CH639946A5 - N-aethylcarbanilsaeure-(3-methoxycarbonylaminophenyl)-ester, verfahren zur herstellung dieser verbindung sowie diese enthaltendes selektives herbizides mittel. - Google Patents

N-aethylcarbanilsaeure-(3-methoxycarbonylaminophenyl)-ester, verfahren zur herstellung dieser verbindung sowie diese enthaltendes selektives herbizides mittel. Download PDF

Info

Publication number: CH639946A5
Authority: CH; Switzerland
Prior art keywords: acid; ester; formula; methoxycarbonylaminophenyl; compound
Prior art date: 1978-05-02

Application number

CH405879A

Other languages

German (de)

English (en)

Inventor

Friedrich Dr Arndt

Gerhard Dr Boroschewski

Original Assignee

Schering Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-05-02

Filing date

1979-04-30

Publication date

1983-12-15

1979-04-30 Application filed by Schering Ag filed Critical Schering Ag

1983-12-15 Publication of CH639946A5 publication Critical patent/CH639946A5/de

Links

150000002148 esters Chemical class 0.000 title claims description 22
-1 3-METHOXYCARBONYLAMINOPHENYL Chemical class 0.000 title claims description 18
239000002253 acid Substances 0.000 title claims description 12
150000001875 compounds Chemical class 0.000 title claims description 12
230000002363 herbicidal effect Effects 0.000 title claims description 8
238000004519 manufacturing process Methods 0.000 title 1
238000000034 method Methods 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 8
OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
150000007530 organic bases Chemical group 0.000 claims description 4
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 claims description 3
DNWKZHXTBHCPFN-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] carbonochloridate Chemical compound COC(=O)NC1=CC=CC(OC(Cl)=O)=C1 DNWKZHXTBHCPFN-UHFFFAOYSA-N 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 claims description 3
FFQQCJGNKKIRMD-UHFFFAOYSA-N methyl n-(3-hydroxyphenyl)carbamate Chemical compound COC(=O)NC1=CC=CC(O)=C1 FFQQCJGNKKIRMD-UHFFFAOYSA-N 0.000 claims description 3
150000001447 alkali salts Chemical class 0.000 claims description 2
AAPAVYWERMFERN-UHFFFAOYSA-N ethyl(phenyl)carbamic acid Chemical compound CCN(C(O)=O)C1=CC=CC=C1 AAPAVYWERMFERN-UHFFFAOYSA-N 0.000 claims description 2
239000004009 herbicide Substances 0.000 claims description 2
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
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000004480 active ingredient Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 7
239000003795 chemical substances by application 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
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000000969 carrier Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
235000017060 Arachis glabrata Nutrition 0.000 description 3
244000105624 Arachis hypogaea Species 0.000 description 3
235000010777 Arachis hypogaea Nutrition 0.000 description 3
235000018262 Arachis monticola Nutrition 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
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
244000299507 Gossypium hirsutum Species 0.000 description 3
240000007594 Oryza sativa Species 0.000 description 3
235000007164 Oryza sativa Nutrition 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
239000000654 additive Substances 0.000 description 3
230000006378 damage Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
235000020232 peanut Nutrition 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
235000009566 rice Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
241000335053 Beta vulgaris Species 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
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
239000005594 Phenmedipham Substances 0.000 description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Natural products O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
TWWODOWIDRHPDM-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] n-ethyl-n-phenylcarbamate Chemical class C=1C=CC=CC=1N(CC)C(=O)OC1=CC=CC(NC(=O)OC)=C1 TWWODOWIDRHPDM-UHFFFAOYSA-N 0.000 description 2
244000038559 crop plants Species 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
150000007529 inorganic bases Chemical class 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
CDGCUPPKLDOYGV-UHFFFAOYSA-N n-ethyl-n-phenylcarbamoyl chloride Chemical compound CCN(C(Cl)=O)C1=CC=CC=C1 CDGCUPPKLDOYGV-UHFFFAOYSA-N 0.000 description 2
229910052759 nickel Inorganic materials 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
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
229910000029 sodium carbonate Inorganic materials 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
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
LTQKIFCNCIFEHG-UHFFFAOYSA-N 1,2-oxazole 1H-pyrimidin-2-one Chemical class C=1C=NOC=1.O=C1N=CC=CN1 LTQKIFCNCIFEHG-UHFFFAOYSA-N 0.000 description 1
ZLOTYHZOJPLLGG-UHFFFAOYSA-N 1-sulfanylidenethiadiazinane Chemical compound S=S1CCCNN1 ZLOTYHZOJPLLGG-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
241000219318 Amaranthus Species 0.000 description 1
235000016068 Berberis vulgaris Nutrition 0.000 description 1
235000011331 Brassica Nutrition 0.000 description 1
241000219198 Brassica Species 0.000 description 1
WUFYJSIFTHYAGJ-UHFFFAOYSA-N C=1C=NSC=1.O=C1N=CC=CN1 Chemical class C=1C=NSC=1.O=C1N=CC=CN1 WUFYJSIFTHYAGJ-UHFFFAOYSA-N 0.000 description 1
244000192528 Chrysanthemum parthenium Species 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
229930192627 Naphthoquinone Natural products 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
241000205407 Polygonum Species 0.000 description 1
241000219295 Portulaca Species 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 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
235000002634 Solanum Nutrition 0.000 description 1
241000207763 Solanum Species 0.000 description 1
240000006694 Stellaria media Species 0.000 description 1
241000606270 Valerianella Species 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
125000005037 alkyl phenyl group Chemical group 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
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
150000002019 disulfides Chemical class 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
QQSGDKKFXBGYON-UHFFFAOYSA-N ethoxy-methylperoxy-(6-methyl-2-propan-2-ylpyrimidin-4-yl)oxy-sulfanylidene-$l^{5}-phosphane Chemical class CCOP(=S)(OOC)OC1=CC(C)=NC(C(C)C)=N1 QQSGDKKFXBGYON-UHFFFAOYSA-N 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
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
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
238000002156 mixing Methods 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
150000002791 naphthoquinones Chemical class 0.000 description 1
231100001184 nonphytotoxic Toxicity 0.000 description 1
QNMLMAVEXUCXRG-UHFFFAOYSA-N oxadiazinane-4,5-dione Chemical class O=C1CONNC1=O QNMLMAVEXUCXRG-UHFFFAOYSA-N 0.000 description 1
SDRLFDJOSQLRPB-UHFFFAOYSA-N oxadiazine-4,5-dione Chemical class O=C1CON=NC1=O SDRLFDJOSQLRPB-UHFFFAOYSA-N 0.000 description 1
150000004866 oxadiazoles Chemical class 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
PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
239000000843 powder Substances 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
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 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
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000004094 surface-active agent 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
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
OLPRIZQBWZMBAS-UHFFFAOYSA-N thiadiazolidine 1,1-dioxide Chemical compound O=S1(=O)CCNN1 OLPRIZQBWZMBAS-UHFFFAOYSA-N 0.000 description 1
150000003566 thiocarboxylic acids Chemical class 0.000 description 1
150000003582 thiophosphoric acids Chemical class 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
150000003852 triazoles Chemical class 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)
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)

CH405879A 1978-05-02 1979-04-30 N-aethylcarbanilsaeure-(3-methoxycarbonylaminophenyl)-ester, verfahren zur herstellung dieser verbindung sowie diese enthaltendes selektives herbizides mittel. CH639946A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2819748A DE2819748C2 (de)	1978-05-02	1978-05-02	N-Äthylcarbanilsäure-(3-methoxycarbonylamino)-phenylester, Verfahren zur Herstellung dieser Verbindung sowie diese enthaltendes selektives herbizides Mittel

Publications (1)

Publication Number	Publication Date
CH639946A5 true CH639946A5 (de)	1983-12-15

Family

ID=6038754

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH405879A CH639946A5 (de)	1978-05-02	1979-04-30	N-aethylcarbanilsaeure-(3-methoxycarbonylaminophenyl)-ester, verfahren zur herstellung dieser verbindung sowie diese enthaltendes selektives herbizides mittel.

Country Status (31)

Country	Link
JP (1)	JPS54144338A (ro)
AR (1)	AR222653A1 (ro)
AT (1)	AT365895B (ro)
AU (1)	AU522366B2 (ro)
BE (1)	BE875991A (ro)
BR (1)	BR7902627A (ro)
CA (1)	CA1108639A (ro)
CH (1)	CH639946A5 (ro)
CS (1)	CS207787B2 (ro)
DD (1)	DD143200A5 (ro)
DE (1)	DE2819748C2 (ro)
EG (1)	EG13834A (ro)
ES (1)	ES478923A1 (ro)
FI (1)	FI790909A7 (ro)
FR (1)	FR2424905A1 (ro)
GB (1)	GB2020283B (ro)
GR (1)	GR73571B (ro)
HU (1)	HU184202B (ro)
IL (1)	IL57073A (ro)
IN (1)	IN150828B (ro)
IT (1)	IT1166730B (ro)
MX (1)	MX5787E (ro)
NL (1)	NL7901680A (ro)
PH (1)	PH14259A (ro)
PL (1)	PL116642B1 (ro)
PT (1)	PT69398A (ro)
RO (3)	RO80177A (ro)
SE (1)	SE7902441L (ro)
SU (1)	SU852167A3 (ro)
TR (1)	TR20603A (ro)
YU (1)	YU40364B (ro)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1567151C3 (de) *	1965-04-09	1974-02-21	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Diurethane, Verfahren zur Herstellung dieser Verbindungen sowie diese enthaltende herbizide Mittel
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 (ro) *	1974-06-28	1976-04-03	Siemens Ag
DE2557552C2 (de) *	1975-12-18	1984-12-20	Schering AG, 1000 Berlin und 4709 Bergkamen	Diurethane und herbizide Mittel, enthaltend diese Verbindungen als Wirkstoffe

1978
- 1978-05-02 DE DE2819748A patent/DE2819748C2/de not_active Expired
1979
- 1979-03-02 NL NL7901680A patent/NL7901680A/xx not_active Application Discontinuation
- 1979-03-16 FI FI790909A patent/FI790909A7/fi not_active Application Discontinuation
- 1979-03-19 YU YU667/79A patent/YU40364B/xx unknown
- 1979-03-19 SE SE7902441A patent/SE7902441L/ unknown
- 1979-03-23 ES ES478923A patent/ES478923A1/es not_active Expired
- 1979-03-27 PT PT69398A patent/PT69398A/pt unknown
- 1979-03-29 IN IN208/DEL/79A patent/IN150828B/en unknown
- 1979-04-06 IT IT21636/79A patent/IT1166730B/it active
- 1979-04-07 GR GR58833A patent/GR73571B/el unknown
- 1979-04-15 IL IL7957073A patent/IL57073A/xx unknown
- 1979-04-18 AR AR276229A patent/AR222653A1/es active
- 1979-04-20 CS CS792753A patent/CS207787B2/cs unknown
- 1979-04-23 GB GB7914092A patent/GB2020283B/en not_active Expired
- 1979-04-25 DD DD79212488A patent/DD143200A5/de unknown
- 1979-04-25 CA CA326,275A patent/CA1108639A/en not_active Expired
- 1979-04-26 MX MX797937U patent/MX5787E/es unknown
- 1979-04-27 HU HU79SCHE677A patent/HU184202B/hu unknown
- 1979-04-27 SU SU792757223A patent/SU852167A3/ru active
- 1979-04-30 PH PH22442A patent/PH14259A/en unknown
- 1979-04-30 TR TR20603A patent/TR20603A/xx unknown
- 1979-04-30 CH CH405879A patent/CH639946A5/de not_active IP Right Cessation
- 1979-04-30 AT AT0323279A patent/AT365895B/de not_active IP Right Cessation
- 1979-04-30 BR BR7902627A patent/BR7902627A/pt unknown
- 1979-04-30 RO RO79104234A patent/RO80177A/ro unknown
- 1979-04-30 PL PL1979215274A patent/PL116642B1/pl unknown
- 1979-04-30 RO RO7987405A patent/RO78022A/ro unknown
- 1979-05-01 AU AU46578/79A patent/AU522366B2/en not_active Ceased
- 1979-05-01 JP JP5256679A patent/JPS54144338A/ja active Pending
- 1979-05-02 EG EG254/79A patent/EG13834A/xx active
- 1979-05-02 FR FR7911009A patent/FR2424905A1/fr active Granted
- 1979-05-02 BE BE0/194952A patent/BE875991A/xx not_active IP Right Cessation
- 1979-05-30 RO RO79104223A patent/RO80176A/ro unknown

Also Published As

Publication number	Publication date
DD143200A5 (de)	1980-08-13
BR7902627A (pt)	1979-11-27
TR20603A (tr)	1982-01-01
SE7902441L (sv)	1979-11-03
FR2424905A1 (fr)	1979-11-30
RO78022A (ro)	1982-02-01
RO80177A (ro)	1982-10-26
SU852167A3 (ru)	1981-07-30
EG13834A (en)	1982-06-30
CA1108639A (en)	1981-09-08
RO80176A (ro)	1982-10-26
MX5787E (es)	1984-07-11
PH14259A (en)	1981-04-23
IN150828B (ro)	1982-12-25
PT69398A (de)	1979-04-01
YU40364B (en)	1985-12-31
ATA323279A (de)	1981-07-15
IT1166730B (it)	1987-05-06
IL57073A (en)	1983-07-31
AU4657879A (en)	1979-11-29
GR73571B (ro)	1984-03-19
GB2020283A (en)	1979-11-14
BE875991A (fr)	1979-11-05
AR222653A1 (es)	1981-06-15
PL215274A1 (ro)	1980-02-11
CS207787B2 (en)	1981-08-31
ES478923A1 (es)	1980-01-01
FR2424905B1 (ro)	1984-07-20
HU184202B (en)	1984-07-30
IT7921636A0 (it)	1979-04-06
PL116642B1 (en)	1981-06-30
FI790909A7 (fi)	1979-11-03
AU522366B2 (en)	1982-06-03
JPS54144338A (en)	1979-11-10
DE2819748C2 (de)	1986-07-31
DE2819748A1 (de)	1979-11-15
YU66779A (en)	1983-02-28
GB2020283B (en)	1982-10-27
NL7901680A (nl)	1979-11-06
AT365895B (de)	1982-02-25
IL57073A0 (en)	1979-07-25

Legal Events

Date	Code	Title	Description
1987-12-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE69128804T2 (de)	1998-05-14	Herbizide Carboxamidderivate
DE1567151B2 (de)	1973-07-19	Diurethane, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel
DE2406475C2 (de)	1983-04-28	5-Acetamido-2,4-dimethyltrifluormethansulfonanilid und dessen landwirtschaftlich geeignete Salze, Verfahren zur Herstellung dieser Verbindungen und diese Verbindungen enthaltende Mittel
DE69317439T2 (de)	1998-07-02	Azoxycyanbenzol-Derivate
DE2207549B2 (de)	1979-07-26	1-Aminouracile und deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide
DE2732848A1 (de)	1979-02-08	Diurethane, herbizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung
EP0072528B1 (de)	1986-05-14	(Thio-) Harnstoffe, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Pflanzenschutzmittel
DE2108975B2 (de)	1979-04-19	N-Acyl-Diurethane sowie diese enthaltendes herbizides Mittel
DE1289042B (de)	1969-02-13	Carbamidoxime
DE2624822A1 (de)	1977-12-15	Benzodioxolderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel
DE2341079C2 (de)	1982-05-06	m-Diurethane und selektive herbizide Mittel enthaltend diese Verbindungen als Wirkstoffe
DE2238206C2 (de)	1985-05-02	Azomethine von 4-Amino-5-H-1,2,4-triazin-5-onen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide
CH639946A5 (de)	1983-12-15	N-aethylcarbanilsaeure-(3-methoxycarbonylaminophenyl)-ester, verfahren zur herstellung dieser verbindung sowie diese enthaltendes selektives herbizides mittel.
CH641767A5 (de)	1984-03-15	Carbanilsaeure-(3-(acylamino)-phenyl)-ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes herbizides mittel.
DE2210540A1 (de)	1973-09-06	Cyanphenylcarbonate
DE2650796A1 (de)	1978-05-11	Diurethane, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes selektives herbizides mittel
DE2632692A1 (de)	1977-02-10	Schaedlingsbekaempfungsmittel
DE2320362A1 (de)	1974-11-07	Dichlorthiazolylharnstoffe, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide
DE2310648C3 (de)	1982-05-06	Diurethane, Verfahren zur Herstellung dieser Verbindungen sowie diese enthaltende selektive herbizide Mittel
CH645344A5 (de)	1984-09-28	N-(2-propinyl)-carbanilsaeure-(3-methoxycarbonylaminophenyl)-ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel.
DE2730325A1 (de)	1979-01-11	Carbanilsaeure-(3-ureido-phenyl)- ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel
DE2042110C3 (de)	1979-06-21	Substituierte Phenylthionocarbamate, Verfahren zu ihrer Herstellung und solche Carbamate enthaltende herbizide Mittel
DE2120087A1 (en)	1972-11-09	Selective-herbicidal nitrobenzaldoxime carbamates - - for weed control in root crop culture
DE2644425A1 (de)	1978-04-06	2-(dimethylcarbamoylimino)-benzthiazolin-3-carbonsaeureester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel
DE1670925C3 (ro)	1977-11-03