DE1770269C3 - Imidazol-Derivate und herbizide Mittel - Google Patents
Imidazol-Derivate und herbizide MittelInfo
- Publication number
- DE1770269C3 DE1770269C3 DE1770269A DE1770269A DE1770269C3 DE 1770269 C3 DE1770269 C3 DE 1770269C3 DE 1770269 A DE1770269 A DE 1770269A DE 1770269 A DE1770269 A DE 1770269A DE 1770269 C3 DE1770269 C3 DE 1770269C3
- Authority
- DE
- Germany
- Prior art keywords
- imidazole
- parts
- tribromo
- active ingredient
- trichloroimidazole
- 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
- 150000002460 imidazoles Chemical class 0.000 title claims description 7
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title claims description 7
- 239000004009 herbicide Substances 0.000 title description 3
- 239000004480 active ingredient Substances 0.000 description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- -1 alkyl radical Chemical group 0.000 description 24
- 241000196324 Embryophyta Species 0.000 description 22
- 238000012360 testing method Methods 0.000 description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000002363 herbicidal effect Effects 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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- 238000002474 experimental method Methods 0.000 description 7
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- 239000002904 solvent Substances 0.000 description 7
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- KCUCKJJLMMZKBV-UHFFFAOYSA-N 2,4,5-trichloro-1h-imidazole Chemical compound ClC1=NC(Cl)=C(Cl)N1 KCUCKJJLMMZKBV-UHFFFAOYSA-N 0.000 description 4
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- 239000013543 active substance Substances 0.000 description 3
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- 150000002170 ethers Chemical class 0.000 description 3
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- 239000002689 soil Substances 0.000 description 3
- JJYRORJLOMOBKX-UHFFFAOYSA-N 2,4,5-tribromo-1-(propan-2-yloxymethyl)imidazole Chemical compound C(C)(C)OCN1C(=NC(=C1Br)Br)Br JJYRORJLOMOBKX-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
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- 235000008504 concentrate Nutrition 0.000 description 2
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- 235000013312 flour Nutrition 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
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- 125000005394 methallyl group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
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- HANFGYYVBCDRGL-UHFFFAOYSA-N (2,4,5-tribromoimidazol-1-yl)methanol Chemical compound OCN1C(Br)=NC(Br)=C1Br HANFGYYVBCDRGL-UHFFFAOYSA-N 0.000 description 1
- DGKXRRIUWDMTNX-UHFFFAOYSA-N 2,4,5-tribromo-1-(2-methylpropoxymethyl)imidazole Chemical compound C(C(C)C)OCN1C(=NC(=C1Br)Br)Br DGKXRRIUWDMTNX-UHFFFAOYSA-N 0.000 description 1
- SAVZJULTHDHKCX-UHFFFAOYSA-N 2,4,5-tribromo-1-(hexoxymethyl)imidazole Chemical compound C(CCCCC)OCN1C(=NC(=C1Br)Br)Br SAVZJULTHDHKCX-UHFFFAOYSA-N 0.000 description 1
- YFXDMMDCUGCCGY-UHFFFAOYSA-N 2,4,5-tribromo-1-(methoxymethyl)imidazole Chemical compound COCN1C(Br)=NC(Br)=C1Br YFXDMMDCUGCCGY-UHFFFAOYSA-N 0.000 description 1
- MNFDIPKRZDEUMN-UHFFFAOYSA-N 2,4,5-tribromo-1-(propoxymethyl)imidazole Chemical compound C(CC)OCN1C(=NC(=C1Br)Br)Br MNFDIPKRZDEUMN-UHFFFAOYSA-N 0.000 description 1
- KAMDVXMJRMNDCQ-UHFFFAOYSA-N 2,4,5-tribromo-1-methylimidazole Chemical compound CN1C(Br)=NC(Br)=C1Br KAMDVXMJRMNDCQ-UHFFFAOYSA-N 0.000 description 1
- DJHFVSKYCQRRPZ-UHFFFAOYSA-N 2,4,5-trichloro-1-(2-methoxyethyl)imidazole Chemical compound COCCN1C(=NC(=C1Cl)Cl)Cl DJHFVSKYCQRRPZ-UHFFFAOYSA-N 0.000 description 1
- REGKICVWSODSAI-UHFFFAOYSA-N 2,4,5-trichloro-1-(pentoxymethyl)imidazole Chemical compound CCCCCOCN1C(Cl)=NC(Cl)=C1Cl REGKICVWSODSAI-UHFFFAOYSA-N 0.000 description 1
- AXHRGVJWDJDYPO-UHFFFAOYSA-N 2-bromo-1h-imidazole Chemical compound BrC1=NC=CN1 AXHRGVJWDJDYPO-UHFFFAOYSA-N 0.000 description 1
- OCVXSFKKWXMYPF-UHFFFAOYSA-N 2-chloroimidazole Chemical compound ClC1=NC=CN1 OCVXSFKKWXMYPF-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- WPGPOYRQEZIAAG-UHFFFAOYSA-N 4,5-dibromo-2-chloro-1-(propoxymethyl)imidazole Chemical compound C(CC)OCN1C(=NC(=C1Br)Br)Cl WPGPOYRQEZIAAG-UHFFFAOYSA-N 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000008096 xylene 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
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D233/68—Halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH596067A CH485733A (de) | 1967-04-26 | 1967-04-26 | Verfahren zur Herstellung halogensubstituierter Imidazol-Derivate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1770269A1 DE1770269A1 (de) | 1972-04-27 |
| DE1770269B2 DE1770269B2 (de) | 1975-01-23 |
| DE1770269C3 true DE1770269C3 (de) | 1975-09-18 |
Family
ID=4302145
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1770269A Expired DE1770269C3 (de) | 1967-04-26 | 1968-04-25 | Imidazol-Derivate und herbizide Mittel |
| DE19681770270 Pending DE1770270A1 (de) | 1967-04-26 | 1968-04-25 | Neue Imidazolderivate und Verfahren zu deren Herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681770270 Pending DE1770270A1 (de) | 1967-04-26 | 1968-04-25 | Neue Imidazolderivate und Verfahren zu deren Herstellung |
Country Status (14)
| Country | Link |
|---|---|
| US (5) | US3625955A (enExample) |
| AT (4) | AT280279B (enExample) |
| BE (3) | BE714241A (enExample) |
| BR (1) | BR6898630D0 (enExample) |
| CA (1) | CA928306A (enExample) |
| CH (3) | CH485412A (enExample) |
| DE (2) | DE1770269C3 (enExample) |
| DK (2) | DK125284B (enExample) |
| ES (6) | ES353180A1 (enExample) |
| FR (3) | FR1567372A (enExample) |
| GB (3) | GB1197103A (enExample) |
| IL (3) | IL29887A (enExample) |
| NL (3) | NL139313B (enExample) |
| SE (3) | SE354176B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH485412A (de) * | 1967-04-26 | 1970-02-15 | Agripat Sa | Mittel zur Bekämpfung tierischer und pflanzlicher Schädlinge |
| CH510394A (de) * | 1969-07-04 | 1971-07-31 | Ciba Geigy Ag | Akarizides Mittel |
| FR2104652A2 (en) * | 1970-04-29 | 1972-04-21 | Agripat Sa | 1-alkoxymethyl-2, 4, 5-trichloroimidazoles - insecticides and acaricides |
| US3934019A (en) * | 1970-12-18 | 1976-01-20 | Bayer Aktiengesellschaft | Pesticidal 4,5-bis-(trifluoromethylimino)-diazoles |
| US4089672A (en) * | 1972-12-20 | 1978-05-16 | The Upjohn Company | 1-(Substituted-hydrocarbyl)-di- and trihalopyrazoles |
| DE2314985A1 (de) * | 1973-03-26 | 1974-10-17 | Hoechst Ag | 1-(imidazol-1-yl)-isochinoline und verfahren zu ihrer herstellung |
| NZ178996A (en) * | 1974-11-15 | 1978-06-02 | Kornis G | Pyrfazole amides and thioamides;herbicidal compositions |
| US4179277A (en) * | 1976-03-12 | 1979-12-18 | Bayer Aktiengesellschaft | 4,5-Dichloroimidazole-2-carboxylic acid derivatives |
| DE2646142A1 (de) * | 1976-10-13 | 1978-04-20 | Bayer Ag | 1-acyloxymethyl-4,5-dichlor- imidazol-2-carbonsaeure-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenschutzmittel |
| US4187100A (en) * | 1976-10-13 | 1980-02-05 | Bayer Aktiengesellschaft | 4,5-Dichloro-imidazole-1-carboxylic acid aryl esters and their use as herbicides |
| DE2646144A1 (de) * | 1976-10-13 | 1978-04-20 | Bayer Ag | 4,5-dichlor-imidazol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenschutzmittel |
| DE2646143A1 (de) * | 1976-10-13 | 1978-04-20 | Bayer Ag | 4,5-dichlor-imidazol-1-carbonsaeure- arylester, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenschutzmittel |
| US4185991A (en) * | 1976-10-13 | 1980-01-29 | Bayer Aktiengesellschaft | 4,5-Dichloro-imidazole derivatives and their use as herbicides |
| EG17668A (en) * | 1984-11-22 | 1990-08-30 | Sumitomo Chemical Co | Process for preparing of a bromodichlorimidazole insecticide |
| JPS6239577A (ja) * | 1985-08-15 | 1987-02-20 | Sumitomo Chem Co Ltd | トリハロイミダゾ−ル誘導体、その製造法およびそれを有効成分とする殺虫剤 |
| DE3828208A1 (de) * | 1988-08-19 | 1990-02-22 | Basf Ag | Substituierte 2-chlorimidazolderivate, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide mittel |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1567084A1 (de) * | 1963-07-01 | 1970-10-15 | Shell Int Research | Mittel zur Bekaempfung unerwuenschten Pflanzenwuchses |
| US3501286A (en) * | 1964-06-29 | 1970-03-17 | Shell Oil Co | Plant growth control |
| DE1294086B (de) * | 1964-08-07 | 1969-04-30 | Shell Int Research | Herbizide Mittel |
| GB1154722A (en) * | 1965-07-08 | 1969-06-11 | Boots Pure Drug Co Ltd | 2,4,5-Tribromoimidazole Derivatives and Compositions thereof |
| US3409606A (en) * | 1965-12-30 | 1968-11-05 | American Cyanamid Co | Halogenated chloroimidazole compounds |
| US3435050A (en) * | 1966-04-08 | 1969-03-25 | Dow Chemical Co | 2,4,5-trichloroimidazole and method of preparation |
| FR1494338A (fr) * | 1966-07-29 | 1967-09-08 | Chimetron Sarl | Sulfénylimidazoles |
| CH485412A (de) * | 1967-04-26 | 1970-02-15 | Agripat Sa | Mittel zur Bekämpfung tierischer und pflanzlicher Schädlinge |
-
1967
- 1967-04-26 CH CH25470A patent/CH485412A/de not_active IP Right Cessation
- 1967-04-26 CH CH25370A patent/CH485736A/de not_active IP Right Cessation
- 1967-04-26 CH CH596067A patent/CH485733A/de not_active IP Right Cessation
-
1968
- 1968-04-24 US US723904A patent/US3625955A/en not_active Expired - Lifetime
- 1968-04-24 US US723903A patent/US3625953A/en not_active Expired - Lifetime
- 1968-04-25 ES ES353180A patent/ES353180A1/es not_active Expired
- 1968-04-25 BE BE714241D patent/BE714241A/xx unknown
- 1968-04-25 DE DE1770269A patent/DE1770269C3/de not_active Expired
- 1968-04-25 ES ES353179A patent/ES353179A1/es not_active Expired
- 1968-04-25 ES ES353177A patent/ES353177A1/es not_active Expired
- 1968-04-25 AT AT403968A patent/AT280279B/de not_active IP Right Cessation
- 1968-04-25 AT AT492969A patent/AT291667B/de not_active IP Right Cessation
- 1968-04-25 SE SE05584/68A patent/SE354176B/xx unknown
- 1968-04-25 ES ES353182A patent/ES353182A1/es not_active Expired
- 1968-04-25 IL IL29887A patent/IL29887A/en unknown
- 1968-04-25 GB GB19571/68A patent/GB1197103A/en not_active Expired
- 1968-04-25 DK DK189368AA patent/DK125284B/da unknown
- 1968-04-25 GB GB19569/68A patent/GB1197101A/en not_active Expired
- 1968-04-25 DE DE19681770270 patent/DE1770270A1/de active Pending
- 1968-04-25 GB GB19570/68A patent/GB1197102A/en not_active Expired
- 1968-04-25 FR FR1567372D patent/FR1567372A/fr not_active Expired
- 1968-04-25 FR FR1567373D patent/FR1567373A/fr not_active Expired
- 1968-04-25 CA CA018359A patent/CA928306A/en not_active Expired
- 1968-04-25 BE BE714239D patent/BE714239A/xx unknown
- 1968-04-25 SE SE05585/68A patent/SE354072B/xx unknown
- 1968-04-25 ES ES353181A patent/ES353181A1/es not_active Expired
- 1968-04-25 SE SE05586/68A patent/SE352804B/xx unknown
- 1968-04-25 FR FR1567374D patent/FR1567374A/fr not_active Expired
- 1968-04-25 IL IL29888A patent/IL29888A/xx unknown
- 1968-04-25 BR BR198630/68A patent/BR6898630D0/pt unknown
- 1968-04-25 IL IL29886A patent/IL29886A/xx unknown
- 1968-04-25 NL NL686805901A patent/NL139313B/xx unknown
- 1968-04-25 BE BE714240D patent/BE714240A/xx unknown
- 1968-04-25 NL NL6805900A patent/NL6805900A/xx unknown
- 1968-04-25 ES ES353178A patent/ES353178A1/es not_active Expired
- 1968-04-25 AT AT404068A patent/AT280280B/de active
- 1968-04-25 AT AT404168A patent/AT280692B/de not_active IP Right Cessation
- 1968-04-25 NL NL6805899A patent/NL6805899A/xx unknown
- 1968-04-25 DK DK189168AA patent/DK125565B/da unknown
-
1970
- 1970-06-08 US US44558A patent/US3674874A/en not_active Expired - Lifetime
-
1971
- 1971-04-05 US US00131447A patent/US3773960A/en not_active Expired - Lifetime
- 1971-06-28 US US00157698A patent/US3759945A/en not_active Expired - Lifetime
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHV | Ceased/renunciation |