DD159544A5 - Verfahren zur herstellung von benzimidazolinsalzen - Google Patents
Verfahren zur herstellung von benzimidazolinsalzen Download PDFInfo
- Publication number
- DD159544A5 DD159544A5 DD80226588A DD22658880A DD159544A5 DD 159544 A5 DD159544 A5 DD 159544A5 DD 80226588 A DD80226588 A DD 80226588A DD 22658880 A DD22658880 A DD 22658880A DD 159544 A5 DD159544 A5 DD 159544A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- fly
- trifluoromethyl
- larvae
- house
- nitro
- Prior art date
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- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 238000000034 method Methods 0.000 claims abstract description 20
- 238000002360 preparation method Methods 0.000 claims abstract description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 150000001556 benzimidazoles Chemical class 0.000 claims description 7
- 150000001412 amines Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- DYUHVQLOFZJMNI-UHFFFAOYSA-N FC(C(F)F)(F)C=1NC2=C(N1)C=C(C=C2[N+](=O)[O-])C(F)(F)F.[Na] Chemical compound FC(C(F)F)(F)C=1NC2=C(N1)C=C(C=C2[N+](=O)[O-])C(F)(F)F.[Na] DYUHVQLOFZJMNI-UHFFFAOYSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 66
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241001414987 Strepsiptera Species 0.000 description 1
- 241001584775 Tunga penetrans Species 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 244000000054 animal parasite Species 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 150000003974 aralkylamines Chemical class 0.000 description 1
- MXMZCLLIUQEKSN-UHFFFAOYSA-N benzimidazoline Chemical compound C1=CC=C2NCNC2=C1 MXMZCLLIUQEKSN-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910001622 calcium bromide Inorganic materials 0.000 description 1
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000009193 crawling Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 239000013057 ectoparasiticide Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000010006 flight Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000021331 green beans Nutrition 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000013383 initial experiment Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 230000033001 locomotion Effects 0.000 description 1
- 210000004705 lumbosacral region Anatomy 0.000 description 1
- 229960000453 malathion Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/26—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/106,990 US4265901A (en) | 1979-12-26 | 1979-12-26 | 2-Oxybenzimidazoline compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD159544A5 true DD159544A5 (de) | 1983-03-16 |
Family
ID=22314286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80226588A DD159544A5 (de) | 1979-12-26 | 1980-12-23 | Verfahren zur herstellung von benzimidazolinsalzen |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4265901A (es) |
| EP (1) | EP0031699A1 (es) |
| JP (1) | JPS56108771A (es) |
| KR (1) | KR840001051B1 (es) |
| AR (1) | AR225482A1 (es) |
| AT (1) | AT375929B (es) |
| AU (1) | AU6539980A (es) |
| BE (1) | BE886728A (es) |
| BR (1) | BR8008506A (es) |
| CA (1) | CA1156243A (es) |
| CS (1) | CS216238B2 (es) |
| DD (1) | DD159544A5 (es) |
| DK (1) | DK542480A (es) |
| ES (1) | ES8301222A1 (es) |
| FR (1) | FR2472566A1 (es) |
| GB (1) | GB2066248B (es) |
| GR (1) | GR72300B (es) |
| IL (1) | IL61707A (es) |
| IT (1) | IT1193393B (es) |
| NZ (1) | NZ195835A (es) |
| OA (1) | OA06672A (es) |
| PT (1) | PT72204B (es) |
| RO (1) | RO81209A (es) |
| YU (1) | YU323980A (es) |
| ZA (1) | ZA807948B (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4421759A (en) * | 1981-07-27 | 1983-12-20 | Eli Lilly And Company | Methods for controlling fire ants |
| EP0113945A1 (en) * | 1983-01-19 | 1984-07-25 | Eli Lilly And Company | Amine salts |
| US5331003A (en) * | 1993-03-26 | 1994-07-19 | Eli Lilly And Company | Anticoccidial methods |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE20508E (en) | 1937-09-14 | Selective clutch mechanism | ||
| US3705174A (en) * | 1970-02-27 | 1972-12-05 | Merck & Co Inc | Polyhaloalkyl benzimidazoles |
| US3813407A (en) * | 1970-03-19 | 1974-05-28 | Lilly Co Eli | Process for the preparation of 1-hydroxy-2-(1,1-difluoroalkyl)benzimidazoles and 1-hydroxy-2-(1,1-difluoroalkyl)-1h-imidazo(4,5-b)pyridines |
| ZA718532B (en) * | 1970-12-28 | 1973-08-29 | Lilly Co Eli | A process for rearrangement or reduction of 1-derivatives of 1-hydroxybenzimidazoles and 1-hydroxyimidazo(4,5-b)pyriines |
| US3875173A (en) * | 1970-12-28 | 1975-04-01 | Lilly Co Eli | Method for introducing halogen into benzimidazole and imidazopyridine compounds |
| US4122184A (en) * | 1973-09-14 | 1978-10-24 | Eli Lilly And Company | Benzimidazole insecticides |
| US3980784A (en) * | 1974-12-02 | 1976-09-14 | Eli Lilly And Company | Control of animal parasites with benzimidazoles |
| FR2312495A1 (fr) * | 1975-05-27 | 1976-12-24 | Lilly Co Eli | Esters ou ethers de 1-hydroxy-2(1,1-difluoroalkyl)-benzimidazoles pesticides |
| US3989840A (en) * | 1975-07-18 | 1976-11-02 | Eli Lilly And Company | Control of animal parasites with ring-substituted N-(2,2-difluoroalkanoyl)-O-phenylenediamines |
-
1979
- 1979-12-26 US US06/106,990 patent/US4265901A/en not_active Expired - Lifetime
-
1980
- 1980-12-15 NZ NZ195835A patent/NZ195835A/xx unknown
- 1980-12-15 AT AT0609280A patent/AT375929B/de not_active IP Right Cessation
- 1980-12-15 AU AU65399/80A patent/AU6539980A/en not_active Abandoned
- 1980-12-15 IL IL61707A patent/IL61707A/xx unknown
- 1980-12-15 CA CA000366783A patent/CA1156243A/en not_active Expired
- 1980-12-16 PT PT72204A patent/PT72204B/pt unknown
- 1980-12-17 FR FR8026804A patent/FR2472566A1/fr active Granted
- 1980-12-18 BE BE1/10081A patent/BE886728A/fr not_active IP Right Cessation
- 1980-12-18 CS CS809021A patent/CS216238B2/cs unknown
- 1980-12-19 GR GR63725A patent/GR72300B/el unknown
- 1980-12-19 EP EP80304645A patent/EP0031699A1/en not_active Ceased
- 1980-12-19 ES ES498009A patent/ES8301222A1/es not_active Expired
- 1980-12-19 GB GB8040730A patent/GB2066248B/en not_active Expired
- 1980-12-19 ZA ZA00807948A patent/ZA807948B/xx unknown
- 1980-12-19 DK DK542480A patent/DK542480A/da not_active Application Discontinuation
- 1980-12-22 YU YU03239/80A patent/YU323980A/xx unknown
- 1980-12-22 RO RO80102914A patent/RO81209A/ro unknown
- 1980-12-23 DD DD80226588A patent/DD159544A5/de unknown
- 1980-12-23 AR AR283772A patent/AR225482A1/es active
- 1980-12-23 IT IT26935/80A patent/IT1193393B/it active
- 1980-12-23 BR BR8008506A patent/BR8008506A/pt unknown
- 1980-12-24 KR KR1019800004921A patent/KR840001051B1/ko active
- 1980-12-25 JP JP18940580A patent/JPS56108771A/ja active Pending
- 1980-12-26 OA OA57285A patent/OA06672A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES498009A0 (es) | 1982-12-01 |
| GR72300B (es) | 1983-10-18 |
| ZA807948B (en) | 1982-07-28 |
| OA06672A (fr) | 1981-09-30 |
| AU6539980A (en) | 1981-07-02 |
| RO81209A (ro) | 1983-02-01 |
| ATA609280A (de) | 1984-02-15 |
| BR8008506A (pt) | 1981-07-21 |
| CS216238B2 (en) | 1982-10-29 |
| IT8026935A0 (it) | 1980-12-23 |
| JPS56108771A (en) | 1981-08-28 |
| BE886728A (fr) | 1981-06-18 |
| FR2472566A1 (fr) | 1981-07-03 |
| GB2066248B (en) | 1984-05-23 |
| DK542480A (da) | 1981-06-27 |
| PT72204A (en) | 1981-01-01 |
| AR225482A1 (es) | 1982-03-31 |
| RO81209B (ro) | 1983-01-30 |
| FR2472566B1 (es) | 1983-03-18 |
| KR840001051B1 (ko) | 1984-07-27 |
| AT375929B (de) | 1984-09-25 |
| EP0031699A1 (en) | 1981-07-08 |
| CA1156243A (en) | 1983-11-01 |
| IL61707A (en) | 1984-05-31 |
| PT72204B (en) | 1981-10-28 |
| KR830004262A (ko) | 1983-07-09 |
| NZ195835A (en) | 1983-09-30 |
| ES8301222A1 (es) | 1982-12-01 |
| YU323980A (en) | 1983-09-30 |
| IL61707A0 (en) | 1981-01-30 |
| US4265901A (en) | 1981-05-05 |
| GB2066248A (en) | 1981-07-08 |
| IT1193393B (it) | 1988-06-15 |
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