DE2020561A1 - Alkylaralkyl-2,2-dichlorvinylphosphate,Verfahren zu ihrer Herstellung und ihre Verwendung als anthelmintica - Google Patents
Alkylaralkyl-2,2-dichlorvinylphosphate,Verfahren zu ihrer Herstellung und ihre Verwendung als anthelminticaInfo
- Publication number
- DE2020561A1 DE2020561A1 DE19702020561 DE2020561A DE2020561A1 DE 2020561 A1 DE2020561 A1 DE 2020561A1 DE 19702020561 DE19702020561 DE 19702020561 DE 2020561 A DE2020561 A DE 2020561A DE 2020561 A1 DE2020561 A1 DE 2020561A1
- Authority
- DE
- Germany
- Prior art keywords
- dichlorovinyl
- methyl
- phosphate
- dichlorovinyl phosphate
- group
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 9
- 229910019142 PO4 Inorganic materials 0.000 title claims description 5
- 125000000217 alkyl group Chemical group 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 235000021317 phosphate Nutrition 0.000 title description 4
- 150000003013 phosphoric acid derivatives Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 28
- -1 methyl - Chemical class 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052739 hydrogen Chemical group 0.000 claims description 6
- 239000001257 hydrogen Chemical group 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- BPNLLIHZSAFABG-UHFFFAOYSA-N [hydroxy(methoxy)phosphoryl] methyl hydrogen phosphate Chemical compound COP(O)(=O)OP(O)(=O)OC BPNLLIHZSAFABG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- IRZIMCQXZSILPU-UHFFFAOYSA-N 1-(4-fluorophenyl)butan-1-ol Chemical compound CCCC(O)C1=CC=C(F)C=C1 IRZIMCQXZSILPU-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000005622 butynylene group Chemical group 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 241001465754 Metazoa Species 0.000 description 21
- 230000000507 anthelmentic effect Effects 0.000 description 16
- 229940124339 anthelmintic agent Drugs 0.000 description 8
- 239000000921 anthelmintic agent Substances 0.000 description 8
- 244000045947 parasite Species 0.000 description 8
- 244000079386 endoparasite Species 0.000 description 7
- 231100001274 therapeutic index Toxicity 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 241000894007 species Species 0.000 description 5
- 241000242722 Cestoda Species 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 206010061217 Infestation Diseases 0.000 description 3
- 241000244206 Nematoda Species 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000272517 Anseriformes Species 0.000 description 2
- 241000271566 Aves Species 0.000 description 2
- 241001126268 Cooperia Species 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000975692 Syphacia obvelata Species 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 235000011180 diphosphates Nutrition 0.000 description 2
- BNKAXGCRDYRABM-UHFFFAOYSA-N ethenyl dihydrogen phosphate Chemical class OP(O)(=O)OC=C BNKAXGCRDYRABM-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 231100000817 safety factor Toxicity 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- MNRWIFMPVCLIDS-UHFFFAOYSA-N 2,2-dichloroethenyl dihydrogen phosphate Chemical compound OP(O)(=O)OC=C(Cl)Cl MNRWIFMPVCLIDS-UHFFFAOYSA-N 0.000 description 1
- UIXDXDYFMWTCEQ-UHFFFAOYSA-N 4-(4-chlorophenyl)butan-1-ol Chemical compound OCCCCC1=CC=C(Cl)C=C1 UIXDXDYFMWTCEQ-UHFFFAOYSA-N 0.000 description 1
- SFWCSEDMBWCHQL-UHFFFAOYSA-N 4-(4-fluorophenyl)butan-1-ol Chemical compound OCCCCC1=CC=C(F)C=C1 SFWCSEDMBWCHQL-UHFFFAOYSA-N 0.000 description 1
- LDZLXQFDGRCELX-UHFFFAOYSA-N 4-phenylbutan-1-ol Chemical compound OCCCCC1=CC=CC=C1 LDZLXQFDGRCELX-UHFFFAOYSA-N 0.000 description 1
- 241001147657 Ancylostoma Species 0.000 description 1
- 241001465677 Ancylostomatoidea Species 0.000 description 1
- 241001626718 Anoplocephala Species 0.000 description 1
- 241000244186 Ascaris Species 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000282421 Canidae Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001137876 Diphyllobothrium Species 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241000244160 Echinococcus Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241001660203 Gasterophilus Species 0.000 description 1
- 241000243976 Haemonchus Species 0.000 description 1
- 241000404582 Hymenolepis <angiosperm> Species 0.000 description 1
- 241000520690 Mesocestoides Species 0.000 description 1
- 241000498271 Necator Species 0.000 description 1
- 241001466061 Nematomorpha Species 0.000 description 1
- 241000257191 Oestridae Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000243795 Ostertagia Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 241000975704 Syphacia Species 0.000 description 1
- 241000255628 Tabanidae Species 0.000 description 1
- 241000244155 Taenia Species 0.000 description 1
- 241000243797 Trichostrongylus Species 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000003975 animal breeding Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000009313 farming Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 238000009374 poultry farming Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/113—Esters of phosphoric acids with unsaturated acyclic alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81997869A | 1969-04-28 | 1969-04-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2020561A1 true DE2020561A1 (de) | 1970-10-29 |
Family
ID=25229578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702020561 Pending DE2020561A1 (de) | 1969-04-28 | 1970-04-27 | Alkylaralkyl-2,2-dichlorvinylphosphate,Verfahren zu ihrer Herstellung und ihre Verwendung als anthelmintica |
Country Status (6)
| Country | Link |
|---|---|
| CH (1) | CH524639A (enrdf_load_stackoverflow) |
| DE (1) | DE2020561A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2051498B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1288445A (enrdf_load_stackoverflow) |
| NL (1) | NL7006074A (enrdf_load_stackoverflow) |
| ZA (1) | ZA702787B (enrdf_load_stackoverflow) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1251745B (enrdf_load_stackoverflow) * | 1965-11-17 | 1967-10-12 |
-
1970
- 1970-04-27 FR FR707015269A patent/FR2051498B1/fr not_active Expired
- 1970-04-27 GB GB2002870A patent/GB1288445A/en not_active Expired
- 1970-04-27 DE DE19702020561 patent/DE2020561A1/de active Pending
- 1970-04-27 NL NL7006074A patent/NL7006074A/xx unknown
- 1970-04-27 CH CH628570A patent/CH524639A/de not_active IP Right Cessation
- 1970-04-27 ZA ZA702787A patent/ZA702787B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA702787B (en) | 1971-01-27 |
| FR2051498B1 (enrdf_load_stackoverflow) | 1973-08-10 |
| CH524639A (de) | 1972-06-30 |
| FR2051498A1 (enrdf_load_stackoverflow) | 1971-04-09 |
| GB1288445A (enrdf_load_stackoverflow) | 1972-09-06 |
| NL7006074A (enrdf_load_stackoverflow) | 1970-10-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |