DE2637863C2 - - Google Patents
Info
- Publication number
- DE2637863C2 DE2637863C2 DE2637863A DE2637863A DE2637863C2 DE 2637863 C2 DE2637863 C2 DE 2637863C2 DE 2637863 A DE2637863 A DE 2637863A DE 2637863 A DE2637863 A DE 2637863A DE 2637863 C2 DE2637863 C2 DE 2637863C2
- Authority
- DE
- Germany
- Prior art keywords
- copolymer
- styrene
- maleic anhydride
- hydrolyzed
- active ingredient
- 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.)
- Expired
Links
- 229920001577 copolymer Polymers 0.000 claims description 63
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 43
- 239000004480 active ingredient Substances 0.000 claims description 38
- 239000003795 chemical substances by application Substances 0.000 claims description 36
- 241001465754 Metazoa Species 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 21
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 20
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 19
- 239000002245 particle Substances 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 7
- 244000045947 parasite Species 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000011872 intimate mixture Substances 0.000 claims description 2
- 230000002522 swelling effect Effects 0.000 claims 1
- WOLATMHLPFJRGC-UHFFFAOYSA-N furan-2,5-dione;styrene Chemical compound O=C1OC(=O)C=C1.C=CC1=CC=CC=C1 WOLATMHLPFJRGC-UHFFFAOYSA-N 0.000 description 23
- 239000004800 polyvinyl chloride Substances 0.000 description 16
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 229950001327 dichlorvos Drugs 0.000 description 11
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 11
- 229920006385 Geon Polymers 0.000 description 10
- 210000001035 gastrointestinal tract Anatomy 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- 239000003381 stabilizer Substances 0.000 description 9
- 229940079593 drug Drugs 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- 239000011976 maleic acid Substances 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
- 241000282887 Suidae Species 0.000 description 4
- -1 chlorovinyl-O Chemical group 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 210000003608 fece Anatomy 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000283690 Bos taurus Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 244000079386 endoparasite Species 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 210000004051 gastric juice Anatomy 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 230000002141 anti-parasite Effects 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003754 fetus Anatomy 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000005661 hydrophobic surface Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000002267 larvicidal agent Substances 0.000 description 1
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001447 polyvinyl benzene Polymers 0.000 description 1
- 229920001291 polyvinyl halide Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920006214 polyvinylidene halide Polymers 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5026—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
Landscapes
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60739775A | 1975-08-25 | 1975-08-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2637863A1 DE2637863A1 (de) | 1977-03-10 |
| DE2637863C2 true DE2637863C2 (en:Method) | 1988-07-21 |
Family
ID=24432093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762637863 Granted DE2637863A1 (de) | 1975-08-25 | 1976-08-23 | Mittel zur bekaempfung von parasiten bei warmbluetlern und verfahren zu ihrer herstellung |
Country Status (9)
| Country | Link |
|---|---|
| AU (1) | AU503471B2 (en:Method) |
| BE (1) | BE845365A (en:Method) |
| DE (1) | DE2637863A1 (en:Method) |
| DK (1) | DK379076A (en:Method) |
| FR (1) | FR2321895A1 (en:Method) |
| GB (1) | GB1521938A (en:Method) |
| NL (1) | NL7609333A (en:Method) |
| SE (1) | SE7609307L (en:Method) |
| ZA (1) | ZA765043B (en:Method) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8805286D0 (en) * | 1988-03-05 | 1988-04-07 | Schering Agrochemicals Ltd | Trypanocides |
| RU2135187C1 (ru) * | 1996-04-26 | 1999-08-27 | Уфимский научно-исследовательский институт глазных болезней | Средство для лечения герпетического кератита |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1249823B (en:Method) * | 1964-01-15 | 1967-09-14 | ||
| US3553322A (en) * | 1967-07-21 | 1971-01-05 | Shell Oil Co | Helminth control |
| US3507956A (en) * | 1967-12-27 | 1970-04-21 | Shell Oil Co | Treatment of young animals with dialkyl beta-chlorovinyl phosphate |
| DE1767425B2 (de) * | 1968-05-09 | 1973-05-17 | R P Scherer GmbH, 6930 Eberbach | Verfahren zur herstellung von magensaftresistenten gelatinekapseln |
| FR2119860A1 (en) * | 1970-12-29 | 1972-08-11 | Aries Robert | Organophosphorus pesticides - stabilized by opt substd hydroxyanthraquinones |
| FR2123142A3 (en) * | 1971-01-25 | 1972-09-08 | Aries Robert | Pesticidal organophosphorus compsns - stabilized by 2-vinyl imidazolines and 2-vinylpyrimidines |
| US3937825A (en) * | 1973-09-21 | 1976-02-10 | American Cyanamid Company | Anthelmintic composition and method of use |
-
1976
- 1976-08-20 BE BE1007570A patent/BE845365A/xx unknown
- 1976-08-23 DE DE19762637863 patent/DE2637863A1/de active Granted
- 1976-08-23 ZA ZA765043A patent/ZA765043B/xx unknown
- 1976-08-23 AU AU17054/76A patent/AU503471B2/en not_active Expired
- 1976-08-23 SE SE7609307A patent/SE7609307L/xx unknown
- 1976-08-23 DK DK379076A patent/DK379076A/da unknown
- 1976-08-23 GB GB34984/76A patent/GB1521938A/en not_active Expired
- 1976-08-23 NL NL7609333A patent/NL7609333A/xx unknown
- 1976-08-23 FR FR7625481A patent/FR2321895A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| BE845365A (nl) | 1977-02-21 |
| FR2321895A1 (fr) | 1977-03-25 |
| NL7609333A (nl) | 1977-03-01 |
| FR2321895B1 (en:Method) | 1978-12-22 |
| DE2637863A1 (de) | 1977-03-10 |
| GB1521938A (en) | 1978-08-16 |
| SE7609307L (sv) | 1977-02-26 |
| AU503471B2 (en) | 1979-09-06 |
| DK379076A (da) | 1977-02-26 |
| ZA765043B (en) | 1977-08-31 |
| AU1705476A (en) | 1978-03-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |