CS220795B2 - Herbicide means and method of making the active substances - Google Patents
Herbicide means and method of making the active substances Download PDFInfo
- Publication number
- CS220795B2 CS220795B2 CS796923A CS692379A CS220795B2 CS 220795 B2 CS220795 B2 CS 220795B2 CS 796923 A CS796923 A CS 796923A CS 692379 A CS692379 A CS 692379A CS 220795 B2 CS220795 B2 CS 220795B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- phenyl
- ester
- acid
- alkyl
- methyl
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 10
- 239000013543 active substance Substances 0.000 title description 4
- 239000004009 herbicide Substances 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- -1 1,3-dioxolan-2-yl-methyl Chemical group 0.000 claims abstract description 66
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 38
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 241000894007 species Species 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- AAPAVYWERMFERN-UHFFFAOYSA-N ethyl(phenyl)carbamic acid Chemical compound CCN(C(O)=O)C1=CC=CC=C1 AAPAVYWERMFERN-UHFFFAOYSA-N 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 235000011331 Brassica Nutrition 0.000 description 4
- 241000219198 Brassica Species 0.000 description 4
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 4
- 241000207763 Solanum Species 0.000 description 4
- 235000002634 Solanum Nutrition 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- 239000012267 brine Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019271 petrolatum Nutrition 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 description 1
- AZRFSRYROARRET-UHFFFAOYSA-N (3,4-dichlorophenyl)-methylcarbamic acid Chemical compound OC(=O)N(C)C1=CC=C(Cl)C(Cl)=C1 AZRFSRYROARRET-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- WZRJTRPJURQBRM-UHFFFAOYSA-N 4-amino-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide;5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1.COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 WZRJTRPJURQBRM-UHFFFAOYSA-N 0.000 description 1
- 240000006995 Abutilon theophrasti Species 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 241000743339 Agrostis Species 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000219318 Amaranthus Species 0.000 description 1
- 241001377087 Amsinckia Species 0.000 description 1
- 244000277177 Anchusa azurea Species 0.000 description 1
- 241001547866 Anoda Species 0.000 description 1
- 241000219305 Atriplex Species 0.000 description 1
- 235000005781 Avena Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 241001072256 Boraginaceae Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000012905 Brassica oleracea var viridis Nutrition 0.000 description 1
- 241000219193 Brassicaceae Species 0.000 description 1
- 241000209200 Bromus Species 0.000 description 1
- 241000220244 Capsella <angiosperm> Species 0.000 description 1
- 241000132570 Centaurea Species 0.000 description 1
- 241000219294 Cerastium Species 0.000 description 1
- 241000871189 Chenopodiaceae Species 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- 235000000509 Chenopodium ambrosioides Nutrition 0.000 description 1
- 244000098897 Chenopodium botrys Species 0.000 description 1
- 235000005490 Chenopodium botrys Nutrition 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 240000005250 Chrysanthemum indicum Species 0.000 description 1
- 244000192528 Chrysanthemum parthenium Species 0.000 description 1
- 244000298479 Cichorium intybus Species 0.000 description 1
- 235000007542 Cichorium intybus Nutrition 0.000 description 1
- 241000207782 Convolvulaceae Species 0.000 description 1
- 241000234646 Cyperaceae Species 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- 241000208296 Datura Species 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 241000202296 Delphinium Species 0.000 description 1
- 240000001879 Digitalis lutea Species 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- 235000007351 Eleusine Nutrition 0.000 description 1
- 241000209215 Eleusine Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000221079 Euphorbia <genus> Species 0.000 description 1
- 241000221017 Euphorbiaceae Species 0.000 description 1
- 241000220485 Fabaceae Species 0.000 description 1
- 241000234642 Festuca Species 0.000 description 1
- 241000816457 Galeopsis Species 0.000 description 1
- 241000748465 Galinsoga Species 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000208818 Helianthus Species 0.000 description 1
- 235000005206 Hibiscus Nutrition 0.000 description 1
- 235000007185 Hibiscus lunariifolius Nutrition 0.000 description 1
- 244000284380 Hibiscus rosa sinensis Species 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000110847 Kochia Species 0.000 description 1
- 241000208822 Lactuca Species 0.000 description 1
- 241000207923 Lamiaceae Species 0.000 description 1
- 241000520028 Lamium Species 0.000 description 1
- 241000234280 Liliaceae Species 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 241000209082 Lolium Species 0.000 description 1
- 241000219071 Malvaceae Species 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- 241000219823 Medicago Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 241001442129 Myosotis Species 0.000 description 1
- MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 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
- 240000001090 Papaver somniferum Species 0.000 description 1
- 241000745991 Phalaris Species 0.000 description 1
- 241000746981 Phleum Species 0.000 description 1
- 244000064622 Physalis edulis Species 0.000 description 1
- 241000013557 Plantaginaceae Species 0.000 description 1
- 241000209048 Poa Species 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 241000219295 Portulaca Species 0.000 description 1
- 241000219304 Portulacaceae Species 0.000 description 1
- 241000593769 Richardia <angiosperm> Species 0.000 description 1
- 241001107098 Rubiaceae Species 0.000 description 1
- 241001632050 Salsola Species 0.000 description 1
- 241000780602 Senecio Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- 241000208292 Solanaceae Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 241000722118 Thlaspi Species 0.000 description 1
- 241000219793 Trifolium Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 241000219422 Urtica Species 0.000 description 1
- 241000218215 Urticaceae Species 0.000 description 1
- 241001506766 Xanthium Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HJUCFHJKOMOFLF-UHFFFAOYSA-N [3-(2,2-dimethylpentanoylamino)phenyl] N-ethyl-N-(3-methylphenyl)carbamate Chemical compound CC(C(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)C)CC)=O)(CCC)C HJUCFHJKOMOFLF-UHFFFAOYSA-N 0.000 description 1
- BTQGBXUOMZVPKR-UHFFFAOYSA-N [3-(2,2-dimethylpentanoylamino)phenyl] N-phenyl-N-prop-2-ynylcarbamate Chemical compound CC(C(=O)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)CC#C)=O)(CCC)C BTQGBXUOMZVPKR-UHFFFAOYSA-N 0.000 description 1
- WXDPUPUPGWNBAR-UHFFFAOYSA-N [3-(2,2-dimethylpropanoylamino)phenyl] N-ethyl-N-(3-methylphenyl)carbamate Chemical compound C(C)(C)(C)C(=O)NC=1C=C(C=CC=1)OC(N(C1=CC(=CC=C1)C)CC)=O WXDPUPUPGWNBAR-UHFFFAOYSA-N 0.000 description 1
- UYLWDQPATURMTE-UHFFFAOYSA-N [3-(2-methylpropanoylamino)phenyl] N-(2-methylpropyl)-N-phenylcarbamate Chemical compound CC(C(=O)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)CC(C)C)=O)C UYLWDQPATURMTE-UHFFFAOYSA-N 0.000 description 1
- UHXZHLUWVRGMHL-UHFFFAOYSA-N [3-(2-methylpropanoylamino)phenyl] N-butyl-N-phenylcarbamate Chemical compound CC(C(=O)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)CCCC)=O)C UHXZHLUWVRGMHL-UHFFFAOYSA-N 0.000 description 1
- SLXZURMNOLYVHK-UHFFFAOYSA-N [3-(2-methylpropanoylamino)phenyl] N-ethyl-N-phenylcarbamate Chemical compound CC(C(=O)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)CC)=O)C SLXZURMNOLYVHK-UHFFFAOYSA-N 0.000 description 1
- CSTQWVFMHDQBCX-UHFFFAOYSA-N [3-(propanoylamino)phenyl] N-(3-chlorophenyl)-N-methylcarbamate Chemical compound C(CC)(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)Cl)C)=O CSTQWVFMHDQBCX-UHFFFAOYSA-N 0.000 description 1
- BWCANCOERCUQOA-UHFFFAOYSA-N [3-(propanoylamino)phenyl] N-ethyl-N-(3-fluorophenyl)carbamate Chemical compound C(CC)(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)CC)=O BWCANCOERCUQOA-UHFFFAOYSA-N 0.000 description 1
- KOTLSRKUXQKANW-UHFFFAOYSA-N [3-(propanoylamino)phenyl] N-ethyl-N-(4-fluorophenyl)carbamate Chemical compound C(CC)(=O)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)F)CC)=O KOTLSRKUXQKANW-UHFFFAOYSA-N 0.000 description 1
- SYZLRWKFUVSGCH-UHFFFAOYSA-N [3-(propanoylamino)phenyl] N-methyl-N-phenylcarbamate Chemical compound C(CC)(=O)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)C)=O SYZLRWKFUVSGCH-UHFFFAOYSA-N 0.000 description 1
- GCKSXEOCGVNIJM-UHFFFAOYSA-N [3-(propanoylamino)phenyl] N-phenyl-N-prop-2-ynylcarbamate Chemical compound C(CC)(=O)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)CC#C)=O GCKSXEOCGVNIJM-UHFFFAOYSA-N 0.000 description 1
- ILZLKUFTMSDABQ-UHFFFAOYSA-N [3-[(2,2,2-trichloroacetyl)amino]phenyl] carbonochloridate Chemical compound ClC(=O)OC1=CC=CC(NC(=O)C(Cl)(Cl)Cl)=C1 ILZLKUFTMSDABQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- GPFIZJURHXINSQ-UHFFFAOYSA-N acetic acid;nitric acid Chemical compound CC(O)=O.O[N+]([O-])=O GPFIZJURHXINSQ-UHFFFAOYSA-N 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 235000012211 aluminium silicate Nutrition 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
- 238000009835 boiling Methods 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical compound NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 239000002837 defoliant Substances 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
- 238000001035 drying Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000003977 halocarboxylic acids Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 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
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- GAUSUDNBBOZKSB-UHFFFAOYSA-N methyl(phenyl)carbamic acid Chemical compound OC(=O)N(C)C1=CC=CC=C1 GAUSUDNBBOZKSB-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 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
- YMPKWMGLBHVDBS-UHFFFAOYSA-N n-(3-hydroxyphenyl)-2,2-dimethylpentanamide Chemical compound CCCC(C)(C)C(=O)NC1=CC=CC(O)=C1 YMPKWMGLBHVDBS-UHFFFAOYSA-N 0.000 description 1
- YXSKGOCVSTWEJU-UHFFFAOYSA-N n-(3-hydroxyphenyl)propanamide Chemical compound CCC(=O)NC1=CC=CC(O)=C1 YXSKGOCVSTWEJU-UHFFFAOYSA-N 0.000 description 1
- MBSPOYRKNIDVOA-UHFFFAOYSA-N n-ethyl-4-fluoroaniline Chemical compound CCNC1=CC=C(F)C=C1 MBSPOYRKNIDVOA-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
- 230000007935 neutral effect Effects 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- KBKRAQOHVVQXAC-UHFFFAOYSA-N phenyl(propyl)carbamic acid Chemical compound CCCN(C(O)=O)C1=CC=CC=C1 KBKRAQOHVVQXAC-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000000376 reactant Substances 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
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil 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
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 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
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782844806 DE2844806A1 (de) | 1978-10-11 | 1978-10-11 | Carbanilsaeure- eckige klammer auf 3-(alkylcarbonylamino)-phenyl eckige klammer zu -ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes herbizides mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS220795B2 true CS220795B2 (en) | 1983-04-29 |
Family
ID=6052185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS796923A CS220795B2 (en) | 1978-10-11 | 1979-10-11 | Herbicide means and method of making the active substances |
Country Status (32)
| Country | Link |
|---|---|
| US (4) | US4344790A (ro) |
| JP (1) | JPS5553256A (ro) |
| AU (1) | AU534106B2 (ro) |
| BE (1) | BE879348A (ro) |
| BG (1) | BG30617A3 (ro) |
| BR (1) | BR7906466A (ro) |
| CA (1) | CA1123854A (ro) |
| CH (1) | CH641767A5 (ro) |
| CS (1) | CS220795B2 (ro) |
| DD (1) | DD146385A5 (ro) |
