DD143424A5 - Verfahren zur herstellung von 1,1,1,3-tetrahalo-4-methylpentan - Google Patents
Verfahren zur herstellung von 1,1,1,3-tetrahalo-4-methylpentan Download PDFInfo
- Publication number
- DD143424A5 DD143424A5 DD77212565A DD21256577A DD143424A5 DD 143424 A5 DD143424 A5 DD 143424A5 DD 77212565 A DD77212565 A DD 77212565A DD 21256577 A DD21256577 A DD 21256577A DD 143424 A5 DD143424 A5 DD 143424A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- chloride
- methylpentane
- tetrahalo
- carbon atoms
- iron
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 4
- 239000010941 cobalt Substances 0.000 claims description 5
- 229910017052 cobalt Inorganic materials 0.000 claims description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 claims description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 4
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims description 4
- 150000001451 organic peroxides Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- 238000007259 addition reaction Methods 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 2
- 244000028419 Styrax benzoin Species 0.000 claims description 2
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 2
- 229960002130 benzoin Drugs 0.000 claims description 2
- 235000019382 gum benzoic Nutrition 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- 229910021577 Iron(II) chloride Inorganic materials 0.000 claims 2
- 229910052802 copper Inorganic materials 0.000 claims 2
- 239000010949 copper Substances 0.000 claims 2
- 230000003197 catalytic effect Effects 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 150000002978 peroxides Chemical class 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 239000002728 pyrethroid Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000003435 aroyl group Chemical group 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001589 carboacyl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 description 2
- -1 aliphatic peroxyacid Chemical class 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- 229960002089 ferrous chloride Drugs 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 229940070846 pyrethrins Drugs 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- NEPBEPYINQHTKZ-UHFFFAOYSA-N 1,1,1,3-tetrachloro-4-methylpentane Chemical compound CC(C)C(Cl)CC(Cl)(Cl)Cl NEPBEPYINQHTKZ-UHFFFAOYSA-N 0.000 description 1
- FAFHXIXTBUANJI-UHFFFAOYSA-N 1,1-dichloro-1,3-difluoro-4-methylpentane Chemical compound CC(C)C(F)CC(F)(Cl)Cl FAFHXIXTBUANJI-UHFFFAOYSA-N 0.000 description 1
- ROQHCMACHQVBCS-UHFFFAOYSA-N 3-bromo-1,1,1-trichloro-4-methylpentane Chemical compound CC(C)C(Br)CC(Cl)(Cl)Cl ROQHCMACHQVBCS-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 229940079721 copper chloride Drugs 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- WIWBLJMBLGWSIN-UHFFFAOYSA-L dichlorotris(triphenylphosphine)ruthenium(ii) Chemical compound [Cl-].[Cl-].[Ru+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 WIWBLJMBLGWSIN-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229940032296 ferric chloride Drugs 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- OTJIQLNMGDGAND-UHFFFAOYSA-N naphthalene-1,2,3,4,5,6-hexamine Chemical compound C1(=C(C(=C(C2=C(C(=CC=C12)N)N)N)N)N)N OTJIQLNMGDGAND-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 125000005634 peroxydicarbonate group Chemical group 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- GSNYHCYKJZVAMV-UHFFFAOYSA-N ruthenium(2+);triphenylphosphane Chemical class [Ru+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 GSNYHCYKJZVAMV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/19—Halogenated dienes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/275—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of hydrocarbons and halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74280176A | 1976-11-18 | 1976-11-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD143424A5 true DD143424A5 (de) | 1980-08-20 |
Family
ID=24986278
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD77212565A DD143424A5 (de) | 1976-11-18 | 1977-11-16 | Verfahren zur herstellung von 1,1,1,3-tetrahalo-4-methylpentan |
| DD77202110A DD134640A5 (de) | 1976-11-18 | 1977-11-16 | Verfahren zur herstellung von 1,1-dihalo-4-methyl-1,3-pentadien |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD77202110A DD134640A5 (de) | 1976-11-18 | 1977-11-16 | Verfahren zur herstellung von 1,1-dihalo-4-methyl-1,3-pentadien |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS5365805A (cs) |
| AU (1) | AU510041B2 (cs) |
| BE (1) | BE860826A (cs) |
| BR (1) | BR7707664A (cs) |
| CA (1) | CA1086778A (cs) |
| CS (1) | CS193596B2 (cs) |
| DD (2) | DD143424A5 (cs) |
| DE (1) | DE2751435A1 (cs) |
| DK (1) | DK508377A (cs) |
| ES (1) | ES464267A1 (cs) |
| FR (1) | FR2371402A1 (cs) |
| GB (1) | GB1540198A (cs) |
| HU (1) | HU175532B (cs) |
| IL (1) | IL53408A (cs) |
| IN (1) | IN146116B (cs) |
| NL (1) | NL7712680A (cs) |
| PL (1) | PL106098B1 (cs) |
| RO (1) | RO76301A (cs) |
| SU (1) | SU843731A3 (cs) |
| ZA (1) | ZA776871B (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0196088A1 (de) * | 1985-03-27 | 1986-10-01 | Wacker-Chemie GmbH | Verfahren zur Herstellung von Verbindungen mit mehrfach durch Chlor substituiertem Alkylrest |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8586804B2 (en) * | 2010-12-01 | 2013-11-19 | E. I. Du Pont De Nemours And Company | Synthesis of 1,1,3-trichloro-1-propene |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2410541A (en) * | 1942-04-10 | 1946-11-05 | Du Pont | Polyhalogenated olefins |
| NL70108C (cs) * | 1949-12-30 | |||
| US3299152A (en) * | 1961-11-06 | 1967-01-17 | Toyo Koatsu Ind Inc | Preparation of alpha, omegadichloroolefin |
| GB1536685A (en) * | 1975-06-02 | 1978-12-20 | Shell Int Research | Process for the preparation of 1,1-dihalo-1,3-dienes |
-
1977
- 1977-10-27 CA CA289,709A patent/CA1086778A/en not_active Expired
- 1977-11-12 JP JP13525377A patent/JPS5365805A/ja active Pending
- 1977-11-14 CS CS777459A patent/CS193596B2/cs unknown
- 1977-11-15 RO RO7792125A patent/RO76301A/ro unknown
- 1977-11-16 DD DD77212565A patent/DD143424A5/de unknown
- 1977-11-16 DK DK508377A patent/DK508377A/da not_active Application Discontinuation
- 1977-11-16 BE BE2056427A patent/BE860826A/xx unknown
- 1977-11-16 FR FR7734439A patent/FR2371402A1/fr not_active Withdrawn
- 1977-11-16 DD DD77202110A patent/DD134640A5/xx unknown
- 1977-11-16 HU HU77SA3072A patent/HU175532B/hu unknown
- 1977-11-16 IL IL53408A patent/IL53408A/xx unknown
- 1977-11-16 GB GB47657/77A patent/GB1540198A/en not_active Expired
- 1977-11-17 BR BR7707664A patent/BR7707664A/pt unknown
- 1977-11-17 IN IN1619/CAL/77A patent/IN146116B/en unknown
- 1977-11-17 NL NL7712680A patent/NL7712680A/xx not_active Application Discontinuation
- 1977-11-17 AU AU30734/77A patent/AU510041B2/en not_active Expired
- 1977-11-17 ZA ZA00776871A patent/ZA776871B/xx unknown
- 1977-11-17 DE DE19772751435 patent/DE2751435A1/de not_active Withdrawn
- 1977-11-18 ES ES464267A patent/ES464267A1/es not_active Expired
- 1977-11-18 SU SU772544102A patent/SU843731A3/ru active
- 1977-11-18 PL PL1977202246A patent/PL106098B1/pl unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0196088A1 (de) * | 1985-03-27 | 1986-10-01 | Wacker-Chemie GmbH | Verfahren zur Herstellung von Verbindungen mit mehrfach durch Chlor substituiertem Alkylrest |
Also Published As
| Publication number | Publication date |
|---|---|
| HU175532B (hu) | 1980-08-28 |
| JPS5365805A (en) | 1978-06-12 |
| CS193596B2 (en) | 1979-10-31 |
| PL106098B1 (pl) | 1979-11-30 |
| DK508377A (da) | 1978-05-19 |
| SU843731A3 (ru) | 1981-06-30 |
| BE860826A (nl) | 1978-05-16 |
| ES464267A1 (es) | 1978-08-01 |
| IN146116B (cs) | 1979-02-24 |
| DD134640A5 (de) | 1979-03-14 |
| PL202246A1 (pl) | 1978-07-31 |
| AU510041B2 (en) | 1980-06-05 |
| FR2371402A1 (fr) | 1978-06-16 |
| DE2751435A1 (de) | 1978-05-24 |
| IL53408A (en) | 1981-02-27 |
| BR7707664A (pt) | 1978-06-13 |
| IL53408A0 (en) | 1978-01-31 |
| NL7712680A (nl) | 1978-05-22 |
| GB1540198A (en) | 1979-02-07 |
| ZA776871B (en) | 1978-09-27 |
| CA1086778A (en) | 1980-09-30 |
| AU3073477A (en) | 1979-05-24 |
| RO76301A (ro) | 1981-11-04 |
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