GB1592699A - 2-anilinomethyl-2-imidazoline compounds and a method of combatting ectoparasites using them - Google Patents
2-anilinomethyl-2-imidazoline compounds and a method of combatting ectoparasites using them Download PDFInfo
- Publication number
- GB1592699A GB1592699A GB47367/77A GB4736777A GB1592699A GB 1592699 A GB1592699 A GB 1592699A GB 47367/77 A GB47367/77 A GB 47367/77A GB 4736777 A GB4736777 A GB 4736777A GB 1592699 A GB1592699 A GB 1592699A
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- Prior art keywords
- compound
- alkyl
- compounds
- formula
- carbon atoms
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 22
- 244000078703 ectoparasite Species 0.000 title description 3
- FPZTYKLEJPXTKD-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-ylmethyl)aniline Chemical class N=1CCNC=1CNC1=CC=CC=C1 FPZTYKLEJPXTKD-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 241000238876 Acari Species 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- -1 dimethylanilinomethyl Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000008187 granular material Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 5
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 230000001984 ectoparasiticidal effect Effects 0.000 claims description 4
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
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- 239000000428 dust Substances 0.000 claims description 3
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
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- 150000002431 hydrogen Chemical class 0.000 claims 1
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- 238000007792 addition Methods 0.000 description 10
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- 230000000694 effects Effects 0.000 description 7
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- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 4
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
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- JLRGGNFHZLXKOR-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-ylmethyl)-2,3-dimethylaniline;hydrochloride Chemical compound Cl.CC1=CC=CC(NCC=2NCCN=2)=C1C JLRGGNFHZLXKOR-UHFFFAOYSA-N 0.000 description 3
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- YZNYRQMEBVFFHW-UHFFFAOYSA-N 2,3-dichloro-n-(4,5-dihydro-1h-imidazol-2-ylmethyl)aniline;hydrochloride Chemical compound Cl.ClC1=CC=CC(NCC=2NCCN=2)=C1Cl YZNYRQMEBVFFHW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
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- 241001465754 Metazoa Species 0.000 description 2
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- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
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- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- OEJNXTAZZBRGDN-UHFFFAOYSA-N toxaphene Chemical compound ClC1C(Cl)C2(Cl)C(CCl)(CCl)C(=C)C1(Cl)C2(Cl)Cl OEJNXTAZZBRGDN-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1440176 | 1976-11-16 | ||
| CH1440276 | 1976-11-16 | ||
| CH1239077A CH630507A5 (en) | 1977-10-11 | 1977-10-11 | Pesticides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1592699A true GB1592699A (en) | 1981-07-08 |
Family
ID=27176829
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB47367/77A Expired GB1592699A (en) | 1976-11-16 | 1977-11-14 | 2-anilinomethyl-2-imidazoline compounds and a method of combatting ectoparasites using them |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4254133A (enExample) |
| JP (1) | JPS5363378A (enExample) |
| AR (1) | AR216660A1 (enExample) |
| BR (1) | BR7707589A (enExample) |
| CA (1) | CA1104143A (enExample) |
| DE (1) | DE2750902A1 (enExample) |
| EG (1) | EG12913A (enExample) |
| ES (1) | ES464150A1 (enExample) |
| FR (2) | FR2380733A1 (enExample) |
| GB (1) | GB1592699A (enExample) |
| IL (1) | IL53374A (enExample) |
| IT (1) | IT1143778B (enExample) |
| MX (1) | MX5135E (enExample) |
| NL (1) | NL7712401A (enExample) |
| NZ (1) | NZ185685A (enExample) |
| OA (1) | OA05802A (enExample) |
| PT (1) | PT67271B (enExample) |
| YU (2) | YU40019B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5395969A (en) * | 1976-12-20 | 1978-08-22 | Wellcome Found | Imidazoline derivative and insecticide containing same |
| EP0001647B1 (en) * | 1977-10-26 | 1982-11-03 | The Wellcome Foundation Limited | Imidazoline derivatives and salts thereof, their synthesis, pesticidal formulations containing the imidazolines, preparation thereof and their use as pesticides |
| ZA787351B (en) * | 1978-06-19 | 1980-08-27 | Wellcome Found | Imidazolines,their preparation,intermediates therefor,and pesticidal formulations and use of the imidazolines |
| DE3842798A1 (de) * | 1988-12-20 | 1990-06-21 | Hoechst Ag | Imidazolinderivate enthaltende mittel zur wirtstiersystemischen bekaempfung von ektoparasiten sowie neue imidazolinderivate |
| JP2008540441A (ja) * | 2005-05-03 | 2008-11-20 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 殺虫性の置換されたアミノアルキル複素環式及びヘテロアリール誘導体 |
| EP2173720A2 (en) * | 2007-07-02 | 2010-04-14 | F. Hoffmann-Roche AG | 2-imidazolines having a good affinity to the trace amine associated receptors (taars) |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA563673A (en) * | 1958-09-23 | Miescher Karl | 2-(n:n-diphenyl-aminoethyl)-imidazolines and process of making same | |
| CH234982A (de) * | 1938-05-11 | 1944-10-31 | Chem Ind Basel | Verfahren zur Darstellung eines neuen therapeutisch wirksamen Amidins. |
| DE701322C (de) * | 1938-05-11 | 1941-01-14 | Chemische Ind Ges | Verfahren zur Darstellung von Imidazolin- und Tetrahydropyrimidinverbindungen |
| CH234987A (de) * | 1938-05-11 | 1944-10-31 | Chem Ind Basel | Verfahren zur Darstellung eines neuen therapeutisch wirksamen Amidins. |
| CH234983A (de) * | 1938-05-11 | 1944-10-31 | Chem Ind Basel | Verfahren zur Darstellung eines neuen therapeutisch wirksamen Amidins. |
| CH234986A (de) * | 1938-05-11 | 1944-10-31 | Chem Ind Basel | Verfahren zur Darstellung eines neuen therapeutisch wirksamen Amidins. |
| US3193454A (en) * | 1959-04-27 | 1965-07-06 | Standard Oil Co | Insecticidal oil-soluble chlorinated substituted imidazolines |
| GB1174349A (en) * | 1966-08-25 | 1969-12-17 | Boehringer Sohn Ingelheim | Novel 2-Anilinomethylimidazoline Derivatives and process for the preparation thereof |
| US3862318A (en) * | 1969-12-09 | 1975-01-21 | Millmaster Onyx Corp | Microbiocidal naphthenyl imidazolines |
| DE2235093C2 (de) * | 1972-07-18 | 1974-07-04 | Bayer Ag, 5090 Leverkusen | Korrosionsschutzmittel |
| JPS51106739A (en) * | 1975-03-12 | 1976-09-21 | Takeda Chemical Industries Ltd | Satsuchu satsudanizai |
-
1977
- 1977-11-10 NL NL7712401A patent/NL7712401A/xx not_active Application Discontinuation
- 1977-11-11 BR BR7707589A patent/BR7707589A/pt unknown
- 1977-11-14 AR AR269973A patent/AR216660A1/es active
- 1977-11-14 IL IL53374A patent/IL53374A/xx unknown
- 1977-11-14 PT PT67271A patent/PT67271B/pt unknown
- 1977-11-14 GB GB47367/77A patent/GB1592699A/en not_active Expired
- 1977-11-14 CA CA290,708A patent/CA1104143A/en not_active Expired
- 1977-11-14 DE DE19772750902 patent/DE2750902A1/de not_active Withdrawn
- 1977-11-15 MX MX776558U patent/MX5135E/es unknown
- 1977-11-15 ES ES464150A patent/ES464150A1/es not_active Expired
- 1977-11-15 IT IT29695/77A patent/IT1143778B/it active
- 1977-11-15 NZ NZ185685A patent/NZ185685A/xx unknown
- 1977-11-15 EG EG640/77A patent/EG12913A/xx active
- 1977-11-15 YU YU2721/77A patent/YU40019B/xx unknown
- 1977-11-15 OA OA56316A patent/OA05802A/xx unknown
- 1977-11-16 FR FR7734431A patent/FR2380733A1/fr active Granted
- 1977-11-16 JP JP13776277A patent/JPS5363378A/ja active Pending
-
1978
- 1978-05-31 FR FR7816218A patent/FR2381030A1/fr active Granted
-
1979
- 1979-05-29 US US06/042,822 patent/US4254133A/en not_active Expired - Lifetime
-
1982
- 1982-08-09 YU YU1731/82A patent/YU39701B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR7707589A (pt) | 1978-06-20 |
| NZ185685A (en) | 1980-09-12 |
| ES464150A1 (es) | 1979-01-01 |
| JPS5363378A (en) | 1978-06-06 |
| OA05802A (fr) | 1981-05-31 |
| IL53374A (en) | 1983-06-15 |
| US4254133A (en) | 1981-03-03 |
| DE2750902A1 (de) | 1978-05-24 |
| PT67271B (en) | 1979-04-18 |
| NL7712401A (nl) | 1978-05-18 |
| AR216660A1 (es) | 1980-01-15 |
| FR2381030B1 (enExample) | 1982-10-01 |
| PT67271A (en) | 1977-12-01 |
| YU40019B (en) | 1985-06-30 |
| FR2380733B1 (enExample) | 1982-07-30 |
| EG12913A (en) | 1980-12-31 |
| MX5135E (es) | 1983-03-28 |
| YU39701B (en) | 1985-03-20 |
| CA1104143A (en) | 1981-06-30 |
| FR2380733A1 (fr) | 1978-09-15 |
| YU272177A (en) | 1983-01-21 |
| IL53374A0 (en) | 1978-01-31 |
| IT1143778B (it) | 1986-10-22 |
| FR2381030A1 (fr) | 1978-09-15 |
| YU173182A (en) | 1983-01-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |