SU652893A3 - Способ получени -аминосульфенилированных производных 2,3-дигидро-2,2-диметил-7-бензофуранилметилкарбамата - Google Patents
Способ получени -аминосульфенилированных производных 2,3-дигидро-2,2-диметил-7-бензофуранилметилкарбаматаInfo
- Publication number
- SU652893A3 SU652893A3 SU742049056A SU2049056A SU652893A3 SU 652893 A3 SU652893 A3 SU 652893A3 SU 742049056 A SU742049056 A SU 742049056A SU 2049056 A SU2049056 A SU 2049056A SU 652893 A3 SU652893 A3 SU 652893A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- ate
- dimethyl
- wed
- found
- dihydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 238000002329 infrared spectrum Methods 0.000 description 9
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- -1 2,3-Dihydro-2,2-dimethyl-7-benzofuranyl-- (methyl) Chemical group 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- KWTCAZADHRCBIP-UHFFFAOYSA-N morpholin-4-yl thiohypochlorite Chemical compound ClSN1CCOCC1 KWTCAZADHRCBIP-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000286819 Malo Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- OJPXBEZETWQTDZ-UHFFFAOYSA-N dimethylamino thiohypochlorite Chemical compound CN(C)SCl OJPXBEZETWQTDZ-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- FZUJWWOKDIGOKH-UHFFFAOYSA-N sulfuric acid hydrochloride Chemical compound Cl.OS(O)(=O)=O FZUJWWOKDIGOKH-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- 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
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
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)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37870073A | 1973-07-12 | 1973-07-12 | |
| US05/476,767 US4006231A (en) | 1973-07-12 | 1974-06-06 | N-aminosulfenylated derivatives of carbofuran |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU652893A3 true SU652893A3 (ru) | 1979-03-15 |
Family
ID=27008318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU742049056A SU652893A3 (ru) | 1973-07-12 | 1974-07-11 | Способ получени -аминосульфенилированных производных 2,3-дигидро-2,2-диметил-7-бензофуранилметилкарбамата |
Country Status (25)
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4281014A (en) * | 1980-06-04 | 1981-07-28 | Fmc Corporation | Stabilized compositions containing N-aminosulfenylated derivatives of carbofuran |
| IN155624B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1980-09-01 | 1985-02-16 | Otsuka Chemical Co Ltd | |
| US4389528A (en) * | 1980-10-31 | 1983-06-21 | Fmc Corporation | Trialkylamine/sulfur dioxide catalyzed sulfenylation of carbamates |
| US4329293A (en) * | 1980-10-31 | 1982-05-11 | Fmc Corporation | Trialkylamine/sulfur dioxide catalyzed sulfenylation of carbamates |
| US4394383A (en) * | 1981-09-28 | 1983-07-19 | Regents Of The University Of California | N-Alkoxysulfenylcarbamates useful as insecticides |
| US4511578A (en) * | 1982-03-31 | 1985-04-16 | Ciba-Geigy Corporation | Acyclamidosulfenylcarbamates for controlling insects |
| JPS59167566A (ja) * | 1983-03-11 | 1984-09-21 | Otsuka Chem Co Ltd | アミノスルフエニルカ−バメイト誘導体の精製方法 |
| GB8316845D0 (en) * | 1983-06-21 | 1983-07-27 | Fbc Ltd | Insecticides |
| WO1986004214A1 (en) * | 1985-01-24 | 1986-07-31 | Takeda Chemical Industries, Ltd. | Agricultural chemical preparation having alleviated toxicity against fish |
| JPS61260003A (ja) * | 1985-05-14 | 1986-11-18 | Otsuka Chem Co Ltd | 安定な固体農薬組成物 |
| JP2673238B2 (ja) * | 1988-08-18 | 1997-11-05 | アグロカネショウ株式会社 | Ｎ−メチルカーバメイト誘導体、その製法及び殺虫剤 |
| BRPI0500857A (pt) * | 2005-03-09 | 2006-11-14 | Fmc Quimica Do Brasil Ltda | composições pesticidas concentradas à base de carbossulfano, processo para sua preparação, processo para controle de insetos/ácaros/nematódeos, bem como uso das referidas composições |
