CS207787B2 - Selective herbicide means and method of making its active substance - Google Patents
Selective herbicide means and method of making its active substance Download PDFInfo
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- CS207787B2 CS207787B2 CS792753A CS275379A CS207787B2 CS 207787 B2 CS207787 B2 CS 207787B2 CS 792753 A CS792753 A CS 792753A CS 275379 A CS275379 A CS 275379A CS 207787 B2 CS207787 B2 CS 207787B2
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- salts
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- acids
- amides
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- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 239000013543 active substance Substances 0.000 title description 7
- 239000004009 herbicide Substances 0.000 title description 4
- -1 3-methoxyl-N-ethylcarbanilic acid phenyl ester Chemical compound 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- CDGCUPPKLDOYGV-UHFFFAOYSA-N n-ethyl-n-phenylcarbamoyl chloride Chemical compound CCN(C(Cl)=O)C1=CC=CC=C1 CDGCUPPKLDOYGV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- LCEYJTJDZROKOK-UHFFFAOYSA-N (3-hydroxyphenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC(O)=C1 LCEYJTJDZROKOK-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 14
- 244000105624 Arachis hypogaea Species 0.000 abstract description 6
- 229920000742 Cotton Polymers 0.000 abstract description 4
- 240000007594 Oryza sativa Species 0.000 abstract description 4
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 4
- 235000009566 rice Nutrition 0.000 abstract description 4
- 235000010777 Arachis hypogaea Nutrition 0.000 abstract description 3
- 241000219146 Gossypium Species 0.000 abstract description 3
- 235000003276 Apios tuberosa Nutrition 0.000 abstract description 2
- 235000010744 Arachis villosulicarpa Nutrition 0.000 abstract description 2
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 150000001408 amides Chemical class 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 235000020232 peanut Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 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
- 230000006378 damage Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000016068 Berberis vulgaris Nutrition 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- 239000005594 Phenmedipham Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 244000038559 crop plants Species 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000002019 disulfides Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- FFQQCJGNKKIRMD-UHFFFAOYSA-N methyl n-(3-hydroxyphenyl)carbamate Chemical compound COC(=O)NC1=CC=CC(O)=C1 FFQQCJGNKKIRMD-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- XIZDNZVKQNBGGR-UHFFFAOYSA-N (3-aminophenyl) n-ethyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(CC)C(=O)OC1=CC=CC(N)=C1 XIZDNZVKQNBGGR-UHFFFAOYSA-N 0.000 description 1
- UXJXCTURSMEGTA-UHFFFAOYSA-N (3-nitrophenyl) n-ethyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(CC)C(=O)OC1=CC=CC([N+]([O-])=O)=C1 UXJXCTURSMEGTA-UHFFFAOYSA-N 0.000 description 1
- ARIOIRXTWLTVPY-UHFFFAOYSA-N (4-ethylphenyl)carbamic acid Chemical compound CCC1=CC=C(NC(O)=O)C=C1 ARIOIRXTWLTVPY-UHFFFAOYSA-N 0.000 description 1
- FTDGDIFUDKDKAW-UHFFFAOYSA-N 1,1a,5,5a,6,6a-hexahydrocyclopropa[a]indene Chemical class C12C(CC3CC=CC=C13)C2 FTDGDIFUDKDKAW-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical class C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical class OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 1
- REEXLQXWNOSJKO-UHFFFAOYSA-N 2h-1$l^{4},2,3-benzothiadiazine 1-oxide Chemical compound C1=CC=C2S(=O)NN=CC2=C1 REEXLQXWNOSJKO-UHFFFAOYSA-N 0.000 description 1
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical class C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 235000011331 Brassica Nutrition 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 241000132570 Centaurea Species 0.000 description 1
- 244000192528 Chrysanthemum parthenium Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000208296 Datura Species 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- 241000221079 Euphorbia <genus> Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000110847 Kochia Species 0.000 description 1
- 241000520028 Lamium Species 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000011096 Papaver Nutrition 0.000 description 1
- 240000001090 Papaver somniferum Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000219295 Portulaca Species 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 241000207763 Solanum Species 0.000 description 1
- 235000002634 Solanum Nutrition 0.000 description 1
- 241000606270 Valerianella Species 0.000 description 1
- DNWKZHXTBHCPFN-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] carbonochloridate Chemical compound COC(=O)NC1=CC=CC(OC(Cl)=O)=C1 DNWKZHXTBHCPFN-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
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- BUSBFZWLPXDYIC-UHFFFAOYSA-N arsonic acid Chemical class O[AsH](O)=O BUSBFZWLPXDYIC-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 150000005130 benzoxazines 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
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 150000002460 imidazoles 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
- 150000002576 ketones Chemical class 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
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 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
- 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
- 150000007530 organic bases Chemical group 0.000 description 1
- DTHHUAXKOMWYBI-UHFFFAOYSA-N oxadiazolidine Chemical class C1CONN1 DTHHUAXKOMWYBI-UHFFFAOYSA-N 0.000 description 1
- YDCVQGAUCOROHB-UHFFFAOYSA-N oxadiazolidine-4,5-dione Chemical class O=C1NNOC1=O YDCVQGAUCOROHB-UHFFFAOYSA-N 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000005299 pyridinones Chemical class 0.000 description 1
- 150000008318 pyrimidones Chemical class 0.000 description 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical class OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 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
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 150000003582 thiophosphoric acids Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 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)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
(54) - Selektivní 4ierbicí<ní -prostředek a způsob výroby jeho účinné látky(54) - Selective agent and process for the manufacture of an active ingredient thereof
Vynález -se - týká . . (B-metho-xy-karbonylami·nojfenylesteru - -kyseliny - N-ethylkarbanilové, způsobu - výroby- -této· - -sloučeniny, - stejně . jako selektivního - -herbicidního . -prostředku, - obsahujícího - tuto sloučeninu, --zvláště - --pro - potlačování -.plevelů - - v - kulturách bavlny podzemnice olejné -a rýže.The invention relates. . (N-ethylcarbanilic acid (B-methoxy-carbonylamino) -phenyl] -phenylester), a process for the preparation of this compound, as well as a selective herbicide-containing composition, especially - - for - suppressing - weed - - in - cotton crops of peanuts -and rice.
Deriváty - kyseliny - karbaní lové - - -se -selektivní - herbicidním - účinkem jsou - již - známé - (patentový spis NSR č. 1 567151). Účinné .látky tohoto druhu - známé - v praxi, - totiž - - methyl-N-(3-[ (Bmethylfenyl·)karbarnoyloxуJfenyl-Jkarbamát (Phenmedipham), - - mají - vynikající -selektivitu - proti řepě buráku, .mají však kromě toho jen úzké spektrum - účinku.Derivatives - carbonic acids - - with - a selective - herbicidal action - are already known (German Patent No. 1 567151). Effective compounds of this kind - known in practice, namely - methyl N- (3 - [(Bmethylphenyl) carbamoyloxy] phenylcarbamate (Phenmedipham), - have an excellent selectivity against peanut beet, but have in addition to only a narrow spectrum - effect.
Úkolem - tohoto - vynálezu je - - vyvinout selektivní - herbicidní - . prostředek, - který má - široké - spektrum účinku a může se 'použít v jiných zemědělských -kulturách, -jako -je bavlna, .podzemnice olejná a- . rýže.The object of the present invention is to develop selective herbicidal herbicides. a composition which has a broad spectrum of action and can be used in other agricultural cultures such as cotton, groundnuts and peanuts. rice.
Tento - úkol - podle vynálezu - řeší prostředek, který se - vyznačuje - tím, že jako - účinnou látku -obsahuje (3methoxykm±onylamino)fenylester - kyseliny - N^ethyl-karbanilové - - vzorce /CÍH5·This object - according to the invention - is solved by a composition which is characterized in that it contains - (3-methoxycyclohexylamino) -phenyl ester - N 4 -ethylcarbanilic acid - of the formula ( C 5 H 5) as an active substance
0-CO-NO-CO-N
Jeho herbicidní - účinek se týká, mnohMruhů rostlin, jako je například' - Valerianella, Portulaca, Papaver, Kochia, Solanum, --Escholtzia, Euphorbia, Brassica, -Datura,--ípomea, Setaria, Echinochloa, Dijgitaria, - Steílaria, - -Senecio, Matricaria, - Lamium, Centaurea, - , -Amaranthus a Polygonům.Its herbicidal effect relates to many species of plants, such as Valerianella, Portulaca, Papaver, Kochia, Solanum, Escholtzia, Euphorbia, Brassica, Datura, Setpea, Setaria, Echinochloa, Dijgitaria, Steilaria, -Senecio, Matricaria, - Lamium, Centaurea, -, -Amaranthus and Polygons.
Používané množství pro- - - selektivní - potlačování - ..plevele . - .činí . - asi 0,5 - ..až. - . 5 - kg účinné látky .na.-hektar. · ; ·The amount used is - - selective - suppressing -. -. about 0.5 to about. -. 5 kg of active substance per hectare. · ; ·
Sloučeninu podle vynálezu - lze - v protikladu ke známým účinným látkám analogické struktury, v uvedeném množství s - překvapením - používat místo· -v - řepě v jiných -kulturách, jako je bavlna, podzemnice Olejná, - rýže a podobně, aniž by se způsobilo Jejich poškození, což má velký - hospodářský - - význam.The compound according to the invention - in contrast to known active substances of analogous structure, in the indicated amounts - surprisingly - can be used instead of in beets in other cultures such as cotton, peanuts, rice and the like without causing Their damage, which is of great - economic - importance.
Sloučenina podle. - vynálezu - se .může - používat - buď - samotná - nebo s -jinými - účinnými látkami.Compound of. The invention can be used either alone or with other active substances.
Vždy podle požadovaného účelu používají se jako složky ve směsi například - následující - herbicidně účinné látky, které - se .popřípadě mohou přidávat teprve bezprostředně před - použitím . sloučeniny - podle - vynálezu: substituované aniliny, kyseliny - aryloxykarboxylové, - stejně jako jejich soli estery a amidy, ethery, kyseliny arsonové, stejně jako jejich soli, estery. a amidy, benzimiďazoly, benzisothiazoly, benzthiadiazinondioxidy, benzoxaziny, benzoxazinony, benzthiazoly, benzthiadiazoly, biurety, chinoliny, karbamáty, alifatické karboxylové kyseliny, stejně jako jejich soli, estery a amidy, aromatické karboxylové kyseliny, stejně jako jejich soli, estery a amidy, karbamoylalkyl-thio-dithiofosfáty, chinazoliny, kyseliny cykloaklylamidokarbonthiolové, stejně jako jejich soli, estery a amidy, cykloalkylkarbonamido-thiazoly, substituované kyseliny dikarboxylové, stejně jako , je'jich-soli, estery a, amidy, dihydrobenzofuranylsulfonáty, disulfidy, dipyridyliové .· soli, dithiokarbámáty, kyseliny dithiofosforečné, stejně jako jejich soli, estery a amidy, močoviny, ’ hexahydro-lH-karbothioáty, hydantoiny, hydrazidy, , hydrazoniové soli, isoxazolpyrimidoný, imidazoly, isothiazolpyrimidony, ketony, , naftolchfnony, alifatické .nitřily, aromatické' nitrily, oχadiizblý, .Depending on the desired purpose, for example, the following herbicidally active substances are used as components in the mixture, which, if necessary, can only be added immediately before use. compounds of the invention: substituted anilines, aryloxycarboxylic acids, - as well as their salts, esters and amides, ethers, arsonic acids, as well as their salts, esters. and amides, benzimidazoles, benzisothiazoles, benzthiadiazinone dioxides, benzoxazines, benzoxazinones, benzthiazoles, benzthiadiazoles, biurets, quinolines, carbamates, aliphatic carboxylic acids as well as their salts, esters and amides, aromatic carboxylic acids as well as their salts, esters and amides, thio-dithiophosphates, quinazolines, cycloaclylamidocarbonthiolic acids, as well as their salts, esters and amides, cycloalkylcarbonamido-thiazoles, substituted dicarboxylic acids, as well as their salts, esters and amides, dihydrobenzofuranyl sulfonates, disulfides, disulfides, dipyrides. dithiocarbamates, dithiophosphoric acids, as well as their salts, esters and amides, ureas, hexahydro-1H-carbothioates, hydantoins, hydrazides, hydrazonium salts, isoxazolpyrimidone, imidazoles, isothiazolpyrimidones, ketones, aromatic, naphtholilyls, naphtholilyls. oχadiizblý,.
oxadiažinóhýi* oxadiazohdindiony, O'xadiazíhal·ohý, fenoly, stejně ' jako jejich soli .a estery, kyseliny fosfonové', -. Stejně jako jejich soli, estery a ' amidy, piperidiny, pyrazoly, kyseliny ' pyrazolalkylkarboxylové, stejně jako jejich soli, ' estery a amidy, pýražoliové soli, pyrazoliumalkylsulfáty, pyridaziny, substituované . pyridazony, kyseliny pyridinkarboxylové, stejně jako jejich soli, estery a amidy, pyridiny, ...The oxadiazolidinediones, the oxadiazolidines, the phenols as well as their salts and the phosphonic acid esters. As well as their salts, esters and amides, piperidines, pyrazoles, pyrazolylcarboxylic acids, as well as their salts, esters and amides, pyrazolium salts, pyrazolium alkyl sulfates, pyridazines, substituted. pyridazones, pyridinecarboxylic acids, as well as their salts, esters and amides, pyridines, ...
