DE2462559C3 - 4-Oximino-l -oxa-S-thiacyclopentane und deren 3-Oxide bzw. 33-Dioxide sowie S-Oximino-l-oxa^-thiacyclohexane und deren 4-Oxide bzw. 4,4-Dioxide - Google Patents
4-Oximino-l -oxa-S-thiacyclopentane und deren 3-Oxide bzw. 33-Dioxide sowie S-Oximino-l-oxa^-thiacyclohexane und deren 4-Oxide bzw. 4,4-DioxideInfo
- Publication number
- DE2462559C3 DE2462559C3 DE2462559A DE2462559A DE2462559C3 DE 2462559 C3 DE2462559 C3 DE 2462559C3 DE 2462559 A DE2462559 A DE 2462559A DE 2462559 A DE2462559 A DE 2462559A DE 2462559 C3 DE2462559 C3 DE 2462559C3
- Authority
- DE
- Germany
- Prior art keywords
- oxa
- oximino
- dioxides
- oxides
- ether
- 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.)
- Expired
Links
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 150000002923 oximes Chemical class 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- -1 carbamoyl halide Chemical class 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 4
- 125000001589 carboacyl group Chemical group 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000010183 spectrum analysis Methods 0.000 description 4
- YSEFYOVWKJXNCH-UHFFFAOYSA-N 2-methoxyacetaldehyde Chemical compound COCC=O YSEFYOVWKJXNCH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- UZIXHQMDAJJNKF-UHFFFAOYSA-N n-(1,3-oxathiolan-4-ylidene)hydroxylamine Chemical class ON=C1COCS1 UZIXHQMDAJJNKF-UHFFFAOYSA-N 0.000 description 3
- QBXUKABPNMFBSG-UHFFFAOYSA-N n-(1,4-oxathian-3-ylidene)hydroxylamine Chemical class ON=C1COCCS1 QBXUKABPNMFBSG-UHFFFAOYSA-N 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- JTEWTQMFPYRKNV-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-nitroethane Chemical compound [O-][N+](=O)CCOCCBr JTEWTQMFPYRKNV-UHFFFAOYSA-N 0.000 description 2
- KIPMDPDAFINLIV-UHFFFAOYSA-N 2-nitroethanol Chemical compound OCC[N+]([O-])=O KIPMDPDAFINLIV-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- OJBPZYLKOSHQKS-UHFFFAOYSA-N n-(5-methyl-1,3-oxathiolan-4-ylidene)hydroxylamine Chemical compound CC1OCSC1=NO OJBPZYLKOSHQKS-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 2
- SMJRBWINMFUUDS-UHFFFAOYSA-M thien-2-ylacetate Chemical class [O-]C(=O)CC1=CC=CS1 SMJRBWINMFUUDS-UHFFFAOYSA-M 0.000 description 2
- 239000005051 trimethylchlorosilane Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- WJJSZTJGFCFNKI-UHFFFAOYSA-N 1,3-oxathiolane Chemical compound C1CSCO1 WJJSZTJGFCFNKI-UHFFFAOYSA-N 0.000 description 1
- BQSXAPBXZAMKIO-UHFFFAOYSA-N 1-(chloromethoxy)-2-nitroethane Chemical compound [O-][N+](=O)CCOCCl BQSXAPBXZAMKIO-UHFFFAOYSA-N 0.000 description 1
- FOZVXADQAHVUSV-UHFFFAOYSA-N 1-bromo-2-(2-bromoethoxy)ethane Chemical compound BrCCOCCBr FOZVXADQAHVUSV-UHFFFAOYSA-N 0.000 description 1
- PVBMXMKIKMJQRK-UHFFFAOYSA-N 1-chloro-4-(4-chlorobutoxy)butane Chemical compound ClCCCCOCCCCCl PVBMXMKIKMJQRK-UHFFFAOYSA-N 0.000 description 1
- OVKLPPNSWFJNHA-UHFFFAOYSA-N 1-methoxy-3-nitropropan-2-ol Chemical compound COCC(O)C[N+]([O-])=O OVKLPPNSWFJNHA-UHFFFAOYSA-N 0.000 description 1
- PFNCKQIYLAVYJF-UHFFFAOYSA-N 1-nitropropan-2-ol Chemical compound CC(O)C[N+]([O-])=O PFNCKQIYLAVYJF-UHFFFAOYSA-N 0.000 description 1
- JYWKEVKEKOTYEX-UHFFFAOYSA-N 2,6-dibromo-4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=C(Br)C(=O)C(Br)=C1 JYWKEVKEKOTYEX-UHFFFAOYSA-N 0.000 description 1
- OJUIPQSJYIPAQM-UHFFFAOYSA-N C(N)(=O)C1SC(OC1)=NO Chemical class C(N)(=O)C1SC(OC1)=NO OJUIPQSJYIPAQM-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- CCPHAMSKHBDMDS-UHFFFAOYSA-N Chetoseminudin B Natural products C=1NC2=CC=CC=C2C=1CC1(SC)NC(=O)C(CO)(SC)N(C)C1=O CCPHAMSKHBDMDS-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- VUYCBBHNGBWOJM-UHFFFAOYSA-N NCOCl Chemical compound NCOCl VUYCBBHNGBWOJM-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 238000003459 chloroalkylation reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GDTQDTLDXHYMHN-UHFFFAOYSA-N n-(2-methyl-1,3-oxathiolan-4-ylidene)hydroxylamine Chemical compound CC1OCC(=NO)S1 GDTQDTLDXHYMHN-UHFFFAOYSA-N 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- BVJHVLCYGPGYGZ-UHFFFAOYSA-N s-(1-nitropropan-2-yloxymethyl) ethanethioate Chemical compound [O-][N+](=O)CC(C)OCSC(C)=O BVJHVLCYGPGYGZ-UHFFFAOYSA-N 0.000 description 1
- NGJNDDJSTKIAHZ-UHFFFAOYSA-N s-[2-(2-acetylsulfanylethoxy)ethyl] ethanethioate Chemical compound CC(=O)SCCOCCSC(C)=O NGJNDDJSTKIAHZ-UHFFFAOYSA-N 0.000 description 1
- MBSRJALAVMFWID-UHFFFAOYSA-N s-[2-(2-nitroethoxy)ethyl] ethanethioate Chemical compound CC(=O)SCCOCC[N+]([O-])=O MBSRJALAVMFWID-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- RBBWNXJFTBCLKT-UHFFFAOYSA-M sodium;ethanethioate Chemical compound [Na+].CC([S-])=O RBBWNXJFTBCLKT-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0892—Compounds with a Si-O-N linkage
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/08—Systemic pesticides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/10—Insect repellent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/347,446 US3956500A (en) | 1973-04-03 | 1973-04-03 | Carbamate pesticidal compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2462559A1 DE2462559A1 (de) | 1977-08-18 |
| DE2462559B2 DE2462559B2 (de) | 1979-09-13 |
| DE2462559C3 true DE2462559C3 (de) | 1980-06-04 |
Family
ID=23363729
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2462559A Expired DE2462559C3 (de) | 1973-04-03 | 1974-04-03 | 4-Oximino-l -oxa-S-thiacyclopentane und deren 3-Oxide bzw. 33-Dioxide sowie S-Oximino-l-oxa^-thiacyclohexane und deren 4-Oxide bzw. 4,4-Dioxide |
| DE2416054A Expired DE2416054C3 (de) | 1973-04-03 | 1974-04-03 | 4-Carbamoyloximino-l-oxa-thiacyclopentane und deren 3-Oxide bzw. 33-Dioxide sowie S-Carbamoyloximino-l-oxa^-thiacyclohexane und deren 4-Oxide bzw. 4,4-Dioxide sowie diese Verbindungen enthaltende Schädlingsbekämpfungsmittel |
| DE2462797A Expired DE2462797C2 (de) | 1973-04-03 | 1974-04-03 | 2-Hydroximino-1,4-oxathiacyclohexane |
| DE19742462422 Pending DE2462422A1 (de) | 1973-04-03 | 1974-04-03 | 2-carbamoyloximino-1,4-oxathiacyclohexane sowie deren 4-oxide und 4,4-dioxide und verfahren zu deren herstellung |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2416054A Expired DE2416054C3 (de) | 1973-04-03 | 1974-04-03 | 4-Carbamoyloximino-l-oxa-thiacyclopentane und deren 3-Oxide bzw. 33-Dioxide sowie S-Carbamoyloximino-l-oxa^-thiacyclohexane und deren 4-Oxide bzw. 4,4-Dioxide sowie diese Verbindungen enthaltende Schädlingsbekämpfungsmittel |
| DE2462797A Expired DE2462797C2 (de) | 1973-04-03 | 1974-04-03 | 2-Hydroximino-1,4-oxathiacyclohexane |
| DE19742462422 Pending DE2462422A1 (de) | 1973-04-03 | 1974-04-03 | 2-carbamoyloximino-1,4-oxathiacyclohexane sowie deren 4-oxide und 4,4-dioxide und verfahren zu deren herstellung |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3956500A (cg-RX-API-DMAC10.html) |
| JP (1) | JPS49126825A (cg-RX-API-DMAC10.html) |
| AT (1) | AT331564B (cg-RX-API-DMAC10.html) |
| BE (1) | BE813206A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1025871A (cg-RX-API-DMAC10.html) |
| CH (1) | CH593608A5 (cg-RX-API-DMAC10.html) |
| DE (4) | DE2462559C3 (cg-RX-API-DMAC10.html) |
| ES (1) | ES424853A1 (cg-RX-API-DMAC10.html) |
| FR (2) | FR2224470A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1434167A (cg-RX-API-DMAC10.html) |
| IL (1) | IL44552A (cg-RX-API-DMAC10.html) |
| IN (1) | IN140615B (cg-RX-API-DMAC10.html) |
| NL (1) | NL7404474A (cg-RX-API-DMAC10.html) |
| OA (1) | OA04811A (cg-RX-API-DMAC10.html) |
| TR (1) | TR17887A (cg-RX-API-DMAC10.html) |
| ZA (1) | ZA741969B (cg-RX-API-DMAC10.html) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3992549A (en) * | 1973-05-25 | 1976-11-16 | Union Carbide Corporation | Pesticidal compositions and methods of killing pests using N-polyhalo-alkanesulfenyl carbamoyloximino di-sulfur containing heterocyclic compounds |
| US4496721A (en) * | 1975-12-01 | 1985-01-29 | Union Carbide Corporation | Process for preparing symmetrical bis-carbamates |
| US4073930A (en) * | 1976-06-01 | 1978-02-14 | Union Carbide Corporation | Carbamoyloximes and oximes and insecticidal and miticidal compositions and methods employing them |
| US4072750A (en) * | 1976-06-01 | 1978-02-07 | Union Carbide Corporation | 1,3,5-Trithiane and 1,3,5-oxadithiane carbamoyloxime compounds and insecticidal and miticidal compositions and methods employing them |
| US4235902A (en) * | 1976-06-21 | 1980-11-25 | Union Carbide Corporation | Pesticidal carbamate esters of 5-oximino-1,3-oxazolidin-4-ones |
| US4156731A (en) * | 1976-09-29 | 1979-05-29 | Union Carbide Corporation | Heterocyclic oxime compounds and carbamoyloxime derivatives |
| US5061726A (en) * | 1989-03-30 | 1991-10-29 | The Regents Of The University Of California | Alkynylphenyl-substituted 1,3-oxathione compounds with pesticidal activity |
| MXPA04008651A (es) * | 2002-03-28 | 2005-09-08 | Basf Ag | Metodo para purificar un pesticida. |
| CN101048423B (zh) * | 2004-08-26 | 2011-06-08 | 日本新药株式会社 | 亚磷酰胺化合物及低聚核糖核酸的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3193561A (en) * | 1962-09-20 | 1965-07-06 | American Cyanamid Co | Novel carbamates of 5- and 6-membered hetero-sulfur compounds and process for preparing same |
| US3338782A (en) * | 1962-09-20 | 1967-08-29 | American Cyanamid Co | Insecticidal compositions containing carbamates of 5- and 6-membered hetero-sulfur compounds and method of controlling insects with same |
| US3183148A (en) * | 1962-09-20 | 1965-05-11 | American Cyanamid Co | Combating nematodes with carbamate hetero-sulfur compounds |
| US3365361A (en) * | 1965-02-23 | 1968-01-23 | American Cyanamid Co | Plant root-knot gall nematode control with 5-carbamoyloxyimino-1, 3-dithianes |
-
1973
- 1973-04-03 US US05/347,446 patent/US3956500A/en not_active Expired - Lifetime
-
1974
- 1974-03-27 ZA ZA00741969A patent/ZA741969B/xx unknown
- 1974-03-28 ES ES424853A patent/ES424853A1/es not_active Expired
- 1974-03-28 CA CA196,560A patent/CA1025871A/en not_active Expired
- 1974-03-29 GB GB1394674A patent/GB1434167A/en not_active Expired
- 1974-03-29 FR FR7411368A patent/FR2224470A1/fr not_active Withdrawn
- 1974-04-02 IN IN737/CAL/74A patent/IN140615B/en unknown
- 1974-04-02 TR TR17887A patent/TR17887A/xx unknown
- 1974-04-02 BE BE142769A patent/BE813206A/xx unknown
- 1974-04-02 AT AT272074A patent/AT331564B/de not_active IP Right Cessation
- 1974-04-02 NL NL7404474A patent/NL7404474A/xx unknown
- 1974-04-02 IL IL44552A patent/IL44552A/xx unknown
- 1974-04-02 CH CH459074A patent/CH593608A5/xx not_active IP Right Cessation
- 1974-04-02 JP JP49036721A patent/JPS49126825A/ja active Pending
- 1974-04-03 DE DE2462559A patent/DE2462559C3/de not_active Expired
- 1974-04-03 DE DE2416054A patent/DE2416054C3/de not_active Expired
- 1974-04-03 DE DE2462797A patent/DE2462797C2/de not_active Expired
- 1974-04-03 DE DE19742462422 patent/DE2462422A1/de active Pending
- 1974-04-04 OA OA55171A patent/OA04811A/xx unknown
-
1978
- 1978-04-21 FR FR7811899A patent/FR2396009A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2462559A1 (de) | 1977-08-18 |
| US3956500A (en) | 1976-05-11 |
| CA1025871A (en) | 1978-02-07 |
| AU6742774A (en) | 1975-10-02 |
| DE2416054C3 (de) | 1978-10-19 |
| GB1434167A (en) | 1976-05-05 |
| DE2462559B2 (de) | 1979-09-13 |
| DE2462797B1 (de) | 1979-06-07 |
| CH593608A5 (cg-RX-API-DMAC10.html) | 1977-12-15 |
| DE2462422A1 (de) | 1977-03-03 |
| DE2416054B2 (de) | 1978-02-16 |
| FR2396009A1 (fr) | 1979-01-26 |
| ZA741969B (en) | 1975-04-30 |
| BE813206A (fr) | 1974-10-02 |
| AT331564B (de) | 1976-08-25 |
| OA04811A (fr) | 1980-10-31 |
| IL44552A (en) | 1979-09-30 |
| JPS49126825A (cg-RX-API-DMAC10.html) | 1974-12-04 |
| DE2416054A1 (de) | 1974-10-24 |
| ATA272074A (de) | 1975-11-15 |
| IL44552A0 (en) | 1974-06-30 |
| NL7404474A (cg-RX-API-DMAC10.html) | 1974-10-07 |
| FR2396009B1 (cg-RX-API-DMAC10.html) | 1980-06-13 |
| ES424853A1 (es) | 1976-09-16 |
| IN140615B (cg-RX-API-DMAC10.html) | 1976-12-11 |
| DE2462797C2 (de) | 1980-01-31 |
| FR2224470A1 (cg-RX-API-DMAC10.html) | 1974-10-31 |
| TR17887A (tr) | 1976-09-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: UNION CARBIDE CORP., 06817 DANBURY, CONN., US |
|
| 8339 | Ceased/non-payment of the annual fee |