definovaná účinná látky nebo jejich směsi používají ve.formě přípravků,jako prásků, zásypů, granulátů, roztoků, emulzí nebo suspenzí, za přídavku kapalných a/ne-bo pevných nosičů popřípadě zřeúovadel a popřípadě smáčedel, adhezních prostředků, emulgá-torů a/nebo dispergačních pomocných prostředků.Other herbicidal compositions may be added as long as the spectrum of action is observed. For example, active compounds selected from the group of triazines, aminotriazoles, anilides, diazines, uracils, aliphatic carboxylic acids and halocarboxylic acids, substituted benzoic acids and aryloxycarboxylic acids are suitable as herbicidal partners. , hydrazides, amides, nitriles, esters of such carboxylic acids, esters of carbamic acid and thiocarbamide, urea, 2,3,6-trichlorobenzyloxyisopropanol and compositions comprising rhodane etc. Other additives may also include non-phytotoxic additives which, in herbicidal compositions they produce a synergistic increase in action such as wetting agents, emulsifiers, oily additives. Preferably, the active ingredients or mixtures thereof defined in the form of preparations, such as powders, powders, granules, solutions, emulsions or suspensions, are added with the addition of liquid and / or solid carriers or diluents and optionally wetting agents, adhesives, emulsifiers and / or dispersing aids.
Vhodná kapalná nosiče jsou například voda, alifatická a aromatické uhlovodíky, jakobenzen, toluen, xylen, cyklohexanon, isoforon, dimethylsulfoxid, dimethylformamid, a dálefrakce minerálních olejů.Suitable liquid carriers are, for example, water, aliphatic and aromatic hydrocarbons, as benzene, toluene, xylene, cyclohexanone, isophorone, dimethylsulfoxide, dimethylformamide, and the mineral oil fraction.
Jako pevná nosiče se hodí minerální zeminy, například tonsil, silikagel, talek, kaolin,attaclay, vápenec, kyselina křemičitá, a rostlinné produkty, například mouky. Z povrchově aktivních látek lze jmenovat například ligninsulfonan vápenatý, polyoxy-etylenalkylfenoléter, naftalensulfonové ky’seliny a jejich soli, fenolsulfonové kyselinya jejich soli, kondenzáty formaldehydu, sírany vyěěích alifatických alkoholů, jakož isubstituovaná benzenaulfonová kyseliny a jejich soli.Suitable solid carriers are mineral soils, for example tonsil, silica gel, talc, kaolin, attaclay, limestone, silicic acid, and vegetable products such as flour. Surfactants include, for example, calcium lignin sulfonate, polyoxyethylene alkylphenol ether, naphthalenesulfonic acids and their salts, phenolsulfonic acids, and their salts, condensates of formaldehyde, sulfates of aliphatic alcohols as well as substituted benzenesulfonic acids and their salts.
Podíl účinná látky, popřípadě účinných látek, v různých přípravcích se může měnitv ěirokých mezích. Prostředky obsahují například asi 5 až 95% hmot. účinná látky, asi95 až 5 % hmot. kapalného nebo pevného nosiče, jakož i popřípadě až 20 hmot. % povrchověaktivních látek.The proportion of active ingredient (s) in the various formulations may vary within wide limits. The compositions contain, for example, about 5 to 95 wt. % active ingredient, about 95 to 5 wt. a liquid or solid support, and optionally up to 20 wt. % surfactants.
Nanášení prostředků se může provádět různým způsobem, například s vodou jako nosičemv postřiková břečce v množství asi 50 až 1' 000 litrů/ha. Použití prostředků při tak zva-ném maloobjemovém a ultramaloobjemovém způsobu je právě tak možná jako jejich aplikaceve formě tak zvaných mikrogranulí.The application of the compositions can be carried out in various ways, for example with water as a carrier for spray liquor in an amount of about 50 to 1000 liters / ha. The use of the compositions in such a small-volume and ultra-low volume manner is just as possible as their application as so-called microgranules.
Za sloučenin podle vynálezu se vynikajícím selektivním účinkem vyznačují zejména(3-ethoxykerbonylaminofenyl)ester N-ethyl-3-fluorkarbanilové kyseliny, /3-(1-methylethoxy-karbonylamino)fenyl/ester N-ethyl-3-fluorkarbanilové kyseliny. (3-ethoxykarbonylaminofenyl)-ester N-ethyl-4-fluorkarbanilové kyseliny, (3-ethoxykarbonýlaminofenyl)ester 4-fluor-N--mathylkarbanilové kyseliny, /3-t1-methylethoxykarbonylamino)fenyl/ester N-ethyl-3-fluor-karbanilové kyseliny, /3-(,-methylethoxykarbonylamino)fenyl/ester N-ethyl-4-fluorkarbanilo-vé kyseliny, /3-(1-methylethoxykarbonylamino)fenyl/ester 4-fluor-N-methylkarbanilovékyseliny, /3-(T-methylethoxykarbonylsmino)fenyl/ester 3-fluor-N-methylkarbenilové kyseli-ny, (3-athoxykarbonylaminofenyl)ester N-ethyl-3,4-difluorkarbanilové kyseliny a (3-methoxy-karbonylaminofenyl)ester N-athyl-2-fluorkarbanilové kyseliny. Účinné látky používané v herbicidním prostředku podle vynálezu se dají vyrobit napří-klad tím, že se sloučenina obecného vzorce O-co-ClIn particular, N-ethyl-3-fluorocarbanilic acid, (3- (1-methylethoxycarbonylamino) phenyl) N-ethyl-3-fluorocarbanilic acid ester, exemplify the compounds of the invention with excellent selective action. (3-ethoxycarbonylaminophenyl) ester of 4-fluoro-N-methylcarbanilic acid, (3-ethoxycarbonylaminophenyl) ester of N-ethyl-4-fluorocarbanilic acid, N-ethyl-3-fluoro- (3-t-methylethoxycarbonylamino) phenyl carbanilic acid, [3- (1-methylethoxycarbonylamino) phenyl] ester of N-ethyl-4-fluorocarbonic acid, [3- (1-methylethoxycarbonylamino) phenyl] ester of 4-fluoro-N-methylcarbanilic acid; N-ethyl-3,4-difluorocarbanilic acid (3-methoxycarbonylaminophenyl) ester of N-methyl-2-fluorocarbanilic acid and methyl 3-fluoro-N-methylcarbenilic acid ester; The active compounds used in the herbicidal composition according to the invention can be prepared, for example, by the fact that the compound of the formula O-co-Cl
^J~NH-COXR2 kdeX a R2 mají shora uvedený význam, nechá reagovat v přítomnosti akceptoru kyseliny s aminem obecného vzorceWherein X and R2 are as defined above, reacted in the presence of an acid acceptor with an amine of the formula
HNHN
212336 4212336 4
Jako akceptor kyseliny se například může použít přídavek přebytečného množství aminunebo anorganické .zásady, jako například hydroxidu sodného, uhličitanu sodného, uhličitanudraselného nebo terciární organické báze, jako například triethylaminu, Následující příklady vysvětlují výrobu sloučenin podle vynálezu. Přikladl /3-(ethylthiokarbonylamino)fenylester N-ethyl-3-fluorkarbonilové kyselinyFor example, the addition of an excess amount of an amino or inorganic base such as sodium hydroxide, sodium carbonate, carbonate potassium or a tertiary organic base such as triethylamine may be used as the acid acceptor. The following examples explain the preparation of the compounds of the invention. Example 1 N-ethyl-3-fluorocarbonylic acid 3- (ethylthiocarbonylamino) phenyl ester
Do roztoku 13,9 g (0,1 molu) N-ethyl-3-fluoranilinu v 70 ml ethylesteru kyselinyoctové se přikape za míchání a ochlazení na 10 až 15 °C roztok 26,0 g (0,1 molu) /3--(ethylthiokarbonylamino)fenyl/esteru kyseliny chlormnavenčí v 70 ml ethylesteru ky-seliny octové a současné roztok 13,8 g (0,1 molu) uhličitanu draselného v 50 ml vody. Míchá se dále 30 minut při 15 °C, potom se oddélí organická fáze a za přidání ledu sepromývá zředěnou kyselinou chlorovodíkovou a vodou. Po usušeni síranem hořečnatýmse za sníženého tlaku odpaří. Odparek se překrystaluje ze směsi ethylesteru kyselinyoctové a pentanu. Výtěžek: 29,4 g 8, % teorie [3-(etylthiokarbonylamino)-fenyl]-esteru N-ethyl 3-fluorkar-benilové kyseliny.To a solution of 13.9 g (0.1 mol) of N-ethyl-3-fluoroaniline in 70 ml of ethyl acetate is added dropwise, under stirring and cooling, a solution of 26.0 g (0.1 mol) / 3 to 15 ° C. chloroformate ester in 70 ml of ethyl acetate and simultaneously a solution of 13.8 g (0.1 mol) of potassium carbonate in 50 ml of water. Stirring is continued for 30 minutes at 15 ° C, then the organic phase is separated off and washed with dilute hydrochloric acid and water with the addition of ice. After drying over magnesium sulfate, it is evaporated under reduced pressure. The residue was recrystallized from ethyl acetate / pentane. Yield: 29.4 g of 8% of theory of N-ethyl 3-fluorocarbenilic acid [3- (ethylthiocarbonylamino) phenyl] ester.
Teplota tání: 127 °CMelting point: 127 ° C
Analogickým způsobem lze vyrobit následující sloučeniny podle vynálezu: Název sloučeniny fyzikální konstanty (3-methoxykarbonylaminofenyl)-ester 3- fluor-N-methylkarbanilové kyseliny(3-methoxykarbonylaminofenyl)-esterN-etyl-3-fluorkarbanilové kyseliny [3-(methylthiokarbonylamino)-fenyl]-esterN-etyl-3-fluorkarbanilové kyseliny(3-methoxykarbonylaminofenyl)-ester 4- fluor-N-methylkarbanilové kyseliny [3-(methylthiokarbonylamino)fenyl] -ester4-£luor-N-metylkarbanilové kyseliny[3-(methylthiokarbonylamino)-fenylJ esterN-ethyl-4-fluorkarbanilové. kyseliny(3-methoxykarbonylaminofenyl)-esterN-ethyl-4-fluorkarbanilová kyseliny(3-ethoxykarbonyleminofenyl)-esterN-ethyl-4-fluorkarbanilové kyseliny, (3-ethoxykarbonylaminofenyl)-esterN-ethyl-3-fluorkarbanilové kyseliny(3-ethoxykarbonylaminofenyl)-ester 3- fluor-N-methylkarbanilové kyseliny[3-(methylthiokarbonylamino)-fenyl]-ester 3-fluor-N-methylkarbanllové kyseliny[3- (ethyl thiokarbonylamino)-f enyl] -ester 3-fluor-N-methylkarbanllové kyseliny(3-etoxykarbonylaminofenyl)-ester 4- fluor-N-methylkarbanilové kyseliny teplota tání: teplota tání: teplota tání: teplota tání: teplota tání: teplota tání: teplota tání: teplota tání: teplota tání: teplota tání: teplota tání: teplota tání:n£°: 1,5472The following compounds of the invention can be prepared in an analogous manner: Name of the compound physical constant (3-methoxycarbonylaminophenyl) ester of 3-fluoro-N-methylcarbanilic acid (3-methoxycarbonylaminophenyl) esterN-ethyl-3-fluorocarbanilic acid [3- (methylthiocarbonylamino) phenyl] [3- (methylthiocarbonylamino) -] - [3- (methylthiocarbonylamino) phenyl] ester-4-fluoro-N-methylcarbanilic acid [3- (methylthiocarbonylamino)] - N-ethyl-3-fluorocarbanilic acid ester (3-methoxycarbonylaminophenyl) ester phenylJ ester of N-ethyl-4-fluorocarbanil. (3-methoxycarbonylaminophenyl) esterN-ethyl-4-fluorocarbanilic acid (3-ethoxycarbonyleminophenyl) esterN-ethyl-4-fluorocarbanilic acid, (3-ethoxycarbonylaminophenyl) esterN-ethyl-3-fluorocarbanilic acid (3-ethoxycarbonylaminophenyl) - 3-Fluoro-N-methylcarbanilic acid ester [3- (methylthiocarbonylamino) phenyl] 3-fluoro-N-methylcarbanic acid ester [3- (ethyl thiocarbonylamino) phenyl] ester 3-fluoro-N-methylcarbanic acid ( 4-fluoro-N-methylcarbanilic acid 3-ethoxycarbonylaminophenyl) melting point: m.p .: melting point: melting point: m.p. n ° °: 1.5472
105 až 107 °C 108 až 109 °C 125 až 127 °C 96 i až ! 97 °C 106 až 108 °C 143 až 144 °C 117 až 118 °C 76 . až 77 °C 122 °C 91 i až : 92 °C 116 °c 124 až 125 °C 5 212336 Název sloučeniny (3-methoxykarbonylaminofenyl)-ester 4-fluor-N-(2-fenylethyl)-karbanilové kyseliny(3-ethoxykarbonylaminofenyl)-ester4-fluor-Nt- (2-fenyletbyl) -karbanilové kyseliny[3-(1-methylethoxykarbonylamino)-fenylj-esterN-ethyl-3-fltorkarbanilové kyseliny[3-(1-methylethoxykarbonylamino)-fenylj-esterN-etyl-4-fluorkarbanilové kyselinyÍ3—(1-methylethoxykarbonylamino)-fenylJ -ester4-fluor-N-methylkarbanilové kyseliny[3-(ethylthiokarbonylamino)-fenylj-esterN-ethyl-4-fluorkarbanilové kyseliny[3-(ethylthiokarbonylamino)-fenyl]-ester4-fluor-N-methylkarbanilové kyseliny[3-(2-propionyloxykarbonylamino)-fenylj-ester 3- fluor-N-methylkarbanilové kyseliny [3-(2-propinyloxykarbonylamino)-fenylj-ester N-ethyl-3-fluorkarbanilové kyseliny f.3-( ethylthiokarbonylamino )f enylj-ester 4- fluor-N-(2-fenylethyl)-karbanilové kyseliny[3-(1-methylethoxykarbonylamino)-fenyl]-ester4-fluor-N-(2-fenylethyl)-karbanilové kyseliny(3-allyloxykarbonylaminofenyl)-es terN-ethyl-4-fluorkarbanilové kyseliny (3-propinyloxykarbonylaminofenyl)-ester N-ethyl-4-fluorkarbanilové kyseliny (3-allyloxykarbonylaminofenyl)-ester 4-fluor-N-2-fenylethyl-karbanilové kyseliny(3-methoxykarbonylaminofenyl)-ester 3-fluor-N-(2-fenylethyl)-karbanilové kyseliny(3-methoxykarbonylaminofenyl)-esterN-ethyl-2-fluorkarbanilové kyseliny(3-aie thoxykarbonylaminof enyl)-es terN-ethyl-3,4-difluorkarbanilové kyseliny(3-ethoxykarbonylaminofenyl)-ester 3-fluor-N-(2-fenylethyl)-karbanilové kyseliny[3-(ethylthiokarbonylamino)-fenyl]-ester 3-fluor-N-(2-fenylethyl)-karbanilové kyseliny[3-d -methylethoxykarbonylamino)-fenylj-ester 3-fluor-N-methylkarbanilové kyseliny(3-allyloxykarbonylaminofenyl)-ester 3-fluor-N-methylkarbanilové kyseliny(3-allyloxykarbonylaminofenyl)-es ter 3- fluor-N-ethylkarbanilové kyseliny (3-allyloxykarbonylaminofenyl)-ester 4- fluor-N-methylkarbanilové kyseliny [3-(1-ohlormethyletoxykarbonylamino)-fenyl]-esterN-ethyl-3-fluorkarbanilové kyseliny(3-e thoxykarbonylaminofenyl)-e sterN-ethyl-3,4-difluorkarbanilové kyseliny[3-(methylthiokarbonylamino)-fenyl] -esterN-ethyl-3,4-difluorkarbanilové kyseliny fyzikální konstanty105 to 107 ° C 108 to 109 ° C 125 to 127 ° C 96 to! 97 ° C 106 to 108 ° C 143 to 144 ° C 117 to 118 ° C 76. to 77 ° C 122 ° C 91 to: 92 ° C 116 ° C 124 to 125 ° C 5 212336 4-Fluoro-N- (2-phenylethyl) -carbanilic acid 3-methoxycarbonylaminophenyl ester (3- [3- (1-Methyl-ethoxycarbonylamino) -phenyl] -ethyl-3-fluoro-carbanilic acid [3- (1-methyl-ethoxycarbonylamino) -phenyl] -ethyl-N-ethyl-ethoxycarbonylamino-phenyl] -4-fluoro-Nt- (2-phenylethyl) -phenyl] ester ester [3- (ethylthiocarbonylamino) phenyl] -N-ethyl-4-fluorocarbanilic acid [3- (ethylthiocarbonylamino) phenyl] ester4- (1-methylethoxycarbonylamino) phenyl-4-fluoro-N-methylcarbanilic acid [3- (ethylthiocarbonylamino) phenyl] -4- 3-Fluoro-N-methylcarbanilic acid [3- (2-propionyloxycarbonylamino) -phenyl] -phenyl] -fluoro-N-methylcarbanilic acid N-ethyl-3-fluorocarbanilic acid 3- (2-propynyloxycarbonylamino) -phenyl ester f.3 4-Fluoro-N- (2-phenylethyl) -carbanilic acid (ethyl-thiocarbonylamino) -phenyl-ester [3- (1-methylethoxycarbonylamino) -phenyl] -ester-4-fluoro-N- (2-phenylethyl) -carbanilic acid (3-allyloxycarbonylaminophenyl) esters of N-ethyl-4-fluorocarbanilic acid (3-propyloxycarbonylaminophenyl) ester of 4-fluoro-N-2-phenylethylcarbanilic acid (3-allyloxycarbonylaminophenyl) ester (3-methoxycarbonylaminophenyl) ester of 3-fluoro-N- (2-phenylethyl) carbanilic acid (3-methoxycarbonylaminophenyl) ester of N-ethyl-2-fluorocarbanilic acid (3-thiocarbonylaminophenyl) estersN-ethyl-3, 3-Fluoro-N- (2-phenylethyl) -carbanilic acid 3-fluoro-N- (2-phenylethyl) -carbanilic acid 3-fluoro-N- (2-phenylethyl) -carbanilic acid 4-difluorocarbanilic acid ester 3-fluoro-N-methylcarbanilic acid (3-allyloxycarbonylaminophenyl) ester 3-fluoro-N-methylcarbanilic acid (3-allyloxycarbonylaminophenyl) esters 3-fluoro-N-ethylcarbanilic acid [3-d-methylethoxycarbonylamino] phenyl ester 4-Fluoro-N-methylcarbanilic acid (3-allyloxycarbonylaminophenyl) ester [3- (1-chloromethyl-ethoxycarbonylamino) -phenyl] -esterN-ethyl -3-fluorocarbanilic acid (3-ethoxycarbonylaminophenyl) - sterN-ethyl-3,4-difluorocarbanilic acid [3- (methylthiocarbonylamino) phenyl] esterN-ethyl-3,4-difluorocarbanilic acid physical constants
teplota tání: 137 °Cteplota tání: 103 až 104 °Cteplota tání: 98 °Cteplota tání: 84 až 86 °Cteplota tání: 88 °Cteplota tání: 79 °Cteplota tání: 97 až 99 °Cteplota táni: ,42 až ,44 °Cteplota tání: 148 až ,50 °Cteplota tání 117 °Cteplota tání: 81 až 83 °Cteplota tání: 73 až 74 °Cteplota tání: 79 až 80 °Cteplota tání: 8, °Cteplota tání: 1,2 až 113 °Cmp: 137 ° Melting point: 103-104 ° Melting point: 98 ° Melting point: 84-86 ° Melting point: 88 ° Melting point: 79 ° Melting point: 97-99 ° Melting point: 42-44 ° Melting point: 148 to 50 ° Melting point: 117 ° Melting point: 81 to 83 ° Melting point: 73 to 74 ° Melting point: 79 to 80 ° Melting point: 8 ° C Melting point: 1.2 to 113 ° C
teplota tání: ,06 až 107 °C teplota tání: ,21 až 122 °Cteplota tání: 115 °Cteplota tání: 91 až 93 °Cteplota tání: 74 až 76 °Cteplota tání: 78 až 80 °Cteplota tání: 101 až 103 °Cn^° : 1,5536Melting point: 06 to 107 ° C Melting point: 21 to 122 ° Melting point: 115 ° Melting point: 91 to 93 ° Melting point: 74 to 76 ° Melting point: 78 to 80 ° Melting point: 101 to 103 ° C11 H15: 1.5536
teplota tání: 68 až 70 °Cteplota tání: 69 áž 70 °Cteplota tání: 130 až 132 °C 6 212336. Název sloučeniny fyzikální konstanty (3-methoxykarbonylaminofenyl)-ester 2-fluor-N-(2-fenylethyl)-karbanilové kyseliny(3-ethoxykarbonylaminofenyl)-ester2-fluor-N-(2-fenylethyl)-karbanilové kyseliny[3-(me thylthlokarbonylamino)-fenyl]-ester2-fluor-N-(2-fenylethyl)-karbanilové kyseliny[3-(ethylthlokarbonylamino)-fenyl]-ester2-fluor-N-(2-fenylethyl)-karbanilové kyseliny[3- (1 -me thyle thoxykarbony1amino)-f enyl]-e s ter 2- fluor-N-(2-fenylethyl)-karbanilové kyseliny(3-methoxykarbonylamino)-fenylester 3- fluor-N-propylkarbanilové kyseliny [3-methylthlokarbonylamino)-fenyl]-ester 3-fluor-N-propylkarbanilové kyseliny (3-ethoxykarbonylamino)-fenylester 3-fluor-N-propylkarbanilové kyseliny [3-(1-methyl-2-propenyloxykarbonylamino)-fenyl]-esterN-ethyl-3-fluorkarbanilové kyseliny [3-( 1-methy).-2-propenyloxykarbonylamino)-f enyl] -esterN-ethyl-2-fluorkarbanllové kyseliny[3-(1-methyl-2-propenyloxykarbonylamino)-fenyl] -esterN-ethyl-4-fluorkarbanilové kyseliny(3-methoxykarbonylamino)-fenylesterN-butyl-3-fluorkarbánilové kyseliny[3-(2-methylpropoxykarbonylamino)-fenyl] -ester 3- fluor-N-methylkarbanilové kyseliny [3-( 1-methyl-2-propenyloxykarbonylamino, -fenyl] -ester 4— fluor-N-(2-fenylethyl)-karbanilové kyseliny [3-(1methyl-2-propenyloxykarbonylamino)-fenyl] -ester 3-fluor-N-(2-fenylethyl)-karbanilové kyseliny [3-(1-methyl-2-propenyloxykarbonylamino)-fenyl]-ester 3- fluor-N-methylkarbanilové kyseliny [3-(1-methyl-2-propenyloxykarbonylamino)-fenyl]-ester 4- fluor-N-methylkarbanilové kyseliny [3—(1-methyl-2-propenyloxykarbonylamino)-fenyl] -ester N-butyl-4-fluorkarbanilové kyseliny [3-(2-methylpropoxykarbonylamino)-fenyl]-ester 4-fluor-N-methylkarbanilové kyseliny[3-(1-methyl-2-propenyloxykarbonylamino)-fenyl]-ester 4-fluor-N-propylkarbanilové kyseliny(3-ethoxykarbonylaminofenyl)-esterN-ethyl-2-fluorkarbanilové kyseliny[3-(methylthiokarbonylamino)-fenyl]-esterN-ethyl-2-fluorkarbanilové kyseliny[3-(ethylthiokarbonylamino)-fenyl]-esterN-ethyl-2-fluorkarbanilové kyseliny(.3-( 1-methylethoxykarbonylamino)-fenyl]-esterN-ethyl-2-fluorkarbanilové kyseliny[3-(2-propinyloxykarobnylamino)-fenylj-esterN-ethyl-2-fluorkarbanilové kyseliny (3-allyloxykarbonylaminofenyl)-ester 2-fluor-N-2-fenylethyl-karbanilové kyseliny teplota tání teplota tání teplota tání teplota tání teplota tání teplota tání teplota tání teplota tání teplota tání teplota tání teplota tání teplota tání teplota táníMelting point: 68 to 70 ° Melting point: 69 to 70 ° Melting point: 130 to 132 ° C 6 212336. Physical constant (3-methoxycarbonylaminophenyl) ester 2-fluoro-N- (2-phenylethyl) -carbanilic acid (3-ethoxycarbonylaminophenyl) ester of 2-fluoro-N- (2-phenylethyl) carbanilic acid [3- (methylthlokarbonylamino) phenyl] ester 2-fluoro-N- (2-phenylethyl) carbanilic acid [3- (ethylthlokarbonylamino) 2-Fluoro-N- (2-phenylethyl) -carbanilic acid [3- (1-thiomethoxycarbonyl-amino) -phenyl] -ester-2-fluoro-N- (2-phenylethyl) -carbanilic acid 3-Fluoro-N-propylcarbanilic acid (3-methoxycarbonylamino) -phenyl ester 3-fluoro-N-propylcarbanilic acid 3-fluoro-N-propylcarbanilic acid 3-fluoro-N-propylcarbanilic acid [3 - (1-methyl-2-propenyloxycarbonylamino) -phenyl] -ester-N-ethyl-3-fluorocarbanilic acid [3- (1-methyl-2-propenyloxycarbonylamino) -phenyl] -esterN-ethyl-2-fluorocarbonic acid [ 3- (1-methyl -2-propenyloxycarbonylamino) phenyl] ester N-ethyl-4-fluorocarbanilic acid (3-methoxycarbonylamino) -phenyl ester N-butyl-3-fluorocarbanilic acid [3- (2-methylpropoxycarbonylamino) phenyl] ester 3-fluoro-N- methylcarbanilic acid [3- (1-methyl-2-propenyloxycarbonylamino, -phenyl] -ester of 4-fluoro-N- (2-phenylethyl) carbanilic acid [3- (1-methyl-2-propenyloxycarbonylamino) phenyl] ester 3- 3-Fluoro-N-methylcarbanilic acid [3- (1-methyl-2-propenyloxycarbonylamino) -fluoro-N- (2-phenylethyl) -carbanilic acid [3- (1-methyl-2-propenyloxycarbonylamino) -phenyl] -ester 4-Fluoro-N-methylcarbanilic acid phenyl] ester N-butyl-4-fluorocarbanilic acid [3- (2-methylpropoxycarbonylamino) phenyl] ester [3- (1-methyl-2-propenyloxycarbonylamino) phenyl] ester 4-fluoro-N-methylcarbanilic acid [3- (1-methyl-2-propenyloxycarbonylamino) phenyl] ester 4-fluoro-N-propylcarbanilic acid (3-ethoxycarbonylaminophenyl) ester N-ethyl-2-fluorocarbanilic acid [3- (methylthiocarbonylamino) -f enyl] -esterN-ethyl-2-fluorocarbanilic acid [3- (ethylthiocarbonylamino) phenyl] ester N-ethyl-2-fluorocarbanilic acid (3- (1-methylethoxycarbonylamino) phenyl) ester N-ethyl-2-fluorocarbanilic acid [3- (2-propynyloxycarobnylamino) phenyl] ester-N-ethyl-2-fluorocarbanilic acid (3-allyloxycarbonylaminophenyl) ester of 2-fluoro-N-2-phenylethyl carbanilic acid, melting point melting point melting point melting point melting point melting point melting point melting point melting point melting point melting point
125 až 126 °CMp 125-126 ° C
128 až ,30 °C148 až 149 °C128 to 30 ° C, 148 to 149 ° C
124 °C124 ° C
109 až 110 °C109-110 ° C
90 až 92 °C90-92 ° C
103 až 105 °C103 až 105 °C103-105 ° C 103-105 ° C
100 až 101 °C100-101 ° C
109 až 110 °C73 až 74 °C79 až 80 °C109-110 ° C73-74 ° C79-80 ° C
94 až 95 °C „20.nD . 1,5578 „20.nD . 1,5632 „20.nD · 1,5509 „20.nD · 1,5465 „20 nD : 1,5298 „20 nn : 1,5313 teplota tání teplota tání teplota tání teplota tání teplota tání teplota tání teplota tání94-95 ° C. 1.5578 "20.nD. 1.5632 "20.nD · 1.5509" 20.nD · 1.5465 "20 nD: 1.5298" 20 nn: 1.5313 melting point melting point melting point melting point melting point melting point
75 až 76 °C151 až 153 °C160 až 162 °C75 to 76 ° C, 151 to 153 ° C, 160 to 162 ° C
146 až 147 °C126 až 127 °C146-147 ° C126-127 ° C
: 150 °C: 150 ° C
: 72 až 73 °C 7 212336 Název sloučeniny · fyzikální- konstanty [3-(2-methylpropoxykarbonylamino )-fenyl] -ester 2-fluor-N-2-fenyle thyl-karbanilové kyseliny(3-methoxykarbonylaminofenyl)-ester 4-fluor-N-propylkarbanilové kyseliny(3-ethoxykarbonylaminofenyl)-ester 4-fluor-N-propylkarbanilové kyseliny(3-methoxykarbonylaminofenyl)-esterN-butyl-4-fluorkarbanilové kyseliny(3-ethoxykarbonylaminofenyl)-ester 'N-butyl-4-fluorkarbanilové kyseliny[3-(1-methylethoxykarbonylamino)-fenyl] -ester 4-fluor-N-butylkarbanilové kyseliny(3-ethylthiokarbonylaminofenyl)-ester 4-fluor-N-butylkarbanilové kyseliny[3- (2-propinyloxykarbonylaniino) -f enyl] -esterN-butyl-4-fluorkarbanilové kyseliny[3-(ethylthiokarbonylamino)-fenyl] -ester 4-fluor-N-propylkarbanilové kyseliny[3-(2-propinyloxykarbonylamino)-fenyl] -ester 4-fluor-N-propylkarbanilové kyseliny[3-(methylthiokarbonylamino)-fenyl] -esterN-butyl-4-fluorkarbanilové kyseliny[3- (2-propinyloxykarbonylamino)-f enyl]-ester2-fluor-N-(2-fenylethyl)-karbanilové kyseliny teplota tání: 57 až 58 np°: 1,5345 teplota tání: 64 až 66 n£Ď: 1,5322 n^0: 1,5305 teplota tání: 81 až 83 teplota táni: 73 až 75 n^°: 1,5439 teplota tání: 53 až 55 n^0: 1,5461 teplota táni: 85 až 89 teplota táni: 93 až 94: 72 to 73 ° C 7 212336 Name of compound · 2-fluoro-N-2-phenyl-ethyl-carbanilic acid [3- (2-methyl-propoxycarbonylamino) -phenyl] -ester (3-methoxycarbonylaminophenyl) -ester 4-fluoro N-propylcarbanilic acid (3-ethoxycarbonylaminophenyl) ester 4-fluoro-N-propylcarbanilic acid (3-methoxycarbonylaminophenyl) esterN-butyl-4-fluorocarbanilic acid (3-ethoxycarbonylaminophenyl) ester N-butyl-4-fluorocarbanilic acid 4-Fluoro-N-butylcarbanilic acid [3- (1-methyl-ethoxycarbonylamino) -phenyl] -ester 4-fluoro-N-butylcarbanilic acid [3- (2-propyloxycarbonylamino) -phenyl] -esterN 4-fluoro-N-propylcarbanilic acid [3- (2-propynyloxycarbonylamino) phenyl] ester 4-fluoro-N-propylcarbanilic acid [3- (ethylthiocarbonylamino) phenyl] ester [3- (methylthiocarbonylamino) phenyl] ester N-butyl-4-fluorocarbanilic acid [3- (2-propynyloxycarbonylamino) phenyl] ester-2-fluoro-N- (2-phenylethyl) m.p .: 57-58 np °: 1.5345 mp: 64-66 np: 1.5322 n = 0: 1.5305 mp: 81-83 mp: 73-75 n Melting point: 53-55 n ^ 0: 1.5461 Melting point: 85-89 Melting point: 93-94
Sloučeniny podle vynálezu jsou rozpustné v acetonu, cyklohexanonu, isoforonu, tetra-hydrofuranu, dimethylformamidu, dimethylsulfoxidu a ethylesteru kyseliny octové. Následující příklady slouží k objasnění možností použití a to ve srovnání se známýmisloučeninami. Příklad 2The compounds of the invention are soluble in acetone, cyclohexanone, isophorone, tetrahydrofuran, dimethylformamide, dimethylsulfoxide and ethyl acetate. The following examples are intended to illustrate the uses of the compounds as compared to known compounds. Example 2
Ve skleníku byly nastříkány sloučeniny podle vynálezu, uvedené v tabulce v množství5 kg účinné látky/ha emulgované v 500 litrech vody/ha. na Brassica a Solanum jako testo-vané rostliny a to po vyklíčení. Tři týdny po ošetření byl bonitován výsledek ošetření,přičemž 0 = žádný účinek a 4 = zničení rostlin.In the greenhouse, the compounds of the invention listed in the table were sprayed with 5 kg of active ingredient / ha emulsified in 500 liters of water / ha. Brassica and Solanum as test plants after germination. Three weeks after treatment, the treatment result was evaluated, with 0 = no effect and 4 = destruction of the plants.
Je je zřejmé z tabulky, bylo dosaženo zničení testovaných rostlin.It is evident from the table that the destruction of the test plants was achieved.
Sloučeniny podle vynálezuCompounds of the Invention
SolanumSolanum
Brassica (3-methoxykarbonylaminofenyl)-ester 3-fluor-N-methylkarbanilové kyseliny 4 4 (3-methoxykarbonylaminofenyl)-ester N-éthyl-3-fluorkarbanilové kyseliny 8 212336Brassica (3-methoxycarbonylaminophenyl) ester of 3-fluoro-N-methylcarbanilic acid 4 (3-methoxycarbonylaminophenyl) ester of N-ethyl-3-fluorocarbanilic acid 8 212336
Sloučeniny podle vynálezuCompounds of the Invention
SolanumSolanum
Brasslca [3-(methylthiokarbonylamino)-fenyl]-ester N-ethyl-3-fluorkarbanilové kyseliny 4 (3-methoxykarbonylaminof enyl) -ester 4-fluor-N-methylkarbanilové kyseliny 4 [3-(methylthiokarbonylamino)-fenyl]-ester 4-fluor-N-methylkarbanilové kyseliny 4 [3-( methylthiokarbonylamino)-fenyl]-esterN-ethyl-4-fluorkarbanilové kyseliny 4 (3-me thoxykarbony1arainofenyl)-e s ter N-ethyl-4-fluorkarbanilové kyseliny 4 (3-ethoxykarbonylaminofenyl)-ester N-ethyl-4-fluorkarbanilové kyseliny 4 (3-ethoxykarbonylaminofenyl)-ester N-ethyl-3-fluorkarbanilové kyseliny 4 (3-ethoxykarbonylaminofenyl)-e ster 3-fluor-N-methylkarbanilové kyseliny 4 [3-{methylthiokarbonylamino)-fenyl]-ester 3-fluor-N-methylkarbanilové kyseliny 4 [3-(e thylthiokarbonylami no)-fenyl]-e ster 3- fluor-N-methylkarbanilové kyseliny 4 (3-ethoxykarbonylaminofenyl)-ester 4- fluor-N-methylkarbanilové kyseliny 4 (3-methoxykarbohylaminofenyl)-ester 4-fluor-N-(2-fenylethyl)-karbanilové kyseliny 4 (3-ethoxykarbonylaminofenyl)-ester 4-fluor-N-(2-fenylethyl)-karbanilové kyseliny 4 [3-(1-methylethoxykarbonylamino)-fenyl] -esterN-ethyl-3-fluorkarbanilovó kyseliny 4 [3-(1-methylethoxykarbonylamino)-fenyl]-esterŇ-ethyl-4-fluorkarbanilové kyseliny 4 [3-(1-methylethoxykarbonylamino)-fenyl]-ester4-fluor-N-methylkarbanilové kyseliny 4 Γ.3- (ethylthiokarbonylamino, -f enyl] -ester N-ethyl-4-fluorkarbanilové kyseliny , 4 [3—X ethylthiokarbonylamino)-fenyl] -ester 4-fluor-N-methylkarbanilové kyseliny 4 [3-(2-propinyloxykarbonylemino)-fenyl] -ester 3- fluor-N-methylkarbanilové kyseliny 4 [3-(2-propinyloxykarbonylamino)-f enyl] -esterN-ethyl-3-fluorkarbanilové kyseliny 4 [3-(ethylthiokarbonylamino)-fenyl]-ester 4- fluor-N-2-fenylethyl-karbanilové kyseliny 4 F.3-( 1 -methylethoxykarbonylamino)-fenyl]-ester4-fluor-N-(2-fenylethyl)-karbanilové kyseliny 4 (3-allyloxykarbonylaminofenyl)-ester N-ethyl-4-fluorkarbanilové kyseliny 4 (3-allyloxykarbonylaminofenyl)-ester 4-fluor-N- (2-fenylethyl)-karbanilové kyseliny 4 (3-methoxykarbonylaminofenyl)-ester 3-fluor-N-(2-fenylethyl)-karbanilové kyseliny 4 [3-(1-methylethoxykarbonylamino)-fenyl]-ester 3-fluor-N-methylkarbanilové kyseliny 4 (3-allyloxykarbonylaminofenyl)-ester 3-fluor-N-methylkarbanilové kyseliny 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 9 sloučeniny podle vynálezuBrasslca [3- (methylthiocarbonylamino) phenyl] ester N-ethyl-3-fluorocarbanilic acid 4 (3-methoxycarbonylaminophenyl) ester 4-fluoro-N-methylcarbanilic acid 4 [3- (methylthiocarbonylamino) phenyl] ester 4 -fluoro-N-methylcarbanilic acid 4 [3- (methylthiocarbonylamino) phenyl] esterN-ethyl-4-fluorocarbanilic acid 4 (3-methoxycarbonylamino) phenyl esters N-ethyl-4-fluorocarbanilic acid 4 (3-ethoxycarbonylaminophenyl) -ester of N-ethyl-4-fluorocarbanilic acid 4 (3-ethoxycarbonylaminophenyl) ester of N-ethyl-3-fluorocarbanilic acid 4 (3-ethoxycarbonylaminophenyl) ester of 3-fluoro-N-methylcarbanilic acid 4 [3- (methylthiocarbonylamino) -phenyl] -ester of 3-fluoro-N-methylcarbanilic acid 4 [3- (ethylthiocarbonylamino) phenyl] -tert 3-fluoro-N-methylcarbanilic acid 4 (3-ethoxycarbonylaminophenyl) ester 4-fluoro-N- methylcarbanilic acid 4 (3-methoxycarbohylaminophenyl) ester 4-fluoro-N- (2-phenylethyl) carbanilic acid 4 (3-ethoxycarbonylaminophenyl) ester 4-f of 4- [3- (1-methylethoxycarbonylamino) phenyl] ester N-ethyl-3-fluorocarbanilic acid 4- [3- (1-methylethoxycarbonylamino) phenyl] ester-ethyl-ethyl-N- (2-phenylethyl) carboxylic acid 4-fluorocarbanilic acid 4 [3- (1-methylethoxycarbonylamino) -phenyl] -ester-4-fluoro-N-methylcarbanilic acid 4-β- (ethylthiocarbonylamino, -phenyl] -ester N-ethyl-4-fluorocarbanilic acid, 4 [ 3-X-ethylthiocarbonylamino) -phenyl] -ester of 4-fluoro-N-methylcarbanilic acid 4 [3- (2-Propynyloxycarbonylemino) -phenyl] -ester of 3-fluoro-N-methylcarbanilic acid 4 [3- (2-propynyloxycarbonylamino) - 4-Fluoro-N-2-phenylethylcarbanilic acid 4-3- (1-methyl-ethoxycarbonylamino) -phenyl] -phenyl-4-fluoro-N-2-phenylethyl-carboxylic acid phenyl-ester-N-ethyl-3-fluoro-carbanilic acid 4-fluoro-N- (2-phenylethyl) -carbanilic acid ester 4 (3-allyloxycarbonylaminophenyl) ester of N-ethyl-4-fluorocarbanilic acid 4 (3-allyloxycarbonylaminophenyl) ester 4-fluoro-N- (2-phenylethyl) - carbanilic acid 4 (3-me 3-fluoro-N- (2-phenylethyl) carbanilic acid 3-fluoro-N-methylcarbanilic acid 3-fluoro-N- (2-phenylethyl) -carbonylamine ester 4 (3-allyloxycarbonylaminophenyl) ester 3- (3-allyloxycarbonylaminophenyl) ester fluoro-N-methylcarbanilic acids 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 9 compounds of the invention
Solanum 2)2336Solanum 2) 2336
Brassica (3-allyloxykerbonylaminofenyl)-e ster 3- fluor-N-ethylkarbanilové kyseliny 4 4 (3-allyloxykarbonylaminofenyl)-ester 4- fluor-N-methylkarbanilové kyseliny 4 4 [3-(1-chlormethylethoxykarbonylamino)-fenyl]-ester N-ethyl-3-fluorkarbanilové kyseliny 4 4 (3-methoxykarbonylaminofenyl)-ester N-ethyl-2-fluorkarbanilové kyseliny 4 4 (3-methoxykarbonylaminofenyl)-ester N-ethyl-3,4-difluorkarbanilové kyseliny 4 4 (3-ethoxykarbonylaminofenyl)-ester 3-fluor-N-2-fenylethyl-karbanilové kyseliny 4 4 [3-(ethylthiokarbonylamino)-fenyl]ester 3-fluor-N-(2-fenylethyl)-karbanilové kyseliny 4 4 [3-(ethylthiokarbonylamino)-fenyl]-ester 3- fluor-N-(2-fenylethyl)-karbanilové kyseliny 4 4 (3-ethoxykarbonylaminofenyl)-ester N-ethyl-3,4-difluorkarbanilové kyseliny 4 4 [3-(methylthiokarbonylamino)-fenyl]-ester N-ethyl-3,4-difluorkarbanilové kyseliny 4 4 (3-methoxykarbonylaminofenyl)-ester 2-fluor-N-(2-fenylethyl)-karbanilové kyseliny 4 4 (3-ethoxykarbonylaminofenyl)-ester 2-fluor-N-2-fenylethyl-karbanilové kyseliny 4 4 [3-(aethylthiokarbonylamino)-fenyl] -2-fluor- N-(2-fenylethyl)-karbanilové kyseliny 4 4 [3-(e thy1thi o karbonylamino)-fenyl]-ester 2-fluor-N-(2-fenylethyl)-karbanilové kyseliny 4 4 [3-(1-methylethoxykarbonylamino)-fenyl]-e ster 2-fluor-N-(2-fenylethyl)-karbanilové kyseliny 4 4 [3- (2-propinyloxykarbonylamino) -f enyl] -ester 2-fluor-N-(2-fenylethyl)-karbanilové kyseliny 4 4 (3-ethoxykarbonylaminofenyl)-ester N-ethyl-2-fluorkarbanilové kyseliny 4 4 [3-(me thylthiokarbonylamino)-fenyl]-ester N-ethyl-2-fluorkarbanilové kyseliny 4 4 Í3-(ethylthiokarbonylamino)-fenyl]-ester N-ethyl-2-fluorkarbanilové kyseliny 4 4 !. 3- (1 -me thylethoxykarbony lamino) -feny l]-es ter N-ethyl-2-fluorkarbanilové kyseliny 4 4 f3-(2-propinyloxykarbonylamino)-fenyl]-ester N-ethyl-2-fluorkarbanilové kyseliny 4 4 (3-allyloxykarbonylaminofenyl)-ester 2-fluor-N-(2-fenylethyl)-karbanilové kyseliny 4 4 f.3-( 2-methylpropoxykarbonylamino)-fenylJ -ester 2-fluor-N-(2-fenylethyl)-karbanilové kyseliny 4 4 (3-methoxykarbonylaminofenyl)-ester 4- fluor-N-propylkarbanilové kyseliny 4 4 (3-ethoxykarbonylaminofenyl)-ester 4-fluor-N-propylkarbanilové kyseliny 4 4 (3-methoxykarbonylaminofenyl)-ester N-butyl-4-fluorkarbanilové kyseliny ‘4 4 212336 10 sloučeniny podle vynálezu4-Fluoro-N-methylcarbanilic acid 4 (3- (1-chloromethyl-ethoxycarbonylamino) -phenyl) -ester N 4- (3-allyloxycarbonylaminophenyl) -4-fluoro-N-methylcarbanilic acid Brassica (3-allyloxycarbonylaminophenyl) ester 4-ethyl-3-fluorocarbanilic acid 4 (3-methoxycarbonylaminophenyl) ester of N-ethyl-2-fluorocarbanilic acid 4 (3-methoxycarbonylaminophenyl) ester of N-ethyl-3,4-difluorocarbanilic acid 4 4 (3-ethoxycarbonylaminophenyl) 3-Fluoro-N-2-phenylethyl-carbanilic acid ester 4 4-3- (Ethylthiocarbonylamino) -phenyl] ester 3-fluoro-N- (2-phenylethyl) -carbanilic acid 4 [3- (ethylthiocarbonylamino) -phenyl] 3-Fluoro-N- (2-phenylethyl) -carbanilic acid ester 4,4 (3-ethoxycarbonylaminophenyl) ester of N-ethyl-3,4-difluorocarbanilic acid 4 [3- (methylthiocarbonylamino) phenyl] ester N 4-ethyl-3,4-difluorocarbanilic acid 4 (3-methoxycarbonylaminophenyl) ester of 2-fluoro-N- (2-phenylethyl) carbanilic acid 4 4 (3-ethoxycarbonylaminophenyl) ester 2-fluoro-N-2-phenylethyl -to arbanilic acid 4 [3- (aethylthiocarbonylamino) phenyl] -2-fluoro-N- (2-phenylethyl) -carbanilic acid 4 [3- (ethylthiocarbonylamino) phenyl] -ester 2-fluoro-N- (2-phenylethyl) carbanilic acid 4 - [3- (1-Methylethoxycarbonylamino) phenyl] sterene 2-fluoro-N- (2-phenylethyl) carbanilic acid 4 [3- (2-propyloxycarbonylamino) -f] 2-fluoro-N- (2-phenylethyl) carbanilic acid ester 4 (3-ethoxycarbonylaminophenyl) ester of N-ethyl-2-fluorocarbanilic acid 4 [3- (methylthiocarbonylamino) phenyl] ester N N-ethyl-2-fluorocarbanilic acid ester of 4-ethyl-2-fluorocarbanilic acid. 3- (1-methylethoxycarbonylamino) -phenyl] -ester of N-ethyl-2-fluorocarbanilic acid 4, 3- (2-propyloxycarbonylamino) phenyl] ester N-ethyl-2-fluorocarbanilic acid 4 4 (3 2-fluoro-N- (2-phenylethyl) carbanilic acid 4-fluoro-N- (2-phenylethyl) -carbanilic acid 4-fluoro-N- (2-phenylethyl) -carbamic acid 4-fluoro-N- (2-phenylethyl) -carbamic acid ester 4-Fluoro-N-propylcarbanilic acid (3-methoxycarbonylaminophenyl) ester 4-Fluoro-N-propylcarbanilic acid 4 (3-ethoxycarbonylaminophenyl) ester 4-Fluoro-N-butyl-4-fluorocarbanilic acid 4 (3-methoxycarbonylaminophenyl) ester The compound of the invention
SolanumSolanum
Brassica (3-ethoxykarbonylaminofenyl)-ester N-butyl-4-fluorkarbanilové kyseliny 4 [3-( 1-methylethoxykarbonylamino)-fenyl] -ester 4-fluor-N-butylkarbanilové kyseliny 4 (3-ethylthiQkarbonylaminofenyl)-ester 4-fluor-N-butylkarbanilové kyseliny 4 [3-(2-propinyloxykarbonylamino )-fenyl] -esterN-butyl-4-fluorkarbanilové kyseliny 4 (3-ethylthiokarbonylaminofenyl)-ester 4-fluor-N-propylkarbanilové kyseliny 4 [3—(2-propinyloxykarbonylamino)-fenyl] -ester 4-fluor-N-propylkarbanilové kyseliny 4 [3-(methylthiokarbonylamino)-fenyl]-ester N-butyl-4-fluorkanbanilové kyseliny 4 [3-(1-methyl-2-propenyloxykarbonylamino)-fenyl]-esterN-ethyl-3-fluorkarJianilové kyseliny 4 [3-(1-methyl-2-propenyloxykarbonylamino)-fenyl]-esterN-ethyl-fluorkarbanilovó kyseliny e 4 [3-( 1-methyl-2-propenyloxykarbonylaminoJ -fenyl] -esterŇ-ethyl-4-fluorkarbanilové kyseliny 4 (3-methoxykarbonylamino)-fenylester N-buty1-3-fluorkarbánilové kyseliny 4 [3-(2-methylpropoxykarbonylamino)-fenyl]-ester 3- fluor-N-methylkarbanilové kyseliny 4 [3-(1-methyl-2-propenyloxykarbonylamino)-fenyl]-ester 4- fluor-N-(2-fenylethyl)-karbanílové kyseliny 4 [3-(1-methyl-2-propenyloxykarbonylamino)-fenyl]-ester 3-fluor-N-(2-fenylethyl)-karbainilóvé kyseliny 4 [3-(l-methyl-2-propenyloxykarbonylamino)-fenyl]-ester3-fluor-N-(2-fenylethyl)-karbanilové kyseliny 4 [3-(1-methyl-2-propenyloxykarbonylamino)-fenyl]-ester 3- fluor-N-methylkarbanilové kyseliny 4 [3-(1-methyl-2-propenyloxykarbonylamino)-fenyl]-ester 4- fluor-N-methylkarbanilové kyseliny 4 [3-(1-methyl-2-propenyloxykarbonylamino)-fenyl]-esterN-butyl-4-fluorkarbanilové kyseliny 4 [3-(2-me thylpropoxykarbonylamirio)-fenyl]-ester 4-fluor-N-methylkarbanilové kyseliny 4 (3-methoxykarbonylamino)-fenylester 3-fluor-N-propylkarbanilové kyseliny 4 [3-(methylthiokarbonylamino)-fenyl]-ester 3-fluor-N-propylkarbanilové kyseliny 4 (3-ethoxykarbonylamino)-fenylester 3-fluor-N-propylkarbanilové kyseliny 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 Příklad 3Brassica (3-ethoxycarbonylaminophenyl) ester of N-butyl-4-fluorocarbanilic acid 4 [3- (1-Methylethoxycarbonylamino) phenyl] ester 4-fluoro-N-butylcarbanilic acid 4 (3-ethylthiocarbonylaminophenyl) ester 4-fluoro- N-butylcarbanilic acid 4 [3- (2-propyloxycarbonylamino) phenyl] ester N-butyl-4-fluorocarbanilic acid 4 (3-ethylthiocarbonylaminophenyl) ester 4-fluoro-N-propylcarbanilic acid 4 [3- (2-propynyloxycarbonylamino) 4-Fluoro-N-propylcarbanilic acid 4-phenyl-4-fluoro-4-fluoroanbanilic acid [3- (1-methyl-2-propenyloxycarbonylamino) -phenyl] -phenyl] ester 4-fluoro-N-propylcarbanilic acid N-ethyl-3-fluorocarboxylic acid ester 4 [3- (1-methyl-2-propenyloxycarbonylamino) phenyl] ester N-ethylfluorocarbonic acid e [3- (1-methyl-2-propenyloxycarbonylamino) phenyl] ester- of ethyl 4-fluorocarbanilic acid 4 (3-methoxycarbonylamino) phenyl ester of N-butyl-3-fluorocarbonylic acid 4 [3- (2-methylpropoxycarbonylamino) phenyl] ester 3-fluoro-N-methyl Carbanilic acid 4 [4- (1-Methyl-2-propenyloxycarbonylamino) -phenyl]-4-fluoro-N- (2-phenylethyl) -carbanilic acid ester 4 [3- (1-methyl-2-propenyloxycarbonylamino) -phenyl] 3-Fluoro-N- (2-phenylethyl) -carbainilic acid ester of [3- (1-methyl-2-propenyloxycarbonylamino) -phenyl] -ester 3-fluoro-N- (2-phenylethyl) -carbanilic acid 4 [3 3-Fluoro-N-methylcarbanilic acid 4-fluoro-N-methylcarbanilic acid 3- (1-methyl-2-propenyloxycarbonylamino) phenyl] - (1-methyl-2-propenyloxycarbonylamino) -phenyl] -ester 4 [3- (1-methyl-2-propenyloxycarbonylamino) phenyl] ester N-butyl-4-fluorocarbanilic acid 4-Fluoro-N-methylcarbanilic acid 4 [3- (2-methylpropoxycarbonylamino) phenyl] ester (3) 3-Fluoro-N-propylcarbanilic acid-methoxycarbonylamino) -phenyl ester 3-fluoro-N-propylcarbanilic acid 3 - (3-ethoxycarbonylamino) -phenyl ester 3-fluoro-N-propylcarbanilic acid 4 [3- (methylthiocarbonylamino) phenyl] 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 Example 3
Ve skleníku byly před vyklíčením postříkány Brassica a Solanum jako testovanérostliny sloučeninami podle vynálezu, uvedenými v tabulce použitým množstvím 5 kg účinnélátky/ha emulgované v 600 litrech vody /ha. Po třech týdnech po ošetření byl bonitovánvýsledek ošetření, přičemž 11 212336 O = žádný účinek a 4 = zničení rostlin.In the greenhouse, Brassica and Solanum were sprayed as test plants prior to germination with the compounds of the invention listed in the table using an amount of 5 kg of active ingredient / ha emulsified in 600 liters of water / ha. Three weeks after treatment, the treatment result was evaluated, with 11,212,336 O = no effect and 4 = plant destruction.
Jak je zřejmé z tabulky bylo dosaženo zničení testovaných rostlin.As shown in the table, the destruction of the test plants was achieved.
Sloučeniny podle vynálezuCompounds of the Invention
SolanumSolanum
Brassica (3-methoxykarbonylaminofenyl)-ester 4-fluor-N-methylkarbanilové kyseliny 4 4 (3-methoxykarbonylaminofenyl)-ester N-ethyl-4-fluorkarbanilové kyseliny 4 4 (3-ethoxykarbonylaminofenylí-ester N-ethyl-4-fluorkarbanilové kyseliny 4 4 (3-ethoxykarbonylaminofenyl)-ester 4-fluor-N-methylkarbanilové kyseliny 4 4 [3-(1-methyletoxykarbonylamino)-fenyl] -ester N-ethyl-4-fluorkarbanilové kyseliny 4 4 neošetřeno 0 0 Příklad 4Brassica (3-methoxycarbonylaminophenyl) ester of 4-fluoro-N-methylcarbanilic acid 4 4 (3-methoxycarbonylaminophenyl) ester of N-ethyl-4-fluorocarbanilic acid 4 4 (3-ethoxycarbonylaminophenyl ester of N-ethyl-4-fluorocarbanilic acid 4 4 (3-ethoxycarbonylaminophenyl) ester of 4-fluoro-N-methylcarbanilic acid 4 [3- (1-methylethoxycarbonylamino) phenyl] -ester of N-ethyl-4-fluorocarbanilic acid 4 4 untreated 0 0 Example 4
Ve skleníku byly ošetřeny rostliny, uvedené v následující tabulce, po vyklíčení uve-denými prostředky v použitém množství 1 kg účinné látky/ha. Prostředky byly za tímtoúčelem rozprášeny rovnoměrně nad rostlinami. Prostředky podle vynálezu zde vykazovaly3 týdny po ošetření vysokou selektivitu při současně vynikajícím účinku na plevel.Srovnávací prostředky nevykazovaly žádnou selektivitu.In the greenhouse, the plants listed in the following table were treated after germination with the indicated compositions in an amount of 1 kg of active ingredient / ha. The compositions were sprayed evenly over the plants. The compositions of the invention exhibited a high selectivity at the same time 3 weeks after treatment with an excellent weed effect. Comparative compositions showed no selectivity.
Sloučeniny podle vyná-lezu podzem- niceolejná bavl- ník kuku- řice- rýže Ama- ran- thus Ipo- mea Seta- ria Echi- no- chloa (3-ethoxykarbonylamino-fenyl)~ester N-ethyl-3--fluorkarbanilové kyseliny 10 ,0 10 ,0 0 0 0 0 3-methoxykarbonylamino-fenl)-ester N-ethyl-3-fluorkarbanilové kyse-liny 10 10 10 0 0 0 0 [3-(1-methyletoxykarbonyl-amino)-fenyl]-ester N--ethyl-3-fluorkarbanilovékyseliny 10 ,0 10 10 0 0 0 0 £}-( 1-methylethoxykarbonyl-amino)-fenyl]-ester N-ethyl--4-fluorkarbanilové kyseliny 10 10 10 10 0 0 0 0 Srovnávané, prostředkymetyl-N-(3-N'-(3'-methyl-fenyl)-karbamoyloxy)-fe-nyl)-karbamid (podle NSHpat. ,567151) 10 1 2 10 6 1 3 6Compounds according to the invention of groundwater cotton-maize-rice-hanum-Ipo- mea seed Setaria Echinchloa (3-ethoxycarbonylamino-phenyl) ester of N-ethyl-3-fluorocarbanilic acid 10, 0 10, 0 0 0 0 0 3-methoxycarbonylamino-phenyl-ester of N-ethyl-3-fluorocarbanilic acid 10 10 10 0 0 0 [3- (1-methylethoxycarbonyl-amino) -phenyl] -ester N-ethyl-3-fluorocarbanilic acids 10, 0 10 10 0 0 0 0 - (1-methylethoxycarbonyl-amino) -phenyl] -ester N-ethyl - 4-fluorocarbanilic acids 10 10 10 10 0 0 0 0 Comparative , methyl-N- (3-N '- (3'-methyl-phenyl) -carbamoyloxy) -phenyl) -carbamide (NSHpat., 567151) 10 1 2 10 6 1 3 6
Claims (2)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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DE19792901658 DE2901658A1 (en) | 1979-01-15 | 1979-01-15 | DIURETHANE, METHOD FOR PRODUCING THESE COMPOUNDS AND HERBICIDES CONTAINING THEM |
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CS212336B2 true CS212336B2 (en) | 1982-03-26 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CS80312A CS212336B2 (en) | 1979-01-15 | 1980-01-15 | Herbicide means and method of making the active substances of the same |
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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) |
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ZA (1) | ZA80244B (en) |
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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 | SHIRIKONNODOOPINGUHOHO |
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
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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 SU SU802867755A patent/SU942587A3/en active
- 1980-01-11 AT AT0013980A patent/AT365411B/en not_active IP Right Cessation
- 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
- 1980-01-12 EG EG21/80A patent/EG14116A/en active
- 1980-01-14 BG BG046235A patent/BG31465A3/en unknown
- 1980-01-14 PT PT70692A patent/PT70692A/en unknown
- 1980-01-14 RO RO8099869A patent/RO79454A/en unknown
- 1980-01-14 MA MA18899A patent/MA18702A1/en unknown
- 1980-01-14 SE SE8000278A patent/SE8000278L/en not_active Application Discontinuation
- 1980-01-14 IL IL59126A patent/IL59126A/en unknown
- 1980-01-14 BG BG046234A patent/BG31495A3/en unknown
- 1980-01-14 HU HU8063A patent/HU181682B/en unknown
- 1980-01-14 CA CA343,600A patent/CA1128061A/en not_active Expired
- 1980-01-14 IT IT19194/80A patent/IT1130864B/en active
- 1980-01-14 PL PL1980221361A patent/PL125248B1/en unknown
- 1980-01-14 GR GR60957A patent/GR71679B/el unknown
- 1980-01-15 FR FR8000793A patent/FR2446275A1/en active Granted
- 1980-01-15 AU AU54604/80A patent/AU532736B2/en not_active Ceased
- 1980-01-15 BE BE0/198971A patent/BE881152A/en not_active IP Right Cessation
- 1980-01-15 GB GB8001303A patent/GB2040939B/en not_active Expired
- 1980-01-15 DK DK16380A patent/DK16380A/en not_active Application Discontinuation
- 1980-01-15 ES ES487720A patent/ES487720A1/en not_active Expired
- 1980-01-15 ZA ZA00800244A patent/ZA80244B/en unknown
- 1980-01-15 CS CS80312A patent/CS212336B2/en unknown
- 1980-01-15 CH CH32280A patent/CH645343A5/en not_active IP Right Cessation
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