JPS5877878A - カ−バメイト化合物の製造法 - Google Patents
カ−バメイト化合物の製造法Info
- Publication number
- JPS5877878A JPS5877878A JP17792881A JP17792881A JPS5877878A JP S5877878 A JPS5877878 A JP S5877878A JP 17792881 A JP17792881 A JP 17792881A JP 17792881 A JP17792881 A JP 17792881A JP S5877878 A JPS5877878 A JP S5877878A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- compound
- reaction
- dihydro
- 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.)
- Granted
Links
- -1 carbamate compound Chemical class 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- ZBVZOMFYISPWMD-UHFFFAOYSA-N amino thiohypochlorite Chemical class NSCl ZBVZOMFYISPWMD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 28
- 150000007514 bases Chemical class 0.000 abstract description 12
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 abstract description 10
- 239000000126 substance Substances 0.000 abstract description 9
- 239000002994 raw material Substances 0.000 abstract description 7
- 241001465754 Metazoa Species 0.000 abstract description 5
- 230000000749 insecticidal effect Effects 0.000 abstract description 5
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- YOSCIBHNIINXGQ-UHFFFAOYSA-N (2,2-dimethyl-3H-1-benzofuran-7-yl) N-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2.CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 YOSCIBHNIINXGQ-UHFFFAOYSA-N 0.000 abstract 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 229910001868 water Inorganic materials 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 5
- 238000001308 synthesis method Methods 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 3
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 3
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000012320 chlorinating reagent Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 150000002019 disulfides Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 101150030723 RIR2 gene Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UXLYEJGCYZAZDX-UHFFFAOYSA-N [bis(2-cyanoethyl)amino] thiohypochlorite Chemical compound N#CCCN(SCl)CCC#N UXLYEJGCYZAZDX-UHFFFAOYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- YZPXDEXTKPFTGC-UHFFFAOYSA-N ethyl 2-(butylamino)propanoate Chemical compound CCCCNC(C)C(=O)OCC YZPXDEXTKPFTGC-UHFFFAOYSA-N 0.000 description 1
- CXDAFOJQFCKBLP-UHFFFAOYSA-N ethyl 2-[acetyl(chlorosulfanyl)amino]acetate Chemical compound CCOC(=O)CN(SCl)C(C)=O CXDAFOJQFCKBLP-UHFFFAOYSA-N 0.000 description 1
- XRIZQNOCVIQTRX-UHFFFAOYSA-N ethyl 2-[chlorosulfanyl(ethoxycarbonyl)amino]acetate Chemical compound CCOC(=O)CN(SCl)C(=O)OCC XRIZQNOCVIQTRX-UHFFFAOYSA-N 0.000 description 1
- AMBDTBHJFINMSE-UHFFFAOYSA-N ethyl 2-acetamidoacetate Chemical compound CCOC(=O)CNC(C)=O AMBDTBHJFINMSE-UHFFFAOYSA-N 0.000 description 1
- FTKLDWGDFWLILC-UHFFFAOYSA-N ethyl 3-[butyl(chlorosulfanyl)amino]propanoate Chemical compound CCCCN(SCl)CCC(=O)OCC FTKLDWGDFWLILC-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical class COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000005271 tributylamino group Chemical group 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (31)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17792881A JPS5877878A (ja) | 1981-11-05 | 1981-11-05 | カ−バメイト化合物の製造法 |
| PH27023A PH19220A (en) | 1981-03-30 | 1982-03-19 | Aminosulfenyl chloride derivatives and process for preparing the same |
| CA000399286A CA1188706A (en) | 1981-03-30 | 1982-03-24 | Aminosulfenyl chloride derivatives, process for preparing the same |
| US06/361,931 US4421693A (en) | 1981-03-30 | 1982-03-25 | Aminosulfenyl chloride derivatives |
| DE3211087A DE3211087C2 (de) | 1981-03-30 | 1982-03-25 | Aminosulfenylchloridderivate, Verfahren zu deren Herstellung und deren Verwendung |
| AR288882A AR230833A1 (es) | 1981-03-30 | 1982-03-26 | Derivados de aminosulfeniloloruro,procedimiento para su preparacion y procedimiento para la preparacion de derivados de carbamato utiles como compuestos insecticidas,acaricidas y nematocidas a partir de dichos derivados |
| ES510885A ES510885A0 (es) | 1981-03-30 | 1982-03-27 | Procedimiento de preparar derivados de cloruro de aminosulfenilo, utiles para insecticidas |
| GR67741A GR75920B (enrdf_load_stackoverflow) | 1981-03-30 | 1982-03-29 | |
| NZ20982782A NZ209827A (en) | 1981-03-30 | 1982-03-29 | Process for the preparation of 2,3-dihydro-2,2-dimethylbenzofuran-7-yl n-(n,n-disubstituted aminosulphenyl)-n-methyl carbamate derivatives |
| NZ200163A NZ200163A (en) | 1981-03-30 | 1982-03-29 | Aminosulphenyl chloride derivatives and methods for their preparation |
| NL8201290A NL8201290A (nl) | 1981-03-30 | 1982-03-29 | Aminosulfenylchloridederivaten, werkwijze voor het bereiden daarvan en werkwijze voor het bereiden van carbamaatderivaten, die geschikt zijn als insekticiden, miticiden of nematociden. |
| GB8209194A GB2096994B (en) | 1981-03-30 | 1982-03-29 | Aminosulfenyl chloride derivatives and process for preparing carbamate derivatives useful as ins |
| SE8202001A SE456578B (sv) | 1981-03-30 | 1982-03-29 | Aminosulfenylkloridderivat, forfarande for framstellning derav samt forfarande for framstellning av karbamatderivat, som er anvendbara sasom insekticida, miticida eller nematocida foreningar |
| MX192032A MX160562A (es) | 1981-03-30 | 1982-03-29 | Un proceso para preparar derivados de cloruro de aninosulfenilo |
| CH1915/82A CH653016A5 (fr) | 1981-03-30 | 1982-03-29 | Derives du chlorure d'aminosulfenyle, procede pour la preparation de ceux-ci et utilisation de ces derives pour la preparation de carbamates. |
| IT48109/82A IT1147830B (it) | 1981-03-30 | 1982-03-29 | Derivati di amminosolfenilcloruri,procedimento per prepararli nonche' per preparare da essi derivati carbammati utili come pesticidi |
| EG16782A EG15607A (en) | 1981-05-22 | 1982-03-29 | Aminosulfenyl chloride derivatives,process for preparing the same,and process for preparing carbamate derivatives useful as insecticidal,miticidal or nematocidal compounds |
| TR21303A TR21303A (tr) | 1981-03-30 | 1982-03-30 | Aminosulfenil klor*r t*revleri,bunlari hazirlamaya mahsus usul ve ensektisid,mitisid veya nematosid bilesikler olarak kullanilmaya elverisli olan karbomat t*revlerini hazirlamaya mahsus usul |
| DD82238568A DD204251A5 (de) | 1981-03-30 | 1982-03-30 | Verfahren zur herstellung von aminosulfenylchloridderivaten |
| IL65384A IL65384A (en) | 1981-03-30 | 1982-03-30 | Aminosulfenyl chloride derivatives,their preparation and their use as intermediates for preparing carbamate derivatives |
| KR8201384A KR880002299B1 (ko) | 1981-03-30 | 1982-03-30 | 아미노설페닐 클로라이드 유도체 및 카바메이트 유도체의 제조방법 |
| IN354/CAL/82A IN156106B (enrdf_load_stackoverflow) | 1981-03-30 | 1982-03-30 | |
| MA19629A MA19424A1 (fr) | 1981-03-30 | 1982-03-30 | Chlorures de sulfenyle, procede pour leur preparation et celle de carbamates servant de composes insecticides acaricides ou nematicides |
| FR8205475A FR2502616B1 (fr) | 1981-03-30 | 1982-03-30 | Chlorures d'aminosulfenyle, procede pour leur preparation et leur utilisation dans la preparation de carbamates possedant des proprietes insecticides, miticides ou nematocides |
| DD82246179A DD208803A5 (de) | 1981-03-30 | 1982-03-30 | Verfahren zur herstellung eines 2,3-dihydro-2,2-dimethylbenzofuran-7-yl-n-(n,n-disubstituierten aminosulfenyl)-n-methyl-carbamats |
| HU495982A HU198463B (en) | 1981-05-22 | 1982-03-30 | Process for producing carbamate derivatives with insecticidal effect |
| AU82143/82A AU545481B2 (en) | 1981-03-30 | 1982-03-30 | Aminosulfenyl chlorides and preparation of 7-benzofuryl- n-(aminosulfenyl)carbamates |
| ES521601A ES521601A0 (es) | 1981-03-30 | 1983-03-31 | Metodo de obtencion de derivados n-metilcarbamaticos utiles para insecticidas. |
| IN357/MAS/84A IN160648B (enrdf_load_stackoverflow) | 1981-03-30 | 1984-03-17 | |
| CA000453645A CA1187089A (en) | 1981-03-30 | 1984-05-04 | Process for preparing carbamate derivatives useful as insecticidal, miticidal or nematocidal compounds |
| CS843846A CS268161B2 (en) | 1981-05-22 | 1984-05-22 | Process for preparing 2,3-dihydro-2,2-dimethylbenzofuran-7-n-/n,n-disubstituted aminosulphenyl/-n-methylcarbamate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17792881A JPS5877878A (ja) | 1981-11-05 | 1981-11-05 | カ−バメイト化合物の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5877878A true JPS5877878A (ja) | 1983-05-11 |
| JPH0216307B2 JPH0216307B2 (enrdf_load_stackoverflow) | 1990-04-16 |
Family
ID=16039512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17792881A Granted JPS5877878A (ja) | 1981-03-30 | 1981-11-05 | カ−バメイト化合物の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5877878A (enrdf_load_stackoverflow) |
-
1981
- 1981-11-05 JP JP17792881A patent/JPS5877878A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0216307B2 (enrdf_load_stackoverflow) | 1990-04-16 |
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