DE2402370A1 - Substituierte benzofuranylester - Google Patents
Substituierte benzofuranylesterInfo
- Publication number
- DE2402370A1 DE2402370A1 DE2402370A DE2402370A DE2402370A1 DE 2402370 A1 DE2402370 A1 DE 2402370A1 DE 2402370 A DE2402370 A DE 2402370A DE 2402370 A DE2402370 A DE 2402370A DE 2402370 A1 DE2402370 A1 DE 2402370A1
- Authority
- DE
- Germany
- Prior art keywords
- spp
- substituted
- dibydro
- dimethyl
- radical
- 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.)
- Withdrawn
Links
- 239000004480 active ingredient Substances 0.000 claims description 22
- 239000004009 herbicide Substances 0.000 claims description 15
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 230000002363 herbicidal effect Effects 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- WTJCTMNEAXSSDE-UHFFFAOYSA-N acetyl(methyl)sulfamic acid Chemical compound CC(N(C)S(O)(=O)=O)=O WTJCTMNEAXSSDE-UHFFFAOYSA-N 0.000 claims description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 2
- 101001003187 Hordeum vulgare Alpha-amylase/subtilisin inhibitor Proteins 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- BTAAXEFROUUDIL-UHFFFAOYSA-M potassium;sulfamate Chemical compound [K+].NS([O-])(=O)=O BTAAXEFROUUDIL-UHFFFAOYSA-M 0.000 claims 1
- -1 alkynyl radical Chemical class 0.000 description 31
- 150000003839 salts Chemical class 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 22
- 239000000243 solution Substances 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 150000002148 esters Chemical class 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 150000001408 amides Chemical group 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- 241000196324 Embryophyta Species 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
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- 239000013543 active substance Substances 0.000 description 3
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- 230000000694 effects Effects 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 3
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- 239000000126 substance Substances 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- 235000002767 Daucus carota Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 241000195952 Equisetaceae Species 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 241000801118 Lepidium Species 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 241000219071 Malvaceae Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 241000219793 Trifolium Species 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000000729 antidote Substances 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 2
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- 239000002917 insecticide Substances 0.000 description 2
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- 229910052744 lithium Inorganic materials 0.000 description 2
- 125000005394 methallyl group Chemical group 0.000 description 2
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
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- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/83—Oxygen 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
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- 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
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
Priority Applications (25)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2402370A DE2402370A1 (de) | 1974-01-18 | 1974-01-18 | Substituierte benzofuranylester |
| DK632474A DK632474A (US07368563-20080506-C00056.png) | 1974-01-18 | 1974-12-05 | |
| AU76600/74A AU486452B2 (en) | 1974-01-18 | 1974-12-18 | Substituted benzofuranyl esters |
| IL46287A IL46287A (en) | 1974-01-18 | 1974-12-19 | 2,3-dihydro-3,3-dimethylbenzo-furan-5-yl aminosulfonate derivatives their production and their use as herbicides |
| FR7442348A FR2258385B1 (US07368563-20080506-C00056.png) | 1974-01-18 | 1974-12-20 | |
| JP49146898A JPS50101533A (US07368563-20080506-C00056.png) | 1974-01-18 | 1974-12-23 | |
| BE151944A BE823879A (fr) | 1974-01-18 | 1974-12-27 | Nouveaux esters de benzofuranne-5-yle |
| NL7500326A NL7500326A (nl) | 1974-01-18 | 1975-01-10 | Werkwijze voor het bereiden van gesubstitueerde benzofuranylesters. |
| BR273/75A BR7500273A (pt) | 1974-01-18 | 1975-01-15 | Composicoes herbicidas |
| BG7528725A BG25979A3 (US07368563-20080506-C00056.png) | 1974-01-18 | 1975-01-15 | |
| IT47690/75A IT1050270B (it) | 1974-01-18 | 1975-01-15 | Esteri benzofuranilici sostituiti |
| CH44275A CH595754A5 (US07368563-20080506-C00056.png) | 1974-01-18 | 1975-01-15 | |
| SU2097790A SU519108A3 (ru) | 1974-01-18 | 1975-01-16 | Гербицидное средство |
| PL1975177378A PL91954B1 (US07368563-20080506-C00056.png) | 1974-01-18 | 1975-01-16 | |
| HU75BA00003190A HU171224B (hu) | 1974-01-18 | 1975-01-16 | Gerbicidy soderzhahhie zamehhennye slozhnykh efirov benzofuranola i sposob poluchenija aktivnogo agenta |
| CA218,030A CA1049539A (en) | 1974-01-18 | 1975-01-16 | Substituted benzofuranyl esters |
| LU71663A LU71663A1 (US07368563-20080506-C00056.png) | 1974-01-18 | 1975-01-16 | |
| DD183665A DD115561A5 (US07368563-20080506-C00056.png) | 1974-01-18 | 1975-01-16 | |
| GB2067/75A GB1488575A (en) | 1974-01-18 | 1975-01-17 | Substituted benzo-furanyl esters and their use as herbicides |
| CS7500000357A CS181286B2 (en) | 1974-01-18 | 1975-01-17 | Herbicidal agent |
| ES433918A ES433918A1 (es) | 1974-01-18 | 1975-01-17 | Procedimiento para la obtencion de herbicidas. |
| AT33675A AT339659B (de) | 1974-01-18 | 1975-01-17 | Herbizid |
| NO750140A NO750140L (US07368563-20080506-C00056.png) | 1974-01-18 | 1975-01-17 | |
| ZA00750335A ZA75335B (en) | 1974-01-18 | 1975-01-17 | Substituted benzofuranyl esters |
| SE7500519A SE7500519L (sv) | 1974-01-18 | 1975-01-17 | Substituerade bensofuranylestrar. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2402370A DE2402370A1 (de) | 1974-01-18 | 1974-01-18 | Substituierte benzofuranylester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2402370A1 true DE2402370A1 (de) | 1975-07-31 |
Family
ID=5905110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2402370A Withdrawn DE2402370A1 (de) | 1974-01-18 | 1974-01-18 | Substituierte benzofuranylester |
Country Status (24)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6476011B1 (en) | 1991-08-28 | 2002-11-05 | Sterix Limited | Methods for introducing an estrogenic compound |
| US6011024A (en) | 1991-08-28 | 2000-01-04 | Imperial College Of Science Technology & Medicine | Steroid sulphatase inhibitors |
| US6903084B2 (en) | 1991-08-29 | 2005-06-07 | Sterix Limited | Steroid sulphatase inhibitors |
| GB2331988B (en) * | 1997-12-04 | 2003-04-16 | Imperial College | Polycyclic sulphamate inhibitors or oestrone sulphatase |
| US7335650B2 (en) | 2000-01-14 | 2008-02-26 | Sterix Limited | Composition |
-
1974
- 1974-01-18 DE DE2402370A patent/DE2402370A1/de not_active Withdrawn
- 1974-12-05 DK DK632474A patent/DK632474A/da unknown
- 1974-12-19 IL IL46287A patent/IL46287A/xx unknown
- 1974-12-20 FR FR7442348A patent/FR2258385B1/fr not_active Expired
- 1974-12-23 JP JP49146898A patent/JPS50101533A/ja active Pending
- 1974-12-27 BE BE151944A patent/BE823879A/xx unknown
-
1975
- 1975-01-10 NL NL7500326A patent/NL7500326A/xx not_active Application Discontinuation
- 1975-01-15 IT IT47690/75A patent/IT1050270B/it active
- 1975-01-15 CH CH44275A patent/CH595754A5/xx not_active IP Right Cessation
- 1975-01-15 BG BG7528725A patent/BG25979A3/xx unknown
- 1975-01-15 BR BR273/75A patent/BR7500273A/pt unknown
- 1975-01-16 SU SU2097790A patent/SU519108A3/ru active
- 1975-01-16 LU LU71663A patent/LU71663A1/xx unknown
- 1975-01-16 CA CA218,030A patent/CA1049539A/en not_active Expired
- 1975-01-16 HU HU75BA00003190A patent/HU171224B/hu unknown
- 1975-01-16 PL PL1975177378A patent/PL91954B1/pl unknown
- 1975-01-16 DD DD183665A patent/DD115561A5/xx unknown
- 1975-01-17 SE SE7500519A patent/SE7500519L/xx unknown
- 1975-01-17 ZA ZA00750335A patent/ZA75335B/xx unknown
- 1975-01-17 AT AT33675A patent/AT339659B/de not_active IP Right Cessation
- 1975-01-17 CS CS7500000357A patent/CS181286B2/cs unknown
- 1975-01-17 ES ES433918A patent/ES433918A1/es not_active Expired
- 1975-01-17 NO NO750140A patent/NO750140L/no unknown
- 1975-01-17 GB GB2067/75A patent/GB1488575A/en not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |