DE1162352B - Verfahren zur Herstellung von Carbaminsaeureestern - Google Patents
Verfahren zur Herstellung von CarbaminsaeureesternInfo
- Publication number
- DE1162352B DE1162352B DEF30015A DEF0030015A DE1162352B DE 1162352 B DE1162352 B DE 1162352B DE F30015 A DEF30015 A DE F30015A DE F0030015 A DEF0030015 A DE F0030015A DE 1162352 B DE1162352 B DE 1162352B
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- solution
- methylmercapto
- added
- mol
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 6
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 title claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims description 4
- -1 chloroformic acid ester Chemical class 0.000 claims description 29
- 241001124076 Aphididae Species 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 150000002989 phenols Chemical class 0.000 claims description 7
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 150000003139 primary aliphatic amines Chemical class 0.000 claims 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 75
- 239000000243 solution Substances 0.000 description 47
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 39
- 238000003756 stirring Methods 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 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 8
- 238000009835 boiling Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- 230000009885 systemic effect Effects 0.000 description 7
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 241001454295 Tetranychidae Species 0.000 description 6
- 241000607479 Yersinia pestis Species 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- QASBCTGZKABPKX-UHFFFAOYSA-N 4-(methylsulfanyl)phenol Chemical compound CSC1=CC=C(O)C=C1 QASBCTGZKABPKX-UHFFFAOYSA-N 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 241000238876 Acari Species 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 241000256113 Culicidae Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- RRNKDNAGYGFQCY-UHFFFAOYSA-N dimethyl(sulfanylcarbonyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)C(S)=O RRNKDNAGYGFQCY-UHFFFAOYSA-N 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LCNLSFRRONIQFX-UHFFFAOYSA-N 3-methylsulfanylphenol Chemical compound CSC1=CC=CC(O)=C1 LCNLSFRRONIQFX-UHFFFAOYSA-N 0.000 description 2
- VKALYYFVKBXHTF-UHFFFAOYSA-N 4-(methylsulfanyl)-m-cresol Chemical compound CSC1=CC=C(O)C=C1C VKALYYFVKBXHTF-UHFFFAOYSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 2
- 241000113402 Miuraea persicae Species 0.000 description 2
- 241000131102 Oryzaephilus Species 0.000 description 2
- 241001674048 Phthiraptera Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- UTZVRFPLSSHYGF-UHFFFAOYSA-N carboxy(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)C(O)=O UTZVRFPLSSHYGF-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- WIFOIWPHENPZMO-UHFFFAOYSA-N (2,5-dichlorophenyl)methyl-methylcarbamic acid Chemical compound CN(CC1=C(C=CC(=C1)Cl)Cl)C(=O)O WIFOIWPHENPZMO-UHFFFAOYSA-N 0.000 description 1
- JJPPEJSVLZELHN-UHFFFAOYSA-N (3-methyl-4-methylsulfanylphenyl) n,n-dimethylcarbamate Chemical compound CSC1=CC=C(OC(=O)N(C)C)C=C1C JJPPEJSVLZELHN-UHFFFAOYSA-N 0.000 description 1
- SLZKSCPVPMUGAP-UHFFFAOYSA-N (3-methyl-4-methylsulfanylphenyl) n-methylcarbamate Chemical compound CNC(=O)OC1=CC=C(SC)C(C)=C1 SLZKSCPVPMUGAP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AFTFKTCSEGUGAV-UHFFFAOYSA-N 1-methylsulfanylnaphthalen-2-ol Chemical compound C1=CC=C2C(SC)=C(O)C=CC2=C1 AFTFKTCSEGUGAV-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
- RZJRZIHTKWZCQI-UHFFFAOYSA-N 2-butan-2-ylsulfanylphenol Chemical compound CCC(C)SC1=CC=CC=C1O RZJRZIHTKWZCQI-UHFFFAOYSA-N 0.000 description 1
- DGLPDVONIWDUPH-UHFFFAOYSA-N 3,5-dimethyl-2-methylsulfanylphenol Chemical compound CSC1=C(C)C=C(C)C=C1O DGLPDVONIWDUPH-UHFFFAOYSA-N 0.000 description 1
- JGFZITGNFAVSKU-UHFFFAOYSA-N 3,5-dimethyl-4-(methylsulfanyl)phenol Chemical compound CSC1=C(C)C=C(O)C=C1C JGFZITGNFAVSKU-UHFFFAOYSA-N 0.000 description 1
- YFQBELWMXKXATM-UHFFFAOYSA-N 3-methyl-4-methylsulfinylphenol Chemical compound CC1=CC(O)=CC=C1S(C)=O YFQBELWMXKXATM-UHFFFAOYSA-N 0.000 description 1
- KGPGKOSHODHUSR-UHFFFAOYSA-N 3-methyl-4-methylsulfonylphenol Chemical compound CC1=CC(O)=CC=C1S(C)(=O)=O KGPGKOSHODHUSR-UHFFFAOYSA-N 0.000 description 1
- ZCQSJUGIZGMDDA-UHFFFAOYSA-N 4-(methylsulfinyl)phenol Chemical compound CS(=O)C1=CC=C(O)C=C1 ZCQSJUGIZGMDDA-UHFFFAOYSA-N 0.000 description 1
- AIPNNWIVRIENTH-UHFFFAOYSA-N 4-methyl-2-methylsulfanylphenol Chemical compound CSC1=CC(C)=CC=C1O AIPNNWIVRIENTH-UHFFFAOYSA-N 0.000 description 1
- GWMWXFGQYATKBA-UHFFFAOYSA-N 4-methyl-2-sulfanylphenol Chemical compound CC1=CC=C(O)C(S)=C1 GWMWXFGQYATKBA-UHFFFAOYSA-N 0.000 description 1
- VDNYBQKPYHBNOP-UHFFFAOYSA-N 4-methylsulfanyl-3-propan-2-ylphenol Chemical compound C(C)(C)C=1C=C(C=CC1SC)O VDNYBQKPYHBNOP-UHFFFAOYSA-N 0.000 description 1
- KECCFSZFXLAGJS-UHFFFAOYSA-N 4-methylsulfonylphenol Chemical compound CS(=O)(=O)C1=CC=C(O)C=C1 KECCFSZFXLAGJS-UHFFFAOYSA-N 0.000 description 1
- 241000457689 Acerophagus maculipennis Species 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000128742 Ascochyta fabae Species 0.000 description 1
- XAQJBBBBJWAPDW-UHFFFAOYSA-N CC(C=C1C)=CC(N(C)C(O)=O)=C1SC Chemical compound CC(C=C1C)=CC(N(C)C(O)=O)=C1SC XAQJBBBBJWAPDW-UHFFFAOYSA-N 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 240000001307 Myosotis scorpioides Species 0.000 description 1
- 241001608567 Phaedon cochleariae Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 241000690748 Piesma Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- MILMVJUVABWPSX-UHFFFAOYSA-N methyl-(4-methylsulfanyl-3-propan-2-ylphenyl)carbamic acid Chemical compound CSC1=CC=C(N(C)C(O)=O)C=C1C(C)C MILMVJUVABWPSX-UHFFFAOYSA-N 0.000 description 1
- NPLRBJDBLDRPPW-UHFFFAOYSA-N methyl-[(4-methylsulfonylphenyl)methyl]carbamothioic S-acid Chemical compound CN(Cc1ccc(cc1)S(C)(=O)=O)C(S)=O NPLRBJDBLDRPPW-UHFFFAOYSA-N 0.000 description 1
- 239000008164 mustard oil Substances 0.000 description 1
- DWLVWMUCHSLGSU-UHFFFAOYSA-M n,n-dimethylcarbamate Chemical compound CN(C)C([O-])=O DWLVWMUCHSLGSU-UHFFFAOYSA-M 0.000 description 1
- PHWISQNXPLXQRU-UHFFFAOYSA-N n,n-dimethylcarbamothioyl chloride Chemical compound CN(C)C(Cl)=S PHWISQNXPLXQRU-UHFFFAOYSA-N 0.000 description 1
- GKBBEEZLBXJNCR-UHFFFAOYSA-N o-phenyl n-methylcarbamothioate Chemical compound CNC(=S)OC1=CC=CC=C1 GKBBEEZLBXJNCR-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/02—Monothiocarbamic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL131470D NL131470C (en)) | 1959-12-05 | ||
| BE597806D BE597806A (en)) | 1959-12-05 | ||
| NL258661D NL258661A (en)) | 1959-12-05 | ||
| DEF30015A DE1162352B (de) | 1959-12-05 | 1959-12-05 | Verfahren zur Herstellung von Carbaminsaeureestern |
| CH1329960A CH389314A (de) | 1959-12-05 | 1960-11-28 | Verwendung von Carbamaten als Schädlingsbekämpfungsmittel |
| BR12467560A BR6024675D0 (pt) | 1959-12-05 | 1960-12-02 | Processo para a producao de carbamatos |
| GB4185160A GB912895A (en) | 1959-12-05 | 1960-12-05 | New substituted carbamates |
| FR845958A FR1275658A (fr) | 1959-12-05 | 1960-12-05 | Procédé de préparation de carbamates |
| US335381A US3313684A (en) | 1959-12-05 | 1964-01-02 | 3, 5-dimethyl-4-methylmercaptophenyl n-methyl carbamate and methods for combating insects |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF30015A DE1162352B (de) | 1959-12-05 | 1959-12-05 | Verfahren zur Herstellung von Carbaminsaeureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1162352B true DE1162352B (de) | 1964-02-06 |
Family
ID=7093564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF30015A Pending DE1162352B (de) | 1959-12-05 | 1959-12-05 | Verfahren zur Herstellung von Carbaminsaeureestern |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE597806A (en)) |
| BR (1) | BR6024675D0 (en)) |
| CH (1) | CH389314A (en)) |
| DE (1) | DE1162352B (en)) |
| GB (1) | GB912895A (en)) |
| NL (2) | NL258661A (en)) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3313684A (en) * | 1959-12-05 | 1967-04-11 | Bayer Ag | 3, 5-dimethyl-4-methylmercaptophenyl n-methyl carbamate and methods for combating insects |
| DE1254617B (de) | 1964-06-27 | 1967-11-23 | Bayer Ag | Verfahren zur Herstellung von N-Methyl-O-phenylcarbaminsaeureestern |
| US6818670B2 (en) | 1999-11-09 | 2004-11-16 | Bayer Aktiengesellschaft | Active ingredient combination having insecticidal and acaricidal characteristics |
| US6900190B2 (en) | 2000-03-28 | 2005-05-31 | Bayer Aktiengesellschaft | Active substance combinations having insecticidal and acaricidal properties |
| DE102007045955A1 (de) | 2007-09-26 | 2009-04-09 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| WO2010083955A2 (de) | 2009-01-23 | 2010-07-29 | Bayer Cropscience Aktiengesellschaft | Verwendung von enaminocarbonylverbindungen zur bekämpfung von durch insekten übertragenen virosen |
| WO2010108616A1 (de) | 2009-03-25 | 2010-09-30 | Bayer Cropscience Ag | Nematizide, insektizide und akarizide wirkstoffkombinationen umfassend pyridylethylbenzamide und insektizide |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3349115A (en) * | 1963-02-19 | 1967-10-24 | Hooker Chemical Corp | Sulfur-containing carbamate insecticides |
| US3349116A (en) * | 1963-02-20 | 1967-10-24 | Hooker Chemical Corp | Ortho hydrocarbyloxy alkenylenephenyl nu-lower alkylcarbamates |
| US3419663A (en) * | 1963-03-04 | 1968-12-31 | Hooker Chemical Corp | Method for the control of insects using thioalkylphenyl carbamates |
| US3331894A (en) * | 1963-03-04 | 1967-07-18 | Hooker Chemical Corp | o-(diloweralkoxythiophosphinylthioalkyl)phenyl n-loweralkyl carbamates |
| DE1248635B (de) * | 1964-07-04 | 1967-08-31 | Farbenfabriken Bayer Aktiengesellschaft, Leverkusen | Verfahren zur Herstellung eines Alkenylmercaptophenyl - N - methyl-carbaminsäureesters |
| DE2258805C3 (de) * | 1972-12-01 | 1981-06-19 | Bayer Ag, 5090 Leverkusen | N-Methyl-O-phenyl-carbaminsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Insekten |
| DE10042736A1 (de) | 2000-08-31 | 2002-03-14 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| US6534220B2 (en) * | 2000-12-29 | 2003-03-18 | 3M Innovative Properties Company | High-boiling electrolyte solvent |
| CN102395271A (zh) | 2009-03-25 | 2012-03-28 | 拜尔农作物科学股份公司 | 具有杀虫和杀螨特性的活性化合物结合物 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1058304B (de) * | 1953-06-09 | 1959-05-27 | Philips Nv | Insektenbekaempfungsmittel |
-
0
- NL NL131470D patent/NL131470C/xx active
- NL NL258661D patent/NL258661A/xx unknown
- BE BE597806D patent/BE597806A/xx unknown
-
1959
- 1959-12-05 DE DEF30015A patent/DE1162352B/de active Pending
-
1960
- 1960-11-28 CH CH1329960A patent/CH389314A/de unknown
- 1960-12-02 BR BR12467560A patent/BR6024675D0/pt unknown
- 1960-12-05 GB GB4185160A patent/GB912895A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1058304B (de) * | 1953-06-09 | 1959-05-27 | Philips Nv | Insektenbekaempfungsmittel |
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3313684A (en) * | 1959-12-05 | 1967-04-11 | Bayer Ag | 3, 5-dimethyl-4-methylmercaptophenyl n-methyl carbamate and methods for combating insects |
| DE1254617B (de) | 1964-06-27 | 1967-11-23 | Bayer Ag | Verfahren zur Herstellung von N-Methyl-O-phenylcarbaminsaeureestern |
| US6818670B2 (en) | 1999-11-09 | 2004-11-16 | Bayer Aktiengesellschaft | Active ingredient combination having insecticidal and acaricidal characteristics |
| US6900190B2 (en) | 2000-03-28 | 2005-05-31 | Bayer Aktiengesellschaft | Active substance combinations having insecticidal and acaricidal properties |
| DE102007045955A1 (de) | 2007-09-26 | 2009-04-09 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| WO2010083955A2 (de) | 2009-01-23 | 2010-07-29 | Bayer Cropscience Aktiengesellschaft | Verwendung von enaminocarbonylverbindungen zur bekämpfung von durch insekten übertragenen virosen |
| EP2227951A1 (de) | 2009-01-23 | 2010-09-15 | Bayer CropScience AG | Verwendung von Enaminocarbonylverbindungen zur Bekämpfung von durch Insekten übertragenen Viren |
| WO2010108616A1 (de) | 2009-03-25 | 2010-09-30 | Bayer Cropscience Ag | Nematizide, insektizide und akarizide wirkstoffkombinationen umfassend pyridylethylbenzamide und insektizide |
| EP2561758A1 (de) | 2009-03-25 | 2013-02-27 | Bayer CropScience AG | Nematizide Wirkstoffkombinationen umfassend Fluopyram und Thiodicarb |
| EP2561755A1 (de) | 2009-03-25 | 2013-02-27 | Bayer CropScience AG | Nematizide Wirkstoffkombinationen umfassend Fluopyram und Mycorrhiza |
| EP2561756A1 (de) | 2009-03-25 | 2013-02-27 | Bayer CropScience AG | Nematizide Wirkstoffkombinationen umfassend Fluopyram und Spirotetramat |
| EP2561757A1 (de) | 2009-03-25 | 2013-02-27 | Bayer CropScience AG | Nematizide Wirkstoffkombinationen umfassend Fluopyram und Ethiprole |
| EP2564699A1 (de) | 2009-03-25 | 2013-03-06 | Bayer CropScience AG | Nematizide Wirkstoffkombinationen umfassend Fluopyram und Metarhizium |
| EP2564703A1 (de) | 2009-03-25 | 2013-03-06 | Bayer CropScience AG | Nematizide Wirkstoffkombinationen umfassend Fluopyram und Rynaxypyr oder Cyazypyr |
| EP2564704A1 (de) | 2009-03-25 | 2013-03-06 | Bayer CropScience AG | Nematizide Wirkstoffkombinationen umfassend Fluopyram und Methiocarb |
| EP2564701A1 (de) | 2009-03-25 | 2013-03-06 | Bayer CropScience AG | Nematizide Wirkstoffkombinationen umfassend Fluopyram und fluensulfone |
| EP2564705A1 (de) | 2009-03-25 | 2013-03-06 | Bayer CropScience AG | Nematizide Wirkstoffkombinationen umfassend Fluopyram und Pasteuria penetrans |
| EP2564702A1 (de) | 2009-03-25 | 2013-03-06 | Bayer CropScience AG | Nematizide Wirkstoffkombinationen umfassend Fluopyram und ein weiterer Wirkstoff |
| EP2564700A1 (de) | 2009-03-25 | 2013-03-06 | Bayer CropScience AG | Nematizide Wirkstoffkombinationen umfassend Fluopyram und Hirsutella |
| EP2564698A1 (de) | 2009-03-25 | 2013-03-06 | Bayer CropScience AG | Nematizide Wirkstoffkombinationen umfassend Fluopyram und Bacillus firmus |
Also Published As
| Publication number | Publication date |
|---|---|
| BE597806A (en)) | |
| NL258661A (en)) | |
| BR6024675D0 (pt) | 1973-06-12 |
| GB912895A (en) | 1962-12-12 |
| NL131470C (en)) | |
| CH389314A (de) | 1965-03-15 |
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