CH620425A5 - Process for the preparation of new carbamatesulphenylcarbamoyl fluorides - Google Patents
Process for the preparation of new carbamatesulphenylcarbamoyl fluorides Download PDFInfo
- Publication number
- CH620425A5 CH620425A5 CH1506076A CH1506076A CH620425A5 CH 620425 A5 CH620425 A5 CH 620425A5 CH 1506076 A CH1506076 A CH 1506076A CH 1506076 A CH1506076 A CH 1506076A CH 620425 A5 CH620425 A5 CH 620425A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- carbamoyl
- fluoroformylaminosulfenyl
- group
- alkyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 10
- 150000002222 fluorine compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 51
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 34
- -1 phenoxy, naphthoxy Chemical group 0.000 claims description 29
- 150000002923 oximes Chemical class 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000005646 oximino group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- JTNXQVCPQMQLHK-UHFFFAOYSA-N thioacetone Chemical compound CC(C)=S JTNXQVCPQMQLHK-UHFFFAOYSA-N 0.000 claims description 6
- ANQHWGYYOWWJRU-UHFFFAOYSA-N 2,2-dimethylpropanethial Chemical compound CC(C)(C)C=S ANQHWGYYOWWJRU-UHFFFAOYSA-N 0.000 claims description 5
- DIPLXSBTYRDLGV-UHFFFAOYSA-N 2-methyl-2-methylthio-propionaldehyde Natural products CSC(C)(C)C=O DIPLXSBTYRDLGV-UHFFFAOYSA-N 0.000 claims description 5
- 230000000895 acaricidal effect Effects 0.000 claims description 4
- 239000000642 acaricide Substances 0.000 claims description 4
- 125000005133 alkynyloxy 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
- 239000005645 nematicide Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
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- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
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- 238000012360 testing method Methods 0.000 description 45
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- 238000004458 analytical method Methods 0.000 description 17
- DCAMNZNIQSVBSR-UHFFFAOYSA-N n-[carbonofluoridoyl(methyl)amino]sulfanyl-n-methylcarbamoyl fluoride Chemical compound FC(=O)N(C)SN(C)C(F)=O DCAMNZNIQSVBSR-UHFFFAOYSA-N 0.000 description 17
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- ZFGMCJAXIZTVJA-UHFFFAOYSA-N 2-methyl-2-(methylsulfanyl)propanal oxime Chemical compound CSC(C)(C)C=NO ZFGMCJAXIZTVJA-UHFFFAOYSA-N 0.000 description 2
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 241000462639 Epilachna varivestis Species 0.000 description 2
- 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 2
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- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000004563 wettable powder Substances 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
- C07D339/08—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/54—Nitrogen and either oxygen or sulfur atoms
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/636,629 US4338450A (en) | 1975-12-01 | 1975-12-01 | Carbamate-sulfenyl-carbamoyl fluoride compounds |
| US73721976A | 1976-11-04 | 1976-11-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH620425A5 true CH620425A5 (en) | 1980-11-28 |
Family
ID=27092659
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1506076A CH620425A5 (en) | 1975-12-01 | 1976-11-30 | Process for the preparation of new carbamatesulphenylcarbamoyl fluorides |
| CH1053779A CH623034A5 (en) | 1975-12-01 | 1979-11-27 | Process for the preparation of new carbamatesulphenylcarbamoyl fluorides |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1053779A CH623034A5 (en) | 1975-12-01 | 1979-11-27 | Process for the preparation of new carbamatesulphenylcarbamoyl fluorides |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS594429B2 (enExample) |
| AT (1) | AT353803B (enExample) |
| AU (1) | AU515667B2 (enExample) |
| BR (1) | BR7607998A (enExample) |
| CA (1) | CA1069127A (enExample) |
| CH (2) | CH620425A5 (enExample) |
| DE (1) | DE2654282C2 (enExample) |
| DK (1) | DK538276A (enExample) |
| ES (1) | ES468281A1 (enExample) |
| FR (1) | FR2333791A1 (enExample) |
| GB (1) | GB1512910A (enExample) |
| IL (1) | IL51000A (enExample) |
| IT (1) | IT1070073B (enExample) |
| NL (1) | NL7613334A (enExample) |
| SE (1) | SE7612479L (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4234580A (en) * | 1977-03-28 | 1980-11-18 | Union Carbide Corporation | Carbamate thiosulfenylcarbamoyl fluoride compounds |
| US4225615A (en) * | 1978-04-24 | 1980-09-30 | E. I. Du Pont De Nemours And Company | Insecticidal and nematicidal carbamates |
| US4268520A (en) | 1978-04-24 | 1981-05-19 | E. I. Du Pont De Nemours And Company | Insecticidal and nematicidal carbamates |
| US4127605A (en) * | 1978-04-24 | 1978-11-28 | E. I. Du Pont De Nemours And Company | Substituted carbamate intermediate |
| DE2828133A1 (de) * | 1978-06-27 | 1980-01-10 | Bayer Ag | N-sulfenylierte carbamoyloximino-1- methylthio-butane, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
| US4291054A (en) * | 1979-12-10 | 1981-09-22 | E. I. Du Pont De Nemours And Company | Insecticidal carbamoyl sulfides |
| US4511578A (en) * | 1982-03-31 | 1985-04-16 | Ciba-Geigy Corporation | Acyclamidosulfenylcarbamates for controlling insects |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2254359A1 (de) * | 1972-11-07 | 1974-05-16 | Bayer Ag | N-sulfenylierte carbamate, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
-
1976
- 1976-11-09 SE SE7612479A patent/SE7612479L/xx not_active Application Discontinuation
- 1976-11-26 IL IL51000A patent/IL51000A/xx unknown
- 1976-11-29 CA CA266,788A patent/CA1069127A/en not_active Expired
- 1976-11-29 AU AU20066/76A patent/AU515667B2/en not_active Expired
- 1976-11-30 DK DK538276A patent/DK538276A/da unknown
- 1976-11-30 FR FR7636132A patent/FR2333791A1/fr active Granted
- 1976-11-30 DE DE2654282A patent/DE2654282C2/de not_active Expired
- 1976-11-30 NL NL7613334A patent/NL7613334A/xx active Search and Examination
- 1976-11-30 CH CH1506076A patent/CH620425A5/fr not_active IP Right Cessation
- 1976-11-30 BR BR7607998A patent/BR7607998A/pt unknown
- 1976-11-30 GB GB49848/76A patent/GB1512910A/en not_active Expired
- 1976-11-30 AT AT884976A patent/AT353803B/de not_active IP Right Cessation
- 1976-11-30 JP JP51143049A patent/JPS594429B2/ja not_active Expired
- 1976-11-30 IT IT69862/76A patent/IT1070073B/it active
-
1978
- 1978-03-28 ES ES468281A patent/ES468281A1/es not_active Expired
-
1979
- 1979-11-27 CH CH1053779A patent/CH623034A5/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5285106A (en) | 1977-07-15 |
| CH623034A5 (en) | 1981-05-15 |
| BR7607998A (pt) | 1977-11-08 |
| AT353803B (de) | 1979-12-10 |
| DE2654282C2 (de) | 1984-05-24 |
| ES468281A1 (es) | 1978-11-16 |
| IL51000A (en) | 1981-11-30 |
| SE7612479L (sv) | 1977-06-02 |
| IT1070073B (it) | 1985-03-25 |
| FR2333791B1 (enExample) | 1981-01-09 |
| AU2006676A (en) | 1978-06-08 |
| CA1069127A (en) | 1980-01-01 |
| FR2333791A1 (fr) | 1977-07-01 |
| AU515667B2 (en) | 1981-04-16 |
| GB1512910A (en) | 1978-06-01 |
| DK538276A (da) | 1977-06-02 |
| IL51000A0 (en) | 1977-01-31 |
| ATA884976A (de) | 1979-05-15 |
| NL7613334A (nl) | 1977-06-03 |
| DE2654282A1 (de) | 1977-06-08 |
| JPS594429B2 (ja) | 1984-01-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |