CH539022A - Verfahren zur Herstellung von Carbamylderivaten substituierter, S-haltiger Alkanal- und Alkanonoxime - Google Patents
Verfahren zur Herstellung von Carbamylderivaten substituierter, S-haltiger Alkanal- und AlkanonoximeInfo
- Publication number
- CH539022A CH539022A CH1249569A CH1249569A CH539022A CH 539022 A CH539022 A CH 539022A CH 1249569 A CH1249569 A CH 1249569A CH 1249569 A CH1249569 A CH 1249569A CH 539022 A CH539022 A CH 539022A
- Authority
- CH
- Switzerland
- Prior art keywords
- formyl
- methyl
- dithiolanoxime
- group
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- 150000002923 oximes Chemical class 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 7
- 230000008569 process Effects 0.000 title claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000012948 isocyanate Substances 0.000 claims description 17
- 150000002513 isocyanates Chemical class 0.000 claims description 13
- 230000001069 nematicidal effect Effects 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 230000000895 acaricidal effect Effects 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000005645 nematicide Substances 0.000 claims description 5
- 239000000642 acaricide Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000002917 insecticide Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000004149 thio group Chemical group *S* 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- LUHLRKGHPBXRDK-UHFFFAOYSA-N CNC(O)=O.C(C1(SCC(S1)C)C)=NO Chemical compound CNC(O)=O.C(C1(SCC(S1)C)C)=NO LUHLRKGHPBXRDK-UHFFFAOYSA-N 0.000 claims description 2
- XXQPZLGVWHZITM-UHFFFAOYSA-N CNC(O)=O.C(C1(SCCCS1)C)=NO Chemical compound CNC(O)=O.C(C1(SCCCS1)C)=NO XXQPZLGVWHZITM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- -1 oxime carbonates Chemical class 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 229940022682 acetone Drugs 0.000 description 5
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- LUORMBJDPKFRHW-UHFFFAOYSA-N methylcarbamic acid N-[(2-methyl-1,3-dithiolan-2-yl)methylidene]hydroxylamine Chemical compound CNC(O)=O.C(C1(SCCS1)C)=NO LUORMBJDPKFRHW-UHFFFAOYSA-N 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- CNXDLZCBSCSSJC-UHFFFAOYSA-N 2-methyl-1,3-dithiolane-2-carbaldehyde Chemical compound O=CC1(C)SCCS1 CNXDLZCBSCSSJC-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- DNOUKPGPAUUCPC-UHFFFAOYSA-N 2-methylsulfanylpropanal Chemical compound CSC(C)C=O DNOUKPGPAUUCPC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OSELCHNAQDNCHQ-UHFFFAOYSA-N N-[(2-methyl-1,3-dithian-2-yl)methylidene]hydroxylamine Chemical compound C(C1(SCCCS1)C)=NO OSELCHNAQDNCHQ-UHFFFAOYSA-N 0.000 description 2
- TYBKDBNSBDBWFD-UHFFFAOYSA-N N-[(2-methyl-4-phenyl-1,3-dithiolan-2-yl)methylidene]hydroxylamine Chemical compound C(C1(SCC(S1)C1=CC=CC=C1)C)=NO TYBKDBNSBDBWFD-UHFFFAOYSA-N 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000014666 liquid concentrate Nutrition 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 2
- GWPACRXIOTXDLF-UHFFFAOYSA-N n-(2-methylsulfanylpropylidene)hydroxylamine Chemical compound CSC(C)C=NO GWPACRXIOTXDLF-UHFFFAOYSA-N 0.000 description 2
- GBLPIYKBHKESLH-UHFFFAOYSA-N n-[(2-methyl-1,3-dithiolan-2-yl)methylidene]hydroxylamine Chemical compound ON=CC1(C)SCCS1 GBLPIYKBHKESLH-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- IFDZZSXEPSSHNC-ONEGZZNKSA-N (ne)-n-propylidenehydroxylamine Chemical compound CC\C=N\O IFDZZSXEPSSHNC-ONEGZZNKSA-N 0.000 description 1
- CZFIROOFEBLGGD-UHFFFAOYSA-N 1-(2-methyl-1,3-dithiolan-2-yl)ethanone Chemical compound CC(=O)C1(C)SCCS1 CZFIROOFEBLGGD-UHFFFAOYSA-N 0.000 description 1
- NVJUHMXYKCUMQA-UHFFFAOYSA-N 1-ethoxypropane Chemical compound CCCOCC NVJUHMXYKCUMQA-UHFFFAOYSA-N 0.000 description 1
- AAXASCFYJZHFPW-UHFFFAOYSA-N 2,4,6-trimethyl-1,3-dithiane-2-carbaldehyde Chemical compound C(=O)C1(SC(CC(S1)C)C)C AAXASCFYJZHFPW-UHFFFAOYSA-N 0.000 description 1
- ZDPCXBDGYNNQME-UHFFFAOYSA-N 2,4-dimethyl-1,3-dithiolane-2-carbaldehyde Chemical compound CC1CSC(C)(C=O)S1 ZDPCXBDGYNNQME-UHFFFAOYSA-N 0.000 description 1
- GGGGUVPDXBFRQO-UHFFFAOYSA-N 2,5-dimethyl-1,3-benzodithiole-2-carbaldehyde Chemical compound C(=O)C1(SC2=C(S1)C=CC(=C2)C)C GGGGUVPDXBFRQO-UHFFFAOYSA-N 0.000 description 1
- MPTGKIPTVOWUDD-UHFFFAOYSA-N 2-methyl-1,3-dithiane-2-carbaldehyde Chemical compound O=CC1(C)SCCCS1 MPTGKIPTVOWUDD-UHFFFAOYSA-N 0.000 description 1
- KQWNBNZVZCQURY-UHFFFAOYSA-N 2-methyl-4-phenyl-1,3-dithiolane-2-carbaldehyde Chemical compound C(=O)C1(SCC(S1)C1=CC=CC=C1)C KQWNBNZVZCQURY-UHFFFAOYSA-N 0.000 description 1
- UCJRULLFCCYWGU-UHFFFAOYSA-N 4-ethyl-2-methyl-1,3-dithiolane-2-carbaldehyde Chemical compound C(C)C1SC(SC1)(C)C=O UCJRULLFCCYWGU-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241000256118 Aedes aegypti Species 0.000 description 1
- 240000002024 Gossypium herbaceum Species 0.000 description 1
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000243786 Meloidogyne incognita Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- VFQYFJRTTLQAOW-UHFFFAOYSA-N N-(2-propan-2-ylsulfinylpropylidene)hydroxylamine Chemical group C(C)(C)S(=O)C(C=NO)C VFQYFJRTTLQAOW-UHFFFAOYSA-N 0.000 description 1
- UAPGXHJYHZBDQX-UHFFFAOYSA-N N-[(2,4,6-trimethyl-1,3-dithian-2-yl)methylidene]hydroxylamine Chemical compound C(C1(SC(CC(S1)C)C)C)=NO UAPGXHJYHZBDQX-UHFFFAOYSA-N 0.000 description 1
- XEXMHGDNAJCVEH-UHFFFAOYSA-N N-[(2,4-dimethyl-1,3-dithian-2-yl)methylidene]hydroxylamine Chemical compound C(C1(SCCC(S1)C)C)=NO XEXMHGDNAJCVEH-UHFFFAOYSA-N 0.000 description 1
- XMRPFHBFXOEHAF-UHFFFAOYSA-N N-[(4-ethyl-2-methyl-1,3-dithiolan-2-yl)methylidene]hydroxylamine Chemical compound C(C)C1SC(SC1)(C)C=NO XMRPFHBFXOEHAF-UHFFFAOYSA-N 0.000 description 1
- IWUXHDHULZIWLN-UHFFFAOYSA-N N-[1-(2,4-dimethyl-1,3-dithiolan-2-yl)ethylidene]hydroxylamine Chemical compound C(C)(C1(SCC(S1)C)C)=NO IWUXHDHULZIWLN-UHFFFAOYSA-N 0.000 description 1
- KCGZXLHCFLUWRL-UHFFFAOYSA-N N-[1-(2-ethyl-1,3-dithiolan-2-yl)propylidene]hydroxylamine Chemical compound C(C)C1(SCCS1)C(CC)=NO KCGZXLHCFLUWRL-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000003129 miticidal effect Effects 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- HWLRAPYLJJXCOR-UHFFFAOYSA-N n-[(2,4-dimethyl-1,3-dithiolan-2-yl)methylidene]hydroxylamine Chemical compound CC1CSC(C)(C=NO)S1 HWLRAPYLJJXCOR-UHFFFAOYSA-N 0.000 description 1
- QIPYXTXIUGDJTA-UHFFFAOYSA-N n-[1-(2-methyl-1,3-dithiolan-2-yl)ethylidene]hydroxylamine Chemical compound ON=C(C)C1(C)SCCS1 QIPYXTXIUGDJTA-UHFFFAOYSA-N 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 235000009048 phenolic acids Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012970 tertiary amine catalyst Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75375268A | 1968-08-19 | 1968-08-19 | |
| US84114269A | 1969-07-11 | 1969-07-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH539022A true CH539022A (de) | 1973-07-15 |
Family
ID=27115811
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1249569A CH539022A (de) | 1968-08-19 | 1969-08-18 | Verfahren zur Herstellung von Carbamylderivaten substituierter, S-haltiger Alkanal- und Alkanonoxime |
| CH370972A CH554849A (de) | 1968-08-19 | 1969-08-18 | Verfahren zur herstellung von carbamoylderivaten substituierter s-haltiger alkanol- und alkanonoxime. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH370972A CH554849A (de) | 1968-08-19 | 1969-08-18 | Verfahren zur herstellung von carbamoylderivaten substituierter s-haltiger alkanol- und alkanonoxime. |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT296947B (cg-RX-API-DMAC10.html) |
| CH (2) | CH539022A (cg-RX-API-DMAC10.html) |
| DE (1) | DE1941999C3 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2015897A1 (cg-RX-API-DMAC10.html) |
| GB (2) | GB1286542A (cg-RX-API-DMAC10.html) |
| IL (1) | IL32839A (cg-RX-API-DMAC10.html) |
| NL (1) | NL6912150A (cg-RX-API-DMAC10.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3875232A (en) * | 1971-04-08 | 1975-04-01 | Diamond Shamrock Corp | AC Ketoxime carbamates |
-
1969
- 1969-08-08 NL NL6912150A patent/NL6912150A/xx unknown
- 1969-08-18 DE DE1941999A patent/DE1941999C3/de not_active Expired
- 1969-08-18 GB GB41188/69A patent/GB1286542A/en not_active Expired
- 1969-08-18 FR FR6928182A patent/FR2015897A1/fr not_active Withdrawn
- 1969-08-18 IL IL32839A patent/IL32839A/xx unknown
- 1969-08-18 AT AT789769A patent/AT296947B/de not_active IP Right Cessation
- 1969-08-18 CH CH1249569A patent/CH539022A/de not_active IP Right Cessation
- 1969-08-18 CH CH370972A patent/CH554849A/xx not_active IP Right Cessation
- 1969-08-18 GB GB06013/72A patent/GB1286543A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL32839A0 (en) | 1969-11-30 |
| FR2015897A1 (cg-RX-API-DMAC10.html) | 1970-04-30 |
| CH554849A (de) | 1974-10-15 |
| DE1941999A1 (de) | 1970-02-26 |
| AT296947B (de) | 1972-03-10 |
| GB1286543A (en) | 1972-08-23 |
| IL32839A (en) | 1974-06-30 |
| DE1941999B2 (de) | 1973-10-18 |
| DE1941999C3 (de) | 1974-05-16 |
| GB1286542A (en) | 1972-08-23 |
| NL6912150A (cg-RX-API-DMAC10.html) | 1970-02-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |