CA1125655A - Amidoamine toxicants - Google Patents
Amidoamine toxicantsInfo
- Publication number
- CA1125655A CA1125655A CA345,776A CA345776A CA1125655A CA 1125655 A CA1125655 A CA 1125655A CA 345776 A CA345776 A CA 345776A CA 1125655 A CA1125655 A CA 1125655A
- Authority
- CA
- Canada
- Prior art keywords
- amidoamine
- dimethylamine
- composition
- activity
- oleamidopropyl
- 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
- 239000003440 toxic substance Substances 0.000 title claims abstract description 26
- 231100000167 toxic agent Toxicity 0.000 title claims description 24
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims abstract description 13
- 241001124076 Aphididae Species 0.000 claims abstract description 9
- 244000078703 ectoparasite Species 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 27
- UCWYGNTYSWIDSW-QXMHVHEDSA-N (z)-n-[3-(dimethylamino)propyl]octadec-9-enamide Chemical group CCCCCCCC\C=C/CCCCCCCC(=O)NCCCN(C)C UCWYGNTYSWIDSW-QXMHVHEDSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 239000003937 drug carrier Substances 0.000 claims description 6
- TWMFGCHRALXDAR-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]dodecanamide Chemical compound CCCCCCCCCCCC(=O)NCCCN(C)C TWMFGCHRALXDAR-UHFFFAOYSA-N 0.000 claims description 6
- 241000256113 Culicidae Species 0.000 claims description 5
- 230000000974 larvacidal effect Effects 0.000 claims description 4
- 241000238631 Hexapoda Species 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 2
- 231100000331 toxic Toxicity 0.000 claims description 2
- 230000002588 toxic effect Effects 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 4
- 230000006872 improvement Effects 0.000 claims 1
- 230000000749 insecticidal effect Effects 0.000 claims 1
- 241000255925 Diptera Species 0.000 abstract description 5
- 239000007921 spray Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 210000004681 ovum Anatomy 0.000 description 8
- 230000003038 pediculicidal effect Effects 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 230000003151 ovacidal effect Effects 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 5
- 235000013601 eggs Nutrition 0.000 description 5
- 230000003129 miticidal effect Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241001674048 Phthiraptera Species 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 239000003595 mist Substances 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000994 depressogenic effect Effects 0.000 description 3
- 229940008099 dimethicone Drugs 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 231100000194 ovacidal Toxicity 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 239000002453 shampoo Substances 0.000 description 3
- 239000008399 tap water Substances 0.000 description 3
- 235000020679 tap water Nutrition 0.000 description 3
- DWIUBTKCNCCGOO-QOYCNBSOSA-N (z,12r)-n-[3-(dimethylamino)propyl]-12-hydroxyoctadec-9-enamide Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)NCCCN(C)C DWIUBTKCNCCGOO-QOYCNBSOSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 241000238876 Acari Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000517306 Pediculus humanus corporis Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000002824 aphicidal effect Effects 0.000 description 2
- 150000004656 dimethylamines Chemical class 0.000 description 2
- 239000013057 ectoparasiticide Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 description 2
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N gamma-hexachlorocyclohexane Natural products ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- 229960002809 lindane Drugs 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- -1 methylamine Isopropyl Myristate Chemical compound 0.000 description 2
- XNJXGLWSAVUJRR-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCN(C)C XNJXGLWSAVUJRR-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 231100000816 toxic dose Toxicity 0.000 description 2
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- 206010063409 Acarodermatitis Diseases 0.000 description 1
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical group C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 1
- 241000256118 Aedes aegypti Species 0.000 description 1
- 241000398201 Bryobia praetiosa Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 241000721714 Macrosiphum euphorbiae Species 0.000 description 1
- 239000005949 Malathion Substances 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 241000620638 Psoroptes cuniculi Species 0.000 description 1
- 241000447727 Scabies Species 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 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 1
- ZXQYGBMAQZUVMI-QQDHXZELSA-N [cyano-(3-phenoxyphenyl)methyl] (1r,3r)-3-[(z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@@H](\C=C(/Cl)C(F)(F)F)[C@H]1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-QQDHXZELSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- SVOAENZIOKPANY-CVBJKYQLSA-L copper;(z)-octadec-9-enoate Chemical compound [Cu+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O SVOAENZIOKPANY-CVBJKYQLSA-L 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001627 detrimental 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
- 230000003467 diminishing effect Effects 0.000 description 1
- 230000001984 ectoparasiticidal effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960000453 malathion Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- NVDGQURQMZAKIA-UHFFFAOYSA-N n-(4-amino-3-hydroxybutyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCC(O)CN NVDGQURQMZAKIA-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- 229940070846 pyrethrins Drugs 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 208000005687 scabies Diseases 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pest Control & Pesticides (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Agronomy & Crop Science (AREA)
- General Chemical & Material Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1256879A | 1979-02-15 | 1979-02-15 | |
| US12,568 | 1979-02-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1125655A true CA1125655A (en) | 1982-06-15 |
Family
ID=21755581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA345,776A Expired CA1125655A (en) | 1979-02-15 | 1980-02-15 | Amidoamine toxicants |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS55113703A (en, 2012) |
| AU (1) | AU534416B2 (en, 2012) |
| BE (1) | BE881727A (en, 2012) |
| CA (1) | CA1125655A (en, 2012) |
| CH (1) | CH646581A5 (en, 2012) |
| DE (1) | DE3005380A1 (en, 2012) |
| FR (1) | FR2448859A1 (en, 2012) |
| GB (1) | GB2044100B (en, 2012) |
| MX (1) | MX7016E (en, 2012) |
| PH (1) | PH18347A (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3708033A1 (de) * | 1987-03-12 | 1988-09-22 | Bayer Ag | Mittel zur insekten- und milbenabwehr |
| DE19953274A1 (de) * | 1999-11-05 | 2001-05-10 | Cognis Deutschland Gmbh | Emulsionen |
| EP2378884A2 (en) * | 2009-01-22 | 2011-10-26 | Laboratorios Miret, S.A. | Use of cationic surfactants as acaricidal agents |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1968341A (en) * | 1930-06-21 | 1934-07-31 | Chem Ind Basel | Agents for combating pests and in a process of applying same |
| FR1128487A (fr) * | 1954-04-05 | 1957-01-07 | Shell Res Ltd | Compositions insecticides et fongidices |
| US3145137A (en) * | 1961-05-12 | 1964-08-18 | Monsanto Co | Alkanoylamidoalkyleneamines and their quaternary ammonium salts as fungicides |
| DE2338386B1 (de) * | 1973-07-28 | 1974-09-05 | Schuelke & Mayr Gmbh | Handwasch- und -desinfektionsmittel |
-
1980
- 1980-02-05 PH PH23593A patent/PH18347A/en unknown
- 1980-02-11 CH CH108680A patent/CH646581A5/de not_active IP Right Cessation
- 1980-02-13 DE DE19803005380 patent/DE3005380A1/de not_active Withdrawn
- 1980-02-14 FR FR8003251A patent/FR2448859A1/fr active Granted
- 1980-02-14 BE BE0/199404A patent/BE881727A/fr not_active IP Right Cessation
- 1980-02-15 GB GB8005158A patent/GB2044100B/en not_active Expired
- 1980-02-15 JP JP1769380A patent/JPS55113703A/ja active Granted
- 1980-02-15 CA CA345,776A patent/CA1125655A/en not_active Expired
- 1980-02-15 AU AU55580/80A patent/AU534416B2/en not_active Ceased
- 1980-02-15 MX MX808648U patent/MX7016E/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0114203B2 (en, 2012) | 1989-03-10 |
| PH18347A (en) | 1985-06-05 |
| MX7016E (es) | 1987-02-11 |
| AU534416B2 (en) | 1984-01-26 |
| AU5558080A (en) | 1980-08-21 |
| JPS55113703A (en) | 1980-09-02 |
| FR2448859A1 (fr) | 1980-09-12 |
| BE881727A (fr) | 1980-08-14 |
| GB2044100A (en) | 1980-10-15 |
| FR2448859B1 (en, 2012) | 1983-02-18 |
| GB2044100B (en) | 1983-10-26 |
| DE3005380A1 (de) | 1980-08-28 |
| CH646581A5 (de) | 1984-12-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |