CH500173A - Verfahren zur Herstellung neuer 4-Dimethylaminomethylphenyl-N-methylcarbamate - Google Patents
Verfahren zur Herstellung neuer 4-Dimethylaminomethylphenyl-N-methylcarbamateInfo
- Publication number
- CH500173A CH500173A CH1881466A CH1881466A CH500173A CH 500173 A CH500173 A CH 500173A CH 1881466 A CH1881466 A CH 1881466A CH 1881466 A CH1881466 A CH 1881466A CH 500173 A CH500173 A CH 500173A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- methyl group
- group
- compound
- isopropyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 3
- VTFGXYKXGGSLIA-UHFFFAOYSA-N [4-[(dimethylamino)methyl]phenyl]-methylcarbamic acid Chemical compound CN(C)CC1=CC=C(C=C1)N(C)C(=O)O VTFGXYKXGGSLIA-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 31
- 238000002360 preparation method Methods 0.000 claims description 14
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 241000607479 Yersinia pestis Species 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 11
- -1 dimethylaminomethyl compound Chemical class 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- 239000013543 active substance Substances 0.000 description 9
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- 241001425390 Aphis fabae Species 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- YVLHTQPPMZOCOW-UHFFFAOYSA-N 2-methoxy-1-methyl-4-propan-2-ylbenzene Chemical compound COC1=CC(C(C)C)=CC=C1C YVLHTQPPMZOCOW-UHFFFAOYSA-N 0.000 description 4
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- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- 241000255969 Pieris brassicae Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 241000344246 Tetranychus cinnabarinus Species 0.000 description 4
- LSQXNMXDFRRDSJ-UHFFFAOYSA-N Thymol methyl ether Chemical compound COC1=CC(C)=CC=C1C(C)C LSQXNMXDFRRDSJ-UHFFFAOYSA-N 0.000 description 4
- 239000012876 carrier material Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 235000013601 eggs Nutrition 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- OQYJXFQUMXHNPS-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-5-methyl-2-propan-2-ylphenol Chemical compound C(C)(C)C1=C(C=C(C(=C1)CN(C)C)C)O OQYJXFQUMXHNPS-UHFFFAOYSA-N 0.000 description 3
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- 241000982105 Brevicoryne brassicae Species 0.000 description 3
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- VKEQBMCRQDSRET-UHFFFAOYSA-N Methylone Chemical compound CNC(C)C(=O)C1=CC=C2OCOC2=C1 VKEQBMCRQDSRET-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VWNWEVJFINUGTJ-UHFFFAOYSA-N [4-[(dimethylamino)methyl]-2,3-dimethylphenyl]-methylcarbamic acid Chemical compound CC1=C(CN(C)C)C=CC(N(C)C(O)=O)=C1C VWNWEVJFINUGTJ-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
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- KZHCBDBQNUDDIY-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-2,3-dimethylphenol Chemical compound CC1=C(C=CC(=C1C)CN(C)C)O KZHCBDBQNUDDIY-UHFFFAOYSA-N 0.000 description 2
- UXJAGSSVZDVPFB-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-2,5-dimethylphenol Chemical compound CN(C)CC1=CC(C)=C(O)C=C1C UXJAGSSVZDVPFB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- 241000258915 Leptinotarsa Species 0.000 description 2
- 241000171293 Megoura viciae Species 0.000 description 2
- 241000721621 Myzus persicae Species 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 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 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- SKLJOIBQVNMDSY-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxy-5-methyl-2-propan-2-ylbenzene Chemical compound COC1=CC(C(C)C)=C(CCl)C=C1C SKLJOIBQVNMDSY-UHFFFAOYSA-N 0.000 description 1
- SMOHZTWJKGTUIA-UHFFFAOYSA-N 1-ethyl-3-methoxy-5-methylbenzene Chemical compound CCC1=CC(C)=CC(OC)=C1 SMOHZTWJKGTUIA-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- WVCOMNRALZFVRQ-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-2-methyl-5-propan-2-ylphenol Chemical compound CN(C)CC1=CC(=C(C=C1C(C)C)O)C WVCOMNRALZFVRQ-UHFFFAOYSA-N 0.000 description 1
- NFVPEIKDMMISQO-UHFFFAOYSA-N 4-[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC=C(O)C=C1 NFVPEIKDMMISQO-UHFFFAOYSA-N 0.000 description 1
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- LDZXMSNMHCFNMR-UHFFFAOYSA-N CC1=C(C=C(C(=C1)CN(C)C)C)OC Chemical compound CC1=C(C=C(C(=C1)CN(C)C)C)OC LDZXMSNMHCFNMR-UHFFFAOYSA-N 0.000 description 1
- TVGRNDBHYNNNJG-UHFFFAOYSA-N CC1=CC(N(C)C(O)=O)=C(C)C(C)=C1CN(C)C Chemical compound CC1=CC(N(C)C(O)=O)=C(C)C(C)=C1CN(C)C TVGRNDBHYNNNJG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241001558857 Eriophyes Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- STECJAGHUSJQJN-USLFZFAMSA-N LSM-4015 Chemical compound C1([C@@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-USLFZFAMSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000721623 Myzus Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000219830 Onobrychis Species 0.000 description 1
- 241000488583 Panonychus ulmi Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000255972 Pieris <butterfly> Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- ZPMZUYQHXBRQPC-UHFFFAOYSA-N [4-[(dimethylamino)methyl]-2-methyl-5-propan-2-ylphenyl]-methylcarbamic acid Chemical compound CC(C)C1=CC(N(C)C(O)=O)=C(C)C=C1CN(C)C ZPMZUYQHXBRQPC-UHFFFAOYSA-N 0.000 description 1
- IPGOXOATGKOJGZ-UHFFFAOYSA-N [4-[(dimethylamino)methyl]-5-methyl-2-propan-2-ylphenyl]-methylcarbamic acid Chemical compound CC(C)C(C=C(CN(C)C)C(C)=C1)=C1N(C)C(O)=O IPGOXOATGKOJGZ-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
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- 150000001555 benzenes Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- HHTWOMMSBMNRKP-UHFFFAOYSA-N carvacrol Natural products CC(=C)C1=CC=C(C)C(O)=C1 HHTWOMMSBMNRKP-UHFFFAOYSA-N 0.000 description 1
- 235000007746 carvacrol Nutrition 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
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- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical group CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
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- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
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- WYXXLXHHWYNKJF-UHFFFAOYSA-N isocarvacrol Natural products CC(C)C1=CC=C(O)C(C)=C1 WYXXLXHHWYNKJF-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
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- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
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- 235000020234 walnut Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6600023A NL6600023A (en]) | 1966-01-04 | 1966-01-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH500173A true CH500173A (de) | 1970-12-15 |
Family
ID=19795372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1881466A CH500173A (de) | 1966-01-04 | 1966-12-30 | Verfahren zur Herstellung neuer 4-Dimethylaminomethylphenyl-N-methylcarbamate |
Country Status (12)
| Country | Link |
|---|---|
| AT (2) | AT286708B (en]) |
| BE (1) | BE692111A (en]) |
| BR (1) | BR6785871D0 (en]) |
| CH (1) | CH500173A (en]) |
| DE (1) | DE1618722B1 (en]) |
| DK (1) | DK119426B (en]) |
| ES (1) | ES335164A1 (en]) |
| FR (1) | FR1507458A (en]) |
| GB (1) | GB1177350A (en]) |
| IL (1) | IL27197A (en]) |
| NL (1) | NL6600023A (en]) |
| SE (1) | SE327976B (en]) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB792035A (en) * | 1956-07-03 | 1958-03-19 | Rohm & Haas | Pesticidal compositions |
-
1966
- 1966-01-04 NL NL6600023A patent/NL6600023A/xx unknown
- 1966-12-30 GB GB58348/66A patent/GB1177350A/en not_active Expired
- 1966-12-30 SE SE17990/66A patent/SE327976B/xx unknown
- 1966-12-30 DK DK679066AA patent/DK119426B/da unknown
- 1966-12-30 CH CH1881466A patent/CH500173A/de not_active IP Right Cessation
-
1967
- 1967-01-01 IL IL27197A patent/IL27197A/en unknown
- 1967-01-02 ES ES335164A patent/ES335164A1/es not_active Expired
- 1967-01-02 AT AT04683/68A patent/AT286708B/de not_active IP Right Cessation
- 1967-01-02 DE DE1967N0029770 patent/DE1618722B1/de active Pending
- 1967-01-02 AT AT2367A patent/AT270670B/de active
- 1967-01-02 BR BR185871/67A patent/BR6785871D0/pt unknown
- 1967-01-03 BE BE692111D patent/BE692111A/xx unknown
- 1967-01-04 FR FR89924A patent/FR1507458A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BR6785871D0 (pt) | 1973-12-27 |
| DK119426B (da) | 1971-01-04 |
| AT286708B (de) | 1970-12-28 |
| ES335164A1 (es) | 1968-10-01 |
| BE692111A (en]) | 1967-07-06 |
| FR1507458A (fr) | 1967-12-29 |
| GB1177350A (en) | 1970-01-07 |
| AT270670B (de) | 1969-05-12 |
| IL27197A (en) | 1970-11-30 |
| DE1618722B1 (de) | 1970-02-19 |
| NL6600023A (en]) | 1967-07-05 |
| SE327976B (en]) | 1970-09-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |