CA2123324A1 - Thiophenes and polythiophenes, their preparation and their use - Google Patents
Thiophenes and polythiophenes, their preparation and their useInfo
- Publication number
- CA2123324A1 CA2123324A1 CA002123324A CA2123324A CA2123324A1 CA 2123324 A1 CA2123324 A1 CA 2123324A1 CA 002123324 A CA002123324 A CA 002123324A CA 2123324 A CA2123324 A CA 2123324A CA 2123324 A1 CA2123324 A1 CA 2123324A1
- Authority
- CA
- Canada
- Prior art keywords
- methylthio
- formula
- compound
- hydrogen
- thiophene
- 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.)
- Abandoned
Links
- 229930192474 thiophene Natural products 0.000 title claims abstract description 14
- 229920000123 polythiophene Polymers 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims description 9
- 150000003577 thiophenes Chemical class 0.000 title abstract description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims description 24
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 241000244206 Nematoda Species 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 5
- 241000607479 Yersinia pestis Species 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 241000239223 Arachnida Species 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- LCTMUKRQVFWKTD-UHFFFAOYSA-N 3,4-bis(methylsulfanyl)thiophene Chemical compound CSC1=CSC=C1SC LCTMUKRQVFWKTD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 241000238631 Hexapoda Species 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 2
- AUVMJDLPMROHJR-UHFFFAOYSA-N 4-methylsulfanyl-2-(4-methylsulfanylthiophen-2-yl)thiophene Chemical compound CSC1=CSC(C=2SC=C(SC)C=2)=C1 AUVMJDLPMROHJR-UHFFFAOYSA-N 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract description 2
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- -1 pentane Chemical class 0.000 description 31
- 239000000203 mixture Substances 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
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- 150000002500 ions Chemical class 0.000 description 6
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- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
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- 239000007787 solid Substances 0.000 description 4
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
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- 239000007858 starting material Substances 0.000 description 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- ULTVOHNOAKYULF-UHFFFAOYSA-N 2,5-dibromo-3-methylsulfanylthiophene Chemical compound CSC=1C=C(Br)SC=1Br ULTVOHNOAKYULF-UHFFFAOYSA-N 0.000 description 2
- CPLMERMFOQWINU-UHFFFAOYSA-N 2-bromo-4-methylsulfanylthiophene Chemical compound CSC1=CSC(Br)=C1 CPLMERMFOQWINU-UHFFFAOYSA-N 0.000 description 2
- SXNCMLQAQIGJDO-UHFFFAOYSA-N 2-bromo-5-(5-bromothiophen-2-yl)thiophene Chemical compound S1C(Br)=CC=C1C1=CC=C(Br)S1 SXNCMLQAQIGJDO-UHFFFAOYSA-N 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
Landscapes
- 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4201305.4 | 1992-01-20 | ||
| DE4201305A DE4201305A1 (de) | 1992-01-20 | 1992-01-20 | Thiophene und polythiophene, verfahren zu ihrer herstellung und ihre verwendung |
| DEP4206767.7 | 1992-03-04 | ||
| DE19924206767 DE4206767A1 (de) | 1992-03-04 | 1992-03-04 | Thiophene und polythiophene, verfahren zu ihrer herstellung und ihre verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2123324A1 true CA2123324A1 (en) | 1993-07-22 |
Family
ID=25911078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002123324A Abandoned CA2123324A1 (en) | 1992-01-20 | 1993-01-14 | Thiophenes and polythiophenes, their preparation and their use |
Country Status (10)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105340955A (zh) * | 2015-11-06 | 2016-02-24 | 南宁邃丛赋语科技开发有限责任公司 | 一种含噻呋酰胺和氯吡硫磷的农药组合物 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2577566A (en) * | 1947-12-13 | 1951-12-04 | Socony Vacuum Oil Co Inc | 3-thienyl thioethers |
| US3250787A (en) * | 1962-06-27 | 1966-05-10 | Dow Chemical Co | Alkylthio thiophenes |
| US4645777A (en) * | 1985-04-17 | 1987-02-24 | Fmc Corporation | Photoactive bithienyl pesticides |
-
1993
- 1993-01-14 EP EP93902185A patent/EP0624158A1/de not_active Withdrawn
- 1993-01-14 CA CA002123324A patent/CA2123324A1/en not_active Abandoned
- 1993-01-14 AU AU33494/93A patent/AU3349493A/en not_active Abandoned
- 1993-01-14 JP JP5512139A patent/JPH07502998A/ja active Pending
- 1993-01-14 HU HU9401351A patent/HUT67118A/hu unknown
- 1993-01-14 WO PCT/EP1993/000060 patent/WO1993014079A1/de not_active Application Discontinuation
- 1993-01-14 CZ CZ941553A patent/CZ155394A3/cs unknown
- 1993-01-15 IL IL104408A patent/IL104408A0/xx unknown
- 1993-01-20 TW TW082100354A patent/TW229138B/zh active
- 1993-01-20 MX MX9300282A patent/MX9300282A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU9401351D0 (en) | 1994-08-29 |
| TW229138B (enrdf_load_stackoverflow) | 1994-09-01 |
| AU3349493A (en) | 1993-08-03 |
| IL104408A0 (en) | 1993-05-13 |
| MX9300282A (es) | 1993-07-01 |
| CZ155394A3 (en) | 1995-02-15 |
| WO1993014079A1 (de) | 1993-07-22 |
| HUT67118A (en) | 1995-02-28 |
| EP0624158A1 (de) | 1994-11-17 |
| JPH07502998A (ja) | 1995-03-30 |
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