| DE (1) | DE2844806A1 (ro) |
| ES (1) | ES484974A1 (ro) |
| FI (1) | FI792897A7 (ro) |
| FR (1) | FR2438647A1 (ro) |
| GB (1) | GB2034697B (ro) |
| GR (1) | GR72474B (ro) |
| HU (1) | HU180988B (ro) |
| IL (1) | IL58418A (ro) |
| IN (1) | IN153181B (ro) |
| IT (1) | IT1166911B (ro) |
| MA (1) | MA18606A1 (ro) |
| MX (1) | MX6131E (ro) |
| NL (1) | NL7906464A (ro) |
| PH (1) | PH15392A (ro) |
| PL (1) | PL117898B1 (ro) |
| PT (1) | PT70288A (ro) |
| RO (1) | RO79316A (ro) |
| SE (1) | SE7908191L (ro) |
| SU (1) | SU936806A3 (ro) |
| TR (1) | TR20544A (ro) |
| YU (1) | YU239279A (ro) |
| ZA (1) | ZA795437B (ro) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2844806A1 (de) | 1978-10-11 | 1980-04-24 | Schering Ag | Carbanilsaeure- eckige klammer auf 3-(alkylcarbonylamino)-phenyl eckige klammer zu -ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes herbizides mittel |
| FI70774C (fi) * | 1982-05-27 | 1986-10-27 | Stauffer Chemical Co | Synergistiska herbicidblandningar |
| DE3804288A1 (de) * | 1987-06-03 | 1988-12-15 | Bayer Ag | Substituierte aminophenyl-carbamate |
| US5260474A (en) * | 1987-06-03 | 1993-11-09 | Bayer Aktiengesellschaft | Pesticidal substituted aminophenyl carbamates |
| MXPA02002578A (es) * | 1999-09-08 | 2002-10-23 | Guilford Pharm Inc | Compuestos de union a ciclofilina no peptidicos, y su uso. |
| CA2435829A1 (en) | 2001-01-25 | 2002-08-01 | Guilford Pharmaceuticals Inc. | Trisubstituted carbocyclic cyclophilin binding compounds and their use |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH477172A (de) | 1965-05-18 | 1969-08-31 | Agripat Sa | Beifuttermittel |
| IL26406A (en) | 1965-09-01 | 1970-07-19 | Stauffer Chemical Co | Alkanamidophenyl carbamates and herbicidal compositions containing them |
| US3865867A (en) * | 1967-06-19 | 1975-02-11 | Monsanto Co | Meta-bifunctional benzenes |
| LU56289A1 (ro) * | 1967-06-19 | 1969-04-22 | ||
| US3872157A (en) * | 1967-10-23 | 1975-03-18 | Stauffer Chemical Co | Substituted anilide carbamates |
| US3592949A (en) | 1968-03-29 | 1971-07-13 | Stauffer Chemical Co | Acylated anilide carbamates |
| US3836570A (en) * | 1968-04-08 | 1974-09-17 | Stauffer Chemical Co | M-amidophenylcarbamates |
| CA975775A (en) * | 1969-03-12 | 1975-10-07 | Eugene G. Teach | Bromoacetanilides and their utility as biocides |
| US3892786A (en) | 1969-03-12 | 1975-07-01 | Stauffer Chemical Co | Bromoacetanilides and their utility as biocides |
| US3979202A (en) * | 1970-05-26 | 1976-09-07 | Monsanto Company | Meta-bifunctional benzenes and herbicidal compositions |
| US3714219A (en) | 1971-03-24 | 1973-01-30 | Stauffer Chemical Co | Carbonates of 3'-and 4'-hydroxy bromoacetanilides |
| US3898273A (en) * | 1971-03-24 | 1975-08-05 | Stauffer Chemical Co | Esterified bromoacetanilides |
| US3836564A (en) * | 1971-03-24 | 1974-09-17 | Stauffer Chemical Co | Sulfonyloxy bromoacetanilides and their utility as biocides |
| FR2210186A5 (en) * | 1972-12-13 | 1974-07-05 | Rhone Progil | Halogenated ureidophenyl carbamates - herbicides, by reacting corresp. halophenols and isocyanates |
| US3792994A (en) * | 1972-12-26 | 1974-02-19 | Stauffer Chemical Co | Anilide carbamates as algicidal agents |
| US3888906A (en) | 1974-05-02 | 1975-06-10 | Stauffer Chemical Co | Ortho-carbamyloxy-benzamide bactericides |
| DE2844806A1 (de) | 1978-10-11 | 1980-04-24 | Schering Ag | Carbanilsaeure- eckige klammer auf 3-(alkylcarbonylamino)-phenyl eckige klammer zu -ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes herbizides mittel |
| DE2844811A1 (de) * | 1978-10-12 | 1980-09-04 | Schering Ag | Carbaminsaeurephenylester, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes herbizides mittel |
-
1978
- 1978-10-11 DE DE19782844806 patent/DE2844806A1/de not_active Withdrawn
-
1979
- 1979-08-28 NL NL7906464A patent/NL7906464A/nl not_active Application Discontinuation
- 1979-09-14 IN IN643/DEL/79A patent/IN153181B/en unknown
- 1979-09-18 FI FI792897A patent/FI792897A7/fi not_active Application Discontinuation
- 1979-09-25 MX MX798397U patent/MX6131E/es unknown
- 1979-09-28 TR TR20544A patent/TR20544A/xx unknown
- 1979-10-01 GB GB7933947A patent/GB2034697B/en not_active Expired
- 1979-10-02 MA MA18806A patent/MA18606A1/fr unknown
- 1979-10-02 YU YU02392/79A patent/YU239279A/xx unknown
- 1979-10-03 IT IT26210/79A patent/IT1166911B/it active
- 1979-10-03 SE SE7908191A patent/SE7908191L/ not_active Application Discontinuation
- 1979-10-08 PT PT70288A patent/PT70288A/pt unknown
- 1979-10-08 BR BR7906466A patent/BR7906466A/pt unknown
- 1979-10-09 BG BG045093A patent/BG30617A3/xx unknown
- 1979-10-09 PL PL1979218815A patent/PL117898B1/pl unknown
- 1979-10-09 GR GR60221A patent/GR72474B/el unknown
- 1979-10-09 IL IL58418A patent/IL58418A/xx unknown
- 1979-10-09 DD DD79216117A patent/DD146385A5/de unknown
- 1979-10-10 SU SU792824350A patent/SU936806A3/ru active
- 1979-10-10 AU AU51634/79A patent/AU534106B2/en not_active Ceased
- 1979-10-10 HU HU79SCHE695A patent/HU180988B/hu unknown
- 1979-10-10 CH CH911479A patent/CH641767A5/de not_active IP Right Cessation
- 1979-10-10 PH PH23151A patent/PH15392A/en unknown
- 1979-10-11 JP JP13008579A patent/JPS5553256A/ja active Granted
- 1979-10-11 BE BE0/197593A patent/BE879348A/fr not_active IP Right Cessation
- 1979-10-11 RO RO7998911A patent/RO79316A/ro unknown
- 1979-10-11 FR FR7925310A patent/FR2438647A1/fr active Pending
- 1979-10-11 ES ES484974A patent/ES484974A1/es not_active Expired
- 1979-10-11 CS CS796923A patent/CS220795B2/cs unknown
- 1979-10-11 ZA ZA00795437A patent/ZA795437B/xx unknown
- 1979-10-11 CA CA337,401A patent/CA1123854A/en not_active Expired
- 1979-10-23 US US06/087,637 patent/US4344790A/en not_active Expired - Lifetime
-
1982
- 1982-01-04 US US06/337,003 patent/US4426222A/en not_active Expired - Fee Related
- 1982-01-04 US US06/337,004 patent/US4453973A/en not_active Expired - Fee Related
- 1982-01-04 US US06/337,001 patent/US4453966A/en not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4055410A (en) | Substituted bromo- or chloroacetamide herbicides | |
| US4097262A (en) | Herbicidal acetamides | |
| LT3521B (en) | Methods for weeds control | |
| CS220795B2 (en) | Herbicide means and method of making the active substances | |
| CS227322B2 (en) | Herbicide and method of preparing active substance thereof | |
| US4144049A (en) | N-(4-Benzyloxyphenyl)-N-methyl-N-methoxyurea | |
| US4029688A (en) | Carbamic pesticidal compositions | |
| US4138423A (en) | N-dithio carbamoyl oximes | |
| PL118237B1 (en) | Biocide | |
| CS247172B2 (en) | Fungicide and method of active substance preparation | |
| HU181859B (en) | Fungicide compositions containing 3-bracket-n-acyl-n-aryl-amino-bracket closed-gamma-butirolaktone- or 3-bracket-n-acyl-n-aryl-amino-bracket closed-gamma-butirolactone derivatives as active agents, and process for producing the active agents | |
| DD147040A5 (de) | Herbizides mittel | |
| US5312798A (en) | Herbicidal composition | |
| CS208137B2 (en) | Herbicide means and method of making the active substances | |
| US4639268A (en) | Nitro- and cyanoguanidines as selective preemergence herbicides and plant defoliants | |
| US4944795A (en) | 3-butenanilides | |
| US5175365A (en) | Nitro- and cyanoguanidines as selective preemergence herbicides and plant defoliants | |
| KR840000588B1 (ko) | 제초제로 유용한 카바민산페닐 에스테르의 제법 | |
| CS247077B2 (en) | Herbicide and microbicide agent and production method of effective substances | |
| DK156390B (da) | Nitroalkanolderivater | |
| HU182605B (en) | Selective herbicide compositions containing substituted esters of carbanilic acid | |
| CS235028B2 (en) | Growth regulating and husking causing agents and method of their effective substance production | |
| CS209949B2 (en) | Herbicide means and method of making the active substance | |
| US3963474A (en) | Herbicide mixtures of 3-lower alkyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxides or salts thereof and 2-(methyl, chlorophenoxy)-N-methoxyacetamides | |
| CS195336B2 (en) | Herbicide and process for preparing effective compound thereof |