pyridihkaгboxýláty, pyridinony, pyrim^dony, kyseliny pyrrolidinkarboxylové, stejně jako jejich soli, estery a amidy, pyrrolidiny, kyseliny arylsulfonové, stejně jako' jejich soli, estery a amidy, styroly, tetrahydrDoxadiazindiony, tetrahydromethanoindeny, tetrahydro-diažoi-thiohy, tetrahydro-thiadiažm-thiorlý, tetrahydro,thiadiažoldioný, thiadiazoly, amidy aromatických thiokarboxylových kyselin, kyseliny thiokarboxylové, stejně jako jejich soli, estery a amidy, thiolkarbamáty, kyseliny thiofosforečné, stejně jako , jejich soli, estery a amidy, dziny, trlazoly, uráčily a uretidindiony.pyridinocarboxylates, pyridinones, pyrimidones, pyrrolidinecarboxylic acids, as well as their salts, esters and amides, pyrrolidines, arylsulfonic acids, as well as their salts, esters and amides, styrols, tetrahydrodoxadiazinediones, tetrahydromethanoindenes, tetrahydro-diisothioates, tetrahydro-tetrahydro-thiadiazoles, tetrahydro thio, tetrahydro , thiadiazole, thiadiazoles, aromatic thiocarboxylic acid amides, thiocarboxylic acids, as well as their salts, esters and amides, thiolcarbamates, thiophosphoric acids, as well as their salts, esters and amides, dzines, trlazoles, uracils and uretidinediones.
Kromě toho se mohou používat také ' jiné přísady, například takové, které nejsou fytotoxické, které poskytují herbicidům synergický , vzestup účinku, jako jsou například smáčedla, emulgátory,' rozpouštědla a olejovité přísady.In addition, other additives, for example those which are not phytotoxic, can be used which give the herbicides a synergistic increase in action, such as wetting agents, emulsifiers, solvents and oily additives.
Účelně se, sloučenina podle vynálezu nebo její směs s jinými herbicidně účinnými látkami používá ve formě přípravků, jako prášků, poprašů, granulátů, roztoků, 'emulzí nebo suspenzí, za přídavku tekutých a/nebo pevných nosičů nebo zřeďovadel a popřípaci smáčedel, prostředku podporujícího ulpívání, emulgačního a/nebo dispergačního prostředku.Suitably, the compound of the invention or a mixture thereof with other herbicidally active substances is used in the form of preparations such as powders, dusts, granules, solutions, emulsions or suspensions, with the addition of liquid and / or solid carriers or diluents and wetting agents, adhering agents an emulsifying and / or dispersing agent.
Vhodné kapalné nosiče jsou například voda, alifatické a aromatické uhlovodíky, jako benzen, toluen, ' xylen, cyklohexanon, ' isoforon, dlmethylsulfokid, dimethylformamid a dále frakce z destilace minerálních olejů.Suitable liquid carriers are, for example, water, aliphatic and aromatic hydrocarbons such as benzene, toluene, xylene, cyclohexanone, isophorone, dlmethylsulfokide, dimethylformamide and the fractions from the distillation of mineral oils.
Jako pevné nosiče se hodí minerální hlinky, například tonsil, si.likagel, mastek, kaolin, attaclay, vápenec, kyselina , křemičitá a rostlinné produkty, například' moučky.Suitable solid carriers are mineral clays such as tonsil, silica, talc, kaolin, attaclay, limestone, acid, silicas, and plant products such as flours.
Jako povrchově , aktivní látky se například uvádějí ligninsulfonát vápenatý, polyoxyethylehalkylfehyiether, kyseliny naftalensulfonové a jejich soli, kyseliny fenolsulfonové a jejich soli, formaldehydové kondenzáty, sulfáty vyšších, alifatických alkoholů, stejně jako substituované kyseliny benzensulfonové a jejich soli.Surfactants include, for example, calcium ligninsulfonate, polyoxyethylene alkyl alkyl ether, naphthalenesulfonic acids and their salts, phenolsulfonic acids and their salts, formaldehyde condensates, sulfates of higher, aliphatic alcohols, as well as substituted benzenesulfonic acids and their salts.
Podíl účinné látky, popřípadě účinných látek v různých přípravcích, se může měnit v širokých hranicích. Prostředky obsahují například asi 10 až 80 % hmotnostních účinné látky, asi 90 až 20 % hmotnostních kapalného nebo pevného nosiče, stejně jako popřípadě až 20 % hmotnostních povrchově aktivních látek.The proportion of active compound (s) in the various preparations can vary within wide limits. The compositions contain, for example, about 10 to 80% by weight of active ingredient, about 90 to 20% by weight of a liquid or solid carrier, as well as optionally up to 20% by weight of surfactants.
Postřik prostředkem se může provádět obvyklým způsobem, například s vodou jako nosičem při množství postřikové břečky asiThe spraying of the composition can be carried out in a conventional manner, for example with water as the carrier at a spray rate of about
100 až 1000 litrů na hektar. Použití prostředku v tak zvaných „maloobjemových” a „ultramaloobjemových” postupech je rov207787 něž možné, stejně jako jejich aplikace ve formě tak zvaných mikrogranulátů.100 to 1000 liters per hectare. The use of the composition in so-called "small-volume" and "ultra-small-volume" processes is also possible, as is their application in the form of so-called microgranules.
Sloučenina, která až dosud není známá z literatury, se způsobem podle vynálezu vyrobí tak, že se methylester kyseliny 3-hydroxykarbanilové vzorce IIA compound not previously known in the literature is prepared by the process according to the invention by the preparation of 3-hydroxycarbanilic acid methyl ester of the formula II
OHOH
NH-COOCh (II) nechá reagovat v přítomnosti terciární organické báze, jako například triethylaminu nebo pyridinu, nebo jako alkalická sůl s N-ethyl-N-fenylkarbamoylch.loridem vzorce IIINH-COOCh (II) is reacted in the presence of a tertiary organic base such as triethylamine or pyridine, or as an alkali salt with N-ethyl-N-phenylcarbamoyl chloride of formula III
N-C0-C1, (lil)N-C0-C1, (III)
při teplotě 0 až 100°C na požadovaný produkt a ten se potom obvyklým způsobem izoluje.at a temperature of 0 to 100 ° C to the desired product, which is then isolated in the usual manner.
Následující příklady objasňují možnosti výroby sloučeniny podle vynálezu. Tyto příklady však žádným způsobem vynález neomezují.The following examples illustrate the possibilities of making the compound of the invention. However, these examples do not limit the invention in any way.
Příklad 1Example 1
Roztok 18,2 g (0,15 mol) . N-ethylanilinu v 50 ml ethylesteru kyseliny octové se smíchá s 50 ml vody. Za míchání se potom přikape roztok 34,4 g (0,15 mol) 3-methoxykarbonylaminofenylesteru kyseliny chlormravenčí ve 100 ml ethylesteru kyseliny octové a současně roztok 20,7 g (0,15 mol) uhličitanu draselného v 70 ml vody, přičemž se teplota udržuje chlazením na 10 až 15 '°C. Směs se dále míchá za chlazení ledem 30 minut. Potom se organická fáze oddělí a při teplotě 0 °C promyje zředěnou kyselinou chlorovodíkovou a vodou. Po vysušení síranem horečnatým se provede odpaření za sníženého tlaku. Olejovitý zbytek krystaluje ze směsi isopropyletheru a pentanu.A solution of 18.2 g (0.15 mol). N-ethylaniline in 50 ml of ethyl acetate was mixed with 50 ml of water. Under stirring, a solution of 34.4 g (0.15 mol) of 3-methoxycarbonylaminophenyl chloroformate in 100 ml of ethyl acetate and a solution of 20.7 g (0.15 mol) of potassium carbonate in 70 ml of water are added dropwise while stirring. maintained by cooling to 10-15 ° C. The mixture was further stirred under ice-cooling for 30 minutes. The organic phase was then separated and washed at 0 ° C with dilute hydrochloric acid and water. After drying over magnesium sulfate, evaporation under reduced pressure is carried out. The oily residue crystallizes from a mixture of isopropyl ether and pentane.
Výtěžek: 36,2 g = 76,8 % teorie.Yield: 36.2 g = 76.8% of theory.
(3-methoxykarbonylamino) fenylester kyseliny N-ethylkarbanilové má teplotu tání 110 až 110,5 °C.N-ethylcarbanilic acid (3-methoxycarbonylamino) phenyl ester has a melting point of 110-110.5 ° C.
Analýza:Analysis:
Vypočteno·: 64,96 % C, 5,77 % H, 8,91 % N;Calculated:% C, 64.96;% H, 5.77;% N, 8.91;
nalezeno: 64,93 % C, 6,08 % H, 9,08 % N.Found:% C, 64.93;% H, 6.08;% N, 9.08.
Příklad 2Example 2
Sodná sůl vyrobená z 16,7 g (0,1 mol) methylesteru kyseliny 3-hydroxykarbanilové a methoxidu sodného (vyrobeného z 2,3 g sodíku) v absolutním methanolu, se po důkladném -odstranění methanolu ve vakuu suspenduje ve 100 ml suchého methylisobutylketonu. Za míchání se přikape roztok 18,4 g (0,1 mol) N-ethyl-N-fenylkarbamoylchloridu v asi 80 ml - methylisobutylketonu, přičemž teplota vystoupí asi na 30 °C. Směs se potom dále míchá jednu hodinu při . 70 °C. Po ochlazení na teplotu místnosti se přidá asi 200 ml ethylesteru kyseliny octové a při 0 °C se promyje zředěným roztokem hydroxidu sodného a vodou, vysuší síranem hořečnatým a za sníženého tlaku odpaří. Olejovitý zbytek se krystaluje ze směsi isopropyletheru a pentanu.The sodium salt produced from 16.7 g (0.1 mol) of 3-hydroxycarbanilic acid methyl ester and sodium methoxide (made from 2.3 g of sodium) in absolute methanol is suspended in 100 ml of dry methylisobutyl ketone after thorough removal of the methanol under vacuum. While stirring, a solution of 18.4 g (0.1 mol) of N-ethyl-N-phenylcarbamoyl chloride in about 80 ml of methyl isobutyl ketone is added dropwise, the temperature rising to about 30 ° C. The mixture was then further stirred at room temperature for 1 hour. 70 ° C. After cooling to room temperature, about 200 ml of ethyl acetate were added and washed at 0 ° C with dilute sodium hydroxide solution and water, dried over magnesium sulfate and evaporated under reduced pressure. The oily residue was crystallized from a mixture of isopropyl ether and pentane.
Výtěžek: 27,3 g — 87 % teorie.Yield: 27.3 g - 87% of theory.
(3-methoxykarbonylamino )f enylester kyseliny N-ethylkarbanilové má teplotu tání 110 až 110,5 °C.N-ethylcarbanilic acid (3-methoxycarbonylamino) phenyl ester has a melting point of 110-110.5 ° C.
Příklad 3Example 3
a) 46,0 g (0,16 mol) [3-niirofenyl]esteru kyseliny N-ethylkarbanilové se hydrogenuje ve 400 ml tetrahydrofuranu na 5 g Raneyova niklu při 20 až 25 °C. Po odfiltrování Raneyova niklu se provede odpaření za sníženého tlaku a zbytek se rekrystaluje ze směsi ethylesteru kyseliny octové a pentanu.a) 46.0 g (0.16 mol) of N-ethylcarbanilic acid [3-nitro-phenyl] ester are hydrogenated in 400 ml of tetrahydrofuran to 5 g of Raney nickel at 20-25 ° C. After Raney nickel is filtered off, evaporation under reduced pressure is carried out and the residue is recrystallized from a mixture of ethyl acetate and pentane.
Výtěžek: 25,4 g — 62 % teorie.Yield: 25.4 g - 62% of theory.
(3-amino-f eny i Jester kyseliny N-ethylkarbanilové má teplotu tání 68 až 70 °C.(3-Aminophenyl) N-ethylcarbanilic acid ester has a melting point of 68-70 ° C.
b) 25 g (0,0975 mol) (3-ammofenyl)esteru kyseliny N-ethylkarbanilové se rozpustí v malém množství ethylesteru kyseliny octové. Po přidání 20 ml vody a 4,0 g (0,1 mol) kysličníku horečnatého se za míchání a chlazení na 10 až 15 °C přikape 9,2 g (0,0975 mol) methylesteru kyseliny chlormravenčí. Dále -se míchá 30 minut při 15 °C, potom se organická fáze oddělí, promyje zředěnou kyselinou chlorovodíkovou a vodou a po vysušení síranem hořečnatým odpaří za sníženého tlaku. . Olejovitý zbytek se krystaluje ze směsi isopropyletheru a pentanu.b) 25 g (0.0975 mol) of N-ethylcarbanilic acid (3-aminophenyl) ester are dissolved in a small amount of ethyl acetate. After addition of 20 ml of water and 4.0 g (0.1 mol) of magnesium oxide, 9.2 g (0.0975 mol) of methyl chloroformate were added dropwise with stirring and cooling to 10-15 ° C. It is stirred for 30 minutes at 15 [deg.] C., then the organic phase is separated off, washed with dilute hydrochloric acid and water and, after drying over magnesium sulphate, evaporated under reduced pressure. . The oily residue was crystallized from a mixture of isopropyl ether and pentane.
Výtěžek: 27,9 g = 91 % teorie.Yield: 27.9 g = 91% of theory.
(3-methoxykarbonylamino) fenylester kyseliny N-ethylkarbanilové má teplotu tání 110 až 110,5 °C.N-ethylcarbanilic acid (3-methoxycarbonylamino) phenyl ester has a melting point of 110-110.5 ° C.
Sloučenina podle vynálezu je rozpustná v acetonu, cyklohexanu, methylenchloridu, ethylesteru kyseliny octové a dimethylformamidu. Tato sloučenina je nerozpustná ve vodě a benzínu.The compound of the invention is soluble in acetone, cyclohexane, methylene chloride, ethyl acetate and dimethylformamide. This compound is insoluble in water and gasoline.
Následující příklad slouží к objasnění možnosti použití sloučeniny podle vynálezu.The following example serves to illustrate the possibility of using the compound of the invention.
Příklad 4Example 4
Rostliny uvedené dále se ošetří ve skleníku postemergentním postupem za použití 1 kg účinné látky na hektar. Jako srovnávací prostředek slouží Phenmedipham. Rostliny jsou ve stadiu počátečního růstu. Aplikované množství tekutiny odpovídá 500 litrům na hektar a prostředek se pooužívá ve formě vodné emulze. Po 14 dnech se ohodnotí výsledek ošetření.The plants listed below are treated in a greenhouse by a post-emergence procedure using 1 kg of active ingredient per hectare. Phenmedipham is used as a reference. The plants are in the initial growth stage. The amount of liquid applied is 500 liters per hectare and the composition is used in the form of an aqueous emulsion. After 14 days, the treatment result is evaluated.
= úplné zničení = bez poškození= complete destruction = no damage
Jak je z tabulky zřejmé, dosáhlo se u sloučeniny podle vynálezu při dobré snášenlivosti pro kulturní rostliny dobrého účinku na potírání plevele, zatímco srovnávací prostředek při menším účinku kulturní rostliny silně poškodil.As can be seen from the table, the compound of the present invention has a good weed control effect with good crop plant tolerance, while the comparative composition has severely damaged the crop plant with less effect.
TabulkaTable
0^2 ω0 ^ 2 ω
Й ω 4=5 со α> 4-» χ β 2 g ο £ 5 £ СГ β β о о д Cti Й β ф Х>.4 ω 4 = 5 со α> 4- »χ β 2 g ο £ 5 £ Г о β о о д ti ti β ф.>.
d ω £ СО β >ч вd ω £ СО β> ч в
ΛίΛί
Φ «Η 4-» ω ΟΦ «Η 4-» ω Ο
C-4C-4
I ω в xti ,β β ~ > Ο ř-i ω а cti 21 р4 Ο S ω β § Д CU в φ >ί-4 4-» φ >ωI ω in xti, β β ~> Ο ø-i ω and 21 р4 Ο S ω β § C CU in φ> ί-4 4- »φ> ω
Ο Φ ДΦ Φ Д
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2819748A DE2819748C2 (en) | 1978-05-02 | 1978-05-02 | N-Ethylcarbanilic acid (3-methoxycarbonylamino) phenyl ester, a process for the preparation of this compound and a selective herbicidal agent containing it |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS207787B2 true CS207787B2 (en) | 1981-08-31 |
Family
ID=6038754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS792753A CS207787B2 (en) | 1978-05-02 | 1979-04-20 | Selective herbicide means and method of making its active substance |
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|---|---|
| JP (1) | JPS54144338A (en) |
| AR (1) | AR222653A1 (en) |
| AT (1) | AT365895B (en) |
| AU (1) | AU522366B2 (en) |
| BE (1) | BE875991A (en) |
| BR (1) | BR7902627A (en) |
| CA (1) | CA1108639A (en) |
| CH (1) | CH639946A5 (en) |
| CS (1) | CS207787B2 (en) |
| DD (1) | DD143200A5 (en) |
| DE (1) | DE2819748C2 (en) |
| EG (1) | EG13834A (en) |
| ES (1) | ES478923A1 (en) |
| FI (1) | FI790909A7 (en) |
| FR (1) | FR2424905A1 (en) |
| GB (1) | GB2020283B (en) |
| GR (1) | GR73571B (en) |
| HU (1) | HU184202B (en) |
| IL (1) | IL57073A (en) |
| IN (1) | IN150828B (en) |
| IT (1) | IT1166730B (en) |
| MX (1) | MX5787E (en) |
| NL (1) | NL7901680A (en) |
| PH (1) | PH14259A (en) |
| PL (1) | PL116642B1 (en) |
| PT (1) | PT69398A (en) |
| RO (3) | RO78022A (en) |
| SE (1) | SE7902441L (en) |
| SU (1) | SU852167A3 (en) |
| TR (1) | TR20603A (en) |
| YU (1) | YU40364B (en) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1567151C3 (en) * | 1965-04-09 | 1974-02-21 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Diurethanes, processes for the preparation of these compounds and herbicidal compositions containing them |
| US3535101A (en) * | 1966-09-07 | 1970-10-20 | Schering Ag | Herbicide and algicide means |
| US3901936A (en) * | 1966-10-15 | 1975-08-26 | Schering Ag | Process for the preparation of n-carbamoyloxyphenyl carbamates |
| JPS5140073A (en) * | 1974-06-28 | 1976-04-03 | Siemens Ag | |
| DE2557552C2 (en) * | 1975-12-18 | 1984-12-20 | Schering AG, 1000 Berlin und 4709 Bergkamen | Diurethanes and herbicidal agents containing these compounds as active ingredients |
-
1978
- 1978-05-02 DE DE2819748A patent/DE2819748C2/en not_active Expired
-
1979
- 1979-03-02 NL NL7901680A patent/NL7901680A/en not_active Application Discontinuation
- 1979-03-16 FI FI790909A patent/FI790909A7/en not_active Application Discontinuation
- 1979-03-19 SE SE7902441A patent/SE7902441L/en unknown
- 1979-03-19 YU YU667/79A patent/YU40364B/en unknown
- 1979-03-23 ES ES478923A patent/ES478923A1/en not_active Expired
- 1979-03-27 PT PT69398A patent/PT69398A/en unknown
- 1979-03-29 IN IN208/DEL/79A patent/IN150828B/en unknown
- 1979-04-06 IT IT21636/79A patent/IT1166730B/en active
- 1979-04-07 GR GR58833A patent/GR73571B/el unknown
- 1979-04-15 IL IL7957073A patent/IL57073A/en unknown
- 1979-04-18 AR AR276229A patent/AR222653A1/en active
- 1979-04-20 CS CS792753A patent/CS207787B2/en unknown
- 1979-04-23 GB GB7914092A patent/GB2020283B/en not_active Expired
- 1979-04-25 DD DD79212488A patent/DD143200A5/en unknown
- 1979-04-25 CA CA326,275A patent/CA1108639A/en not_active Expired
- 1979-04-26 MX MX797937U patent/MX5787E/en unknown
- 1979-04-27 HU HU79SCHE677A patent/HU184202B/en unknown
- 1979-04-27 SU SU792757223A patent/SU852167A3/en active
- 1979-04-30 BR BR7902627A patent/BR7902627A/en unknown
- 1979-04-30 PL PL1979215274A patent/PL116642B1/en unknown
- 1979-04-30 TR TR20603A patent/TR20603A/en unknown
- 1979-04-30 CH CH405879A patent/CH639946A5/en not_active IP Right Cessation
- 1979-04-30 RO RO7987405A patent/RO78022A/en unknown
- 1979-04-30 AT AT0323279A patent/AT365895B/en not_active IP Right Cessation
- 1979-04-30 PH PH22442A patent/PH14259A/en unknown
- 1979-04-30 RO RO79104234A patent/RO80177A/en unknown
- 1979-05-01 AU AU46578/79A patent/AU522366B2/en not_active Ceased
- 1979-05-01 JP JP5256679A patent/JPS54144338A/en active Pending
- 1979-05-02 BE BE0/194952A patent/BE875991A/en not_active IP Right Cessation
- 1979-05-02 EG EG254/79A patent/EG13834A/en active
- 1979-05-02 FR FR7911009A patent/FR2424905A1/en active Granted
- 1979-05-30 RO RO79104223A patent/RO80176A/en unknown
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