| EP2039248A1 (de) * | 2007-09-21 | 2009-03-25 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| CN102395271A (zh) | 2009-03-25 | 2012-03-28 | 拜尔农作物科学股份公司 | 具有杀虫和杀螨特性的活性化合物结合物 |
| BR122021003068B1 (pt) | 2009-03-25 | 2021-05-25 | Bayer Cropscience Aktiengesellschaft | composições compreendendo combinações de substâncias ativas nematicidas sinérgicas, seus usos e seu processo de produção, semente resistente a pragas, e método para combate de nematodos |
| CN102786503B (zh) * | 2012-09-05 | 2015-05-27 | 湖南海利常德农药化工有限公司 | 有害杂质克百威低于0.1%的含硫克百威衍生物的制备方法 |
| US20240260577A1 (en) | 2021-05-14 | 2024-08-08 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
| WO2022238576A1 (en) | 2021-05-14 | 2022-11-17 | Syngenta Crop Protection Ag | Seed treatment compositions |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL285555A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1961-11-16 | |||
| DE1187605B (de) * | 1963-03-16 | 1965-02-25 | Bayer Ag | Verfahren zur Herstellung von acylierten Alkansulfensaeureamiden |
| US3564605A (en) * | 1964-10-14 | 1971-02-16 | Fmc Corp | Benzofuran carbamates and method for controlling arthropoda nematoda |
| US3709907A (en) * | 1967-06-05 | 1973-01-09 | Monsanto Co | Dithioamides |
| US3663594A (en) * | 1969-09-04 | 1972-05-16 | Chevron Res | N-substituted aryl carbamates |
| US3699122A (en) * | 1970-06-12 | 1972-10-17 | Chevron Res | N-substituted acylamidosulfenyl chlorides and their method of preparation |
| US3812174A (en) * | 1970-07-14 | 1974-05-21 | Chevron Res | Substituted aryl carbamates |
| DE2045441A1 (de) * | 1970-09-15 | 1972-03-23 | Farbenfabriken Bayer Ag, 5090 Leverkusen | N-Sulfenylierte Dihydrobenzofuranylcarbamate, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide |
| US3843689A (en) * | 1970-11-09 | 1974-10-22 | Chevron Res | N-chlorothio carbamates |
| US3847951A (en) * | 1972-02-28 | 1974-11-12 | Chevron Res | Insecticidal n-thio-substituted carbamates of dihydrobenzofuranols |
| US3897463A (en) * | 1972-12-21 | 1975-07-29 | Gustave K Kohn | Insecticidal N-thio-substituted carbamates of dihydrobenzofuranols |
-
1974
- 1974-06-06 US US05/476,767 patent/US4006231A/en not_active Expired - Lifetime
- 1974-06-27 IL IL45129A patent/IL45129A/en unknown
- 1974-07-03 DO DO1974002784A patent/DOP1974002784A/es unknown
- 1974-07-03 YU YU1873/74A patent/YU36718B/xx unknown
- 1974-07-08 AR AR254591A patent/AR213824A1/es active
- 1974-07-10 JP JP7837974A patent/JPS5339487B2/ja not_active Expired
- 1974-07-10 AT AT570974A patent/AT336947B/de not_active IP Right Cessation
- 1974-07-10 RO RO7479448A patent/RO70061A/ro unknown
- 1974-07-11 DK DK372474A patent/DK142933C/da not_active IP Right Cessation
- 1974-07-11 CA CA204,607A patent/CA1041527A/en not_active Expired
- 1974-07-11 CH CH960774A patent/CH609343A5/xx not_active IP Right Cessation
- 1974-07-11 FR FR7424184A patent/FR2236865B1/fr not_active Expired
- 1974-07-11 BR BR5724/74A patent/BR7405724D0/pt unknown
- 1974-07-11 SU SU742049056A patent/SU652893A3/ru active
- 1974-07-11 IT IT25061/74A patent/IT1053772B/it active
- 1974-07-12 CS CS7400004986A patent/CS180639B2/cs unknown
- 1974-07-12 GB GB3102674A patent/GB1439112A/en not_active Expired
- 1974-07-12 NL NLAANVRAGE7409447,A patent/NL179478C/xx not_active IP Right Cessation
- 1974-07-12 ES ES428234A patent/ES428234A1/es not_active Expired
- 1974-07-12 LU LU70517A patent/LU70517A1/xx unknown
- 1974-07-12 OA OA55246A patent/OA04813A/xx unknown
- 1974-07-12 DE DE2433680A patent/DE2433680C3/de not_active Expired
- 1974-07-12 PH PH16035A patent/PH11102A/en unknown
- 1974-07-12 IE IE1471/74A patent/IE39604B1/xx unknown
- 1974-07-13 EG EG269/74A patent/EG11365A/xx active
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